#34 Deciding in the Dark: High-Stakes Leadership When Paths Aren’t Clear feat. Michael Hearn

In this candid conversation, Michael Hearn unpacks his entrepreneurial journey—from the collapse of his first startup to strategically building and selling his tea company. But his story doesn’t stop there: After exiting his business, Michael transitioned into business banking, where he led 40+ bankers and advised over 1,000 companies on growth, capital, and high-stakes financial decisions. He reveals how real-world failure shaped his leadership in banking, why mental resilience is the entrepreneur’s most critical tool, and how his dual perspective—as both a founder who’s sold a business and an advisor who’s guided others through exits—equips him to help leaders navigate uncertainty. Expect raw lessons on rebuilding, the emotional toll of pivots, and why community support separates those who survive from those who thrive.

Connect with Michael: https://www.linkedin.com/in/michael-hearn-iii-0115b3213/