Most important take away

Capital expansion follows Boyle’s Law: founders will spend whatever they raise and hit the same milestones, so raising too much too early destroys discipline and quietly kills great companies. The winning playbook is to back spiky individual founders early, concentrate into power-law winners, and sit on them for life rather than trim winners on the way up.

Summary

Actionable insights and patterns from Kevin Hartz, co-founder of Eventbrite and GP of A*, drawn from a career that includes seed checks into Airbnb, Pinterest, PayPal, and Ramp.

Career and founder advice

• Optimize for learning and avoiding boredom, not for an “inevitability of success” narrative. Hartz had a normal middle-class upbringing and a post-college identity crisis, then landed in Silicon Valley at the right moment.
• Great founders almost always show entrepreneurial behavior early (selling things as a teen, side hustles in college). They also tend to be binary about school - they either love it or hate it - and disproportionately have ADHD.
• The single most important variable is the spikiness of the best founder, not the well-roundedness of the team. Matt Clifford’s lesson from 10 years of Entrepreneur First confirms it: bet on the spikiest point of the strongest individual.
• First-time founders are messier but spikier; serial founders make fewer mistakes but lose some of the fearless creativity that produces Beatles-tier companies.
• Overcoming real obstacles is a strong signal. Hartz looks for founders who have “moved mountains.”

Investing patterns and discipline

• Capital is the enemy of discipline. Raise $1M and you build a $1M company; raise $5M and you build the same company for 5x the cost. The current environment has too much capital and too little hands-on help, and great founders drift without checks and balances.
• Pick a governance philosophy on a spectrum: Sequoia-style hands-on help vs. Founders Fund-style “give Elon the money and get out of the way.” Hartz leans Sequoia because oversight and a star chamber of operators shortcut common mistakes.
• Don’t sell on the way up. Power-law winners dwarf everything; sit on companies for life. Angel money can ride freely, but fund money introduces LP-driven liquidity pressure - know which game you’re playing.
• The capital concentration limit is the enemy of great venture returns (Brian Singerman). Founders Fund sold Spotify at $8B and rolled it into Airbnb at $2.5B - double down on conviction.
• Don’t do TAM-only analysis. Great teams slingshot from small markets into big ones. Bessemer’s own memos show Procore went from $300M to $10B+ and Snap from $500M valuation to public - you always underestimate the size of your biggest winners.
• When everyone says “the B is dead” or “C is dead,” that’s the time to heavily canvas the area.
• Average $25M seed pricing for hot rounds is brutal. Multi-stage funds and operator-angels (Collisons, Dylan Field, Daniel Gross) have made traditional seed harder than ever.

Talent and meeting craft

• Every founder meeting can change generations of your life. Never be off, even on your worst day. Stay positive and listen hard.
• Be sincere, not slick. Don’t try to “win” a deal - earn the right to work with a founder for years. Salesmanship as deception is a red flag.
• Be careful with brutal honesty. Saying “I don’t believe in you” rarely helps; offer constructive framing (complementary co-founder, specific skill gap) or politely exit. Time is short.

Round dynamics and term sheets

• Exploding term sheets work but you don’t forget them. Hartz and Keith Rabois gave one to Airbnb and Paul Graham privately chided them; they still got cut in. Founders shopping a term sheet is also bad behavior - both sides need to unhook.
• You can’t lock founders down. Use honey, not vinegar. Patience is the single most important variable - the great companies often take a long, wandering path.
• On reserves: A* runs a 70/30 barbell of pre-seed/seed plus selective Bs ($10-20M checks).

Operator vs. journalist vs. banker as VC

• Operators are not automatically better investors. Operator-investors are often harder on founders than VCs (“I missed my numbers too, quit whimpering”). Michael Moritz (journalist), Bill Gurley (banker), and Jeremy Levine (never operated) are proof points that the operator-required dogma is dead.

Lessons from his mentors

• Peter Thiel: sees the world through a different lens; his throwaway lines become indelible years later. Go all-in on the people you believe in (Hartz regrets passing on joining PayPal and on joining Palantir at founding).
• Roelof Botha: be calm and metered when the ship is being thrown around; bring sound judgment in a crisis. Counterintuitive Roelof-ism - when things go badly, be supportive and nurturing; when things go great, dig in hard with tough love.
• Pierre Lamond: relentless excellence. Force-rank your direct reports and fire the bottom one - the signal of zero tolerance for mediocrity matters more than the individual decision.

Misses, hits, and timing

• Biggest miss: passed on YouTube when Chad Hurley pitched it; was burnt out leaving Xoom. Lesson: never let your mindset poison a meeting.
• Biggest zero: Talkbox - early live video, even Sequoia and Tony Bates couldn’t save it. Scaling and PMF failed.
• Sold-too-late lessons: OpenSea seed was at $13.5B during the 21/22 boom; should have at least taken some off the table even if compounding favors holding.
• Bitcoin seed conviction: invested via Pinterest’s Wences Casares in October 2011.

Macro thesis

• We are in the early years of the biggest bubble. NVIDIA as the most valuable company is the precursor to the AI bubble of all bubbles, compounding with crypto, fintech, clean energy, and industrial biotech bubbles. Build apps on top of the transformer platform - the why-now is clear.
• The defining illnesses of this era are neurological - depression, bipolar, addiction, eating disorders, Alzheimer’s. Hartz’s daughter is in treatment for a severe eating disorder; he argues this is the next “war on cancer” - and a major investment frontier.
• Attention economy is more competitive than the compute economy. Founders dramatically underestimate this.
• Look 3-5-7 years ahead, not at what’s working now. Mimetic duplication kills returns.

Practical angel-investor advice

• Write off the money mentally. You need many at-bats.
• Write the same size check every time (e.g., $50K). Your conviction calibration isn’t good enough yet to vary check size.
• Plan for ~$40M in venture deployed before you really know what you’re doing (Don Valentine corollary).

Fund admiration

• VY Capital (John Herring, Alexander Tomas): style, pace, patience, wisdom; truly focused on mega outcomes.
• Y Combinator: every cohort the valley declares them dead, then they produce another generation of giants. Gary Tan’s return is a big deal.

Chapter Summaries

1. Childhood and origin. Hartz grew up middle-class with no adversity narrative, hit a post-college identity crisis, and landed in Silicon Valley at the right time. Was always doing side hustles, including a pre-internet “Facebook” of Stanford student photos called Faces in the Crowd.

2. Mentors - Thiel, Botha, Lamond. Thiel sees the world through a different lens with indelible insights. Botha brings calm metered judgment in crises. Lamond demands excellence (the force-rank-and-fire-the-bottom story).

3. Talent identification. Look for founders who started early, were binary about school, often had ADHD, and overcame real obstacles. Bet on the spikiest individual rather than well-rounded teams.

4. Too much capital. Boyle’s Law applied to capital - founders spend whatever they raise. Today’s environment has abundant money but little hands-on help. Hartz leans toward the Sequoia hands-on model over Founders Fund’s hands-off philosophy.

5. Airbnb seed. Sequoia outbid Hartz/Rabois/Karim but cut them in; the company popped to $1B by 2011/12 before they could concentrate capital. He frames Airbnb as “distributed storage for people.”

6. Selling vs. holding. Sit on power-law winners for life. Angel mindset (let it ride) differs from fund mindset (LP liquidity pressure). OpenSea regret - should have sold some at $13.5B.

7. A* and current strategy. $300M fund two, $600M AUM, 70/30 pre-seed-seed plus selective Bs ($10-20M checks). Double-digit ownership targets but flexible.

8. Seed market today. Average $25M entry pricing makes seed brutal. Multi-stage funds and operator-angels are heavy competition. Less cooperation than past eras.

9. Operators vs. non-operators as VCs. Operator status is not required - Moritz, Gurley, Levine prove it. Operator-investors can actually be tougher on founders than pure VCs.

10. Exploding term sheets and shopping. Hartz/Rabois gave one to Airbnb and Paul Graham privately chided them. Both founder shopping and investor lockdown are bad behaviors. Use patience and honey, not handcuffs.

11. Misses and zeros. Passed on YouTube during a low moment. Talkbox was the biggest zero. Lesson: always be present in founder meetings; one meeting can change generations.

12. Reserves, B-rounds, and TAM. Bs are a great place to be when everyone calls them dead (Hartz wrote a B into Wiz). Skip TAM-heavy analysis - great teams slingshot from small markets.

13. Risk-taking regrets. Should have joined PayPal and Palantir when Thiel offered. Lesson: when someone you believe in says go, go all-in.

14. Founders Fund lessons. Conviction-driven model, no concentration limits on winners, Spotify-into-Airbnb story. Voting structures in partnerships are “complete bullshit” - if you trust your partner, let them do deals.

15. Supporting founders. Roelof-ism: nurture in bad times, push hard in good times. Match support style to what each founder needs.

16. Parenting and mental health. Hartz’s 16-year-old daughter has been hospitalized three times for an eating disorder; treatments are barbaric and lack scientific rigor. Neurological illness is the defining medical frontier of the era.

17. Quick-fire. Defense tech ascent surprised him. Most respected fund: VY Capital. Angel advice: write off the money, take many same-sized swings. Most desired portfolio swap: YC. The bubble of all bubbles is just beginning - AI, crypto, fintech, clean energy, industrial biotech all compounding.