In this episode of the iGaming Leader Podcast, Leo Judkins sits down with Dan Phillips, a 30-year veteran of the industry who started his career as a trainee dealer in a Soho basement and rose to run a £2 billion turnover business. Dan shares the "no-bullshit" reality of leadership, from the gut-wrenching moment his biggest client walked away during his first week as a CEO to the complex ethics of managing global redundancies.

The conversation dives deep into the specific decisions that shape a career: why the "invincibility of youth" can be a leader's greatest asset and its biggest risk, the strategic necessity of admitting when you don't have the answer, and how to spot "wingers" in your organisation. Whether you are leading a team of five or an organisation of 700, Dan’s insights on "customer-first" leadership and the "50/25/25" framework of team commitment offer a masterclass in operational excellence.

Guest Bio

Over three decades, Dan has built a distinguished career that has taken him from the casino floor in London to senior executive positions within some of the world’s leading regulated betting and gaming organisations. 

His experience spans online, retail, and social gaming across both B2B and B2C sectors, establishing him as a respected figure in the global gaming industry. Before joining Playnetic in 2023 as CEO and subsequently as a Non-Executive Director, Dan held a series of Director, Vice President, and C-level roles with major groups including Playtech and what is now the Entain Group. In these positions, he oversaw end-to-end product, service, and operational portfolios, managing large-scale teams and P&Ls while driving innovation, regulatory compliance, and expansion into new markets. 

Alongside his corporate leadership, Dan acts as a trusted adviser to a range of global Tier 1 operators and SMEs, leading initiatives across sports betting, iGaming and casino operations, technology, regulation, product & people development, M&A, and market entry strategies. 

Key Topics Discussed

• 00:00 – Intro
• 03:00 – Learnings from the casino floor.
• 06:00 – The llack of self-exclusion tools and building early operations.
• 09:00 – Launching mobile bingo for the iPad when the market was uncertain.
• 12:00 – How to challenge experts when the pit of your stomach says something is wrong.
• 15:00 – Losing Betfair in week one and boosting business value through hard cuts.
• 19:00 – Imposter Syndrome at the top: Managing the "loneliness" and infallibility of leadership.
• 24:00 – The people you have are the people you need.
• 34:00 – The 50/25/25 Rule: you will never get 100% of people on board.
• 38:00 – The Power of "No": turning down deals is a leadership superpower.

Memorable Quotes

• ["I don't know is powerful. I would rather someone says, 'no, I don't know. Here's how I'm gonna find out.'"]
• ["It's kind of lonely at the top. There's still a feeling that as the leader of any business, you are kind of infallible. People look up to you and you struggle with that."]
• ["I hate surprises. If you don't know, tell me—it's not a problem."]
• ["I’ve done a number of commercial deals by saying no 10 times until it becomes yes."]

Key Takeaways

• Admit Your Limitations Early: The most dangerous leaders are those who "wing it." Admitting you don't know something builds trust and allows you to seek expert advice to make better decisions.
• The Reputation of an Exit: Even in a crisis, managing a transition professionally (as Dan did with Betfair) preserves long-term industry reputation, which is more valuable than any single deal.
• Stop Trying to Get 100% Alignment: Use the 50/25/25 framework: 50% are with you, 25% go with the flow, and 25% focus on themselves. As long as they aren't disruptive, focus on moving the 75% forward.
• Hire for the Pivot: In a fast-moving industry like iGaming, you need a mix of people who can handle sudden strategic shifts (e.g., Flash to HTML5) without dragging their heels.
• The Strength of Non-Creativity: Recognising you are an "operator" rather than a "visionary" allows you to surround yourself with the right creative mix to balance the business.

Important Links

• Follow Dan Phillips on LinkedIn: https://www.linkedin.com/in/dan-phillips-nel/
• Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/
• Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup
• Join the iGaming Leader Mastermind: https://www.igamingleader.com/

This episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.com/blog/knowledge-hub/gambling/

In this episode of the iGaming Leader Podcast, Leo sits down with Daniel Graetzer, the former CEO and Founder of MaximBet and Carousel Group. 

Dan shares a raw, unfiltered account of the "tumbleweed effect" that comes with rapid scaling, eye-watering valuations, and the immense pressure of managing a high-profile brand in the US market.

The conversation explores the "staring into the abyss" reality of leadership, the critical distinction between Founder Mode and Manager Mode, and the high price of isolation. 

Guest Bio

Daniel Graetzer has spent the past two decades working across the full company journey, from building and scaling businesses to transactions, restructurings and exits, across tech, AI, iGaming and digital media. 

Over that time, he has led strategy, M&A, commercial growth and international expansion across Europe, the US, LatAm and Australia. 

He has worked with founders, operators and investors through growth phases, complex deals and high-pressure strategic decisions. 

Today, his focus is on advisory work, investing and supporting early-stage companies.

Key Topics Discussed

00:00 - Raising money is just the start, not the celebration

04:00 - Sustainable High Performance

07:30 - Burnout and the "too little, too late" reality check

10:30 - Pivot to MaximBet and Nicki Minaj

14:00 - The $250M valuation that felt like a "momentum trap"

17:30 - Bullishness vs. Kidding Yourself

22:00 - How stress clouds strategic lateral thinking

26:00 - Empathy vs. Sympathy in the executive suite

30:00 - Stoicism and Values

34:00 - Mindfulness for High Performers

39:00 - Founder Mode vs. Manager Mode

Memorable Quotes

• "I don't think people should celebrate raising money... it's actually just the start of the next step."
• "Owning a business is like staring into the abyss while eating glass."
• "The train just kept getting bigger... the stakes were bigger... and at some point the macro started really going against the growth story."
• "Founder mode says: results over process any day of the week."
• "Mindfulness has had a really bad CMO."

Key Takeaways

• Raising Money is a Responsibility, Not a Win: Celebrating a fundraise can distract from the fact that anxiety and investor demands start the moment the cheque is cut.
• Founder Mode vs. Manager Mode: The traditional MBA paradigm of "hiring good people and getting out of the way" can be fatal for early-stage companies; founders must stay close to the truth of the business.
• The High Cost of Isolation: High-performers often avoid burdening family or friends with complex corporate problems, making professional support and mastermind groups essential.
• Reframing Mindfulness: Tools like breathing exercises and journaling shouldn't be seen as ways to "disconnect," but as biological "power-ups" to sustain elite executive performance.
• Decision Quality Erosion: Chronic stress narrows a leader's perspective into binary choices; maintaining a "cool head" is a requirement for creative, lateral problem-solving.

Follow Daniel Graetzer:

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

https://newtonlorenz.com/

Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/

Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup

Join the iGaming Leader Mastermind: https://www.igamingleader.com/

This episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.com/blog/knowledge-hub/gambling/

In this episode of the iGaming Leader Podcast, Leo sits down with Line Peteri, a powerhouse leader who has scaled teams across tech, fashion, and iGaming. 

Line shares her raw, unfiltered journey of building a career since age 17, only to be reduced by others to her appearance, her relationships, and her health.

She calls out the "fake bullshit" in the industry, discusses the isolation of being a high-achieving woman in her 20s, and explains why she refuses to compromise her values for a title.

Guest Bio

Line Peteri is VP - Strategic Partnerships at ATFX, operating at the intersection of performance, regulation, and global expansion in the financial trading industry. With a background in scaling brands, including co founding and growing roccamore, she brings a commercial, data driven approach to leadership and customer acquisition. Alongside her corporate role, she advises start ups on growth strategy and sustainable performance. A HYROX endurance athlete and cancer survivor, Line speaks on resilience, high performance mindset, and leading with clarity under pressure.

Key Topics Discussed
00:00 – Line calls out all the BS on Linkedin
05:30 – Being known as "the girlfriend" despite a 10-year career.
10:00 – Being dismissed at business school.
11:30 – Incurable Cancer diagnosis at age 30
14:00 – A 7-minute run led to a half-marathon and a shoe company.
16:00 – Why very little can throw Line off her game now.
19:00 – Line hires people to eventually replace her.
21:00 – Resigning when the company wouldn't allow her to protect her team.
25:30 – The Political Gap: being liked by your team isn't enough.
28:00 – Fluff and BS
33:00 – Why Line refuses to accept "Female Leader" awards.
35:00 – Advice to her 20s: "Don't give a fuck" and stop trying to blend in with the furniture.

Memorable Quotes

"I can survive cancer, I can survive anything. Even when I meet an asshole... I just think: you could just fuck off."
"I am very honest and I'm very direct... I don't really filter things. I think there's a lot of fake things going on."
"The more you begin to compromise your values, the less they become."
"If you wanna blend in with the furniture, yes, that’s what you can do. But you know what? Show yourself."
"Everything you learn, you learn on the way down."

Follow Line on LinkedIn: https://www.linkedin.com/in/linepeteri/

Follow Leo on LinkedIn: https://www.linkedin.com/in/leo-judkins/

Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup

Join the iGaming Leader Mastermind: https://www.igamingleader.com/

This episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.com/blog/knowledge-hub/gambling/

In this episode of the iGaming Leader Podcast, Leo Judkins sits down with Ebbe Groes, the co-founder and CEO of EveryMatrix. From a garage in 2008 to building the world’s largest casino aggregation platform, Ebbe has navigated the brutal realities of scaling a B2B giant without the "fuel" of massive venture capital.

Ebbe shares the high-stakes decisions of EveryMatrix’s "survival" era between 2015 and 2017, where the company nearly ran out of cash and the team took massive salary cuts to keep the dream alive. 

He pulls back the curtain on why he ringing a literal bell in meetings to keep efficiency high, the "law of large numbers" that makes VCs dangerous for founders, and why his recent decision to bring his brother in as co-CEO is about building a multigenerational legacy.

GUEST BIO

Co-founder & CEO, EveryMatrix

Ebbe Groes is a seasoned technology entrepreneur with a PhD in Economics and a proven track record of scaling software startups. Since co-founding EveryMatrix in 2008, he has transformed a bootstrapped venture into a leading global B2B iGaming provider that remains debt-free and founder-controlled. With nearly two decades of experience in the sector, Ebbe is known for his sharp commercial focus on tier-one clients and his commitment to maintaining product agility through modular, independent business units.

Key Topics Discussed

00:00 – The VC calculation: Why investors push 60% of companies "down the drain"
02:00 – From garage to global giant: The EveryMatrix origin story
04:00 – Founder-led advantages: Fast decision-making vs. board bureaucracy
06:30 – Identifying bottlenecks: your Outlook calendar is your best leadership gauge
09:00 – The 2015–2017 crisis and nearly running  out of cash
4:30 – Swapping salaries for equity during the lean years
20:00 – Why EveryMatrix only raised $4.3M in 18 years
25:00 – Watching your business dreams get taken by VCs
28:00 – The luxury of "No": Segmenting clients into Gold, Silver, and Bronze
32:30 – Co-CEO Strategy: Bringing in family to build a 100-year business
37:00 – "Chop, Chop": Removing people who aren't in the fight with you

Memorable Quotes

• "The key thing to understand about VCs is that they do their calculations on large numbers... they're going to push and accelerate to see if you belong to the 60% that go down the drain."
• "Suddenly the founders... their dreams are shut to pieces and they own 10% of the company. There's nothing fun about it. You feel then cheated from your own dreams."
• "It's important that you surround yourself with also people that think like you and you don't feel, 'oh, I'm alone in fighting this battle.'"
• "If there's some founder in a similar situation... and he feels that some people are not with him... then, you know, here's your chance to get rid of them... So chop, chop."

Key Takeaways

• The "Fuel" Trap: Venture capital often accelerates a company toward a "hit or fail" binary outcome. Founders who take too many rounds often end up as "passengers" in a company they no longer own or recognise.
• Modular Agility: Splitting a large organisation into independent business units with their own P&Ls prevents management bottlenecks and allows each product to compete as a specialist in the market.
• Transparency in Crisis: During the 2015 cash crunch, EveryMatrix survived by being radical about cost-cutting and transparent with staff, eventually converting reduced salaries into high-value equity.
• The Power of "No": Taking the wrong clients creates "opportunity cost" and disrupts your roadmap. Segmenting clients and being willing to cut off distracting revenue streams is essential for long-term scalability.
• Succession as Legacy: Bringing in a Co-CEO isn't just about bandwidth; it's about shifting from a "trade sale" mindset to a multi-generational, family-owned philosophy that preserves the company’s DNA.

Follow Ebbe Groes on LinkedIn: https://www.linkedin.com/in/ebbe-groes/

Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/
Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup
Join the iGaming Leader Mastermind: https://www.igamingleader.com/

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/

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

This episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.com/blog/knowledge-hub/gambling/

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 Rokker.

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 BIO

Andy Rogers
Founder and CEO of Rokker

Andy 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 Discussed

00:00 - Patient strategy and the "fuck it, I'll figure it out" mindset
03:00 - Launching a first agency and the transition to "proper" jobs
05:00 - Walking away from an acquisition payday at Media Tech
09:00 - Why Andy chose to bootstrap Rokker instead of raising VC
12:00 - Running your own race: Refusing to judge success by others' achievements
18:00 - Reverse engineering a 10-year life and financial plan
21:00 - The "Mad Plan": Incubating four businesses by waiting for the right people
27:00 - Capital deployment: Deciding which fire to put out first
34:00 - Listening to accountants without letting spreadsheets kill growth
41:00 - Undercapitalisation: The canary in the coal mine for business failure
43:00 - Why it is expensive to be poor: Blood in the water and bad deals
50:00 - Advice to 25-year-old Andy: Get into gaming earlier and back yourself

Memorable 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 Takeaways

Patience 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.uk
www.rokkerx.team
www.prettytechnical.io

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

This episode is sponsored by Sumsub, the leading identity verification provider for iGaming operators. Learn more at https://sumsub.com/blog/knowledge-hub/gambling/

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

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

In this episode of the iGaming Leader Podcast, Leo sits down with Elen Barber, who went from affiliate manager to CMO at Kindred in just nine years, to explore what it really takes to lead through the industry's toughest challenges.

Elen shares the brutal reality of her first weeks as CMO: facing a £100 million fine, Swedish re-regulation, plummeting share price, and multiple rounds of restructuring that forced her to make impossible decisions about people she'd worked alongside for years. She reveals how she kept 550 people motivated while simultaneously having to cut headcount, and why the loneliness at the top hit harder than she expected.

About Elen Barber

Elen Barber has been working in the gaming industry for over 20 years and has witnessed its evolution from the wild west days to today's highly regulated landscape. She's held CMO roles at Super Group and Kindred Group, managing teams across multiple countries and dealing with everything from new market launches to regulatory curveballs. Based in London, she's passionate about how this industry continues to reinvent itself.

Key Topics Discussed

00:00 - Elen Barbers iGaming Journey
03:00 - Creating your own opportunities: you can't wait for your manager
08:00 - Why the higher you go, the lonelier it gets (and how to handle it)
14:00 - Wearing different hats: the two-chair technique for managing emotions
18:00 - Building trust: having your team's back and showing your true nature
22:00 - The worst crisis in company history hits in week one as CMO
26:00 - Managing multiple restructures while keeping people motivated
34:00 - Life after Kindred: why career breaks aren't always roses
36:00 - The pressure of being a perfect parent, perfect exec, perfect everything
41:00 - Quick fire Q&A: leadership advice, mistakes, and legacy

Memorable Quotes

"It is too easy to make money in our industry comparing to any other industries. The margins are much higher. So we are spoiled for this. It doesn't drive innovation."

"You also create opportunities, you don't wait for the opportunities to be created for you. You can't rely completely on your manager to get you through your career."

"And it is scary for the leader to understand and accept that suddenly you know significantly less than people within your team."

"I've been working all my life, and I didn't know how to relax, I missed that mental stimulation. "

"You really have to try to take emotions out of the business decisions because these things do not work together."

Connect with Elen Barber

LinkedIn: https://www.linkedin.com/in/elen-barber/

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In this episode of the iGaming Leader Podcast, Leo sits down with veteran executive David McDowell, co-founder of FSB Technology and an early pioneer in the B2B platform space, to unpack the brutal reality of the 30-year entrepreneurial journey.

David shares the truth about leadership burnout (it's the weight of the decisions, not the hours), the biggest mistake CEOs make when scaling (waiting too long to remove a talented but toxic employee), and the devastating cost of losing your vision.

He offers a raw, cathartic reflection on the final chapters of FSB: being named Platform of the Year, only to have the momentum killed by a lack of capital investment demanded by a board focused on short-term liquidity. This is a crucial lesson in battling the "noise to the vision" and the indispensable wisdom only gained by staying in the game long enough to get the wins.

About David McDowell

David started his career as an engineer in Michigan and moved to London to do an MBA in 1993. He launched his first business, a two-sided marketplace using college students to teach adults how to use the internet, in 1995. He has since spent 25 years in the gambling industry.

He co-founded GameAccount (now GAN), an early skill games provider that pivoted to B2B casino games and platform provider before its IPO in 2013.
He co-founded and was CEO for 15 years of FSB Technology, a B2B sports betting platform that was sold to PE in 2019 and on to EveryMatrix in 2024.

He currently works as an independent consultant with various gambling-related businesses and serves as an Entrepreneur Mentor in Residence at London Business School.

Key Topics Discussed

00:00 - The entrepreneurial philosophy
04:00 - Building the first venture (SOS) in 1995
06:15 - Transitioning to CEO: becoming the external face of the organisation
07:45 - It often feels like everything that you do is a mistake
10:00 - Managing burnout: the importance of compartmentalising and health
16:30 - Careful who your investors are
19:20 - The fundraising Goldilocks problem: minimising dilution while maximising runway
24:30 - Why customer-led features are often an absolute waste of time
31:00 - Knowing in your gut someone is wrong for the organisation
37:00 - Communicating your vision clearly
39:00 - Isolation in leadership
47:00 - What would I do differently going back

Memorable Quotes

"The entrepreneurial journey is just staying in the game long enough so that you can get the wins."
"All of those are almost noise to the vision. You still have to kind of make sure that you're building your own vision..."
"My biggest mistake is waiting too long [to remove a cultural mismatch] because I thought we need... we can't afford the disruption right now."

Connect with David McDowell

LinkedIn: https://www.linkedin.com/in/david-mcdowell-547209?lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_contact_details%3BomU134VSR%2B2eskLlRqTFHQ%3D%3D

Follow Leo Judkins & iGaming Leader

LinkedIn: https://www.linkedin.com/in/leo-judkins/
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