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Episode 95 | October 31, 2025

Riding the Waves of Change

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In this final podcast episode, Reid reflects on his journey, including his early years, a career in insurtech, the connections he has forged, his roles as a podcast host, CEO, and entrepreneur, and the lessons he has learned along the way.

As Reid steps into a new chapter – mastering music and inspiring passion – he leaves behind a legacy that challenges us all to think bigger, connect deeper, and embrace innovation. Tune in to hear Reid in the hot seat with Jim Hackbarth, a retired industry expert and former CEO of Assurex Global (and a well-known guest on the podcast).

Episode Highlights

  • Laguna Beach skateboarding roots and forest ranger ambitions (1:00)

  • Construction, landscaping and the value with your hands (8:06)

  • Solving insurance issues with technology (9:30)

  • Reid’s evolving understanding of leadership (21:18)

  • How does Reid define success (36:11)

  • Fun: cars, dirt bikes, boats, freediving, spearfishing, camping, and more (38:55)

  • Reminiscing on what will be missed about Ivans and Applied (46:00)

Watch this episode on YouTube!

“I never thought that it [the podcast] would be as powerful as it has been for the industry… It kind of like blew up a little bit in its own way. But it's just been a lot of fun. This business has been a lot of fun. We did some really cool things.”

Reid Holzworth
CEO Ivans

Check Out the Insurance Technology Podcast on YouTube

We’re excited to share that the Insurance Technology Podcast is now on YouTube! You can catch all the previous episodes, and can now watch the newly released episodes in a new video format.

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