Dan Michelini, VP of Sales at Acrisure, joins me to discuss his unique path into the industry.

Making a massive career pivot at age 37, Dan transitioned from tech consulting and venture capital into insurance – starting with 100 cold calls a day and driving home in tears before finally catching his big break.

We discuss how he applies Ryan Holiday’s teachings on Stoicism to his daily leadership, the vital difference between a sales manager and a sales coach, and a brilliant case study on how a 24-year-old producer stole a marquee account from a 10-year veteran by selling his “inexperience.”

Dan also pulls back the curtain on the M&A landscape, sharing what made his former agency an attractive acquisition for Acrisure and what agency owners need to know about selling in 2026.

 

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