20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything
Most important take away
The most competitive, consensus deals are typically the worst because hype is negatively correlated with outcomes — only non-consensus conviction bets in large, neglected markets produce the $10B+ winners that move a fund. Founders (not VCs) build successful companies, so the job of an investor is to back high-conviction people in big categories, maximize upside (ignore downside protection and loss ratios), and avoid the memetic contagion that drives bad investment decisions at peak cycles like 2021 — mistakes the industry is already repeating in 2024.
Summary
Actionable insights and career advice:
- Persistence pays in ways credentials don’t: Trae got into Georgetown by physically flying to DC and camping on the admissions office doorstep after being rejected. Lesson: when the standard process screens you out, create a non-standard channel.
- Volume creates pattern recognition: In his first year at Founders Fund, Trae did ~500 pitch meetings with “no standards.” You can’t shortcut taste — you have to see enough to calibrate.
- Run your own book: Founders Fund has no Monday partner meetings on purpose. Heavy process leads to mediocre, consensus outcomes; forcing individual investors to pound the table ensures only high-conviction bets get done.
- The worst deals are the most competitive deals: They’re consensus, expensive at every round, and EV decreases. Memetic contagion in hot markets (sitting on Sand Hill, AI hype today) destroys returns. Founders Fund deliberately stayed off Sand Hill to avoid it.
- Exploding term sheets and 24-hour deadlines signal manipulation; running a transparent, week-long process is responsible founder behavior.
- We didn’t learn from ZIRP. The same 2021 mistakes (overpriced rounds, hostage-style processes) are happening again in AI in 2024. 2-on-20 rounds auto-exclude top firms because a lead can only get ~7.8% — not worth their time.
- Upside maximization, not downside protection: For a $1B fund, only $10B+ category-defining winners matter. Loss ratio is irrelevant — everything else rounds to zero. Pro-rata reserves are “lazy”; only deploy follow-ons where you have conviction to double, triple, quadruple down.
- Founders > markets, but great founders pick great markets. The founder is the atomic unit. Watch for completeness of team — a brilliant solo technical or sales founder without complementary co-founders often fails on recruiting and execution.
- Momentum is visceral and shows up in the first ~6 months, even in deep tech. The best companies are awesome at every stage; the “long trough then breakout” pattern is the exception, not the rule.
- VCs are not specialists — they’re “journalists” with shallow knowledge across many areas. Don’t predict the future from a thesis; let great founders convince you of timing. If you have a thesis on a category but missed the core monopoly winner (SpaceX, Coinbase, Palantir), you’re already losing money.
- “Competition is for losers” applies to VC too. The industry is commoditizing, but returns remain concentrated — differentiation is survival.
- Don’t take VCs on your board. “Any company that’s successful is not successful because their VCs are smart.” Best advice comes from operators/founders, accessed informally without governance overhead.
- Choose good quests: Don’t waste world-class talent on commodity enterprise SaaS or “George Clooney tequila” plays. Aim for things that impact humanity.
- Hard tech requires a business co-founder as strong as the technical founder. Palantir, SpaceX, Anduril were all co-founded by billionaires because hard tech requires surviving long capital droughts while sales motions mature.
- Selling to government is a learned, deliberate skill: Anduril hired a lobbyist in week one. “Field of dreams” doesn’t work — government relations, narrative, agency education, and shifting development risk off the customer are all required from day one.
- Modern defense pivot: The Cold War platform-centric model (huge expensive systems vs. peer states) doesn’t apply to great-power conflict featuring drone swarms and autonomy. You can’t shoot $2M Patriots at $150K cruise missiles forever.
- Personal scaling: Trae runs deals at Founders Fund, runs part of Anduril, and protects family time (breakfasts, school drop-off, dinners). Keys: world-class EA, chief of staff, a high-trust exec team, and strategic use of “no.”
- Being an active operator (Anduril) makes you a much better investor — operational knowledge decays in ~3 years if you’re not in the trenches.
- The future of venture may be founder-investors. Operators give the most useful advice because they’ve actually lived the problems.
- On meaning: Money simplifies tedium but doesn’t fill the void. Vocation matters — invest in things that move humanity toward a better future, not science-fiction dystopias (vice, addiction, loneliness).
Chapter Summaries
- Childhood and Georgetown: Rural Ohio upbringing in a log cabin; “American teenager in a British body.” Rejected by 5 of 9 colleges and dumped by his girlfriend same day. Flew to DC, camped on the dean of admissions’ doorstep, got waitlisted, got in, and worked for the university president for all four years.
- Cultural neglect of rural America: Elite admissions ignore lower-middle-class rural communities, fueling populism. Peter Thiel’s Thiel Fellowship was a response to elite-university cultural distortion.
- Joining Founders Fund: Peter Thiel cold-called Trae at Palantir in 2013. Bad interviews stretched 9 months; eventually got an offer. Brian Singerman’s advice: do 500+ pitch meetings with zero standards to calibrate taste.
- Investing heuristics and biases: Humans rationalize exceptions to their own rules — fighting cognitive bias requires accountability. Trae’s “fairway” deal: huge old market untouched by tech, with a founder who knows the inside baseball (e.g., Flexport, Anduril).
- Process and decision-making at Founders Fund: No Monday partner meetings. Each partner runs their own strategy. High-conviction individuals must pound the table; if the willpower isn’t there, the deal doesn’t happen.
- Competition, price, and memetic contagion: Hot consensus deals are usually bad investments. Founders Fund deliberately avoided Sand Hill. Exploding term sheets are manipulation.
- ZIRP lessons (not) learned: Trae nearly quit VC during 2021 due to “gross” founder-driven hostage processes. We’re repeating those mistakes in AI in 2024.
- State of venture: Industry has commoditized but returns remain concentrated. Founders Fund sits between boutique and capital accumulator. ~$1B fund size keeps them disciplined.
- Reserves, downside, and loss ratios: Pro-rata is lazy. Downside protection is silly at their scale. Only $10B+ winners move the needle.
- Founders vs. markets: Founder is atomic. Team completeness matters. Trae regrets missing recruiting weakness in some bets.
- Momentum and pacing: Great companies feel awesome at every stage. Trough-then-breakout is rare.
- Market timing and theses: VCs are journalists, not specialists. Founders communicate market timing; the core monopoly investment is the only one that matters in a category.
- Founding Anduril: 10 years in national security made the gap obvious — software-defined warfare matters as we shift from counterinsurgency to great-power conflict. Drone swarms vs. Patriot missiles is unsustainable economics.
- Selling to government: Hire lobbyists day one. Government relations, narrative, and shifting risk off the customer are required. Most defense startups fail because they think building cool tech is enough.
- Founding team economics: Hard tech needs a business co-founder as strong as the technical one. Billionaire co-founders historically funded the long sales-cycle survival.
- Geopolitics and ethics: Anduril doesn’t choose customers — the US State Department/DoD controls arms transfers. Trae sees Western political mediocrity as a civilizational risk.
- Personal operating system: Family breakfasts and dinners are protected. World-class EA and chief of staff drive prioritization. Days bounce reactively between Founders Fund and Anduril.
- Faith and vocation: Vocation as service. Avoids “vice” investments (addiction, loneliness) even when profitable.
- Quickfire round: First 18 months of parenthood are hardest but worth it. Hype negatively correlates with outcomes. Don’t take VCs on boards. Money doesn’t bring meaning. Anduril could be a $100B+ company at a fraction of Lockheed’s revenue. Long-term: return to civil service (but not elected office — his wife vetoed it).