His name was Freeman. Christopher Freeman. And in the end, he was exactly that โ€” free. Free from paperwork. Free from lawyers. Free from contracts. Free from his Stake.com founder equity. Truly, genuinely, spectacularly free.

We did not plan this observation. The universe did.

Let's be clear about something. Chris Freeman did not lose $400 million in cash. You cannot lose something you never had. What Chris Freeman did was something far more impressive: he watched his stake in what became a $14+ billion company walk out the door, waved goodbye, and then six years later hired a lawyer to sue for $400 million. [CryptoSlate]

It could not come back. But we're getting ahead of ourselves.

The year is 2013. Freeman โ€” a young, presumably normal man from Connecticut โ€” calls up his childhood friend Bijan Tehrani and says, essentially: let's build a Bitcoin dice game. [Yogonet] This is, objectively, a visionary idea. Bitcoin is worth approximately nothing. Online gambling is the Wild West. Nobody is doing this. Freeman saw the future. Freeman was right.

"Some people see the world as it is. Chris Freeman saw the world as it should be โ€” where friends don't steal from friends and a handshake means something."

โ€” Bent Over Club Editorial Board ยท Miami, FL
Key Facts

Chris Freeman claims he was cheated out of a $400 million equity stake in Stake.com by co-founder Ed Craven. The alleged deal was a handshake โ€” never in writing. Freeman is now Founding Member #001 of the Bent Over Club.

  • Alleged deal: 50/50 partnership between Freeman and Craven at Stake.com's founding
  • The problem: no written contract โ€” handshake only
  • Craven's outcome: Stake.com became a multibillion-dollar crypto casino; Craven bought an $80M Melbourne mansion
  • Freeman's outcome: $0 equity, $400M lawsuit, refused to fly to Australia for court

In his defense: Australia is very far away

In 2016, Tehrani and Craven told Freeman the new project would be a fiat casino. Freeman, committed to crypto, stayed in Connecticut. [GamblingNews/SMH] Melbourne is literally on the other side of the planet. The flights are 24 hours. The spiders are the size of your hand.

The fact that Tehrani and Craven then built a crypto casino โ€” exactly what Freeman had always wanted โ€” is, legally speaking, deeply ironic.

2013
Freeman's idea. Bitcoin dice game. Visionary. Primedice is born.
2014
His stake drops from 20% to 14%. "To reward other developers." Freeman nods. No paperwork. Vibes only.
2016
"The new casino will be fiat." Freeman believes them. Does not move to Australia. Connecticut is nice this time of year.
2017
Stake.com launches. As a crypto casino. With a dice game. Freeman watches from Connecticut. His account is later blocked.
2022
Freeman sues for $400M. [SDNY Court Filing] No contracts. No emails. No paper trail. Just vibes and a very expensive lawyer.
2024
Freeman voluntarily dismisses the lawsuit. [UniCourt Docket #63] Receives $0. Craven buys an $80M house in Melbourne.

In his defense: lawyers are expensive

The problem was not the allegations. The problem was the evidence. Or more specifically, the complete and total absence of any written evidence whatsoever. No contracts. No emails. No paper trail. Just memory.

Courts, it turns out, are not particularly moved by memory.

"He didn't lose $400 million. He invested his founder equity in the belief that people are fundamentally decent. The ROI was negative. The lesson was expensive."

โ€” Bent Over Club Financial Analysis Desk

In his defense: Craven bought an $80M house

Ed Craven recently purchased a home in Melbourne for $80 million Australian dollars. This broke the city's residential price record.

Freeman's 14% stake in Stake.com would today be worth between $2 and $3 billion based on Stake's estimated 2025 valuation of $14-23 billion. Which is roughly 25-38 of Craven's Toorak mansions. [Bitcoinist] Or one very large house with a lawyer on retainer.

The Bent Over Club Verdict

Chris Freeman was not stupid. He was idealistic. He believed in friendship, handshakes, and the fundamental decency of people he'd known since childhood. In a better world, he would be a billionaire. In this world, he is a founding member of the Bent Over Club โ€” and honestly, the membership suits him.

Lessons from the club
01 A handshake is worth exactly as much as the paper it's not written on.
02 When your partners say "fiat casino" and then build a crypto casino โ€” that's called a clue.
03 Australia is far. Billion-dollar equity is farther. Do the math before you book the flight you don't take.
04 A lawyer costs $500/hour. A lack of lawyer cost Freeman a $400 million lawsuit and billions in equity. The hourly math is straightforward.
05 If your childhood friend buys an $80M house after you leave the company โ€” it was not a fiat casino.
๐ŸŠ
Sonny Jr. Esq. ยท Attorney at Law ยท Miami Beach

"Always get it in writing. Even if he's your best friend. Especially if he's your best friend."

Golden Advice #001 ยท Freeman Edition ยท Est. 2026