Polymarket CEO Shayne Coplan is regularly late to private meetings, attended at least one of them barefoot and is “easily distracted,” texting and taking phone calls mid-conversation, according to a Bloomberg report.

The quirks would read as startup color if the company weren’t bleeding its lead to rival Kalshi eight days before its biggest backer reports earnings.

Intercontinental Exchange (NYSE:ICE), the parent of the NYSE, has committed up to $2 billion to Polymarket at escalating valuations.

It reports Q1 earnings on April 30, with the consensus analyst target at roughly $194 on a Strong Buy rating. Raymond James raised its target to $222 earlier this month.

Kalshi Pulls Ahead

The two companies’ valuations moved in lockstep for most of the past year. That changed last month, when Kalshi raised $1 billion at a $22 billion valuation led by Coatue Management.

Polymarket is reportedly weighing a raise at $15 billion, a gap of roughly $7 billion.

Kalshi’s year-to-date notional volume has also pulled ahead, at $37.5 billion versus Polymarket’s $29.2 billion.

Citizens analyst Jordan Bender told Bloomberg Polymarket’s plan “was to have product parity with Kalshi by the Super Bowl.” It didn’t happen. The US app remains in beta with March volumes on the test version coming in around $256 million against Kalshi’s $13.07 billion.

Bloomberg reports the hold-up is structural. Polymarket’s international exchange runs on crypto rails, creating engineering challenges its US-first competitors didn’t face.

Pop-Up Problems, Scheduled Downtime

A recent fee rollout was botched enough that an employee admitted on Discord “the rollout was terrible.” The company added that it was “adding way more checks before anything like this can be pushed out in the future.”

The operational stumbles have piled up elsewhere. Polymarket’s Washington pop-up bar drew negative coverage for technical snafus during its opening. An earlier pop-up grocery store also opened late.

On Monday, a scheduled five-minute exchange restart turned into an outage of more than an hour.

ICE CEO Jeff Sprecher called Coplan a “genius” and said he has urged him to move faster.

“You’re not going to be a prime time company unless you can access the US legally,” he recalls telling Coplan. On his $2 billion bet, Sprecher was blunt. “My Polymarket on these things is either a complete wipeout or they are going to be home runs.”

Polymarket did not immediately respond to a request for comment from Benzinga.

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