👋 Friends,
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:
Not everyone wants feedback, no matter how much it may help them.
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
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• • •
🗽 (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:
• • •
🖼️ 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!
"Only a Sith deals in absolutes." One of my fav lines! Happy birthday 😊
giving value without expecting to receive anything in return is the only way
also, giving unsolicited advice is a hard no and something i’m always working on