In this episode of iGaming Leader, Leo sits down with Emma Blaylock, CEO of Pretty Technical and a tech leader who helped launch Kindle UK and drove early streaming at Sony. Emma shares how vulnerable leadership creates safe-to-fail teams that learn fast, stay calm under scrutiny, and execute with focus. The conversation explores helping your team feel safe-to-fail, hiring to your weaknesses, data-driven decision making, handling cashflow shocks, and female leadership in male-dominated rooms—offering practical insights for founders, product leaders, and execs across iGaming. Guest Bio Emma is an experienced business strategist and technology commercialist, having practised formal management consultancy at Deloitte and strategic investments, acquisitions and cross-group business development at Sony’s Corporate Development and M&A group in the U.S. After Sony, Emma joined Amazon and delivered strategic initiatives to launch and grow Kindle in the UK and other European markets. Emma holds a BSc in Computer Science from the University of Nottingham and an MBA from the Kellogg School of Management in Chicago. Key Topics Discussed 00:00 – Admit gaps: building a safe-to-fail culture 03:00 – Tech throughline: impact, innovation, disruption 05:00 – Bezos-level detail: data-driven calm under pressure 08:00 – Disrupting UK market with Kindle 10:00 – From imposter feelings to confident leadership 14:00 – Modelling vulnerability and psychological safety 22:00 – From Amazon to start-up: risk, family, flexibility 27:00 – Fundraising, COVID, and making hard calls 31:00 – When a big client can’t pay: cashflow and redundancies 39:00 – Raise-the-bar hiring: fill your weaknesses Memorable Quotes “No one's going to remember everything at the top of their head and have the answers for everything, that's not realistic.” “It's okay to be vulnerable around that, right? And honest around that. And then, as a team, you grow.” “That imposter syndrome we all talk about, I think it's always there, but you, you become more confident in what you can do and confident in where your weaknesses are.” “It's about having a culture that embraces failure, but then quickly learns from it.” Connect with Emma Blaylock:https://prettytechnical.io/linkedin.com/in/emmablaylockhttps://www.linkedin.com/company/pretty-technicalFollow 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/
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55:38
What it really takes to make it as a founder
In this episode of iGaming Leader, Leo sits down with Max Meltzer, founder, CEO and investor, to unpack the real mindset and habits behind building in our industry.Max charts his path from early entrepreneurship to a strategic “reset” back into employment, then leaving a top commercial role to found Strive Gaming. He shares why founders must have the guts to fail, how prioritising health and family sharpens decisions, and what it looks like to evolve from operator to strategist as the company scales.The conversation gets practical on fundraising, boards, hiring, and handling criticism without losing empathy, plus a powerful journalling practice that keeps him grounded as a leader and dad.Guest BioMax Meltzer is an entrepreneur and investor. He is the founder and CEO of Strive Gaming, a B2B Player Account Management business that serves North America. Customers include PointsBet, Golden Nugget (DraftKings), Four Winds Casino, Genting and beyond. Shareholders include Betsson, OpenBet, Knutsson and more. He is also a Venture Partner of Astralis Capital, who count PrizePicks among others in their portfolio. Max’s previous roles include CCO at Kambi and founding other businesses such as Simply Sport Management, a sports management agency launched in 2012 that still operates today.Key Topics Discussed00:00 – Welcoming our guest05:00 – Early entrepreneurship08:00 – Stigma vs strategy: going back to employement11:00 – Health over financial milestones16:00 – Making balance stick17:30 – Community, sport, and boundaries20:00 – Empathy, criticism and building thicker skin22:30 – Coaching and journalling letters to his daughter31:00 – Leaving Kambi and founding Strive36:00 – Seed strategies44:00 – Fundraising cycles, boards, and aligning investor expectations53:00 – Only do the jobs only you can do54:30 – Legacy and values: the father and leader Max wants to beMemorable Quotes“To be a success as a founder, you have to have the guts to fail. If you don’t have the guts to fail, really you shouldn’t do it.”“No one actually cares enough about you personally. Only you care about you to that extent… Do feel like, ‘what’s everyone going to think?’ No one’s actually thinking anything.”“Don’t prioritise financial milestones ahead of everything else. You’re a better business person when you prioritise your health and personal wellbeing.”“Whatever happens, prioritise family. Put your values first—your boundaries are your foundation and support.”Important LinksConnect with Max Meltzer on LinkedIn: https://www.linkedin.com/in/maxmeltzer1www.strivegaming.comhttps://www.egr.global/intel/insight/strive-founders-journey-executing-on-strategy-and-the-evolving-ways-of-raising-capital/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/
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55:51
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55:51
What compliance is NOT
Why "compliance" might be the worst job title in iGaming — and what it should really be called instead.In this episode of iGaming Leader, Leo chats with Alex Henderson, VP of Compliance at Midnite and co-host of Compliance Chronicles. From financial investigations at the UK National Crime Agency to scaling compliance teams across multiple markets, Alex reveals the hidden realities of leadership in regulated industries.What You'll Discover:Why shifting from "every customer is a criminal" changes everythingThe million-dollar mistake that taught Alex his biggest leadership lessonHow to build trust-based teams that can take calculated risksReal strategies for supporting teams without burning them outWhat to do when leadership decisions backfire publiclyWhy making mistakes is essential for growth (even expensive ones)This isn't your typical compliance conversation — it's raw, practical leadership advice for anyone managing teams in complex, regulated environments.🎧 IN THIS EPISODE 00:00 – Why "compliance" is the worst possible name for the role04:00 – Shifting mindset: not every customer is a criminal07:00 – Leadership by trust: enabling teams to take risks10:00 – When quick decisions backfire and cost millions14:00 – Customer experience in gambling: speed dating or lost forever15:00 – Building a compliance team from 1 to 30+ people17:00 – Hard leadership lessons: overwork, burnout, and compassion28:00 – Losing respect publicly and how to recover trust36:00 – When things go wrong and you're blamed unfairly40:00 – Handling redundancies and supporting people afterwards44:00 – What makes a "great leader" and the role of mistakes💡 KEY QUOTES FROM THIS EPISODE "The whole role of working in compliance is protection.""I'd rather go full-flat being innovative than follow mediocracy.""I cost the company a lot of money there… fantastic for compliance, but commercially a massive impact.""I was told early on: don't build relationships with your team because you'll have to fire them. I learned the hard way that's exactly what you should do.""I'll never stop making mistakes. They're the biggest lessons I've had in leadership."🔗 CONNECT & FOLLOWAlex Henderson on LinkedIn: https://www.linkedin.com/in/alexanda-h-114911145/Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/Subscribe to iGaming Leader newsletter: https://www.igamingleader.com/signupJoin the iGaming Leader Mastermind: https://www.igamingleader.com/ABOUT THE GUEST Alex Henderson brings extensive experience in compliance, regulatory affairs, and operational risk within the gambling sector. His career spans work with leading operators, law enforcement agencies, and advisory firms, giving him a unique perspective on both commercial and regulatory challenges. He co-hosts The Compliance Chronicles, a podcast helping peers navigate complex regulatory environments.SUBSCRIBE for more leadership insights from iGaming's top executives and innovators!
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49:34
Addiction in iGaming: A CCO’s Road to Recovery
In this episode of iGaming Leader, Leo sits down with Huw Thomas, founder of Brandstage and co-founder of the new Recovery in Gaming community. Huw shares his two-decade journey through the iGaming industry, including senior leadership roles and billion-pound exits, alongside the hidden personal battles that almost derailed his career.This conversation explores the pressures of executive life, the dangers of numbing stress with alcohol, the turning point that led to 11 years of sobriety, and why recovery conversations are vital for the future of the gaming sector. Huw also introduces Recovery in Gaming, a safe community space supporting professionals across the industry.Guest BioHuw Thomas is a brand strategist and leader in the global iGaming space. He runs Brandstage, a consultancy that partners with operators, startups, and scaleups across the UK, Europe, and the US to shape growth strategies through brand and communications.He is also co-founder of Recovery in Gaming, an industry-wide community for professionals seeking support with alcohol and drug recovery. With more than 20 years’ experience in gaming and a personal recovery journey of over a decade, Huw combines commercial expertise with a human-centred mission to build healthier leaders and organisations.Key Topics Discussed00:00 – Huw’s first step into iGaming and early industry days07:00 – Climbing the ladder: Betsson, NYX, OpenBet, and major exits14:00 – Pressure, addiction, and the turning point in 201419:00 – The first Alcoholics Anonymous meeting and life in recovery27:00 – Boundaries, control, and tools to handle executive stress33:00 – The daily inventory: a 3-minute practice that actually works37:00 – Why Huw launched Recovery in Gaming and its future impactMemorable Quotes“When that moment of surrender came, there was this level of peace and serenity that flowed through my body. All the shame and lies were finally out in the open.”“If you’ve ever thought, even once, ‘Am I drinking too much?’ the answer is probably yes.”“I didn’t realise that the feeling of no shame and full acceptance was just one step away.”Important LinksConnect with Huw Thomas:https://www.linkedin.com/in/huwowenthomas/https://www.linkedin.com/company/recovery-in-gaminghttps://www.brandstage.com/Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/Subscribe to the iGaming Leader newsletter: iGamingLeader.com/signupJoin the iGaming Leader Mastermind: iGamingLeader.com
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41:07
Why I Never Focus on Problems as a CEO — Justin Anastasi
Stay ahead of the industry. Join our newsletter for insights that will help you perform, grow, and lead at the highest level: https://www.igamingleader.com/signupIn this episode of iGaming Leader, Leo sits down with Justin Anastasi, CEO of VentureMax Group and OverPWR. With a career spanning call centres, catwalks, politics, and the C-suite, Justin shares how authenticity, resilience, and a relentless focus on solutions have shaped his leadership journey.Justin’s perspective offers fresh insights for executives and leaders who want to thrive by being themselves, while driving growth and innovation in a demanding industry.Our GuestJustin Anastasi is a seasoned iGaming executive and entrepreneur with over a decade of leadership experience. As CEO of VentureMax Group, he leads a team of industry veterans investing in disruptive start-ups and building the future of iGaming. He is also Founder and CEO at OverPWR, a Malta-based angel investment venture.Justin’s track record in global business growth, HR, and leadership development reflects his commitment to people and innovation. His unique blend of authenticity, adaptability, and entrepreneurial drive has made him a standout figure in both the iGaming and technology sectors.Key Topics00:00 – Show Intro03:00 – Breaking rules and finding your own way07:00 – Why Justin never focuses on problems10:00 – Treating time as your most valuable currency14:00 – The common thread across retail, HR, politics, and iGaming16:30 – Leading with transparency during tough decisions21:00 – Backing underdogs and seeing them succeed23:30 – Why the person matters more than the pitch deck26:00 – Speaking up on difficult issues in Malta and the industry29:00 – Lessons learned from entering politics34:00 – Balancing impatience and action in leadership37:00 – Why growth and comfort never coexist40:00 – Advice for young, ambitious leaders“I’ve never really been burdened by the problem. I’m always thinking, how am I going to get it done?”“Time is a currency. I invest it — and I don’t like to lose”“You can’t make a CEO. Somewhere within them, they have that innate ability.”“The only thing you should be is happy.”Connect with Justin Anastasi on LinkedInRead more about his work:Ethical hiring practices in MaltaWhy ESG and stakeholder capitalism matterLife’s a Pitch: Making it countFollow Leo Judkins on LinkedInSubscribe to the iGaming Leader newsletter: iGamingLeader.com/signupJoin the iGaming Leader Mastermind: iGamingLeader.com
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.
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