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The iGaming Leader: Daily Summaries Delivered
by Leo Judkins, Founder - iGaming Leader Mastermind
The iGaming Leader is hosted by Leo Judkins, founder of The iGaming Leader Mastermind. Every other week, Leo sits down with Founders, C-suite executives, and VPs from across the iGaming industry for conversations you won't hear on a conference panel. The real decisions. The hard calls. What leadership actually looks like from the inside. No keynote polish. No PR answers. Just honest conversations between people who know the industry.
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- 3 days ago37 min
The Right Time to Sell Your Company Is When You Sell It - Benjie Cherniak
Benjie Cherniak wanted to keep running Don Best. His two business partners wanted to sell. The decision went two votes to one.He became fully committed to the deal and describes the outcome as life-changing. But selling meant adjusting to a different reality. Decisions his team could once make in a day might now take three months.In this episode of the iGaming Leader podcast, Leo Judkins speaks with Benjie about building Don Best’s in-play trading business, its sale to Scientific Games in 2018, and what founders should consider beyond the price when choosing a buyer.Benjie also shares how he found his way into investing after the exit, why he now looks more closely at how founders behave when things go wrong, and why founders should interview their investors too.ABOUT THE GUESTBenjie Cherniak is an iGaming investor and adviser. He is the principal at Avenue H Capital and serves on the board of Kambi. He was Principal and Managing Director of Don Best Sports from 2007 to 2018, leading the business through its acquisition by Scientific Games before staying on for a further two years.IN THIS EPISODE00:00 Highlights and introduction03:00 Building Don Best’s in-play trading10:00 The decision to sell Don Best13:00 Selling with or without bankers17:00 Life after an acquisition23:00 Finding purpose after an exit27:00 What investors want in founders30:00 Choosing the right investors33:00 Balancing boards, shareholders and employeesQUOTES FROM BENJIE“If it was entirely and 100% my decision, I don't think we would've sold the company at that time.”“So the right time to sell your company is when you sell your company.”“You gotta have a few misses to get the hits, right?”“How you choose your investors and how you choose your advisors and how you build your cap table, these things all have massive ramifications down the line as you're building your company.”“Appreciate it for what it was, appreciate the journey.”IMPORTANT LINKSConnect with Benjie Cherniak on LinkedIn:https://www.linkedin.com/in/benjie-c-178a302/Connect with Leo Judkins on LinkedIn:https://www.linkedin.com/in/leo-judkins/Sign up for the iGaming Leader newsletter:https://www.igamingleader.com/signupJoin the iGaming Leader Mastermind:https://www.igamingleader.com/This episode was brought to you by:Sumsub: the full-cycle verification platform helping iGaming operators onboard players, meet compliance requirements and prevent fraud. Learn more at: https://sumsub.link/8guBloomreach: the AI-powered marketing automation platform helping iGaming operators turn real-time player data into personalised engagement that supports retention and loyalty. Learn more at: https://www.bloomreach.com/en/industries/igaming
- 2 weeks ago35 min
He Was About to Sell SiGMA. Today It’s Worth 5X That - Eman Pulis
Before SiGMA, Eman Pulis had a failed business, €16,000 in bank debt and no source of revenue. The bank kept calling. His way out was to return to what he knew best: events.SiGMA grew from that low point. But Eman kept the old company name, Viking PC Health, on the invoices. He wanted a constant reminder of where he came from.In this episode of the iGaming Leader podcast, Leo Judkins speaks with SiGMA founder Eman Pulis about the setbacks behind the business, an acquisition that fell through during COVID, and why he now sees that failed exit as a silver lining.Eman also shares how he leads a global team without expecting everyone to think like a founder, why he prepares for life after an exit, and the question he keeps returning to: how much more time should go into building the business, and how much into the foundation?ABOUT THE GUESTEman Pulis is the founder of SiGMA Group, a global iGaming events and media business that began with a summit in Malta. Alongside SiGMA, he launched Ikigai Ventures and the SiGMA Foundation. His work spans international events, investment in founders and philanthropic initiatives.IN THIS EPISODE00:00 Highlights and introduction03:00 Founder ambition and exit planning06:00 Growing SiGMA beyond Malta12:00 The €16,000 failure before SiGMA16:00 Leading a global team21:00 A failed exit and crisis leadership26:00 Calculated risk and reputation30:00 Business, philanthropy and family33:00 Finding mentors as a founderQUOTES FROM EMAN“The idea of SiGMA came out of that rock bottom moment.”“I wouldn't want to take away any of the stress, any of the life lessons that came along with the pain.”“If I look after my team, they look after my business.”“Focus on the bigger picture, focus on the long term.”“Looking back, do I want to be in a position where I say, ‘Man, I could have impacted a million more person. Instead, I focus on generating another million euros.’”IMPORTANT LINKSConnect with Eman Pulis on LinkedIn:https://www.linkedin.com/in/emanpulis/Connect with Leo Judkins on LinkedIn:https://www.linkedin.com/in/leo-judkins/Sign up for the iGaming Leader newsletter:https://www.igamingleader.com/signupJoin the iGaming Leader Mastermind:https://www.igamingleader.com/This episode was brought to you by:Sumsub: the full-cycle verification platform helping iGaming operators onboard players, meet compliance requirements and prevent fraud. Learn more at: https://sumsub.link/8guBloomreach: the AI-powered marketing automation platform helping iGaming operators turn real-time player data into personalised engagement that supports retention and loyalty. Learn more at: https://www.bloomreach.com/en/industries/igaming
- Oct 7, 202644 min
“You’re Incorrect, Tommy” - Inside Xtremepush’s Culture of Challenge
In this episode, Leo talks with Tommy Kearns about how rugby shaped the way he runs a company: trust, loyalty, accountability, direct feedback and a role for everyone. He is clear about what he does not want around him. "I don't want yes men around me." Everything gets challenged until the team reaches alignment, and then everyone commits.He also covers the harder parts of the story. Tommy lost his money in the property crash after selling his Mexico business. Xtremepush was bootstrapped and profitable within 13 to 14 months. It then took growth capital in 2021 and went negative for nearly 24 months. He also talks about the 2023 Thunderbite acquisition, why Xtremepush put CRM, gamification and loyalty into one platform, and why he thinks trust matters more in the AI era.ABOUT THE GUESTTommy Kearns is CEO and Co-Founder of Xtremepush, a leading company now serving 230 iGaming brands around the world, including more than half of the EGR top 50. He is a technology entrepreneur with a track record in the global internet and mobile industry. He builds businesses that solve large customer problems for large enterprises, with technology and automation where relevant. His core skills include customer analytics and engagement, digital strategy, mobile and system application development, innovation, business planning, market entry analysis and deployment, and building commercial partnerships.IN THIS EPISODE00:00:00 Introducing Tommy00:03:00 Rugby career at Connacht and the lessons that carried into business00:08:00 Challenge and commit: no yes men and the leadership team00:12:00 Why toxicity is viral, Leaders for Leaders and hiring for urgency00:19:00 Lean culture: single-digit churn, pod systems and Keep Driving Hard (KDH)00:22:00 Career path: the Caribbean, Mexico, the 2009 property crash and the origin of Xtremepush00:28:00 Bootstrapping, growth capital in 2021 and the first acquisition00:32:00 One platform for CRM, gamification and loyalty, 24 months in the red and the Thunderbite acquisition00:38:00 Expert OS, agentic AI, trust and the power of saying noQUOTES FROM TOMMY"I don't want yes men around me. I want people to challenge my thoughts. My thoughts are directionally very good, but specifically not always correct.""Toxicity is viral. It needs to be rooted out.""You can't learn urgency. You either have it or you don't, and you have to test for it.""You have to have felt failure. You have to feel it. You have to really feel it, not just see it.""Success is not permanent, but neither is failure.""Trust is going to become more important, relationships are gonna become more important."IMPORTANT LINKSConnect with Tommy Kearns on LinkedIn: https://www.linkedin.com/in/tommykearns/Connect with Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/Get the iGaming Leader newsletter: https://www.igamingleader.com/signupJoin the iGaming Leader Mastermind: https://www.igamingleader.com/This episode is brought to you by Sumsub, the full-cycle verification platform for iGaming operators. Player onboarding, AML and fraud prevention, all in one place.Learn more: sumsub.com/gambling or https://sumsub.link/8gu
- Sep 23, 202639 min
Why This CEO Works 15-Hour Days Across Two Continents
Yoni Sidi wanted to slow down. After 17 years in corporate iGaming, he had a simple plan: build a platform, generate traffic, play golf, and reduce the pressure. Then Winpot took off in Mexico, the B2B business grew to 14 or 15 clients, and he found himself working 14 to 15-hour days across two continents. In this episode of the iGaming Leader podcast, Yoni, CEO of Wiztech Group, talks about building a bootstrapped operator and tech business from scratch, leading across cultures, and what he would tell his 2022 self.About the guest:Yoni Sidi is an experienced Chief Executive and Marketing Leader with a proven track record in the global iGaming and entertainment industry. He is currently driving growth at the intersection of technology, regulated gaming, and customer engagement, with skills across scaling brands, building high-performing teams, and developing data-driven strategies in acquisition, retention, and brand partnerships. He is passionate about bridging innovative digital platforms with real-world experiences and is actively expanding into new markets across LATAM, Europe, and beyond.In this episode:00:00 Introduction00:48 Growing up around Ronnie Rosenthal, Liverpool, and Tottenham06:29 Three years of military service as a combat instructor and what it taught him about standards08:14 Building Winpot with no outside funding, brick by brick12:38 How close he still is to the original vision of slowing down15:32 Why switching off has been harder than any commercial decision18:41 Managing two businesses across Cyprus and Mexico in different time zones26:48 The hard part of leadership is people, not strategy32:16 Learning to lead across Israeli, Mexican, British, and Cypriot cultures35:50 What he would go back and tell himself in 2022Quotes from Yoni:"My aim and vision was to literally stop generating traffic. I'd be playing golf. No pressure, no stress. We make plans and God laughs.""The bad times will feel like you have five elephants on your shoulders. The good times will not feel as good as you expect them to be.""It can be a really lonely place at the top when you're making your own decisions.""I wasted a lot of my own time and energy and deteriorated my own mental health by being too ashamed to ask for help or for advice.""I would always choose the people over the speed.""Everything will be okay. Nothing is life or death. Speak to people. Share your problems."Connect with Yoni: https://www.linkedin.com/in/yoni-sidi-b5b3a88/Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signupJoin the iGaming Leader Mastermind: https://www.igamingleader.com/This episode is sponsored by Sumsub, the full-cycle verification platform trusted by top iGaming operators worldwide. Player onboarding, AML, fraud prevention, all in one place.Learn more at https://sumsub.link/8gu
- Sep 9, 202651 min
Our Biggest Failure Is My Proudest Moment
David Carrion started as a dealer on Margarita Island, Venezuela in 1995. Thirty years later, he's Chief Strategy Officer at Gaming1, having run live poker events for PokerStars, launched a casino from scratch in his hometown, and led a four-state US market entry.In this episode of the iGaming Leader podcast, David walks us through four transitions every leader has to make: from doing to letting do, from knowing everything to knowing very little, from argument to context, and from the smaller to the bigger picture.In this episode:00:00 Guest intro00:03 Dealing cards at 18 on Margarita Island00:06 Running Casino Buenos Aires for 21 million people00:10 Launching Casino Asturias from zero00:16 The PokerStars Caribbean Adventure00:21 What PokerStars got right about culture00:36 The PCA 10th anniversary trying to break 10,000 players00:44 Launching in four US states as a relatively small Belgian company00:46 The strongest stretch of leadership I have ever went throughQuotes from David:"Launching USA was one of our biggest failures, and that's why it's one of my proudest moments.""There's nothing more dangerous than a man that doesn't know what he doesn't know.""The higher you are, the harder it is to influence.""Growth is for sure on the other side of comfort.""There aren't that many superheroes out there. There's a lot of common-sense and hard work."Connect with David: https://www.linkedin.com/in/david-carrion-82332952/Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/ Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signupJoin 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.link/8gu
- Aug 26, 202637 min
The Trap That Destroys Founder-Led Businesses 100% of The Time
What happens when you lose 100% of your revenue in back-to-back meetings on the same day?For Sidharth Swarup, it was the moment that forged everything. In this episode, Sid shares the real story behind building Ingenuity from a $1,000 investment into a business that in 2014 made more money than the previous 14 years combined. No outside investment. No borrowed money. No diluted equity.Sid opens up about running on eight treadmills at full speed for decades, fuelled by toxic energy, wearing masks until he had nothing left inside, and what it actually took to rebuild. He also makes a bold claim: the conventional wisdom of "hire the right people and get out of the way" fails founder-led businesses 100% of the time. And he explains exactly why.This one goes deep. Leadership, identity, burnout, culture, and one of the most inspiring social impact stories I have heard in years.About the GuestSidharth Swarup is the co-founder and CEO of Ingenuity Gaming, a global game development partner for casino operators and suppliers across regulated markets worldwide. Ingenuity builds high-quality games, platforms, and teams, with craftsmanship at the core.Sid co-founded the business in 2000 and has grown it without ever taking outside investment or diluting equity. He is a TEDx speaker, a member of YPO, an avid reader, a board game enthusiast, and a father. He cares deeply about how organisations grow, how leaders show up, and how culture is shaped over time.Key Topics Discussed00:00 The knockout punch. Losing both anchor clients in one day.03:00 Growing up in a bubble and believing his family was the richest in the world.05:00 Boarding school and a deep sense of abandonment.08:00 Burnout and breakdown: calling a friend asking for help.12:00 The founding of Ingenuity in 2000 with a $1,000 investment16:00 Working with his brother. Twenty years of partnership.19:00 get the right people and get out of the way fails founder-led businesses 100% of the time.22:00 Founder Mode and why Sid wishes he had read it two years earlier.24:00 Signal versus noise and why most effort goes into the wrong problems.28:00 Pulling kids off the streets of Delhi and educating them.34:00 Embracing the multi-billion-dollar ambition36:00 Advice for anyone running on eight treadmillsMemorable Quotes"It's a knockout punch. You're on your knees. You just gotta find a way to get back up.""You're running on eight different treadmills at the same time, and any day you're not living up to your ideal self, you're miserable. It doesn't matter how many good things are happening in your life.""Get the right people, but on these fronts, be in the weeds. Make sure nobody forgets.""They are heroes in their communities. The other kids have their posters up on the walls. They're a source of serious inspiration of what you can pull off.""The most selfish thing you can do as a human being is to be kind, compassionate, and generous. Because it comes back to you a hundredfold in terms of joy.""I'm still running on eight different treadmills as fast as I can, even faster than before. But it's a very different fuel now. It's not toxic fuel anymore."Key TakeawaysLosing 100% of your revenue in a single day is survivable. Ingenuity broke even in year one, turned profitable in year two, and in the year after that made more than the previous 14 years combined.The conventional wisdom of "hire the right people and get out of the way" fails in founder-led businesses. Founders must stay in the weeds on two things: keeping everyone focused on the most important problem, and protecting the resourcefulness that creates results with very little.Burnout does not announce itself. It builds under masks that the outside world cannot see. Getting help is not weakness. It is the move that changes everything.Redefine value in your organisation. Move from roles and responsibilities to problems solved. The question is not "what is your job?" but "what problem are you solving that nobody else can?"You do not have to change who you are. You have to learn to run on better fuel. Ambition, the need for validation, the drive to prove yourself: these are not flaws to fix. They are engines to redirect.Social impact and commercial excellence are not opposites. The Navodaya programme at Ingenuity is proof that a business can build high-performance teams and move people out of poverty at the same time.The conventional wisdom of "hire the right people an
- Jul 22, 202648 min
Leadership Is Learned During Days of Thunder Not of Sunshine
In this episode of the iGaming Leader Podcast, Leo sits down with Andreas (Andy) Koeberl, aerospace engineer turned entrepreneur, who built HappyBet from three people to 180, survived COVID wiping out 100% of its revenue overnight, turned around BetGames from a shrinking business into one of the most profitable live dealer companies in the world, and is now building Autonomous Minds, an AI deeptech startup creating what he calls an "agent-first Palantir."Andy talks about what real crisis leadership looks like from the inside, why the sunny periods are more dangerous than the hard ones, and why the only advisors worth having are the ones who've also failed.Guest BioAndreas (Andy) Koeberl is an engineer turned entrepreneur and CEO. He started his career in aerospace engineering before moving to Microsoft, where he honed his commercial instincts. In 2017, he co-founded HPYBET, a retail sports betting business that grew to become one of the top operators in Germany and Austria before being sold to SNI in 2020. He then joined BetGames as CEO to lead a full company turnaround, taking the business from decline to record growth years of 50% in 2024 and 45% in 2025. In late 2024, he co-founded Autonomous Minds, an AI deeptech startup building the data infrastructure layer for the agent era.Key Topics Discussed00:00 – How COVID wiped out 100% of HappyBet's revenue in 90 days.03:00 – Running a seven-figure monthly OpEx with zero revenue.06:00 – The two-column whiteboard exercise Andy used to manage the crisis.08:00 – Why not a single person quit during COVID11:00 – "Andy bombs": dropping unscheduled harsh truths and why it kept the team together.13:00 – "Shock them with your honesty." Advice from mentor Armin Sageder15:00 – Leadership is learned during days of thunder, not sunshine. 21:00 – BetGames: flying to Lithuania and finding great people.27:00 – Turning down a deal that would have more than doubled revenues to protect a niche identity.30:00 – How BetGames went from near-death to the number two crash game in its core markets and record growth.36:00 – What an "agent-first Palantir" actually means.42:00 – Burnout does not come from hard work.Memorable Quotes"You are not allowed to call yourself a senior leader until you've managed at least one substantial crisis. Not successfully. Just managed one.""Everybody can be a sunshine leader. Leadership is only forged during a crisis.""My mentor always told me: shock them with your honesty. I try to live by that in my personal life too.""Burnout does not come from hard work. It comes from emotional stress. And as a founder, you are in with your time, your accountability, and your own cash.""The best advisors are the ones who've been in your shoes and who you can call and say: I have no clue how to handle this, without being anxious about what they'll think."Important LinksFollow Andy Koeberl on LinkedIn: https://www.linkedin.com/in/koeberlandreas/Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signupJoin 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.link/8gu
- Jul 4, 202630 min
Being Great at Marketing Won't Make You a Great Marketing Leader
In this episode of the iGaming Leader Podcast, Leo sits down with Michael Baker-Mosley, ex-Head of Brand at Kambi, ex-CMO at iGP, and one of the most respected B2B marketing minds in iGaming.Michael pulls back the curtain on what it actually takes to step into a CMO role unprepared, why most B2B marketing in this industry is renting its audience rather than building one, and what happens when a leader has to let go of the people they hired and believed in. The conversation covers the art of hiring outside the industry, why picking a nemesis is a legitimate market entry strategy, the real ROI of brand, and the moment Michael went ballistic on his first holiday in years over a PR piece that was never meant to go live.Guest BioMichael Baker-Mosley is a senior marketing leader and consultant with over a decade of experience across B2B technology, iGaming, and brand strategy.He spent five years at Kambi, rising to Head of Brand Marketing, before joining iGP as CMO in January 2024, where he led the brand, PR, events, and product marketing functions through a period of significant growth and restructuring. He is widely cited as one of the most influential B2B marketers in the iGaming industry and serves as an Ambassador for the iGaming Leader Mastermind.Key Topics Discussed00:00 – From the smoking area at SBC Lisbon to the iGaming Leader: who Michael is now vs. then.02:00 – The gap nobody prepares you for: the step up from head of to C-level.05:00 – "We promote people who are good at their job. And we might get a shit manager."09:00 – The best hire Michael ever made: a risk manager from Amazon with nine months of events experience.12:00 – Two-thirds of marketers have never had formal training. What that actually means for the industry.18:00 – Delegation gone wrong: the PR piece that went live on the first day of his holiday.24:00 – Letting people go: why it is never just business, and why it should not be.28:00 – The human cost of redundancy when the team was genuinely performing.31:00 – Picking a nemesis: why having a competitor with 45 people in their B2B marketing team was a gift.34:00 – Rented audience vs. owned brand: the most expensive mistake in B2B marketing.38:00 – Why SEO, paid media, and affiliate are all forms of renting someone else's audience.41:00 – The ROI of brand: why CFOs get it wrong and CMOs let them.44:00 – What Michael would tell his earlier self on day one of the CMO role.46:00 – Why Michael became an Ambassador for the iGaming Leader.Memorable Quotes"We promote people who are good at their job. And actually it's so wrong for so many people, because you lose somebody who's good at their job and you might get a shit manager as well.""The best hire I made in my marketing team was a risk manager from Amazon. Outside the industry. Had about nine months of event management experience.""Two-thirds of marketers have never had any formal training. I've hired a risk manager from Amazon, but it's true.""I wasn't asking for people's opinions of whether or not I should be calm. It was too late. My mistake was to go ballistic.""You as a leader always have to remember: it's not about you. 'I feel bad. I hope you...' It's not about you, is it? It's about them.""If you're looking to enter a market, picking a nemesis is a great way to do it. One of our competitors had 45 people in their B2B marketing team. Ten to one outspending us. And we would find ways to subtly mock them at any opportunity.""To build long-term value for a business, marketing needs to be building brand, building its own audience, owning the audience itself. Everything else is rented."Key TakeawaysThe Promotion Trap: Promoting the best performer into management is one of the most common and costly mistakes in iGaming. You lose a high performer and risk gaining a poor manager. The skills that make someone exceptional at a job are rarely the same skills that make someone exceptional at leading others who do it.Hire for Your Weaknesses: The best hire Michael made was a risk manager from Amazon with nine months of events experience. She became one of the best hires of his career. Hiring outside the industry and outside your own strengths creates the depth of capability that frees a leader to operate at a strategic level.Rented Audience vs. Owned Brand: Paid media, affiliates, SEO, and editorial placements are all rented. When the algorithm changes, the spend stops, or the platform shifts, the audience disappears with it. The only durable asset in marketing is a brand that people seek out directly. That is what separates market leaders from permanent bit players.Picking a Nemesis: </stron
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About The iGaming Leader
The iGaming Leader is hosted by Leo Judkins, founder of The iGaming Leader Mastermind. Every other week, Leo sits down with Founders, C-suite executives, and VPs from across the iGaming industry for conversations you won't hear on a conference panel. The real decisions. The hard calls. What leadership actually looks like from the inside. No keynote polish. No PR answers. Just honest conversations between people who know the industry.
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