Elon Musk

Musk does not invest in the traditional sense. He builds companies and holds them.

His strategy is to find industries where he believes the incumbent players are too slow, too cautious, or fundamentally wrong in their assumptions — and then attack from first principles. He has said he asks "what is the physics limit?" of any problem, not what the industry standard is.

He holds massive concentrated equity in each of his companies. He does not diversify.

He famously said he was "asset rich and cash poor" and at times has literally borrowed money against his Tesla stock to fund other ventures.

Arianna Simpson

Simpson invests in crypto the way a founder would, not a spreadsheet jockey. She hunts for the technology that developers actually want to build on.

Then she bets big and holds through the wild swings. She is comfortable being early.

She is comfortable looking wrong for a while. As she puts it, the job is to follow where the best entrepreneurs are already going, not to sit in a room and decide what should be interesting.

In plain English, she buys the picks and shovels of crypto and waits years.

Elon Musk

Build things that matter. He has said he did not start companies to make money — he started them because electric vehicles and space were the most important problems he could work on.

He believes the only way to understand if something is possible is to try it. His financial philosophy is: do not optimize for personal comfort, optimize for impact.

He will borrow against his assets, take massive personal financial risk, and maintain concentrated positions that would terrify any normal financial advisor.

Arianna Simpson

Simpson's core belief is that crypto matters most where money is broken. She points back to Zimbabwe.

When your currency loses value by the hour, a network no government controls stops being a toy and becomes a lifeline. She bets on that idea over decades, not quarters.

She also backs builders over hype. The projects that survive are the ones developers keep showing up to work on, bull market or bear market.

Her best investments, she says, are the ones where the founder's thinking is further ahead than her own.

Elon Musk

Musk borrowed against his Tesla stock to buy Twitter. He sold Tesla shares to fund SpaceX.

In 2008, with both Tesla and SpaceX weeks from bankruptcy, he split his last $40 million between them because he had already decided that if they died, he'd be broke — and that was fine. He told his biographer he did not fear losing everything.

What he feared was not trying. His pain threshold for financial loss is essentially unlimited, which makes him either the most courageous or the most reckless operator in modern business history, depending on which week you ask.

Arianna Simpson

Simpson is built for crypto's stomach-churning drops. She thinks in decades, not weeks, so an 80% crash reads as noise rather than an emergency.

She proved it the hard way. Autonomous Partners was investing right as the 2018 crypto winter hit, and she kept going.

Her funds are designed to be 10-year-plus funds on purpose. The whole point is to hold long enough that short-term panic stops mattering.

Elon Musk

For years, Musk did not own a house. He sold all his California properties and reportedly lived in a small modular home near SpaceX's facilities in South Texas.

He drives a Tesla. He is known for working extreme hours — there are accounts of him sleeping on factory floors during Tesla production crises.

He has said he does not spend much time thinking about his net worth and that money is only useful as a resource to accelerate his missions.

Arianna Simpson

Simpson keeps her personal life almost entirely offline, which is rare for someone this visible in crypto. What is public is how she handles the asset itself.

She is a holder, not a day trader. She has said the firm's funds are built to run for a decade or more, and she invests her attention the same way.

For someone whose whole job is digital assets, she treats them less like a casino and more like seeds planted for a long harvest.

Elon Musk

Tesla. He invested his own money when it was burning cash and nearly bankrupt, held through multiple near-death experiences, and watched it grow from a startup nobody believed in to a $1 trillion market cap company.

He also holds SpaceX equity. SpaceX went public in June 2026 at a valuation north of $1.7 trillion, having rewritten the economics of space launch.

Arianna Simpson

Phantom. Simpson got in early on the crypto wallet, and a16z crypto backed it when it was a small team building on Solana.

Phantom raised $150 million in January 2025 at a $3 billion valuation. Her other headline deal was a wild ride.

She led the $152 million round in Sky Mavis, the maker of Axie Infinity, in October 2021 and joined its board. Months later the game's Ronin bridge was hacked for about $600 million and the token collapsed.

Phantom is the win. Axie is the reminder that crypto giveth and taketh away.

Elon Musk

Twitter / X. He paid $44 billion for it in 2022, considered overpaying dramatically.

The company lost most of its advertising revenue after Musk's takeover. Advertisers pulled out.

He feuded publicly with brands, journalists, and regulators. By most financial metrics, it was an expensive and chaotic acquisition.

His stated defense is that X is a long-term platform for free speech and AI training data.

Arianna Simpson

Timing. Autonomous Partners launched in late 2017, right at the peak of the crypto mania.

Within months the market fell off a cliff. Bitcoin dropped from nearly $20,000 to around $3,000 by the end of 2018.

Being early is one thing. Being early and then watching the entire market crater tests everyone.

The rough entry taught her a lesson she now lives by. Conviction only pays if you can survive long enough to be proven right.

Elon Musk

Elon Musk was born in Pretoria, South Africa in 1971. He taught himself to code, sold a video game called Blastar at age 12 for $500, then moved to Canada at 17 to avoid mandatory South African military service.

He transferred to the University of Pennsylvania, sold Zip2 (a web software company) to Compaq for $307 million in 1999, then founded X.com — which became PayPal — and sold it to eBay for $1.5 billion in 2002. He plowed essentially all of it into SpaceX and Tesla simultaneously, nearly went bankrupt in 2008, and then watched both companies become dominant.

Tesla became the most valuable car company on earth. SpaceX became the dominant commercial launch provider.

He bought Twitter for $44 billion in 2022, renamed it X, fired most of the staff, and called it a platform for free speech. He became the world's richest person multiple times over.

Arianna Simpson

Simpson grew up in Milan and studied international politics at Penn State. Her turning point came in Zimbabwe in 2013.

She saw firsthand what happens when a currency loses value by the hour. That got her hooked on the idea of money no government can print at will.

She quit her job at Facebook and joined BitGo, a company that guards crypto for big institutions. In 2015 she helped start Crystal Towers Capital, backing young Y Combinator startups.

In 2017 she launched her own crypto fund, Autonomous Partners. She raised it from serious names, including Coinbase CEO Brian Armstrong and David Sacks' Craft Ventures.

In 2020 she joined a16z crypto as a deal partner and was later made a general partner.

Elon Musk

Tesla (CEO). SpaceX (CEO and chief engineer).

X / Twitter (owner and executive chairman). xAI (founder).

Neuralink (co-founder). The Boring Company (founder).

Early investor in DeepMind (sold stake). Previously: Zip2 (sold 1999), PayPal / X.com (sold 2002).

Arianna Simpson

Autonomous Partners was her own show. She started it in 2017 and used it to back crypto projects like Talos, a trading platform, and Mythical Games, a blockchain gaming studio.

At a16z crypto she now helps run one of the largest crypto funds on earth, more than $7 billion across several funds. Her best-known bets there are Phantom, the crypto wallet, and Blackbird, the dining rewards startup from Resy co-founder Ben Leventhal.

She also sits on the board of Sky Mavis, the company behind Axie Infinity. Before all of this she worked at BitGo and Facebook.

Elon Musk

University of Pennsylvania — dual bachelor's degrees in economics (Wharton) and physics. Started a PhD in energy physics at Stanford, dropped out after two days to start Zip2.

Arianna Simpson

Simpson went to Penn State, in the Schreyer Honors College. She earned dual degrees in international politics and Spanish.

Not a computer science degree. Not an MBA.

Her real education in money came later, on the ground in Zimbabwe in 2013, watching inflation do its damage in real time.