#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.________To support this podcast, check out our some of our sponsors & get discounts:→ $1,000 off Vanta: Your compliance superpower — vanta.com/high→ Get up to 6 months of Notion’s Business plan for free with Notion AI included (worth $12K): Go to - https://ntn.so/highflyers & click “Apply Now”If you're keen to discuss sponsorship and partnering with us or recommend future guests, email us at [email protected] today!Join our stable of commercial partners including the Australian Government, Google, KPMG, University of Melbourne and more. ________CLICK HERE to read show notes from this conversation. Please enjoy!________Follow us on Instagram, LinkedIn or TwitterGet in touch with our Founder and Host, Vidit Agarwal directly hereContact us via our website to discuss sponsorship opportunities, recommend future guests or share feedback, we love hearing how to improve! Thank you for rating / reviewing this podcast on Apple Podcasts and Spotify, it helps others find us and convince guests to come on the show! ________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.200+ guests have joined host, Vidit Agarwal on the show from 15+ countries, including The CEO's of multi-billion dollar companies like Telstra, Bunnings, Australia Post, Woolworths, Airwallex, Eucalyptus, Tennis Australia etc; Board Members at Macquarie Bank, ANZ, Reserve Bank etc; Former Prime Minister of Australia; Globally renowned Tech CEO's from Google, Microsoft, Xero etc, Successful Venture Capital and Family Office Investors; CIO's at the world's biggest superannuation funds; Leading Entertainers; Olympic Gold Medal Winning Athletes and interesting minds you wouldn't have heard of that are changing the world. Our parent company, Curiosity Centre is your on-demand intelligence hub for knowledge, connections and growth to achieve your potential, everyday. Join 200,000+ Investors, Founders, Functional Leaders, CEOs and Emerging Leaders. Learn with the world's best and be 1% better everyday at https://curiositycentre.com