Charles Cohen: You Only Learn on the Way Down: Lessons from a $300M Reality Check | The iGaming Leader Podcast
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The iGaming Leader Podcast

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

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 reality of leadersh

Charles Cohen
Founder & CEO, Department of Trust
Watch the episode Apply to the Mastermind 07 Mar 2026 · Sponsored by Sumsub

01 · Watch the episode

The full conversation

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02 · The guest

Charles Cohen

Founder & CEO, Department of Trust

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03 · Inside this episode

Moments worth queuing up

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.

In his own words

01 / 04

“There's no room for denial, you can't negotiate with it.”

02 / 04

“The lesson that I took out of it ultimately is: you don't learn anything on the way up.”

03 / 04

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

04 / 04

“What's a couple hundred million between friends?”

04 · Key takeaways

What to actually take from this one

Learn on the Downward Trend

True learning and organisational discipline are forged during downturns rather than rapid growth.

Don't Finesse the Inevitable

When a paradigm shift occurs, leaders must accept and adapt immediately.

The Discipline of Specialism

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.

Systems Over People in Compliance

Regulatory failure is often a system failure, not a people failure.

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