Your Best Hire Might Have a Failed Startup on Their CV
If there’s one thing that I think would improve a lot of iGaming businesses overnight, it’s this.
Most of the senior people running iGaming businesses don’t think like business owners. They think like employees. And those are completely different operating systems.
I’ve watched this play out enough times now. Across businesses I’ve built, companies I’ve invested in, and leadership teams I’ve sat across from… that I’m convinced of one thing. You cannot train someone out of a salary brain. Either they have the founder instinct, or they don’t.
What the gap actually looks like
It doesn’t announce itself. That’s what makes it dangerous.
The person with a salary brain is often excellent at their job. Their team runs well. Processes are clean. Reporting is tidy. Everything looks fine from the outside. And then you watch them make a decision that only makes sense if your job is to look competent, not to make money.
They optimise for the task. They don’t optimise for the outcome.
The founder thinks differently. The founder asks: is this making us money? If not, why are we doing it? And if it is, how do we go harder, faster, now? They’re comfortable making asymmetric bets. They kill projects that aren’t working, even if it was their idea. They don’t need a committee meeting to move.
That instinct isn’t taught in business school. It’s not on anyone’s CV. And you absolutely cannot install it through a performance review.
The only two things that actually work
First: meaningful equity. Not the token kind handed out as a retention gesture. Real skin in the game, where the upside matters to them personally. Equity changes the way people think almost overnight. Suddenly, the business’s money feels like their money. Suddenly, they’re asking questions they never asked before. It’s not magic… it’s incentives doing what incentives do.
Second: the lived experience of building something and watching it struggle. This is the more brutal route, but it’s the more reliable one. I’ve started deliberately looking for people who have had a crack at running their own business… even if, especially if, it didn’t work out. Those people walk in carrying something no training programme can give you: the memory of what it feels like when it’s your problem at 2am, your team on the line, your money at risk.
They’re more grounded. They move faster. And they know exactly how bad certain decisions look from the other side of the table.
The uncomfortable truth for operators
If your entire leadership team is made up of career employees (people who’ve moved from company to company, collected titles, and never once had to make payroll), you have a structural problem. You might not feel it yet. Things might look fine. But you’re accumulating invisible risk.
Because when the market shifts (and in iGaming, it always does) you need people who know how to adapt, cut fast, and move on an opportunity without waiting to be told it’s safe. Career employees wait for permission. Founders ask forgiveness. In a market that moves like this one, that difference is everything.
What I’m actually doing differently
I’ve started hiring outside the industry entirely for certain roles. People who’ve never heard of a rev share model, who don’t carry iGaming’s bad habits, and who are hungry in a way that people who’ve grown up in the boom years simply aren’t.
And I’ve stopped treating “failed startup” as a red flag on a CV. It’s something that catches my eye. Someone who built something, ran into the wall, and kept going. That person understands the game at a level that most senior operators simply don’t.
The industry is full of smart, comfortable people. Smart and comfortable is a dangerous combination when you’re trying to grow.
One question to add to every senior hire process
Don’t ask about their biggest success. Ask them about the moment they realised something wasn’t working… and what they did next.
The answer will tell you almost everything about whether you’re talking to someone who thinks like a founder or someone who thinks like an employee.
That distinction will define the ceiling of your business more than any strategy, product, or market ever will.
