i3Soft founder says online poker forgot its casual players—and now they want to win them back

John Caldwell's path to building poker software ran through the A&R department at Atlantic Records, a near-fatal health scare at 28, and four-and-a-half years running a vanity label for Hootie and the Blowfish. When the music business collapsed around Napster and file sharing, he found himself playing poker, frustrated by the lack of good information online—and accidentally stumbled into the job that would define the next chapter of his career.

A hungover morning after the MTV awards brought a phone call from a 372 area code. Tony Guoga (better known as Tony G) was on the other end, asking if he was the guy who wrote the poker section of Las Vegas for Dummies. That led Caldwell to PokerNews, which he helped grow from three people to 70 as CEO, and eventually to PokerStars, where he managed the brand's roster of endorsers and worked on televised products like The Big Game. He left the day the founders did.

Since then, he's been building software for the gambling industry. His current company, i3Soft, launched its flagship poker product just three weeks before this conversation—the culmination of a four-year development cycle that included a 15-month false start with a third-party software provider before a full team reset in May 2024.

The problem i3Soft is trying to solve is one Caldwell says he watched develop in real time. "I really felt like there was a world where we could bring the recs back," he said. "The experience for recreational players at this point is awful." His diagnosis: online poker tournaments take too long and casual players can't win anymore. The two issues compound each other. Without recreational players putting money in at the bottom of the funnel, the ecosystem dries up.

i3Soft's answer is a two-part product suite. The first is Skip It, a multi-table tournament format that compresses what would normally be a 12-to-14-hour online tournament into about two and a half hours by using AI to play players through the early stages—so by the time a user actually touches cards, the field has thinned and the remaining play is skill-based. The second is Poker Casino, a suite of casino games built specifically to ease poker players into casino products rather than pointing them at slots and hoping for the best. "Casinos are like, hey Mr. Poker player, come try Big Bass Bonanza," Caldwell said. "The poker players are like, F you. I just don’t personally think that’s effective. "

The B2B go-to-market pitch is that casinos can now offer poker tournaments with real liquidity (historically the hardest part of running poker) as a plug-and-play iframe with no customer service or fraud overhead required. Commercial conversations, Caldwell said, have accelerated sharply in the last 90 days compared to the prior year.

One lesson from his PokerStars days informs everything: "Poker Twitter" is not poker. Survey after survey at PokerStars showed that the debates dominating online poker discourse (HUDs, software tools, competitive formats) were things the majority of the actual player base didn't care about. The people who matter are the ones who show up in the poker room with a screen name nobody recognizes. Getting more of them back online is the whole point.

His targets for 2026: five casino clients running Skip It under the shared liquidity model, and 25 installs of Poker Casino. If those land, he says, everything else follows.

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