Insights

Why iGaming founders have no one to talk to

Who do you call when the ground moves under a market you’ve built your business on?

Leo Judkins, Founder, The iGaming Leader  ·  September 2026

On the 25th of September, the Brazilian government announced a provisional measure banning all regulated online betting. Immediately. Fixed-odds sports betting, online casino, gone, effective within days. No new deposits. Sites blocked within a fortnight. Advertising contracts terminated. Sponsorships torn up, no transition period for the football clubs that had built entire commercial models around them.

Less than three years earlier, that same market had been legalised. Operators had paid R$30 million each for a five-year licence. Billions had gone into building one of the most tightly controlled betting markets in the world. And then, overnight, the government switched it off.

If you had money in that market on the 24th of September, what was your playbook for the 25th? Who did you call?

That’s the question that defines this industry. Not "who do you know." Who do you call when the ground moves under a market you’ve built your business on, and it moves in a way nobody outside the room could have predicted.

Why this hits harder in iGaming than almost anywhere else

Every industry has pressure. Not every industry has this specific combination: enormous commercial and regulatory exposure, a pace that can turn a legal, licensed, thriving market into an illegal one inside a single news cycle, and an industry small enough that everyone in it already knows everyone else.

That combination is what makes iGaming different. What’s true this minute can be untrue the next. There’s no playbook for a regulated market getting switched off overnight, because it doesn’t happen anywhere else the way it happens here.

And because the industry is so small and so relationship-driven, the people you’d naturally want to talk something like that through with are often the same people you can’t afford to be candid with. Confide in a peer about a problem with your executive team, and there’s a real chance it reaches that executive, or reaches someone who starts circling to poach them. Talk about which clients are driving your numbers, and every other B2B supplier chasing that same operator now knows exactly where to point their sales team. The industry is small enough that a private conversation rarely stays private for long.

On top of that, this industry runs on visible success. Podcasts, panels, award stages, award-winning news coverage, one success story after another. When you’re the one sitting on a problem instead of a win, that steady stream of other people’s highlight reels makes you feel like you’re the only one struggling. You’re not. You just haven’t heard from the people going through the same thing, because none of them are talking about it publicly either.

The decisions that don’t get made

Here’s the part people don’t expect. It’s not really about the dramatic, sudden decisions, the market shutting down overnight, the crisis that forces your hand. Those, at least, force a response.

The decisions that quietly cause the most damage are the ones that never get made at all. The restructure you know needs to happen. The change to your C-suite that would fix the culture problem everyone can feel but no one names. The pivot you’re 80% sure is right, but not 100%.

Those are one-way doors. You can’t undo a full executive restructure once you’ve made it, and you can’t easily reverse the ripple effects through the rest of the business. So the decision sits. And the longer it sits, the harder it gets, because every week that passes makes the eventual conversation more overdue, more awkward, and more obviously late.

Who do you actually talk that through with? Not your board, they want you to arrive with it already figured out, not thinking out loud in front of them. An executive coach can help you clarify your own thinking, but they’ve rarely sat where you’re sitting, and they can’t show you the scar tissue from having made that exact call before. Your friends don’t fully understand the stakes. Your partner has heard enough about work for one week. And obviously, you can’t run it past the people whose jobs are on the line.

So it doesn’t get talked through. It just sits, 80% decided, for months.

I’ve watched this play out inside our own community. One of our members had been sitting on a full organisational restructure for a long time, a decision that was entirely theirs to make, which is exactly why it kept not getting made. It’s hard to move on a decision when there’s no one else in the room forcing the conversation forward. They brought it to their first Inner Circle session. By the end of that one conversation, they had the clarity, the confidence and the conviction to make the call, and make it quickly. Nothing about the decision itself had changed. What changed was that, for the first time, they weren’t the only person in the room who understood what was at stake.

What happened in our community the day Brazil fell apart

The same week the Brazil news broke, it landed inside our own Mastermind community within the hour. Not as panic, as clarity.

One of our members, someone with over two decades in this industry, had already been through enough regulatory upheaval to know the difference between what the headlines were saying and what would actually happen next. They broke down the legal mechanics for the rest of the group: what a provisional measure actually means, how long it can run before it needs converting into law, what a court challenge would and wouldn’t achieve, and what the realistic timeline for the market looked like whether or not the measure ultimately survived.

Within an hour, a room full of senior operators who could easily have spent the day reacting to headlines had a grounded, realistic read on what was actually happening, and what to plan for regardless of how the politics played out.

That’s the value of having the right people in the room when something like this hits. Not because someone hands you the answer. Because someone who’s lived through enough of these moments before can tell you what actually matters in the first 48 hours, while everyone else is still refreshing the news.

What this actually costs you

None of this is really about missing one piece of advice on one bad week. It’s about what happens over years of making decisions like these without anyone in the room who’s carried the same weight.

Decisions get made on incomplete information. Blind spots stay blind spots, because nobody’s close enough, and trusted enough, to point them out. The restructure sits for six months longer than it needed to. The 80% conviction never becomes 100%, so nothing moves. And the person carrying all of it does so quietly, because in this industry, saying it out loud usually costs more than staying silent.

Where this changes

This is exactly the gap The iGaming Leader exists to close. A highly vetted group of four or five other founders, CEOs and senior executives, at your level, bound by a genuine confidentiality agreement, with no other agenda but yours. No pitching, no performing, no one angling to poach your best hire or your biggest client. Just people who’ve made calls like yours before, and will tell you honestly what they got right and what they got badly wrong.

See how the Inner Circles work→

Questions this usually raises

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