True Stories of Diamond Hands

Sir John Hargrave
4 min readFeb 7, 2024


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I enjoyed the film Dumb Money, which just came to Netflix. It tells the real-life story of Keith Gill, a.k.a. “Roaring Kitty” on Reddit, who led millions of ordinary investors to power the GameStop short squeeze in 2021, bringing down the mighty Melvin Capital hedge fund.

The tension in the film comes from all the average-Joe investors — and Gill himself — watching their net worth soar as $GME prices catapult in value. Their friends and family beg them to cash out, and you can feel how difficult it is for them to HODL.

The portrayal of Gill, played by Paul Dano, is surprisingly sweet and vulnerable. He’s not a “bro,” but a family guy who is suffering the same internal conflict as everyone else — along with his longsuffering wife, played by Shailene Woodley.

It’s a great investing story, because it shows the power of believing in your investments, even when the rest of the world says you’re crazy.

(I’m no fan of $GME — I feel the same way about meme stocks that I do about meme coins — but I do appreciate the comedy of the sad and struggling GameStop being the stock that drove everyone wild. It was crazy.)

It got me thinking about other legendary investors who held when everyone else said they were nuts. Here are a few stories of history’s greatest “diamond hands.”

John Doerr and the E-Commerce Play

In 1995, a visionary venture capitalist at Kleiner Perkins saw a young company with potential. It was just a weird-looking guy selling books online, with his wife. Defying fierce internal resistance, Doerr led an $8 million funding round to back the guy’s vision.

The company had many ups and downs, but Doerr kept his conviction, even during the dot-com crash in 2000, which wiped out much of the young company’s value and soured the public on e-commerce. The company had to cut costs and reported zero profits for nearly a decade.

Doerr’s diamond hands eventually paid off: he helped fund

Read: The Everything Store by Brad Stone

The Animator and the Film

After the failure of his first animation studio, a young creative faced incredible financial hardship. He had done a deal with a fly-by-night company that left him unpaid for work completed. He was disillusioned, deeply in debt, and digging through dumpsters for dinner.

Undeterred, he created a new studio with his brother, and after a series of successful animated shorts, secured funding for his first feature-length animated film. There was incredible resistance to the idea, but he went all in, even mortgaging his house and relying on friends.

The film, “Snow White and the Seven Dwarves,” was a critical and commercial smash, and the rest is Disney history.

Watch: Walt Before Mickey on Amazon Prime

The Old Man and the Crisis

During the 2008 financial crisis, everyone was panic selling, but one old man remained calm in the hurricane. He even declared it a “buying opportunity,” and increased his investments in targeted companies.

He bought more Goldman Sachs, even while investors were fleeing financial stocks. He bought more Wells Fargo and Bank of America, even while their collapse seemed imminent. His belief was simple: these companies were not failing, they were now “on sale.”

It was one of the most gangsta moves in investing history, and that is why Warren Buffett is an OG.

Read: The Snowball: Warren Buffett and the Business of Life by Alice Schroeder

The Tech Exec and the Turnaround

After building his hobbyist computer company to a successful technology firm, the young founder was squeezed out of the company in a humiliating way by his board. He started another computer company that kind of languished, and everyone thought he was done.

Meanwhile, the new CEO ran his original company into the ground, and the board begged for his return. The tech exec came back, and immediately fired the board, installing a new one and saving the company from a near-death experience.

Today, Apple is the most valuable company in the world, and Steve Jobs deserves much of the credit.

Read: Steve Jobs by Walter Isaacson

The Programmer and the Stash

In 2008, a programmer proposed a new kind of digital money. He released a white paper explaining how it worked, discussed and debated it in online forums, then built it himself. Then he disappeared.

If you’re pondering whether to sell your digital investments, remember that Satoshi Nakamoto still owns wallets containing between 25 to 50 billion dollars.

Stay strong, diamond hands.

Read: The Book of Satoshi by Phil Champagne

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Sir John Hargrave

CEO of Media Shower. Publisher of Bitcoin Market Journal. Author of Mind Hacking. Making things better.