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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
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