Podcast Summary:

Becoming UnDone – Ep. 149 | Caught in the Spotlight: Secrets of a Celebrity Business Manager with Jonathan Schwartz
Host: Dr. Toby Brooks
Guest: Jonathan Schwartz
Date: February 14, 2026

Episode Overview

In this raw and revealing episode, Dr. Toby Brooks sits down with Jonathan Schwartz, once a top entertainment business manager entrenched in the world of celebrities and fortune. Schwartz shares how his high-flying career quietly unraveled due to a relentless gambling and substance addiction, ultimately leading to embezzlement, public disgrace, federal prison, and the slow process of rebuilding. The conversation goes far beyond a true crime narrative, delving into addiction’s psychology, shame, humility, and the painstaking journey of reassembling a meaningful life after catastrophic failure.

Key Discussion Points & Insights

1. Origins and Career Ascent

• Early Aspirations and Family Influence
  • Schwartz grew up dreaming of playing major league baseball but, with seven CPAs in the family, found himself inevitably drawn to accounting.

    “I knew I was destined to be a CPA… and in particular as an entertainment business manager because one of those cousins was in the music business and asked me to come work for him.” (05:42)

• Entering the Entertainment World
  • Started at the bottom to avoid nepotism: first in, last out, absorbing everything about the business.

    “I read those files from page one to the last page and I just was a sponge. And that's what I needed to be…” (07:00)

• Breakthrough with High-Profile Clients
  • Landed Linkin Park as clients at the dawn of their career, opening connections to other major acts including Alanis Morissette.

    “Once the outer world saw the success that Linkin Park was having… lawyers, agents, and managers, they started calling me…” (11:02)

• The Unregulated Industry’s Trap
  • Brooks highlights the lack of licensure/accountability in the entertainment management world—a recipe for unchecked temptation.

    “Anyone with a business card and enough sales skill… can hold themselves out to be a business manager.” (08:27)

2. The Descent: Warning Signs, Addiction & Embezzlement

• Early Signs of Addiction
  • College: first forays into gambling resulted in major losses and foreshadowing of future betrayals.

    “We lost $10,000 in two weeks as bookies… I abandoned my fraternity brother, who was left to pay my share as well as his.” (11:02)

  • Repeated warnings: Multiple times covered by others for lost bets, each time ignoring the deeper issue.

    “Those two were major signals that maybe… I can become a compulsive gambler.” (14:45)

• Active Addiction and Rationalization
  • Rationalized “borrowing” from clients with grandiosity; everyday embezzlement justified by plans to win it back.

    “Borrowing in translation means stealing and embezzling. …unfortunately, that led to progressive illness, and that led to me gambling every day for six years.” (15:00)

• Dual Life and Emotional Collapse
  • Lived in hell, nights wracked with fear of exposure, layering cocaine use atop a spiraling existence.

    “I couldn't sleep… I didn't want to live. It became suicidal ideation. I defaulted to starting to use cocaine… putting up a facade that I was Superman. But deep down I was completely insecure and low self-esteem.” (19:51)

3. Exposure, Collapse, and Accountability

• The Moment of Being Caught
  • Alanis Morissette’s team discovers missing funds, triggering broad exposure of his theft and compulsion.

    “When we received the call… I said, you know what? Don’t do anything. Just give [the files] to him. That was my way of saying, I’m going to get caught and I want to get caught.” (24:26)

  • Schwartz recounts that being caught was, in retrospect, a critical turning point—and possibly life-saving.

    “If not getting caught, I probably would have followed through with my suicidal ideation… I’m glad I got caught.” (24:26)

• Legal and Personal Fallout
  • Restitution ordered; served 6 years federal prison, more than prosecutors sought.

    “A judge then handed down six years in federal prison and ordered Schwartz to pay more than $8.5 million in restitution.” (26:28)

• Owning the Harm
  • Schwartz refrains from excusing his behavior, emphasizing the need to face the pain caused and the importance of personal accountability.

    “I don’t make excuses. I don’t blame it on my childhood trauma… the truth is I own it.” (17:56)

4. Recovery, Prison, and the Path Forward

• Prison as Crucible for Change
  • Profoundly used prison time for self-reflection, worked AA 12-steps, and facilitated inmate programs.

    “I needed to go to prison. I needed time to remove some of my defects of character… and start to learn who I really want to become as my authentic self.” (22:52)

• Initial Resistance to True Recovery
  • Early rehab was motivated by hope for leniency rather than authentic desire, but gradually worked the program deeply through a sponsor.

    “I certainly didn’t go for the right reasons… but my sponsor probably saved my life.” (28:29)

  • Became a teacher and mentor inside:

    “I taught a victim impact program in prison to help inmates understand their poor choices had victims and to own it… I taught accounting…” (28:29)

• Rebuilding on the Outside
  • After prison, struggled with humility, working at Dunkin Donuts. Chose to retrain as a marriage/family therapist specializing in addiction.

    “I needed more humility… worked at Dunkin Donuts… ultimately, my higher power sent me a signal… get your KDAC… go to grad school and become a marriage and family therapist.” (32:04)

• Current Mission and Passion
  • Now helps others as a therapist and program director at Altus Rehab, leveraging lived experience for authentic connection.

    “This isn’t a job. It’s my passion. My life experience with addiction and trauma… almost immediately establishes a therapeutic alliance and rapport with the clients.” (45:22)

5. Lessons, Accountability & the Nature of Addiction

• Biggest Lessons and Advice
  • Don’t judge based on appearances; ask for help early; set boundaries; responsibility is shown in actions, not words.

    “I’m not going to earn back the trust of my loved ones through this mouth… the only opportunity I have is to continue to do the next right thing on a daily basis.” (33:22, 34:46)

• Addiction: Disease or Choice?
  • Both: Schwartz points to genetic predisposition and the critical role of personal responsibility for choices.

    “There's clinical evidence called multigenerational transmission… but at some point it becomes a choice… So I believe… it’s both.” (40:35)

• On Recovery and Systemic Challenges
  • Frustration with insurance-driven short rehab stays undermining long-term recovery; champions education, community care, ongoing support.

    “You’re setting up your insured to go to leave here prematurely when there’s still family sessions that need to be done… that’s what I’m very disappointed about within the recovery community, private insurance companies…” (37:57)

6. Memorable Quotes & Moments

• On Hitting Bottom
  • “I was living a double life… but deep down inside, I was completely insecure and low self-esteem… I wish I did have the courage to ask for help back then. Things would have been very different.” (19:51)
• On the Rebuild
  • “I wouldn't want [to take] a pill [that would make the addiction vanish], because I didn't take a pill. I took time to reflect on myself… I needed to go to prison.” (22:52)
• On Purpose
  • “This is not a job for me. I don’t have a job. This is my passion.” (41:07)
• Song for His Life
  • “Probably… ‘Lost’ by Linkin Park. …It just talks about how lost I was, how much I didn’t… I was putting up this facade.” (44:09)

7. Looking Forward

• What’s Left Unfinished
  • Earning back the trust of his children, supporting his mother through cancer, publishing a book, and using his story to inspire and educate others.

    “Still earning back the trust of one of my children. …coming out with my book that I believe will really help people, followed by… a Netflix series or a big screen feature film. …I want to give the same messages I’ve given you…” (47:26)

• Final Thought
  • “My name is Jonathan Schwartz and I am undone.” (48:17)

Notable Segment Timestamps

• Jonathan’s Embezzlement & Gambling Confession – 00:11, 15:00, 19:51
• Early Warning Signs of Addiction – 11:02, 14:45
• Discussion of Role and Industry Gaps – 07:00, 08:27
• On Being Caught and Aftermath – 24:26, 26:28
• Reflections on Prison & Recovery – 22:52, 28:29, 32:04
• Lessons on Accountability & Humility – 33:22, 34:46
• Systemic Challenges in Recovery Industry – 37:57
• Choosing a Song (Linkin Park’s “Lost”) – 44:09
• Closing Thoughts on Purpose & Next Steps – 47:26, 48:17

Tone & Language

The conversation is candid, honest, unvarnished, and at times blunt—reflecting both Schwartz’s CPA background (“tells it like it is”) and his years wrestling with shame, regret, and the difficult slog of true personal change. While Brooks occasionally steps back for clinical or empathetic commentary, the narrative foregrounds personal responsibility without seeking sympathy or absolution.

For Listeners Who Haven’t Heard the Episode

This episode offers a deep, inside look at how high achievement and access can mask profound vulnerability, how addiction distorts both morality and self-perception, and how collapse can become, with humility and work, the foundation for a radically different, more purposeful life. Jonathan Schwartz’s story is not one of instant redemption, but of daily, lived-at-the-bone accountability and service.

Connect with Jonathan Schwartz
Instagram: @therealjonathanschwartz (Professional account. Open for direct messages about addiction or seeking help.)