Backers of Polymarket have pressed founder and CEO Shayne Coplan to tighten the company’s finances and hand off more of its day-to-day management, Bloomberg reported on Tuesday, citing people familiar with the matter. The report lands as the prediction market raises new money while trailing rival Kalshi in trading volume.

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Spending Before the 2025 Round

According to people familiar with the negotiations, Founders Fund, the venture firm cofounded by Peter Thiel, learned during its 2025 due diligence that Coplan had charged private jet trips, his apartment rent and other personal costs to the company, at a time when Polymarket had no revenue. Those people said the firm would not invest until Coplan paid the money back and kept up efforts to strengthen financial controls. He repaid it, and Founders Fund went on to invest at a $1.2 billion valuation, Bloomberg reported.

A Polymarket spokesperson was quoted by Bloomberg as saying the flights were business travel, that Coplan “proactively” disclosed the costs, and that the repayment amounted to “less than a software engineer’s annual salary.” Haseeb Qureshi, managing partner at Dragonfly, an earlier investor, reportedly told Bloomberg there was “obviously zero bad intent.” Polymarket didn’t immediately respond to a request for comment from Unchained.

Calls for a COO

Senior staff at Intercontinental Exchange, the NYSE owner and a major Polymarket shareholder, have privately said Coplan has been hard to mentor, Bloomberg also reported, citing people with knowledge of the matter. ICE and Founders Fund have reportedly both recommended that he hire a chief operating officer, which he has not yet done. Separately, the National Futures Association threatened to drop Polymarket as a client over its record keeping, Bloomberg reported, citing people familiar with the situation; one reportedly said the issue has been fixed.

Polymarket hired its first chief financial officer in September, a step one person reportedly told Bloomberg Founders Fund and ICE required in their 2025 deals. Alex Spiro, Elon Musk’s personal lawyer, now sits on Polymarket’s four-member board and helps run daily operations, including hiring, people familiar with his role reportedly told Bloomberg.

“There were real growing pains, and I personally had to grow and change into what the company needed,” Coplan was quoted as saying in a statement to Bloomberg.

A $21 Billion Raise

The Bloomberg report comes as 1789 Capital, the firm where Donald Trump Jr. is a partner, is reportedly leading Polymarket’s new raise, which values the company at $21 billion. The new price tag more than doubles the $9 billion valuation from ICE’s 2025 investment, though it is roughly half of what Kalshi is reportedly seeking in its own current raise.

Polymarket also faces a CFTC investigation that Bloomberg reported earlier this year, after the Justice Department closed an earlier probe without charges in 2025.

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