👋 Friends,
Every time I visit San Francisco, I’m shocked by what I learn. The AI, the quirkiness, the culture, the ambition. These are my observations from my last trip there.
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• • •
I spent the last week in San Francisco hosting events and meeting founders, CEOs, and people at the cutting edge of AI.
SF still feels 6 to 12 months ahead of New York in tech culture and AI, and my mind gets blown every time I visit.
Some observations I thought were worth sharing:
1. Founders are building personal brands as career insurance. I met founders raising venture capital while also investing heavily in Instagram, TikTok, and LinkedIn. If the company fails, they still own the audience. They can launch something else, promote another product, or become a full-time creator.
2. AI companies have more money than attention. If you walk around downtown San Francisco, you will see sponsored billboards, buses, cafes, dinners, and ads for ridiculous parties. The AI labs have more money than ever, but attention is more scarce than ever. Everyone wants a piece of it!
3. Tiny teams are the new flex. Gamma crossed $100M in ARR with roughly 50 employees a few years ago. That’s about $2M in ARR per employee. Five years ago, headcount was a status symbol. Today, revenue efficiency is.
4. B2A is the new B2B. Business-to-agent. Marketers are starting to create content and products designed to be discovered, understood, and recommended by AI agents. Have you ever read a blog post written for an agent instead of a person? It feels a little dystopian.
5. The people closest to AI are often the most paranoid about it. I was surprised by how many founders had a doomer mindset. They’re pessimistic about where AI could lead, while still being wildly optimistic about building their company.
6. Company aura is becoming a recruiting strategy. One founder told me their most important priority right now is attracting talent. The problem is that the big AI labs can often pay more, so startups have to compete on brand, mission, culture, and the feeling that you’re joining something important. I think Profound does this incredibly well. They have a strong social presence, great events, a recognizable culture, and a company people seem to want to be associated with. In a market where compensation is hard to compete on, aura becomes part of the offer.
7. A lot of talented people are stuck in the abyss. They’ve made enough money to be selective, but not enough to stop working. They don’t want another normal job, but they also don’t know what they want to build next. AI has made the number of possible paths feel almost infinite. Analysis paralysis.
8. AI could create one of the biggest new wealth classes Silicon Valley has ever seen. I did some rough math on OpenAI and Anthropic and came to a pretty wild conclusion: over the next few years, these companies alone could mint 10,000+ new millionaires. And people are already talking about the second-order effects. What happens to housing, angel investing, restaurants, private clubs, and everything else in SF when thousands of people suddenly have significantly more money? The wealth effect of AI hasn’t even really started yet.
9. Proprietary company data is becoming an asset class. I kept hearing about companies realizing that years of internal Slack conversations, support tickets, workflows, and other proprietary data are suddenly valuable to AI companies and data labelers. I heard of deals starting around $500K. For years, a lot of this information was basically useless. Now people are asking: what could someone train a model on that only we have?
10. Hacker houses are everywhere. I visited one where founders gave themselves six months to hit product-market fit. They eat, sleep, and work in the same house, with no distractions. In a world where everyone is racing toward AGI, time compression is everything.
11. SF makes it unusually easy to lock in. Good food is everywhere. There’s space to think. People don’t stay out that late. The weather is good. It’s very easy to fall into a routine of building, walking, eating, then going back to building. I fell into this trap.
12. The gap between SF and the rest of the world feels wider. The people I meet here are more AI-pilled than ever. Meanwhile, I still meet smart people outside major tech hubs who haven’t heard of some of the fastest-growing AI companies.
13. Working at Google is no longer the ultimate flex here. In most places, telling someone you work at Google sounds impressive. In SF, someone might respond: why aren’t you building something?
14. There’s an AI gold rush, and everyone has realized it. I met founders from London, Berlin, and Croatia who flew in to raise money, meet customers, and find talent. Nobody sent them. They just heard there was gold in the hills.
15. AI influencers are printing money. I heard about creators with ~100,000 followers making seven figures a year. AI companies have more cash than distribution, so they’re buying every slice of attention they can find. Nearly every tech and career influencer I know has pivoted to AI.
16. Startup creation is starting to feel like a factory. I went to a Founders Inc demo day, and it was set up almost exactly like a high school science fair. There were robotics demos in the parking lot, founders standing beside cardboard booths explaining what they’d built, and people wandering around looking at projects. Except some of the founders were 16 and had already raised venture money. YC, HF0, Founders Inc, and others are getting incredibly good at compressing the time between “I want to start something” and “I have a company.”
17. Standing out has never been harder. There are 100s of CRMs, event tools, and AI SDRs launching at once. When everyone can build the product, branding, storytelling, and distribution matter more.
Every time I leave San Francisco, I feel like I got a glimpse of the future a little early.
Some of it is exciting… some of it is strange. But the pace of change here is impossible to ignore.
• • •
📌 Andrew’s Bookmarks
My favorite links to help you be wiser and more creative.
The Art of Being Unreachable by Alexis McElroy – The science and tactics behind becoming a more interesting (and attractive) human.
How to Become a Disgustingly Good Conversationalist by Grace Moser – As someone who had to “learn” conversation, I found this to be gold. Conversation is a skill you can take into any setting.
50 New York City recommendations for weirdly specific situations by Emilie – I’m addicted to this new substack blog about NYC recommendations.
Some final words on Foursquare by Dennis Crowley (Founder) – I’ve been a huge fan of Foursquare since the early days. It was always my go-to for restaurants and bars. This is Dennis’ reflection after Foursquare’s acquisition a month ago. A must-read for every entrepreneur.
• • •
🚀 Fewer than 100 Outliers Summit tickets left
The Outliers Summit is three weeks away, and we’re close to selling out. There are fewer than 100 tickets left.
We just added 10 new speakers. Every one of them built a seven-, eight-, or nine-figure company, and they’re coming to show you exactly how. They join Sam Parr (sold The Hustle to HubSpot), Zach Sims (sold Codecademy for $525M), Ryan Hoover (sold Product Hunt to AngelList), and many more.
Day 1 is for building something real with AI. Day 2 is off-the-record talks from founders who’ve built, scaled, and sold. Plus parties and side events all week.
And every ticket comes with access to $100,000+ in partner credits from Vercel, ElevenLabs, Granola, Datadog, and more.
This is the best room we’ve ever put together. We’d love for you to be in it.
👉 Grab your ticket before we sell out
• • •
💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
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🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.
💡 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.
• • •
🖼️ Behind the Scenes
I went sailing for the first time with my friend Rish on a windy day in San Francisco. At one point, the boat heeled to about 45°. (Heeling is when the wind pushes a sailboat over onto its side.)
My stomach dropped, and I was sure we were going over. I got ready to jump into the water.
The sailors on board barely looked up.
Apparently, a keelboat is designed to do exactly this. There’s a heavy weight at the bottom of the keel, so the further the boat tips, the harder that weight pulls it back upright. In most conditions, it’s nearly impossible to flip.
Many sailboats can be knocked a full 90°, mast touching the water, and still pop back up on their own. But damn that was scary.
These are such cool observations. I found myself saying yes to everything. It's a really wicked time to be in SF rn