We are approximately 70% through the year, and summer officially ends in a week. Where did the time go?

I recently came across a staggering statistic: a third of your life is spent at work. That means a huge share of your happiness, your quality of life, and your fulfillment comes down to your career. The right job can change your entire life, but the wrong one can drain it.

Today’s essay is about identifying the right signals to join a life-changing company.

📅 Upcoming Events

• Sep 18 | 🖥️ (Virtual) Lessons From Scaling to $1M+ Without Raising Venture Capital w/ Andrew Yeung

• Sep 28 | 🗽 The Shortlist: September Founder Showcase (NYC) – Meet the founders/CEOs of the fastest-growing tech companies in the city.

• Sep 29 | 🌇 September Tech Rooftop Mixer (NYC) – Join our must-attend event for founders, investors, and tech professionals shaping the future. Hosted at an iconic, massive venue in the heart of NYC.

• Sep 30 | 🍽️ Junto Founder Dinner (NYC) – Apply to attend. Join a handpicked group of early-stage venture-backed NYC CEOs and founders for dinner on me.

• Sep 30 | 🚀 MongoDB.local NYC – Attend to see best practices and technologies from NYC’s top AI builders. [PARTNER EVENT]

• Oct 2 | 🐶 tech pawty (NYC) – Hosting a founder coffee social at Puppysphere - an original puppy experience. Come and hang with the cutest doggos (and founders) in the city.

• Oct 4–19 | 🚀 Launchpad by Stan (NYC) – A two-week experience for aspiring founders to launch their companies in public and compete for cash prizes and capital investments from top investors. Fibe has 5 spots - use FIBE for expedited approval

• Oct 14 | 🍽️ Junto Founder Dinner (SF) – We’re back in SF! Founders and CEOs only. Michelin-starred restaurant.

• Oct 15 | 🍽️ Extraordinary Founders Dinner (SF) – Join me and a dozen vetted Series A, B, C founders for dinner at a Michelin-starred restaurant.

• Nov 5–6 | 🗽 The Outliers Summit (NYC) – Spend 2 days with the unreasonably ambitious builders in New York. Get your tickets before prices go up!

• • •

As a community builder and “super connector,” I have the privilege of not only helping people land their next role, but also seeing the patterns that emerge over time based on their career decisions.

I get asked this question constantly: How do you choose the right company to work for?

It usually comes from one of four places

1. The friend leaving a big tech job who finally admitted they're bored

2. The new grad staring at two or three competing offers, paralyzed

3. The person who is burnt out of their current role

4. Or the founder whose company just wound down, sitting in the in-between, trying to figure out the next move.

I used to be terrible at answering this because, for years, I optimized for the wrong things. I looked at the title, the salary, the big logos. And it took me a long time and a few mistakes to understand that these can be the least important factors.

I’ve spent the last few years pattern-matching and talking to executives, founders, and CEOs who eventually made the right career choices, leading to either great financial outcomes or a fulfilling pursuit of meaningful work.

These are the patterns I’ve observed that lead to successful career bets.

1. Choose the market, not the job

A counterintuitive insight: a strong market pulls success out of even the most mediocre companies.

That means the sector you choose matters more than the specific company and far more than the specific role.

Elad Gil, an early employee at Google and one of the world’s most notable venture capitalists, says that early in your career, the market trend you ride may be the single biggest determinant of your success.

A rising market means more opportunities inside your own company and more companies competing to hire you later, but a shrinking one means the opposite. So before you evaluate the company, evaluate the market. Is it growing? Do you expect it to be much larger in 5 years?

2. Optimize for the network you’re joining.

The network might be the single most important thing to optimize for in a job, yet it’s also a factor that people most consistently underrate.

Your network doesn’t only mean your manager, but the entire constellation of people around the company: The founders, early employees, investors, advisors, customers, even vendors.

A classic example is the PayPal mafia that seeded LinkedIn, YouTube, Tesla, SpaceX, and Yelp. If you were in that group, you had a career full of outside opportunities for the next few decades, no matter whether you were brilliant or just lucky.

The same is true of the early Google diaspora, who now sit at the top of every single major tech company and venture firm.

So when you evaluate a company, figure out who you’ll be surrounded by. Look at the companies. Look where the companies’ former employees end up. If the alumni go on to build and lead great things, that tells you a lot.

3. Pick the job with the highest rate of learning

Sam Altman has a rule of thumb: avoid any career where someone with 2 years of experience can be as effective as someone with 20. Your rate of learning should always be high.

The most effective environments are the ones where you feel slightly out of your depth when you’re surrounded by people who are better than you and force you to accelerate your growth just to keep pace

Pick the companies where you’re the least experienced person, not one where you’re the smartest. The old adage holds true: if you’re the smartest person in the room, you’re in the wrong room

4. Stop overrating role and compensation

If you join a rocket ship but land in a seat you don’t love, you can almost always move seats once you’re inside. Example: If you want to be a product manager but can only get hired into the operations team at a great company, take it anyway. If you’ve picked the right company, opportunities to move around will open up as it scales (But this is usually only true if you join a high-growth company).

Early on, compensation shouldn’t be an important factor either. Owning 1% of a mediocre company is much worse than owning 0.1% of a great one. One may be worth zero, while the other could be worth a thousand times more.

The same goes for cash. At a great company, your cash pay will accelerate over time because winning companies eventually pay above market. Salary seems to be what people fixate on most, but it matters least early on. Trade short-term compensation for long-term growth unless you desperately need the cash right now, which is a valid exception.

5. Weigh optionality: does this open doors?

And lastly, don’t just default to something familiar. A tangible way to define optionality is the number of future jobs the next one will unlock. Have you been doing the same kind of work in the same kind of industry over and over again, or does this next role set you up to do something new, to move into a different market or a different function down the road?

I've watched many successful operators move laterally, from product to marketing to sales, just to get breadth of experience early. In the moment, this can look disorganized, even aimless. But the truth is that with AI, most roles are converging, and entirely new categories of work are forming. Early in your career, it's better to gain breadth than to go deep.

• • •

I love talking about this more than anything, and the honest reason is that I believe finding the right opportunity can completely change your life. I’ve seen it happen too many times. Someone joins the right company at the right moment, and five years later they’re a different person. Financially, they might have the options they’ve never imagined, but it’s also so much more than the money.

P.S. I'd love to help you find your next role. Two ways I can help.

1. Are you looking to hear about roles from breakout tech companies in New York? Sign up for our talent network here to receive emails about jobs.

2. Do you want to meet founders and CEOs of the fastest-growing startups in New York? Attend our monthly Shortlist Founder Showcase.

And if you’re a founder who wants to hire top talent, please hit reply and let me know what you’re looking for.

• • •

🚀 Spend two days with the most ambitious builders in New York (Nov 5-6)

The Outliers Summit is almost here. Two days in NYC, November 5 and 6, with the founders, operators, and builders who took the unconventional path, and the people about to.

This year’s speakers include Sam Parr (The Hustle), Carina Hong (Axiom Math), Ryan Hoover (Product Hunt), Sahil Lavingia (Gumroad), Andy Dunn (Bonobos), Zach Sims (Codecademy), Nat Eliason (Founders School), Nik Sharma, and Nadya Okamoto (August).

Built for the unreasonably ambitious builders, creators, business leaders who want to build something extraordinary.

• ​Day 1 (Nov 5): Tactical sessions where you leave having built the thing yourself – an app, an agent, an audience, a brand.

• Day 2 (Nov 6): Off-the-record conversations about the bets and mindsets that separate outliers from everyone else.

Heads up: ticket prices go up in a week, and only a limited number remain.

👉 Grab your ticket here

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• ✍️ Your AI Head of Content. I've been using Stanley for months, and it's the only reason I could run two companies and still grow 100K+ followers this year. It texts me what to post, tells me what's working, and auto-schedules everything from my iMessage. Free to try for 30 days with code ANDREW, here.

• 💼 Hiring top GTM & engineering talent in NYC? Apply to pitch at our monthly Shortlist founder showcase and meet the top 1% operators from my network.

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

• 💡 Sitting on a startup idea that won’t quit? Forum Ventures is accepting applications for The Foundry, their five-week studio sprint where you get access to their internal validation and diligence process to find out if your idea is a real B2B company. No cost to participate, and a shot at a $250K investment. Apply 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.

• 🏦 Fidelity Private Shares is 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.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 💸 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.

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

• • •

🖼️ Behind the Scenes

I’m grateful to Fast Company for featuring me in their editorial report on the new rules of personal branding. You can read the full article here.

Two things on personal branding are worth sharing here:

1. Building a personal brand is like playing the internet lottery. Publish something once, and you never know; you might end up reaching millions of people and changing the entire trajectory of your career. Worth a shot.

2. Some people think personal branding is cringe. But the biggest difference I've noticed between the people who do it and the people who don't is this: the ones who do care enough to try. They care about their craft. They care about their career. They care about the outcome. And I've come to believe there's almost nothing more admirable than watching someone put themselves out there and go for something.

Publishing this with gratitude from Copenhagen, Denmark. My favorite type of essay that I write all year. Enjoy!

📅 Upcoming Events

• Sep 8 | 🍸 GTM Cocktail Hour - hosted by The Shortlist & viktor.com (NYC) – An evening for the top GTM professionals (AEs, customer success, growth, marketing & community).

• Sep 10 | 🍽️ AI & Marketing Salon #5 (NYC) – Apply to attend. Co-hosted with Kamal (SVP Marketing at Invisalign).Join a dozen CONSUMER marketing execs (CMO, VP) for dinner.

• Sep 14 | 🍽️ Junto Founder Dinner (NYC) – Apply to attend. Join a handpicked group of early-stage venture-backed NYC CEOs and founders for dinner on me.

• Sep 17 | 🖥️ (Virtual) The IRL Advantage: How to Turn In-Person Connections into Lasting Relationships w/ Goodword

• Sep 18 | 🖥️ (Virtual) Lessons From Scaling to $1M+ Without Raising Venture Capital w/ Andrew Yeung

• Sep 28 | 🗽 The Shortlist: September Founder Showcase (NYC)

• Sep 30 | 🍽️ Junto Founder Dinner (NYC) – Apply to attend. Join a handpicked group of early-stage venture-backed NYC CEOs and founders for dinner on me.

• Sep 30 | 🚀 MongoDB.local NYC – Attend to see best practices and technologies from NYC’s top AI builders. [PARTNER EVENT]

• Oct 2–17 | 🚀 Launchpad by Stan (NYC) – A two week experience for early stage founders to launch their companies in public and compete for cash prizes and capital investments from top investors. [PARTNER EVENT]

• Oct 14 | 🍽️ Junto Founder Dinner (SF) – Founders and CEOs only. Michelin-starred restaurant.

• Oct 15 | 🍽️ Extraordinary Founders Dinner (SF) – Join me and a dozen vetted Series A, B, C founders for dinner at a Michelin-starred restaurant.

• Nov 5–6 | 🗽 The Outliers Summit (NYC) – Early bird ends tomorrow (Sep 1)

• • •

I turn 31 today. Usually on my birthday, I write a "30 things I learned”, but this year, I'm switching it up to write about the things I changed my mind about instead.

I believe part of maturing is developing the capacity to change your perspective based on new information. I’ve done that a lot this year, and these are the ideas that stuck with me.

And as always, thank you to my friends who are far wiser than I am, and from whom I stole most of this.

You can do anything, but not everything

A good friend of mine is a true multi-hyphenate. He started a company, runs a venture capital fund, published multiple books, teaches at a business school, and more. He recently confided in me that he regrets doing so much. If he had the temperament to just focus on one thing, he would’ve been far more successful.

This isn't unique to him. I hear it constantly from entrepreneurs. In a world with an infinite number of shiny objects, focus is a superpower. One year of obsession can change your life, forever.

Giving without expectation is a recipe for getting walked all over

“Give without the expectation of return” used to be my personal mantra - I even wrote about it in my essay last year. I tried to follow this rule for the first decade of my career, and it led to positive outcomes, new opportunities, and many new friends - but it also burned me more than a few times.

I would love to live in a world where everyone is a giver, and a generous, positive-sum thinker, but my scar tissue has taught me that it is not the case. Takers are not familiar with reciprocity, and unfortunately they outnumber givers. So I’ve revised my philosophy.

I adopted Brad Feld's (founder of Techstars) mantra instead, after meeting him this year: Give First. But strategically. Give to the people you trust to reciprocate eventually.

Overoptimizing is a trap

Taking anything to an extreme often gives you disproportionately bad trade-offs.

Being a health nut means skipping the cake you’d have loved. Being a longevity-obsessed biohacker who wants to live forever means skipping the late nights with old friends, and the experiences that pay memory dividends for life.

And grinding 100 hours a week on your startup slowly turns you into an out-of-touch, one-dimensional person who can only think about AI agents.

There's a great line from Star Wars: "Only a Sith deals in absolutes."

Entrepreneurship isn’t always the highest form of career leverage

I no longer believe everyone should start a company or that it’s the most efficient path to financial freedom.

Yes, the wealthiest people I know are entrepreneurs. But that doesn’t account for survivorship bias (for every person who succeeded massively, 99 did not) or the decades of sacrifice they poured in.

Building a company used to be the best way to build equity or get outlier financial outcomes. But the last three years have shown that you can now get founder-level equity without taking founder-level risk (see: AI companies).

Shameless plug: if you’re in New York, I started a thing this year, The Shortlist, where we put the founders of these upstarts right in front of you. I’m betting that these companies will be the next generational tech companies.

Character is a choice, not a requirement

When I was younger, I believed in karma. What do I mean exactly? Well, I wanted to believe that to be successful in the long term, you had to be an honest, kind, and ethical person.

The startup world taught me otherwise. I’ve seen all types of characters win, and watched unkind, dishonest people end up with the kind of rare success we all long for. The harsh truth is that temperament, ethics, and values have nothing to do with someone’s capacity to succeed in business, especially in entrepreneurship.

So I’ve learned to separate business success from personal success. They aren’t the same thing, and one doesn’t earn you the other. I’d rather be a good, high-integrity person, win or lose. That’s a choice available to all of us, no matter how the business turns out.

Spending well is as important as saving well

Growing up in an Asian household, I watched my parents save every penny, which taught me to do the same. And it made sense in the first few years of my career, as I was just starting to build a little wealth for myself.

But I mistakenly carried the same habits into my 30s, even though my financial situation has changed, and it drives me crazy. It clouds my decisions and makes me miss opportunities, both personally and professionally.

Not knowing how to spend your money well can be just as detrimental as not knowing how to save.

P.S. Two books that changed my perspective on spending: Die With Zero and The Art of Spending Money.

The wisdom of biting your tongue

My parents always taught me to be honest, so I’ve always spoken my mind. With friends, in meetings, with my employees. I always believed it was the high-integrity thing to do.

It took me until my 30s to realize the importance of biting my tongue.

Two lessons:

1. Not everyone wants feedback, no matter how much it may help them.

2. Give yourself 24 hours before sending any emotionally charged email (excited, happy, disappointed, angry, whatever it is).

Not everyone has to like you

We all want to be loved. It’s human instinct. I used to believe that to be happy and successful, you needed everyone to love you.

It’s not true. When someone doesn’t like you, nothing actually happens. The world doesn’t end. And the more at peace you become with being disliked, the more freedom it gives you.

Sometimes the harder path is the least crowded one

Braess's paradox states that adding more roads to a network can actually create more congestion.

The same is true for careers. When everyone crowds onto the lower-effort path, it gets competitive and eventually harder for everyone on it. So the most efficient move is often to do the harder thing instead.

When I started my first events company in 2023, more than a dozen people questioned it. How will you scale? What about the margins? Why not build an AI company like everyone else? Nobody was doing what I was doing at the time. But it worked, and it’s still working, beyond anything I expected.

Start the harder business. Pick the tougher obstacle course. Take the more difficult job. Sometimes the easiest way to beat the competition is to go where there isn’t any.

You get more than six shots

Last year, I wrote that you get four to six shots to do something meaningful in a 30-year career, because anything worthwhile takes an average of five to seven years.

I was wrong. AI has dramatically compressed timeframes. You can build a beautiful piece of software in just an hour. You can go viral overnight with millions of views. You can master a discipline in months by self-learning. If you have agency, you can now live multiple lives in the time it used to take to live one.

It might look stupid in the beginning

During a time when the hottest companies in the world were social media platforms, a friend started a company selling dog treats and toys, delivered to your home every month. Years later it was doing more than $500M a year in revenue, and he IPO’d it in 2021. Another friend sold well-fitting men’s pants online. Everyone wondered why. Less than a decade later, he sold it to Walmart for $310M.

I’ve learned to lean in more when something makes me wonder “wait, why would anyone do that”.

The best ideas almost always look strange at the start, because if they were obvious, someone else would already be doing them. Everything looks weird until it works.

There are only two ways to slow time down

I spent the first half of 2026 obsessing over how to slow time down. It’s stupid, I know, but I think I felt too young to be turning 30 (and now 31).

I’ve learned there are only two real ways to slow time down:

• Travel and new experiences.

• Doing hard things. Long runs, tough workouts, learning a skill that challenges you.

Which, I suppose, is the whole reason I write these every year. Slowing down long enough to notice what actually changed.

31 feels good. I’m the healthiest, happiest, and most focused I’ve ever been. And I’m grateful to be here in your inbox. Thank you for reading these, for showing up to my events, and for growing alongside me.

See you out there.

• • •

🚀 Last call: Outliers Summit early-bird ends tomorrow (prices jump 30%)

Early-bird pricing for the Outliers Summit ends tomorrow, September 1 at 11:59 PM EST, and then ticket prices go up 30%.

This year’s format: Two days in NYC (November 5 and 6) with speakers like Sam Parr (The Hustle), Carina Hong (Axiom Math), Ryan Hoover (Product Hunt), Sahil Lavingia (Gumroad), Andy Dunn (Bonobos), Zach Sims (Codeacademy), Nat Eliason (Founders School), Nik Sharma, and Nadya Okamoto (August).

Built for the unreasonably ambitious builders, creators, business leaders who want to build something extraordinary.

• ​Day 1 (Nov 5): Tactical sessions where you leave having built the thing yourself – an app, an agent, an audience, a brand.

• Day 2 (Nov 6): Off-the-record conversations about the bets and mindsets that separate outliers from everyone else.

👉 Get early bird tickets here (only a few remain)

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 💼 Hiring top GTM & engineering talent in NYC? Apply to pitch at our monthly Shortlist founder showcase and meet the top 1% operators from my network.

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

• 💡 Sitting on a startup idea that won’t quit? Forum Ventures is accepting applications for The Foundry, their five-week studio sprint where you get access to their internal validation and diligence process to find out if your idea is a real B2B company. No cost to participate, and a shot at a $250K investment. Apply 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.

• 🏦 Fidelity Private Shares is 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.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 💸 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.

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

• • •

💸 Affiliates

Founders, make $$$ by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.

• Rho (up to $550) – All-in-one banking and financial automation platform for startups.

• Superpower (up to $120) – A proactive health platform that tests 100+ biomarkers annually to detect early signs of 1,000+ conditions — giving individuals and teams actionable health intelligence for $17/month.

• Highbeam (up to $350) – AI financial command center for consumer brands.

• Numeral (up to $1,670) – AI for sales tax and compliance across states and countries.

• North.Cloud (up to $500) – Cut AWS and GCP costs.

• WithCoverage (up to $710) – A modern risk management for consumer-focused businesses. 1,000+ customers with 99.9% retention.

• Secure Cloud Innovations ($310) – An embedded cybersecurity consulting/consulting team for B2B SaaS companies.

• Corridor ($550) – AI-Native health insurance brokerage for startups & small businesses (5-500 employees).

• • •

🗽 (Sponsored) MONGODB.LOCAL NYC – SEP 30

New York City’s top AI minds are building what’s next, and MongoDB is bringing them together at .local NYC.

MongoDB.local NYC is your competitive edge for building production-grade AI. Join venture-backed founders, CTOs, and principal engineers for a full day of technical blueprints, agentic AI architecture, and unvarnished lessons on scaling past the demo phase on Sep 30 in NYC.

Passes for founders are fully covered, but capacity at Pier 36 is limited to ensure high-impact networking. Here is what is on deck:

👉 Apply for Founders Pass

• • •

🖼️ Behind the Scenes

Currently in Copenhagen, Denmark, and I've been fascinated by this building since reading about it ten years ago and finally got to see it in person the other day.

It's called Tietgenkollegiet, one of Copenhagen's most interesting buildings. And it's a student dorm. It's basically an experiment in whether architecture can make strangers become friends.

~390 students live here. Private bedrooms face outward, while the shared spaces, kitchens, lounges, etc. face inward toward a huge central courtyard.

So you can literally see other people cooking, hanging out, and gathering across the courtyard. Instead of telling people to “build community,” the architecture makes it happen naturally.

I would've LOVED to live here as a student. Also, what a fascinating place!

It’s my last day in SF today but I’ll be back in October. Tomorrow I head to Atlanta, then following that, back to New York then Copenhagen. Enjoy today’s article and our upcoming events programming.

I’m also actively making angel investments, so if you are raising your first or second round, please hit reply to tell me what you are building. I will respond if it’s a fit.

📅 Upcoming Events

• Aug 18 | 💻 The AI Dev Stack: Beyond Code (SF) – Join Fireworks, Braintrust, Browserbase & Antimetal for an evening on how AI is changing the way software gets built, shipped, and maintained. Not my event but highly recommended.

• Aug 19 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• Aug 20 | ☕ Breakfast & Fireside Chat w/ Henrik Werdelin, Founder of BarkBox (NYC) – With my friend, Henrik, the founder of BarkBox (NYSE: BARK) to discuss building companies in the AI era.

• Aug 20 | 🍽️ AI & Marketing Salon #4 (NYC) – Salon dinner to discuss the future of marketing. We have two seats left for CMOs & VPs of Marketing.

• Aug 25 | 🌇 August Tech Rooftop Mixer (NYC)

• Sep 1 | 🖥️ (Virtual) Mindsets of $1B Founders w/ Ankur Nagpal & Andrew Yeung – With my friend Ankur, who sold his first company Carry for $250M and is now a General Partner at AngelList’s USVC fund.

• Sep 3 | 🖥️ (Virtual) Lessons From Scaling to $1M+ Without Raising Venture Capital w/ Andrew Yeung

• Sep 10 | 🍽️ AI & Marketing Salon #5 (NYC) – Salon dinner to discuss the future of marketing. We have ten seats for CMOs & VPs of Marketing. Special guest to be announced!

• Sep 17 | 🖥️ (Virtual) The IRL Advantage: How to Turn In-Person Connections into Lasting Relationships w/ Goodword

• Oct 14 | 🍽️ Junto Founder Dinner (SF) – Founders and CEOs only. Michelin-starred restaurant.

• Oct 15 | 🍽️ Extraordinary Founders Dinner (SF) – Join me and a dozen vetted Series A, B, C founders for dinner at a Michelin-starred restaurant.

• Nov 5–6 | 🗽 The Outliers Summit (NYC)

• • •

Lessons From Scaling to $1M+ Without Raising Venture Capital (Pt. 1)

I never wanted to be an entrepreneur. Instead, I fell into it while trying to solve a problem for myself that apparently many others had. I didn’t raise a dollar of venture capital nor did I have a check from my trust fund (in fact, my parents pleaded with me NOT to quit my job at Google). And I didn’t have a co-founder, advisors, or a board either.

To date, Fibe has generated millions of dollars in profit, and earlier this year I started another company, The Shortlist, to help startups find the best talent, which has just begun to hit profitability. I also co-founded the Outliers Summit, which operates independently as a profitable events and media company and will soon hit the 7-figure mark.

The best part: I spend my time doing work I love, bringing people together and creating content. For the most part, I answer to nobody, and I own my companies outright.

I believe that most entrepreneurs should consider bootstrapping before other options, but I don’t think bootstrapping is morally superior to raising money in any way. Raising is the right call when you're going after a winner-take-all market, or when you need capital to reach escape velocity, but most people default to raising as their first instinct, when the truth is that most businesses don't need it. Mine didn't.

Also, before we get into it: I'm hosting a live webinar on September 3 where I'll go even deeper on everything in this piece. How I bootstrapped to seven figures, the games worth playing, the mistakes to avoid, and the systems that make it all run. It'll be part teaching, part live Q&A, so bring your questions.

👉 Sign up here

Here are the ten lessons I learned scaling my business to $1M+ without taking money from investors. Part one!

• • •

1. Pick your game before you start

The most important decision you’ll make is what game you’re playing, and most people never consciously make it.

Do you want to build a billion-dollar tech company? Do you want to be venture-backed? Do you want to run an agency or consultancy? Or sell physical products as a direct-to-consumer eCommerce company? How about building apps? Or do you want to be a content creator?

Each game has completely different rules, economics, and outcomes. Advice that is gospel in one game might be malpractice in another. A friend who's opening a rock-climbing gym asked me for business advice, and I was honest: I have absolutely no clue.

Before you start, it’s helpful to map out the trajectory of the business through branching logic. Where does it lead? What does year five look like? What kind of life does the CEO have?

You should pick the type of business you start based on the life you want, not the other way around.

I knew that I did not want to (1) raise venture capital or (2) run an agency because I had never met someone who did those things and felt they were genuinely free - and independence is my most important value.

2. You probably don't need to raise money

Too many entrepreneurs treat raising money as step one - as their first instinct the moment they decide to start. Usually it’s driven by fear.

But most businesses do not need outside money beyond, at most, a small initial round to have a cushion. Call it $50,000-$100,000. Plenty of businesses need nothing at all. I didn’t raise anything. I funded the business with the revenue.

If it’s your first time building something, the trick is to choose a model that doesn’t require a big upfront investment or a long break-even period. Media companies, service companies, and software businesses can often start generating cash almost immediately. Restaurants and brick-and-mortar retail can’t. There are more than enough business models that let you skip that pain entirely. Pick one of those.

3. Start while you still have a cushion

The best way to start a business (especially if it’s your first) is to start before you need it to work.

Build it on the side while you still have a W2 job or another source of income. When you’re not dependent on the business making money next month, you make better decisions. You don’t take bad clients or bad terms out of fear. You give the thing room to find its footing. You’re not desperate.

Desperation is expensive and forces you to make choices from a weak position.

4. In the early days, you are the business

In year one, there is no separating you from the company. You are the product manager, the sales team, the marketing department, the support desk.

That means two things:

First, finding customers is everything. In the early days, you should orient almost all of your time around finding customers, serving them well, and building a business model that makes economic sense. Nothing else matters as much.

Second, because you are the business, taking care of yourself is a business decision. Your physical health (hardware) and your mental health (software) are all company infrastructure. If you break down, the company breaks down. Do not neglect sleep, nutrition, rest, and exercise.

5. Social proof is critical early

When you’re new, your customers have nothing to judge you on.

So they quickly form impressions based on your social proof, brand, and credibility. These first impressions are extremely hard to change later.

So you need to provide as much proof as possible. Display testimonials, show logos, and capture photos from your events. Every piece of proof you collect early keeps working for you long after.

6. Distribution > Product

An average product with a loyal audience beats a great product with no audience every single time. This is MORE important than ever with the commoditization of software.

I started building an audience on LinkedIn in 2019, and this is the single biggest reason I was able to bootstrap. I spent years building an audience before I had a business idea. Greg Isenberg even has a helpful framework called Audience, Community, Product (ACP).

One thing to look out for: Building an audience in service of your business is one of the highest-leverage things you can do. BUT trying to be a full-time content creator and a serious entrepreneur at the same time is a trap. Content is seductive and distracting, and I’ve watched many founders quietly optimize for vanity metrics, likes and followers, instead of building a good business underneath.

Build the audience to feed the business. Don’t let the audience become the business unless a media company is the game you’ve chosen to play.

7. Solve expensive problems for customers who can pay

This is the advice that experienced entrepreneurs tell me over and over again.

The reason most entrepreneurs prefer B2B to B2C is that businesses have much more money to spend than everyday consumers. A small business will spend tens of thousands of dollars on painkillers to help it run. The average consumer, by contrast, might complain about paying $20/month for a subscription.

I decided early on not to go the consumer route - that is, we host 100+ events a year, but 99.9% of them are free. The only event that is ticketed is our Outliers Summit and that’s because it’s a multi-day event with many experiences included. I wanted to sell to enterprises that would not think twice about writing a $50,000 check, such as banks, law firms, recruiting companies, software companies, and many more.

The same amount of effort spent serving customers with money returns far more than serving customers without it.

8. One channel is enough to reach one million dollars

I learned this from building my own company and from advising a dozen other early-stage startups. All you need is one marketing or sales channel to reach a million dollars in revenue. Often, that’s LinkedIn for B2B and TikTok for B2C.

Think about that for a sec: You can generate a million dollars of revenue for your company by posting on LinkedIn or making videos on TikTok. You have to be good at it, of course, but getting there might only take you a few months.

Don’t chase five marketing channels too early. Pick one where you have an unfair advantage and go deep before you go wide. Then build referral and affiliate loops on top of it and incentivize your happy customers to bring you more customers.

9. Spend on marketing only when it ties to revenue

In the early days of your business, CUSTOMERS are the lifeblood of your business, and every dollar you spend should trace back to them.

Tie every single marketing dollar to an outcome. Performance marketing is great because it’s measurable. The same logic extends to channels that are tangible, like hosting a dinner for prospects.

What you want to avoid early is spending on brand for brand's sake, before you've proven you can turn attention into customers.

10. Stay lean and sell the mission

It’s impossible to be competitive on compensation as a small business, so you have to offer the intangibles. Things like mentorship, team, learning, and experience, or selling the company's mission incredibly well.

At Fibe, we believe in the concept of a “tour of duty” - work with us for 12 to 18 months in a demanding, high-intensity role, and we'll amplify your personal brand and make sure you're well-networked with the most influential people in tech. That's why many of our team members now have tens of thousands of followers on LinkedIn and are close with dozens of founders, CEOs, and CMOs.

You want people who are there for the mission, not people optimizing for a paycheck you can't match.

Two more things:

Before you hire someone to do a job, you should first do the job yourself and understand it before you can delegate it. Then lean on part-time people, contractors, and interns before you commit to full-time headcount.

Use AI relentlessly. It has transformed what a small team can do. You can now automate huge amounts of coordination, logistics, scheduling, and even design. This is a big part of how we run over a hundred events a year with a tiny team.

Where this leaves us (and what's coming in Part 2)

Everything in Part 1 was about the foundation - picking the right game, avoiding the reflex to raise, staying lean, and understanding what kind of business you’re building.

But choosing the right business is only half of it. Running it well is a different skill entirely.

That’s what Part 2 is about. The lessons I learned once the business was already off the ground, and the mistakes I made along the way so you don’t have to repeat them.

See you there

…

Oh, and if reading this made you want to be in a room full of people building interesting things, come to the Outliers Summit on November 5 and 6 in New York.

It's two days with founders, operators, and builders who took the unconventional path, many of whom bootstrapped their way to something meaningful.

Day one is how outliers build. Day two is how outliers think. If you've been circling the unconventional path, the fastest way I know to get onto it is two days around people already on it.

👉 Get early bird tickets here (only a few remain)

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 💼 Hiring top GTM & engineering talent in NYC? Apply to pitch at our monthly Shortlist founder showcase and meet the top 1% operators from my network.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 🍽️ 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 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.

• 🚀 Forum Ventures just opened applications for their next Builders Between Ventures cohort. Three weeks to find out if your idea is a real company, no cost, no equity, and a real shot at a $250K investment. Apply 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.

• 🏦 Fidelity Private Shares is 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.

• 💸 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.

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

• • •

🤝 You’ve built an incredible network. Now use it.

Part of my mission is to help you build deep, meaningful relationships. That’s also why I became an angel investor in Goodword.

Goodword is the modern relationship manager. It helps you remember the context behind every relationship and stay meaningfully in touch long after the dinner, mixer, or conference ends.

Friends of Andrew can get $100 off an annual subscription: $199 instead of $299. Start your free trial at goodword.com and use code FRIENDOFANDREW at checkout.

• • •

💸 Affiliates

Founders, make $$$ by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.

• Rho (up to $1,350) – All-in-one banking and financial automation platform for startups.

• Superpower (up to $240) – A proactive health platform that tests 100+ biomarkers annually to detect early signs of 1,000+ conditions — giving individuals and teams actionable health intelligence for $17/month.

• Highbeam (up to $1,750) – AI financial command center for consumer brands.

• Numeral (up to $2,150) – AI for sales tax and compliance across states and countries.

• North.Cloud (up to $500) – Cut AWS and GCP costs.

• WithCoverage (up to $750) – A modern risk management for consumer-focused businesses. 1,000+ customers with 99.9% retention.

• Secure Cloud Innovations ($250) – An embedded cybersecurity consulting/consulting team for B2B SaaS companies.

• • •

🖼️ Behind the Scenes

Pups and I made it on a Times Square billboard!

I started this bi-weekly email newsletter six years ago, and all the great things in my life have come from it.

And earlier this year, I started the Shortlist NYC newsletter too, which I’ve built exclusively on beehiiv. Every week we share the top startup jobs in New York that you should know about. See it here.

I’m grateful to beehiiv for championing creators and have a ton of admiration for Tyler Denk as a founder.

I hope you’re having a great summer.

I’ve spent the past few weeks behind a screen, building things and tinkering with AI and am eager to share a few things later this year.

Meanwhile, I’m in San Francisco, Atlanta, Copenhagen, Madeira, and Mexico City in the coming weeks. If you’re around, send me a note!

I’m also incredibly excited to share our jam-packed upcoming events lineup in NYC/SF for founders, marketers, builders, and more. Apply below.

📅 Upcoming Events

• August 6 | 🍽️ Extraordinary Founders Dinner (SF) – Join me and a dozen vetted Series A–C founders for dinner at a Michelin-starred California native restaurant. We have ONE spot left.

• August 7 | 🥪 Lunch Club w/ Andrew Yeung (SF) – One of my favorite things to do is to take ambitious young people to lunch wherever I travel. If you're a recent grad or student (hs or university), I'd love to meet you (see the post for instructions).

• August 19 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• August 20 | ☕ Breakfast & Fireside Chat w/ Henrik Werdelin, Founder of BARK (NYC) – Application only. An intimate breakfast and private Q&A with Henrik, the founder of BARK about building companies in the AI era. BARK was a category defining DTC company that went public (NYSE: BARK) in 2021.

• August 20 | 🍽️ AI & Marketing Salon #4 (NYC) – A curated, salon-style dinner to discuss the future of marketing. We have seats for twelve CMOs/VPs of Marketing.

• August 25 | 🌇 August Tech Rooftop Mixer (NYC) – Hosted at a stunning venue in Williamsburg with skyline views.

• September 10 | 🍽️ AI & Marketing Salon #5 (NYC) – A curated, salon-style dinner to discuss the future of marketing. We have seats for twelve CMOs/VPs of Marketing. Special guest to be announced.

• October 14 | 🍽️ Junto Founder Dinner (SF) – Founders and CEOs only.

• October 15 | 🍽️ Extraordinary Founders Dinner (SF) – Join me and a dozen vetted Series A, B, C founders for dinner.

• November 5–6 | 🗽 The Outliers Summit (NYC)

• • •

Introducing the Outliers Summit

I spent the first five years of my career clueless, not knowing what I wanted to do with my life.

At the time, I thought that joining one of the big tech companies in the world would give me a sense of accomplishment and direction, but no, it did not.

So I moved to New York, because I had a hunch that the most ambitious people in the world were building here. My hunch was right.

In 2020, I started hosting events mostly so I would have a reason to meet people, and through them I met founders, CEOs, and builders that I did not know existed, building things I did not know were possible to build.

Being in close proximity to such ambitious people made me want to go build my own thing, so I did – and it changed my life completely. Surrounding myself with such relentless people gave me the agency to build an audience, a reputation, friendships I still have, and a business that has made me millions of dollars doing work I actually love – bringing people together.

It’s like being given a map to a maze that I never knew existed, and once I saw what is possible, I never went back. And it’s a gift I’ve been trying to give others ever since.

So in 2024, I called up my friend Ankur Nagpal, one of the most brilliant and well-connected people I knew, and pitched him the idea of doing a summit bringing together extraordinary people.

So we came up with the idea of the OOO Summit (Owners, Operators, Outliers), and over 600 people attended our first Summit. It blew my expectations away.

In 2025, we more than doubled it. Over 3,000 people attended over the week and over 800 at the main event.

Over those two years, the stage has held Guillermo Rauch (Vercel), Andrew Yang, Sahil Bloom, Sam Parr, Alex Lieberman, Packy McCormick, Nathan Barry, Steph Smith, Justin Welsh and Kyla Scanlon, among many others.

I will be honest with you: it is the hardest, most stressful thing I’ve ever done, especially with a small team, but it is the most meaningful thing I’ve done in my career.

But every year, it’s worth it because I keep meeting people who started a company after sitting in that room.

Which brings me to today.

We called it the OOO Summit, for Owners, Operators, and Outliers. That name is no longer relevant.

Why:

The people showing up are not only business owners and operators. There are entire categories of work that did not exist when we picked that name. Multi-hyphenates. Hybrid creators. Solo builders. People running companies of one with agents doing the rest. Careers nobody has a title for yet.

So today, the OOO Summit becomes the Outliers Summit.

I define an outlier as someone who chose the unconventional path in their discipline, someone who is unreasonably ambitious about what they are building. Most people optimize the path they were handed. Outliers go find a different one. If that is you, we’d love to have you.

We’re also doubling the size of our Summit this year. Two days instead of one.

• Day 1, November 5. How Outliers Build. Tactical sessions across the disciplines you need in the AI era. You leave having built the thing yourself. An app, an agent, an audience, a brand.

• Day 2, November 6. How Outliers Think. Candid, off-the-record conversations about the bets and mindsets that separate outliers from everyone else.

This year we’ve confirmed Ryan Hoover (Product Hunt, Weekend Fund), Sahil Lavingia (Gumroad), Andy Dunn (Bonobos, Pie), Nadya Okamoto (Pie, August), Zach Sims (Codecademy), Nik Sharma, Nat Eliason, and many more to be announced.

Over the week, we expect over 4,000 people from 3,000 companies to attend.

Data from previous years:

• 54% are founders, C-suite, VPs or investors

• 39% are founders and CEOs specifically

• 48% of founders have raised $1M or more

• The average founder has raised $5.9 million.

The operators who attend come from companies like Google, Meta, Amazon, Microsoft, Stripe, Ramp, Notion, Palantir, Goldman Sachs, a16z, Thrive and Bessemer, and from the several thousand startups that make up the rest of the room.

Hosted by Ankur Nagpal and me in partnership with AngelList.

🎟️ Early-bird pricing ends August 12, and prices go up 30% after that. Two-day passes are $149.

If you have been circling the unconventional path, the fastest way I know to get onto it is two days around people already on it.

👉 Grab your pass here: https://outlierssummit.com/

P.S. if you’re interested in being a sponsor or partner of this event, just hit reply and send me a note!

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 🍽️ 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 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.

• 🏦 Fidelity Private Shares is 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.

• 🚀 Forum Ventures just opened applications for their next Builders Between Ventures cohort. Three weeks to find out if your idea is a real company, no cost, no equity, and a real shot at a $250K investment. Apply here.

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

• 💸 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.

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

• • •

💸 Affiliates

Founders, make $$$ by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.

• Rho (up to $1,350) – All-in-one banking and financial automation platform for startups.

• Superpower (up to $240) – A proactive health platform that tests 100+ biomarkers annually to detect early signs of 1,000+ conditions — giving individuals and teams actionable health intelligence for $17/month.

• Highbeam (up to $1,750) – AI financial command center for consumer brands.

• Numeral (up to $2,150) – AI for sales tax and compliance across states and countries.

• North.Cloud (up to $500) – Cut AWS and GCP costs.

• Turing ($200) – AI to match companies with elite, pre-vetted remote software engineers.

• WithCoverage (up to $750) – A modern risk management for consumer-focused businesses. 1,000+ customers with 99.9% retention.

• Secure Cloud Innovations ($250) – An embedded cybersecurity consulting/consulting team for B2B SaaS companies.

Writing this on the flight back from Mexico City, where I spent two weeks. It’s a wonderful place, but I’m excited to come back to New York to host a series of events I’m ecstatic about.

We have five events at the end of July, including a founder fitness event at Tone House, plus our next tech rooftop mixer, founder dinners, and, of course, the next Shortlist founder showcase. Then I’m off to San Francisco to host another fancy dinner for Series A, B, and C founders (last month we were at the Michelin-starred Niku Steakhouse).

Also, excited to share some big news soon.

See you around.

📅 Upcoming Events

• July 21 | 💼 The Shortlist: July Founder Showcase (NYC) – Meet the founders of the fastest-growing startups in New York who are hiring.

• July 22 | 🌇 July Tech Rooftop Mixer (NYC) – Join us for an evening with hundreds of founders, operators, and friends in tech for skyline views and cocktails.

• July 24 | 🏃‍♂️ Founder Strength Club (NYC) – Meet other founders and get a social workout in at Tone House with us.

• July 28 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• July 29 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• August 6 | 🍽️ Extraordinary Founders Dinner (SF) – Round two. Join me and a dozen vetted Series A–C founders for supper (last month, we hosted at a Michelin-starred steakhouse).

• • •

Six years ago, I was hopelessly lost in my career. I was stuck in a dead-end job, with no clue what I wanted to do next and no idea how to navigate the uncertainty.

Every morning, I woke up unsure of who I was becoming, and it was one of the most disorienting periods of my life.

I went through a dark twelve months, for which I now have a term: the Abyss.

Since then, I’ve talked to dozens of people going through the same thing. Entrepreneurs who just sold their companies, people navigating career transitions, creatives wandering through in-between periods.

A few weeks ago, I hosted Mark Pincus, the founder of Zynga, for breakfast with our community and asked him questions about careers and building companies. Pincus pioneered social gaming, took Zynga public in 2011, and later sold the company in a deal valued at $12.7 billion. He was also the person who taught me the idea of the Abyss.

He recently published a new book, “Life at the Speed of Play,” and in it he credits the Abyss with shaping his idea for Zynga. Mark went through two of them in his career and credited both with developing the instincts that helped him build his companies. He coined the term to describe a space where you’re not actively working on something.

I put together some of the most practical advice I’ve found on navigating the abyss. If you’re stuck and unsure of what to do next, I hope it helps.

• • •

Step 1: Stop calling it failure

The first thing you should do is stop labeling this period as a failure.

The Abyss is a necessary period of slowness and reflection. If you’re in it, you’re in good company. Every single successful person I know has been in it at least once.

But here’s the thing to keep in mind: you should not be in a rush to get out.

After Steve Jobs was fired from Apple in 1985, he spent a decade in what people now call his wilderness years. He founded NeXT, which flopped, then bought Pixar for $5 million, and invested personal capital into it for years before it took off. When he returned to Apple in 1997, Jobs said that getting fired had been the best thing that ever happened to him. He couldn’t have built the iPhone without that decade away.

Sara Blakely spent two years selling fax machines door-to-door before she came up with the idea for Spanx. Reid Hoffman took over a year between the PayPal acquisition and founding LinkedIn. Jeff Bezos spent a year researching internet trends at his hedge fund before he had the conviction to leave and start Amazon.

My friend Henrik Werdelin, the co-founder of BarkBox (NYSE: BARK) and Prehype, has spent a lot of time thinking about this period. He specifically calls this the in-between period.

His advice: Don’t rush to escape the in-between. Your instinct might be to sprint toward “the answer” because everyone keeps asking “what’s next,” and when you don’t have one, the whole period feels like a failure or wasted time. It’s neither. It’s where the transformation happens. So don’t design your life to escape it. Design your life to stay in it a little longer.

• • •

Step 2: Become a flâneur

During his first Abyss, Mark Pincus became obsessed with making the perfect Bolognese sauce (which he talked about at length during our breakfast!). He went to Italy, ate Bolognese at every meal, and worked on his recipe for years. But he wasn’t trying to become a chef. He was training himself to develop the taste (pun intended) for recognizing when something works.

A friend of mine, Eddy, shared an old idea at dinner that reinforces this way of thinking. In Paris in the 1860s, a poet wrote about a figure called the flâneur. The flâneur is the wanderer who strolls a city with no destination, just observing everything and stopping to smell the roses.

To the outside world, the flâneur looks lazy. But a philosopher argued that this type of wandering was actually a form of deep perception – the flâneur isn’t wasting time; they’re learning the patterns and details that people rushing to a destination never see.

There are other ways to become a flâneur too. One of them is by sampling new disciplines.

In practice, some of the most valuable ways to sample new identities include participating in fellowships (like our program at Fibe), apprenticeships, advisory roles, and fractional work. These give you exposure to new fields without the cost of a full commitment.

Personally, I find a lot of value in advising companies, working on new projects with other entrepreneurs (my new business, The Shortlist, started as a hobbyist project), and even angel investing, where I can play a small role in helping the company in exchange for a front-row seat to see how companies are built.

Try a few things you normally wouldn’t try, and pay attention to the ones that pull you in.

• • •

Step 3: Stay in a state of readiness

A year ago, I caught up with Sahil Bloom for coffee. Sahil is a writer, entrepreneur, investor, and creator with 3M+ followers, and the author of the bestseller “The 5 Types of Wealth.” He seemed to have it all figured out, so I asked him the question I ask everyone who seems a few steps ahead:

“What’s next for you? How do you plan your career?”

He gave me an honest answer. He doesn’t know, and he doesn’t plan more than a year ahead.

His reason why: Circumstances change too quickly. And instead of having a plan, you should always be ready to evaluate opportunities to come your way.

That was eye-opening. Even some of the most successful people I know don’t operate with a long-term plan. They’re just reacting to the environment and the conditions around them.

I learned something similar in the improv class I took a few months ago. The worst thing an improv actor can do is try to plan their next line. If you try to control the scene and come up with a clever idea, it always kills the magic. The great actors stay relaxed, pay attention to what’s happening in the moment, and respond to the offer in front of them.

The Abyss rewards the same kind of behavior. If you walk in with a rigid plan for exactly how your next chapter must unfold, you’ll often miss the opportunities the world is offering you.

Stay in a state of readiness instead of control, and be willing to say yes to the offer before you can see where it leads.

• • •

Step 4: Shed your shell

This isn’t talked about enough.

The hardest part of this journey might not even be figuring out what to do next. It’s letting go of who you used to be.

Most of us are fused to our work identities. A few years ago, I had a cool title at Google, “Global Product Lead”, and letting go of that was harder than I thought. When I left, it didn’t feel like a job change. It felt like a death sentence to the confidence I had tied so closely to my work identity.

My friend Laurie Segall once shared an analogy I’ll never forget.

Context: She was one of the most prominent journalists at CNN, recognized for interviewing Mark Zuckerberg, Tim Cook, and Sam Altman in the early days, before leaving to build her own company under her personal brand.

She told me that lobsters can only grow by shedding their shells. When a lobster outgrows its shell, it has to find a hiding place, cast off the old shell entirely, and sit there soft, exposed, and vulnerable while a new, larger shell forms. It’s the only way the lobster can grow. If it stayed safe in its old shell, it would eventually die inside it.

The Abyss is your soft-shell period. The old identity has to come off before the new one can form, and there’s an unavoidable stretch in between where you feel exposed and formless.

Adam Grant, the author of “Think Again,” says our biggest obstacle to reinvention is that we cling too tightly to identities we’ve already outgrown. He suggests holding your identity loosely, as a hypothesis to be tested rather than a truth to be defended.

Detach your sense of self from your job title, your company, your last win. Those are things you did, not who you are. The more loosely you hold the old shell, the easier it comes off, and the faster the new one can grow.

• • •

Step 5: Reject the B+

Multiple successful entrepreneurs have now told me that the biggest danger of the Abyss is leaving too early.

Mark Pincus says that when you’re desperate to get out, you might land on a B+ idea that feels like an A. You’ll fall in love with building something mediocre because it saves you from the uncertainty. And the risk is that you spend five to ten years working on an average idea.

Henrik Werdelin told me something similar. A few years ago, I asked him what I should do next with my business. I had a few options, but didn’t love any of them. He told me not to move before I was ready. Like chess, grandmasters never make a premature move. They study the position from every angle until they’re ready for the right one.

There’s a poet, John Keats, who called this “negative capability” – the ability to remain in uncertainty without reaching desperately for the nearest answer. He thought it was the defining trait of great artists.

The point is, don’t take the first offer that makes your anxiety go away. Before you commit, ask yourself if you’re pursuing this out of conviction or out of desperation. If it’s desperation, hang on.

• • •

There is no final version of you

Reid Hoffman, the founder of LinkedIn, says that a career is not a fixed destination you arrive at. It’s a startup in permanent beta. You are always iterating, testing, and shipping new versions of yourself. There is no final version, and there was never supposed to be one.

The Abyss, in that light, isn’t an interruption to your real life. It is your real life, in one of its most important phases. Every successful person I admire has been through one - some have been through several, and they’ll go through several more.

Six years ago, I thought being lost meant I had done something wrong. Now I realize it was the most generative period I’ve had. It’s where I found the ideas, the people, and the version of myself I’m still building on today.

So if you’re in it right now, don’t panic, and don’t sprint for the nearest exit. Wander through it and follow your curiosity. Shed the old shell, stay ready, and when the right thing finally shows up, and it will, make sure it’s an A, not a B+.

The Abyss isn’t the thing standing between you and the work. The Abyss is where the work happens.

• • •

📌 Andrew’s Bookmarks

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

• Career advice in the age of AI by Phil Chen – 6 things to do to thrive in your career during the AI era. Written by Phil Chen, a former operator at OpenAI, Google DeepMind, Scale AI, and Stanford.

• Ideas to help you build a better personal network by Ben Lang – Ben is probably top 0.01% in the world when it comes to building a network and community. He was early at Notion, helping build a community of advocates there, and is now at Cursor. Great advice that I recommend everyone read.

• Why Winners Keep Winning (Preferential Attachment) – A shift in perspective: the mindset you should adopt if you want to win over and over again. Written by Eric Jorgenson, the author of one of my favorite books, The Almanac of Naval Ravikant.

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 🍽️ 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 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.

• 🏦 Fidelity Private Shares is 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.

• 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a 3-week validation sprint with Forum Ventures’ AI Studio to pressure-test your thinking, understand the market, and get clarity on whether it’s worth pursuing. And then pitch them for $250k! Apply here.

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

• 💸 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.

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

• • •

💸 Affiliates

Founders, make $$$ by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.

• Rho ($250) – All-in-one banking and financial automation platform for startups.

• Warp ($250) – AI-native payroll, hiring, and compliance in 10 minutes.

• Superpower ($120) – A proactive health platform that tests 100+ biomarkers annually to detect early signs of 1,000+ conditions — giving individuals and teams actionable health intelligence for $17/month.

• Highbeam ($250) – AI financial command center for consumer brands.

• Numeral ($180) – AI for sales tax and compliance across states and countries.

• North.Cloud ($250) – Cut AWS and GCP costs.

• Turing ($200) – AI to match companies with elite, pre-vetted remote software engineers.

• WithCoverage ($300) – A modern risk management for consumer-focused businesses. 1,000+ customers with 99.9% retention.

• Secure Cloud Innovations ($250) – An embedded cybersecurity consulting / consulting team for B2B SaaS companies, helping them design, implement, and maintain security programs for frameworks like SOC 2, ISO 27001, HIPAA, and GDPR so they can close enterprise deals with less internal effort.

• • •

🖼️ Behind the Scenes

Mexico City is WONDERFUL.

I originally planned to visit for a week - I thought it’d be a good destination to ‘lock in’ and focus on creative writing, but frankly the city was distracting in the most positive way and exceeded every expectation I had. I ended up extending my trip and plan to take my parents back in a few months. It’s now one of my favorite cities in the world.

The way I describe it:

• Food: the high-end of Singapore and New York, the low-end and street energy of Southeast Asia.

• Energy: the buzzing, late-night vibe of Barcelona or Shanghai.

• Hospitality and warmth: the effortless grace of Japan, the kindness of Thailand, and the friendliness of Dallas.

• Aesthetic and design: a mix of futuristic Norway, industrial Berlin, and old-world European charm.

• Weather: the endless spring of Los Angeles

Thank you to everyone who shared restaurant recommendations. These were my favorite restaurants out of the dozen I tried.

All to say: I recommend visiting.

Living here this week has been surreal, with the Knicks taking the championship in five games. Their first title in 53 years.

When I told my friends and family I’d be moving to New York in 2020, they said it was a mistake. But to be honest, New York is the only place I’ve ever lived where reality exceeded my expectations. I grew up in China, watching every movie set here, convinced it was the most exciting place on earth. Now that I’ve met the people, built the things, and lived through the sheer randomness of it all, it's somehow exceeded every expectation.

I’m excited to share the events we’re hosting in the coming weeks … A startup comedy show with tech comics you’ve seen on the internet, breakfast with the founder of Zynga, and a rooftop party to kick off the summer.

📅 Upcoming Events

• June 23 | 💼 The Shortlist: June Founder Showcase (NYC) – Meet the founders of the breakout startups in New York who are hiring.

• June 25 | 🚀 Founder Breakfast w/ Mark Pincus, Founder of Zynga (NYC) – I’m inviting two dozen founders for breakfast and an intimate Q&A with Mark.

• June 25 | 🎤 Strong Opinions, Loosely Held: Startup Comedy Show (NYC) – Seven of tech's funniest voices on stage to rant about whatever in tech is driving them insane. A true startup comedy show featuring tech comics.

• June 30 | 🍽️ Extraordinary Founders Dinner (SF) – Hosted at one of the few Michelin-starred steakhouses in the country, known for Japanese A5 Wagyu. EXTREMELY LIMITED SPOTS.

• June 30 | 🌇 June Tech Rooftop Mixer (NYC) – All friends in tech welcome. Join us for sunset views, conversations, and cocktails on the most beautiful rooftop in New York.

• July 28 | 🍽️ Junto Founder Dinner (NYC) – Curated for founders and CEOs only who have raised venture capital or have significant traction.

• November 5–6 | 🗽 Outliers Summit (NYC) – A gathering of ambitious people building extraordinary things. Learn from the uncommon paths behind success. Hosted by Andrew Yeung and Ankur Nagpal. Apply for early access!

• • •

Ask yourself how many people you know who switch between ChatGPT, Claude, and Gemini month to month.

The answer is most of them. Everyone is switching back and forth, constantly, to the model with the best perceived product value. There is zero brand equity.

Would anyone pay more to use ChatGPT if they thought it was just as good as Gemini because they love the brand? Probably not. That means it has no brand equity.

This is a problem nobody in Silicon Valley is talking about.

• • •

Before tech, I spent the first chapter of my career in advertising and brand.

At 15, I worked at what I thought were illustrious brands: Levi’s, Nike, and J. Walter Thompson, one of the world’s largest ad agencies at the time. I was starstruck by Mad Men and wanted a taste of the life.

While I was there, I learned the true meaning of “brand.” And the importance of it. For example, did you know that Fortune 500 companies have a line item on their balance sheet to quantify the value of their brand? Firms like Interbrand publish annual rankings of what those brands are worth. Apple’s brand alone is valued at over $500 billion, separate from the company’s products, cash, or real estate.

One time I was in a meeting with the CEO of J. Walter Thompson Asia, Tom, and someone asked what the definition of “brand” was. I never forgot his answer.

He said: “It is the long-term relationship between a customer and a company.”

Fast forward to today. If there is one thing I’ve observed from spending time around Silicon Valley CEOs and tech founders, it’s that so few talk about investing in brand beyond the initial conceptualization, design, and website build. I think this is a mistake. Here’s why.

• • •

(1) Product excellence is not enough

The AI “startups” of today will be the generational companies of tomorrow. Look at how the modern-day stack of tools is changing from Microsoft Excel, Outlook, and Gmail to ones like Wispr Flow, Gamma, and Perplexity. Everything from how we communicate with colleagues to how we find information on the internet to how we talk with loved ones is evolving.

But product excellence alone won’t cut it. The velocity of product development is extraordinary, yet everyone is building the same thing, leading to a fiercely competitive market flooded with identical, commoditized products. Having the best objective product no longer guarantees market dominance.

(2) People don’t trust AI companies

Simultaneously, trust in AI is at an all-time low. There is a massive disconnect between Silicon Valley and the rest of the world, and most aren’t paying attention.

People do not like AI.

A YouGov survey in late 2025 found that 35% of US adults report using AI at least once a week, but only 5% say they completely trust it.

Ask the regular consumer. Most people do not want agents, digital twins, or OpenClaw poking around in their lives.

(3) We are losing touch with brand marketing

Think back to the David Ogilvy era of enduring brands like Patagonia, Starbucks, and Hershey’s. The brands that make people feel emotion, belonging, and deep trust. Think about the campaigns we still talk about decades later. Volkswagen’s “Think Small” in 1959. Nike’s “Just Do It” in 1988. Dove’s “Real Beauty” in 2004.

You don’t see work like that coming out of tech anymore.

The reason is that companies today are addicted to performance marketing: paid Instagram ads, Google search marketing, paid social. Every dollar attributable down to the click. CFOs love it.

But the issue with overoptimizing for this is that these are transactional touchpoints. People click, download, maybe try the product. Then they forget the brand instantly.

Performance marketing is investing in the next six months. Brand marketing is investing in the next three to five years.

• • •

The cost of overlooking brand

I talk to my friend Lindsay Kaplan about this all the time. She’s the co-founder and former chief brand officer of Chief, the billion-dollar networking company for executive women, and was the first hire and VP of brand at Casper.

I asked her what happens when companies overlook brand. Here’s what she told me:

She continued:

That last line is the one to remember. It is much easier to buy clicks than to build conviction.

• • •

A simple exercise to bring this all together.

Look at today’s top LLMs: ChatGPT, Claude, Gemini. People switch between them constantly, chasing whichever one wins this week’s benchmark.

Brand equity is the premium a customer will pay just for the brand. Right now, every frontier AI product has roughly zero.

Historically, early-stage startups didn’t talk about brand because they didn’t have the money to. But the early-stage AI companies of today are not normal early-stage companies. They are the best-capitalized startups in history. They have generational war chests and the shortest window in tech history to use them.

The companies that win the next decade of AI won’t have the best models. The models will all be roughly the same. They’ll have the best brands.

If I were starting an AI company today, I’d hire a head of brand before my second engineer.

• • •

📌 Andrew’s Bookmarks

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

• Your Most Improbable Life by Kevin Kelly – The less predictable you are, the less likely you are to be replaced by AI. Machines are efficient, and they are powered by the predictable. Strive to be a category of one, and to live the most improbable life you can

• How to make people trust your brand by Tom Orbach – Related to today’s post! For decades, marketing had a cheat code: capital. You could use it to be seen (TV, billboards), to be first (R&D, development), to look good (packaging, branding), and to be good (product quality, talent). But today, AI can do all those things. So what is the new moat?

• Sparkly people and how to find them by Anson Yu – The five people you spend the most time with define you. Here’s how to curate them with sparkly people.

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 🍽️ 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 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.

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

• 🏦 Fidelity Private Shares is 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.

• 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a 3-week validation sprint with Forum Ventures’ AI Studio to pressure-test your thinking, understand the market, and get clarity on whether it’s worth pursuing. And then pitch them for $250k! Apply here.

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

• 💸 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.

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

• • •

💸 Affiliates

Founders, make $$$ by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.

• Warp ($250) – AI-native payroll, hiring, and compliance in 10 minutes.

• Superpower ($150) – A proactive health platform that tests 100+ biomarkers annually to detect early signs of 1,000+ conditions — giving individuals and teams actionable health intelligence for $17/month.

• Highbeam ($350) – AI financial command center for consumer brands.

• Numeral ($250) – AI for sales tax and compliance across states and countries.

• Deel ($250) – Global hiring and payroll across 150+ countries.

• Rillet ($200) – AI‑native ERP that automates core financial operations.

• North.Cloud ($500) – Cut AWS and GCP costs.

• Turing ($200) – AI to match companies with elite, pre-vetted remote software engineers.

• WithCoverage ($300) – A modern risk management for consumer-focused businesses. 1,000+ customers with 99.9% retention.

• Secure Cloud Innovations ($250) – An embedded cybersecurity consulting / consulting team for B2B SaaS companies, helping them design, implement, and maintain security programs for frameworks like SOC 2, ISO 27001, HIPAA, and GDPR so they can close enterprise deals with less internal effort.

• Attention ($200) – An AI-powered revenue intelligence platform that automatically captures, analyzes, and acts on sales call data to help teams coach reps, update CRM, and run agents across their entire pipeline.

• GrowthPair ($200) – Hire top global marketing talent while saving them up to 84% on payroll.

• Oceans Talent ($200) – Oceans connects you with top remote talent to solve business needs.

• Ordinal ($200) – The most powerful end-to-end platform for drafting, planning, and scheduling social media content. Trusted by 1,000+ modern marketing teams.

• • •

🖼️ Behind the Scenes

Last week, we hosted Tech Extravaganza. It was one of my favorite events we’ve ever thrown. Over 1,000 people came out!

We turned an entire floor into a casino. Another floor: a content recording studio, vibe-coding lounge & arcade. And the rooftop into a live music stage.

It took an absurd amount of work to pull off. Huge thank you to our Head of Events, Maks, who made it all happen.

It’s been a few weeks since my last issue, as I’ve been traveling.

First, Lofoten, Norway, for fun, then Toronto, where we debuted The Shortlist with Boardy for Toronto Tech Week.

Norway was wonderful. We went to a beautiful, remote part of the country that felt like we were on another planet. And Toronto Tech Week was incredibly well done. Something that the tech community across North America should consider attending every year.

A great few weeks away from New York, but now we’re back for New York Tech Week. See our upcoming events below.

📅 Upcoming Events

• June 3 | 💻 The Non-Engineer’s AI Playbook, hosted by MuleRun (NYC) – Learn how to deploy AI as a work partner (I’ll be speaking!)

• June 4 | 🎉 Tech Extravaganza (NYC) – Our most exciting event of the year. We're taking over one of NYC's largest venues and transforming it into a massive multi-sensory playground.

• June 10 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• June 17 | 🍽️ Junto Founder Dinner (NYC) – Founders and CEOs only.

• June 23 | 💼 The Shortlist: June Founder Showcase (NYC) – Meet the most exciting, fastest-growing startups in New York who are hiring.

• June 25 | 🚀 Founder Breakfast w/ Mark Pincus, Founder of Zynga (NYC) – I’m inviting two dozen founders to have breakfast and an intimate Q&A with Mark.

• June 30 | 🍽️ Extraordinary Founders Dinner (SF) – Hosted at one of the few Michelin-starred steakhouses in the country, known for Japanese A5 wagyu. EXTREMELY LIMITED SPOTS.

• September 18 | 🗽 The OOO Summit (NYC) – Our most important event of the year for entrepreneurs, builders & creators. Big announcement coming soon. Apply for early access.

• • •

A few years ago, I cold DM’d the CTO of Meta. He was a public figure whose work I had been following for years. To my surprise, he replied instantly and offered to meet with me for 15 minutes.

I was 25 at the time. And had barely interacted with executives at that level, let alone the chief exec at one of the largest public tech companies in the world.

I spent months preparing for those 15 minutes. And when the day came, I was insanely nervous. He was 4 minutes late to the call, so we only had 11 minutes. I had time for three questions, I thought to myself.

I panicked. I asked him three questions, which I now realize were unimaginative and boring. He answered in an equally unimaginative way, half-checked out and multitasking. I could tell I had ruined my opportunity to make a lasting impression. And I did. I emailed him again a year later. No response.

I go back to this example every time I think about the concept of “networking” or building relationships.

There are SO many unspoken norms and expectations around developing professional relationships and building social capital that are never taught in schools or in the workplace. In fact, most people I’ve met are oblivious to these rules. But once I learned them, they helped me succeed in both my corporate life and in entrepreneurship.

Today, I want to share those rules with you.

I learned most of these rules from spending time around busy execs, CEOs, and influential decision-makers. It comes from my uncanny habit of hyperanalyzing social dynamics (perhaps to a fault) over the last few years.

Building Your Network

• Build the well before you’re thirsty. This is first because it’s the most important one. Help people and provide value long before you ask for anything. Asking before you’ve given is the fastest way to deplete social capital and burn a bridge before you’ve even built it.

• There are only three ways to ‘network’. 1. Create something that gets people interested in you. 2. Be great at working the room. 3. Or give first, and generously. Better yet, do all three.

• Surround yourself with energy, not drain. Negative people are contagious, and the chronically unhappy are also unlucky. Choose your inner circle deliberately because the wrong people will pull you down. On the contrary, the right people will make you feel like you can run through walls.

• Identify relationships where lifetime value beats short-term gain. Sometimes this means taking a lower salary to work for someone exceptional. It might mean volunteering for a cause or even doing pro-bono work. Many such examples in tech.

• Create the room yourself instead of trying to get through the door. Host the dinner or throw the event. It’s often easier to be the host than to beg for an invite.

• Master the art of the ask. Be specific, be brief, and make it easy. Vague asks (” Can I pick your brain?”) get ignored. Specific asks (” Can I ask three questions about pricing strategy for my b2b app?”) get answered. And actually make the ask!

• Give more physical gifts. Give someone a gift when they refer you business, introduce you to a decision-maker, or do you a favor. Make it memorable enough that they never forget it.

• Treat junior people like senior people. The intern today is the founder in five years. The assistant is the gatekeeper. How you treat people who can’t do anything for you is the truest indicator of your character.

• Play long-term, positive-sum games. The best way to build social capital is to play long-term games with people who play them too. Short-term extraction will always lose.

Building Your Reputation

• Guard your reputation with your life. Robert Greene calls reputation “the cornerstone of power.” It precedes you into every room, every deal, every relationship. One unflattering story spreads faster than a hundred accomplishments. Protect it ferociously.

• Be a person of your word. The easiest way to build your reputation is to do what you say you’ll do. Ideally, do more than what’s expected. The worst thing you can be is someone who never keeps promises.

• Never burn bridges. I made this mistake many times. Even if you don’t like, respect, or admire someone, there’s no upside to burning the bridge. As the saying goes, “If I only worked with people I liked, I’d be broke.” You don’t have to be everyone’s friend.

• Bite your tongue. The hardest part about being in physical + digital proximity to people you dislike is learning to bite your tongue. Heated arguments and emotional emails have no upside beyond a brief moment of relief.

• Don’t double, triple, or quadruple message someone if they don’t respond. It reeks of desperation. Send once, follow up once, then move on.

• You can build genuine trust online. There’s more of a bond to “internet friends” than you might think. Build it by consistently sending emails, engaging on their posts, sharing their work, advocating for them, and adding value through thoughtful public debate.

• Use AI thoughtfully. AI has become a force multiplier that reveals who the most exceptional operators are, while exposing those who are lazy and tasteless. Don’t overslop your cold emails, important communications, or public writing.

• Always do double opt-in introductions. 99% of good introductions are double opt-in. Don’t fire off an introduction if you haven’t vetted both sides. The best introductions benefit both parties.

• Build your reputation around one memorable quality. Don’t try to be everything. Pick one trait and become known for it.

• Don’t be too eager. Like fundraising, like dating, like most things in life, you want to strike a balance. Things that seem abundant or too available feel lower value. This isn’t about playing games but about understanding your self-worth.

• Create public proof of your competency. Publish a blog with your writing or a portfolio of your work. Create proof of your skills that will serve as your public resume.

• Give first. Give generously, but not always altruistically. Time, energy, and resources without expecting an immediate return build a well of goodwill that lasts a lifetime.

Meeting Important and Influential People

• The easiest way to build a relationship with a busy person is to help them.

• As a young, early-career person, you have two advantages when it comes to meeting important people:

  • First, you have time. Most people think ‘help’ comes in the form of advice, connections, or capital, but you can literally help someone by contributing time and effort.

  • Second, everyone – no matter who you are – has insight into their specific corner of the world. Even if you’re a 19-year-old student, you can come to me and say: “Here’s what I’ve observed about my peers. I saw you write about X and Y, so I thought this might be useful to you.” That is value.

• The easiest way to get a public figure’s attention is to engage with their work online. Responding to social media and blog posts is a life hack. Even the most important people are accessible on a platform like Twitter.

• Play the internet lottery. Send out 10 cold messages or emails a week. Potential customers, partners, mentors. You only need a few to land.

Working With a Mentor

• Counterintuitive advice: recurring monthly mentor meetings often don’t work. You end up filling the time with arbitrary questions.

• Opt for a “board of directors” approach instead. Assemble a handful of people you can go to for specific situations, rather than forcing regular check-ins with one person. Different mentors for different problems.

• Don’t ask for broad, generic advice. “What should I do with my career?” is impossible to answer well. Most people don’t know your exact circumstances or what’s unique to you. Be specific.

• Don’t ask lazy questions. The most thoughtful way to engage a mentor is to think through the problem yourself, land on a few possible solutions, and present them to get their take.

• Put advice to work. Don’t be the person who constantly asks for advice without applying it. Apply it, then share the outcome. This is how you earn more of someone’s time.

• Consider sharing economics with great mentors. If you operate a business or P&L, give your best mentors referral fees or equity. It aligns incentives.

• You may eventually outgrow your mentors, or vice versa. That’s fine.

• • •

📌 Andrew’s Bookmarks

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

• Apocalypse No (The AI jobs narrative is BS) by Scott Galloway – Scott argues the AI job apocalypse is being massively overstated. Every generation thinks machines will wipe out work, but historically, technology creates new industries, new roles, and more productivity. The fear spreads because fear sells … and a lot of people benefit from making AI sound scarier than it is.

• If you can’t get a job today, it’s your fault by Auren Hoffman – Pedigree and school prestige no longer matters in the AI first world. Companies now care more about proof of work than credentials. The people standing out are the ones building things, learning in public, and showing initiative.

• The Six Megatrends That Define 2026 by Derek Thompson – Our increasingly anti-social culture, health miracle drugs, AI apocalypse, and geopolitics.

• Your Job Is Changing Faster Than You Think by Elena Verna – A lot of “good enough” knowledge work is about to disappear. AI won’t replace every role, but it will shrink teams and raise the bar for what makes someone valuable. What does ‘valuable’ mean exactly? Elena explains in this post.

• • •

💃 (Sponsored) The cheapest friendship therapy I've ever done

I built a tool that analyzed five years of texts between me and my best friend.

What it found about us surprised me…

He asked me 2x more questions than I asked him (I had no idea I was the worse friend).

73% of our conversations were started by me.

Our average message is 9.4 words. 1 in 3 contains a joke. Our most-talked-about topic is food.

I call it Perel. It analyzes your iMessages with a friend, partner, or family member and tells you what’s working and how to show up better. Built on the work of Esther Perel, one of the world’s most respected relationship therapists.

This is the kind of insight that takes years of introspection to get.

I built it in a day with Perplexity Computer.

Try it on your own iMessages – click here.

P.S. everything in the pictures is dummy data - but try it for yourself.

P.P.S it might work better with partner vs a friend ;)

• • •

💃 Tech Community Plugs

Resources for entrepreneurs, investors, and tech professionals.

• 🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.

• 🚀 Have a startup idea you’re considering building? Builders Between Ventures is a 3-week validation sprint with Forum Ventures’ AI Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. And then pitch them for $250k! 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.

• 🏢 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.

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

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

• 💸 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.

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

• • •

💸 Affiliates

Founders, make $$$ by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.

• Warp ($250) – AI-native payroll, hiring, and compliance in 10 minutes. Sign up.

• Highbeam ($250) – AI financial command center for consumer brands. Sign up.

• Numeral ($250) – AI for sales tax and compliance across states and countries. Sign up.

• Deel ($250) – Global hiring and payroll across 150+ countries. Sign up.

• Rillet ($200) – AI‑native ERP that automates core financial operations. Sign up.

• North.Cloud ($250) – Cut AWS and GCP costs. Sign up.

• Fondo ($200) – Fondo is the accounting platform for high growth companies. Sign up.

• Oceans Talent ($200) – Oceans connects you with top remote talent to solve business needs. Sign up.

• • •

🖼️ Behind the Scenes

Last week I was in Lofoten, Norway. I’ve never been anywhere like this before. It’s the most bizarre place I’ve ever been.

For one, during the summer, the sun does not set. 24 hours of daylight every day. The locals call it the Midnight Sun.

At 12:00 am, people are still hiking, kids were playing outside.

Five days of consistent daylight put me in an euphoric, trance-like dream state. Highly recommend experiencing this at least once in your life.

I spent the last few weeks catching up with friends, and it seems like everyone is feeling some sense of FOMO with AI.

Six entrepreneurs I talked to are planning to sell (or are in the process of selling) their companies. The executives I know are moving to frontier labs. Creators are pivoting their entire strategy to be more AI-oriented. This is the first time in my 10-year career I’ve seen so much change, turmoil, and uncertainty.

Over the next few months, I’ll be hosting more educational events (like the one with Ankur on May 5) on how to optimize your career for the AI era, since that seems to be the question that everyone is trying to answer for themselves.

And if you’re looking to work at a fast-growing tech company, I started a side project to match people with the top startups in my network. Sign up here for my talent network.

📅 Upcoming Events

• May 5 | 🎤 The Founder’s Endgame: Fireside Chat w/ Ankur Nagpal (NYC) – ​Lessons from $300M+ in exits and what he thinks founders should be doing today with Ankur.

• May 12 | 🍽️ Junto Founder Dinner (NYC)

• May 15 | ☕ Founder Breakfast Club (NYC)

• May 29 | 💼 The Shortlist: Canada Founder Showcase (Toronto) – Meet the fastest-growing startups in Canada who are hiring during Toronto Tech Week.

• June 4 | 🎉 Tech Extravaganza (NYC) – Our largest event of New York Tech Week – come meet other friends in tech!

• September 18 | 🗽 The OOO Summit (NYC) – Our most important event of the year for entrepreneurs, builders & creators. Big announcement coming soon. Apply for early access.

• • •

Around this time last year, I published my AI Productivity Stack, a guide to all the AI tools I use as an entrepreneur, creator, and knowledge worker. It was by far my most popular article of the year.

Since then, I’ve continued to experiment, and less than a year later, my way of working has almost completely changed. Today, I’m sharing the updated guide. I’d estimate that these tools save me 50% of my time compared to three years ago.

Also, to get one level deeper, I recently hosted a podcast with my friend Laurie Segall, who happens to be a former journalist and entrepreneur known for interviewing Mark Zuckerberg, Tim Cook, and Sam Altman (here’s her episode with Sam), where I showed her how to vibe code in real time while talking to my computer. We cover other tools too

Check it out here and let me know what you think.

General Communication

• Writing anything: I’ve switched from ChatGPT to Claude for all my writing. I have Claude skills (custom instructions that teach Claude how to write in specific ways) for LinkedIn posts, newsletter articles, event invitations, and more. It sounds more natural, and I’ve trained Claude to write a dozen different ways. Sometimes I want to sound like myself. Other times, I may want to be more formal or more empathetic.

• Staying on top of my emails: I use Boomerang religiously to bump up emails if others don’t respond. This helps me stay on top of my inbox.

• Wispr Flow: I installed a microphone at my desk because I speak to my computer more than I type now. It’s roughly 2-3x faster on a words-per-minute basis. The same is true for texting and sending messages on my phone. Check out Wispr Flow.

• • •

Social Media

• Creating TikTok videos: I use Claude Code, Claude Skills, and a Notion MCP to crack TikTok virality. I’ve turned it into an automated, formulaic process that can turn any idea into a video with 100,000+ views. I’ve tested this extensively. The result: 50,000 followers in 30 days. Claude Code handles research, ranking, and script generation. Notion MCP handles project management.

• Managing my LinkedIn inbox: Kondo helps me stay on top of my inbox and lets me tag and sort contacts into categories. It’s the only tool that does this well.

A note on MCPs: Throughout this article, you’ll see me refer to MCPs. MCP stands for Model Context Protocol. It’s a shared language that allows LLMs to interact with other apps. In the scenario above, I can build and maintain Notion project trackers directly through Claude Code.

• • •

Network and Relationship Management

• Managing my contacts: We have over 50,000 pieces of contact information from event attendees. We’ve spent the last few months migrating to Attio. It’s simple, versatile, and has an MCP, which is a game-changer.

• Finding the right people in my network: I’ve imported all my LinkedIn and Twitter contacts into Claude Code to build a makeshift CRM. It helps answer questions like: “I’m traveling to San Francisco. Who are all the consumer CEOs in my network I should meet?” Happenstance can do this too.

• Taking meeting notes and sending follow-up emails: Granola is a godsend for this. You can turn your meeting notes into follow-up emails, blog posts, long-form essays, etc.

• • •

General-Purpose Productivity

• Researching information: Claude Code is great for this because it can connect to Notion or Google Sheets through an MCP. For example, if I need to find a restaurant, I can prompt Claude Code to build a project tracker in Google Sheets with suggestions ranked by price, location, and vibe, then send emails to all the restaurants to make reservations through the Gmail MCP.

• My personal assistant: Poke is my AI assistant that has access to all my emails and calendars. It can remind me of things, help me schedule, send emails, and, most importantly, search my inbox for important information. The best example: if I have an email from years ago that I forgot about, Poke can instantly find it and pull it up.

• Generally, doing things faster on my computer: I use Raycast to access my clipboard history, emojis, download history, recent screenshots, and notes with keyboard shortcuts. It’s improved the speed of using my laptop by more than 10%.

• Keeping up with the world: I don’t read much news, but Particle gives me a daily digest of key headlines summarized and aggregated from diverse news sources. I also built my own tool with Claude Code that scrapes 100+ sources online every day, ranks them by importance and relevance based on what it knows about me, and sends me a morning email briefing.

• • •

Building and Designing Things

This is by far the category I’m most excited about.

Everything above helps you work a little faster and more efficiently. But this is an entirely new category that lets you do things you couldn't do before. In just 12 months, anyone can become an exceptional designer and product builder.

• Building software: I started with Lovable and highly recommend it for anyone just getting started. You can build anything: websites, productivity apps, habit trackers, fitness apps. Just describe what you want, and it builds it for you in real time. As you get more advanced, you can experiment with Claude Code. I use Warp as my ADE (Agent Development Environment) – a piece of software that lets me interact with code.

• Making decks, infographics, posters, and product mockups: Gamma, NotebookLLM, and Luma AI are great for designing any of these.

• Generating pictures or videos: Flora, Gemini, and Ideogram are incredibly intuitive to use, and you can create anything from an iPhone wallpaper to a music video for your dog … simultaneously!

• Creating AI avatars: Use LemonSlice or HeyGen to make AI avatars for talking-head videos on TikTok. In the long run, I think there’s a world where companies create viral scripts along with AI avatars to promote their products. Many are already doing this.

Things I’m Experimenting With

• Zo Computer: I recently invested in this company. To me, it’s an introduction to AI with a clean interface for beginners. If you want to get started with Claude Code but feel too intimidated, try Zo Computer instead. It does everything Claude Code can do. Disclaimer: I’m an investor.

• Audos: Use AI to build your solopreneur business. It helps you identify your profile, suggests business ideas, helps you build it, suggests customer acquisition strategies, and even helps you get funding. Try Audos. Disclaimer: I’m an advisor.

• Suno: Not sure how I feel about this one, but you can generate your own music based on genres and styles you love. AI-generated artists are already trending on the top Spotify charts, which is insane to me. Try Suno.

• ElevenLabs: Clone your voice or build customer service agents that speak just as eloquently as humans. Btw, use ANDREWYEUNG for 11% additional credits to get started. Try ElevenLabs.

• Micro: The last CRM you’ll ever need. Plugs into all your communication channels and helps you track all your contacts. Try Micro. Disclaimer: I also invested in this company.

• RPLY: An inbox to amalgamate all your communication channels. Haven’t used this one yet, but I’ve seen it on Twitter and want to try it out. Try RPLY.

Are AI Tools a Waste of Time?

I came across a stat recently that said that 99.7% of the world has not yet paid for an AI service. As someone who uses these tools every single day, I find that mind-boggling.

Yet, I understand, because non-techies around me often ask me if all this is a sham. Many see the headlines from Silicon Valley and assume this is all a Ponzi scheme to get us to invest more in these AI companies.

So to those who are skeptical, I invite you to do this: Do not form a perspective until you’ve tried a few of these tools. And I don’t mean prompting ChatGPT or asking Claude a question, but taking the time to experiment with one of the tools I suggested above. Then you will see the value and can form an assessment yourself.

I’m vibe coding daily. My team is vibe coding daily. My friends are vibe coding daily. Even my girlfriend is vibe coding daily. But again, we might just be AI-pilled.

• • •

💸 Affiliates

Founders – make $2,000 in one day by booking calls!

Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.

Block off one day, take a dozen calls, and walk away with $2,500. I call it Uber Black money. All you have to do is take the call.

Here are the offers:

• Rho ($250) – All-in-one banking and financial automation for startups. Sign up.

• Warp ($250) – AI-native payroll, hiring, and compliance in 10 minutes. Sign up.

• Deel ($250) – Global hiring and payroll across 150+ countries. Sign up.

• Crstl ($250) – AI-powered B2B commerce and EDI automation. Sign up.

• Highbeam ($250) – AI financial command center for consumer brands. Sign up.

• Pilot ($250) – Bookkeeping, taxes, and CFO services for startups. Sign up.

• North.Cloud ($250) – FinOps platform to cut AWS and GCP costs. Sign up.

• Stanify ($200) – AI-powered community management for comments and DMs. Sign up.

• WithCoverage ($250) – Modern risk management with 50+ carriers competing for your business. Sign up.

• Pinpoint ($200) – Automates personalized DMs to convert social engagement into revenue. Sign up.

• • •

💃 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.

• 🎙️ SpeakON – Voice-to-text, but make it hardware. Unlike software-only tools,

  SpeakON pairs an AI keyboard with a magnetic mic that snaps right onto your

  iPhone. Better audio, offline recording, and text that comes out polished —

  not just transcribed. Press, speak, done. 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 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.

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

• 🤖 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.

• 🇺🇸 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

The loneliest people in America aren't the elderly, but young adults (18–25 year olds).

Three stats that shocked me:

• Today, 15% of men reported having ZERO close friends.

• 50% of U.S. adults report experiencing loneliness regularly.

• And Americans spend 20% less time socializing in person vs 20 years ago.

This is *extremely* important, because social connection is the #1 predictor of long-term happiness.

Andy Dunn is solving this with Pie. (Pie stands for People I Enjoy, btw)

I read Andy's book, Burn Rate, a few years ago and was inspired by his story of building Bonobos – the 1st company of its kind- and later revealed that he did it while dealing with bipolar disorder.

He's a massive advocate for mental well-being and has decided to tackle the single biggest problem of our generation: social isolation.

It's been awesome to get to know Andy and be part of his journey as an investor advisor. Last week, we welcomed Andy to NYC and hosted a series of breakfasts and talks for community builders and builders. Thank you to everyone who came out to support!

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

• Apr 17 | ☕ Founder Breakfast Club (NYC) – For Seed & Series A CEOs.

• Apr 21 | 🚀 Builder’s Breakfast with Andy Dunn & Andy Yeung (NYC) – We are hosting a special breakfast for founders, creators & community builders - the 'builders' of the next generation. Only 20 spots.

• Apr 21 | 🎤 Fireside Chat: ‘hot takes on building sh*t’ with Andy Dunn, Founder of Bonobos (NYC) – An intimate, unfiltered conversation with my friend Andy Dunn on entrepreneurship and careers.

• Apr 22 | 🍽️ Junto Founder Dinner (NYC) – For Series A+ CEOs only.

• Apr 23 | 💐 spring tech mixer (NYC) – Come meet founders, operators & friends in tech!

• Apr 27 | 💼 The Shortlist: April Founder Showcase (NYC) – Meet the most exciting, fastest-growing startups in New York who are hiring.

• Apr 29 | 🍽️ Head of Growth Salon Dinner (NYC) – A curated salon dinner for the TOP head of growth operators at Series A to D startups, moderated by yours truly. Every attendee is required to give a 3-minute demo of an agentic workflow that helps them in their role.

• Apr 30 | 💻 The 2026 Guide to Breakout Content (Virtual) – My modern playbook behind building a personal brand with 50M+ views and 250K+ followers. Free to attend.

• May 12 | 🍽️ Junto Founder Dinner (NYC) – For Seed & Series A+ CEOs only.

• May 15 | ☕ Founder Breakfast Club (NYC) – For Seed & Series A CEOs.

• May 29 | 💼 The Shortlist: May Founder Showcase (Toronto) – Psst we’re coming to Toronto!

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.

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 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.

• 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.

• • •

💃 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.

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

• Mar 31 | 🍽️ Junto Founder Dinner (NYC)

• April 6–9 | 🌉 HumanX (SF) – Join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!

• April 7 | 🍽️ Junto Founder Dinner (San Francisco) – Hosted with my friend, Nikunj Kothari, Partner at FPV Ventures, at a Michelin-star Thai restaurant.

• April 8 | 🍽️ Junto Founder Dinner (San Francisco) – Hosted at my favorite steakhouse in SF for Seed–Series B founders!

• Apr 17 | ☕ Founder Breakfast Club (NYC)

• Apr 21 | 💐 spring tech mixer (NYC) – Come meet founders, operators & friends in tech!

• Apr 22 | 🍽️ Junto Founder Dinner (NYC)

• • •

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.

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.

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.

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.

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.

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.

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.

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.

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.

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

• Mar 14 | 🤫 secret austin garden party (Austin) – Our iconic secret party that we throw every year. Thousands of people come from all over the world. You can also apply to volunteer here.

• Mar 15 | 🏡 ceo dinner (series a+) at a private mansion “off menu” (Austin)

• Mar 23 | 🎙️The Shortlist: March Founder Showcase (NYC) – An invite-only evening connecting six CEOs with exceptional engineers, designers, and business leaders looking to work at a breakout tech company.

• Mar 24 | 🍽️ Junto Founder Dinner (NYC)

• Mar 26 | ☕ Founder Breakfast Club (NYC)

• Mar 31 | 🍽️ Junto Founder Dinner (NYC)

• April 6–9 | 🌉 HumanX (SF) – Join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!

• April 7 | 🍽️ Junto Founder Dinner (SF) – We’re coming to SF for two nights! Please apply if you are a founder/CEO.

• April 8 | 🍽️ Junto Founder Dinner (SF)

• Apr 17 | ☕ Founder Breakfast Club (NYC)

• Apr 21 | 💐 spring tech mixer (NYC) – Come meet founders, operators & friends in tech!

• Apr 22 | 🍽️ Junto Founder Dinner (NYC)

📌 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.

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.

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.

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.

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.

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.

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.

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.”

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.

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.

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?”

• • •

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.

• • •

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.

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

• Mar 23 | 🎙️The Shortlist: March Founder Showcase (NYC) – an invite-only evening connecting six CEOs with exceptional engineers, designers, and business leaders looking to work at a breakout tech company.

• Mar 24 | 🍽️ Junto Founder Dinner (NYC)

• Mar 26 | ☕ Founder Breakfast Club (NYC)

• Mar 31 | 🍽️ Junto Founder Dinner (NYC)

• April 6–9 | 🌉 HumanX (SF) – join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!

• Apr 17 | ☕ Founder Breakfast Club (NYC)

• Apr 22 | 🍽️ Junto Founder Dinner (NYC)

🤠 South by Southwest (Austin)

• Mar 12 | 🥂 ceo dinner at a private mansion “off menu” (Austin) – hosted at a private mansion 5 minutes away from downtown Austin.We only have 12 spots!

• Mar 13 | 🥂 ceo dinner at a private mansion “off menu” (Austin)

• Mar 14 | 🤫 secret austin garden party (Austin) – our iconic secret party that we throw every year. Thousands of people come from all over the world!

• Mar 15 | 🥂 series A+ ceo dinner at a private mansion “off menu” (Austin)

🤝 Get Involved (Austin)

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

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

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.

The Shortcut to Ending Self-Doubt

50% of entrepreneurs struggle with anxiety.

But most of us treat negative self-talk like a fitness goal: grind harder, push longer, will it away. That’s how it stays.

This guide flips that. In 10-15 minutes, you can unlearn the root of the chatter and permanently feel free. No more pep talks, no more affirmations that feel hollow.

You’ll learn:

• Why most growth advice doesn’t work

• The little-known, simple method to permanently “deleting” limiting beliefs

• How to liberate yourself from patterns like anxiety and procrastination

• The inner foundation for outcomes like increased revenue and shorter launch cycles

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.

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

• Feb 23 | 🎙️The Shortlist: Feb Founder Showcase (NYC) – an application-only evening connecting six breakout CEOs with exceptional engineers, designers, and business leaders.

• Feb 26 | ☕ Founder Breakfast Club (NYC)

• Mar 24 | 🍽️ Junto Founder Dinner (NYC)

• Mar 26 | ☕ Founder Breakfast Club (NYC)

• April 6–9 | 🌉 HumanX (SF) – join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!

🤠 South by Southwest in Austin

• Mar 12 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin) – hosted at a private mansion 5 minutes away from downtown Austin. If you run a seed to series B company, you’re invited. We only have 12 spots!

• Mar 13 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)

• Mar 14 | 🤫 secret austin garden party (Austin) – our iconic secret party that we throw every year. Thousands of people come from all over the world!

• Mar 15 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)

• Get involved (Austin):

  • 🤝 I’m looking for FOUR young, ambitious people to shadow me – 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 – join the A-team and help with our secret garden party on March 14.

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

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.

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

• Feb 17 | 🍽️ Junto Founder Dinner (NYC)

• Feb 23 | 🎙️The Shortlist: Feb Founder Showcase (NYC) – an application-only evening connecting six breakout CEOs with exceptional engineers, designers, and business leaders.

• Feb 26 | ☕ Founder Breakfast Club (NYC)

• Mar 12 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin) – hosted at a private mansion 5 minutes away from downtown Austin. If you run a seed to series B company, you’re invited. We only have 12 spots!

• Mar 13 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)

• Mar 14 | 🤫 secret austin garden party (Austin) – our iconic secret party that we throw every year. Thousands of people come from all over the world.

• Mar 15 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)

• Mar 24 | 🍽️ Junto Founder Dinner (NYC)

• April 6–9 | 🌉 HumanX (SF) – join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!

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

• Mar 12, 13, 15 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)

• Mar 14 | 🤫 secret austin garden party (Austin)

Resources

• 📌 Unofficial Events List for SXSW 2026 — a curated list of events and parties happening around South by Southwest, updated daily (bookmark this)

• 📝 Submit your event to our events list: Submission form.

• 💬 Connect with others going to SXSW: Join our group chats.

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.

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

📅 Upcoming Events

• Jan 21 | 🍽️ Brandmakers Dinner Club (NYC) – a 20-person salon dinner for CMOs and heads of marketing at consumer companies.

• Jan 27 | 🚀 The Shortlist Founder Showcase (NYC) – an application-only evening connecting six breakout founders with exceptional engineers and GTM operators.

• Jan 28 | 🍽️ Junto Founder Dinner (NYC) – for seed to series B founders/CEOs.

• Jan 30 | ☕ Founder Breakfast Club (NYC)

• Feb 10 | 🇺🇸 Extraordinary Founders Dinner (NYC) – for ambitious immigrant founders and builders - hosted at our favorite Chinese restaurant.

• Feb 17 | 🍽️ Junto Founder Dinner (NYC)

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.

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

• Jan 21, 2026 | 🍽️ Brandmakers Dinner Club (NYC) – an exclusive 20-person salon dinner for CMOs and heads of marketing.

• Jan 28, 2026 | 🍽️ Junto Founder Dinner (NYC)

• Jan 30, 2026 | ☕ Founder Breakfast Club (NYC)

• Feb 10, 2026 | 🇺🇸 Extraordinary Founders Dinner (NYC) – bringing together ambitious immigrant founders and builders at our favorite Chinese restaurant.

• Feb 17, 2026 | 🍽️ Junto Founder Dinner (NYC)

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.

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.

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.

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

• Jan 21, 2026 | 🍽️ Brandmakers Dinner Club (NYC)

• Jan 28, 2026 | 🍽️ Junto Founder Dinner (NYC)

• Jan 30, 2026 | ☕ Founder Breakfast Club (NYC)

• Sep 18, 2026 | 🗽 The OOO Summit (NYC)

👋 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

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.

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.

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.

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.

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.

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

• Dec 9 | 🤖 Robotics & Physical AI Summit & Awards Ceremony w/ Nebius (SF) [Not my event]

• Dec 10 | 🍽️ Junto Founder Dinner (NYC) – for seed-series B founders & CEOs only.

• Dec 12 | ☕️ Founder Breakfast (NYC)

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).

• Marketing & Events Intern, Fibe – reply here

• GTM Generalist, Antimetal

• Content Manager, Perplexity

• Chapter Lead, Hampton

• Founding Engineer, Icon

• Investor, Eniac Ventures

• Chief of Staff, Knoetic

• Growth Manager - IRL, Basic Capital

• Head of Engineering, Superpower

• Growth Marketing Manager, Baselayer

• Product Manager, Cloaked

• Data Scientist / Engineer / Founding Designer, Windmill – Working with the former co-founder of Yext

• Events Associate / Marketing & Events Roles, Manifest Law

• Marketing Manager, Vylit – Working directly with the former CEO of OnlyFans.

• Head of Growth, Taxwire

• Account Executive, V7

• Head of GTM, Elloe

• Content Creator & Social Media Marketing Lead, Escargot

• Lead Product Designer, EZ Newswire

• Business Development Associate, ModernFi

• Head of Product, Limitless AI

• Have a job to share? Let me know by replying to this email.

• 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.

• 🚀 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.

📅 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!

• Dec 2 | 🍽️ Junto Founder Dinner (NYC) – for founders/CEOs of Seed–Series B companies.

• Dec 10 | 🍽️ Junto Founder Dinner (NYC)

• Dec 12 | ☕️ Founder Breakfast (NYC)

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.