The Twenty Minute VC

Brian Singerman: How I Became a Partner at Founders Fund, Why We Put $400M into Anduril | 20VC #943

Brian Singerman is a Partner @ Founders Fund, one of the best-performing funds of the last two decades. Among their portfolio, they have the likes of Airbnb, Facebook, Stripe, Anduril, and many more generational-defining companies. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google. ------------------------------- Timestamps: 0:00 How Brian got into the world of venture 1:16 Do you agree with the buy low and sell high principle? 2:55 Does early stage venture need to worry about Macro economics? 4:30 Company valuations and funding prospects 6:48 Did you deploy too fast in 2020-2021? 7:56 Lessons from the last few years 11:18 How do you advise your founders today? 13:22 How much does market matter? 15:24 Are winners obvious early? 16:07 Reserves and cross fund investing 17:31 What gets easier and what’s get harder? 21:58 What makes Founders Fund special? 26:20 Do boards add value? 27:23 How to plan strategy with a founder 28:45 What have you been wrong? 31:22 Advice to fund managers 36:55 How to backchannel when hiring 39:04 How to advise young investors 41:11 Most successful investment ever 42:15 Dollar to fame ratio 43:06 Biggest personal strength and weakness 44:02 Did becoming a father impact your mindset? 45:10 Best board member you’ve worked with 47:07 What makes Anduril so good? --------------------------------- In Today’s Episode with Brian Singerman We Discuss: 1.) From Google to Befriending Sean Parker to Founders Fund: How Brian’s friendship with Sean Parker led to his joining Founders Fund over 15 years ago? What does Brian believe makes Founders Fund such a unique fund? What does Brian know now that he wishes he had known when he started in venture? 2.) The Landscape Today: Where Are We Now? Why does Brian believe there is a huge price mismatch between private vs public companies? How does this impact the pace with which Founders Fund invest? Why does Brian not feel any pressure to invest in this environment? What are the 10 hypergrowth companies that Brian is looking to invest in today? What advice does Brian give to young investors today who are concerned at their first market correction and questioning if they are actually any good at this? 3.) Brian Singerman: The Investor: How does Brian reflect on his own investing style? What is he world-class at? What is he bad at? Why does Brian think boards are a waste of time? What is better than a board? Why does Brian not ever think about reserves? How does Brian answer LPs concerns when they cite them on the topic of cross-fund investing? What does Brian believe is the secret to venture capital? What elements make those at Founders Fund thrive? What characteristics make those that do not work out, fail? 4.) Founders Fund: The Firm: How does Founders Fund structure and optimize its decision-making process today? How does Founders Fund approach the hiring process for all new team members? What one question do they need to be able to clearly answer with all team members joining? How do Founders Fund approach the reference checking process for all new hires? What questions do they find most revealing of the true talent of the candidate? What are the single biggest hiring mistakes Brian has made? What did he learn from them? --------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/brian-singerman/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Brian Singerman on Twitter: https://twitter.com/briansin Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok --------------------------------- #VentureCapital #FoundersFund #BrianSingerman #HarryStebbings #20VC #Venturecapitalist #Anduril

Harry StebbingshostBrian Singermanguest

Oct 30, 202249mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Brian Singerman on Upside-Obsessed Venture, Pricing Discipline, Anduril Bet

Brian Singerman, partner at Founders Fund, explains his venture philosophy: put the most money possible into the best founders in the biggest markets at the best achievable price, and ignore everything else. He argues traditional concepts like “buy low, sell high” and elaborate downside protection structures are largely irrelevant for true upside-driven venture capital. Much of the conversation centers on today’s pricing mismatch between public and private markets, his deliberate slowdown in deployment, and why Anduril is the one company he backed with a massive $400M across funds. He also discusses sourcing as Founders Fund’s biggest controllable challenge, their “no dogma, adapt-or-die” culture, and how they hire uniquely differentiated partners rather than clones.

IDEAS WORTH REMEMBERING

5 ideas

Venture is about upside maximization, not buy-low-sell-high timing.

Singerman argues that because venture outcomes play out over a decade and span multiple macro cycles, trying to time markets like a public investor is misguided; the job is to back exceptional companies at non-ridiculous prices and aim for fund-returners, not optimize small multiples.

Pay attention to macro, but don’t try to predict it.

He acknowledges macro conditions affect pricing and fundraising (e.g., the 2022 public-private valuation mismatch), but insists nobody can reliably forecast macro trends, so founders and investors should operate as if today’s environment persists and make pragmatic decisions now.

Only invest heavily when price and quality align—otherwise, wait.

Founders Fund feels no pressure to deploy capital; Singerman has drastically slowed investing because great companies still want 2021-era valuations, with Anduril being the lone large check he wrote in 2022 where quality and price made sense.

Fund size should match the largest check you’re truly comfortable writing.

He advises emerging managers to raise the smallest fund they can dominate, and to size funds so that writing a 25–30% of fund check feels realistic; his comfort with $200M–$500M checks justifies multi-billion-dollar funds, but he warns that scaling fund size materially increases difficulty of strong returns.

Founders plus big markets plus real moats are non-negotiable.

Founder quality is 80–90% of his thesis, but a small market cannot move a multi-billion-dollar fund; he looks for uniquely advantaged teams attacking truly large markets with defensible moats, as he saw with Airbnb’s network effects and Anduril’s tech, talent, and timing in defense.

WORDS WORTH SAVING

5 quotes

Venture capital is a game of upside maximization. You’re not trying to minimize your downside.

— Brian Singerman

If you’re waiting around for perfect information, you’re going to be terrible at this job.

— Brian Singerman

We feel zero pressure to invest capital. We can just wait until prices actually catch up.

— Brian Singerman

Put the most money possible into the best companies possible at the best price possible. That’s venture capital.

— Brian Singerman

My life strategy is to maximize my dollars-to-fame ratio.

— Brian Singerman

Brian Singerman’s path into venture and joining Founders FundHow true venture investing differs from public markets and macro timingCurrent market environment, pricing mismatches, and deployment pacingUpside maximization, fund size strategy, and very large single-check betsEvaluating founders, markets, and moats (including Airbnb and Anduril)Sourcing vs. picking vs. winning deals, and the role of brandFounders Fund’s internal culture, hiring philosophy, and views on boards/advice

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