Nobody tells you that buying a sportsbook out of bankruptcy is essentially a parlay.
Not a two-teamer. A six-leg ticket — three regulatory approvals, three market access agreements — where every leg has to hit, the timing has to align, and one extended review can hold up the whole payout. I know this because I just lived it. And I’m writing this not to complain about the process, but because I think the industry deserves an honest account of what it actually looks like from the inside.
The conversation nobody writes about
Before there were lawyers, asset schedules, and bankruptcy filings, there was a phone call.
Out the Gate/Prime Sports had run out of road. The original owners and investors had reached the point where fresh capital wasn’t coming, the runway was gone, and the options were narrowing fast.
That call — the one where you’re talking to people who built something and are watching it slip — is not a negotiation in the traditional sense. It’s a reckoning. You have to be honest with them about what you’re seeing, honest with yourself about what you’re actually acquiring, and honest with your own team about whether this makes sense at all.
For us, the internal conversation was just as hard. Plannatech had operated in the B2B world. This was the moment of deciding whether we were ready to go full stack — own the license, own the customer relationship, own the risk — and plant a flag in the U.S. regulated market. Not as a vendor. As an operator. That’s a different business, a different liability profile, and a different kind of accountability.
We decided it was worth it. But I want to be clear: We didn’t decide it was easy.
Asset purchase versus share purchase — and why it matters
Here’s the part that took the most legal education on my end, and I think it’s the part the industry glosses over.
In a distressed acquisition, you typically have a choice. An asset purchase lets you pick the eyes out of what’s there — take the licenses, take the technology, take what you want — and walk away from the liabilities. It’s cleaner. It’s cheaper. And it almost certainly means going dark: shutting down, rebuilding, relaunching. Vendors go unpaid. The brand takes whatever reputational hit comes with that, and you start fresh.
We chose the share purchase. It was more expensive. It took longer to process. It is, by any purely financial metric, the harder path.
We chose it because keeping customers whole mattered. Keeping vendors whole mattered. The credibility of saying we were here to stay — not to strip an asset and move on — was worth the premium. I hope regulators and consumers see that choice for what it was. It wasn’t naivety. It was a deliberate statement about what kind of operator we intend to be.
The six-leg parlay
What I couldn’t fully control was the timing.
The acquisition required regulatory approvals to happen more or less simultaneously in three states: Kentucky, New Jersey, and Ohio. We also needed the same thing to happen with three market access agreements — either renegotiated or new — across all three active states. Any one of those legs falling short potentially collapses the whole structure.
Kentucky came through. New Jersey — the crown jewel, the market that makes the economics work — had a process. A thorough one. The review ran long, but the regulators worked daily with our legal team, and we got there. The market access negotiations had their own dynamics.
And the World Cup — the single best commercial moment in the short-term calendar for a U.S. sportsbook — was right on our doorstep.
Ohio took a different path. I have no criticism of the Ohio Casino Control Commission. They do what they’re supposed to do: review everything, ask difficult questions, take the time the licensing requires. But processes have timelines, and timelines have consequences. While the commission did its due diligence, we paused taking bets in Ohio for about a month. We made the World Cup in two of Prime’s states and missed nearly all of it in the third.
Here’s the part I didn’t expect, though: During that Ohio pause, only a handful of bettors pulled their funds. Most left their balances sitting in their accounts, waiting for us to come back. Think about what that means. These are customers of a book that had just been through bankruptcy, dark in their state, and they left their money with us. That’s the share purchase decision paying off in real time. If we had gone the asset route and wiped the slate clean, that trust may not exist. One of the Ohio commissioners put it better than I could have at our approval hearing: We’re not just a corporate entity coming in trying to strip the top off the player.
The final leg landed on July 15, when the commission approved our license. We missed the World Cup in Ohio, but we are live in all three states with the first football games just weeks away. Call it a parlay where the last leg came in late. The ticket still cashed.
The long game
Here’s what I keep coming back to, though.
We are trying to do something genuinely difficult in an environment that is, frankly, not particularly friendly to what we’re attempting. State-by-state licensing. Synchronized regulatory approvals. Market access economics that favor the giants. A compliance cost structure that would make any rational investor squint.
And meanwhile, prediction markets are expanding nationally at a fraction of our cost of doing business, operating under federal CFTC oversight while we navigate three separate state processes for three separate jurisdictions. I’ve written about this elsewhere — the regulatory arbitrage is real, and it is widening. The licensed sportsbook is increasingly being asked to carry a cost burden that the new entrants simply don’t bear.
I know how that sounds. Bigger names than mine, with bigger bankrolls and better timing, have filed for bankruptcy trying to crack this market. Out the Gate is proof of that. So is a long list of operators before it. The U.S. regulated sports betting market has chewed up serious capital and serious talent.
But the reason we went through this process — the lawyers, the asset schedules, the regulatory conversations, the one-state-missed World Cup window — is because we believe the market is worth building. Not just worth entering. Worth building. The offshore market is enormous, and someone has to make the regulated alternative compelling enough to bring those customers home. That’s the work. It’s slow, it’s expensive, and the parlay doesn’t always hit on the first ticket.
We’re still writing this one.
Adam Bjorn is CEO of Plannatech Group, the parent company of Prime Sports (New Jersey, Ohio, Kentucky) and Betcris Arizona.
