Drowning the voices of Imposter Syndrome with Simon Pilkington

In this episode of iGaming Leader, Leo sits down with Simon Pilkington, former CEO of KaFe Rocks and experienced iGaming executive. Simon shares his transformative journey, from navigating imposter syndrome and career shifts to prioritizing his health and well-being. They go deep into leadership challenges, personal growth, and the power of building a strong support system. Simon shares some valuable insights and practical advice for leaders striving to balance career success with personal fulfillment.Guest BioSimon Pilkington is a seasoned iGaming executive with a background in leadership, strategy, and business transformation. 17+ years in the iGaming industry, spanning operator, media and data companies, affiliate companies, and his own businesses. Not a 'straight forward' career path, but one that led to CEO leadership with KaFe Rocks. Currently running Wander, a specialist and unique recruitment business, alongside a start-up and bootstrapped affiliate company called Best Betting Media.Key Topics Discussed00:00 – Taking over as CEO: The challenges of stepping into leadership05:42 – Overcoming imposter syndrome and self-doubt09:58 – Balancing career, family, and well-being during the pandemic11:36 – Transforming health: From burnout to peak performance17:08 – The power of delegation and trusting your team22:11 – Lessons from leadership: Building the right company culture26:25 – Getting out of your own head34:28 – Simon’s charity work: From boxing to running 180 miles for a causeMemorable Quotes"I was doing everything for everyone—except myself. When I finally prioritized my well-being, everything else improved." "You don’t get rid of imposter syndrome—you learn to manage it and use it to your advantage." "Leadership isn’t about knowing everything; it’s about surrounding yourself with the right people and trusting them."Important LinksConnect with Simon Pilkington: https://www.linkedin.com/in/simonpilkingtonhttps://www.wearewander.co.ukSupport Simon’s charity run: https://www.justgiving.com/page/olivers-army-6-ultras 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/

Om Podcasten

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.