
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.▶▶ Sign Up For Your Free Discovery Callhttps://completegameu.com/request-a-callTimestamped Outline(00:00) Introduction: Welcome Dan Michelini(01:26) A Career Pivot at 37: From Tech Startups and VC to Insurance Sales(05:06) College Football Chaos: Notre Dame, Luke Fickell, and the NIL Era(08:52) The Daily Stoic: How Ryan Holiday’s Philosophy Shapes Dan’s Leadership(11:45) Calm Amidst the Chaos: Why Producers Must Avoid Extreme Highs and Lows(12:40) Case Study: How a Young Producer Beat a 10-Year Veteran by Selling Hunger(17:40) The 100 Cold Call Grind: Driving Home in Tears and Finding the Breakthrough(21:06) The Ripple Effect: How One Small Deal Led to Millions in Revenue Over 20 Years(25:56) Advice for New Producers: Bring Infectious Energy and Listen More Than You Talk(28:51) Sales Manager vs. Sales Coach: The Power of Servant Leadership(33:29) Hoops History: Playing for a Young Gregg Popovich at Pomona College(36:00) The Acrisure Acquisition: Why Greg Williams' Pitch Stood Out in 2017(41:42) Advice for Sellers: Navigating Valuations and Protecting Your People(43:59) Dan’s Lightning Round: Wordle, MapTap, 175-Degree Saunas, and Jack ReacherCONNECT WITH ANDY NEARY📲 Schedule a free discovery call:completegameu.com/agaSubscribe and listen to the Accelerate Your Insurance Sales Podcast 🎙 here:https://podcasters.spotify.com/pod/show/andy-neary7 🎯 Subscribe to the podcast on YouTube 🎥:https://www.youtube.com/channel/UCyqBg5tL_1G1tf7Wo98tMgg💬 Join the Complete Game text community:Text the word BROKER to 414-622-1462Connect with Andy Neary on social media: LinkedIn: https://www.linkedin.com/in/andyneary/Instagram: https://www.instagram.com/andy_neary/
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