I Went to Bed a Millionaire and Woke Up $800K in Debt

Every founder loves talking about the win. Very few talk about what it actually cost to get there. In this episode of Tenacity with Sonia C, entrepreneur, investor, and bestselling author Ari Rastegar shares the stories most founders never tell. From borrowing $3,500 while still in law school to believing he'd become a millionaire overnight, only to wake up $800,000 in debt, Ari opens up about the failures that shaped how he builds businesses today. This conversation goes beyond startup success. Ari explains why failure isn't the opposite of winning, it's the process that makes great founders. He shares how unexpected setbacks taught him to prepare for uncertainty, why every entrepreneur should stress-test their business before a crisis hits, and how rebuilding his health became just as important as rebuilding his companies. If you're building a startup, navigating uncertainty, recovering from a setback, or questioning whether the grind is worth it, this episode offers practical lessons from someone who's lived through both the highs and the lows. In this episode, you'll learn: -Why failure is one of the greatest advantages a founder can have -How Ari went from a $3,500 loan to building a multi-billion-dollar real estate business -The startup mistake that turned a million-dollar win into an $800,000 loss -How to prepare your business for black swan events and unexpected crises -Why hustle alone isn't enough to build a sustainable company -The mindset shift that helped Ari rebuild both his business and his health -What resilience actually looks like when you're under pressure If you've ever wondered whether you're the only founder struggling behind the scenes, this conversation is for you.