Episode Info

Over the last decade, the insurtech landscape has rapidly evolved, transitioning from a space dominated by startups innovating at the fringes to becoming a thriving industry amassing huge investment and innovation.

But how did we get here, and more importantly, where do they go next?

Hippo CEO, Rick McCathron, joins Bryan Falchuk for this conversion, titled, "A Decade of Insurtech: From Startup to Success Story in 10 Years," recorded live from the main stage of ITI NYC 2025. Rick reflects on a decade of progress at Hippo, exploriing the strategies that have propelled insurtechs from industry disruptors to established market players, offering insights into what it takes to scale, sustain growth, and maintain operational excellence.

Episode Summary

This episode provides insights into effective sales and networking strategies for those selling to insurance companies. It challenges conventional sales tactics and emphasizes the importance of personalized and informed approaches.

Industry Challenges and Adaptation

Rick emphasizes the dynamic nature of the business world, noting that successful companies are those that can pivot and adapt quickly to new learnings, data, and shifts in consumer appetites.

He shares insights on the importance of making decisions with imperfect information and the need to adjust those decisions as more information becomes available.

Financial Performance and Future Outlook

Hippo has successfully met and exceeded its financial metrics, and Rick expresses confidence in the company's ability to continue this trend. He mentions an upcoming presentation to the investment community to outline their future plans.

Customer Experience and Industry Transformation

The discussion touches on the need for the insurance industry to improve customer experience, drawing parallels to Amazon's customer-centric approach. Despite progress, Rick believes there is still room for improvement.

Transparency and Management

Rick highlights the importance of transparency and ownership in management, acknowledging past mistakes and the need for change. He credits Hippo's management team for their ability to adapt and overcome challenges.

Collaboration and Industry Opportunities

The conversation also covers the need for collaboration within the industry, emphasizing that there is ample opportunity for different companies to succeed without a winner-takes-all mentality.

OverallThe interview provides a comprehensive look at Hippo Insurance's strategies, challenges, and future plans, along with broader insights into the insurance industry's evolution.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.