👋 Friends,
Today’s article is important - one I’ve been thinking about for the past year after being on the road and meeting all types of people from all over the world.
Sep 30 | 🎤 From SWE to CTO: Building an engineering career in the age of AI (NYC) – A fireside chat with engineering leaders from Datadog, Thread AI and Deepgram, discussing how they built their careers.
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 us.
Oct 2 | 🐶 tech pawty (NYC) – We're teaming up with Puppy Sphere to host a tech pawty - a morning with puppies, coffee & many other founders.
Oct 14 | 🍽️ Junto Founder Dinner (SF) – We’re back in SF! Join vetted founders and CEOs only for supper in our private dining room.
Oct 15 | 🍽️ Extraordinary Founders Dinner (SF) – Join me and a dozen vetted Series A+ founders for dinner at a Michelin-starred restaurant.
Nov 5–6 | 🗽 The Outliers Summit (NYC) – A two-day gathering in New York for founders, builders, and creators bringing unreasonably ambitious ideas to life. Ticket prices go up tomorrow.
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I have something to admit. I’ve spent the last few years bringing thousands of people together, building communities, and helping people make connections.
But somewhere along the way, I think I’ve become less kind.
I used to make time for almost anyone who asked for help. Now I sometimes catch myself wondering how someone can help me before deciding to respond.
I don’t particularly like that version of myself.
It’s an uncomfortable thing to admit, especially when so much of my work revolves around helping other people.
New York has a way of doing that to you. You’re surrounded by ambitious people relentlessly pursuing their next milestone. Your calendar fills up, your attention becomes scarce, and eventually, you start viewing every interaction through the lens of opportunity.
You become more efficient with your time, but perhaps less generous with it.
I’ve been thinking about this a lot lately, especially after revisiting Paul Graham’s essay, Mean People Fail. He makes a compelling argument that kindness isn’t simply a moral virtue. It’s also a competitive business advantage. Mean people waste energy fighting, struggle to build strong networks, and may be motivated by the wrong things. Kind people, meanwhile, have more opportunities to build relationships and work with others.
So I’ve been trying to become more intentional about kindness. Here are a few practices I’ve adopted to become kinder.
1. First, kindness is self-fulfilling. If you believe you are a kind person, then you will do kind things. But the inverse works too. Do kind things and you will start to believe you are a kind person.
2. Remember that every person you meet is going through something you know nothing about. The people who are angry or short with you are often quietly going through their own personal hell.
3. Never attribute to malice what can be explained by carelessness. When someone hurts you, assume a mistake before bad intent. This is Hanlon’s Razor, and the easiest way to practice it is simple: always assume positive intent.
4. Create distance between stimulus and response. Take a breath before the reflexive reply. Sleep on the angry email. A minute of calm can be all it takes to completely change your attitude.
5. Choose kind over right. When you have to pick between being kind and being right, pick kind. Most arguments aren’t worth winning. You can be correct and still lose the relationship, and being right rarely feels as good as you think it will once the other person walks away feeling small.
6. Speak well of people when they’re absent. My friend Jess taught me this. Speaking well of someone behind their back, instead of the opposite, builds a reputation that reaches them eventually. And just noting what you admire about someone, even when they’ll never hear it, changes how you show up around them.
7. Find a small way to regularly gift. It can be leaving a generous tip for your barista every morning. Or dedicating an hour of your time each week to students. The key is that the gift should be small but significant enough to cost you somethingThe easiest way to start is with a small, daily habit. Try to make someone’s day, every day.
8. Write it down: Be Kind. I have a shirt I occasionally wear that says “Be Kind” across it in bold white font. I also printed a hundred others and distributed them to friends and people in the community. I find that it keeps me accountable. People strive to be consistent with the things they share publicly.
9. Help someone win over the long term. Not an employee, a direct report, or a family member. That way you know you’re doing it for the right reasons, not because you expect something in return.
An element of true generosity is that it requires a tradeoff - something that costs you time, money, or resources. It’s easy to be kind to a celebrity, but can you be kind to the new grad who has nothing to offer you?
Kindness is important for many reasons. It creates a positive ripple effect in communities, a rising tide that lifts all the boats. It inspires people in those communities to be happier, healthier, more productive, and more connected, and they go on to do the same for others.
I don’t think kindness and ambition have to be opposing forces, but I’ve learned that when you’re constantly chasing the next opportunity, generosity takes conscious effort. It’s something I’m still working on.
But the surprise, for me, was more personal than that. Kindness didn’t just help the people around me. It made me like myself more.
• • •
📌 Andrew’s Bookmarks
My favorite links to help you be wiser and more creative.
The Microwave Economy by David Perell – We've become obsessed with making everything faster, cheaper, more convenient, often sacrificing beauty along the way. David explains why so many of our homes, products, and experiences feel increasingly generic, and makes the case for being more intentional about what we consume.
Failures of Kindness by George Saunders – When George Saunders (writer) looks back on his life, his biggest regrets are the moments when he could have been kinder but wasn’t. In this commencement speech, he reminds us that we spend so much of our lives chasing success that we often overlook what matters most.
Extreme brainstorming questions to trigger new, better ideas – Sometimes the best way to come up with new ideas is to ask ridiculous questions. Jason shares 15 extreme thought experiments that force people to challenge their assumptions.
Willingness to look stupid is a genuine moat in creative work by Sharif Shameem – As we become more successful, we often become afraid of sharing bad ideas, which ironically makes us less creative. The trick is to experiment more, publish imperfect work, and worry less about what others think.
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🚀 Outliers Summit ticket prices go up tomorrow (Sep 30)
The Outliers Summit is almost here. If you haven’t registered yet, you should know ticket prices go up next Wednesday, September 30. After that, every tier goes up by ~10%.
In real terms, two-day passes go from $199 to $219. If you’ve been meaning to grab your spot, this is the week.
And some news I’m excited about.
Every ticket holder now gets access to $100,000+ in credits to the best tools for creating, building, and shipping, straight from our partners.
That includes companies like Vercel, ElevenLabs, Granola, Datadog, Fin, Stan, Fyxer, Thoropass, Zo Computer, Agree.com, Flora, Digital Executive, Zypsy, and Airtaskr, with more to be announced. Day one of the summit is about leaving with something you built, and now you’ll have the tools to keep building it after you go home.
The lineup of speakers so far:
Sam Parr (sold The Hustle to HubSpot for $20M+)
Zach Sims (sold Codeacademy for $500M+)
Carina Hong (raised $200M+ for Axiom Math)
Andy Dunn (sold Bonobos to Walmart for $310M)
Ryan Hoover (sold Product Hunt to AngelList)
Sahil Lavingia (Gumroad, $1B+ paid to creators)
Nadya Okamoto (cofounder of August, Pie)
Nat Eliason (Founder School)
Nik Sharma (Sharma Brands)
Ankur Nagpal (sold Teachable for $250M and Carry to AngelList)
and more to come...
• • •
💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
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💡 Have a startup idea you're seriously considering building? The Foundry is a 5-week sprint with Forum's AI Venture Studio to stress-test it, confirm market demand, and get a straight answer on whether it's worth pursuing. Strong candidates pitch for $250K. Kicks off November 10th. Apply here.
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What other perks should I include? Let me know.
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🖥️ The best marketers I know are becoming engineers
Profound is building the tools for the “Marketing Engineer,” and the shift is real
Most marketers can’t answer a basic question: what does ChatGPT say about your company when someone asks?
Profound is built for exactly that. It’s an AI marketing platform that tracks how AI search talks about your brand in real time, then hands you agents to act on it. Their FactCheck feature is the part that caught my attention. One of the biggest fitness wearable brands ran it and found AI was misrepresenting them 11% of the time.
Their new AI Marketer, Aim, turns those signals into a ranked list of opportunities every week, then sub-agents draft the work while your team reviews and ships.
It turns your brand context and AI search data into marketing tasks, coordinates specialized AI agents to execute them, and measures whether the work improves your brand’s visibility.
The AI handles the grunt work. You keep the taste. That’s the Marketing Engineer in practice.
Also, congrats to Profound for raising a $180 million Series D at a $1.8 billion valuation!
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🖼️ Behind the Scenes
After hearing about Madiera, Portugal from multiple friends, I knew I needed to visit. Last week, I took my parents here and we went off-roading in a Land Rover, hiking among the laurel forests and stopping in villages we’d never have found on our own.
It might be one of the only places in the world where you can live in a subtropical European city, hike above the clouds, and swim in the ocean, all within an hour of home.
The temperature is 65–75 °F year-round (perfect), which means you can be in a tee shirt and shorts whether it’s summer or winter.
I also learned that this is where Cristiano Ronaldo grew up. Here, he's closer to a god than a celebrity. The airport is named after him. There's a museum of his trophies and a hotel with his initials on it. Every shop sells his jersey.
Apparently they call this island the “Hawaii of Europe”
P.S. Highly recommend Black Tomato for booking private, curated travel tours in unique destinations.
“You become more efficient with your time, but perhaps less generous with it.“
I think that’s what stands out to me the most.
My friend Leon made this book "Go Be Kind: 28 1/2 Adventures Guaranteed to Make You Happier" and I gave one of the pages to a stranger on an airplane. She happy cried because she thought it was so kind.
https://a.co/d/0hAoqJZs