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David Kaplan didn't come up through the industry the traditional way. He went to art school, never tended bar a day in his life, and opened Death & Co in New York's East Village on New Year's Eve 2006 with a vintage cash register and zero business experience. What followed was twenty years of one of the most influential runs in American hospitality — a craft cocktail institution that helped shape how a generation drinks, thinks about bars, and expects to be taken care of.

But David was never just building a bar. He was building a brand, a culture, and eventually a company — Gin & Luck — that now spans consulting, multiple Death & Co locations, and his newest venture: Midnight Auteur Hotels, whose first property, Municipal Grand in Savannah, is already turning heads.

In this episode, David traces the full arc. We get into the origin story, the partnership drama that stalled expansion for years, why he walked away from a family office overlooking Central Park to raise $18 million from 5,000 individual investors instead, and what it actually takes to scale hospitality without losing the thing that made it special in the first place.

Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.

Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.