Jack Bogle

Bogle''s investment philosophy is the simplest on this entire list: buy the whole market, hold it forever, pay as little as possible to do so, and never let a market downturn scare you into selling. He believed individual stock picking and market timing were exercises in humility — the market will humble you.

He also believed that the financial industry had a conflict of interest with its clients: the more complex and expensive the product, the better for the firm and the worse for the investor.

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.

Jack Bogle

Bogle''s core belief was that costs are the enemy of investors. Every dollar paid in management fees, transaction costs, and taxes is a dollar that does not compound.

Over 30 years, a 1% annual fee difference can reduce a portfolio by 25%. He called this the "tyranny of compounding costs." His secondary belief was behavioral: investors are their own worst enemy when they try to time the market or chase performance.

The solution to both problems is the same — buy a low-cost index fund, hold it indefinitely, and ignore the noise.

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.

Jack Bogle

Bogle was conservative by nature and by philosophy. His famous asset allocation rule — hold your age in bonds — is a rule of thumb for declining risk as you approach retirement.

He was deeply skeptical of leverage, alternatives, and complex products. He was also skeptical of ETFs (despite Vanguard offering them), arguing that the ease of trading them encouraged investors to behave badly — buying high, selling low — in ways that traditional mutual fund investors could not.

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.

Jack Bogle

Bogle was one of the most underpaid financial firm founders in history, by choice. Because Vanguard''s mutual structure does not enrich its leaders in the way that public companies do, Bogle ended up with approximately $80 million at his death — a fraction of what he would have been worth had Vanguard been structured like BlackRock or Fidelity.

He lived in a modest home in Pennsylvania. He drove ordinary cars.

He had a heart transplant in 1996 and continued working until shortly before his death in 2019 at age 89.

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.

Jack Bogle

The index fund itself is the win. The Vanguard 500 Index Fund, launched in 1976, inspired the passive investing revolution that has saved ordinary investors an estimated $1 trillion in fees compared to actively managed alternatives.

The structural insight — that you cannot consistently beat the market, so don''t try — was empirically verified over decades. By 2019, more money was invested in passive index funds than in active funds in the United States for the first time ever.

That shift is largely Bogle''s legacy.

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.

Jack Bogle

The Wellington merger with Thorndike, Doran, Paine & Lewis in 1966 was the admitted mistake of his career. He pushed for the merger to give Wellington growth stock exposure during the Go-Go era.

The combined firm underperformed badly in the bear market of 1973–1974. The board fired Bogle as CEO.

He has called the decision a serious error of judgment. The irony is that being fired is what created the circumstances for Vanguard.

The biggest professional failure of his life became the greatest gift to retail investors in history.

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.

Jack Bogle

Bogle grew up in New Jersey during the Great Depression, in a family that lost most of its money in the crash of 1929. His father struggled, the family moved repeatedly, and Bogle attended Blair Academy on a scholarship.

He won another scholarship to Princeton, where he studied economics and wrote a senior thesis on the mutual fund industry — a thesis that predicted that most actively managed funds would fail to beat the market over time. He was 22.

He was right.

He joined Wellington Management Company in 1951 and rose to CEO. He then made a disastrous decision in 1966, merging Wellington with the growth-focused Thorndike, Doran, Paine & Lewis — a merger that fell apart in the 1973-74 bear market and cost Bogle his job.

He was fired in 1974. In response, he filed to create a new kind of investment company — one owned by its own funds and therefore by its fund shareholders, not by outside investors.

Vanguard was born in 1975. The first index fund for retail investors launched in 1976.

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.

Jack Bogle

Vanguard is the company he built and the enduring legacy. Its mutual ownership structure — unusual in finance — means there are no outside shareholders taking profit.

The funds'' investors own Vanguard. This structure allows Vanguard to continuously lower its fees, because profit flows back to investors rather than to a corporate parent.

Today Vanguard manages over $8 trillion and is the largest issuer of mutual funds in the world.

The Vanguard 500 Index Fund (now VFIAX), launched in 1976, was the first retail index fund available to ordinary investors. It tracks the S&P 500.

It charges 0.04% annually. The average actively managed fund charges over 1%.

That difference, compounded over 30 years, is the difference between a comfortable retirement and a difficult one for millions of people.

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.

Jack Bogle

Blair Academy (scholarship), 1947. Princeton University, BA in Economics, 1951.

His Princeton thesis — arguing that mutual funds could not consistently outperform the market and should focus on cost reduction — was the intellectual seed of the index fund. He has said the thesis was one of the most important things he ever wrote, which is unusual praise for a 22-year-old''s college paper.

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.