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)

In this podcast episode, Reid whisks together a rich discussion about the essential ingredients of unforgettable industry events with experts Bryan Falchuk, President and CEO of PLRB; Chip Bacciocco, CEO of TrustedChoice.com (now a part of the Momentum family); Christen Kelley, podcast co-host and VP of Marketing at Ivans; and Jim Hackbarth, a retired industry expert and former CEO of Assurex Global.

From throwback stories about early industry events to bold strategies that push events beyond the cookie-cutter conference formula, this conversation focuses on reimagining how we meet, interact, and grow together.

Episode Highlights

• Reminiscing on first industry events (3:02)
• Favorite events (9:32)
• Fun conferences & keeping to a theme (13:31)
• Bigger events becoming pay-to-play (17:39)
• Why CIAB is great even though it’s a grind (23:16)
• Honesty is the best policy (32:39)
• How panels should work (34:00)
• Bryan’s soapbox on sales pitches (45:22)
• If you created an event, what would it look like? (52:33)

In this podcast episode, Reid talks with a returning guest – Luke Magnan, co-founder and CIO of Combined Ratio Solutions.

Luke believes that core insurance software should be accessible and affordable, much like the dependable Honda Civic. Tune in to hear Luke’s vision: to empower insurance companies by simplifying their operations without breaking the bank (and more).

Episode Highlights

• Catching up on Combined Ratio’s mission (00:50)
• Carriers running IT as an engineering shop (11:42)
• How to become the industry standard (12:39)
• Aspiring to be the Honda Civic of Policy Systems (19:34)
• The relationship between the insurance industry and tech experts (26:12)
• The next big move in the industry (28:56)
• The role of Salesforce in insurance (34:00)
• Practical solutions over cool tools (39:36)
• A concept for large companies to consider (43:49)
• How keeping exits out of the conversation opens up opportunities (47:25)
• Disadvantages of private equity and venture capital (53:51)
• Thoughts on AI (58:41)