<![CDATA[Andrew Yeung's Newsletter]]>https://www.andrew.todayhttps://substackcdn.com/image/fetch/$s_!-iwE!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd027cdf0-2305-4b1a-8b80-d20edc593425_1080x1080.pngAndrew Yeung's Newsletterhttps://www.andrew.todaySubstackSat, 02 May 2026 21:13:55 GMT<![CDATA[Observations: AI in San Francisco]]>https://www.andrew.today/p/observations-from-the-ai-bubble-inhttps://www.andrew.today/p/observations-from-the-ai-bubble-inFri, 10 Apr 2026 14:55:32 GMT👋 Hey, it’s Andrew.

Good morning from San Francisco. The past few days have been b2b attending the HumanX AI conference, Zero Click by Profound marketing AI summit, and hosting two CEO dinners of my own. Today, I’m doing the ‘non-tech’ stuff in the valley, heading down to Carmel-by-the-Sea for the first time to unplug. Before I do, here are my observations from within the AI bubble in SF.

📅 Upcoming Events

San Francisco, the AI capital of the world.

There is no place in the world like San Francisco.

Google, Apple, Meta, OpenAI. All born in the Valley. And as Tony Robbins once said, “proximity is power.” By being close to the epicenter, you receive information, access, and capital first.

This has only intensified over the last three years with the rise of AI, frontier labs, and LLMs. There is a massive wave happening here that slowly trickles everywhere else.

I visit San Francisco a few times a year on a quest for “alpha”: new information or unconventional ways of thinking that haven’t made their way across the coast yet. Every time, I’m surprised.

This trip, I gathered 50 CEOs over dinner, visited OpenAI, met with banks and VC funds, and spoke with a few dozen people, including investors at the largest venture capital fund in the world, senior operators at frontier labs, creators, and CEOs of eight-figure companies. People who I thought had the best grasp of what tech is like in San Francisco right now.

I hosted a dinner for AI CEOs in SF.

My observations:

  • The talent density is even more intense than you expect. You can’t walk through San Francisco without bumping into a VC. If you are raising money for your startup, this is a good place to be.

  • The perception of abundance. The scale of companies is generally larger: more capital, more revenue, more headcount. As a result, there’s a mindset that there is greater abundance, more talent, and more opportunity. Techno-optimism.

  • “You can just do things.” Among the people close to the technology, there is a general attitude that anything is possible. You can build anything you want in a day without knowing how to code, and just start building things; you’re no longer blocked by your ability to find engineers or raise capital.

  • But everyone is stressed. In the majority of my conversations with operators, founders, investors, and old friends and new, people are feeling anxious. There is a lot of FOMO. Things are moving too quickly. And there’s the unknown: with everyone racing toward AGI, what happens after?

  • Status games are everywhere. There is a heavy obsession with status signaling, or anti-status signaling (which accomplishes the same outcome). Understandable given information asymmetry in venture when millions of dollars are on the line.

  • There is a clear inequality of information, wealth, status, and access. It was surreal to take a meeting with an investor managing hundreds of millions of dollars, then get into an Uber where the driver had never heard of vibe coding.

  • Speaking of Uber, 75% of the drivers attempted to network. "So what do you do for work?" was a constant. One driver asked me for career advice (I’m in no place to give a stranger career advice). There's a clear level of ambition happening in this city.

  • There is consensus on the clearest opportunity for quick riches. If you want to become an entrepreneur right now, do some form of AI implementation (help organizations adopt AI) or AI enablement (help people learn AI).

  • The pecking order is shifting. For three decades, Silicon Valley was engineering and product-driven. I saw this at Google and Meta. Zuck built the product, then hired business people to sell and monetize it. Product first, business second. Now it's research first, engineering second. The makeup of talent at frontier labs like OpenAI is heavily concentrated on the researcher profile (who, by the way, get paid millions of dollars a year). This impacts how decisions are made and incentives are set, and ultimately trickles down to everyone else.

  • Who will be most valuable in a post-AGI world? Lots of discussion on this during our dinner. The general belief: if you're non-technical, having an educator background (teacher) or liberal arts experience (drama, theatre) is a good place to be, because you can do things that AI cannot. There will only be four jobs is a good read.

  • Complete and total immersion. SF is the optimal place to be if you need to lock in. Everyone, everywhere is working. There are even 24/7 cafes, funded by venture-backed startups, that incentivize people to grind around the clock.

The 24/7 Corgi cafe.

  • The Silicon Valley Consensus is real. A large density of people thinking the same way, building the same thing, going after the same market. People in other markets may not have strong opinions, and people here do, but they're all similar.

  • Proximity to the greats. A big reason SF is the way it is: the greats are around and involved. The founders of Google, Airbnb, Facebook, DoorDash, OpenAI, Salesforce, etc. They regularly speak, mentor, angel invest, and participate in the ecosystem. This is incredibly rare, and few other markets have this.

A very SF story: I visited a new Twitter acquaintance’s Michelin-starred steakhouse with my friend Bailey (CEO, Cal.com). The owner of the restaurant owns multiple restaurants while running an a16z-backed tech startup. What?!

  • Proportion of missionaries vs mercenaries. In other markets like NYC, Miami, and LA, I’ve noticed that people optimize their careers around compensation. People here are willing to take a longer-term view in service of a larger, more fulfilling mission.

  • Multiple friends told me this is the most stressed they've ever been. But also the happiest they've ever been. A paradox that you would only understand if you are ‘AI-pilled.’

  • Peptides are all the rage.

  • The highest-status career moves right now: Work at a frontier lab (Anthropic, OpenAI, Gemini), build an AI company, or create content.

After spending a week here, I’ve realized one thing: I need to go and touch grass.

Met this dawg at HumanX, one of the world's most prominent AI conferences.

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 👀 Profound just got a MAJOR upgrade with Profound Sheets. Profound Sheets lets you run hundreds of AI agents in parallel, saving you hours of time. Learn more here.

  • 🧮 Need a CPA? I’ll introduce you to Alex, with whom I’ve been working for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🤖 Winner AI is an AI-driven hiring engine built for fast-scaling startups, combining advanced machine intelligence with human experts to deliver top technical talent with speed and precision. Learn more.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

]]><![CDATA[How to Talk to Anyone]]>https://www.andrew.today/p/how-to-talk-to-anyonehttps://www.andrew.today/p/how-to-talk-to-anyoneMon, 23 Mar 2026 11:30:18 GMT👋 Hey, it’s Andrew.

Quick note: Everyone in NYC tech is talking about this: NY may eliminate QSBS and retroactively tax startup exits for founders, employees, and investors. If passed, it could make New York one of the least attractive places to build and invest in startups.

Tech:NYC has put together an open letter to Albany. Takes two minutes to sign. Deadline is today at noon. Sign here.

…

My team and I just got back from Austin, where we had an unforgettable few days meeting dozens of founders and CEOs, and even throwing a 2,000-person tech party.

In a few weeks, we’ll be in San Francisco. If you’re around, I’d love to see you there.

Today’s article is about an increasingly rare skill: the art of conversation.

📅 Upcoming Events

• • •

I was terribly awkward until my early twenties.

I found it difficult to talk to service staff, strangers at parties, anyone I didn’t already know. Part of it was cultural. I spent two decades in China, an only child with quiet parents. Part of it was confidence. Either way, conversation didn’t come naturally.

My bible for surviving high school was a little yellow book called “How to Talk to Anyone.” I studied it religiously.

The biggest misconception is that most people think you’re either naturally good at it or you’re not. But it’s not true. Some of the best conversationalists I’ve met weren’t born that way. They learned and developed specific habits and techniques over time.

Today I host fireside chats with prominent entrepreneurs: Sahil Bloom, the founders of Venmo, Foursquare, BarkBox, and many others.

Put me in a room with anyone, and I can get them to reveal their deepest darkest secrets.

Last week in Austin, I spoke to over a hundred people, and it reminded me of where I started from: a clueless, shy introvert. And I’m writing this today to share with all of you who were in my shoes a decade ago that yes, it can’t be changed.

Interviewing Sahil Bloom at our OOO Summit in 2025.

Here’s what I’ve learned from studying the best interviewers, hosts, and conversationalists in the world, and how you can apply it.

• • •

What makes a great conversationalist?

It’s not about being the most interesting person in the room, or even having the most interesting things to say, but about making the other person feel like the most interesting person in the room.

Dale Carnegie wrote about this nearly 90 years ago in “How to Win Friends and Influence People. He tells the story of attending a dinner party where he barely spoke all night. He mostly asked questions and listened. Afterward, the host told others he was “the most interesting conversationalist” at the party. He’d said almost nothing.

The best conversationalists aren’t waiting for their turn to talk. They’re curious, listening, and interested in what the other person will say next. It’s a dance, not a fight. There’s no winning or impressing. But you’re playing with the other person, building something neither of you could create alone.

• • •

How to make conversation

Step 1: Make them the hero

Most people try to be the hero of every conversation. They share accomplishments, one-up stories, and impress others with their knowledge.

But great conversationalists do the opposite. They make the other person the hero.

Dale Carnegie’s most enduring insight: people care most about themselves. The best conversationalists use this for great conversation.

Remember their name. Carnegie called a person’s name “the sweetest sound” to them. Use it and remember it. It shows that you care.

Appeal to their interests, not yours. Before meeting someone important, Theodore Roosevelt would stay up late reading about subjects his guest was passionate about. He knew the way to someone’s heart was through their interests, not his own.

Ask about their wins. Their proudest moments. The obstacles they overcame. Let them be the protagonist of the story.

When someone feels like the hero in your presence, they’ll want to keep talking to you.

The legend, Dale Carnegie.

Step 2: Ask better questions

Skip the standard “What do you do?” “Where are you from?” “How’s work?” These questions produce autopilot responses.

Larry King built a legendary career on simple, direct questions. He never asked multi-part questions. He’d ask one thing, then shut up. “Why?” “How so?” “What happened next?” The silence created space for the guest to fill.

Tim Ferriss takes a different approach: unexpected questions that break people out of their rehearsed answers. “What would you put on a billboard?” “What’s a belief you’ve changed your mind on?” “What’s a purchase under $100 that changed your life?” By asking questions guests haven’t heard before, he gets fresh answers even from people who’ve done hundreds of interviews.

Ask open-ended questions that can’t be answered with a single word. Ask questions that make people think. The quality of your questions determines the quality of the conversation.

But don’t ask too many questions. A conversation isn’t an interrogation. If you’re firing question after question, the other person will feel interviewed.

Larry King, radio and talk show host.

Step 3: Use support responses, not shift responses

This is from Kate Murphy’s book “You’re Not Listening,” and it changed how I think about conversation.

A shift response turns the conversation back to you: “That happened to me too, let me tell you about it.” A support response keeps the focus on them: “What did you do next?” “How did that feel?” “Tell me more about that.”

Most people default to shift responses. Someone shares something, and we immediately relate it to our own experience. It feels like connection, but it actually redirects attention away from them.

Great conversationalists use support responses to follow the thread instead of changing it.

The other key: ask follow-up questions, instead of new questions. Amateur conversationalists have a list of questions in their head and move to the next one regardless of the answer. Great conversationalists follow the thread.

Kate Murphy, journalist & best-selling author

Step 4: Say “Yes, and”

After doing improv comedy for a few months, I’ve learned the cardinal rule of “Yes, and.” Accept what your scene partner offers and build on it.

Most people do “No, but” in conversations. They reject, correct, or redirect. “Actually, I think...” “Well, that’s not quite right...” “But have you considered...”

“Yes, and” keeps the conversation flowing and makes the other person feel heard. It doesn’t mean you agree with everything. It means you accept their contribution and add to it.

“Yes, and what happened next?”

“Yes, I see what you mean, and I’d add...”

“Yes, that’s interesting, and it makes me think of...”

When you say “yes, and,” you’re telling the other person: I hear you, I value what you said, and I want to build on it.

Step 5: Match the conversation type

Charles Duhigg’s book “Supercommunicators” explains that every conversation is actually three conversations happening at once:

  • Practical (what’s this about?)

  • Emotional (how do we feel?)

  • Social (who are we to each other?)

[elaborate on each type of conversation]

The mistake most people make is mismatching. Someone is venting about a problem, seeking emotional support. You jump in with practical advice. They feel unheard. You feel confused about why your helpful suggestion landed poorly.

Supercommunicators read which type of conversation is needed and match it. Before responding, ask yourself: What kind of conversation is this person trying to have? Then match it.

CHarles Duhigg, author and reporter for the New York Times.

Step 6: Answer the question behind the question

People rarely ask what they actually want to know. There is always a real question under the service question.

Esther Perel, the renowned therapist, is a master at this. In her podcast “Where Should We Begin?”, she listens for what people aren’t saying and gently brings it to the surface.

When someone asks, “How’s work?” they might really be asking, “Are you happy?”

When someone asks, “What do you think of my idea?” they might really be asking, “Do you believe in me?”

When a friend asks, “Are you busy this weekend?” they might really be asking, “Do you still have time for me?”

The surface question is the iceberg that is 10% above the water. The real question is the 90% below.

Listen for the question behind the question and answer that one, not just the surface question. This is how you make people feel truly understood.

Esthel Perel, psychotherapist, author & podcast host.

Step 7: Go first

Howard Stern has gotten famously guarded celebrities to reveal things they’ve never shared elsewhere. His secret: He goes first.

Stern shares his own insecurities, fears, and embarrassments openly. He talks about his therapy, his failed first marriage, his anxieties. This gives guests permission to do the same.

If you want someone to open up, you have to open up first. Share something vulnerable about yourself before asking others to do the same.

But tease information; don’t give it all at once. Share something personal, then pause. Let them respond. If you dump everything immediately, there’s nowhere to go.

The dance of conversation is gradual revelation on both sides.

Radio talk show host Howard Stern debuts his show on Sirius Satellite Radio January 09, 2006 at the network's studios at Rockefeller Center in New York City.
Howard Stern, celebrity radio talk show host.

Step 8: Let silence do the work

Most people rush to fill the silence because it feels awkward. So they jump in the moment someone stops talking.

But when you let silence sit, people gather their thoughts and often say something more interesting.

Larry King was a master of this. He’d ask a short question, then wait. The guest would answer. He’d keep waiting. Often they’d continue, going deeper than they initially intended.

The next time someone finishes speaking, count to two before responding. Often they’ll continue. And what they say next is usually more interesting than what they said first.

Step 9: Be genuinely curious

Brandon Stanton, the creator of Humans of New York, has had thousands of conversations with strangers on the street. His photos are famous, but it’s the conversations that make them powerful. People share their deepest fears, losses, and hopes with a stranger on a sidewalk.

His secret is that he has genuine curiosity. He approaches every person believing they have an interesting story. And because he believes it, he asks questions that uncover it.

Here’s the curiosity razor: If you’re bored in a conversation, you’re not asking good enough questions. Every person has something interesting about them. If you haven’t found it, you haven’t looked hard enough. When a conversation feels flat, it’s not because the other person is boring. It’s because you haven’t found the right thread yet.

Brandon Stanton, author and photographer behind Humans of New York.

Step 10: Be fully present

Here’s a razor that cuts through distraction: Talk to people as if it’s the last time you’ll ever see them.

This sounds morbid, but it shifts your attention completely. You stop thinking about what you’ll say next. You stop checking your phone. You stop scanning the room for someone more important.

What if you never saw this person again? Would you be satisfied with how this conversation went? Did you really listen? Did you really connect?

Most people are only half-present in conversations. They’re thinking about work, checking notifications, planning their next sentence. Full presence is rare but people can feel it when you give it to them.

Step 11: Exit gracefully

Great conversations have good endings.

The worst is when a conversation slowly dies, both people looking around the room, unsure how to leave. Or when someone abruptly walks away mid-sentence.

The greatest conversationalists know how to close warmly and clearly. “I’ve really enjoyed this. I’m going to grab another drink, but let’s continue this soon.” “This has been great. I should say hello to a few other people, but I’d love to pick this up another time.”

Direct, warm, and clear with no ambiguity. No awkward lingering. A graceful exit is a gift to both people.

• • •

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

You are no longer the smartest type of thing on Earth by Noah Smith – For most of history, humans were the smartest thing around. That’s no longer true. AI can now outperform us in more and more things. But Noah’s point isn’t that we become useless; it’s that our role changes.

How Social Media Shortens Your Life by Gurwinder – Social media changes how we experience time. Because the content is fast, shallow, and forgettable, our brains form fewer memories.

Why Does Everyone Hate AI? by Rex Woodbury – The backlash against AI isn’t about the tech, but about the timing. AI arrived right when trust in tech was already low, the economy feels unstable, and people are more sensitive to anything that threatens their identity or job.

Three Modes of Cognition by Kevin Kelly – A great tread about the three types of intelligence and what AI vs humans are incredible at.

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🚀 Forum Ventures is down to their last few Spring cohort spots. Think embedded cofounder, not startup school. Apply here.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 🧮 Need a CPA? I’ll introduce you to Alex, with whom I’ve been working for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🤖 Winner AI is an AI-driven hiring engine built for fast-scaling startups, combining advanced machine intelligence with human experts to deliver top technical talent with speed and precision. Learn more.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

• • •

🖼️ Behind the Scenes

We just threw our biggest party yet with over 2,000 people.

Together with our friends at The Hustle & Agree.com

Every year during SXSW, we host the Secret Austin Garden Party. Thousands of founders, investors, creators, and tech professionals from all over the world come together for one night.

This year was something else...

Live music. A live performance from the Venmo founder, Taco trucks. Cocktails. Cotton candy. A rooftop with one of the best sunsets I've ever seen in Austin.

But the most meaningful part of all this is the people

I watch strangers become friends and founders pitch investors on the patio. I saw creators meet their heroes. Someone flew in from London just for this.

On stage together with Iqram, Venmo co-founder
It was like a music festival!
]]><![CDATA[HOW TO BUILD TASTE (For the Everyday Person)]]>https://www.andrew.today/p/how-to-build-taste-a-practical-guidehttps://www.andrew.today/p/how-to-build-taste-a-practical-guideWed, 11 Mar 2026 12:32:16 GMT👋 Hey, it’s Andrew.

Today’s piece is about the concept of taste. What it is, why it’s important, and how you can build it. It’s a buzzy topic, and I’d love to hear your input (hit reply).

Beyond that, my team and I are heading to Austin today for SXSW. If you’re around, please say hello. A few weeks later, we’ll be in SF to host a few events too.

📅 Upcoming Events

📌 Unofficial Events List for SXSW 2026 – my curated list of events and parties happening, updated daily; Submit your event to our events list here

• • •

Taste has become the latest buzzword in tech. Every prominent tech person, from Paul Graham (Founder of YCombinator) to Dylan Field (Founder, CEO of Figma), is talking about it. Yet I have yet to meet a single person in my peer group who can define it well, let alone teach it.

If you’re not plugged in to Silicon Valley, here’s the narrative over the last 1–2 years:

The consensus is that, because AI can now do everything, from coding to designing to building decks, techno-optimists argue that the remaining human edge is taste.

Taste is Eating Silicon Valley. | Robert Leduc
Graphic stolen from Anu Atluru’s essay “Taste Is Eating Silicon Valley.”

We all recognize that taste is important. But how do we actually discover and build it?

I went down a rabbit hole, reading dozens of articles and essays to try to define it in practical terms. Here’s my best attempt.

• • •

What even is taste?

Who comes to mind when you think of someone with good taste?

It might be someone who dresses stylishly, recommends great restaurants, writes poetically, and has a well-decorated apartment.

The truth is that taste is hard to define but easy to recognize.

interior design visualization 3ds max design CoronaRender archviz cgı
What I believe to be ‘tasteful’ interior design.

Some might argue: Is there even such a thing as good taste? Or is it just personal preference?

I think yes. Paul Graham made the point that if taste were just personal preference, then everyone’s taste would already be perfect. You like what you like, and that’s it.

But that would mean no artist can ever improve. No chef can be better than any other chef. No designer can be more skilled than a random person off the street.

That’s obviously not true. So taste must be real… and if it’s real, it can be developed.

Most people think taste is something you’re born with. You either have it or you don’t. I believe that’s wrong. Taste is a skill that can be discovered and built. And right now, it might be the most important skill you can develop.

Emily Weiss, founder of Glossier, described taste as a form of pattern recognition. Before she ever created a product, she spent years running Into The Gloss, interviewing hundreds of women about their beauty routines. She was building a library of references without knowing what she'd do with it. "You have to see a lot before you can identify what's exceptional," she's said. The library came first. The taste followed.

Glossier CEO Emily Weiss doesn't have time for excuses: “Just do your job”
Emily Weiss, Founder & CEO of Glossier

Derek Guy, the menswear writer with over a million followers, pushed this further. He sees taste as a language. Your choices, whether clothing, content, the events you host, or the products you build, are vocabulary, grammar, and syntax. They communicate something about who you are. And just like any language, you learn it through immersion, practice, and making a lot of mistakes.

• • •

Why taste matters now (more than it ever has)

A few days ago, Sam Altman posted that the best way for people to contribute in the AI era is through “context, taste, and a real feel for where the field is headed.” Greg Brockman, OpenAI’s president, said it more directly: “Taste is a new core skill.”

Paul Graham posted this month: “In the AI age, taste will become even more important. When anyone can make anything, the big differentiator is what you choose to make.”

AI can now write, design, code, compose, and create at scale. The cost of making things is trending toward zero. The hard part is no longer making something, but knowing what’s worth making.

That’s taste. It’s the filter. The ability to look at a thousand options and say, “No. No. No. No... Yes. That one.”

This applies to everything. Your career. Your content. The products you build. The events you host. The people you surround yourself with. The life you design.

Photo by Gizem Akdag on January 01, 2026. May be an image of horse and text.

I host over a hundred events a year across New York, San Francisco, and Austin. The difference between a forgettable networking mixer and a room people talk about for months has nothing to do with budget and everything to do with taste. Who’s in the room. What’s not on the agenda. The details people feel but can’t name. It takes great taste to fill a room with high-quality people. Otherwise, why would they come?

• • •

How to build taste

Step 1: Notice more

Taste starts before you create a single thing. It starts with observing.

Most people consume on autopilot. They scroll without registering what stops them. They eat without tasting. They walk into a room and don’t notice why it feels good or bad. They absorb everything and interrogate nothing.

Rick Rubin is arguably the greatest music producer alive. He’s worked with Jay-Z, Johnny Cash, Kanye, the Red Hot Chili Peppers, Adele. And he has no technical ability. He doesn’t play instruments. He doesn’t operate the mixing board. His entire value is his ability to notice what others miss.

In a conversation with Tyler Cowen, Rubin explained that his process is about deep attention. When an artist plays him a track, he’s not listening for what’s there. He’s listening for what’s missing. What’s not working. What could be removed. He once made Johnny Cash re-record a song dozens of times, not because Cash was singing it wrong, but because he hadn’t yet sung it with the emotional truth Rubin knew was possible. Rubin’s taste isn’t technical, but perceptual. He notices what others feel but can’t articulate.

Rick Rubin: Def Jam founder and producer announces debut book | Rick Rubin | The Guardian
Rick Rubin and Tom Petty during the recording of Petty’s album Wildflowers

So the next time something catches your eye, stop. Don’t just keep scrolling. Ask yourself what specifically pulled you in. Was it the color? The proportion? The phrasing? The silence around it? And when something feels “off,” a restaurant, a website, a piece of content, don’t dismiss the feeling. Sit with it. What’s missing? What’s too much? What would you change?

Start keeping a taste file. Screenshots, photos, bookmarks. Not just things you like, but things that make you feel something. Over time, patterns will emerge. Those patterns are the early outline of your taste.

• • •

Step 2: Consume outside your algorithm

You cannot develop taste by consuming the same thing every day. If your entire creative diet comes from the algorithmic feed, your taste will be algorithmic. Which is to say, it won’t be yours at all.

Virgil Abloh understood this better than almost anyone. He got a degree in civil engineering, then a masters in architecture. He became Kanye West’s creative director, launched Off-White, designed furniture, and became artistic director of Louis Vuitton menswear, and even DJed on the side.

Virgil Abloh Designed Way More Than Just Clothing | GQ
Virgil Abloh, Founder & CEO of Off-White, Artisti Director at Louis Vuitton

None of those disciplines are the same. But Abloh’s taste carried across all of them because it was built on a foundation wider than any single field. His famous “3% rule” was that you only need to change an existing design by 3% to make it new. But the unspoken prerequisite: you have to know what already exists to know what to change.

This means going to the source material instead of the summary. Looking at actual architecture instead of design blogs. Watching the original film instead of the reaction video. Reading the book instead of the thread about the book.

It means cross-pollinating. If you’re in tech, go to an art gallery. If you’re in fashion, read about engineering. If you write content, study standup comedy. The best taste comes from unexpected connections between fields.

Find 3 to 5 people whose taste you deeply admire across different domains. Study their choices. Not to copy them, but to understand the invisible logic behind what they select and what they reject.

• • •

Step 3: Make things (badly)

This is where most people get stuck. They consume endlessly but never create. Or they create one thing, hate it, and stop.

Ira Glass, creator of This American Life, gave the most honest description of this stage:

“All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase. They quit.”

Read that again... Your taste is why your work disappoints you. The disappointment isn’t a sign that you lack talent, but a sign that your taste is ahead of your skill.

Ira Glass on Bringing His Radio Show This American Life to the Stage — Vogue | Vogue
Ira Glass, host & producer at The American Life.

The only way to close the gap is volume. Create regularly (weekly if you can.) Content, cooking, playlists, event planning, presentations. Anything where you make choices and live with the results.

Don’t wait until you’re “ready.” The bad version teaches you more than the perfect plan ever will.

• • •

Step 4: Pay the school fees

You will get things wrong. Repeatedly. That’s not a failure of the process. It is the process.

Mark Cho is co-founder of The Armoury and one of the most respected voices in menswear. Derek Guy featured him in his series on developing taste, and Cho shared something that changed how I think about mistakes:

“There’s a Chinese phrase for when you lose money on something that translates to ‘paying school fees.’ I’ve paid a lot of school fees, and I don’t consider any of it wasted money. Even through the mistakes, I’ve learned a lot.”

Why The Armoury's Mark Cho Is Selling His Massive Watch Collection | GQ
Mark Cho, co-founder of The Armoury

The outfit that felt right at home and wrong at the party taught you context. The content you were sure would go viral that got twelve likes taught you the difference between what you like and what resonates. The event you over-programmed because you were afraid of silence taught you restraint.

Keep a record of your school fees. What you tried, what didn’t land, and what you learned. Review it quarterly. You’ll be surprised how much your judgment improves over time.

The people to bet on are the ones who made enough mistakes to develop conviction

• • •

Step 5: Edit ruthlessly

The counterintuitive truth is that taste is not what you add, but what you take away

When Jony Ive arrived at Apple in 1992, the company’s products were dull. Design was not a priority, and Jony almost quit multiple times. Then Steve Jobs came back, and everything changed. Not because they started adding more, but because they started saying no.

Apple's Design Icon - Sir Jonathan Ive
Jony Ive, former Chief Design Officer at Apple

Ive described Jobs as the most focused person he’d ever met. The discipline at Apple wasn’t innovation in the way most people imagine it. It was the habit of saying no far more often than yes. Fewer projects, considered more carefully.

Jobs told Ive something that became his design philosophy:

“When you make something with care, even though you don’t know who the people using it will be, they will sense it.”

Anna Wintour (Vogue) operates the same way. She's led Vogue for over 35 years and built her reputation on decisiveness. "I'm always editing," she's said. "I think it's very important to know what you want and go after it." For Wintour, taste is about knowing what you don't like as clearly as you know what you do, and cutting without hesitation.

Anna Wintour: The Icon Who Shaped the Met Gala and Redefined Fashion | Vogue College of Fashion
Anna Wintour, editor-in-chief of Vogue

Ive’s own line is one of the best things ever said about taste: “It’s very easy to be different, but very difficult to be better.”

Apply this everywhere. Look at anything you’ve made. Your closet, your home, your latest piece of content, your event run-of-show. Ask yourself what you could remove to make it better.

Before you publish, send, or present anything, ask: “Is this earning its place? Or is it just filling space?”

Apple Design Chief Jony Ive Discusses Apple's Book | Fortune

• • •

Step 6: Develop coherence

This is the final step; the one that separates good taste from great taste.

Good taste is about isolated good choices. Great taste is about everything fitting together into a story that feels unmistakably yours.

Derek Guy makes this point through his language metaphor. In the same way that someone’s speech patterns and word choices reveal who they are, your aesthetic choices should do the same. Your content, your events, your wardrobe, your home, your brand. All of it should feel like it comes from the same person with a clear point of view.

Apply that beyond clothing. Could someone scroll through your content and immediately know it’s yours, even without your name on it? Could they walk into an event you produced and feel your fingerprint on every detail? Could they look at the people you’ve assembled in a room and understand the logic of why those specific humans are together?

That is coherence (the highest expression of taste)

Audit your choices across domains. Does your content voice match the energy of your in-person presence? Does your personal brand align with the experiences you create? If there are contradictions, sit with them. Some contradictions are authentic complexity. Others are just noise. Learning to tell the difference is part of the work.

Official Website of Crane Club Restaurant
Crane Club in Manhattan

• • •

How to know when you have taste

Let’s say you’ve been doing the work by noticing more, consuming widely, creating through the gap, paying the school fees, editing ruthlessly, and building coherence.

How do you know it’s working?

  • You can articulate why, not just what. You don’t just like something. You can explain what makes it work in simple, unpretentious terms. “The spacing gives it room to breathe.” “The pacing builds tension in the right places.” “That event worked because the guest list created unexpected conversations.”

  • You notice things others miss. You walk into a restaurant and immediately register the lighting, the music volume, the spacing between tables. Most people can’t tell you why a place feels good, but you can.

  • You’re comfortable saying no. To trends, to peer pressure, to the “safe” choice. You can think independently and trust your own judgment, but not necessarily out of contrarianism.

  • People ask your opinion. This is the clearest sign. When friends ask you to pick the restaurant, help them choose the outfit, give feedback on their work, review their deck.

  • Your old work embarrasses you. This is Ira Glass’s insight flipped. If you look at what you made two years ago and cringe a little, your taste has grown. That discomfort is proof of progress. If you look at it and still think it’s perfect, you’ve stopped developing.

  • Your choices tell a coherent story. There’s a throughline across your decisions. The events you host, the people you surround yourself with, the content you make, the way you show up. It all feels like it comes from the same person with a clear, specific point of view.

  • You’ve stopped copying and started curating. You’re no longer imitating someone else’s aesthetic but pulling from multiple influences and combining them into something that’s distinctly yours.

• • •

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative. Today’s theme – taste!

Taste for Makers by Paul Graham – If you want to build great things, you need taste. But unlike what most people think, taste isn’t just personal preference.

How To Develop Good Taste, Pt. 1 by Die, Workwear! – Taste shapes every choice we make - what we buy, wear, read, and surround ourselves with. But unlike the past, there’s no universal rulebook anymore. Derek explains that good taste comes from exposure, comparison, and judgment.

Taste Is Eating Silicon Valley by Anu Atluru – For years, the winning strategy in tech was simple: build better software. But as coding gets cheaper and AI makes building easier, the edge is changing. Now everyone can build decent tech. What stands out is taste.

What matters in the age of AI is taste by Sari Azout – AI can generate endless text, images, and ideas. That means the scarce skill isn’t producing content anymore but choosing what’s worth paying attention to

Status and Culture: How Our Desire for Social Rank Creates Taste, Identity, Art, Fashion, and Constant Change by David Marx – A great read that explains nearly everything about the things you choose to be.

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a validation sprint with Forum Ventures’ Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. Apply here.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 🧮 Need a CPA? I’ll introduce you to Alex, with whom I’ve been working for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🤖 Winner AI is an AI-driven hiring engine built for fast-scaling startups, combining advanced machine intelligence with human experts to deliver top technical talent with speed and precision. Learn more.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

• • •

🖼️ Behind the Scenes

I started taking improv classes a few weeks ago.

It’s been on my bucket list for years, and I finally decided to do it with my buddy Parth.

It’s exactly like I expected. Every Sunday, we spend two hours with strangers acting out skits, playing silly theatre-style games, and even delivering monologues on the spot without prep.

One thing I did not expect: how hilarious it actually was. People are naturally pretty funny.

Three observations and learnings:

1. “Yes, and.” This is the foundational rule of improv. When your scene partner says something, you accept it and build on it. You don’t block, you don’t redirect, you add. It’s a simple concept, but it’s changed the way I participate in conversations. Instead of waiting for my turn to speak, I’m listening for what I can build on.

2. You don’t always have to plan everything. I used to think I needed a script for every situation. Improv taught me that you can trust yourself to come up with something in the moment. And sometimes, what comes out unplanned is wittier and more interesting than anything you could have prepared. You might surprise yourself.

3. Conversation is a team sport. It’s not a performance. You’re not trying to be the funniest person in the room. You’re trying to make your partner look good, and they’re doing the same for you. When both people play together, the conversation flows better vs one person trying to put on a show.

If you’re someone who overthinks, overplans, or struggles to be present in conversations, I’d highly recommend giving improv a try.

]]><![CDATA[The Universal Laws of Virality (Pt. 2)]]>https://www.andrew.today/p/the-universal-laws-of-virality-pthttps://www.andrew.today/p/the-universal-laws-of-virality-ptMon, 02 Mar 2026 15:37:08 GMT👋 Hey, it’s Andrew.

Two weeks ago, I wrote an article called The Universal Laws of Virality. I asked if anyone wanted to see part two, and over 40 of you replied, so here it is.

Beyond that, I’m really excited for Austin. I rented a private mansion with a pool and a barbecue pit. We’ll be hosting folks over a few nights. If you are a founder or CEO and want to meet others in a curated setting, please apply below. We do this every year, and it’s one of my favorite event series. There is no cost to attend.

📅 Upcoming Events

🤠 South by Southwest (Austin)

🤝 Get Involved (Austin)

How to Engineer Virality (Pt. 2)

I’ve doubled my follower count (now at 47k) since publishing part one of The Universal Laws of Virality two weeks ago.

That covered the foundation: hooks, structure, platform incentives, but these are the principles I used to break through the first ceiling.

1. Invoke strong emotions

You are competing for the attention of over a billion people

If your content doesn’t feel urgent or emotionally charged, it won’t matter how clever it is. Unfortunately, algorithms do not reward intelligence - it rewards emotional reaction.

Before you post, ask yourself: What emotion do I want my audience to feel? Inspired? Scared? Entertained? Angry? Hopeful? If you don’t know the answer before you hit publish, go back and rewrite it.

Anger, awe, fear, inspiration, and belonging are the most highly arousing, emotionally charged reactions. The most viral content makes people feel something so strongly that they have to share it.

2. Optimize for memorability (not views)

A mistake most new creators make is optimizing for “virality.”

Unfortunately, the gurus who tell you to optimize for virality are not helpful. Virality is a byproduct, driven by memorability. When your content is memorable, people share it. And the more people share it, the more viral it gets

Ask yourself: How do I say this in a way they will never forget? What’s the line they’ll repeat to a friend tomorrow?

A clear leading indicator to look for is the number of saves and bookmarks. The only reason someone would bookmark something is that they find it valuable.

3. Create a system for high-frequency publishing

The truth of playing the internet lottery is that you need to maximize the number of rolls you get.

Across all platforms, you need to post at a minimum once a day. I post once to twice daily on LinkedIn. Three to four times on TikTok. Four to six times on X. Total time: one to two hours a day.

The good news: this should take six hours, but it doesn’t. I built a system that takes me less than ten minutes per video: ideation, scripting, shooting, and post-production. When I started TikTok, I knew instantly I didn’t have the capacity to produce highly edited videos, so I created a system that worked for me.

I use AI heavily in my process, but mostly in the administrative parts of content creation. If you want me to share more about my AI workflow, hit reply

4. Borrow distribution by collaborating up

You should be well-networked with the creator community. Not just because you learn from others, but because you can collaborate with other creators who are 1-2 tiers above you. This allows you to reach new audiences who already trust the person vouching for you.

Borrowed distribution allows you to grow faster than organic growth alone.

5. Speak each platform's native language

Each platform has its own subculture, its own language, its own expectations.

LinkedIn favors achievement and status signaling. TikTok rewards raw energy and fast pacing. Reels prefers high-production videos. X rewards banter and hot takes. What works on LinkedIn will flop on TikTok if you don’t adapt it.

One could argue that the packaging of the content is almost more important than the content alone. You can package the same idea across multiple channels by speaking to the platform’s native language

Study the top creators on each platform and notice how they speak. What do you notice?

6. Study outliers obsessively

When you see content that does exceptionally well (1m+ views), stop scrolling and try to identify the root causes of that virality.

Study it obsessively and break down the formula behind it. Why did this work? What was the hook? What emotion did it trigger? Why did people share it?

A helpful framework is the principles from Jonah Berger’s Contagious to understand why: social currency, triggers, emotion, public visibility, practical value, stories.

Outliers are your curriculum. The algorithm already told you what works. Your job is to understand why.

7. Earn the right to reach your audience

My contrarian opinion on social media: your follower count doesn’t matter anymore.

I have over 300,000 followers across my platforms. Yet every time I post, I believe I need to earn the right to reach my audience. Every single time. Because the truth is, since our platforms moved from a follower-first to a discovery-first mechanic, the algorithm doesn’t care how many followers you have. It cares whether this specific piece of content is good enough to show to more people.

Treat every post like you have zero followers. Would this piece of content stand on its own? Would it get engagement even if nobody knew who you were? If not, make it better before you post.

The other side of this is true as well. Even with just a single follower, you can reach a million people. The capacity to create viral content has been democratized

8. Pick a game you can win (be the top 1%)

People consume content for two reasons: education or entertainment. Pick one.

I avoided entertainment. Why: I knew I could never compete with the charisma of comedians or the post-production skills of filmmakers. That’s not my game. So I optimized for knowledge. My goal is to give people information in the clearest, most concise way possible.

Ask yourself: What am I genuinely better at than most people? What could I talk about for hours without getting bored? That’s your game - double down on it.

Don’t straddle both. If you try to be a bit educational and a bit entertaining, you’ll likely do both poorly.

9. Stay plugged into the cultural zeitgeist

A big part of playing the social media game is staying on top of trending narratives.

What’s trending? What’s hot? What’s discussable right now? This ties into understanding cultural memes and sharing things that are timely. The same content posted during a trending moment will outperform content posted a week later by a wide margin.

I use Claude Code to send me trending headlines every morning. It takes five minutes and keeps me plugged in.

I’ve mentioned AI a few times as part of my workflow. It’s a big part of it, so if you want to learn more, hit reply.

(Sponsored) This issue is brought to you by The Human Liberation.

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Get the guide: 5 Steps to End Negative Self-Talk

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Time by Maximilian Kiener – A stunning website that visualizes how fast time flies.

THE 2028 GLOBAL INTELLIGENCE CRISIS by Citrini Research – This popular article has been floating around the internet and has been read by millions. It’s a framework for you to think about where opportunity might land next in the AI era.

You are no longer the smartest type of thing on Earth by Noah Smith – The people who built the world we live in aren’t the same people who’ll build the world coming next. Applied adaptability matters more in a world where tools can execute exponentially faster than humans. A great read on our future.

Claude Code Clearly Explained (and how to use it) by Greg Isenberg – If you haven’t tried Claude Code yet, you’re missing out on an entirely new way of working. I’ve gone down a rabbit hole over the past few weeks, completely automating most of my work.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a validation sprint with Forum Ventures’ Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. Apply here.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 🧮 Need a CPA? I’ll introduce you to Alex, with whom I’ve been working for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🤖 Winner AI is an AI-driven hiring engine built for fast-scaling startups, combining advanced machine intelligence with human experts to deliver top technical talent with speed and precision. Learn more.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

]]><![CDATA[The Universal Laws of Virality (Tested Across 4 Platforms)]]>https://www.andrew.today/p/how-to-engineer-viralityhttps://www.andrew.today/p/how-to-engineer-viralityThu, 19 Feb 2026 14:33:13 GMT👋 Hey, it’s Andrew.

Two weeks ago, I posted about starting my ‘TechTok’ journey. Well, we’re now at 3 million views and 25,000 followers. It’s been a wild ride.

Today’s article is about exactly that. If you want to build your social media following in 2026, this is for you.

Beyond that, many of the founders in my network are going to South by Southwest this year. If you’re a founder and you’ll be around, you’re invited to my series of dinners at our private mansion.

📅 Upcoming Events

🤠 South by Southwest in Austin

How to Engineer Virality

I’ve spent years building an audience of 240,000+ people across LinkedIn, X, and email. Along the way, I developed a theory: the principles of engineering virality apply universally across all social media platforms.

I wanted to test this. So I restarted my account, and spent the last 14 days speedrunning TikTok (a platform I’d never seriously used) to see if what worked everywhere else would work there too.

I made ~50 videos in 14 days. The result:

  • 1,000 → 25,000+ followers

  • 3,000,000+ total views

  • 200,000+ likes, 26,000+ shares, and 55,000+ profile views

  • 36% of my videos have 10,000+ views; one video hit 2,500,000+ views

The thesis held. Though there are nuances to each platform, the core principles of engineering virality are universal.

I hate gatekeeping, so here it is: full transparency on my method. If you want to build your social media audience in 2026, this might be the most valuable thing you read all year.

(Btw, if this was helpful and you’d like to see part two, please hit reply to let me know)

1. Curate your media diet ruthlessly

This is important and often overlooked. I'm not a full-time content creator (I spend my time running two companies), yet I produce over 60 pieces of content each week across TikTok, X, LinkedIn, and email. The reason it feels easy and frictionless is that I consistently read and consume curated, high-quality content.

Curate your feed and inbox well, and you'll create an engine that produces infinite content. The downside: you can never turn your brain off.

2. Always appeal to self-interest

Billions of people scroll daily to learn and be entertained. The only thing that will stop their scroll is if they believe a piece of content will (a) entertain them or (b) teach them something that may materially impact their life.

If you take the second path (I did), appeal to their most human desires: making/saving money, finding love, improving their health, or increasing status.

3. Leverage borrowed credibility until you build your own

When you first start on a new platform, you have zero credibility. You have to find ways to borrow it.

Cite and collaborate with credible sources: the news, academic institutions, and influential subject matter experts. Do this until you build your own credibility. Tim Ferriss used this approach to build his podcast. He called himself a 'curious beginner' until years later, he became an expert himself.

4. Master the hook (you have 3 seconds)

Everyone talks about the importance of the hook. Let me explain it in simple terms.

Think of your hook as a headline that stops the scroll. On LinkedIn, it’s the first sentence. On TikTok, the first 3 seconds. On YouTube, the title and thumbnail.

Do not underestimate this. Pros spend hours and dozens of iterations refining their hook until it’s perfect.

Your hook needs to be scroll-stopping, distinct, and emotionally charged. Aim to drive an emotional response in your viewer.

The way you package your content is just as important as the content itself.

5. Embrace the slippery slope

Your first sentence (hook) reels the viewer in. Your second sentence pulls them to the third. The third pushes them to the fourth. And so on.

The more they read, the more they’ll keep reading. Each sentence earns you the right to deliver the next one.

Think of your content like a slippery slope – once they start sliding, they can’t stop. This works for text and video.

6. Optimize for discussability

Social media platforms prioritize content that gets more user engagement. The clearest example: people debating in your comments.

Platforms reward engagement because it results in more time spent on the platform and increased monetization opportunities. Debate = distribution.

You can optimize for this by taking a strong stance and removing nuance. This might make you uncomfortable, but you can always discuss the nuance later in your content.

The content that performs best says what others are thinking but are afraid to say.

7. Study platform incentives and play by their rules

If you behave like a ‘good’ user, you will be rewarded with engagement and priority in the feed. Every platform has its nuances: LinkedIn is pushing video, TikTok has content gaps, X/Twitter favors vertical niches.

All my professional content creator friends (500k+) stay closely networked with the TikTok, LinkedIn, and Instagram creator teams to get product updates. This was new to me, but I went to my first LinkedIn creator event the other day and was immediately connected with a ‘creator manager’ who offered to help troubleshoot.

One thing that’s universal across all platforms: be the ‘reply guy.’ Don’t just broadcast your content, engage with others too.

8. Play different games at different stages

The method to the madness differs for 0→10k followers, 10k→100k, and 100k→1m. Each stage requires a new way of playing the game.

What works at 0 followers (high volume, testing hooks, riding trends) doesn’t work at 100k (deeper insights, consistent voice, community engagement).

Continue to learn and adapt as your audience grows. Don’t get stuck playing the same game over and over again.

9. Be remarkable (purple cow)

Lastly, it’s a common mistake for new content creators to over-index on tactical gimmicks, like trending music and overused hooks. These might get you short-term views, but they won’t build a lasting audience.

If I were to give you one tip, it’s this: optimize for sharing ideas that are truly valuable, unique, and remarkable. The tactics matter, but remarkable ideas matter more.

Read the best writers in your space. Study the greats who came before you. Have a pulse on culture and the topics that resonate with your community. Understand what makes content stick … it’s rarely the hook alone.

In a world of AI-generated content and endless copycats, being remarkable is the only sustainable advantage.

My final advice: Ship volume and bet on video

I wish you the best of luck on your content creation journey. If this resonated and you’d like to read part two, hit reply and let me know.

Why TikTok, some might ask? Well, given where AI is heading, I believe that ‘verified’ forms of human will matter more than ever. As text-first platforms like LinkedIn become increasingly dominated by AI slop, I’m more bullish than ever on short-form video … it’s been my #1 priority this year.

Personal brand and audience will matter more in an AI-first world. More on that next time. And remember: volume negates luck.

Lastly, thanks to my creator friends: Jonathan, Nicole, Rickie, Austin, Colin, Jason, and Iqram, who have inspired and taught me something along the way.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Why Everything is Becoming a Game by Gurwinder – From fitness streaks to follower counts, more of life now runs on points, rankings, and feedback loops. Gurwinder explains how platforms turn behavior into scoreboards, and how we slowly start optimizing for the metric instead of the meaning.

Taste for Makers by Paul Graham – PG argues that great builders aren’t technical but have taste, and taste isn’t random. Great taste across different disciplines converges on the same qualities like simplicity, timelessness, and utility

Dreams of Stability by Anu Atluru – Tech used to reward risk-taking. Now people chase safety at the top AI research labs, big companies, and even VC backing, because the middle is disappearing, and skills are getting cheaper.

Build Your Own Lore by Cameron Langford – I had the opportunity to get to know Cameron. She is a comms expert who helped take Palantir public, and here she talks about how to build your own lore. Great read if you are a founder or CEO on a big mission.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a validation sprint with Forum Ventures’ Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. Apply here.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 🧮 Need a CPA? I’ll introduce you to Alex, who I’ve been working with for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🤖 Winner AI is an AI-driven hiring engine built for fast-scaling startups, combining advanced machine intelligence with human experts to deliver top technical talent with speed and precision. Learn more.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

]]><![CDATA[Read This if You’re Young and Ambitious]]>https://www.andrew.today/p/read-this-if-youre-young-and-ambitioushttps://www.andrew.today/p/read-this-if-youre-young-and-ambitiousMon, 09 Feb 2026 16:33:58 GMT👋 Hey, it’s Andrew.

Sorry for the hiatus. I took a short break from writing – I’ve been busy launching our new business, The Shortlist, planning for SXSW (see below), and sharing my unfiltered takes on TechTok, like this one: “Do this to be rich in your 20s.”

Today's piece was inspired by a recent conversation with a new grad who asked me, "How should I think about my career?"

📅 Upcoming Events

What I would’ve told myself at 18

When I started my career, so many things held me back and kept me running in a hamster wheel. Some were small and silly. Others were existential and took me years to figure out.

But if I could go back in time, these are all the things I would’ve told myself at 18:

Stop asking “Is it true?” Start asking “Is it useful?”

A limiting belief is a story you tell yourself that holds you back - and you accept it as truth.

I’m not smart enough.

I’ll never be successful.

I don’t have enough experience.

I’m not the type of person who accomplishes big things.

I have them. Your role models have them. We all have them. They exist to protect you, but they’re not helpful. The key is not to ignore them but to say “Yes… and.” Yes, this might be true, and I’ll do it anyway. Then do the thing, prove yourself wrong, and those limiting beliefs won’t feel true anymore. Competence breeds confidence. Do it enough, and the little voice goes away, and your perception of the ‘truth’ will completely change.

Do you want to sound smart or be rich?

I had a college roommate who seemed to know everything. He was smart, well-read, but also deeply skeptical and judgmental. Every time I shared a new idea with him, he would shoot it down.

“This will never work because of X.”

And yes, he might’ve been right, and that made him sound smart.

But with that state of mind, he never took a swing at anything. Never took a risk. Because if you’re conventionally smart, you’ll always make the rational decision. Risk vs. reward. But chasing your dreams and pursuing the path with asymmetric upside is never rational. They’re emotional decisions that come from the heart.

If you want to be rich in the long run, you’ll have to forgo looking smart in the short run.

Never make decisions from a position of fear

Every bad decision I’ve ever made has been from a position of zero leverage.

My advice: If you recognize that you’re fearful, don’t make big decisions until you’re grounded.

Examples:

  • Picking a business partner because you don’t believe in your ability to do it alone.

  • Pricing yourself lower because you don’t believe you’re worth more.

  • Not asking for a higher salary because you don’t think you can get another job.

  • Choosing to be in a relationship because you don’t believe anyone else can love you (deep, I know).

Like sharks circling blood, people will smell your fear and take advantage. Recruiters, CEOs, investors, and dating partners.

Instead, make decisions from a position of power. How? Create abundance for yourself. Build yourself up to the point that nobody (not even you) can deny the value you bring. Be so good they can’t ignore you.

Don’t surround yourself with people with small ambitions

If you want to be extraordinary, you need to be around extraordinary people. The people around you set the standard for what’s possible.

When I lived in a smaller city, it was unheard of to start your own business. It was even more unheard of to scale your own business to millions in revenue. And it wasn’t until I moved to New York that I realized building a million-dollar business was the baseline for what some people achieve as hyper-ambitious. If what I said sounds absurd, then you should move to New York or San Francisco to experience it.

But I don’t mean to suggest you should ditch your day ones and leave home because your kindergarten buddy doesn’t aspire to be a billionaire. I mean to apply this to your professional network – the people you spend your working hours with.

Spend 20% of your time working toward the future

The most critical piece of advice I received when starting my business was to spend time working on the business, not just in it. This applies to careers, too.

Occasionally, lift your head up and allocate 20% of your time to thinking about the future. Some call this ‘personal R&D.’ Spend a day a week trying new things with no immediate return. That might be:

  • Tinkering with AI

  • Learning a new skill

  • Speaking on a stage

  • Expanding your network with people outside your existing community

Google once coined the 20% rule: Employees are to spend 20% of their time working on innovative, self-directed projects. The intended impact was for employees to be more creative, innovative, and to think about the future. The result led to the invention of Gmail and Google Ads.

Change your environment to increase value

We’re all familiar with the adage: A bottle of water costs $2 in the city but is priceless in the desert. Sometimes all you need to do is change your environment to increase your relative value.

I know people who are too ambitious for their own good to succeed at large corporations. They are seen as unpredictable, volatile, and difficult to manage. But this is the exact type of person to thrive in a startup environment. They’re described as: high-agency, proactive, hustler – night and day, from their relative reputation at a corporation.

It’s far easier to change your environment than to change yourself. It took me years working at large corporations to realize I was in an environment that limited my potential.

Soft skills are the new hard skills

If I had to give blanket advice to all young, ambitious people across all career paths, it would be this: work on your communication skills – your speaking, writing, and capacity to build relationships with others.

Working on these skills will give you the best bang for your buck in your career. And I believe this will be even more valuable as future generations spend more time behind screens.

Excellence comes in different forms

Form an image of a great salesperson in your head. What are they like? My guess is a charismatic, social person with slicked-back hair, a firm handshake, and well-dressed with a smile on their face. This is a common image. Strangely enough, the best salesperson I know is quiet, empathetic, an amazing listener, careful with words, doesn’t talk too much, but when she does, she sounds incredibly elegant.

Excellence can take many forms. Just because you don’t fit the traditional mold doesn’t mean you can’t be great. In fact, the greats break all stereotypes and create a category of their own.

Play the internet lottery

Third doors exist as shortcuts that give people a shot if they’re willing to risk looking silly and do something unconventional.

Playing the internet lottery is one of them. Social media has only been around for the last two decades and, as a viable income stream, for the last decade. Yet, so many career paths and tens of billions of dollars of economic value have been created by this new internet economy.

If you post on LinkedIn, YouTube, or TikTok weekly, that’s 52 chances a year to go viral, get clients, make money, get your dream job, or meet someone who might change your life. Yet the number one obstacle stopping most people from posting is the fear of looking cringe. Mr Beast posted 100–200 videos before anybody noticed him.

Everything is cringe until it works.

(This thesis is largely why I’ve been so active on TikTok)

Delusional optimism beats rational pessimism

In college, we learned about the efficient markets hypothesis.

The technical definition: Financial markets fully reflect all available information in asset prices, making it impossible to outperform the market using known information.

My interpretation: Everything in the world that can be done is done. There are no opportunities to create value because the markets are perfectly efficient.

For years, I avoided doing anything entrepreneurial because I believed everything in the world was already optimized to perfection, but this was a counterproductive and low-agency way of thinking. It wasn’t until I dispelled this belief that I started building and tinkering. I’m not a finance expert, so I don’t know if it’s actually true. But I do believe in delusional optimism when going after opportunities.

Finally, your problems will never disappear; you just get better problems

I have the same number of problems today running multiple companies (including a 7-figure company) as I did 10 years ago when I was making $45,000/year at a large company.

But my problems today are much more fulfilling to solve.

I used to think that with more success, your problems would disappear. That’s not true. You just get a different set of problems. Your level of stress will always expand. Translation: You will always be stressed about one thing or another.

The goal is not to eliminate your problems, but to find better ones.

🤠 Are you going to Austin for SXSW?

We’re back at South by Southwest from March 12–15 for our fourth year in a row. Once again, we’re hosting our iconic secret garden party and a series of founder dinners in our private mansion.

Events I’m hosting

Resources

Get involved!

  • 🤝 I’m looking for FOUR young, ambitious people to shadow my team and help us with our March 14 party. I'll teach you everything I know, pay you for your time, invite you to our private mansion, and take you to lunch (what's the best bbq in Austin?). Please comment here if interested.

  • 🙋 Apply to volunteer to join the A-team and help with our secret garden party on March 14.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Happy Ambition by Ben Casnocha – What’s the deeper reason why successful and wealthy people continue to sacrifice happiness for more money and achievement? Ben has a great take here.

In-Person Conversation Skills by Ben Casnocha – Soft skills are new hard skills, and with future generations spending more time behind screens, I’m afraid we’ll lose conversation as an artform. A useful refresher.

The 20 Greatest Decluttering Tips of All Time by No Sidebar – I hate clutter. I can’t work if my place isn’t clean, I can’t think if things aren’t in order, and I’m constantly optimizing for less. I subscribe to the belief that things can own you instead of the other way around. If you’re anything like me, you have to read this.

A Few Things I’m Pretty Sure About by Morgan Housel – Morgan just released his new book, so I’ve gone down a rabbit hole on this old stuff. He has some gems there, including this piece on life advice.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a validation sprint with Forum Ventures’ Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. Apply here.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 🧮 Need a CPA? I’ll introduce you to Alex, who I’ve been working with for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

A few weeks ago, I launched The Shortlist, our new events and media company centered around hiring. We want to build the number one hiring event in New York: the place where breakout startups go to hire, and top talent goes to find their next opportunity.

Since then, we’ve hosted our first Founder Showcase with over 200 applications and six incredible CEOs on stage (see the recap here). Also, wow - this is my favorite video by far.

We also produced a print magazine, led by Maks on my team, and are now planning our next showcase on February 23.

One thing I’ve reflected on is how much I love the 0→1 of building a brand from scratch. Ideating, creating the concept, designing it, putting the team together, bringing it to life - and then seeing it manifest in the real world. It’s incredibly fulfilling. I haven’t felt energy like this since starting my mixers five years ago.

It’s a reminder to keep something in your life at the 0→1 stage. It might be a business, a hobby, or a new skill. We need something that brings back the childhood wonder of creating something new.

The 6 incredible CEOs who presented at our January 27th showcase.
Hosted at betaworks, a legendary accelerator in NYC tech.
Mina (ex-Meta) demos his new AI device.
]]><![CDATA[Introducing The Shortlist New York]]>https://www.andrew.today/p/introducing-the-shortlist-new-yorkhttps://www.andrew.today/p/introducing-the-shortlist-new-yorkTue, 06 Jan 2026 15:32:07 GMT👋 Hey, it’s Andrew.

Happy New Year! I’m excited to share my newest project with you today. Keep reading below.

📅 Upcoming Events

After spending the last few years hosting 200+ events across NYC, SF, and Austin, and connecting founders with talent, I kept seeing the same problem:

The best startup opportunities never make it to job boards.

By the time a company is “hiring publicly,” the founding team is already set. The early equity is allocated. The people who built the product, the processes, and the culture got in because someone made an intro before the headlines.

Meanwhile, I know so many incredible second and third-time founders who are building again. People who have succeeded massively before and are now working on their next thing.

And yet nobody knows about them.

So I’m launching The Shortlist New York - a monthly event series and newsletter connecting ambitious talent with breakout founders in NYC.

How it works

Monthly Founder Showcases

Every month, we host an event where six founders take the stage to tell you what they’re building and why you should join them. This is a carefully curated lineup of vetted founders and CEOs building companies I believe will explode in the coming months.

We’ll invite ~50 of the top engineers, designers, and GTM operators (sales, growth, marketing) to meet them. Free to attend, but application-only. Our first event is on January 27 - apply here.

Bi-weekly Newsletter

Between events, you’ll get a newsletter featuring under-the-radar job opportunities at seed through Series C companies, founder spotlights, and curated events worth attending in the NYC ecosystem. Subscribe here.

Our north star metric: Hires made following the event.

Who is this for?

This is for ambitious engineers, designers, and GTM operators who are:

  • Looking to join the next unicorn before it’s obvious

  • Currently at a big tech company or mid-stage startup, wondering what’s next

  • Ready to join something earlier where equity and ownership matter

  • Looking to meet founders before everyone else figures out they’re the next big thing

My goal is to make this the best in-person event for startup hiring in NYC.

I’ve spent years building community in tech. I’ve seen what works and what doesn’t. This is the event I wish had existed when I was exploring my next move.

Why should you attend?

You’ll meet founders before everyone else does

These are second and third-time founders who are 6-12 months away from their breakthrough moment. You’re getting introduced before the hype, which means better roles, more equity, and influence over product decisions. And you’ll hear directly from the founders and CEOs of these companies.

Curation is our single most important factor

You’re not one of a thousand people, but one of 50. The person sitting next to you might be a senior engineer at Google exploring their next move. The person across from you just left a Series C startup to go earlier. These are your peers, and the connections you’ll make in this room are just as valuable as the pitches.

It won’t be boring

After sitting through dozens of corporate speaker events, I know exactly what not to do. This will be casual and fun, hosted in a cool venue with some music and food… somewhere you actually want to spend your Tuesday night.

Get involved

  • Attend our first showcase → January 27. Limited spots, application-only.

  • Join our talent network → Tell us what you’re looking for. We’ll connect you with companies that match before roles go public.

  • Founders: Apply to pitch → Hiring for key roles? We want to feature you.

  • Subscribe to the newsletter → Get jobs, founder spotlights, and events delivered bi-weekly.

  • Follow along: LinkedIn / Instagram / Twitter

A quick note: I’m lucky to be building this with Ivor Stratford and our marketing associate Sangavi. A big thank you to our Fibe team: Jacob, Maks, Danielle, Anna, Anya, Vitoria, and our branding consultant, Jamie Dong, who led our full design sprint and created the brand from scratch.

See you on January 27th.

– Andrew

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Marketing Ideas – One of my favorite newsletters. It's written by my friend Tom Orbach, who runs growth at Wiz (the $32B cybersecurity company). Every Thursday he breaks down one tactic that's actually working right now. No fluff, just marketing ideas you can steal. 60,000+ marketers subscribe.

Standing Out in 2026 – Lulu Cheng Meservey might be the best in the world at what she does: comms and personal branding. Here she drops a masterpiece on why 2026 is the year of doing real things

37 Pieces of Career Advice I Wish I’d Known Earlier – Ryan Holiday is one of my earliest inspirations. at 15, he was working at a small deli and grocery store. Shortly after, he was the director of marketing for a publicly traded company. He’s also been a research assistant to an author, an analyst at a talent agency, an entrepreneur, a freelancer, a speaker, and an author himself. His advice for building a career.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise capital in 2026. Fill this out.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

]]><![CDATA[11 Predictions for 2026 & Beyond]]>https://www.andrew.today/p/11-predictions-for-2026-and-beyondhttps://www.andrew.today/p/11-predictions-for-2026-and-beyondFri, 02 Jan 2026 14:24:54 GMT👋 Hey, it’s Andrew.

2025 was a remarkable year for us. We grew the team, took on new partners, grew our audience meaningfully, surpassed last year’s revenue, I invested in 10 companies, and most importantly … it was significantly more fun.

I’ve been working on a few new developments over the last few weeks, including over the break, that I’m excited to share soon. Stay tuned. Meanwhile, here’s some ideas I’d like to share to kick off the year.

📅 Upcoming Events

What should we expect in 2026 and beyond?

These predictions come from observation - from conversations with founders and investors in my network, and from studying people far more visionary than me. Most relate to our changing workforce, evolving consumer behavior, and how we work together.

Here we go:

1. The college replacement economy will go mainstream.

An entire generation missed out on the traditional college experience in favor of a digitized version from 2020 to 2023. This, along with the loneliness epidemic and the declining alcohol consumption and socializing among young adults, has resulted in the emergence of an entirely new leisure and nightlife category centered around intellectual stimulation and curated connection. See communities like Lectures on Tap, where people gather to listen to university professors at bars and meet other curious people. This extends beyond nightlife: as this cohort ages, expect to see membership communities and IRL learning experiences to become as common as happy hours once were.

2. Healthspan and lifespan metrics will become status symbols.

The convergence of wearables, gamified biometrics, healthcare influencers, and accessible preventative care is creating a new dynamic. We’re still extraordinarily early, but within a few years, I wouldn’t be surprised to see elite gyms or clubs with minimum resting heart rate or LDL requirements - health credentials as gatekeepers, similar to how communities like Long Angle use net worth thresholds. Combining the increasing influence of creators like Bryan Johnson, who normalize longevity optimization, and our human desire to signal our advantages, you get health metrics as a new form of currency. My bet: Google search interest for specific metrics like “biological age test” doubles year over year.

3. AI will widen the gap between high and low agency individuals.

Even among my personal network, I’ve seen massive differences with how people use AI. High agency people treat AI as an extension of their existing capabilities, using it to augment judgment and improve execution, while low agency people will use it as a substitute for critical thinking and judgment, outsourcing the capabilities that make us human. A specific scenario: the former will develop filters for credible information while the latter will fall prey to deepfakes and synthetic content.

This won’t be technology’s fault. You’ll start seeing articles with headlines like “AI is Making Us Dumber,” but the truth is more nuanced: AI is a mirror that amplifies our existing relationship with agency. The challenge today is that this gap accelerates faster than previous technology shifts because the feedback loops are shorter and the stakes are higher. Gone are the days of the 10X employee; we’ll start to see the 100X employee instead.

4. Physical is sexy again.

Colossus magazine, J.Crew’s revived print catalog, Palantir’s merch brand, Complex bringing back print, Duolingo’s pop-up stores, Microsoft and Costco launching magazines, Meta investing in physical retail for their glasses … notice a pattern? As digital experiences become infinitely commoditized, brands are rediscovering the value of physical goods and analog experiences as their differentiating factor. I’ve written before about the “Head of IRL” role emerging in early-stage companies - soon, every brand will build IRL capabilities as a differentiator. The pendulum is swinging back, not because digital failed, but it succeeded to the point that scarcity now lives in the physical world.

Colossus is a media company about business and investing.

5. Multi-hyphenate careers will emerge as a viable career path.

The “side hustle” era is ending and evolving into something more substantial: knowledge workers building multiple income streams across their personal portfolio, enabled by AI tools. As the creator economy matures, it will professionalize as a career path that will be taught in schools. When AI removes the friction of building and shipping media and software, the multi-hyphenate model becomes accessible to more than just the exceptionally driven. I believe in 2026 and onward, we’ll see measurable increase in people earning over 50 percent of income from multiple sources.

6. Soft skills will become the new hard skills.

Throughout history, the most valuable skills have been those that are simultaneously scarce and in demand. In the 2000s: computer science and software engineering. The 1980s: management and finance, fueling the MBA boom. Before that: hard sciences - engineering, math, physics. Now, as people spend more time behind screens, we’re forgetting how to influence, sell, and lead in person. The principles in “How to Win Friends and Influence People” will become a forgotten art, and charisma will be the new unicorn skill. What does this imply? Well for one, we’ll start to see the reversal of Zoom interviews from the remote era back in in-person to evaluate for interpersonal skills.

7. Taste becomes the last defensible moat.

In a world where AI can build features and paid ads can buy attention, what’s left to differentiate? Taste, craft, design. Design used to be downstream of business decisions - a “nice to have” when budgets allowed. Today, designers have a seat at the strategy table because in a world of commoditized software products that all serve the same purpose, ‘brand’ will stand out. The future 10X marketer will be equally skilled in design, branding, writing, and community building.

8. The era of user-generated software begins.

We’re crossing a threshold where building software no longer feels like engineering, but authoring. As vibe coding becomes exponentially better, we’ll be able to build and share tiny apps, automations, and personal dashboards as easily as we can share posts today. Imagine sharing your habit-tracking app with your partner the way you’d share a playlist. Marketplaces will emerge, allowing software to be created quickly, personalized deeply, and shared socially. The implications are massive: if software becomes as easy to create as content, the line between “creator” and “developer” disappears entirely.

9. The first explicitly anti-AI social network will emerge.

No AI-generated posts, no bots, no synthetic engagement, and proof-of-person required. People are already revolting against AI ‘slop’ - studies show that 20%+ of videos recommended to brand new YouTube users qualify as low-quality synthetic content. The dead internet theory may become a self-fulfilling prophecy unless new platforms are created that explicitly reject it. This will be a response to a real need for authentic human connection in a world dominated by fake content. My belief is that in 2026 we’ll see a new social network with 1M+ users without relying on algorithmic feeds.

10. Alternative education models will resurge to meet the AI skills gap.

We’ll see the return of General Assembly-style programs: in-person, cohort-based learning for new-age tech skills. This happens when traditional gatekeepers can’t meet exponentially increasing demand. Previously, coding bootcamps emerged when Ivy League CS programs couldn’t serve the whole market. Today, the new valuable skillset - vibe coding, product design, AI-augmented distribution - will soon be packaged, programmatized and offered to ambitious employees and aspiring entrepreneurs.

11. Independent media will dominate the information landscape.

The most influential tech media in 2025 - publishers like TBPN and Newcomer - were created in just the last few years. When information is abundant and increasingly synthetic, we defer to people we trust, not brands. Going direct is the antidote to AI noise, and I expect more journalists, operators, and domain experts to build their own media properties (and events companies) rather than work within established institutions.

Jordi and John from TBPN.

What ties all of this together?

If you look closely, you’ll see a pattern. Every prediction is related to another. User-generated software empowers multi-hyphenate careers. Physical experiences create communities that improve our ability to connect with others, be happier, and (hopefully) live longer. Alternative education produces high agency people who use AI more responsibly.

I’m more optimistic than ever about the opportunity to use this technology shift to create more fulfilling work and build deeper relationships.

2026 will be extraordinary. Let's make it happen.

👋 Get Involved

  • If you’re hiring, we can get you in front of 50,000+ founders, operators, and builders. Apply here.

  • If you’re looking for your next opportunity, we’ll connect you with breakout startups that are actually going places. Apply here.

  • CMOs and marketing leaders, if you want early access to our events, apply here.

  • And if you want to sponsor and get in front of this community, fill this out.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Sam Altman’s Method for Clear Thinking – Sam Altman, CEO of OpenAI, on his note-taking system and how he thinks about writing.

Advice for generalists who want to join startups – A brilliant how-to guide for business generalists who want to work at startups, written by Ben Lang (early at Notion, Cursor)

Random Quality Of Life Improvements That Will Change Your Life – Randomly found this gem on Twitter/X. Worth a read as you refine your 2026 goals.

Curiosity Is Compound Interest for Your Brain – Original ideas seem to be declining with the prevalence of AI. The antidote is to stay curious and form your own mental models. Here’s how you can do that.

🏢 (Sponsored) Take Part in NYC’s Largest Office Survey for Startups (And Get $20)

Hubble is NYC’s largest online platform to find startup office space.

One of the questions they get the most is about how other startups are working:

  • Are they full-time in the office? Are they fully remote?

  • Do they work hybrid? If so, how many days, and is the whole team in? What about the new 9-9-6?

To answer this question, they’re conducting NYC’s largest office survey for startups - they’d love to hear from you!

The survey takes a few minutes. Not only will you be the first to get the report when it’s done, you’ll also get $20 Amazon voucher as a token of appreciation.

👉 Fill out the survey here.

P.S. - You can check out the same report they did in London here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

]]><![CDATA[10 Questions to Ask Yourself Before 2026]]>https://www.andrew.today/p/10-questions-to-ask-yourself-beforehttps://www.andrew.today/p/10-questions-to-ask-yourself-beforeFri, 26 Dec 2025 16:17:52 GMT👋 Hey, it’s Andrew.

I want to start by saying how grateful I am for you. Thank you… for reading these emails, for showing up to our events, for trusting me with your time. Being in your inbox is a privilege I take seriously.

This is my last article of the year. I hope 2025 was significant for you - and that 2026 is even better.

📅 Upcoming Events

👋 Get Involved With Our Community

  • If you’re hiring, we can get you in front of 50,000+ founders, operators, and builders. Apply here.

  • If you’re looking for your next opportunity, we’ll connect you with breakout startups that are actually going places. Apply here.

  • CMOs and marketing leaders, if you want early access to our events, apply here.

  • And if you want to sponsor and get in front of this community, fill this out.

It’s hard to believe 2025 will be over in less than a week.

It feels like yesterday when I was doing the same annual reflection exercise, but for 2025.

The theory of time compression states that your perception of time exponentially speeds up as you age, so that at thirty, a year passes 7 times faster than it did when you were five.

One way to slow down your perception of time is to hit pause, look back, and reflect whenever you get the chance. The end of the year is always a nice moment to do that.

For the last 10 years, I’ve always done a personal annual review. It’s been a pretty life-changing exercise to help me identify patterns and make better decisions.

The process is simple and quick. Here’s what I’ve realized: most reflection processes take HOURS, and that’s too much for most people. But this one is simple. 10 questions. 5-10 mins each. Totally doable in one sitting.

How to use this:

Don’t just read these questions and move on - that’s pointless.

Block 2 hours on your calendar, go somewhere quiet, and put your phone in airplane mode. Maybe your Spotify Wrapped will jog your memory?

Then answer each question, but not in your head. Make sure to write it down.

I do this every year between Christmas and New Year’s. It’s become one of my most valuable rituals. Some questions will be harder than others. Have fun with it.

Here are the 10 questions that may change your life.

1. What were your most meaningful moments?

Write out ALL the significant moments from this year - the good, the bad, the ugly. This serves as your starting point for everything else to come. If you do it right, you should have anywhere from 5 to 20 moments to reflect on.

If it helps, look through your photo album, calendar or journal. I find it helpful to list out moments in these categories: Personal, Work, Health, Relationships & Personal Finance.

I actually keep a rolling list throughout the year - something my first mentor taught me. When something happens, I write it down immediately.

For me:

  • Taking my family on vacation to Portugal

  • Speaking in front of 600+ people in Greece

  • Visiting home in Hong Kong after a decade abroad to say goodbye to my grandmother

My keynote on the power of community building in Athens, Greece

2. What are you proud of?

If you’re anything like me, you immediately move on to the next thing after hitting a big goal. Stop doing that. Instead, acknowledge it, pat yourself on the back. You deserve it.

As a classic, type A ‘achievement’ chaser, I’ve gone down this path many times and learned that life starts to feel pointless if you’re just collecting wins.

Instead, slow down to reflect on it, and WRITE DOWN the things you were most proud of this year.

I’m proud that all our employees stayed throughout the entire year, no matter how hard it was. Half our team has been with us since the start two years ago, and the other half has been with us for over a year. They’re excellent at what they do and have options, and I’m grateful they chose to stay with us.

Our Fibe team at the end of 2025. Our team: Jacob (Partnerships), Danielle (Events), Sangavi (Marketing), Maks (Operations), and Vitoria, Anna, Anya, and Akash (Fellows). Also featured: Bailey, CEO of Cal.com - our friend at Fibe!

3. What were the biggest challenges you faced?

What was hard this year? These are the things that kept you up at night. And it’s totally okay if you haven’t solved them yet.

The point isn’t to dwell, but to understand - and be honest - about the thorns in your life right now. I’m also a big believer that if you hold a problem long enough in your head, your subconscious will eventually come up with solutions.

For me, it was dealing with shiny object syndrome. It’s hard to stick with building something like events when literally everyone around you is building AI and asking you when you will too. But I stuck with it - and now I’m more bullish than ever.

4. Which of your strengths has best served you?

I’ve learned that most people assume they’re average at everything, but that’s not true.

Over the course of my decade-long career, EVERYONE I’ve worked with excels at at least one skill - or has a unique combination of 2-3 skills they’re really good at.

It wasn’t until I left Google that I realized my biggest strength was ‘organizing chaos.’ No matter how complex a problem was, I could put a structure in place to help my team solve the problem. Even in the complexity of startup land.

5. What did you avoid because of fear?

Sometimes fear disguises itself as ‘being realistic’ or ‘waiting for the right time’. Your ego will seldom admit that you’re scared.

This question forces you to be honest about what you didn’t do and why. Write it down. Then ask yourself if the fear was justified or if you just chickened out.

There are dozens of people I’ve admired and wanted to meet. But I avoided reaching out to them because I didn’t know how to add any value. It’s probably one of my limiting beliefs, but next year, I won’t think twice about sending them a note. I like this quote: Move in the direction of your fear, and the death of it is certain.

Interviewing Sahil Bloom on stage in front of 800 people (someone I’ve admired for a long time)

6. What created energy this year? What drained energy?

Nobody can sustain doing something for long periods of time if it drains them. And it’s never productive to try.

The smarter way to approach it is to identify the activities that drain you early on.

For this question, make two lists. One for things that gave you energy (certain projects, specific people, activities). One for things that drained you (meetings that went nowhere, toxic relationships, obligations you hate).

Then do more of column A and less of column B in 2026.

For me: I’m energized when I meet weird, quirky, and contrarian people who are up to extraordinary things. Drained when I spend time with people who are single-dimensional, overly transactional, and uninspired. Two sides of the same coin.

Our co-hosted dinner with Henrik Werdelin, founder of BARK (BarkBox), Audos, Prehype for a group of 10 entrepreneurs.

7. What will you bring with you into the new year?

Not everything from 2025 should come with you, and this question helps you identify what’s worth keeping. Think through the habits, relationships, and mindsets that served you. If something helped you in 2025, make sure it’s part of your 2026 plan.

My goal this year was to see my parents four times (read: The Tail End), no excuses - and I did exactly that. I took them to Portugal, invited them to New York, and joined them in Hong Kong and Toronto. It’s the most time I’ve ever spent with them post-college, and something I want to continue doing for the decades to come.

I love these guys

8. What will you leave behind?

The other side of question 7. What needs to stay in 2025? Bad habits, toxic people, obligations that don’t serve you anymore, self-limiting beliefs. Write them down. Maybe even on a piece of paper, then burn the paper. You’re not bringing this stuff into the new year.

My realization: My calendar this year was an absolute mess, and next year I want to be more ruthless with how I manage my time. I was perhaps a little too generous with my time, said ‘yes’ to too much, and need to cut back.

9. What are you excited about?

You don’t need to ‘reflect’ too much on this one; it should be immediately clear.

If not, that’s a different issue (you should participate in more things that genuinely excite you)

Maybe it’s a new business idea. Maybe it’s finally getting healthy. Maybe it’s something totally different from what excited you 12 months ago. Whatever it is, pay attention. Your excitement is a clear indicator of where you should spend your time.

Mine: We’re launching a few new projects next year that I’m pumped about. More to come soon.

10. What is one moonshot goal you have for next year?

At Google, we had an entire department called Moonshots dedicated to working on the delusionally optimistic, but unrealistic ideas that, if successful, would have extraordinary positive impacts.

You should have a moonshot, too - a goal that, if accomplished, would change everything for you.

For the last few years, I’ve been thinking about starting a new project beyond events, beyond media, beyond community. It would involve me investing a significant amount of my personal capital and time, but the outcome, if successful, would be asymmetrically enormous. I hope to have an action plan together by Fall 2026.

Take Action

I’ve done this exercise every year for the last decade, and it’s frankly changed my life.

Some years, the answers surprise me. Other years, they confirm what I already knew but was afraid to admit. Either way, it works.

If you want to get even more out of it, do it with a small group. Go through it individually, then get together and share your answers to come up with a plan to keep each other accountable.

This is how you prepare for 2026 to be the best year of your life.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Steam, Steel, and Infinite Minds – A short essay on the history of ‘innovation’, where we are in the AI cycle, and what the future might look like by Notion CEO, Ivan Zhao.

So What’s Going to Happen to Product Management Anyway? – A valuable read for those working in PM - esp. if you want to see where the puck is going. With AI, ‘Product Management’ as we know it may be one of the functional areas that will transform the most over the next decade.

How to be Legitimate – ‘Kingmaking’ and the hidden art of building credibility and influence from the lens of Venture Capital and Silicon Valley.

Flounder Mode – A profile on Kevin Kelly (Co-founder of WIRED magazine, author, advisor to Steven Spielberg, polymath community-builder, artist, athlete) on how to follow your curiosity and build a multi-hyphenate career. Naval Ravikant called him the modern-day Socrates.

🏢 (Sponsored) Take Part in NYC’s Largest Office Survey for Startups (And Get $20)

Hubble is NYC’s largest online platform to find startup office space.

One of the questions they get the most is about how other startups are working:

  • Are they full-time in the office? Are they fully remote?

  • Do they work hybrid? If so, how many days, and is the whole team in? What about the new 9-9-6?

To answer this question, they’re conducting NYC’s largest office survey for startups - they’d love to hear from you!

The survey takes a few minutes. Not only will you be the first to get the report when it’s done, you’ll also get $20 Amazon voucher as a token of appreciation.

👉 Fill out the survey here.

P.S. - You can check out the same report they did in London here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

I went to a different kind of event the other day - a meetup for Alaskan Klee Kai dogs and their owners.

Most fun and hilariously cute thing I’ve done in a while..

It was hosted in the beautiful Madison Square Park - my favorite landmarks in NYC. The history is fascinating btw: the stunning park we see today used to be a swampland, before turning into a refuge for juvenile delinquents. It wasn’t until the 2000s that Danny Meyer (Founder of Shake Shack, Eleven Madison Avenue, Union Square Cafe) raised money to transform it into what it is now - and built New York’s best restaurants around it. Thanks Danny.

P.S. If you have a young dog in the area, Jasper is always looking for new friends.

Spot the difference
]]><![CDATA[Two Years After Leaving Google: The Truth About Entrepreneurship]]>https://www.andrew.today/p/two-years-after-leaving-google-thehttps://www.andrew.today/p/two-years-after-leaving-google-theFri, 05 Dec 2025 16:23:35 GMT👋 Hey, it’s Andrew.

This is one of the last articles I’ll publish this year, and probably the most honest one I’ve written. I put everything into this because I think people rarely share the lows - they only share the wins, which makes entrepreneurship seem easier than it actually is.

If you’re earlier in this journey than me and this helps you feel less alone, then writing this was worth it.

📅 Upcoming Events

Two years ago, I left my dream job at Google. Today, I’m more fulfilled than ever - and more uncertain than I’ve ever been.

I’ve hosted over 200 events, written hundreds of articles, and invested over $100,000 of my own money into projects. Some days I feel unstoppable. Other days I don’t want to leave the house.

My first year was messy. I was constantly uncertain and directionless - I’m the first person in my family to start a business, the first to work in America, and one of the few in my graduating class to take this path.

On Sunday, I sat down at a restaurant alone and wrote down the truths nobody tells you about entrepreneurship:

I had no clue what I was doing.

At first, I had no idea what I was doing. I felt this way for the first year. What is this business I was building? Am I a creator? An event planner? A media entrepreneur? Who’s someone who’s had success doing it this way before?

Some days I’d wake up and genuinely have no idea what to do. No manager to tell me. No roadmap to follow.

But over time I realized I needed three types of people around me:

  • Believers - people who believe in you, even when you don’t. They’re the types of people who make you feel like you can run through walls after spending time with them.

  • Guides - people who teach you specific skills and show you the way. They give you the map when you’re lost.

  • Proof - people who inspire you with their grit and perseverance. They make you believe that because they did it, you can too.

I wish I’d figured this out in month one instead of month twelve.

I became delusionally ambitious.

Because I’ve had a little success, I stopped seeing the world through constraints, but instead through opportunity. Once you prove to yourself that you have the capacity to do things that you once thought were impossible, you start to believe you can do anything.

Most of us are conditioned to think through limitations because when you work for someone else, there are so many things you are told you can’t do. But when you work for yourself, you only see possibilities - especially if you are young and new to the world of entrepreneurship.

I constantly found myself wondering if I could take on bigger risks, take a bigger swing. This felt dangerous, but liberating at the same time.

I couldn’t turn work off.

Work took over completely. There’s that Jensen Huang (CEO of NVIDIA) line where someone asks how many hours he works a day. He says, “All of them.”

Most entrepreneurs I know don’t have hobbies. And for the ones who do, the hobbies tend to be some sort of achievement or competition, like long-distance running or heavy lifting.

Sometimes I catch myself at a party, mid-conversation, and all I can think about is getting home to my computer to solve the problem that’s been on my mind. It became an obsession I couldn’t escape, and I started to lose interest in the stuff I used to love, like playing basketball, going to concerts, and reading books that aren’t about business. Eventually, friends started to notice and stopped inviting me to stuff. It becomes an endless loop.

I learned the love language of business.

I met more people over the last two years than in the 10 years before it because of our shared love of business. When you meet another entrepreneur, the conversation immediately jumps to ideas and opportunities. You know exactly what incentivizes each other and how to help each other. It’s easy to find your community and connect with them because you’re all marching toward the same goal - building something impactful.

But this also meant I started judging people by their ambition level. My tolerance for small talk disappeared. I became that person who turns every conversation into “what are you building?” Working on correcting this.

My relationship with money changed.

Corporate life trains you to never talk about money. Nobody discusses their salary, their savings strategy, or how they invest. I believe that this lack of transparency benefits employers - the ones who run the game - not employees. You could be getting underpaid for years without knowing it, lacking the information you need to make decisions that could change your life.

When you work for yourself, money becomes the primary language. Entrepreneurs openly discuss revenue, profit margins, tax strategies - not to show off, but to genuinely help each other. Once you accept that businesses exist to generate profit, the world starts making a lot more sense.

Last month, a founder I’d just met told me he was doing $2M ARR but only taking home $80K because of runway concerns. Nobody would’ve ever shared that at Google.

I tried optimizing everything in my life.

Nothing else mattered once I had complete clarity on my goal, and I started optimizing to maximize surface area, energy, and performance toward it.

I wanted to be healthier because more energy meant more capacity. I learned productivity systems to work smarter, not harder. I invested money to buy back time. I joined communities where I could meet people who’d accelerate my impact.

Everything that didn’t serve the mission started to feel trivial. I stopped caring about things I once obsessed over - things that, in hindsight, were completely pointless.

It’s been financially rewarding.

In corporate life, I could predict my comp 1, 3, 5 years out. I could estimate my lifetime earnings with a spreadsheet and predict the exact net worth number I was going to hit. Some people like that security, but I only saw the ceiling. It’s like playing a game where you know how it ends.

Entrepreneurship removes the ceiling. If you’re lucky and things go well, it can change your life. Your relationship with money will change completely, and every dollar spent becomes an investment with clear ROI. Your income becomes a function of your decisions.

But let me be clear, there were months when I had no idea when the next paycheck was coming from. Months where I’d check my bank account every single day to calculate how long it could last. I saw every deal as an opportunity for more time to keep playing this game of “entrepreneurship.”

My relationships became more transactional.

This is the part I’m least proud of. There are times when I’ve been the person who mentally calculates ROI while someone is still introducing themselves. ‘Can this person help me? Should I take this coffee?’ It’s disgusting, and I hate that I do it.

New York amplifies this. Everyone’s assessing everyone. But that doesn’t make it okay. Again, I’m actively trying to fix this, but the pull is so strong that sometimes I wonder if I’ve fundamentally changed as a person - and not in a good way. It takes extraordinary effort to break this pattern of thinking. Every single morning, I remind myself: ‘Remember to be kind.’ Some days it works. Some days it doesn’t.

My self-worth became tied to the business.

There are moments when I feel unstoppable - on top of the world, believing I can do anything. This happens when you speak on stage in front of a thousand people.

But these highs are always followed by extreme lows. Because I built my business around my personal brand, whenever I stop moving, I feel like a failure. When things don’t go well, I feel like the entire world is laughing at me. Some of these periods last months. Sometimes I don’t want to leave the house.

When things go well, I feel validated. When they don’t, I wonder if I have any value beyond what I’ve built. Every failed project feels like proof I’m a fraud. You take business setbacks personally in a way you never did as an employee. As an employee, a bad month didn’t mean you were worthless. As an entrepreneur with a personal brand, every failure feels existential. Every win feels like proof you deserve to exist.

It’s tough to live on that pendulum.

My perception of time changed dramatically.

I wake up excited and optimistic… Every Single Day. But the last two years felt like they went by in months. When you have tunnel vision, you lose track of how long the tunnel is. I wish I could slow time down, and the idea of killing time now feels like such a privilege.

I opened doors I didn’t know existed.

When I was in corporate, I was surrounded by people like me. The only variation in the people I met was in seniority or the types of work we did. But for the most part, we all had a similar worldview.

When I dove into the world of entrepreneurship, I started meeting all kinds of people I never knew existed.

  • 20-year-old entrepreneurs who sold their companies for tens of millions of dollars.

  • Olympic athletes at the top of their discipline.

  • Media personalities who had mastered influence.

  • Investors who make decisions every day on how to allocate their hundreds of millions of dollars.

We connected because of our shared objective - we just wanted to make it. And after a while, I realized that everybody, no matter how accomplished they are, is still trying to figure it out. Even those who’ve successfully done it before. Nobody has the answer.

I feel more alive than ever.

I used to feel stuck in a box. Now I feel like I’m playing a video game where I’ve unlocked all the levels, maps, and quests instead of being stuck in one part of the world that is rigged against me.

The thing I’m most grateful for every day is the capacity to feel an extraordinary sense of boundlessness and freedom. For the most part, I can answer to no one but myself. I can choose how I spend my time, energy, and money. At the end of the day, if I succeed or fail, it’s all up to me.

Do I miss anything about Google? Honestly, yes. I miss the instant credibility of saying where I work. I miss having a team to brainstorm with. I miss someone else handling payroll, taxes, and healthcare. I miss free lunch. But here’s what I don’t miss: asking for permission. Having a ceiling. Building someone else’s dream.

Two years in, and I finally understand what they mean when they say entrepreneurship isn’t for everyone. It’s not because it’s hard. It’s because once you taste this kind of freedom - even with all the uncertainty, the transactional relationships, the ego swings, the months where you question everything - you can’t go back to anything else.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

How to Actually Look for a Job (Without Wasting Everyone’s Time) – Auren Hoffman is the rare type of person who is always honest and direct. The best guide I’ve seen online on how to find a job.

How to Sound Like an Expert in Any AI Bubble Debate – A grounded, neutral perspective on navigating the “AI bubble” conversations that we all can’t seem to avoid.

The Anti‑AI Bet: Why Live Sports Will Become More Valuable As Everything Else Gets Cheaper – Why the next decade isn’t going to be all about AI… but in fact, quite the opposite!

“Take Control of Your Desk,” And Other Career Tips for ICs, Managers & Founders – Taking control of your career means more than just doing hard work. It means picking the right environment and finding the right people to surround yourself with.

How To Develop Good Taste, Pt. 1 – Die Workwear is the anonymous fashion guru who’s recently blown up on X for critiquing style and fashion (including one of my posts). Worth a read if you’re into style.

💼 Job Board

All the job opportunities in my network.

👉 STARTUP JOB OPPORTUNITIES: I’m creating something new to help match you with great startup job opportunities. Fill out this form to learn more (everything is completely anonymous, and your info will not be shared).

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.

  • 🚀 Building in the next year? Spend 6 weeks with the Forum Ventures’ Venture Studio team to validate your concept and get the opportunity to Pitch us for $250k and a full build team. Apply here.

  • 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

“Burn Rate” by Andy Dunn. Read it. One of the most impactful books I’ve ever touched. I’ve spent the last two years working with Andy, investing in his company, getting to know him. We just sat down in New York to record a podcast. I shared stuff I’ve never talked about publicly. My starting story. My vulnerabilities. All of it. His book did that to me. Watching him talk openly about bipolar disorder while building Bonobos gave me permission to stop hiding. The podcast drops soon. Get his book here.

]]><![CDATA[Andrew's 2025 Holiday Gift Guide]]>https://www.andrew.today/p/andrews-2025-holiday-gift-guidehttps://www.andrew.today/p/andrews-2025-holiday-gift-guideSat, 22 Nov 2025 15:43:08 GMT👋 Hey, it’s Andrew. We’re approaching my favorite time of year and the best time to be in New York. If you’re feeling festive and thankful, you might like today’s article.

📅 Upcoming Events

We only have three events remaining for the year, but we are in the process of planning our lineup of events for 2026, including stuff with fitness, sports, dinners, parties, art gallery crawls, and other socials. If you have any other ideas or want to collab, hit reply and let me know!

For the second year in a row, I’m publishing my holiday gift guide. It’s a list of products that have improved my life, brought me delight, or come highly recommended by friends.

For more ideas, check my previous gift guide from 2024 and if you see something I missed, please comment below and

*If you see an asterisk beside a product, it means I’m involved in some way - as an investor or an affiliate. That doesn’t change my recommendation. I only work with products I genuinely love!

Gadgets & Fun:

  1. Garmin Forerunner 265 – I bought one of these after seeing one of my running friends get one because I was curious. I don’t consider myself a runner, but wow, it has made me so much more diligent with my workouts and sleeping habits.

  2. Chameleon Board Game – Completely obsessed. The best game in the world for casual board game players. We play this at least once a month at our events. Perfect for people who like games with deception and role play.

  3. Anker Nano Ultra-Slim Power Bank – My go-to slim and sleek charging device for my phone. I bring this everywhere I go.

  4. Bang & Olufsen Beosound 2 – The most aesthetic speaker I’ve come across, with incredible sound quality. Definitely a conversation starter if you like hosting.

  5. TRML (OG) – A shared physical portal for families.

Style:

  1. THE DAVEK ELITE Classic Cane Umbrella – Umbrellas are fashion accessories. Why do people use cheap ones? The most stylish umbrellas I could find.

  2. Duke Chelsea Thursday Boots – I own multiple pairs of boots from this company. They’re high quality, durable, and look awesome

  3. Moshi Digits Winter Touchscreen Gloves – Perfect for winter when you need to keep your hands warm but also use your phone out in public

  4. Commie Si Merino Sock – A fancy winter sock, if you want to, in case you want to treat your feet. Keep this one away from your dog.

  5. Quince Sweaters – Affordable and high-quality sweaters with no branding. It sort of fits the “quiet luxury” vibe without the luxury price tag. My friend Parth got me one of these, and I was delighted.

Software:

  1. Wispr Flow* – I don’t type my emails or texts anymore. It feels like a waste of time. Instead, I just use Wispr Flow.

  2. MigrateMate* – When I was early in my career, it was a drag trying to find jobs that sponsored visas in America. These guys make it easy.

  3. Superpower* – I think that everyone should be doing blood work at least once a year to understand exactly what’s going on in your body. No excuse.

  4. Storyworth – I’m obsessed with this product and impressed with how simple it is. A great way to create a deeper relationship with your partner, family, or friends.

  5. Kondo* – LinkedIn DMs, but on steroids.

  6. Endel* – One of the most elegant iOS apps I’ve ever used. I use it for 2-3 hours a day to lock in and relax.

Health & Wellness:

  1. WOD Nation Adjustable Hand Grip – Apparently, every 11-pound decrease in grip strength is linked to a noticeable jump in all-cause mortality risk over the next decade. This is convenient and kind of fun!

  2. Lumie Vitamin L Lamp – An incredibly useful product as winter is coming. I use this for 30 minutes every morning and see a noticeable change in my mood and energy.

  3. Kane Revive Recovery Shoe – For runners and athletes - especially the day after a long workout.

  4. Brooklinen Super-Plush Robe – There’s nothing like relaxing in a robe after a long week.

Home:

  1. Breville Barista Express Impress – My girlfriend bought this for the home, and it’s transformed our mornings. Every morning, I make her an iced latte and a Cortado for myself. It’s expensive, but in the long run, I think I think we save a ton of money on coffee. I was never a coffee drinker before this!

  2. Kinto Sepia Cup – I spent hours trying to find the best coffeeware - this is what I landed on. Fancy Japanese coffee cups to go with the coffee machine.

  3. Bean Box Coffee Subscription – A gift a friend got me. Every month, they send you a new brand of coffee beans from a different region

  4. Philips SmartSleep Wake-up Light – I thought spending $150 on an alarm clock would be stupid, but now I wake up feeling more refreshed than ever.

  5. Fishers Finery 100% Pure Mulberry Silk Pillowcase – Silk pillowcases are a game-changer. I sleep at least 10% better with these

  6. Marvis Classic Strong Mint Toothpaste – Fancy toothpaste that is surprisingly cheap. I tried this at The Ned and became obsessed.

  7. Aesop Aromatique Room Spray Trio – I love scents. I have tons of candles and sprays at home. This is my favorite scent by far. Makes any living room smell amazing.

  8. Sun Shower Honey Shower Curtain – A fancy shower curtain with a retro vibe if you’re into that sort of thing.

  9. MoMa Design Author Clock – A small rechargeable clock that tells time with literary quotes that mention the exact time to the minute. That’s 1,440 different quotes per 24 hours.

  10. Cookunity* – The best prepared meals for busy professionals: healthy, tasty plates delivered every week. I’ve been using this for a few months now, and I have no idea what I’d do without it. Use BFCM2560x20 for 60% off.

Fun & Weird:

  1. Heatonist Hot Ones Hot Sauce 10 Pack – If you love hot sauce and want to replicate the experience from the popular video series.

  2. TinyCircuits Portable Retro Mini TV – Just a lil cute thing to put on your desk if you’re a workaholic.

  3. The Deadline Candle – Saw this recommendation from Lenny’s X. It seems to be a good solution for solving procrastination.

    release image

  4. Final Boss Sour Candy – My new favorite candy brand. Great if you need a shock to the system. Extremely sour!

🏢 (Sponsored) The unfair advantage nobody uses.

Founders move a mile a minute. building product, raising capital, running ops. But when it comes to outbound, hours disappear into LinkedIn searches, lead spreadsheets, and barely personalized cold emails that never get opened.

That’s where Ava comes in.

Ava is Artisan’s AI BDR, built for founders who don’t have a sales team yet. She finds leads that match your ICP from 300M+ professionals and 200M+ local businesses, tracks intent signals like fundraising and hiring, and writes personalized outreach across email and LinkedIn.

Set her up once, and Ava delivers dozens of qualified leads each month while you stay focused on building and closing.

You can’t skip outbound. But you can stop doing it the hard way.

👉 Meet Ava at Artisan

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, hit reply, and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 500 founders raise their rounds before the end of the year. Fill this out.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • Resident Office space

  • 🏢 Office space – We just got an office space at Resident in Flatiron - the best neighborhood in the city. There are a few other spots for small teams to work out of. If you’re looking for an office space, check out Resident or hit me up for an intro.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 💸 The No BS Guide to Paying Less in Taxes – Get a free 28-page ebook with 20+ strategies to pay less taxes in 2025. Get it here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🤝 Dion – The networking app that’s blowing up in New York and Miami. Apply here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

I spoke to a group of Cornell master’s students this week about personal brands, startups, and investing, but the questions always circle back to the same things. How do you get started. How do you stand out. How do you avoid getting stuck.

I told them three things:

First, the fastest way to open doors is to give first. Not in a vague way, but in the specific sense of solving a problem for someone. Even if you’re looking for a job, start by asking what they need - then find ways to help them solve their problem.

Second, the gap between people who end up doing great work and people who feel trapped is usually one variable. Risk. The successful ones took more swings. Not because they were smarter, but because they kept trying. You only get a handful of real shots in your life. Six or eight if you’re lucky. Use them.

Third, this is an unusually good time to build things. The tools are better than anything previous generations had. You can put an app in the world in minutes. You can reach millions from your phone. If you want to tilt your life onto a different track, this is the time to do it.

Appreciate the crew for having me!
]]><![CDATA[Making Dreams Come True]]>https://www.andrew.today/p/making-dreams-come-truehttps://www.andrew.today/p/making-dreams-come-trueFri, 07 Nov 2025 16:40:16 GMT👋 Hey, it’s Andrew.

I just got back from Austin, where I stayed up cheering Nicole on as she ran 50 consecutive miles through the night, from 6 pm to 5 am. She is the most inspiring person I know.

While I was there, I had a lot of time in solitude to think about life and career. Today’s post is more personal. It is a transparent reflection on where I am today and where I am heading next. If this resonates, I’d love to hear your thoughts.

📅 Upcoming Events

I remember a vivid conversation with my best friend, Simon, about a decade ago. We were living in Shanghai at the time, talking about how our dream was to live and work in New York City one day. It felt distant and unreal. America seemed like this magical place on the other side of the world. But I could picture us sitting on the ledge of some skyscraper in Manhattan one day, looking out and saying, “Wow, we did it.”

My first 200 sqft apartment in Manhattan. I paid $2,000/month for this box!

I also had this dream of working in a big multinational company, something with marble lobbies and forty floors. I think Suits got to me. I wanted the feeling of being part of a real institution.

Then I dreamed about working for a tech giant like Google or Facebook. I wanted to be inside one of those companies everyone talked about. To feel like I was part of something shaping the world. The perks and culture were just the cherry on top.

At the iconic Google office in New York, working there was a dream come true.

Each dream felt impossible at the time. But somehow, over the next decade, they all came true. I worked at the big companies. I spent time at Google and Facebook. I live in New York now.

And the strange thing about dreams is that once you achieve them, you think of new ones. Because when a dream ends, it leaves behind this quiet space where you have room to think again. And in that quiet, new questions show up. Questions you weren’t ready to ask before. What now? What else? What more is possible?

Along the way, I took an unexpected detour. I never imagined being an entrepreneur or running my own thing. Most people go into this path because they want freedom and autonomy. I never craved that. Not at first. But once I got a taste of it, something changed.

There is a lot that is rewarding about working for yourself. The financial upside, the flexibility, the sense that your life is fully yours. But there is also a different kind of pressure, like accountability, the uncertainty, the loneliness.

I’m 30 now. I’ve been working for about eight years. I think of this as my second career. The first one was the corporate chapter. I learned a lot, made a little money, and built some credibility. Now I’m in the early innings of entrepreneurship. I’m learning new things again.

If I work hard until I’m 60, that means I have around 30 years left. Which is about 80 percent of my career still ahead of me. And everything meaningful takes around 5 to 10 years to build. So realistically, I have about four careers left.

So the question becomes: what is my next dream?

How to Make Your Dreams Come True

When I ask myself this question, I try to remove all logical constraints. I try to remember what my younger self would have wanted before I learned about limitations.

I’ve always dreamed of building something big and cultural. Something that has a physical presence. A physical office filled with hundreds of people. A team. A company that plays a role in shaping culture. Something like Time Magazine, Disney, Starbucks, Lego, or Levi’s. A brand people feel connected to. Something that adds joy, meaning, or belonging to their everyday life. A company that becomes part of how people see themselves. An iconic brand everybody knows.

Obviously, that is insanely ambitious, but again, the whole point this is to dream.

So how do you actually make dreams like that come true?

This is the same framework I’ve used to make all of my past dreams come true, from New York to Google to building my own thing now.

1. Remove the logic.

When you start by asking what is realistic, you cut your imagination off at the knees. Dreams are supposed to feel too big at first. They are supposed to be a little embarrassing to say out loud. The dream comes first. The plan comes later.

2. Ask your 10-year-old self.

The younger version of you knew what lit you up before the world taught you to care about practicality, salaries, prestige, or what makes sense. Ask that version what would make him smile uncontrollably. That answer is usually closer to your truth than anything you can rationalize now.

3. Think in decades.

Everything meaningful takes time. Muscles take time. Companies take time. Reputation takes time. If the dream is big, it will feel slow at first, but that doesn’t mean you’re failing. The people who win are the ones who stay in the game long enough to let compound effects do their work.

4. Reverse engineer it.

Once you know the dream, work backwards from the future version of you.

What skills does that version of you have that you don’t yet?

Who are they surrounded by?

What rooms are they in?

What shaped them?

Create a list of requirements that close the gap between who you are now and who you want to become. Then execute every line on that list.

5. Say it out loud.

The moment you share your dream, the world starts reacting to it. When you declare who you want to become, people who recognize that version of you begin to find you.

And honestly, this might be the most important part.

Every dream I’ve ever had only started taking shape once I said it out loud.

Once you let the world know, it starts to rearrange itself in ways you couldn’t predict. People show up, doors open, and paths you never even knew existed begin to appear.

So let me ask you something:

What are you dreaming about right now?

I’d love to know.

👉 Hit reply and tell me.

If you’re bold enough, post it on LinkedIn and tag me!

🏢 (Sponsored) Take Part in NYC’s Largest Office Survey for Startups (And Get $20)

Hubble is NYC’s largest online platform to find startup office space.

One of the questions they get the most is about how other startups are working:

  • Are they full-time in the office? Are they fully remote?

  • Do they work hybrid? If so, how many days, and is the whole team in? What about the new 9-9-6?

To answer this question, they’re conducting NYC’s largest office survey for startups - they’d love to hear from you!

The survey takes a few minutes. Not only will you be the first to get the report when it’s done, you’ll also get $20 Amazon voucher as a token of appreciation.

👉 Fill out the survey here.

P.S. - You can check out the same report they did in London here.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

EYEBALL, A NEW KIND OF BOOKMARKS APP – A new tool I discovered recently for smart, curious people. It effortlessly saves your links, automatically adds summaries, and sends a hyper-personalized update every Sunday morning about what you saved. Created by a writer, used by thousands of people.

The AI Wildfire Is Coming. It’s Going to Be Very Painful and Incredibly Healthy by Dion Lim – Despite the title, a surprisingly grounded prediction on the upcoming 3–5 year AI cycle to answer the question, “Are we in an AI bubble?”

What’s next? by Jodie Cook – A helpful perspective on those searching for their next thing – whether it is a big career or personal decision. A quote that struck out to me, “Not all those who wander are lost.”

Better Than Free by Kevin Kelly – When things on the internet can be copied endlessly (and nearly free), the value shifts to qualities you can copy. Kevin talks about them here.

Austin Nasso: Impressionable Youth – My friend Austin Nasso is the funniest guy I know in tech. He launched his comedy special this week. Check it out here.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, hit reply, and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • ⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • ⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

I still think Austin is one of the most underrated cities in the US.

Why:

  • Friendliest people I’ve met

  • But also smart people – a lot of retired/exited entrepreneurs and executives settle down here

  • Ubiquitous fitness culture – people here are healthy and happy

  • Lots of space and beautiful nature

  • Affordable housing

  • GREAT food (esp. if you love BBQ)

I recommend visiting.

]]><![CDATA[The Paths to Building Wealth (Part 2)]]>https://www.andrew.today/p/the-paths-to-building-wealth-part-5e2https://www.andrew.today/p/the-paths-to-building-wealth-part-5e2Fri, 24 Oct 2025 12:31:05 GMT👋 Hey, it’s Andrew.

Our team just got back from Leesburg, Virginia, where we took over a private resort for three days with a few hundred founders, investors, and operators. We played pickleball and board games, told stories around the campfire, and founders even had the chance to pitch for $1m.

Little did I know that Loudoun County (where the resort is located) is the wealthiest county in North America, with a median household income of ~$179,000.

Why: federal contracts and employees from DC, demographics – it has the highest rate of college-educated adults in the US, and there are a TON of tech and data centers. >70% of global internet traffic is estimated to route through this area, with Amazon, Google, Meta, and Microsoft having data centers there. Fun fact.

Speaking of wealth… keep reading.

📅 Upcoming Events

  • Nov 13 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series for Seed–Series B founders & CEOs.

  • Nov 14 | ☕️ Founder Breakfast (NYC) – A curated breakfast for 30 early-stage founders and investors (venue TBD)

  • Nov 19 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series for Seed–Series B founders & CEOs.

  • Dec 10 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series for Seed–Series B founders & CEOs.

  • Dec 12 | ☕️ Founder Breakfast (NYC) – A curated breakfast for 30 early-stage founders and investors (venue TBD)

In my last article, The Paths to Building Wealth (Part 1), I talked about the most common paths (I’ve seen) to building wealth.

  1. Finding a stable, high-paying W-2 job in tech, consulting, finance or law

  2. Being a corporate athlete with a side hustle

  3. Building an equity or cash business

  4. Becoming a creator

You’re probably familiar with most (if not all) of these paths and might know someone pursuing these paths.

One of my obsessions has always been finding the most unconventional ways to make money, build a career, and ultimately, create a life on my own terms.

Today, I want to share the less common ones I’ve found.

These are the careers that make people say, “Wait… you can do that for a living?”

The ones most people from my old corporate life have never even heard of.

So let’s get into it – starting from the most common to the least common. Starting with number 6.

6. Riding a Rocketship

Some people get rich by joining the right startup and getting equity that converts at a liquidation event. They manage to place themselves in the right place at the right time. I wrote about it in my past blog post, The Startup Path to Success.

If you can land in the sweet spot of a rocketship – a fast-growing tech company, usually between the Series B and D stages – you can get enough equity for it to be worth a lot of money when the company exits.

A role at a company like this usually also comes with faster career progression, more responsibility, frequent pay raises, and a bunch of other cool benefits.

But the trickiest part is picking the right company.

Honestly, beyond that, you don’t have much control. You have to believe in the leadership team and product, and you might be dedicating many years of your life to a bet that might not even pay off.

Luck plays a massive role, and this path has one of the largest outcome variations here – if you knew how to predict the winners with perfect accuracy, you would be the richest person in the world.

But if you’re fortunate, this path can be life-changing. Not just financially, but professionally. The early employees at unicorns gain access to capital, networks, and knowledge that set them up for the rest of their careers, and many will go on to join other successful startups, launch their own companies, or build strong personal brands that keep opening doors.

Biggest Tech Acquisitions Ever (And Why It Matters to You)
Slightly outdated, but you get the point. Imagine joining one of these companies as their first 100 or first 1000 employees.

7. Indie Hacking

Then we have the indie hackers – the scrappy solo entrepreneurs who build mobile apps, digital products, courses, eCommerce companies, and other short-term projects.

The key phrase here is short-term.

Indie hackers are typically focused on building small, profitable projects instead of longer-term businesses. They aim for base hits, not home runs. Most run multiple income streams, don’t raise venture capital, and try to be profitable from day one – often with 80%+ gross margins.

Levelsio is the poster child of indie hacking. He publicly shares all his projects, and right now he has 7+ projects that collectively generate $600K+ a month in revenue. That’s over $7m a year!

Levelsio is obviously in the top 1% of indie hackers, but I know several other people who are doing fairly well and love this career path. It’s fun, creative, and stress-free, BUT I’ve heard many of them are unfulfilled.

Why? Because they lack a larger purpose beyond making money.

When your work is just selling apps and courses, eventually you hit a wall and ask, “What’s my mission here?”

That said, I think indie hacking is the best entry point for new entrepreneurs. It’s a single-player game. You don’t need a team, funding, or permission. You just start building. And if something doesn’t work, you move on to the next idea.

(Shameless plug for my friend Henrik’s new company, Audos, which helps people build what he calls a “donkeycorn” – a $1M business.

The poster child of indie hacking.

8. Brokering High Value Deals

This path is reserved for the top 1% of salespeople in the world – the hunters.

They find rare opportunities to sell expensive things and take a percentage of the deal for brokering the transaction.

The name of the game is to access more and more rare, expensive things. You start by selling a $1m condo and move your way to selling a $50m mansion. And if you sell that mansion, that’s a million bucks in your pocket. Also, you become known as the guy who has access to mansions, and more people will come to you. A flywheel effect begins.

It doesn’t just have to be mansions, though. It could be jets, cars, vacations, art, and investment opportunities. But you can’t sell everything – you need a niche.

If you spike high on charisma, are a bit of a socialite, and want to get rich by making introductions, this is the path for you. Go into sales where you can get a piece of the pie, then grow the size of the pie.

Real estate and software are great starting points – they’re accessible and teach you the fundamentals of selling. The downside is they’re commoditized markets. But if you can sell something commoditized, you can sell anything.

9. Selling Rare & Specific Knowledge

These are the one-of-a-kind technical specialists who become “experts for hire.”

Their titles usually include Advisor, Consultant, or Fractional Executive. They charge by the hour, per project, or on a monthly retainer. Some even take equity.

Example: Nikita Bier, who is known as the world’s most prolific app builder and virality expert, charges $60K a month for mentorship or ($15K for a 15-minute call). He constantly sells out.

He is the only person in the world who has his specific knowledge and skillset and was even recruited by Elon Musk to run product for X.

Conventional wisdom says you can’t build wealth by selling your time for money. That’s mostly true – unless you can charge a high enough rate or package your knowledge across multiple income streams.

The key is to develop rare, specific, and valuable knowledge in a niche few people understand. If you can become the go-to expert in something truly unique, you can charge $1,000 an hour (or more) and still have people lining up to work with you.

15 minutes of Nikita or the price of a month of rent. Is it worth it? 125 people seem to think so.

10. Hunting for Mispriced Assets

Finally, we have the investors – the people who seek arbitrage opportunities and make money by finding mispriced assets.

Public market investors work at hedge funds and mutual funds, trading equities, stocks, and bonds.

Private market investors operate at private equity firms, venture capital funds, or as angel investors, betting on companies before they go public.

And then there are alternative investors — the ones buying crypto, collectibles, or obscure financial instruments. (I still don’t fully get them.)

Across all of these, the game is the same: build a track record of profitable investments and manage more capital.

Then you take a percentage of the profits AND a fee for “managing” their money, usually around ~2%. This is how you make the big $$$.

I’ve seen “solo GPs” – individual fund managers who manage a $50m fund themselves, taking home $2m in fees every year… plus profits (usually 20%)!

But it’s really, really hard, and meant for the top 0.01%. You need to either be a brilliant investor or an amazing fundraiser.

Most of the people I’ve met who have done well in this field are either extremely analytical + insightful, well-connected, very lucky, or came from a lot of wealth.

Honestly, this seems like the coolest path to get rich, but maybe it’s because I understand it the least. It’s a bit of a black box, and nobody ever talks about their success strategy because why would you give it away if it’s working for you?

Choosing Your Game

Each path has tradeoffs. There’s no “better” one, only what fits you.

It depends on your zone of genius.

Some people thrive in structure and predictability, others crave risk and independence. The game you choose should match your personality, your strengths, and how much uncertainty you’re willing to tolerate.

Across every path, though, there are a baseline skills that will help:

  • Sales and people skills – learning how to persuade, influence, and build trust.

  • Organization and execution – getting things done consistently.

  • Network building – surrounding yourself with the right people.

  • Communication – being able to write and speak clearly.

These are the table stakes, and you should be proficient at all of them.

Beyond that:

If you want a steady, guaranteed path, take the W2 or corporate route.

If you crave risk and asymmetric outcomes, build a business – cash or equity – or hunt for mispriced assets.

If you’re a people and network person, broker deals or play in asset markets where trust and access matter most.

If you prefer single-player games and love to tinker, go the indie hacker, creator, or sell your expertise.

If you’re deeply analytical or an expert in a niche, a W2 role, indie hacking, or a selling expertise path can work well.

And if you don’t want to work for anyone else, Build a business, become a creator, indie hack, or hunt for mispriced assets.

In the end, building a career is more than making money; it’s about finding your harmony of strengths and passions. Find a game that you can play for the rest of your life. The wealth will come.

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, hit reply, and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 🏃‍♂️ NYC Marathon Volunteering Opportunity w/ Rho – Help cheer on runners, support logistics, and be part of an incredible community moment. Volunteers will receive exclusive perks for their time!

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🤖 Sharpen Your AI Edge (Presented by AWS)

Thanks to Amazon Web Services (AWS), this community now has free access to a series of live webinars and podcasts on the latest AI trends and tools. I’m sharing them here because I think they’re some of the most practical resources you can use.

🖼️ Behind the Scenes

Last week, my friends and I rented a cottage in the mountains of Breckenridge, Colorado.

We screwed up.

We didn’t realize that it was 10,000 feet above sea level, and on the first day, we could barely breathe. We had to spend the whole day chugging water and laying low just to conserve oxygen. Rookie mistake.

One thing I’ll never take for granted again: how easy it is to breathe in New York.

But America is stunning. One of my goals next year is to road trip across the country and see all the national parks that people talk about.

Also, we saw a real wild fox that looks AI-generated. Nicole even made a TikTok about it and got over 1 million views.

The beauty of Breckenridge.
NOT AI-generated! He was begging for food.
Our home for the weekend.
]]><![CDATA[The Paths to Building Wealth (Part 1)]]>https://www.andrew.today/p/the-paths-to-building-wealth-parthttps://www.andrew.today/p/the-paths-to-building-wealth-partTue, 07 Oct 2025 14:15:18 GMT👋 Hey, it’s Andrew.

I just got back from a few days in Vegas. It still blows me away me that someone built a massive city of neon lights, fake landmarks, and luxury hotels in the world, right in the middle of the desert.

As a non American, Vegas feels like the symbol of opportunity. It’s a place where, if you’re brave (and maybe a little lucky), you could turn your life around.

That got me thinking about money… and how to make more of it. So today’s article is about just that.

📅 Upcoming Events

I’ve always wondered how people become rich. Maybe because I didn’t have much of it growing up.

I was born in Hong Kong, a country with one of the biggest income inequality gaps in the world. You’d see a luxury mall with Burberry, Cartier, and Gucci right beside government-subsidized housing where the elderly lived in a 100-square-foot apartment with a toilet in the kitchen.

Possibly the most ridiculous thing I’ve ever seen.

In the last few years, I’ve been lucky to meet a bunch of rich and successful people who have made money in ways you can’t imagine. Some were lucky, but the majority of them had a calculated method for building wealth.

So without shame, I fired off question after question until they told me to take a walk. I probably talked to over 100 people – tech execs, lawyers, hedge fund managers, and even YouTubers.

Their jobs couldn’t have been more different, but there were similarities in how they thought about making $.

Eventually, I began to notice patterns. I took a few of the lessons and even made a bit of money myself.

So in case you’re wondering … What are the possible paths I can take to making $$$?

These are the 9 paths I’ve seen:

1. High–Paying Salaried Job

The first one is obvious: tech, consulting, finance or law.

These are people who have spent decades in the corporate grind, working their way up – usually starting as an individual contributor (IC) and eventually becoming an executive or partner, someone with equity in the company.

A friend of mine, 30 years old, takes home close to a million dollars a year as a banker. By 40, he’ll be making a few million dollars a year.

It’s a predictable, proven path to wealth. But he has to keep running on the treadmill.

The “haze” at the start is brutal. 80 to 100 hours a week for the first few years. Always on-call. Most people burn out and leave within the first two years, but once you make it through, the hours slow down and the benefits are great.

The downside: Most people hate their job. They might be the most unfulfilled and bored people I know.

Breaking in is also tough. You need to be “book smart” – a degree from a top school, high GPA, and test well. Certainly not for me!

If you value stability, predictable income, and are amazing at taking tests – this is for you.

On to the next.

Good news: Your entire career trajectory will be mapped out for you

2. Corporate Job + Side Hustle

I worked ~30 hours a week at Google and Meta and still managed to get great performance ratings.

But I’m not very smart… anyone can do it.

It’s not unusual if you find a role you excel at and play the game well (i.e., manage up, be loud about your wins, constantly network).

And if you pull it off, you free up your time and energy for a side hustle.

Like consulting, career coaching, or an “info” biz – selling courses or digital products. These are the most common corporate side hustles I’ve seen.

A friend of mine works 50 hours a week between his $300K/year job and $150K/year side hustle. It’s not millions of dollars, but he lives two different lives and loves it.

Another example: Peter Yang, who is a product lead at Roblox, but has his newsletter, Creator Economy, with over a 100K readers. He gets to do his product thing during the day and interview product leaders and CEOs during the night.

Peter from Creator Economy.

This, to me, is the sweet spot. You get the security, status, and prestige of a corporate job, but can experiment with your creative energy on the side.

I started out like this. I had a corporate gig and a side biz hosting events. I loved it, but after getting a taste of the side thing, I eventually decided to go all in.

This might be the best path for most people, especially if they’re somewhat risk-averse.

I was very close to getting fired when this came out.

3. Building a Cash Business

Before I started one, I thought all companies and biz models were the same. But in reality, there are many flavors of “entrepreneurship”. It’s quite fascinating.

Cash businesses are optimized for producing profit and cash flow from day one. This is the traditional definition of a business (i.e., to make money right away), and before the world of venture capital took over, this was the only type of business you could start.

The beauty of a cash business is control. You own it, you keep the profits, and you don’t have investors breathing down your neck. You can run it for life or sell it when you’re ready.

The challenge is that growth is limited by the cash the business generates. If you want to expand faster, you need to take out debt or raise capital, reinvest profits, or stay small and profitable.

In the shiny, modern-day world of early-stage tech and startups, I don’t see many founders taking this route. Instead, they do the next thing:

4. Building an Equity Business

Equity businesses are designed to grow quickly, raise capital (i.e., convince professional investors to take a chance on you by buying equity in your company upfront), and create enterprise value so that they can be sold or acquired down the road.

In the tech and startup world, many founders raise venture capital, hire quickly, and get on the “triple, triple, double, double, double” growth track. Meaning they aim to go from $1m to $100m revenue in five years, before selling it for billions.

Raising venture capital can be great, as it gives you a few million bucks to spend on hiring, marketing, getting an office, etc., which you otherwise wouldn’t have if you used your own money.

BUT it puts you on the hamster wheel of chasing strict targets and (usually) needing to raise more capital later on.

In either of these examples of building a biz, the harsh truth is that more than 90% of entrepreneurs fail.

In most cases, you are pursuing a low-probability path to making a lot of money. It’s a terribly irrational career choice.

The power law is for startup investing (i.e., 97% of the value is created from 0.1% of startups)

Many venture-backed founders and CEOs will pay themselves between $100K–$200K/year for the first few years. Bootstrapped founders may pay themselves even less (or nothing), but the idea is that they could potentially sell their company for a lot of money down the road.

My hot take is that if you’re going to start a company, you should have an ambitious goal of hitting $5-10m/year. Aim for the moon and land on the stars.

To maximize your chance of success, spend as much time as possible around people who have built companies before. Never listen to “consultants” who have never built anything before.

And if you’re going to raise money from investors, you need to have a goal of hitting at least $100 million per year. I know it sounds ridiculous, but investors won’t fund you otherwise.

5. Becoming a Creator

I’ve met dozens of TikTok creators, YouTubers, and newsletter writers who have made millions of dollars as “influencers”

You don’t necessarily need a million followers, but you do need the right audience. Ideally, a thousand of them… some people call this a thousand true fans.

Creators make money by selling access to their audience: brand deals, sponsored posts, newsletter ads.

The key is having a valuable audience that spends a lot of money.

It’s much more lucrative to have an audience of small business owners who spend hundreds of thousands of dollars a year, vs. teenagers who spend all their time on their phones looking at memes.

I don’t have a massive audience, but I do have a few thousand tech founders and software CEOs who follow me. That alone has helped me earn over $2m in brand sponsorships.

BUT there’s a ceiling.

Most creators I’ve met will cap out at $300K–$500K/year before they have to expand into the other areas that I talk about here.

Some creators who’ve scaled beyond that:

  • Codie Sanchez has multiple $10m+ businesses, including an education biz, a social media biz, and even a venture fund

  • Sahil Bloom has a holding company with multiple agencies that help with personal branding, social media marketing, and design.

  • NAS Daily has a real estate biz, conference biz, agency biz, and venture-backed software biz

Sahil is a NYT Bestselling Author, speaker, investor, and entrepreneur with multiple businesses, including The Inflection, Paperboy, and Consigliere.

Creators at this scale are rarely solopreneurs. They have dozens, if not hundreds, of people around them helping them with execution.

If you enjoy being in the spotlight and creating content, this is a great way to earn a living, BUT you need to be exceptional at capturing attention with video, audio, or writing.

Being a full-time creator can be pretty fulfilling too. You get to impact people’s lives through your reach, often both virtually and in person. But there is a TON of pressure when you’re building something around your personal brand.

But there’s constant pressure when your brand is the business. Every piece of feedback feels personal, and you can never escape it.

✍️ To Be Continued…

I wrote this to make sense of something that always confused me: how people actually get rich and build wealth.

Hopefully, this helped you see that “getting rich” isn’t one thing – it’s a set of different games with different rules.

In part two, I’ll talk about the remaining 4 paths that might be less obvious.

If any of these paths resonated with you (or challenged how you think about money), I’d love to hear which one hit home.

Hit reply … I read every single response!

📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, hit reply and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🤖 Sharpen Your AI Edge (Presented by AWS)

Thanks to Amazon Web Services (AWS), this community now has free access to a series of live webinars and podcasts on the latest AI trends and tools. I’m sharing them here because I think they’re some of the most practical resources you can use.

🖼️ Behind the Scenes

Las Vegas surprised me.

I always thought it was just casinos, lights, and man-made madness, but the nature is what really stunned me.

We went to the Red Rocks to see the massive mountain ranges and I went for a run with Nicole in the desert heat (she’s training for a 50-mile race in Austin).

Barely survived, but it was worth it.

One of my dreams is to road trip across the U.S. next year. If you’ve done this before or have recs, let me know!

Nicole forced me to go on an 8-mile run in the hot Nevada desert. Afterward, I couldn’t walk for two whole days.
]]><![CDATA[How to Build Social Capital]]>https://www.andrew.today/p/how-to-build-social-capitalhttps://www.andrew.today/p/how-to-build-social-capitalMon, 15 Sep 2025 13:25:27 GMT👋 Our team is in the final stretch before we slow down in November: Lumos House – our flagship mansion takeover in New York, Owner’s Only – an epic party for founders and creators, and of course, Distilled Intelligence, our three-day summit in Virginia at a private 500-acre resort. Investor tickets are still available – apply below.

📅 Upcoming Events

Not long ago, someone I had just met (an acquaintance I barely knew) asked me to introduce them to someone important in my network.

“Hey, can you introduce me to this person? I saw you're connected on LinkedIn. Thanks!”

It really irritated me. I wasn’t sure why at first. I love helping people and making introductions. I usually do it instinctively. But something about this one felt off. Maybe it was how they phrased it, or maybe it was how casually they assumed I’d say yes.

So I started thinking more about relationships, specifically, the difference between transactional and non-transactional ones, and how social capital plays a role. I wanted to dig into why some asks feel generous and easy, while others feel like a withdrawal from an account that was never funded in the first place. Around the same time, I came across an article called Dissecting Social Capital, which frankly inspired much of this piece and got me thinking even more.

In this article, I’ll break down the theory of social capital, building trust with others in your community, and how to make sure you’re leaving every interaction with the right impression.

Whether you realize it or not, every conversation is either earning you trust or costing you. Don't make the mistakes most people do.

What is Social Capital?

First, it's important to understand what social capital is. The cleanest definition I’ve seen is that it’s the accumulated goodwill, reputation, and trust you’ve built up with other people. You earn social capital by being helpful, generous, dependable, and credible.

You build social capital when you help a friend land their dream job by making an introduction, prepping them for interviews, and helping them negotiate the offer, without expecting anything in return. You earn their trust, and they see you in a more positive light, which later on can be translated into reciprocity. You become someone they want to help back someday.

Social capital behaves a lot like financial capital. It has three key traits:

  • Productive – you can convert social capital into productive benefits like introductions, favors, and even financial capital.

  • Durable – it retains value over time, but can also erode without maintenance

  • Flexible – it can be substituted for other forms of capital and be used across different benefits

At the end of the day, social capital is a tangible way to measure the breadth and depth of your relationships.

“Transactional” Relationships

When people describe someone as transactional, they’re often thinking of a situation like the one I shared at the start – someone asking for a favor the moment you meet them.

But here’s the truth: all relationships are transactional. Every relationship operates under a social contract between two people, though the nature of those contracts can vary.

What most people label as “transactional” typically refers to relationships where the terms are explicit and conditional. Take an employer-employee relationship: the employer pays a salary, and the employee performs a defined role. The expectations are clear. There’s a direct exchange.

Contrast that with a more implicit agreement, like the one between close friends. Nothing is written down, but the unspoken understanding is mutual support, trust, and time. The “contract” is looser, but still present.

Building Trust

Let’s say you just met someone and purely saw them as a means to an end – someone who can get you a job, introduce you to an investor, or promote your business. You’d probably make the ask regardless of what it might cost them or how little trust you’ve built. You’d act more transactionally.

Now invert it.

You meet someone you genuinely want to build a long-term relationship with over decades. You respect them and believe the lifetime value of the relationship is worth more than any short-term gain. You’d probably be more cautious and wait before asking for anything. You’d focus on building trust first.

There's something slightly paradoxical in most human relationships: people generally don't like making explicit the underlying transactional structure of relationships, but this structure is revealed when people fail to appreciate the principle of reciprocity that relationships are built on.

— Vaishnav Sunil from Optima & Outliers

That’s why the example I shared at the beginning irritated me. It signaled that this person saw me as a shortcut to their goal, not a human worth investing in.

Playing Long-Term Games

So how do you build social capital?

You treat every relationship like it’s going to last for decades. You play long-term games with long-term people.

  1. Build the well. Do things before people ask. Help them solve problems, share opportunities, and connect dots, even when there’s no immediate benefit to you. Build your well long before you need water.

  2. Make introductions thoughtfully. Making an introduction is the easiest way to add value to people's lives. What takes you a minute could result in a decade of value for two other people.

  3. Use the barbell strategy. Keep in touch with small, consistent check-ins – quick messages, reactions to wins, or sending something thoughtful. Then, occasionally, spend deep, quality time together.

  4. Build long-term credibility. Do things that get others to say positive things about you when you're not in the room.

  5. Don’t ask for a favor too early. Or you're signaling that you want to play short-term games.

  6. Think in decades. What would you do differently if this person were around for the next 40 years?

One last thing: some people can brute-force relationships with charisma. They charm their way into rooms and win people over with their energy to make asks. While that might work in the short term, in the long term, I always believe that relationships are built on a mutually beneficial, reciprocal nature.

📌 Andrew’s Bookmarks

Important links to help you become wiser and more creative.

  • How to Design Your Career by Max Marchione – A great piece on how to build a high-slope career by making the right decisions.. I recently interviewed Max in SF and was blown away by how much he's done at just the age of 26. He's built a $300M company In just a few years (and convinced me to invest!)

  • Liquid vs. Illiquid Careers by Vaishnav Sunil – Vaishnav summarizes perfectly the difference between a high-performing linear career (like management consulting) vs a non-linear one (like working at a startup.) The answer lies in career liquidity. If you want stabiltiy, go for a liquid career, if you want upside, go for an illiquid one, but keep in mind the skill stack required to be successful is completely different.

  • Career Advice by Scott Adams – To have an exceptional career, you need to either be the best in the world at one thing, or be in the upper quartile in two or more things. The latter is much easier.

  • Introductions and the “forward intro email” by Roy Bahat – How to actually send a forwardable email. Most people don’t get this.

  • How to Identify Underrated Talent by Max Marchione – To find underrated, high-potential talent, look for slope (speed x acceleration) and these 6 traits.

  • How to Live Near Your Friends by Priya Rose – Why don’t more people do this? There are a few things in life that are guaranteed, but this is one that provides a path to increased happiness and joy.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, DM me and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 💻 Afino – combines AI-powered insights with hands-on finance pros to help you scale with confidence. Book a call here.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Apply here.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 💳 AMEX Platinum – Earn 80K points when you spend $8K in 6 months. Apply.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • Wispr flow

  • What other perks should I include? Let me know.

🤖 Sharpen Your AI Edge (Presented by AWS)

Thanks to Amazon Web Services (AWS), this community now has free access to a series of live webinars and podcasts on the latest AI trends and tools. I’m sharing them here because I think they’re some of the most practical resources you can use.

🖼️ Behind the Scenes

Last week, we threw the NYC Summit afterparty with Fin – a few hundred people showed up and partied with us.

Pulling off an event like this isn’t easy, and this is the Fibe team that made it happen. Grateful for them!

]]><![CDATA[30 Life Lessons from 30 Years]]>https://www.andrew.today/p/30-life-lessons-from-30-yearshttps://www.andrew.today/p/30-life-lessons-from-30-yearsMon, 01 Sep 2025 16:42:58 GMT

I turned 30 yesterday. I’m grateful – I’m incredibly fulfilled, happy, and healthy, and I don’t have it all figured out, but I’ve been lucky to learn from people smarter and wiser than me.

Here are the 30 lessons that stuck with me:

1. Your physical health is the foundation for everything.

I used to think that with enough mental strength, you could brute force long hours and weeks behind a screen to get stuff done. Wrong. You start to feel this in your late 20s.

The foundation for everything mental: focus, energy and productivity – starts with the physical. Good sleep, food, and exercise, in that order. If you want to be a great entrepreneur, leader, creative… get these right first.

2. Critics are proof you’re doing something worthwhile.

If no one disagrees with you, you’re probably irrelevant. Doubters are a sign that you’re doing something significant. Before every major inflection point in my life (getting my 1st job in tech, moving to New York, leaving Google to pursue entrepreneurship), I always had people telling me I was too ambitious. At first, I believed them, but now I use their criticism as fuel.

A real text I received two years ago.

3. How to slow time down.

It seems inevitable that time speeds up as you get older.

The truth is, there are only two ways to slow it down:

  1. Do hard things (run long distances, read slowly).

  2. Do novel things (travel, meet new people, chase new experiences).

Type II fun hurts now but pays back later. If life feels like it’s rushing past, it’s usually because you aren’t challenging yourself enough.

4. To advance your career, learn how to build snowballs.

The highest performers I know share one skill: they can quickly turn abstract ideas into tangible things – like prototypes, mockups, or even apps. These are called snowballs, and they dramatically increase the chance that your idea becomes something significant.

Like building a snowman, the hardest part is making the first snowball. Once you’ve packed it together and placed it on the ground, you just roll it forward. The weight accumulates, and soon the snowball takes on a life of its own.

*Inspired by Henrik Werdelin.

5. Leverage comes from media, code, capital, or labor.

There are only four ways to build leverage:

  • Capital (money working for you)

  • Labor (people working for you)

  • Code (technology working for you)

  • Media (content working for you)

Capital and labor are “permissioned leverage.” You need someone to give you money to invest or people to manage. Code and media, on the other hand, are “permissionless leverage.” You can create them yourself, scale them infinitely, and no one can stop you.

Inspired by Naval Ravikant.

6. Writing is the new resume.

A resume tells people what you’ve done. Writing shows them how you think. A blog, a collection of essays, or even a trail of posts on the internet is a hundred times more effective than a bullet list of jobs.

The best way to evangelize your skills and protect your career is to accumulate artifacts online. Essays, newsletters, tweets, and posts create proof of competence. Years later, people will still find your words, and that proof of work will open doors long after you’ve forgotten you wrote them.

7. There is no alpha in published work.

Alpha is timely, rare information that gives you an edge. It lets you see around corners and act before others, while the rest of the world is still catching up. But alpha is almost never published. Once it’s written down, it’s already old. It’s been reviewed, shared, and acted on.

The most valuable information I’ve ever found came from conversations with people on the fringe, ahead of the curve. Ideas that will never be published, but can change everything if you catch them early.

8. Easy doesn’t mean invaluable. Hard doesn’t mean valuable.

Just because something feels easy and natural to you doesn’t mean it lacks value. More often it’s a sign you’re operating in your zone of genius – doing something others struggle with but you find effortless.

On the flip side, difficulty alone isn’t proof of value. Some things are hard simply because they’re inefficient, poorly designed, or not worth doing in the first place.

*Inspired by Andrew D’Souza.

9. Growth requires shedding your shell.

A lobster only grows by shedding its shell once it becomes too tight, leaving it exposed and vulnerable until a new one hardens.

People are the same way. You can’t expand without letting go of things that once protected you. Everyone reaches a point where they need to pause, shed an old identity, and create space for the next stage.

This might mean quitting your job, taking a sabbatical, tinkering without purpose, or traveling the world. It’s easy to discount these phases as wasted time, but the truth is, they are a necessity for everyone.

*Inspired by Laurie Segall.

10. When you start to walk on the way, the way appears.

Nobody has a fully formed idea when they first begin. But once you start working on it, the map will reveal itself. Clarity comes from action, not thinking.

On the other hand, if you wait for perfect information or a guaranteed outcome, you’ll never start.

*Inspired by Rumi.

11. Seek principles, not outcomes.

Instead of chasing outcomes (e.g. “I want to be a CEO”), consider optimizing for principles (e.g. “I want to work with people I admire). Outcomes are almost always outside your control and depend on variables, timing, and luck.

Principles, on the other hand, are durable. “I want to work with people I admire” is a compass you can carry through your entire career. Principles lead to better decisions, which, over time, create better outcomes anyway.

*Inspired by Henrik Werdelin.

12. The most effective mentorship comes from shared work.

Through a decade of working, I’ve found that monthly standing 1:1s about business or career are usually a waste of time. Neither person has enough context and surface-level conversations can only teach so much.

Instead, I’ve learned the best way to learn from your role models is to do work together and find opportunities to see how the other person thinks, solves problems, and makes decisions.

13. Build the well before you need it.

If I could give only one piece of advice about networking, it would be this: build it before you need it. Most people wait until they’re desperate to reach out, but by then, it’s too late.

Plant seeds early. Meet new people, offer generosity, connect a friend to a job, or help a founder meet investors. Do this consistently over years and the goodwill compounds. When the time comes and you do need a favor, people will be eager to help because you invested long before you asked.

14. Hard is unavoidable – choose your hard.

Building a business is hard, but so is being broke. Staying fit is hard, but so is being overweight. Being financially disciplined is hard, but so is being in debt.

It will never be easy. It will always be hard, but you can choose your hard.

15. You don’t only live once.

Anything worth doing takes 5–7 years. That means you can take many swings at several things in a single lifetime. You can spend a life writing poems, another building things, and another creating art. You have many lives. Live them.

16. Just when you think you’re done, you’re only 40% there.

Exhaustion is often a psychological ceiling, not a physical one. Most of us quit too early. Push further and you’ll be surprised by what you’re capable of.

David Goggins calls this the 40% rule: when your mind tells you you’ve hit your limit, you’ve really only tapped into about 40% of your capacity.

17. One year of obsession can change your life.

We tend to overestimate what we can do in a single day and underestimate what we can do in a year.

But twelve months of focused, daily work is enough to completely reset the trajectory of your life. It’s enough to build a business, transform your body or master a skill. One year of consistent work beats a decade of distracted effort.

*Inspired by Zach Pogrob.

18. There’s always a third door.

Most people wait in the main line - the obvious, crowded path that everyone else is on. A few have access to the VIP entrance, reserved for those with connections, privilege, or luck.

But there’s always a third path. The one you create for yourself with persistence and creativity. It’s not obvious, and no one will tell you it exists, but it’s there. Once you find it, you’ll never take the regular entrance again.

19. Never let anyone forget that they met you.

When you meet someone, make them feel seen and heard. Offer to help. Share an idea. Show up in a way that’s rare enough to be remembered.

Most people are forgettable because they do the minimum. Be the opposite. Be outstanding.

20. It’s impossible to go from 0 → 1 with multiple pursuits at once.

In your 20s, it feels like you have infinite time. You might want to do everything – start a business, explore hobbies, travel the world, and still somehow master everything. But true mastery is slow …it takes years …sometimes decades to break the top 1% at anything.

The hard truth is that if you try to master two things at the same time, you’ll fail at both. Focus is underrated. Pick one pursuit you love and get unreasonably good at it. Once you’ve built depth in one domain, you can always expand into others.

21. Stress is the tax on ambition.

For ambitious people, stress will always be a constant. It’s the price you pay for chasing an audacious goal, and it will never disappear. So the goal isn’t to have no stress, but to stress about the things that matter to you.

Inspired by Sahil Bloom.

22. The best use of money is to buy time, health, or experiences.

Most people treat money as an end goal, but it’s really just a tool. Beyond a certain point, material possessions become status games that add nothing to your life.

Instead, use money to free your time, strengthen your body, and create memories with the people you love.

23. Regularly ask yourself: “10 years from now, what will I be glad I did consistently for 10 years?”

Then do those things.

24. Create more than you consume.

The best way to stand out in a world driven by “What can you do for me?” is to be generous. Share ideas, make introductions, give your time and effort without keeping score. In the short run, it may feel like you’re spending more than others, but in the long run, it comes back tenfold.

Give without the expectation of return, and over time you’ll create a reputation, a network, and opportunities far greater than anything you could have extracted.

25. Learn to build or learn to sell – learn both and you’ll rule the world.

In every field, there are builders (people who create something of value) and sellers (people who persuade others to care about it). One without the other doesn’t go far.

Figure out which one you are and lean into it. If you master one, you’ll be great. If you master both you’ll be unstoppable.

*Inspired by Naval Ravikant.

26. Get a great coach.

I’ve started using coaches for nearly everything I want to learn effectively: public speaking, fitness, and even making videos. A good coach collapses time. They take decades of learning and condense it into a path you can follow in months.

Coaches recognize the blind spots and the common traps you’d otherwise stumble through. If you value your time, hiring the right coach is one of the highest ROI moves you can make.

27. Always ask for more.

Most of us undersell ourselves. We evolved to avoid conflict, to seek safety, to stay within the tribe. That instinct carries into negotiation, where we fear that asking for more will put us at risk.

But almost every number has more room. The first offer is rarely the ceiling. By pushing higher, you not only improve the outcome, you also prove to yourself that your value is greater than you assumed.

28. The paradox of working for yourself: You won’t have hobbies, weekends or vacations, but you won’t have work either.

If you’re doing something that’s truly yours, you’ll care so much that you can’t turn it off. You won’t have downtime anymore, but you won't have work either… and that’s the beauty of it

29. Don’t trade time you don’t have for money you don’t need.

The most dangerous phrase in business is, “But the money’s too good.” It tricks you into selling your time, health, or relationships for dollars you will never spend. You can always make more money, but it is impossible to buy back lost time.

The answer is to define “enough”. Know the life you want, calculate what it costs, and stop moving the goalpost once you reach it. Past that point, money is just a distraction.

30. Everything you’re doing is meaningless.

A decade after you’re gone, nobody will remember you or anything you’ve done. None of this matters as much as we think it does. The world moves on, and everyone is eventually forgotten.

After all, we’re all just monkeys on a small rock, floating through space.

📅 Upcoming Events

  • Sep 9 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series with 24 Seed–Series B founders in NYC, hosted with J.P. Morgan, Vercel, Fridman Law, Codelions.

  • Sep 10 | 🎉 NYC Summit Afterparty (NYC) – Together with Fin, we’re taking over a hotel on the west side with a speakeasy club, rooftop with stunning views, and outdoor garden.

  • Sep 15 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series with 24 Seed–Series B founders in NYC

  • Sep 16 | 🍽️ Junto Founder Dinner (NYC) – A curated dinner serieswith 24 Seed–Series B founders in NYC

  • [Partner Event] Sep 17/18 | 🎤 Monday.com’s Elevate Conference (NYC) – I’m attending Monday.com’s Elevate Conference, featuring speakers from LinkedIn, KFC, and UMG, plus a strong crowd of AI marketers + builders. If you’re working on something ambitious in NYC, come thru - RSVP w/ code ElevatewithAndrew.

  • Sep 23 | 🎤 Fireside Chats at Lumos House (NYC) – Lumos House is back! Speakers TBA.

  • Sep 23 | 🍽️ CEO Dinner + Opening Party at Lumos House (NYC) – For CEOs/founders, held in a private Flatiron loft.

  • Sep 24 | 🎤 Fireside Chats at Lumos House (NYC) – Speakers TBA.

  • Sep 24 | 🍽️ Brandmaker’s Dinner at Lumos House (NYC) – A private dinner for the top CMOs and marketing leaders in New York.

  • Sep 30 | 🚀 Owner’s Only (NYC) – An event for top founders, creators & investors building the best companies of tomorrow, in partnership with OWM.

  • Oct 1 | 🌇 October Tech Rooftop Mixer (NYC) – Our last rooftop mixer of the year, hosted with The Hustle & Superpower (NYC)

  • Oct 14–16 | 🏞️ Distilled Intelligence (3 hrs from NYC) – Our 3-day summit at a private resort for founders, investors & tech leaders. Save your spot now!

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, DM me and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 💻 Afino – combines AI-powered insights with hands-on finance pros to help you scale with confidence. Book a call here.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Apply here.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 💳 AMEX Platinum – Earn 80K points when you spend $8K in 6 months. Apply.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

I'm excited to announce our newest cohort of Fibe Fellows. They'll be joining us this fall, helping out with our events and community. If you see them, make sure to say hi. They are a pretty extraordinary group of people.

]]><![CDATA[Join us at Distilled Intelligence]]>https://www.andrew.today/p/join-us-at-distilled-intelligencehttps://www.andrew.today/p/join-us-at-distilled-intelligenceFri, 22 Aug 2025 14:43:09 GMT

It feels surreal that we’re already more than 60% through the year.

After coming back from San Francisco — where the team and I hosted a series of events at a massive beachside private mansion (a dream come true, I’ve been asking myself:

What do I want to do with the rest of the year?

What impact do I want to make?

And what is the ultimate experience I want to create?

And it led me to do a bit of reflection. Over the last four years, we’ve hosted over 200 events. Yes … 200! Parties, dinners, fireside chats, conferences, you name it.

After every event, I ask for feedback. Sometimes people tell me it felt like a surface-level business gathering where they had to show up as the awkward version of themselves.

Other times, they say it was one of the most transformative experiences of their lives, where they felt heard, connected, and understood.

Through hundreds of iterations, I’ve learned that the recipe for real human connection is:

  • Curation – The people are the event. You need a group with shared interests and a shared mission, but also enough differences to make it interesting. If everyone feels both aligned and useful to each other, good things happen.

  • Programming – Left to chance, people fall back on small talk. You need activities that lower the barriers and give them a reason to talk. The most impactful events send people home with a new idea, a new friend, and a good story.

  • Repeated exposure – Spend enough time together … over a few days or through repeated encounters, and you start to engineer serendipity.

  • Environment – Where you are changes who you are. Put people in nature, near water, or in wide open spaces, and they drop the day-to-day act. They become looser, more curious, more themselves.

Designing an event that brings all this together takes months of planning, hundreds of thousands of dollars, and the right people in the room. But it can be done … and we’re doing it!

Today, I’m excited to announce Distilled Intelligence.

Our 3-day summit for top founders, investors, and tech leaders, hosted at the Landsdowne Resort, a 500-acre resort in Leesburg, VA - just three hours from New York City, with pools, tennis, golf, and nature all around.

We’re doing this in partnership with our friends at Fortify Ventures and Loudoun County on October 14–16, 2025.

👉 Here’s the best part: We’re selecting 100 founders to attend for FREE.

We’ll cover your hotel stay (2 nights), all meals, and admission. All you have to do is get yourself there.

Founders – apply here.

Investors and operators (C-suite, execs, managers) are welcome too - but will have to purchase tickets here (seats are going fast).

We'll have the entire 500-acre resort to ourselves.

This is not your typical summit. We’ve secured an entire resort with:

  • Three golf courses

  • Tennis and pickleball courts

  • Biking and hiking trails

  • Basketball and volleyball

  • Outdoor aquatic complex

  • Full-service spa and gym

  • Restaurants, cocktail bars, and outdoor grills

Lansdowne Resort + Updated Prices - The Knot
Imagine yourself here, making new friends.

Who’s coming to Distilled Intelligence?

We plan to invite the most influential founders, investors, and operators we know across America.

  • Founders will get to meet talent, connect with investors, and even pitch for a chance to win a $1M investment from Fortify Ventures, who famously backed Hinge and ID.me in its earliest days.

  • Investors will meet top LPs (Loudoun County is the wealthiest county in America) and discover new companies.

  • We have room for a select group of tech leaders (C-suite leaders, VPs, Directors, and Head of X) too.

In total, 300–400 people will be there.

Nature, and lots of it.

What’s happening there?

We’ve built programming that helps you meet others, discover investment opportunities, attract investors, and even find top talent. This includes:

  • Fireside chats with iconic founders and operators

  • Curated dinners that bring the right people to the same table

  • Workshops/forums designed to level up both business and personal growth

  • Activities that bring us together through golf, pickleball, tennis, and more.

Everything is accessible but optional, sorta like a pick-your-own-adventure.

At the core of the programming is a pitch competition with $1M committed by Fortify Ventures to invest in winning founders.

We’ve also invited legendary founders from companies like AOL, TechStars, and Venmo to share stories and mentor the next generation.

And yes, it will be fun. We’re over-indexing on connection: one-on-one introductions, small group forums, and plenty of activities.

Virginia Tennis Resort - Lansdowne Resort
Tennis or pickleball anyone?

This is the room you want to be in this fall.

How to save your seat:

  • Founders – Apply here. You can choose whether or not to enter the pitch competition for a chance to win $1M from Fortify Ventures. All accepted founders receive free admission, hotel, and meals.

  • Investors – Purchase a ticket here. We’re welcoming VCs, LPs, angels, and family offices—but vetting every investor to make sure they’re the right fit for the room.

  • Operators – If you’re interested in joining, apply for a ticket here.

If you’re looking to be part of this, don’t wait - apply or grab your ticket today.

See you at Distilled Intelligence.

📅 Upcoming Events

  • [Partner Event] Sep 4 | 🖥️ (Virtual) Smarter GenAI Model Training and Finetuning with Amazon SageMaker – a Series by our friends at AWS.

  • Sep 9 | 🍽️ Junto Founder Dinner (NYC) – A curated dinner with 24 Seed–Series B founders in NYC, hosted with J.P. Morgan, Vercel, Fridman Law, Codelions.

  • Sep 10 | 🌇 September Tech Rooftop Mixer - hosted by Andrew Yeung, The Hustle & Superpower (NYC)

  • Sep 15 | 🍽️ Junto Founder Dinner (NYC) – A curated dinner with 24 Seed–Series B founders in NYC

  • [Partner Event] Sep 17–18 | 🎤 Monday.com’s Elevate Conference (NYC) – I’m attending Monday.com’s Elevate Conference, featuring speakers from LinkedIn, KFC, and UMG, plus a strong crowd of AI marketers + builders. If you’re working on something ambitious in NYC, come thru. RSVP w/ code ElevatewithAndrew.

  • Sep 23–25 | 🏠 Lumos House (NYC) – Sign up for early access.

  • Sep 30 | 🚀 Owner’s Only (NYC) – An event for top founders, creators & investors building the best companies of tomorrow, in partnership with OWM.

  • Oct 14–16, 2025 | 🏞️ Distilled Intelligence (Loudoun County) – Our 3-day summit for founders, investors & tech leaders, hosted at a stunning, 500-acre resort (3 hours from NYC).

📌 Andrew’s Bookmarks

Important links to help you become wiser and more creative.

  • How to Design Your Career by Max Marchione – A great piece on how to build a high-slope career by making the right decisions.. I recently interviewed Max in SF and was blown away by how much he's done at just the age of 26. He's built a $300M company In just a few years (and convinced me to invest!)

  • 8+1 Framework by Henrik Werdelin – Henrik is the founder of Bark, a public company with over 2 million customers and 650 employees. Beyond that, he is also an author, educator, serial entrepreneur, investor, and family man (father and husband). Some might ask, how does he balance it all? This is his answer.

  • Americans Don't Party Enough. Here's How To Change That by Emma Camp – Another piece on why our social gathering culture is declining. Time spent attending or hosting events in the U.S. dropped by 50% in the last 20 years. Many Gen Z's are realizing they have never been to a proper party before. As a tech party host, this makes me sad.

  • The Magic of Showing Up on Your Bad Days by Sahil Bloom – The way I’ve built grit and confidence is simple: doing things when I don’t want to.

    Workouts. Presentations. Speaking on stage. You can’t feel good all the time.

    Sahil says this better than me, but the truth is clear. Average people wait until they feel ready. Exceptional people don’t.

  • The Looming Social Crisis of AI Friends and Chatbot Therapists by Derek Thompson – AI can be shockingly comforting. It mirrors us, reassures us, and sometimes distracts us from asking the right questions. Thompson warns that millions of people (especially vulnerable teens and patients) might begin trusting engineered personalities for life advice, which can reinforce anxiety, narcissism, and social isolation

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, DM me and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

✨ Partner Spotlight

Customer acquisition is evolving fast, and the old playbook isn’t cutting it. Paid social is harder to scale, TikTok’s future is uncertain and Gen Z is skipping search entirely.

Join Forward 2025 by Tatari on Sept. 4 in New York City, a free, half-day event built for ambitious marketers ready to add new channels to the old playbook and scale smarter.

Hear from the co-founders of Reddit, AppLovin, and Poppi, and brand leaders from Saatva, Ariat, Coterie and more as they share today’s growth strategies, from performance TV to community-led discovery.

Wrap the day with a rooftop happy hour alongside speakers and peers. Seats are free, but going fast.

👉 RSVP NOW.

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

  • 💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.

  • 📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.

  • 📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.

  • 🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.

  • 💻 Afino – combines AI-powered insights with hands-on finance pros to help you scale with confidence. Book a call here.

  • 🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Apply here.

  • 🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 💳 AMEX Platinum – Earn 80K points when you spend $8K in 6 months. Apply.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Equinox – Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know.

🖼️ Behind the Scenes

Last week our team: Jacob, Alime, Oscar, Ryan, and our honorary 5th member Bailey (founder and CEO of Cal.com) — spent the week together at a beachfront mansion hosting events.

It was the first time we all flew out for an event, and it reminded me why I love this work. We’ve spent years helping others find their community, but we haven’t always done it for ourselves. That’s starting to change.

We’re slowly expanding the team, bringing on fellows and interns. The job is simple: we need social, high-energy, curious people to help with event logistics and be in the room with CEOs and decision-makers.

If you love being around founders and builders, and you’re excellent at operations and logistics, we’d love to meet you. Reply with a few sentences on why you’d be a fit.

Open postings:

  • Fibe Fellow – An unpaid, part-time learning and shadowing program designed for operators 1–5 years into their careers who want broader exposure to the startup and venture ecosystem.

  • Community & Events Intern – A paid, part-time role for students or recent graduates interested in learning community, events, and marketing. Interns will support event logistics and planning while gaining hands-on experience.

After 48 hours of socializing, hosting events, and meeting people!
]]><![CDATA[The Art of Unconventional Career Building]]>https://www.andrew.today/p/the-art-of-unconventional-careerhttps://www.andrew.today/p/the-art-of-unconventional-careerTue, 05 Aug 2025 12:49:50 GMT🖥️ Today’s issue is brought to you by our sponsor, AWS.

Meta & Amazon are teaming up to help startups supercharge their generative AI innovation. They just launched this new initiative, and they’ll be selecting 30 startups to join this 6-month program, where they are offering:

  • Up to $200K in AWS credits

  • Access to a dedicated team of business and technical experts from both AWS and Meta

  • Networking opportunities with top AI leaders

  • Dedicated 1:1 technical support

This is a sweet deal!

👉 Apply by August 8.

I recently met Henrik Werdelin, the co-founder of BARK (NYSE: BARK), formerly known as BarkBox, a product subscription service for dogs that grew to over $500M in annual revenue, 650+ employees, and IPO’d at a $1.6B valuation.

Henrik also started Prehype, a venture studio that launched 30+ startups, including several unicorns like Ro Health. More recently, he founded Audos, which is building AI tools to help 100,000 people become founders.

In just a few hours, he completely reshaped the way I think about my career, and after reading this, he might reshape yours, too.

BarkBox provides customized boxes of themed toys and treats for your pup.

Henrik’s career journey is as unconventional as it gets. Before building companies, he started in radio at the BBC in Denmark, then moved into product innovation at MTV and later the BBC in London. He never imagined, in his early days, that he’d one day start a company for dogs.

It may not seem obvious, but throughout his career, Henrik has followed a consistent philosophy and clear set of principles that led him to build multiple unicorns and an extraordinary path for himself, but despite everything he’s built, Henrik remains humble, open-minded, and deeply curious.

I spent a few hours with him digging into his journey, his mental models, and his approach to work and life. Here’s what I learned:

Smiles all around.

Seek Principles, Not Outcomes

Most people optimize for outcomes: I want to be a CEO, I want to raise a Series A, I want to build a unicorn.

Henrik suggests inverting the model – instead of chasing outcomes, optimize for principles. For example, I want to work with people I admire, I want to push myself outside my comfort zone, I want to constantly learn new things.

Why it matters:

  • Outcomes are often outside your control: You can control your principles, work ethic, and decision-making process, but you can't directly control whether you get the exact outcome you want..

  • Prevents outcome-chasing mistakes: When you focus too much on specific outcomes, you might compromise your principles or make short-sighted decisions that ultimately hurt you.

  • Long-term optimization: Principles create a sustainable approach that works across different scenarios and time periods, while outcome-focused thinking can lead to you constantly changing your approach to optimize for immediate results.

Henrik references The Score Takes Care of Itself, the leadership classic by NFL coach Bill Walsh. Walsh’s message: If you follow sound principles, you give yourself the best chance of winning. The score (outcome) naturally follows from a good process.

Henrik’s most important principle: Work with people you like and admire over everything else.

Henrik looks for three traits in people:

  1. Agitation – Self-propelled people who constantly have an itch. They can’t help but want to take action and solve problems, and are the type of people who immediately follow up after a meeting with fifteen ideas.

  2. Gravity – Unconventional, quirky people who are original and unconventional vs those who are successful by the book. They have a magnetism to them that attracts people, things, and luck.

  3. Wide Interest Spectrum – Those with intellectual curiosity who are curious about many things. They are naturally inquisitive people who want to know how the world works.

These are the qualities he’s used to choose who to hire, invest in, and build with over the past two decades.

The founding team at BarkBox: Henrik Werdelin, Carly Strife, Matt Meeker.

The Snowball Framework for Career Advancement

The Snowball Framework is Henrik’s metaphor for how to build momentum in your career and in life.

The truth is that most people struggle to turn abstract ideas into tangible things. But once you convert a concept into a thing that people can react to, like a prototype demo or even a website, you gain what Henrik calls gravity.

People can then react ("that's cool" or "I hate that"), get excited, and momentum will build naturally. On the other hand, abstract ideas that remain in your head generate no reaction.

The Snowball Framework: Like building a snowman, the hardest part is making the first snowball. Once you have it, you put it down and start rolling it downhill - the rest becomes relatively easy because momentum carries it forward.

  • At MTV, his boss rejected an idea for an internet show. So Henrik broke into the studio at 2 am and made it anyway. He got promoted.

  • At BarkBox, Henrik built a quick prototype in 48 hours and took it to a dog park. Using Square on their phones, they signed up 70 paying customers on the spot.

Today, building snowballs is easier than ever.

With AI tools like Lovable (mockups), Claude (copy), and Replit (prototypes), anyone can turn an idea into something tangible in a few hours.

Early in your career, when time is your most abundant asset, the upside of building something is massive …and the risk is nearly zero. You will never be penalized for showing up with a solution to someone’s problem.

Audos’ mission: to launch 100,000 companies in 2026.

A few years ago, the adage went: "Ideas are worthless, execution is everything.”

But AI has changed everything, and today, the opposite is true: Ideas are more valuable than anything else.

Designing a Life with the 8+1 Framework

Finally, Henrik shares the framework he uses to juggle running multiple businesses and raising a family. In addition to building companies, investing, and launching new ventures, he’s also written a book, hosts a podcast, teaches entrepreneurship at the university level, and is a husband and father to a young son.

With all those commitments, it's easy to wonder: How does he do it all?

The answer is that he's developed a system for himself. It’s called the 8+1 Framework. It’s deceptively simple.

Henrik organizes his life into eight key “boxes,” each representing a domain he wants to stay intentional about:

  1. Transact – Income-generating work (advising, operating, paid projects)

  2. Invest – Activities with compounding returns (reputation, equity, learning bets)

  3. Assist – Helping others (mentorship, introductions, writing)

  4. Learn – Staying intellectually sharp and curious

  5. Health – Fitness, nutrition, sleep, and mental well-being

  6. Family – Quality time with his family

  7. Relationships – Deepening friendships and professional connections

  8. Ego / Self-Kindness – Joy, play, gratitude, and moments that refill the tank

He uses these boxes to categorize how he spends his time and attention, and always aims to have his activities fit into one or more boxes.

The “+1” is the review. Every week, Henrik sets aside time to reflect on each box. What’s full? What’s getting neglected? What adjustments or experiments can he run to rebalance things? The discipline to pause and check in is what makes the system work.

It’s a simple framework, but when followed consistently, it keeps him aligned with the life he actually wants to live.

A scene from the BARK IPO in 2021.

How to Take Advantage of the Next 3 Years

I genuinely believe we’re entering a period where the way you spend the next 1–3 years could shape the entire arc of your career.

I’ve worked at the biggest tech companies in the world …and with the scrappiest early-stage founders, and I’ve never seen momentum like what we’re seeing now.

Wherever you are in your journey, Henrik’s story offers a few timeless (and timely) ideas:

  • Principles > outcomes. Let values guide your path, not titles.

  • Build the snowball. Make ideas tangible. Don’t wait for permission.

  • Work with people you admire. Find your most important filter.

  • Use AI as leverage. You can build faster than ever before.

  • Stay curious and generalist. The future belongs to those who wander with intent.

  • Design your life, not just your work. Use systems like the 8+1 Framework to stay intentional across everything that matters.

Your path may not be linear; in fact, it often isn't. But if you follow the right principles, build snowballs, and stay open to unexpected opportunities, you'll end up somewhere remarkable.

And if that path involves building a company or chasing an idea, Henrik’s next mission might resonate. He’s aiming to help 100,000 people build companies in 2026.

If you want to be part of that journey, follow along with what he’s building next.

👉 What’s Next

  • 📘 Get Henrik’s book: Me & My Customer: The New Rules of Entrepreneurship. A must-read for anyone building in the AI era. Buy it here.

  • 🔥 Join our fireside chat on August 18 (NYC): We’ll go deep on career design, unconventional paths, and how Henrik thinks about building the next 100,000 founders. RSVP here.

  • 🍷 Apply for our private dinner on August 18 (14 seats only): I’m cohosting an intimate dinner with Henrik in NYC. Apply here.

📌 Andrew’s Bookmarks

Important links to help you become wiser and more creative.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, DM me and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Community Perks

  • 🏃 Achieve peak health + performance. Improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Use ANDREW100 for $100 off.

  • 🍽️ Love dining out? Get up to 30% off your bill at top restaurants in NYC and most US cities with InKind. It’s the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 💳 Sign up for the AMEX Platinum. Earn 80K points when you spend $8K in 6 months. Sign up here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Discounted Equinox membership in NYC. Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know...

🖼️ Behind the Scenes

I’ve completely changed my lifestyle in the past 6 months.

Quarterly bloodwork (with Superpower) to track improvements.

5 sessions per week in the gym. Heavy focus on legs, lower back, and core.

4+ hours of Zone 2 cardio per week. 30+ minutes of Zone 4.

Daily supplements (Zinc, Magnesium, Omega 3s, B-Complex, Vitamin D3 and some other stuff)

A clean diet (with 1x/week cheat day) and a lot of water.

10,000+ steps a day.

A Garmin watch (Forerunner 265) and an Oura ring to track everything.

It’s made all the difference.

I always have energy, I don’t need caffeine anymore, and I’m insanely productive.

It’s true what they say – the best productivity hack is sleep, diet, and fitness. Solving for health solves everything else.

If you wanna join me on the health grind, I’ll catch you on the West Side Highway.

Thanks for reading Andrew Yeung's Newsletter! Subscribe for free to receive new posts and support my work.

]]><![CDATA[The Startup Path to Success]]>https://www.andrew.today/p/the-startup-path-to-successhttps://www.andrew.today/p/the-startup-path-to-successTue, 22 Jul 2025 12:31:19 GMTWelcome to the 163 new subscribers who have joined our community of 50,282 readers! If you haven’t subscribed, join us below:

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🖥️ Today’s issue is brought to you by our sponsor, Delve.

We’re thrilled to announce our $32M Series A at a $300M valuation, led by Insight Partners! Delve is shaping the future of compliance with an AI-native approach that cuts busywork and saves teams hundreds of hours. Startups like Lovable, Bland, and Browser Use trust our AI to get compliant - fast.

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Get compliant with Delve today.

I spent the first five years of my career chasing prestige, landing at Meta, then Google, for the stability, benefits, and six-figure paychecks.

I was told that working at a “blue chip” company was the only path to success. Despite the great title, perks, and decent lifestyle it afforded, I still felt stuck running on a treadmill.

Meanwhile, a few friends took chances on startups, found more fulfilment, learned more skills, and walked away with life-changing money. They didn’t retire to a beach but became “post-economic”, and money no longer dictated their decisions. Watching them taught me that a small equity stake in the right team can outpace even the best big tech offer.

Picking the right startup takes experience, research, analysis, and access. It’s not easy. But when it pays off, it can have massive impacts on your life.

Today, I’ll talk about the Startup Path to Success and why choosing to work for a startup can be a great decision, not only for creating a good economic outcome, but also for accelerating your learning and career.

Andrew at Facebook, circa 2020.

The Case for Startups

Big‑tech roles pay well but cap your upside. Even with annual bonuses and RSUs, you’re still trading time for dollars. Over ten years, a Google PM might earn $4 million pre‑tax, a salesperson $2 million, and an engineer $5  million. Sounds great, until you realize most people save only about 8% of their pre‑tax income. On $4 million, that’s just $320,000 after a decade set aside before interest and capital gains.

Early‑stage startups flip that model: you accept a lower salary in exchange for the chance at life‑changing liquidity.

As a mid‑level operator joining around the 100‑employee mark, here’s what you might see:

  • Scale AI – Joined ~100 people in mid-2018; sold in the $25 billion tender offer (March 2025) → $8 M–$12 M

  • Slack – Joined at Series C (~mid 2016); held through the $27.7 billion sale to Salesforce (late 2020) → $5 M–$8 M

  • LinkedIn – Joined at ~100 headcount (circa 2008); exited on the $26.2 billion Microsoft deal (2016) → $9 M–$12 M

  • Uber – Joined at Series D (~2015); rode into the $82 billion IPO (mid 2019) → $30 M–$45 M

  • Snowflake – Joined ~100 employees (mid 2018); held through the $70 billion IPO (Sept 2020) → $20 M–$30 M

*All figures assume standard four‑year vesting, a 30 percent dilution buffer, and no refresh grants.

Obviously, these outcomes are extremely rare. Up to 90% of startups fail within five years, meaning only about 10% survive long enough to hit a major liquidity event. And even among survivors, only around 16% of companies ever get acquired by the Series E stage.

This makes spotting the right opportunity (and holding through to the end) critical if you want your small equity stake to turn into an outsized outcome.

However, there is another argument to be made to make a bet on a startup.

Accelerated Career Advancement

Startups can also offer faster career advancement and promotions, skill development, and, in some cases, salary growth.

Why?

In a small team, there’s no one else to pick up the slack. If you join as an individual contributor, you’ll quickly find yourself owning projects end to end, and put in positions that large companies usually reserve for senior hires.

You won’t waste quarters waiting on committees or endless meetings to get sign‑off. Decisions happen in days, not months, so you learn to iterate, pivot, and deliver impact almost immediately. That rapid feedback loop accelerates your learning curve and makes you indispensable.

Early employees often get tapped to build and lead teams because they already know the product, the customers, and the culture. It’s possible to go from individual contributor to Director (managing a team of ten) in five years, whereas on the big-tech track, it can easily take over a decade.

I’ve seen it myself: friends who left Google, Uber, and Microsoft for startups often tell me they learned more in their first six months than they did in years at a FAANG. They took on leadership roles, shipped critical product features, and built networks that positioned them for even bigger opportunities down the road.

Standard promotion schedule at Facebook and Google. Entry-level individual contributors at the top. It typically takes 2–3 years to progress to each subsequent level. Most people will cap out at L5/L6, never hitting Director.

Liquidity Events Explained

But how does startup equity translate into cash?

You’ve seen how powerful these outcomes can be if you joined fairly early. Let’s take a look at the mechanics behind these returns… this is how founders, employees, and investors actually turn startup equity into real money:

  1. Acquisition
    When a buyer steps in, your equity converts to a lump‑sum payout. Slack’s $27.7 billion sale to Salesforce, LinkedIn’s $26.2 billion acquisition by Microsoft, and Fitbit’s $2.1 billion purchase by Google are good examples.

  2. IPO
    Going public unlocks tradable shares. Snowflake raised $3.4 billion on day one, Airbnb debuted at a $100 billion market cap, and Uber launched with an $82 billion valuation. Vested employees can sell into the open market—and in some cases, watch their initial grants double in value before lunch.

  3. Secondaries
    Private‑market buybacks let you cash out long before any acquisition or IPO. Notion’s $10 billion secondary, Stripe’s $65 billion tender offer, and Robinhood’s $55 billion pre‑IPO trades all gave employees liquidity without waiting for a traditional exit.

How to Pick Your Path

Most people assume there is only one path to career success, and they chase the logos splashed across TechCrunch and Business Insider. But there is massive upside with startups that few even notice. With a bit more effort and independent thinking, you can find those hidden gems—and see massive gains in your career, your skill set, and maybe even your wallet.

Of course, predicting the next unicorn is insanely hard, and few have nailed it. Still, there are signals most people miss … once you learn to spot them, your odds of choosing the right company go way up.

  1. Develop Your Thesis
    Start by choosing an industry you believe in and love, whether it’s healthcare, fintech, or consumer. Then narrow down on a specific niche where you feel like you can spend hours learning about the space without getting bored. This will be your unfair advantage that will let you go deep into the space.

  2. Track the Right Signals
    Follow the CEOs and leaders on social media. Read their newsletters and stay informed with fundraising and product launch announcements. These early funding rounds often pinpoint a moment where they are about to accelerate and start hiring quickly. Pro tip: Y Combinator, StartX, and the Thiel Fellowship have a great track record of producing unicorns.

  3. Build Insider Access
    Once you have your “target list” of companies you want to work for, start reaching out to the decision makers there. Show up at demo days, industry meetups, investor events, and even cold outreach to the founders, offering a way to be valuable to them. Attend relevant events (including mine), and build your relationships.

  4. Join at the Right Stage
    Getting in early often makes the difference between a good equity outcome and a life-changing one. Roles before Series A carry the biggest upside but the biggest risk since the company is still finding product-market fit. Series B to C positions balance risk and reward as you join after initial traction but before valuations skyrocket. Series D and beyond offer more stability and clearer liquidity paths, though your equity slice will be smaller. Decide which stage aligns with your risk tolerance and career goals and target teams accordingly.

  5. Vet Founders & Teams
    Evaluate companies like you would if you were investing in them. Look for founders who have built or scaled successful companies before or operators with deep domain expertise. Reach out to current and former employees to learn about the company culture, runway, and leadership style. The right team will be transparent about risks and realistic about how they plan to win.

No alternative text description for this image
The monthly tech mixer I host – where tech founders, investors and operators gather. A great place to network and “get into the room".”

That’s your playbook in a nutshell: pick a space you care about, watch for the early signs, get to know the insiders, jump in at the right moment, and evaluate the team like you’re doing your own startup due diligence.

Obviously, this is not guaranteed - you won't find a unicorn, but you'll be making smarter bets, which means better career moves, learning skills you can't learn anywhere else, and the chance at a significant financial payday that most people will never see.

P.S. Some venture funds, including the one I invest out of, will share updated lists of startups that they are most bullish on. Sharing some below for you as a starting reference point.

P.P.S. For a head start on choosing awesome startups to work for, check out my job listings below. Most of these companies are either ones that I’ve invested in or have had on my radar for a while.

📌 Andrew’s Bookmarks

Important links to help you become wiser and more creative.

  • Your Company Name Matters…a Lot by James Currier – A good is more than just branding. It shapes how people talk about you, remember you, and believe in what you’re building. Currier breaks down what makes a name stick, plus examples of what to avoid. Worth a read.

  • Flounder Mode by Brie Wolfson – When you’re building a company early on, everything is messy… no clear path, no traction, just a bunch of half-baked ideas. This piece puts a name to that stage: flounder mode. It’s a reminder that wandering isn’t failure. It’s part of the work.

  • How to see the humanity in anyone by Scott Shigeoka – It’s easy to judge others. The harder t hing to do is to stay surious. Whenever I find myself forming a judgement, I try to require my brain to lean in with curioisty instead. It’s served me well.

  • 3 Human Skills That Make You Irreplaceable in an AI World by Scott Galloway – AI can do a lot today, but it can’t build relationships or tell a great story. Scott’s point: The human skills of communication, judgement, and emotional presence will matter more than ever.

  • The Connection Economy Playbook by Andrew Yeung – I partnered with HubSpot to put together a free playbook on how you can build your network and use it to accelerate your career, which includes DM templates, personal branding toolkits, and even an event design guide.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, DM me and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Community Perks

  • 🏃 Achieve peak health and performance. Improve your routine by tracking 100+ biomarkers to get a comprehensive view of your body and become healthier + more productive with Superpower – a company I invested in! Use ANDREW100 for $100 off.

  • 🍽️ Love dining out? Get up to 30% off your bill at top restaurants in NYC and most US cities with InKind. It’s the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.

  • 💳 Sign up for the AMEX Platinum and earn 80K points when you spend $8K in 6 months. Sign up here.

  • 🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.

  • 🚴 Discounted Equinox membership in NYC. Reply here for a free trial and discounted membership.

  • What other perks should I include? Let me know...

🖼️ Behind the Scenes

We’re taking over Sharon Stone’s former Seacliff mansion in San Francisco.

August 13–14. We’ve partnered with Wefunder to host a series of beach workouts, fireside chats (speakers to be announced), and dinners for founders at the mansion.

👉 Sign up here

Also, we still have room for sponsors/partners!

]]><![CDATA[How to Live Longer]]>https://www.andrew.today/p/how-to-live-longerhttps://www.andrew.today/p/how-to-live-longerTue, 08 Jul 2025 12:31:36 GMTWelcome to the 134 new subscribers who have joined our community of 50,119 readers! If you haven’t subscribed, join us below:

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I just returned from two weeks in Hong Kong. My home!

While I was there, I learned something that surprised me: Hong Kong has the highest life expectancy in the world.

As of the latest data, women live to 88, men to 83.

This is eight years longer than in the U.S., where the average is 76. That’s not a marginal lead … it’s a full five to six years longer than in most developed countries.

How did that happen?

The obvious answer is “good healthcare,” but that doesn’t explain the full picture.

Many countries have advanced medicine. Hong Kong’s advantage is more foundational – the result of hundreds of habits people have made daily over decades.

Here are the main things I’ve observed:

  1. They walk everywhere.
    Most people don’t drive. They take the MTR (subway), which means walking to the station, changing lines, and walking home. On average, people in Hong Kong walk about 6,880 steps a day — over 2,000 (+40%) more than the typical American. That doesn’t sound like a lot, but over the years, it adds up, and that turns out to be one of the most reliable predictors of how long you live.

    An elevated walkway in Hong Kong that lets you travel from one end of a neighborhood to the other—passing through malls, subway stations, and apartment complexes—without ever stepping outside.
    Hong Kong’s subway system is remarkably efficient, with stations and routes covering nearly every corner of the city.

  2. Their food is light by default.
    In Cantonese cooking, you’ll find little oil, meat, or sugar, and almost no dairy. Meals are steamed or boiled, occasionally given a quick stir-fry with minimal oil. Most meals include vegetables, seafood (such as steamed fish), and soup, all served in small portions. It’s not that people are trying to be healthy; it’s that food has never been industrialized in the same way that Western diets have, with mass processing, additives, and artificial ingredients.

    You might not realize that dim sum—har gow, siu mai, char siu bao, and more—has its roots in Hong Kong. These dishes are lightly steamed and surprisingly healthy.

  3. Almost no one smokes and drinks.

    Hong Kong’s smoking rate is 9%, compared to a global average of 17%. That alone accounts for a large share of the difference in heart disease and cancer rates. Barely anyone consumes alcohol too – only 8% of adults drink regularly vs 55% in the U.S. But it’s not that people in Hong Kong don’t have their vices, though, as 64% of the population gambles! (card games and horse-race betting)

    Horse racing at the Hong Kong Jockey Club.

  4. The city forces movement.
    Hong Kong is dense and vertical. You constantly walk up hills. You climb stairs. You carry groceries. Even errands require some degree of physical effort. That turns out to be more effective than gym memberships. It’s also probably why everyone there seems to have big calves.

    The mid-levels escalator in Central that moves upwards in the morning to help people get to work and downwards in the evening to help them get home. Very smart.

  5. Moderation is the norm.
    There’s a cultural bias toward not overdoing things — in food, alcohol, even ambition. People eat until they’re not hungry, not until they’re full, and there’s a Cantonese saying for it: 適可而止 … which translates to the idea of “not overdoing it.” There’s no binge culture and all-you-can-eat buffets here and it turns out that this kind of restraint, practiced consistently over a lifetime can be pretty damn healthy.

  6. Active community participation.
    Older adults remain an integral part of everyday life. They live with family, walk through parks, chat with neighbors, and do their grocery shopping in the same markets as everyone else. This type of daily connection makes a big difference. Loneliness increases the risk of early death by over 26%—it’s now considered a public health epidemic in places like the U.S.

  7. Adoption of mind-body rituals.
    You’ll see people in Hong Kong practicing Tai Chi or Qigong at the parks every morning. It looks simple, almost too slow to matter, but it works by calming the mind, keeping the joints moving, and helping with balance and sleep. It’s the eastern equivalent of breathwork, yoga, and meditation, combined. Over 70% of the elderly do this multiple times a week, and science shows that this helps with sleep, blood pressure, cognitive function, and mood.

    A community of Tai Chi practitioners in Kowloon Park, Hong Kong.

  8. Proactive health checkups.

    And finally, this one might sound obvious, but it’s hugely underrated: people actually go to the doctor. More than half of adults participate in regular health exams as a preventative habit. It makes a massive difference because early detection is one of the most reliable tools we have for extending both lifespan and health span. In many places, especially in the West, we treat doctors like firefighters – only calling them in once something is burning. But the better model is to treat them like coaches – checking in regularly, tracking trends, and adjusting course before things get bad.

None of this is a secret. There’s no miracle drug or wild bio-hack, but a small set of habits that, done consistently over a lifetime, stack the odds in your favor.

The question, then, isn’t just “Why are people in Hong Kong living longer?”
It’s “What can we learn from them …and apply to our own lives?”

How to Live Longer—Without Moving to Hong Kong

You don’t need to move to Hong Kong to benefit from the lifestyle habits that drive its record-setting longevity.

Here are a few ideas worth stealing:

  1. Walk more, but don’t treat it like exercise.

    Skip the “go for a walk” mindset and instead build walking into your routine. Take the stairs, walk during calls, run errands on foot. Shoot for 8,000+ steps a day. You’ll get there without even realizing it. I’ve had the Oura Ring for 3 years now and it helps me track all this, and more.

  2. Eat until you're not hungry, not until you're full.
    Follow the 80% rule. Eat slowly, use smaller plates, and avoid screens or multitasking during meals. No need for calorie counting, just stop right before you get full.

  3. Prioritize whole, light meals.
    Keep it simple: Eat more plants, fish, veggies, and rice. Less processed oils, sugar, and dairy. Steamed, boiled, and lightly fried dishes are your friends.

  4. Limit alcohol … it adds up quickly.
    You don’t need to quit, but cutting back makes a real difference. Swap in a zero-proof cocktail, save drinks for the weekends, and notice how you sleep on nights you don’t drink. It’s not subtle. Btw I wrote about being sober for 2 years – read it here

  5. Make social connection a daily default.
    Make “micro-connection” part of your routine: Call a friend while walking, eat with others instead of alone, and find a recurring group activity (sports, meetups, volunteering). I invested in a company called Pie, run by my friend Andy Dunn, that helps with this.

  6. Start a mind-body ritual you can actually stick with.
    This is less about spiritual enlightenment and more about nervous system regulation. Try breathwork (use apps like Othership – another investment of mine), cold showers, or yoga classes.

Pick 1–2, commit for 30 days, and you’ll feel the difference.

P.S. A tool that’s made a huge difference for me is Superpower.

Here’s the big idea: for years, elite health tracking was only available to Silicon Valley billionaires with private doctors, concierge labs, and full-time coaches. Superpower is making that kind of care accessible to everyone.

It tests for 100+ biomarkers—way more than you’ll ever get from your regular doctor—and uses AI to give you real, personalized recommendations. Not just vague tips like “eat better” or “sleep more,” but stuff like:

  • What supplements to take

  • What your ideal workout routine looks like

  • How to optimize your sleep

  • What your blood is telling you about inflammation, hormones, metabolism, and more

Honestly, it’s surfaced data I didn’t even know existed … things my annual physical has never even hinted at. And those insights have directly changed how I eat, how I train, and how I structure my day.

Highly recommend checking it out. Use ANDREW100 for $100 off.

📌 Andrew’s Bookmarks

Important links to help you become wiser and more creative.

  • How I Stopped Worrying About AI and Learned to Value My Humanity by Sari Azout – You don’t need to compete with AI by being faster – you win by being more human. Sari makes the case for slowing down, paying attention, and doing the things machines can’t: feeling, caring, and thinking deeply.

  • The Connection Economy Playbook by Me! – I partnered with HubSpot to put together a free playbook on how you can build your network and use it to accelerate your career, which includes DM templates, personal branding toolkits, and even an event design guide.

  • Longevity Can Save America by Omri Drory, Ph.D. – Most people think that longevity is just about health, but in fact, it can be an economic engine too. Longevity could boost productivity, cut healthcare costs, keep more people in the workforce… and ultimately, drive economic value.

  • The Rise of the Swiss Army Knife Worker – AI is breaking down job titles. Young professionals are switching fluidly between roles without needing to specialize. One exec said if he didn’t know someone’s title, he couldn’t guess it. Everyone’s becoming a team of one.

  • 15 AI Tips and Workflows I Wish I Knew Sooner (from 400+ PMs and Founders) by Peter Yang – This is packed with practical ways to actually use AI day-to-day and write faster, summarize calls, build MVPs, and even learn quicker. Worth skimming and saving.

  • Tech, Without AI, Feels Kinda Bleak – Outside of AI, tech no longer feels like the exciting, high-status career it was a decade ago.

💼 Job Board

Sharing job opportunities that my friends are hiring for. If we know each other well, DM me and I can connect you directly.

👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.

💃 Community Perks

  • 🏃 Achieve peak health and performance. Improve your routine by tracking 100+ biomarkers to get a comprehensive view of your body and become healthier + more productive with Superpower – a company I invested in! Use ANDREW100 for $100 off.

  • 💻 Still running your finances from a spreadsheet? Afino combines AI-powered insights with hands-on finance pros to help you scale with confidence. Book a call here.

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🖼️ Behind the Scenes

I built an app last weekend. I don't know how to code.

It’s a simple fitness habit tracker that helps me track my workouts, cardio, and supplements.

I vibe-coded the whole thing in < 3 hours while watching Netflix.

I used
• Lovable (for vibe coding)
• ChatGPT (to debug and guide structure)
• Supabase (to handle backend)

It cost me ~$25.

Two years ago, this would've cost >$50,000 to hire a programmer or dev shop.

Today, anyone can do it in a weekend, it’s nuts.

I'm thinking of doing a virtual demo + tutorial on how I built this (if there's enough demand). If you’re interested, leave a comment here.

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