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A man casually mentions he owns a haunted house. Not a side gig—a real business entering its fifth year, staffed with 40 live actors and animatronics that cost serious money. The origin story starts with Hurricane Ida flooding a Philadelphia neighborhood, a stalled real estate deal, and a decision to transform a flooded bar into something entirely different. But the deeper story traces back three generations: a grandfather in the Bronx making a choice, a father remembering his parents fighting about risk in the kitchen, and a son who at forty did what his father was too afraid to do until much later.
Michael Adler is a lawyer and entrepreneur who specializes in turning side hustles into full-time businesses. He coaches founders, invests in their ventures, and takes equity as payment. He's failed multiple times and wears those failures as badges. On this episode of Lawsuits & Lessons, Michael breaks down what separates people who start businesses from those who actually build them—and why understanding that your first plan will be wrong is the whole point of starting.
Steve Cooper brought Michael on because they speak the same language: the work is front-loaded, the risk comes first, and ownership rewires how you see everything. This is a conversation about generational patterns, the courage it takes to leap when your family didn't, and what a good lawyer who still practices law while running real estate deals and haunted houses can teach you about building something real.
About the Guest: Michael Adler is a lawyer, entrepreneur, and startup advisor who works with founders to scale their businesses. He brings hands-on experience across real estate, hospitality, and emerging ventures, combining legal expertise with practical entrepreneurial mentorship.
