Ross Mandell: From $1,500 to $30 Million, Prison & The Untold Story of Wall Street's Most Feared Trader.

Tell us what you like or dislike about this episode!! Be honest, we don't bite! In this brutally honest episode, Matt Haycox sits down with Ross Mandel, a former Wall Street high-flyer who went from building a $30M empire to serving time behind bars. This isn’t just a story about money. It’s about power, addiction, ego, and redemption. Ross opens up about how a “normal” childhood spiralled into a life driven by money, fuelled by personal tragedy, and eventually cracked wide open by government scrutiny. He shares what it was really like inside Wall Street’s golden age, how fortunes were made (and lost), how client relationships shaped everything, and what no one tells you about the financial system. From shady legal grey areas to personal run-ins with Donald Trump, Ross doesn’t hold back. He talks openly about prison life, the brutal truth of starting over, and how he rebuilt his mindset through mentoring others on the inside. Now? He measures success through his daughters, not a bank balance. If you’ve ever glamorised Wall Street, this episode is your reality check. Timestamps: 00:00: Introduction to Ross Mandel"s Journey 06:50: Chasing Money and Lifestyle 12:21: The Rise to Success 21:20: Navigating Market Conditions 26:27: Turning $1,500 into $30 Million 42:09: The Birth of Sky Capital 47:10: The Power of Imitation in Wealth Creation 54:03: Surviving the Financial Crisis 01:01:29: The Flaws in Rating Agencies 01:10:39: Personal Experiences with Donald Trump 01:23:30: Life in Prison and Its Challenges 01:31:03: Teaching and Learning in Prison 01:39:48: Safety and Leadership in Prison 01:46:02: Rebuilding Life After Prison __________________________________________________________________________________________ Welcome to Stripping Off with Matt Haycox This isn’t your average business podcast. It’s where real entrepreneurs, celebs, and industry leaders strip back the polished PR, and get brutally honest about the journeys that made them. Hosted by entrepreneur and investor Matt Haycox, Stripping Off dives into the raw, unfiltered realities behind success: the wins, the fuck-ups, the breakthroughs, and everything in between. No scripts. No sugar-coating. Just real talk from people who’ve lived it. Whether you’re hustling to scale your business or just love a behind-the-scenes look at how people really make it, this podcast is your front-row seat to the truth behind the triumphs. Who Is Matt Haycox? - Click for BADASS Trailer