You Only Learn on the Way Down: Lessons from a $300M Reality Check

In this episode of the iGaming Leader Podcast, Leo sits down with Charles Cohen, a serial entrepreneur who has experienced the industry's highest peaks and most isolating moments.

From building beenz.com, one of the internet’s first digital currencies, to pioneering mobile-first gaming with Probability plc, Charles shares the raw reality of leadership when the "arc of the universe" refuses to bend to your will.

Charles reflects on the "seasickness" of the .com bubble burst, where a $300 million valuation evaporated almost overnight, and the discipline required to stick to a "mobile-only" strategy when the rest of the industry was laughing at the idea.

Now leading the Department of Trust, he discusses the evolution of player safety and why the most valuable lessons in a career are almost always learned on the way down.

GUEST BIO

Charles Cohen
Founder & CEO, Department of Trust / NED Veikkaus

Charles Cohen is a veteran technology entrepreneur who has founded, listed, and exited major businesses in both the UK and US. An Oxford PPE graduate, he rose to prominence as the founder of beenz.com before becoming the CEO of Probability plc, the pioneer of mobile-centric gambling games.

Following Probability's acquisition by GTECH (now IGT), Charles spent nearly seven years as Vice President, leading global mobile and US sports betting expansion. Currently, he leads the Department of Trust, sits on the board of Veikkaus Oy, and serves on the UK Gambling Commission Industry Forum.

Key topics discussed

00:00 – You can’t negotiate with reality: Adapting or walking away.
03:00 – Realising a $300M valuation no longer applies.
09:00 – The Founder’s Trap: Being a passenger on your own train.
11:00 – Closing offices and returning value honorably.
16:00 – Why Charles resisted the "regular website" for Probability.
19:00 – Mailing physical checks in the early days of mobile.
24:00 – Every employee is taking a risk on your company.
33:00 – Why selling a business is the most stressful period.
37:00 – The PASPA Repeal: Being in the right place at the right time.
44:00 – Compliance & Automation: Where manual processes go to die.
48:00 – Why you should always have more questions than answers.

Key takeaways

Learn on the Downward Trend: Success masks inefficiency. True learning and organisational discipline are forged during downturns and failures rather than during rapid growth.

Don't Finesse the Inevitable: When a paradigm shift occurs—like a market bubble bursting—leaders must accept and adapt immediately. There is no room for denial or finessing a fundamental change in reality.

The Discipline of Specialism: Real value is built by doing something different, not by being a "different version" of what everyone else is doing. Sticking to a "mobile-first" bet when desktop was king created long-term enterprise value.

Identity vs. Momentum: High-growth startups can turn founders into "passengers on their own train." It is essential to maintain a rational perspective when behavior starts to be influenced by metrics like "fundraising" rather than core business health.

Systems Over People in Compliance: Regulatory failure is often a system failure, not a people failure. Overburdened and under-equipped departments require better data and systems (like Open Banking) to make risk-based judgments effectively.

Memorable quotes

"There's no room for denial, you can't negotiate with it... You've either got to accept it and adapt to it, or get out and walk away."

"The lesson that I took out of it ultimately is: you don't learn anything on the way up. Everything you learn, you learn on the way down."

"All this Silicon Valley horse shit about defining the future... You can not bend the arc of the universe."

"What's a couple hundred million between friends?"

Follow Charles Cohen on Linkedin:

https://www.linkedin.com/in/cohencharles/

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This episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.link/8gu