I’ll be honest with you. The people who’ve impressed me most throughout my career in this industry weren’t always the sharpest strategists or the hardest workers.
They were the ones who never stopped asking questions.
Curiosity is the most underrated trait in leadership and business. I know how that sounds like something from an airport business book you pick up before a flight. But the data is hard to ignore.
An Egon Zehnder analysis of over 1,000 C-suite executives found curiosity was the single best predictor of leadership strength. It outperformed intelligence, expertise, and determination across every competency they measured. Only 24% of employees report feeling curious at work.
The Know-It-All Problem
iGaming rewards experience. Heavily. And mostly, that’s a good thing, this is a complex, fast-moving industry where hard-won knowledge genuinely matters.
But expertise has a dark side nobody talks about.
Psychologists call it the Einstellung Effect… the way learned methods prevent you from discovering better ones. The smarter and more experienced you become, the easier it is to stop asking questions and start defending what you already believe.
I’ve sat in rooms with brilliant people (operators, platform providers, affiliates) who’ve spent twenty years mastering a version of this industry that no longer exists. They’re pattern-matching against a map that’s out of date. And they’re confident enough in their expertise that they can’t see it.
The operators who dismissed crypto as a fad. The affiliates who waved off social media. None of these were stupid people. They were experienced people who stopped being curious.
The Compounding Argument
Here’s what I’ve noticed about the most successful operators and investors I’ve worked with. They’re obsessively curious about things most people take for granted.
It’s something that I think is the biggest driver in my own life. If I touch down in a new city, the first thing I do is speak to the taxi driver, ask lots of questions, and start some research on that market.
James Clear puts it well: knowledge is the compound interest of curiosity. Information becomes more valuable the more information you already have to connect it to. Curious people accumulate more of those connections, faster, for longer. Over a career, the gap becomes enormous, and in this industry, where markets shift fast and yesterday’s playbook expires quickly, that gap is the difference between leading and catching up.
The Uncomfortable Truth
The path to senior leadership is almost perfectly designed to destroy curiosity.
You get rewarded for having answers. You build authority through certainty. You advance by being the person in the room who knows the most. So gradually, asking questions starts to feel like weakness.
It isn’t. It’s the only sustainable edge you have.
Your expertise will depreciate. The players who sit at the top of this industry in ten years won’t be the ones who accumulated the most knowledge in the last decade. They’ll be the ones who kept asking questions throughout it, about players, about markets, about businesses they didn’t fully understand yet.
The curious ones always find something worth finding. That’s the whole point.
