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Richard Joffe: Executive Chair & Founder, Honey Insurance
Overview
Published 8th October, 2025.
Episode #227 of The High Flyers Podcast features Richard Joffe, three-time successful founder and now Executive Chair of Honey Insurance. Previously, he built and exited startups in parking tech and HR software across New York and San Francisco.
In this conversation, Richard opens up on growing up in South Africa and Canada in an entrepreneurial family, why he walked away from McKinsey, Morgan Stanley, and Harvard Business School offers to start companies from scratch, and how rejection and restlessness became his fuel. We go deep into how he built Honey Insurance in Australia post-divorce and during COVID with no local network—raising $130M, signing national partners, and scaling to $50M ARR—plus the mental toll, the near-death moments, and his biggest lessons on building teams, co-founder dynamics, emotional plasticity, and founder psychology. He also shares what he’s now searching for after stepping back as CEO.
It’s time to explore your curiosity. Please enjoy.
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The High Flyers Podcast features in-depth interviews with the world’s most influential figures in business, tech, finance, government and sport. Launched in 2020, it has ranked in the global top ten for past three years, with listeners in 27 countries and over 200+ episodes released, and featured in Forbes, Daily Telegraph, and at SXSW.
Our guests include -- Malcolm Turnbull (Prime Minister of Australia), Anil Sabharwal (Global VP, Product at Google), Jason Collins (Head of BlackRock, Asia Pacific), Stevie Case (Chief Revenue Officer, Vanta), Brad Banducci (CEO, Woolworths), Jean-Michel Lemieux (CTO, Shopify + Atlassian), Sweta Mehra (EGM, NAB; ex CMO, ANZ), Bowen Pan (Creator, Facebook Marketplace), Sam Sicilia (Chief Investment Officer, Hostplus), Craig Tiley (CEO, Tennis Australia), John Haddock (CBO, Harvey), Niki Scevak (Co-Founder, Blackbird Ventures), Mike Schneider (CEO, Bunnings), Trent Cotchin (3x Premiership Winning Captain, Richmond FC), Peter Varghese (Secretary/Chief, Foreign Affairs, Australian Government), Jack Zhang (CEO, Airwallex), Matteo Franceschetti (CEO, Eight Sleep) and more.
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