Lessons in Grit, Growth & Global Scale from Serial Founder, Rich Joffe

Lessons in Grit, Growth & Global Scale from Rich Joffe.

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Highlights from Our Inner Circle Fireside with Rich Joffe

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Last week, Think & Grow welcomed a room full of like-minded founders to our latest Inner Circle event - a private fireside chat series designed to go beyond the glossy founder story and dig into the real, unfiltered journey behind building a high-growth company.
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Our special guest for the first one in the series was none other than Rich Joffe, serial founder and CEO of Honey Insurance. Having built and backed multiple start-ups and scaled across continents, it’s safe to say that he knows a thing or two about what it really takes to go big from Australia.
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Here’s what founders took away:

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1. Three start-ups, three different mindsets.

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Rich broke down his founder journey into three distinct acts. His first venture, Park Assist, was a classic case of urgency over strategy, fuelled by naïveté, lacking market awareness, and shaped by hard lessons in execution.
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His second company, Stella.ai, was the opposite: too much research, not enough movement. “We became masters of analysis paralysis,” he admitted. But it taught him the value of customer-funded models and scrappy resilience.
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By the time Honey Insurance rolled around, Rich had recalibrated. This time, it was about unit economics, strategic distribution, and building something billion-dollar-worthy from Australia, without needing to expand to the US and live on planes again.home without needing to live on a plane to the U.S.
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2. Australia vs. U.S.: A founder reality check.

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Building from Australia isn’t broken, but it’s not frictionless either. Rich highlighted how local investor expectations often default to a domestic trajectory, which limits valuation potential and global ambition.
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In contrast, U.S. backers tend to chase dominance and speed, backed by deeper capital pools. But attempting to scale globally from Australia often means rebuilding requires founders to move to new countries like the US and UK and setup the offices themselves, which can be distracting and operationally high risk, and comes at high personal costs that many founders are not willing to pay. offshore, and for most founders, that’s a high personal and operational cost.
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3. Resilience that’s real, not performative.

Rich shared stories of near-death moments, like a collapsed joint venture with Hippo and one heartbreaking rejection that nearly derailed Honey before launch.
His perspective? “Hard things are just events. Their meaning only becomes clear years later.” For Rich, grit isn’t about founder theatre. It’s born from desperation, personal conviction, or both.
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4. Hiring: Talent over titles.

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Forget the perfect résumé. Rich hires for hunger, adaptability, and how candidates bounce back from failure. Some of his best hires came from unconventional backgrounds. “Always hire the best athlete, not the best resume”.

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Also, one of the red flags he avoids is blame-shifting. “If someone frames every past experience failures negatively and focused on how other events and people are to blame, rather sharing how they learned and grew from the setback, that’s a dangerous mindset I don’t want on the team, I won’t move forward.”
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5. Attach to winning, not assumptions.

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Rich originally tried to apply a U.S. embedded-distribution model in Australia. It didn’t work. Instead of pushing harder, he pivoted, finding traction through white-labeled partnerships with under-marketed local financial brands. His motto: “Detach from your go-to-market fantasy. Attach to winning.”
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6. Don’t die by distraction.

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Founders often ask: “When should we expand?” Rich’s advice: “Not until you’ve fully capitalised tapped out your current local market and ideally cross sold that customer base to saturation. ”Most start-ups don’t die from distractions, not from competition, so don’t expand into new geographies or product lines until you’ve exploited the opportunity you’re working on, they die from lack of focus."

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7. What’s next? Think bigger than tech.

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Post-Honey, Rich isn’t thinking about retirement. He’s thinking about big ideas, from small modular nuclear energyapplications, to AI use cases in healthcare like and gene therapy customized medical treatments. He sees wealth not as a finish line, but as “a license to only work with talented people you respect, and on problems you’re passionate about”permission to solve meaningful problems.
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Final thoughts for founders:

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- Stay close to what you’re good at.

- Play to your unfair advantage.

- Scale and globalize and idea only when the model is working—not before.

- Embrace discomfort. It’s where the growth is.

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Thanks again to Rich for his honesty, humour, and hard-earned wisdom. If you’re a founder looking to expand into new markets, build a world-class team, or stress-test your GTM strategy, our growth team is here to help.
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Book a consultation with Think & Grow. Let’s plan your next bold move!

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