From Billion-Dollar Deals to Life on the Farm: A Conversation with Gerry DiFiore
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From Billion-Dollar Deals to Life on the Farm: A Conversation with Gerry DiFiore
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What happens when a lawyer who spent decades doing billion-dollar deals decides that his most valuable asset isn't money, but time? When his father passed away in 2019, Gerry DiFiore, a high-powered M&A lawyer, began rethinking his priorities. He realized that time was the one resource he couldn't earn back and that he needed to be far more intentional about how he spent it. In 2025, Gerry walked away from his New York legal career and headed north to his wife's bucolic family farm in Maine. In this episode of From Dawn to Dusk, hear how Gerry traded billion-dollar transactions and corporate boardrooms for growing vegetables, tending the farm, and offshore fishing in the Atlantic, and why, after a career spent helping clients measure value, he came to see the value of his own time very differently.