Sam Altman

Altman is a prolific early-stage investor who backs deep tech and moonshot ideas. His portfolio through YC and personal investments includes hundreds of companies.

His personal bets tend toward civilizational-scale technology — nuclear fusion, longevity research, AI safety. He has said he thinks the most important investments of the next decade will be in energy and AI.

He also holds significant OpenAI equity (though the exact structure is complex given it was a nonprofit converted to capped-profit).

Naval Ravikant

Naval is an early-stage angel investor who backs founders he believes are building something real in large markets. He does not run a traditional fund.

He invests personally and through AngelList's syndicate model. His edge is pattern recognition built from hundreds of investments and deep engagement with the startup ecosystem.

He has said the best investments are in people, not companies — he bets on the founder's unique insight and personal character. He is known for saying yes or no quickly and not wasting founders' time.

Sam Altman

Altman believes we are approaching AGI — artificial general intelligence — and that it will be the most transformative and potentially dangerous technology humans have ever built. He thinks the right response is to build it carefully rather than cede the frontier to those who might not.

He argues that the returns from AI will be so large they will need to be distributed broadly to prevent catastrophic inequality. He has floated ideas around universal basic income funded by AI productivity.

Naval Ravikant

His wealth philosophy has been distilled into what people call "How to Get Rich" — a tweetstorm and podcast that has been read or heard by millions. The core thesis: specific knowledge (what you know that cannot be taught), leverage (code, media, capital that works while you sleep), and judgment.

He argues that wealth is built by owning equity in things, not selling your time. He is deeply skeptical of trading time for money as a long-term strategy.

Sam Altman

Altman has said that playing it safe at this moment in history is the most dangerous thing he could do. His belief: AGI is coming whether OpenAI builds it or not — the only question is who builds it and with what values.

That conviction makes conventional risk aversion feel irresponsible to him. He holds large personal positions in nuclear fusion companies and longevity biotech — bets that could return 1000x or go to zero.

He has said that any genuinely interesting bet carries existential downside risk. That is what makes it interesting, not a reason to avoid it.

Naval Ravikant

Naval's approach to angel investing is explicitly probabilistic: make many small bets, expect most to fail, and let the power-law distribution of outcomes do the work. He does not try to pick the single winner from first principles — he backs enough founders with genuine specific knowledge that the portfolio math works.

His personal risk tolerance for volatility is high: he has held Bitcoin since the early years and sat through multiple 80% drawdowns without selling. He has argued that diversification is the wrong framework for early-stage investing — the returns are so concentrated in outliers that you want maximum exposure to them.

Sam Altman

He has written about sleeping 8 hours, exercise, not scheduling meetings before 11am, eating the same lunch every day, and blocking large chunks of uninterrupted time for thinking. He is a known prepper — he has said he owns land, gold, guns, and antibiotics in case civilization collapses, which is a mildly alarming admission from the CEO of the company building AGI.

Naval Ravikant

Naval meditates daily. He has spoken extensively about his morning routine prioritizing mental clarity before business.

He does not schedule many calls. He reads constantly — physics, philosophy, mathematics — not just business books.

He has said he stopped tracking metrics of his personal investments obsessively because it created anxiety without changing his decisions. He does not hustle culture — he works deeply on fewer things.

Sam Altman

OpenAI and ChatGPT. The launch of ChatGPT in November 2022 was the most consequential product launch in tech in at least a decade.

It brought AI from a niche technical field into mainstream awareness overnight and made OpenAI the fastest-growing AI company in history. Altman navigated the transition from nonprofit to commercial entity, secured $13 billion from Microsoft, and built a company valued at $157 billion within five years.

Naval Ravikant

His early Twitter investment. He invested at the seed stage, when Twitter was a chaotic early-stage startup with no clear business model.

It eventually went public at a $14 billion valuation and was acquired by Elon Musk for $44 billion. His Uber investment is another frequently cited win — he was in very early before it became the most valuable private company in history.

Sam Altman

Being fired by his own board in November 2023 — and the board's subsequent reversal. Whatever actually happened in those five days is still murky.

What is clear is that the board lost control of the situation the moment it became obvious that without Altman, most of the company would leave. The board members who voted to fire him are gone.

Altman is back with more power. The episode revealed real governance problems at one of the most consequential companies in history.

Naval Ravikant

The Epinions lawsuit. After Epinions was sold and merged into Shopping.com, a group of early employees sued over equity that they felt was improperly restructured.

The legal battle was bruising and public, and Naval has spoken about the experience as one of the hardest of his professional life. He has said it taught him more about founder ethics and equity structure than anything else.

Sam Altman

Sam Altman dropped out of Stanford in 2005 to co-found Loopt, a location-sharing startup. Loopt was acquired in 2012 for $43 million — not a huge exit but enough to establish him as a serious founder.

He then became president of Y Combinator in 2014, succeeding Paul Graham. Under Altman, YC expanded from a small cohort model to a much larger operation with global reach, including backing Airbnb, Dropbox, Stripe, and hundreds of others in its portfolio.

In 2019, he stepped down from YC to become CEO of OpenAI. The company launched ChatGPT in November 2022, which became the fastest-growing consumer application in history — 100 million users in two months.

In November 2023, the board fired him. The entire company revolted.

Microsoft — OpenAI's biggest investor — nearly hired him to run a new AI division. Five days later, he was reinstated with a restructured board.

OpenAI's valuation hit $157 billion by 2024.

Naval Ravikant

Naval Ravikant was born in New Delhi, moved to New York at age 9. He put himself through Dartmouth on scholarships and loans.

He co-founded Epinions in 1999 — a consumer review site that later became part of Shopping.com. Epinions had a messy founding story that resulted in lawsuits and fractured relationships with early team members.

He then co-founded Vast.com, an online marketplace. In 2010, he co-founded AngelList — a platform that democratized startup investing by allowing accredited investors to co-invest alongside top angels.

AngelList revolutionized the seed stage funding ecosystem. Through AngelList and personal angel investments, Naval has backed over 200 companies including Twitter, Uber, FourSquare, Yammer, and many others.

Several of these became multi-billion dollar companies.

Sam Altman

OpenAI (CEO). Y Combinator (former president).

Loopt (co-founder, acquired 2012). Personal investments via Sam Altman Fund and early-stage bets.

Notable: invested early in Stripe (now worth $70B+), Helion Energy (nuclear fusion), Retro Biosciences (longevity). Also holds equity in Anthropic indirectly.

Naval Ravikant

AngelList (co-founder, 2010). Epinions (co-founder, 1999 — led to Shopping.com).

Vast.com (co-founder). Angel investments in: Twitter, Uber, FourSquare, Yammer, Poshmark, and 200+ others.

The Almanack of Naval Ravikant (compiled by Eric Jorgenson from his public content).

Sam Altman

Stanford University — studied computer science. Dropped out in 2005 after his sophomore year to found Loopt.

Naval Ravikant

Dartmouth College — Bachelor of Science in computer science and economics, 1995.