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

Coffee, Chaos, & Cashflow · Jul 17, 2025 · 37m

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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…