Shayne Coplan, the 28-year-old CEO of prediction market platform Polymarket, used company funds for private jet flights, apartment rent and other expenses, prompting Peter Thiel’s Founders Fund to demand repayment and tighter financial controls before making another investment, Bloomberg reported Tuesday.
At the time, Polymarket had no revenue. New York Stock Exchange parent Intercontinental Exchange (NYSE:ICE) has since invested $1.6 billion in the company, whose management practices have reportedly frustrated some of its biggest backers.
Coplan reimbursed the company, clearing the way for Founders Fund to invest at a $1.2 billion valuation.
Polymarket said the private jet flights were business-related and that Coplan disclosed the expenses proactively. The company said the repayment amounted to less than a software engineer’s annual salary.
Coplan initially took no salary and lived in a bedroom at Polymarket’s office, according to a company spokesperson.
ICE initially announced plans to invest up to $2 billion in Polymarket. It invested $1 billion in October 2025 and another $600 million in March, and now distributes the platform’s trading data to institutional investors.
Yet senior ICE executives have privately described difficulties mentoring Coplan, Bloomberg reported. Both ICE and Founders Fund recommended hiring a chief operating officer, but Coplan has not appointed one.
The investors also required a senior finance hire as part of their 2025 investments. Polymarket appointed its first chief financial officer in September.
Despite pressing for more discipline, Founders Fund reportedly structured its investment to ensure Coplan could not be fired without his consent.
Polymarket has since recruited executives from Goldman Sachs, DoorDash and Robinhood, while Alex Spiro, Elon Musk’s lawyer, joined its board and is helping with operations, according to Bloomberg.
“There were real growing pains, and I personally had to grow and change into what the company needed,” Coplan told Bloomberg.
Polymarket has fallen behind rival Kalshi in trading activity amid technical outages, regulatory scrutiny and a difficult US launch, according to Bloomberg.
Even so, Polymarket is reportedly raising money at a $21 billion valuation, more than double its $9 billion valuation when ICE invested in 2025. 1789 Capital, where Donald Trump Jr. is a partner, is leading the round, with Founders Fund also participating.
Benzinga previously covered Coplan’s management troubles as Kalshi took the lead in trading volume. Kalshi is now reportedly seeking a valuation roughly twice Polymarket’s.
Polymarket did not immediately respond to Benzinga’s request for additional comment.
Kalshi and Benzinga have an existing data collaboration agreement.
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