Simon Rogerson, Founder & CEO of Octopus

Talking Frankly with Simon Rogerson, Founder & CEO of Octopus In this episode of Talking Frankly, Frankie Smith sits down with Simon Rogerson — founder and CEO of Octopus, one of the UK’s most dynamic and values-driven companies. Simon shares how he went from working in asset management to launching Octopus from a small office above a Co-op, securing his first investors from the Yellow Pages. Since then, he’s built a business grounded in kindness, innovation, and one of the most distinctive workplace cultures in the industry. Frankie and Simon dive into what it really takes to build a brilliant team, why he personally joined every job interview for years, and how Octopus empowers employees to become entrepreneurs in their own right. Simon also opens up about the challenges of balancing personal hardship — including his experience with divorce — while leading a business, and how that’s influenced his support of new ventures like amicable. One standout insight from the conversation? The power of multiple revenue streams — and why continuous innovation is key to building something that lasts. We hope you enjoy the episode.