Jeff Bezos

Bezos's investment style is long-term and patient to an extreme degree. He built Amazon by deliberately losing money for years, reinvesting every dollar into infrastructure, logistics, and new businesses.

He told shareholders repeatedly that he would sacrifice short-term profitability for long-term market position. AWS was not a profit center for years — then it became Amazon's most profitable business unit.

He put $250,000 into Google personally in 1998, six years before its IPO, and that one cheque alone was worth hundreds of millions by 2004. Bezos Expeditions, his personal investment vehicle, came later and backed Airbnb, Uber and Twitter.

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.

Jeff Bezos

His core philosophy is customer obsession combined with long-term thinking. He says most companies optimize for the next quarter.

He optimizes for the next decade. He invented the concept of "working backwards" — writing the press release and FAQ for a product before building it, to ensure the team starts from the customer's perspective.

He also invented the "two-pizza rule": if a team needs more than two pizzas to feed, it is too big.

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.

Jeff Bezos

Bezos told shareholders in 1999 that Amazon would lose money for years. He said the same in 2001.

He meant it. His risk tolerance comes from a framework he calls the "regret minimization framework" — imagining himself at 80 looking back — which weights the risk of not trying far more than the risk of failing.

The risk he manages carefully is existential: through all of Amazon's early loss years, he kept debt manageable and liquidity intact so that survival was never in question. He takes huge bets on the thesis, but he protects the foundation.

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.

Jeff Bezos

Bezos lived frugally in the early Amazon years — he famously built his own desk from a door laid on sawhorses to keep costs down. The "door desk" became a symbol at Amazon.

He became extraordinarily wealthy but for years retained a modest personal style. Post-divorce and especially post-CEO, he moved to Miami, bought massive properties, and began a much more public lifestyle with Lauren Sanchez, whom he married in June 2025.

He exercises in the morning before checking his phone.

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.

Jeff Bezos

Amazon Web Services. AWS was an internal tool that Amazon began selling to external companies in 2006.

By 2023, AWS generated $91 billion in revenue and accounted for the majority of Amazon's operating profit. It is the dominant cloud computing platform in the world — Microsoft and Google are still playing catch-up.

Bezos had the idea when Amazon was already a massive retailer. He added an entirely different trillion-dollar business on top.

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.

Jeff Bezos

The Washington Post acquisition is the most common answer. He paid $250 million for it in 2013 and has poured money into it since.

The Post has struggled commercially and faces the same headwinds as all legacy print media. Separately, his rocket company Blue Origin has consistently lagged SpaceX in capability and ambition — Blue Origin's New Shepard is basically a tourist ride compared to SpaceX's reusable orbital rockets.

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.

Jeff Bezos

Jeff Bezos graduated from Princeton in 1986, worked at several finance firms, and became the youngest-ever senior vice president at D.E. Shaw hedge fund by age 30.

In 1994, he quit to drive cross-country with his then-wife MacKenzie, writing the Amazon business plan in the passenger seat. He started selling books from his Bellevue garage, moved operations to Seattle, and launched Amazon.com in 1995.

What followed is one of the greatest compounding business stories in history: books to everything, retail to cloud computing (AWS), a logistics network that rivals national postal services. Amazon's revenue in 2023 was $574 billion.

Bezos stepped down as CEO in 2021 to focus on Blue Origin, his space company. He also owns The Washington Post (acquired 2013 for $250 million).

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.

Jeff Bezos

Amazon (founder, executive chairman). Blue Origin (founder).

The Washington Post (owner). Bezos Expeditions (personal investment vehicle — early backer of Google, Airbnb, Twitter, Uber, and many others).

Previously: D.E. Shaw (SVP).

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.

Jeff Bezos

Princeton University — Bachelor of Science in electrical engineering and computer science, summa cum laude, 1986.

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.