Podcast Summary:

Miss Understood with Rachel Uchitel

Episode: The Bad Boy of Wall Street: Going Public with Ross Mandell

Release Date: February 3, 2026

Episode Overview

This episode features a powerful conversation between host Rachel Uchitel and Ross Mandell, the notorious Wall Street power player whose career rise and fall embodied the excess, personality, and controversy of 1980s and ‘90s finance. Mandell—once convicted in a massive brokerage fraud case—joins to discuss his personal story, challenge the public narrative around his criminal case, and reflect on reinvention and resilience in the face of public infamy.

Rachel seeks to go beneath the headlines, exploring questions of accountability, system blame, and whether someone so identified with scandal truly deserves a second act.

Key Discussion Points & Insights

Ross Mandell’s Early Life & Upbringing

• Family & Childhood Influence
  • Mandell describes a loving, upper-middle-class upbringing on Long Island, motivated by his mother’s aspirations ("my mother used to drive us around neighborhoods and say, this is where this one, he's in the diamond business, he's worth millions...she instilled that in my mind" 05:00).
  • A stellar student and athlete, aiming for medicine until tragedy struck.
• Loss of Father & Downward Spiral
  • At 16, Mandell’s father died suddenly: "I was 16. I reacted very badly...He was my North Star." (05:55)
  • Turned to drugs and alcohol to numb pain, admitting he "stayed stoned for 17 straight years" [09:03].
  • Shifted social circles after trauma, gravitating toward "kids that were generally from broken homes or messed up" (11:36).

Becoming a Wall Street Power Player

• Early Hustle & Entry to Wall Street
  • Started out organizing lucrative parties in college, always focused on hustling and opportunity (16:00–17:20).
  • Transitioned to finance via the E.F. Hutton training program, despite a nontraditional background: “The other 11 people were lawyers, accountants and MBAs. And me, handbag salesman. But I, you know, I talked my way in because I'm a good communicator" (19:21).
• Describing the Culture
  • High-energy, hard-partying, “work hard, play hard” mentality (27:13): "A lot of those boys on the street, they work hard, they play hard...I would go out, I'd work my ass off if they told me I had to make 300 phone calls a day. I made 350. I made four. I've always been that worker."

How Legitimate Ambition Turns Questionable

• Salesmanship and Relationship Building
  • "I was a really, really good trader...I've created more Wall Street millionaires than anybody else" (26:09).
  • Emphasized the importance of genuinely liking people: "A lot of guys become successful, they don't really like people. I really love people." (21:44)
• Parallel to “Wolf of Wall Street”
  • Admits his environment was similar—"Very similar. Just like that and Boiler Room, correct? 100%." (25:23)
• How the Line Gets Crossed
  • Differentiates himself from obvious frauds but acknowledges brokers under him committed wrongdoing, unbeknownst to him (47:15): "There were four or five guys, brokers out of...thousands of employees...that were cheating customers...If Ross Mandel knew what we were doing, he would throw us to the curb. I would."

The Sky Capital Case & Legal Controversies

• Mandell’s Version of Events
  • Claims his prosecution was a byproduct of lawfare and scapegoating after big bank failures: "The government wanted to use me. They actually told the jury I'm the reason they all lost their jobs, I'm the reason for the mortgage crisis" (13:19, 46:22).
  • Mandell took a regulated American company public in London—first to do so in 350 years (35:57): "I'm the first American to take a regulated American company...put it on the London Stock Exchange."
  • Asserts the system protected insiders: "I fought them. Huge mistake. Because that's the way it is. I hate to say it." (50:31)
  • No lawsuits against him, unlike Belfort: “You know how many lawsuits I have? Zero. Not one single person suing me...the only people who want to take my money, the government." (53:07)
• Government Pressure & Missed Exit
  • Describes being offered $300 million to walk away by Bob Diamond, CEO of Barclays, which he refused: "We're offering you a chance to walk away...I didn't accept it. And that was a mistake. Because at some levels, you got to play ball." (46:22)
  • Government ultimately seized significant assets: "The government took $65 million from me. Cost me $150 million at least. Because they created the crime." (29:30)
• Systemic Critique & Parallels to Politics
  • Frequently draws attention to high-profile cases and government manipulation, e.g., Donald Trump: "Now we have a 78 year old ex president...charged with 92 counts...People understand now how dirty the Department of Justice is and the government." (13:19–15:28)

Reinvention & Life After Prison

• Release and Rebuilding
  • Served over nine years in prison, now returned as a media personality: "My podcast just broke the top 50 on Apple. It's really amazing." (26:55)
• Coaching, Mentoring, and Social Media
  • Coaches others, hosts a mastermind group, particularly interested in empowering women: "I'm mentoring several women now. I find women to be so much more brilliant than men...just women lack confidence in themselves." (38:38–39:17)
  • Reflects on authenticity, both as a new personal goal and what social media users crave: "People are looking for authentic people...all these guys that are really big and successful at social media, they've never actually done anything." (56:25)
• Not Barred
  • Not prohibited from working in finance per se but chooses not to return: "I'm barred from nothing. No one ever heard of anything like this...but I can't become registered, and I would never want to be registered ever again." (55:04)

Notable Quotes & Memorable Moments

• "I stayed stoned for 17 straight years." — Ross Mandell [09:03]
• “The government wanted to use me? They actually told the jury, I'm the reason they all lost their jobs, I'm the reason for the mortgage crisis.” — Ross Mandell [00:59]
• "I created a footprint, a blueprint. Never been done before...And Goldman Sachs came at me...I couldn't get an interview with Goldman Sachs when I was a stockbroker." — Mandell [43:11]
• "We're offering you a chance to walk away." — Bob Diamond (as recounted by Mandell) [46:22]
• "You show me a guy that made it and lost it, I'll show you a guy that's gonna make it again. This is Ross 3.0 you're getting." — Ross Mandell [29:23]
• “If there was social media in the 80s and 90s, I would have been a Kardashian, probably.” — Ross Mandell [30:52]
• “No one ever heard of anything like this… but I can’t become registered, and I would never want to be registered ever again.” — Ross Mandell [55:04]
• "[Prison]...I did nine years and four months while I was in the system. They said I owed no money, but a $10,000 fine because I was very rude in court." — Ross Mandell [53:21]
• “Life is an experience from birth to death. You're not guaranteed another minute...be you. Don’t pretend, don’t act, don’t think you gotta be somebody you’re not." — Ross Mandell [58:01]

Timestamps for Important Segments

• Introductions & Public Narrative: 00:30–03:56
• Ross' Early Life & Family: 04:06–09:49
• Downward Spiral & Loss: 09:50–13:19
• Discussion of Government Targeting & Wall Street Culture: 13:19–21:59
• Rise on Wall Street: 22:00–29:00
• Sky Capital, Going Public, and Disruption: 35:57–46:22
• Government Pressure, Missed Exit with Barclays: 46:22–50:31
• Legal Case, Prison, and Aftermath: 50:31–55:17
• Reinvention, Coaching, and Closing Thoughts: 55:17–58:35
• Final Takeaway on Authenticity: 58:01

Overall Tone & Language

The conversation is candid, irreverent, and unapologetically brash—much like Mandell himself. Rachel brings curiosity and a willingness to challenge, while Mandell mixes bravado with flashes of humility, casting himself as both disruptor and misunderstood victim of larger forces.

Final Reflections

Mandell’s story embodies the complex grey area between ambition, hustle, and ethical lines—a saga of success, excess, prosecution, and a new digital-era redemption. Rachel Uchitel’s probing, empathetic style offers listeners a rare window into the mind of a headline-making, self-described “disruptor” eager to reclaim his narrative.

[Note: All ad/promo/read sections omitted as per instruction. Timestamps reflect core content only.]