Richard Dennys: Business Has No Feelings: How to Scale by Being "Strategically Boring" | The iGaming Leader Podcast
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Richard Dennys: Business Has No Feelings: How to Scale by Being "Strategically Boring"

Leo sits down with Richard Dennys, a two-time CEO and turnaround specialist who has navigated the highest stakes in digital marketing and iGaming. Richard shares the dispassionate reality of the C-suite, arguing that because business isn't your friend, hard decisions must be made on common sense rat

Richard Dennys
Two-time CEO; former CEO, Game Lounge
Watch the episode Apply to the Mastermind 06 May 2026 · Sponsored by Sumsub

01 · Watch the episode

The full conversation

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02 · The guest

Richard Dennys

Two-time CEO; former CEO, Game Lounge

I am a two-time CEO who has spent the last decade building, acquiring, and scaling digital businesses in performance marketing and iGaming. Most recently I led Game Lounge, where we bought and sold assets including an eight figure exit on Betting.com. I have just left to build something independently through Free Spirit Partners, focused on acquiring digital businesses at the point where AI is reshaping the fundamentals.

Follow Richard on LinkedIn →

03 · Inside this episode

Moments worth queuing up

00:00 Business isn't your friend and why not everyone can be a CEO.
03:00 Learning commerce on the beach and in bars.
06:00 How personal loss and business failure build a "second skin".
09:00 The common enemy: using market changes to fight for transformation.
12:00 The Three Horizons.
16:00 The Home Zone.
21:00 Delaying a hard call is never a kindness.
24:00 The 10:30 Rule: nothing good happens after.
26:00 Punching Up and managing your manager.
36:00 Yield vs. Acquisition: what iGaming can learn from retail e-commerce.
39:00 Blue Oceans: building a durable affiliate business.

In his own words

01 / 04

“Business doesn't have feelings, right? It's just not your friend.”

02 / 04

“Delaying hard calls is never kindness, it's just deferred pain, and usually that pain escalates.”

03 / 04

“If you're gonna complain, complain upwards. Don't complain downwards.”

04 / 04

“It just meant that when the wind blew strong, we went fast.”

04 · Key takeaways

What to actually take from this one

Operate in Horizon Two

CEOs must leave Horizon One to their operators; a leader's value is in Horizon Two, manoeuvring toward the future.

The Strategically Boring Leader

Successful turnarounds focus on the Home Zone to drive efficiencies rather than chasing shiny objects.

Dispassionate Hard Calls

Management debt, deferring hard conversations, inevitably increases the ultimate cost to the organisation.

The Punch Up Philosophy

Always invest in the relationship with your line manager and the one above them. Build a Brand,

Not a Funnel

The only durable moat is a trusted brand that users seek out directly.

This episode is sponsored by

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