#227 Richard Joffe: The Founder Who Wouldn’t Quit — 3 Startups, 300 Rejections, a Divorce, and a $1B+ Legacy

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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CLICK HERE to read show notes from this conversation. Please enjoy!

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The High Flyers Podcast is described as a "meticulously researched biography" that uncovers the untold stories of remarkable people and companies -- redefining the "high flyer". Launched in 2020, we have ranked in the global top ten podcasts for past two years, with listeners in 27 countries and over 200 episodes released. Excerpts of the podcast have been featured in Forbes, AFR, Daily Telegraph, and showcased at SXSW.

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