In this episode of the iGaming Leader Podcast, Leo sits down with Ian Freeman, a commercial powerhouse who has navigated the high-stakes world of Kambi, IGT, and Inspired Entertainment.

Ian pulls back the curtain on the "Bait and Switch" of executive leadership, the moments when the glossy job description meets the grim reality of a business in crisis.

Ian reflects on the formative trauma of losing his father at 20 and how carrying a family legacy forged a "survive and thrive" mentality that defined his career.

He shares the brutal honesty of walking into his first board meeting at a new firm only to realise the company was on the verge of insolvency, and how he learned, through painful trial and error, that coming in "too hot" can sometimes fuel the fire rather than put it out.

Key topics discussed

00:00 – The First Board Meeting: Realising there wasn't "another page" to the numbers.
03:00 – Formative Crisis: Losing a father at 45 and taking over the family legacy at 20.
07:00 – Breaking Down: The moment Ian realised he was living his father's life, not his own.
08:00 – Fishing with Ted Baker: Lessons in entrepreneurship from the riverbank.
10:00 – The "Moxie" Days: Learning the John McMahon sales toolkit.
13:00 – The Scandinavian Consensus: What iGaming can learn from Kambi’s leadership culture.
19:00 – Walking into Insolvency: How to lead when everyone's "hair is on fire."
24:00 – The Danger of "Coming in Hot": Why speed isn't always the answer in a turnaround.
28:00 – The Fear of Failure: Admitting when you need help in the C-Suite.
33:00 – The B2B Sin: Why failing to deliver technology is "killing" your customers' businesses.
40:00 – Living for Two: How Ian carries his father's legacy into the next 20 years of iGaming.

GUEST BIO

Ian Freeman, former CCO & CRO (Kambi, IGT, Inspired Entertainment), is a veteran commercial leader with over 20 years of experience across Europe, North America, and LatAm. From driving Kambi’s landmark IPO to navigating the complex regulatory waters of Brazil for Inspired, Ian has seen the industry from every angle. Beyond the boardroom, Ian is a devoted father in a blended family and a passionate fly fisherman who finds his clarity in the silence of nature.

Follow Ian Freeman on Linkedin: www.linkedin.com/in/free-man

Follow Leo Judkins & iGaming Leader

LinkedIn: https://www.linkedin.com/in/leo-judkins/
Newsletter: https://www.igamingleader.com/subscribe
Join the Mastermind: https://www.igamingleader.com/apply