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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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About us
The High Flyers Podcast features in-depth interviews with the world’s most relatable role models in business, tech, finance, government and sport in the US, Australia, Singapore, India and New Zealand.
Launched over 6.5+ years ago - our 275+ guests come from various industries around the world including:
Investing and Finance (VC, PE, Pension Funds, Family Offices)
Our guests across venture capital, growth investing, institutional capital, banking, pension funds and family offices include: Keith Rabois (MD, Khosla Ventures), Jason Collins (CEO, BlackRock Asia Pacific), Ryan Beiermeister (Partner, Founders Fund), David Haber (General Partner, Andreessen Horowitz), Kevin Hartz (Managing Partner, A*), Mike Vernal (Partner, Conviction; Ex-Sequoia), David Schneider (Growth Fund Co-Lead Partner, Coatue), Venky Ganesan (Managing Partner, Menlo Ventures), Mark Suster (Managing Partner, Upfront Ventures), Kelland Reilly (Partner, Airtree; Ex General Atlantic, D1), Niki Scevak (Managing Partner, Blackbird), Paul Bassat (Managing Partner, Square Peg), David Neal (CEO, IFM Investors), Sam Sicilia (CIO, Hostplus), Michael Kim (Partner, Cendana Capital), Beezer Clarkson (Partner, Sapphire), Gautam Chari (Head of Capital Commitments, Bank of America), David Shein (Managing Partner, OIF), Vivek Bhatia (CEO, MUFG), Rowan Simpson (Founder, Hoku) and more.
Technology, AI and software (Startups, Big Tech, Publicly Listed)
Our technology, AI and software guests include Jodie Auster (Uber’s Global Head of Travel), Sukhinder Singh Cassidy (CEO, Xero), Rob Giglio (CCO, Canva), Mel Silva (MD, Google), Jean-Michel Lemieux (former CTO, Shopify and Atlassian), Anil Sabharwal (Global VP, Google Chrome, Photos and Drive), Shiv Rao (CEO, Abridge), Jesse Zhang (CEO, Decagon), Dylan Babbs (Co-Founder & CTO, Profound), John Willett (Co-Founder & COO, Rogo), David Eckstein (CFO, Legora), John Haddock (CBO, Harvey), Stevie Case (CRO, Vanta), Jeanne DeWitt Grosser (COO, Vercel), Cristina Cordova (COO, Linear), Elena Verna (Head of Growth, Lovable), Jack Zhang (CEO, Airwallex), Tim Doyle (CEO, Eucalyptus), Andrew Fraser (President, Halter), Bowen Pan (creator of Facebook Marketplace) and more.
CEOs, Boards and Major Company Senior Executives
Our guests leading some of the world's largest and most recognisable organisations include Brad Banducci (CEO, Woolworths Group), Michael Schneider (CEO, Bunnings), Paul Grosmann (CEO, R.M.Williams), Andrew Penn (CEO, Telstra), Vandita Pant (CFO, BHP), Sanjeev Gandhi (CEO, Orica), Craig Tiley (CEO, Tennis USA), Brendan Hargreaves (CFO, Officeworks), Andrew Fraser (Board Chair, Bank of Queensland), Jaddan Cummerford (CEO, Unified Music), Ed McManus (CEO, Deliveroo) and more.
Government and Policy Makers
Our government, diplomatic and public-policy guests include Malcolm Turnbull (Prime Minister of Australia), Amit Singh (Managing Partner, Mandala), Peter Varghese (Secretary of Australia's Foreign Service), Philip Green (Australia’s High Commissioner to India), Brendan Dowling (Deputy Secretary, Australia's Department of Home Affairs), Mukund Narayanamurti (General Manager for South Asia, Austrade) and Ryan Neelam (CEO, Centre for Australia-India Relations, Australian Government).
Professional Athletes
Steve Solomon (400m Olympic Sprinter), Ed Cowan (Former Test Cricketer), Trent Cotchin (3x Premiership Winning Captain, Richmond FC), Lisa Stahelakar (World Cup Winning Captain, Australian Womens Cricket Team).
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