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.

Bill Gates

Gates invests through Cascade Investment LLC in established, cash-generative businesses — railroads, waste management, agricultural equipment, farmland. His biggest single Cascade holding for years was Canadian National Railway.

He has sold most of his Microsoft stock over time. His investment philosophy outside Microsoft mirrors Buffett's: durable businesses with pricing power, bought at reasonable prices.

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.

Bill Gates

His core framework: read obsessively, think long-term, and separate emotion from analysis. He takes annual Think Weeks — solo retreats to a lake cottage in the Pacific Northwest where he reads papers and books for two weeks with no interruptions.

He publishes a reading list twice a year at gatesnotes.com. He has said that the best investment he ever made was paying $100,000 to take Warren Buffett to dinner every year.

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.

Bill Gates

Gates's risk tolerance is intellectual and deliberate rather than impulsive. He takes genuinely large bets — TerraPower on nuclear fission, billions into climate technology, the Gates Foundation's campaigns to eradicate diseases that kill millions — but only after intense research.

His Think Weeks exist to force slow, rigorous thinking on big decisions. At Microsoft, he kept enough cash on hand to run the company for a full year with zero revenue because he never wanted short-term survival pressure to force a bad long-term decision.

That discipline carries into his personal finances.

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.

Bill Gates

He wakes up early, exercises on a treadmill while watching documentaries, and reportedly does the dishes every night. He has said dishes are meditative.

For a man worth $130 billion, the emphasis on routine is either deeply grounded or very good PR. He drove himself to work at Microsoft for years and lived in a normal house long after he could afford otherwise.

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.

Bill Gates

Microsoft Windows. The decision to license MS-DOS to IBM for the PC while retaining the right to sell it to other manufacturers was arguably the most lucrative business decision in tech history.

Every PC manufacturer then licensed Windows. Gates captured the entire PC market without building the hardware.

By 1999, Microsoft's market cap hit $616 billion.

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.

Bill Gates

Missing the internet. Microsoft was late and initially dismissive of the internet as a platform.

Gates eventually course-corrected and wrote the Internet Tidal Wave memo in 1995, redirecting the entire company toward internet strategy. But the delay allowed Netscape to establish footholds, and Microsoft's browser monopoly tactics led to the landmark antitrust case United States v.

Microsoft in 2000, which threatened to break up the company.

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.

Bill Gates

Bill Gates was born in Seattle in 1955. He taught himself to program on a PDP-10 at age 13.

He enrolled at Harvard in 1973, dropped out in 1975, and moved to Albuquerque with Paul Allen to found Microsoft. Their break came when they licensed an operating system to IBM for the original PC — and crucially, retained the rights to sell it to anyone else.

That decision made Microsoft. Windows became the standard operating system for the world.

Gates became the world's richest person in 1995 and held that title for much of the next 15 years. He transitioned out of Microsoft's day-to-day around 2000 and fully moved into philanthropy via the Gates Foundation.

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).

Bill Gates

Microsoft (co-founder, former CEO and chairman). Cascade Investment LLC (his personal investment vehicle).

Bill & Melinda Gates Foundation (co-chair). Major holdings through Cascade include Canadian National Railway, Deere & Company, and significant farmland.

Early Microsoft equity remains a massive portion of his net worth.

Naval Ravikant

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

Bill Gates

Harvard University — studied mathematics and computer science. Dropped out in 1975 after his sophomore year to found Microsoft.