If you still think of Tyler and Cameron Winklevoss as the "Facebook guys" who got left behind, you’re stuck in 2010. Honestly, most people are. The movie The Social Network did such a number on their public image—portraying them as these stiff, elite rowers who got outmaneuvered by a hoodie-wearing Mark Zuckerberg—that we've collectively missed one of the most insane pivots in financial history.
They aren't just the guys who sued for a $65 million settlement anymore. They are the guys who turned that settlement into billions by betting on things the rest of the world thought were a joke.
The 70,000 Bitcoin Bet
Back in 2013, the twins did something that made Wall Street laugh. They bought 1% of the entire supply of Bitcoin. At the time, the price was around $120. People thought it was magic internet money for drug dealers. Tyler and Cameron saw it as "Gold 2.0."
Today, that stash—estimated to be roughly 70,000 Bitcoin—is worth billions. And they haven't sold. While everyone else was day-trading and panicking during the various "crypto winters," they were building. They founded Gemini, which has become one of the few regulated, "grown-up" exchanges in the US. It’s funny because their whole brand is basically "the safe way to do crypto," which is the exact opposite of the wild-west vibe most of the industry has.
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Gemini Predictions and the Move Into Super Apps
Fast forward to late 2025 and early 2026. The twins just pulled off a major regulatory win that barely made the mainstream news but is kind of a big deal for anyone following the markets. Gemini launched Gemini Predictions across all 50 US states.
It took them five years to get the green light from the CFTC (Commodity Futures Trading Commission). Basically, they’re now letting people bet—excuse me, "trade event-based contracts"—on real-world outcomes. Whether Bitcoin hits $200k, or what happens in the next election. They're positioning Gemini to be more than just a place to buy Ether; they want it to be a "super app" that rivals Coinbase and Robinhood.
Why Zcash is the New Focus
Here’s the part that catches people off guard. Most crypto enthusiasts are obsessed with Bitcoin or Solana. The Winklevoss twins? They’ve started talking a lot about privacy. Recently, they backed a new firm called Cypherpunk, which is a crypto treasury company. They’ve already deployed over $50 million into Zcash.
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Why? Because they believe that as AI takes over everything, our data is going to be harvested like never before. They think privacy-first coins are the next big explosion. It’s a contrarian bet, which is exactly how they made their first billion.
Beyond the Screen: Real Bedford and Space
They aren't just sitting in glass offices in New York, either. It’s actually pretty wild—they co-own a football club in England called Real Bedford FC with podcaster Peter McCormack. It’s a Bitcoin-powered club. They’re literally trying to bring the "Orange Pill" to the UK's lower leagues.
Then there’s Winklevoss Capital. Their portfolio looks like a sci-fi novel:
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- Space Perspective: Carbon-neutral space travel.
- xAI: Yes, they're in on Elon Musk’s AI venture.
- Relativity Space: Printing 3D rockets.
What This Means for You
If you’re looking at Tyler and Cameron Winklevoss as a barometer for where the money is going, here is the takeaway. They don't play the short game. They are focused on three things right now: regulated prediction markets, privacy-preserving technology, and the "tokenization" of everything from stocks to real estate.
They’ve moved past the Facebook drama. They’ve moved past being "the rowers." They are effectively the architects of a very specific, regulated version of the future.
Practical Next Steps
- Audit your privacy: If you're interested in their "privacy" thesis, look into how much of your financial data is actually public.
- Explore Prediction Markets: Check out Gemini Predictions or competitors like Kalshi. They are often more accurate than news polls for forecasting events.
- The "Long-Term" Strategy: The twins' success didn't come from trading; it came from holding (HODLing). If you're in the market, ask yourself if your timeline is measured in weeks or decades.
The twins are betting that the future is private, regulated, and decentralized. Whether they're right again remains to be seen, but betting against them hasn't worked out well for most people over the last decade.