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.

Scott Galloway

Galloway's personal investing style is relatively conservative given how loud he is. He keeps a heavy allocation in index funds and real estate.

He does make concentrated bets on individual stocks when he has conviction — he famously held Amazon for years. He angel invests occasionally but is not prolific.

His real wealth comes from business exits and media income, not portfolio management.

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.

Scott Galloway

Diversify, own assets, and do not confuse being smart with being lucky. Galloway preaches that the most reliable path to wealth is boring — buy index funds, own property in growing cities, and let time do the work.

He is deeply skeptical of anyone who claims they can consistently beat the market.

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. He went deep on crypto early, co-founding MetaStable Capital in 2014, years before most investors took it seriously.

He has argued that in early-stage investing, returns are so concentrated in outliers that you want maximum exposure to them.

Scott Galloway

Moderate. Galloway has experienced the full spectrum — he had a company go public and then go bankrupt (Red Envelope), which taught him that financial ruin is always closer than you think.

Post-L2 sale, he became much more conservative. Heavy real estate holdings in New York and Florida.

He preaches diversification publicly and mostly follows his own advice, with occasional concentrated stock positions.

Naval Ravikant

Naval has spoken extensively about meditation and about protecting his mornings for thinking. He avoids a packed calendar.

He reads constantly, physics, philosophy and evolution, not just business books. He rejects hustle culture and argues for working deeply on a few things.

Scott Galloway

Galloway owns significant real estate in New York and Florida. He talks openly about his wealth and spending — nice apartments, good restaurants, private school for his kids.

He is not frugal and does not pretend to be. But he is very intentional about where money goes.

He has said his biggest financial luxury is "buying back his time" — paying for convenience so he can focus on what matters.

Naval Ravikant

His early bets through The Hit Forge, a $20 million fund he started in 2007. It backed Twitter when it was a chaotic startup with no business model.

Twitter went public in 2013 at about a $14 billion valuation and Elon Musk later bought it for $44 billion. The same fund got into Uber very early, before it became the most valuable private startup of its era.

He also backed Notion when it was a tiny seed-stage company.

Scott Galloway

Selling L2 to Gartner for an estimated $134 million in 2017. He built L2 into the go-to benchmarking firm for digital competence of luxury and consumer brands.

The exit, combined with his media career taking off simultaneously, catapulted him from "NYU professor" to "famous rich guy who yells about tech on the internet."

Naval Ravikant

The Epinions exit. When Epinions merged into Shopping.com, the founders' common stock was worth next to nothing, even though Shopping.com went public in 2004 and was bought by eBay in 2005.

Naval felt he and the other founders had been misled about what their shares were worth. In 2005 he and three co-founders sued Benchmark Capital, August Capital and fellow co-founder Nirav Tolia.

The case settled, but it burned relationships with some of the most powerful VCs in Silicon Valley. The lesson stuck with him: know exactly what your equity is worth and who controls it.

Scott Galloway

Red Envelope. Full stop.

Galloway has been brutally honest about this — he took a gift e-commerce company public, it was valued at hundreds of millions, and then it went bankrupt. He has called it the most painful experience of his career and has said it took years to emotionally recover.

He lost a significant amount of personal wealth in the collapse.

Naval Ravikant

Naval Ravikant was born in New Delhi and moved to New York at age 9. He went to Stuyvesant High School and then Dartmouth.

He co-founded Epinions in 1999, a consumer review site that raised $45 million and merged with DealTime in 2003 to form Shopping.com. That merger ended in a lawsuit.

In 2005 Naval and three co-founders sued Benchmark Capital, August Capital and co-founder Nirav Tolia, saying they had been misled about the value of their stock. It settled later that year.

He then co-founded Vast.com, an online marketplace. In 2007 he started The Hit Forge, a small fund that backed Twitter, Uber and Stack Overflow early, and co-wrote the Venture Hacks blog on term sheets.

That blog turned into AngelList in 2010, a platform that let accredited investors back startups alongside top angels. AngelList also owns Product Hunt and raised money at a $4 billion valuation in 2022.

He also co-founded the crypto fund MetaStable Capital in 2014 and the voice app Airchat in 2023.

Scott Galloway

Scott Galloway is a serial entrepreneur and NYU Stern School of Business professor who became famous for his brutally honest takes on Big Tech. He founded nine companies over his career, including L2 (a business intelligence firm sold to Gartner in 2017), Red Envelope (an e-commerce company that went public then bankrupt), and Prophet (a brand strategy firm).

His 2017 book The Four, about Amazon, Apple, Facebook, and Google, became a bestseller. His YouTube channel and Prof G podcast reach millions.

He called Amazon buying Whole Foods before it happened. He also co-hosts Pivot with Kara Swisher, one of the most popular tech podcasts in the world.

He teaches brand strategy at NYU and is known for his profanity-laced, data-heavy lectures that go viral every semester.

Naval Ravikant

AngelList (co-founder, 2010, now chairman). Epinions (co-founder, 1999, merged into Shopping.com).

Vast.com (co-founder). The Hit Forge (a $20 million early-stage fund, 2007).

Venture Hacks (blog, 2007, the seed of AngelList). MetaStable Capital (crypto hedge fund, co-founder, 2014).

Spearhead (fund that gives founders money to angel invest, 2017). Airchat (voice social app, co-founder, 2023).

Angel investments include Twitter, Uber, Postmates, Stack Overflow, Notion, Foursquare and Yammer, among hundreds of others.

Scott Galloway

L2 Inc (founder, sold to Gartner), Red Envelope (founder, IPO then bankruptcy), Prophet (co-founder), Section4 (founder, online education), Prof G Media (founder)

Naval Ravikant

Stuyvesant High School in New York (1991). Dartmouth College — degree in computer science and economics, 1995.

Scott Galloway

UCLA (BA), UC Berkeley Haas School of Business (MBA).