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Insight
Kevin Hartz: Sector chasing is flawed; great founders create new segments
“I wouldn't say that I'm a segment investor. I don't kind of believe in chasing different sectors, but instead look for these phenomenal people that really create new segments.”
Kevin Hartz May 22, 2017 ▶ 4:35 20VC: Founders Fund's Kevin Hartz on Why Investing In Silicon Valley Is Broken & Why Fearlessness Is What Makes The Truly Great Investors
Assertion Supported
Lemkin: Founders Fund previously cut its fund size due to deployment constraints
“Founders fund cut their, you know, N minus two funds ago, they cut them because they couldn't think they could deploy enough fund in the, in that window.”
Jason Lemkin Sep 3, 2026 ▶ 53:19 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Assertion Supported
Rajaram: Napoleon Ta decides which companies Founders Fund doubles down on
“The unsung hero of Founder Fund is a guy called Napoleon Tha, who leads a growth practice. And Napoleon basically is the one who decides which of the companies should we double down on.”
Gokul Rajaram Mar 16, 2026 ▶ 56:52 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Opinion
Rajaram: Founders Fund's performance stems from heavily doubling down on winners
“If you look at Founders Fund, which I think is one of the best performing funds, a huge part of their success is basically doubling down on the companies that matter.”
Gokul Rajaram Mar 16, 2026 ▶ 56:41 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Founders Fund closing $6B in new capital after deploying $3.3B in 11 months
“Founders Fund are closing in on six billion dollars of new funds. They invested the last 3.3 in 11 months in amazing businesses like SpaceX and Stripe and Anduril.”
Harry Stebbings Mar 12, 2026 ▶ 50:17 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Assertion Supported
Randle: Delian Asparouhov Sourced the Seed Investment for Ramp
“Dude, you sourced the seed of ramp.”
Everett Randle Nov 10, 2025 ▶ 1:11:45 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Supported
Founders Fund allows deal team members to personally co-invest
“So there's a program, for example, at Founders Fund where anyone that works on an investment or if you're leading an investment, you can personally invest alongside the firm.”
Everett Randle Nov 10, 2025 ▶ 4:13 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Founders Fund wrote record $1B check for Anduril's Series G
“Specifically with regards to Amgrills raising two and a half billion Series G, I don't know if you guys knew this, they got a billion from Founders Fund in this latest round. A billion again, making it their largest ever check, and the Founders Fund's prior la…”
Harry Stebbings Jun 12, 2025 ▶ 25:19 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lemkin: Founders Fund categorized Ramp as fintech to maintain non-B2B stance
“They told them they don't do B to B investing, then that viewed ramp as a fintech.”
Jason Lemkin Apr 17, 2025 ▶ 58:50 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Insight
O'Driscoll: Capital concentration limits prevent fund wipeouts but cap peak returns
“And it is the, and it is exactly right. But now again, to take both sides of that, it is the enemy of greatness and it is the protector of massive wipeouts, right? And it just boils down to the personal choice of where in that dimension you want to be.”
Rory O'Driscoll Apr 17, 2025 ▶ 53:02 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Insight
Asparouhov: Target Internal Critics First When Sponsoring Venture Deals
“You should always go for the path of most resistance when you know, trying to work on a deal at FF. Work and make sure to loop people in from the investment team that are going to be the most critical of the company, given that one, if you're able to get those…”
Delian Asparouhov Jul 29, 2024 ▶ 31:45 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Delian Asparouhov: Peter Thiel incentivizes Founders Fund staff to challenge him
“He values sort of people that are willing to actually sort of disagree and stand up to him so much so that I think it's incentivizes behavior internally where people proactively want to disagree with him more than others.”
Delian Asparouhov Jul 29, 2024 ▶ 48:51 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Assertion Supported
Stephens: Flexport Was First Major Founders Fund Check in 2014
“The first big check that I wrote at Founders Fund was Flexport. And no one was thinking about Supply chain logistics in 2014.”
Trae Stephens Apr 3, 2024 ▶ 14:48 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Disclosure
Stephens: Doing Deals at Founders Fund Requires Pounding the Table
“And in order to get anything through, you literally have to just be pounding the table. Like, it is on you to have the level of conviction that's required to get people on board.”
Trae Stephens Apr 3, 2024 ▶ 17:43 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Disclosure
Stephens: Founders Fund Avoids Board Seats and Operates Purely Reactively
“We don't generally want to take board seats. We are incredibly hands-off and operationally helpful when asked, but only reactively.”
Trae Stephens Apr 3, 2024 ▶ 28:59 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2029
Stephens: Founders Fund Will Always Stick to Traditional Series A Strategy
“Our core vision is we just want to invest in the best founders, building the best companies that are going to be category, category defining. And I think you can do that through a very traditional venture model of, can we get a check into the series A and can …”
Trae Stephens Apr 3, 2024 ▶ 31:27 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Insight
Stephens: Operational Startup Knowledge Decays After Three Years
“The entropy on, like, knowledge of operationally being engaged with the startup is so fast. All the things that I did at Palantir for six years, like, I feel like were relevant for, like, my first three years at Founders Fund.”
Trae Stephens Apr 3, 2024 ▶ 1:07:22 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Insight
Stephens: Great Founders Can Pivot Their Way Into Product-Market Fit
“The founder is the atomic element, a really great founder and team are going to be able to pivot their way into strong product market fit. Whereas a great idea with a weaker founding team are going to get stuck and will likely spin out.”
Trae Stephens Apr 3, 2024 ▶ 38:33 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Insight
Stephens: Investors Should Follow Heuristics Rather Than Justifying Exceptions
“And this is going back to that earlier point I was making about heuristics is that you can't constantly convince yourself that every Exception is actually an exception. Usually it's just wrong. Usually you should just follow your instincts around the heuristic…”
Trae Stephens Apr 3, 2024 ▶ 20:14 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Disclosure
Stephens: Founders Fund Backed Flexport Based on Individual Partner Conviction
“So when I wanted to make the flex board investment, I had to kind of go through the gauntlet and answer a bunch of questions from the team and pound the table. But at the end of the day, they were like, we made a bet on Trey. Trey has high conviction in this. …”
Trae Stephens Apr 3, 2024 ▶ 18:38 Trae Stephens: Why No Company is Successful Because of their VC | E1135 · 20VC with Harry Stebbings
Disclosure
MITIMCo is not invested in Founders Fund but wants to be
“Probably Founders Fund.”
Ryan Akkina Jan 29, 2024 ▶ 56:21 Ryan Akkina: How MIT Builds Their Venture Fund Portfolio & How MIT Approach Direct Investing | E1109 · 20VC with Harry Stebbings
Disclosure
Lacaillade: SCS Financial was one of few early institutional LPs in Founders Fund
“We were one of the only institutions in it. I mean, there were not that many institutions. Now everyone wants to get into it.”
Peter Lacaillade Dec 18, 2023 ▶ 5:29 Peter Lacaillade: Why Now is the Best Time to Invest in Emerging Managers | E1096 · 20VC with Harry Stebbings
Opinion
Corcos Prefers Direct, Full-Contact Investors Like Keith Rabois Over Passive Ones
“Keith from founders fund is known for being pretty full contact. And I. Talk to some people who really did not like working with him, but they didn't like working him. They didn't like working with him for reasons that I would actually enjoy working with him, …”
Sam Corcos Dec 11, 2023 ▶ 54:01 Sam Corcos: Why Founders Should Take as Many VC Meetings as Possible | E1093 · 20VC with Harry Stebbings
Insight
Rabois: Intellectual preparation during downtime drives breakthrough workplace success
“You don't just go to the field and practice all day, 24 seven. You might study film, and like, you might go home and spend four hours watching video of your opponent, and that makes you more successful. So your body is recovering, your, like, your brain is tra…”
Keith Rabois Nov 27, 2023 ▶ 12:58 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Opinion
Stebbings: Top VCs prioritize upside maximization over downside risk
“When I think about Brian Singerman and Pat Grady, They're not worried at all about it going to zero, but they are very worried about upside maximization, and I think you get that uncapped upside lack of fear of downside through immense success.”
Harry Stebbings Oct 18, 2023 ▶ 28:58 Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Mohnot: More venture capital funds will shrink their fund sizes
“I think we'll see more. I think we have to.”
Sheel Mohnot Jul 17, 2023 ▶ 6:22 Sheel Mohnot: How I Got Married in the Metaverse; Founder vs Product vs Market | E1035 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Singerman: Founders Fund clearly saw Airbnb's huge network effect early on
“We definitely saw at the time that the network effect on Airbnb was, at the time, was huge, and yeah, the market was it was clear that they could penetrate into the travel market, or even the lodging market, which I guarantee you, Harry, is huge.”
Brian Singerman Oct 31, 2022 ▶ 15:02 Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
Insight
Singerman: VC fund returns earn complete freedom from LP interference
“When we've made money for people, you have a lot of more latitude on how you can invest money. So you've got. The freedom to do whatever you want without people breathing down your neck.”
Brian Singerman Oct 31, 2022 ▶ 17:49 Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
Disclosure
Singerman: Founders Fund has invested $400 million total into Anduril
“We put more than, we put four hundred million in that company total now. This is just our most recent one was two hundred million.”
Brian Singerman Oct 31, 2022 ▶ 47:24 Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Singerman: 3x returns on $10M checks are meaningless for multi-billion dollar funds
“Our funds are multi-billion dollars, right? Like if we have a. Ten million dollar check, there's no real difference between that going to zero or that going to. Thirty million. I mean, there's just no difference between those numbers.”
Brian Singerman Oct 31, 2022 ▶ 31:41 Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
Disclosure
Singerman: Personal Goal Is Maximizing Return-to-Fame Ratio
“I mean, I try and my life strategy is to maximize my dollars to fame ratio. Like I want to make a lot of returns for myself and LPs and have the minimal amount of fame possible, right?”
Brian Singerman Oct 31, 2022 ▶ 42:20 Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
Disclosure
Singerman: Founders Fund partners each execute distinct individual strategies
“The way that we do things at Founders Fund is everybody runs their own strategy based on what they are the best at.”
Brian Singerman Oct 31, 2022 ▶ 21:21 Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943 · 20VC with Harry Stebbings
Opinion
Sequoia and Founders Fund excel at building deep ownership in winners
“I think Sequoia has always done a good job of this. I think Founders Fund has done a good job of this.”
Logan Bartlett Aug 30, 2022 ▶ 14:11 Logan Bartlett: WTF is Happening at Growth Stage Investing? | 20VC #920 · 20VC with Harry Stebbings
Disclosure
Rabois: Founders Fund lacks team and structure to manage public equities
“At Founders Fund, I don't think we would do that very well. We don't have a team that's really constructed to do that. We don't have the legal structure that's really designed to do that.”
Keith Rabois May 30, 2022 ▶ 17:06 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Every Founders Fund partner operates an independent investment strategy
“Everybody at Founders Fund runs their own strategy, and my strategy is very different from even everybody else's at Founders Fund, let alone other VCs.”
Brian Singerman Nov 11, 2021 ▶ 5:20 20VC: The Anduril Memo: Founders Fund's Brian Singerman on What Makes Palmer Luckey One of the Greatest Innovators in History, Why It Is BS The DOD Do Not Want To Work With Silicon Valley & Why in Venture You Have To Play A Different Game to the Hedge Fun
Assertion Supported
Founders Fund put $40M into SpaceX from a $200M fund
“And I think even Founders Fund, you know, I mean, back, back in Founders Fund too, I mean, SpaceX was a, basically a forty million dollar position out of a two hundred million dollar fund, and it was a rocket company.”
Justin Fishner-Wolfson Feb 4, 2021 ▶ 15:48 20VC: Why VCs Should Care More About Cost of Capital and Less About Ownership, Investing Lessons from working with Peter Thiel at Founders Fund, Why Liquidity Aligns Incentives Between Founders and Investors & Why It Is The Last Double That Matters in Ven
Opinion
Boyle: Brian Singerman Is Silicon Valley's Best Reactive Investor
“The flip side of that is someone like Brian Singerman, who I think is one of the best reactive investors in the Valley, where he has no theses, doesn't think about the future, and just listens to the founder and the story and uses his own frameworks and is abl…”
Katherine Boyle Oct 1, 2020 ▶ 11:31 20VC: What Is Founder Narrative Fit and How to Detect and Invest In It, How To Avoid Consensus Thinking When Investing, Price Sensititivity; When To Pay Up vs Stay Disciplined & From New York Times To General Catalyst; Why Venture and Journalism are Not S
Assertion Supported
Stebbings: Founders Fund lacks traditional Monday partner meetings
“Founders Fund is quite famous for having quite a loose investment decision making process, not with the kind of traditional partner meetings every Monday.”
Harry Stebbings Oct 1, 2020 ▶ 9:15 20VC: What Is Founder Narrative Fit and How to Detect and Invest In It, How To Avoid Consensus Thinking When Investing, Price Sensititivity; When To Pay Up vs Stay Disciplined & From New York Times To General Catalyst; Why Venture and Journalism are Not S
Disclosure
Boyle: General Catalyst Didn't Lead an Anduril Round Until Series B
“With Anderil, we invested in the seed. We also invested in the A, but we didn't lead around until the series B when we co-led with Founders Fund.”
Katherine Boyle Oct 1, 2020 ▶ 27:11 20VC: What Is Founder Narrative Fit and How to Detect and Invest In It, How To Avoid Consensus Thinking When Investing, Price Sensititivity; When To Pay Up vs Stay Disciplined & From New York Times To General Catalyst; Why Venture and Journalism are Not S
Assertion Not checkable as stated
Sequoia, a16z, and Founders Fund enforce strict partner investment discipline
“You look at the likes of Andreessen Horowitz or Sequoia, our founder's fund, for example. They're pretty disciplined in terms of the absolute number of investments they make per person.”
Sumit Gajri Jan 17, 2020 ▶ 47:54 20VC: Portfolio Construction, Optimising SPVs, Opportunity Investing "Between Rounds", Being Distribution-Centric Over Product-Centric and Capital Concentration Within Funds With Sumeet Gajri, Chief Strategy Officer @ Carta
Opinion
Adrian Aoun: Founders Fund and Khosla Ventures treat founders well during downturns
“The investors that I went with in forward, people like Founders Fund or Kosla, Keith Raboy at Kosla, who I know has been on your show. These are people that when times get tough have been good actors.”
Adrian Aoun May 25, 2018 ▶ 27:29 20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward
Insight
VanDevender: Drilling into specific technical details tests a founder's true depth
“Even if you don't necessarily yourself have the complete picture by just, you know, drilling down on specific aspects, you know, whether that person has, like, has all the answers and can go as deep as you want to go is a really good sign.”
Aaron VanDevender Oct 16, 2017 ▶ 6:03 20VC: Founders Fund's Chief Scientist on Why AI Is Mostly A Scam, Why The Value of Large Datasets Is Mostly Overplayed & The Societal Effects of 4m Truck Drivers Being Unemployed with Aaron Vandevender
Opinion
Singerman Considers Affirm's Max Levchin One of History's Best Founders
“Affirm, because it's a ridiculously hard one run by one of the best founders in history with Max Levchin.”
Brian Singerman Jun 5, 2017 ▶ 21:40 20VC: Founders Fund's Brian Singerman on Why VC Is About Upside Maximisation Not Downside Minimisation, Why There Is No Right Way To Do Venture and Why They Do Not Have Monday Morning Partner Meetings At Founders Fund
Disclosure
Founders Fund Explicitly Warns Seed Founders About Potential Signaling Risk
“And so we always, when we're making a small investment, always tell the entrepreneur upfront, like, Hey, this is a potential signaling risk.”
Brian Singerman Jun 5, 2017 ▶ 14:17 20VC: Founders Fund's Brian Singerman on Why VC Is About Upside Maximisation Not Downside Minimisation, Why There Is No Right Way To Do Venture and Why They Do Not Have Monday Morning Partner Meetings At Founders Fund
Disclosure
Many of Founders Fund's Best Deals Started as Small Seed Checks
“A lot of our best investments have been smaller checks That then we've been tracking the closely company closely enough that have grown into larger checks.”
Brian Singerman Jun 5, 2017 ▶ 13:42 20VC: Founders Fund's Brian Singerman on Why VC Is About Upside Maximisation Not Downside Minimisation, Why There Is No Right Way To Do Venture and Why They Do Not Have Monday Morning Partner Meetings At Founders Fund
Disclosure
Hartz: Founders Fund stays sector-agnostic, enabling early investments like SpaceX
“We stay sector agnostic and instead look just at the individuals, and in doing that, that's enabled Founders Fund, and this is far before my time, to be at the ground floor of some very important companies. SpaceX is you know, a grand example of that.”
Kevin Hartz May 22, 2017 ▶ 11:59 20VC: Founders Fund's Kevin Hartz on Why Investing In Silicon Valley Is Broken & Why Fearlessness Is What Makes The Truly Great Investors
Insight
Kevin Hartz: Venture investing requires slowing down compared to fast startup operations
“In a startup, you know, you're trying to move really quickly. You're trying to make decisions and have things happening on the investing side. You really need to kind of tap the brakes or really be prudent about what you jump into.”
Kevin Hartz May 22, 2017 ▶ 7:57 20VC: Founders Fund's Kevin Hartz on Why Investing In Silicon Valley Is Broken & Why Fearlessness Is What Makes The Truly Great Investors
Assertion Supported
Everett Randle joins Benchmark as GP from Founders Fund
“Topic number one, Everett Randall joins Benchmark. Benchmark don't add partners very often. It's a big news announcement that he's joining. Joins Benchmark as their latest GP. He was with Kleiner and he was with Founders Fund before.”
Harry Stebbings Oct 23, 2025 ▶ 0:53 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
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