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The iGaming Leader

The iGaming Leader

Written by: Leo Judkins - Coach for iGaming Leaders
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 The iGaming Leader Podcast with Leo Judkins uncovers the human side of the iGaming industry's most successful leaders. Join us as we explore the untold stories, challenges, and triumphs of the executives shaping one of the world's most dynamic sectors. Each week, we dive deep into conversations with C-suite leaders, founders, and directors from global betting firms and innovative startups. Our guests share their authentic journey to the top, revealing pivotal career moments, leadership philosophies, and personal strategies for sustainable success in this high-pressure industry. More than just another business podcast, we focus on the crucial intersection of wellbeing and high performance. Discover how industry leaders maintain peak performance while managing stress, work-life integration, and team dynamics in an industry that never sleeps. Whether you're an aspiring leader, current executive, or passionate about the iGaming sector, each 30-minute episode delivers actionable insights to help you thrive in this fast-paced environment. Subscribe now to join a community of high-achieving iGaming professionals committed to making this industry not just successful, but sustainable for its leaders.© 2024 iGamingLeader.com Careers Economics Management Management & Leadership Personal Success
Episodes
  • The Secrets to Running 4 Companies in iGaming

    The Secrets to Running 4 Companies in iGaming
    Feb 25 2026
    In this episode of the iGaming Leader Podcast, Leo Judkins sits down with Andy Rogers, the quiet force behind some of the industry's most significant behind-the-scenes developments. Andy shares his journey from industrial design to launching and exiting multiple agencies and technology firms, including his strategic tenure at Media Tech and the eventual founding of Rocker.The conversation explores strategic decision-making under intense constraints, the intricacies of business design, and the reality of navigating a "mad" 10-year plan. Andy offers deep insights into the value of patience, the importance of running your own race, and why being undercapitalised is the most expensive mistake an executive can make.GUEST BIOAndy RogersFounder of Rocker & MD of Pretty TechnicalAndy has been an MD, CEO, Investor, and Board member in the digital and gaming industries for 28 years. After studying Industrial Design at Brunel University, he launched his own design agency in 1998, working through the dotcom boom and bust, developing the UK's first online trading platform, and even running a military database business. He later joined Lightmaker as Managing Director, scaling it into a global leader with clients like Manchester United, Sony, and Nintendo.After moving to London to lead the digital arm of ETV Media Group, Andy entered the iGaming sector, eventually building the world’s first B2B social gaming platform. Following the sale of that business to Mediatech, he served as their Managing Director in Spain, overseeing nearly a third of the country's online GGR. In 2015, Andy founded Rokker, acting as an incubator for ventures including Random Colour Animal, Skull Mountain, and Pretty Technical, where he continues to lead today.Key Topics Discussed00:00 - Patient strategy and the "fuck it, I'll figure it out" mindset03:00 - Launching a first agency and the transition to "proper" jobs05:00 - Walking away from an acquisition payday at Media Tech09:00 - Why Andy chose to bootstrap Rocker instead of raising VC12:00 - Running your own race: Refusing to judge success by others' achievements18:00 - Reverse engineering a 10-year life and financial plan21:00 - The "Mad Plan": Incubating four businesses by waiting for the right people27:00 - Capital deployment: Deciding which fire to put out first34:00 - Listening to accountants without letting spreadsheets kill growth41:00 - Undercapitalisation: The canary in the coal mine for business failure43:00 - Why it is expensive to be poor: Blood in the water and bad deals50:00 - Advice to 25-year-old Andy: Get into gaming earlier and back yourselfMemorable Quotes"Our success is directly proportional to the number of times you've said: fuck it, I'll figure it out.""Investing is easy if you have an infinite amount of time.""It's expensive to be poor. You get worse deals, you get worse rates, someone can see the blood in the water.""Run your own race... I'm comfortable in my own skin to run my own race.""When you know, you know. There is no amount of swinging for the boundaries... you just know it's done."Key TakeawaysPatience is a Competitive Advantage: By giving himself a 10-to-15-year horizon rather than a standard 3-year VC cycle, Andy was able to build value without the pressure of external shareholders.The "Expensive to be Poor" Trap: Running a business undercapitalised forces you to take bad projects and accept suboptimal deals because investors can "see the blood in the water".Don't Cut Costs to Growth: While accountants are essential for structure, cost-cutting your way to a growth target is often a "convenient memory loss" that ignores the initial investment required to hit those numbers.Success is Contextual: Most industry success is based on context and timing rather than purely personal ability; leaders must be honest enough to admit when luck played a role.Back Yourself to Run Again: The highest leverage a young leader has is the conviction to run their own race rather than helping someone else achieve their goals at the expense of their own conviction.Follow Andy Rogers:https://www.linkedin.com/in/andyrogersprofile/www.rokker.co.ukwww.rokkerx.teamwww.prettytechnical.ioFollow Leo Judkins & iGaming LeaderLinkedIn: https://www.linkedin.com/in/leo-judkins/Newsletter: https://www.igamingleader.com/subscribeJoin the Mastermind: https://www.igamingleader.com/applyThis episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.com/blog/knowledge-hub/gambling/
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    53 mins
  • Your Company is Not a Family: Bootstrapping Lessons with the Founder of TESTA

    Your Company is Not a Family: Bootstrapping Lessons with the Founder of TESTA
    Feb 13 2026

    In this episode of the iGaming Leader Podcast, Leo sits down with Kyle Wiltshire, the founder and CEO of TESTA. Kyle takes us on a journey from the high-octane "Wild West" days of Bodog in Manila to building a global, bootstrapped testing powerhouse from his base in Taipei.

    Kyle shares the "brutal" reality of scaling an operation from 50 to 1,200 people in a flash, the hard-learned lessons of dealing with technical partners who try to "hold products hostage," and why he believes the common corporate trope of "we are a family" is actually toxic for performance. He opens up about his philosophy of "making yourself non-essential" and why the most successful leaders are generalists who know exactly when to hand off the ball.

    GUEST BIO

    Kyle Wiltshire
    Founder & CEO, TESTA

    Kyle Wiltshire is a technical-leader-turned-entrepreneur who specialised in DevOps and backend innovation long before they were buzzwords. After years of driving massive scalability for Asia-facing operators, he founded TESTA in 2023 to solve a persistent industry pain point: real-world, crowdsourced QA for the global iGaming sector. Based in Taipei, Kyle is a self-proclaimed "generalist" with an MBA who believes in building lean, profitable businesses in uncontested markets.

    Key topics discussed

    00:00 – Why a company is a sports team, not a family.
    02:00 – Moving to Manila: The "brutal" 12-hour time difference and the project that never ended.
    04:00 – The Bodog Days: Scaling from 50 to 1,200 people and the chaos of "two of everything."
    09:00 – The Partner Betrayal: How a startup partner tried to hold code hostage for equity.
    14:00 – The Ethics of Equity: Why Kyle is now "freewheeling" no more with cap tables.
    16:00 – The Bootstrap Constraint: Why saying "no" to VC money made TESTA a more scientific business.
    23:00 – Finding the "Blue Ocean": Why Kyle chose crowdsourced testing over the "Red Ocean" of slot studios.
    26:00 – The Squeaky Wheel: Why coaching low performers is a drain on the high performers.
    31:00 – Parroting vs. Execution: The challenge of "yes-men" in diverse global cultures.
    36:00 – The Art of the Handoff: How to get over yourself and let the team run the booth.
    43:00 – The Vince McMahon Lesson: Railroaded ambition and disrupting regional territories.

    Key takeaways

    The Sports Team vs. Family Model: A family is unconditional; a company is mission-based. Viewing your team as a high-performance sports unit allows for the "ruthless" but necessary decisions required to protect the organisation's goals.

    Make Yourself Non-Essential: The ultimate goal of a founder is to be "off the critical path." If a business requires you to be the subject matter expert in every room, you haven't built a company—you've built a job.

    The "Mom Test" for Software: You can have all the data in the world, but you will always learn more by watching a real person use your product in their own environment. Data tells you what is happening; stories tell you why.

    Bootstrap for Clarity: Outside capital often forces a "race to the top" that ignores product-market fit. Spending "money that would have been in your pocket" forces a more disciplined, scientific approach to growth.

    Stop Fixing People: In leadership, you cannot solve people like a technical challenge. Spending excessive time coaching a low performer isn't just a waste of your time—it’s an insult to your high performers who are actually carrying the weight.

    Memorable quotes

    "A company is not a family. Let's be honest, we're trying to accomplish this thing... It’s not, we're all just here to hug each other and sing Kumbaya."

    "How would you ever get promoted if they absolutely need you to do the thing that you do? The goal is to make yourself not essential."

    "If you are clever enough to build another slot company in 2026, good on you... I like the uncontested space."

    "You have to learn to fire people when it’s not working because it’s actually this weird superpower that brings the whole group together."

    Connect with Kyle Wiltshire:

    https://www.testa.io
    https://www.linkedin.com/in/kwiltshire/
    https://next.io/podcasts/next-io-podcast/kyle-wiltshire-the-truth-about-doing-business-in-southeast-asia/

    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
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    46 mins
  • The "Bait and Switch" of the C-Suite: Dealing with the gap between the job description and the reality of a company in trouble.

    The "Bait and Switch" of the C-Suite: Dealing with the gap between the job description and the reality of a company in trouble.
    Feb 6 2026

    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
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    43 mins
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