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 Bio

Simon 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 Discussed

00:00 – Taking over as CEO: The challenges of stepping into leadership
05:42 – Overcoming imposter syndrome and self-doubt
09:58 – Balancing career, family, and well-being during the pandemic
11:36 – Transforming health: From burnout to peak performance
17:08 – The power of delegation and trusting your team
22:11 – Lessons from leadership: Building the right company culture
26:25 – Getting out of your own head
34:28 – Simon’s charity work: From boxing to running 180 miles for a cause

Memorable 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 Links

• Connect with Simon Pilkington:
  • https://www.linkedin.com/in/simonpilkington
  • https://www.wearewander.co.uk
• Support 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/signup
• Join the iGaming Leader Mastermind: https://www.igamingleader.com/