NEW YORK, May 14, 2026, 19:07 (EDT)
Gemini Space Station Inc. on Thursday said Winklevoss Capital Fund poured in a $100 million bitcoin-backed investment, bolstering the crypto exchange just as it trimmed its first-quarter loss and leaned deeper into the world of prediction markets. According to a regulatory filing, the deal was finalized that same day.
It’s all about timing. Shares of Gemini finished Thursday at $5.26, a far cry from the $28 price set during its IPO in September. Then, following the latest announcement, the stock jumped roughly 15% in after-hours trading, according to Bloomberg.
Gemini is working to reposition GEMI stock following a rough patch. Back in March, shareholders filed suit, claiming the company failed to fully disclose its move toward prediction markets. Previous announcements about layoffs and pulling out of certain markets had already knocked shares under $7, according to Reuters.
Winklevoss Capital Fund picked up 7,142,857 Class A shares at $14 apiece, paying with roughly 1,258 bitcoin, according to the filing. The fund, run by Cameron and Tyler Winklevoss—president and CEO—already holds the largest stake in Gemini.
Gemini posted $50.3 million in revenue for the first quarter, marking a 42% jump year-over-year. Net loss shrank to $109.0 million from $149.3 million. Still, operating expenses surged 73%, reaching $144.5 million.
The core exchange continued to underperform. Revenue there slid 27% to $17.2 million, with total trading volumes cut in half to $6.3 billion compared with $13.5 billion the previous year. Over-the-counter revenue, which covers large trades made directly with clients, jumped to $6.3 million from just $0.1 million.
Prediction markets, a recent addition, involve contracts based on outcomes of future events—think elections or sports, not typical earnings or commodity moves. Gemini reported $0.4 million in revenue for the segment in its first complete quarter, with a user base of roughly 20,000.
Tyler Winklevoss argued the market was “significantly undervalued Gemini.” His twin, Cameron Winklevoss, called the company’s April derivatives clearing organization license a “major milestone” for efforts to build out a marketplace covering predictions, futures, and options. GlobeNewswire
The license is significant—it allows Gemini Olympus to clear fully collateralized futures, options on futures, and swaps, pushing the firm further toward a fully regulated, end-to-end trading stack. On the CFTC’s DCO roster, you’ll also find Kalshi Klear and Polymarket Clearing, both closely watched in the wider prediction-market space.
Still, the legal landscape remains murky. In April, New York’s attorney general took Coinbase Financial Markets and Gemini Titan to court, alleging their prediction markets ran afoul of state gambling laws. Coinbase pushed back, calling for federal regulation. Gemini, for its part, stayed silent.
The warning signs aren’t hard to spot: Gemini’s expenses keep outpacing its revenue, trading activity on its core exchange dropped off a cliff, and now the company is betting on a segment regulators at both state and federal levels remain locked in dispute over. Back in February, Truist’s Matthew Coad summed it up bluntly—management needed to shift focus from clawing back market share to just “staying afloat during a crypto downturn.” Reuters
Management is set to talk through the quarter on a Friday call at 8:30 a.m. ET. This time, investors aren’t just after standard “markets company” commentary—they’re focused on what exactly the $100 million brings: more runway, actual product expansion, or maybe just a shot at profitability. GlobeNewswire
