serial entrepreneur: co-founder of https://xitter.cf/t.co/G1a4HoHpHS, Spinner, Crackle, Brondell. & 6 kids.

Bay Area, CA
Joined November 2008
Fun milestone at @freestylevc. In 2013, I led seed rounds in both @airtable AND @intercom. $700K each. $7M post. 10% ownership. Same $26M fund. 13 years later — $2B+ exits, weeks apart. But the exits aren't the story. The playbook is.
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Thanks for showcasing @freestylevc -- Proud we are ...
New from me in @NewcomerMedia: Airtable’s Sale to Bending Spoons Wasn’t a Dream Venture Exit. Still, Timing Can Be Everything. Airtable’s definitive agreement on Tuesday to sell to European roll-up juggernaut Bending Spoons at an enterprise value of $1.285 billion could be just a taste of the disappointing exits in store for pre-AI software-as-a-service companies. Airtable, founded in 2013, had around $480 million in ARR and was growing more than 20% year-over-year at the time of the deal. That still wasn't enough in an era of supercharged AI growth and worries that agentic coding will kill software companies. Even counting the roughly $965 million in cash, that brings the deal's equity value to $2.25 billion, it's a steep discount to Airtable's pandemic-era $11.7 billion valuation. Still, smart investors find a way to make money. Venture can be a timing game. While Airtable’s exit may not play as well into the lifetime-partner narrative many VCs push, strategically planned cash-outs made some VCs quite a pretty penny even though the ultimate outcome was underwhelming. @freestylevc GP Dave Samuel (@dsamuel) is one investor in Airtable who cashed out at the right time. Samuel wrote Freestyle’s first check into Airtable’s first funding round in March of 2013 for about 10% ownership at a less-than-$10 million valuation before other investors came in, we heard. Freestyle followed on through the Series B round. The two teams’ relationship went back years before: Samuel had met Airtable CEO Howie Liu when Liu was still a senior at Duke University, and Liu served as Freestyle’s first intern right after the fund’s launch. Liu’s first post-college job was at a Freestyle portfolio company. As a general house rule, Freestyle sells some shares of its portfolio companies once they hit a unicorn valuation. Freestyle exited a significant amount of its position in 2021 at Airtable’s peak valuation of $11.7 billion. While the exact share count couldn’t be learned, Freestyle’s multiple on invested capital will be more than 55x, we heard (The Wall Street Journal previously reported on Freestyle’s multiple).
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Sell some when your winner hits: $1B → $2B → $5B → definitely $10B Thanks to @howieliu, @eoghan, and everyone in these journeys. Great coverage from @EricNewcomer on the Airtable dynamics: newcomer.co/p/saas-shudders-…
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PS. Check our @freestylevc 's new Website. Yep, I vibe coded with Manus: freestyle.vc/?persona=Airtab… Create your favorite VC persona ...
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Fuck Yeah Spencer! Keep fighting for us. No more career politicians that get Less than Zero completed. Go Pratt Go. No gloves now that no Campaign rules.
I love this guy @spencerpratt losing might end up as a win for LA Keep fighting ⚔️
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Historic Moment: Being in Times Square, watching the LiftOff of SPCX. Amy & I saw some of our friends on the Big Video wall … including Mr Steve @FutureJurvetson
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This was just erected in Times Square. I’d love for all Elon Haters to be deported to a world where Elon never existed. What is that world for them?!? Also, can someone erect a Mamdani blowup right next to this, pretty please?
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so Good! Neo Mahan kicking some Ass.
This quoted post is unavailable.
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Nice to see @MattMahanSJ with some AI creative content ...
Matt Thankfully chose the Golden Pill!
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2 years ago: What would the @Polymarket odds be for SpaceX owning Twitter (X)?? 500 to 1? Amazing how @elonmusk is playing 5D chess years in advance of everyone else.
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Go @AngelList ! I'm a proud Angel investor in Naval's seed round. Closed Jan 11, 2011!
Introducing USVC - a single basket of high-growth venture capital, for everyone. No accreditation required, SEC-registered, and a very low $500 minimum. Includes OpenAI, Anthropic, xAI, Sierra, Crusoe, Legora, and Vercel. As USVC adds more companies, investors will own a piece of that too. Liquidity typically comes when companies exit, but we’re aiming to let investors redeem up to 5% of the fund every quarter. This isn’t guaranteed, but if we can make it work, you won’t be locked up like in a traditional venture fund. It runs on AngelList, which already supports $125 billion of investor capital. And I’ve joined USVC as the Chairman of its Investment Committee. — Go back to the 1500s, you set sail for the new world to find tons of gold - that was adventure capital. Early-stage technology is the modern version. It says we are going to create something new, and it’s risky. It’s daring. But ordinary people can’t invest until it’s old, until it’s no longer interesting, until everybody has access to it. By the time a stock IPOs, most of the alpha is gone. The adventure is gone. Public market investors are literally last in line. This problem has become farcical in the last decade. Startups are reaching trillion dollar valuations in the private markets while ordinary investors have their noses up to the glass, wondering when they’ll be let in. Investing in private markets isn’t easy. You need feet on the ground. You need judgment built over years. Most people don’t have the patience to wait ten or twenty years for an investment to come to fruition. But there is no more productive, harder-working way to deploy a dollar than in true venture capital. USVC enables you to invest in venture capital in a broad, accessible, professionally-managed way, through a single basket of innovation, focused on high-growth startups, at all stages. It is how you bet on the future of tech: the smartest young people in the world, working insane hours, leveraged to the max, with code, hardware, capital, media, and community. Your dollar doesn’t work harder anywhere. There is an old line - in the future, either you are telling a computer what to do, or a computer is telling you what to do. You don’t want to be on the wrong side of that transaction. USVC lets you buy the future, but you buy it now. Then you wait, and if you are right, you get paid. Get access here: usvc.com
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I’m already working on a model that FaceTime’s digital Dave with my parents when they call. Then sends me a summary of what I learned. And digital me potentially agreed to.
There is a prediction circulating in AI circles right now that most people are not taking seriously enough and the data says they should be. Within the next year or two, if you work remotely, your company will be able to create a digital twin of you. A model that speaks like you, writes like you, has learned from everything you have done right and wrong, your tone, your judgment calls, your workflow. It will be you on the other side of Zoom or Slack and no one could tell the difference. The harder question, the one nobody wants to sit with is whether it will actually be worse at your job than you are. Probably not. It will never sleep and it will always learn from its mistakes and it will cost 10 to 100 times less than you do and is tax deductible on top of that. The data is not speculative at this point. Anthropic's own labor market report pulled from millions of real Claude conversations found that AI can already theoretically automate 94% of tasks in computer and math occupations, 60-80% across law, office work, and tech. Actual usage is still at 10-20% of that potential which means we are in the early innings of the gap closing. Companies already know what direction this is headed. One in five companies replaced specific roles with AI in 2025 and by end of 2026, 30-37% plan to do so. Amazon cut 14,000 corporate jobs citing AI, Klarna replaced 700 customer service workers, Duolingo offboarded 10% of its contractor workforce. Anthropic's own first internal role eliminated was the engineer who reviewed Claude Code releases before they went to production. The argument from the clip is that the human in the loop is approaching the point of being a liability, the dumbest person on a team that is otherwise AI. That inflection point, by this estimate, is somewhere in the next 900 days.
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Winning post of the Week!
Oh great and powerful @DarioAmodei - builder of minds, father of Claude. I humbly request you leave payroll to us at Deel. We are but simple folk who process paystubs and chase compliance deadlines. But if you do come for us, call me first 🙏
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Software is being swallowed by AI
This leaked AI model from Anthropic just erased $14.5B from cybersecurity stocks in a single day. Claude Mythos quietly surfaced before launch and the numbers shocked everyone. It can detect and respond to threats at near team-level capability, Tasks that needed full security teams… now done by a model. Markets didn’t wait. → CrowdStrike ↓ 5.85% → Palo Alto Networks ↓ 6.43% → Zscaler ↓ 5.89% One question got priced in instantly: If AI can replace the system… what happens to the companies built on top of it? This isn’t just a model upgrade. It’s the first real signal that AI isn’t assisting industries anymore it’s starting to replace them.
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The most important thing nobody is saying clearly enough: AI isn't disrupting entry-level jobs. It's removing the rung entirely. Junior analyst. Associate attorney. First-year engineer. These roles were never just paychecks — they were the on-ramp. How you learned. How you proved yourself. How you built a career. The ladder still exists. The bottom step doesn't.
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A 10x economy sounds amazing on paper. But abundance at the system level does not mean safety at the human level. The future may get extraordinarily bright. But before that, for a lot of people, it gets very dark. xitter.cf/dsamuel/status/2036301…
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