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
