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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enjoy!
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