Podcast Summary
Keeping It Real: Conversations with Jillian Michaels
Episode: UNCANCELLABLE: Tom MacDonald on Freedom, Fear, and Fame
Date: December 28, 2025

Episode Overview

In this dynamic interview, Jillian Michaels sits down with Tom MacDonald, the polarizing independent artist often described as “the establishment loves to hate and the people refuse to ignore.” They delve into Tom’s journey from pro wrestling and personal crises to using music as a vehicle for social commentary—unfiltered by label or industry expectations. The discussion explores the meaning of freedom, the trauma and transformation of addiction, the culture wars roiling America and beyond, and what it truly means to be “uncancellable.” The episode is rich in real talk on fear, mental health, the manipulation of media, resilience, and what it means to stand up for one’s truth in a world eager to shut you down.

Key Discussion Points & Insights

Tom’s Unlikely Path: From Wrestling to Political Rap

• Pro wrestling was Tom’s first dream—a career cut short by mounting injuries and backstage politics ([02:47]–[03:44]).
  • “It’s extremely political... You wouldn’t know it unless you were in the wrestling business... it just took a toll on my body. So I just kind of...” – Tom MacDonald (03:25)
• Creativity from a young age—poetry, songwriting and inspiration from his grandfather, a “super patriotic Canadian” fascinated with American and world politics ([04:08]–[06:47]).
• Merging art and commentary happened organically after wrestling—he never envisioned becoming a culture-shaping artist or political force ([06:47]–[06:47]).

The Crisis that Changed Everything: Addiction and Mental Health

• Tom describes a devastating mental breakdown after years of partying, addiction, and personal disarray ([14:10]–[24:17]).
  • “My life is divided by that moment. My entire life is pre mental breakdown and post mental breakdown.” – Tom MacDonald (14:11)
• Harrowing details: Panic attack, feeling unrecognizable, being rescued by family, and a broken mental healthcare system ([16:49]–[23:05]).
• On the importance and pitfalls of medication: Used Ativan to bridge the crisis, recognizing both its necessity and its risks ([23:05]–[24:47]).
• Recovery: Total lifestyle overhaul—quitting substance use, improving diet, exercise, therapy, and the role of personal research in rebuilding his life ([25:32]–[27:38]).

Nova, Partnership & Poverty

• Nova Rockefeller, Tom’s partner, was integral to his artistic rebirth. Their early years in LA were marked by extreme poverty and resourcefulness ([27:11]–[30:16]).
  • “We did all of our shopping at the 99 cent store... there was times we couldn’t afford our utilities and groceries at the same time.” – Tom MacDonald (29:16)
• Nova’s support extended from personal to professional—she helped launch Tom’s independent music business ([67:02]–[67:03]).

“Dear Rappers”—The Turning Point

• Sparked by frustration over mainstream rap’s inauthenticity, “Dear Rappers” was written in a single, inspired burst (“It was like God looked down at me that day and was like, you know what, kid? I’m gonna give you a shot.” [35:32]).
• Resourcefulness: Raising $1,100 from family and friends for a single social media campaign—payoff came with 1.2 million views overnight ([37:24]–[38:36]).

Speaking Out: Culture War, Media Manipulation & Being “Uncancellable”

• Tom critiques both mainstream media and pop culture as tools for social engineering and control ([01:20]–[01:32]; [54:31]–[55:49]):
  • “They use the news to control adults and they use pop culture to control kids... There has to be some sort of connection there.” – Tom MacDonald (20:13)
• He positions himself as a voice “for everyone tired of being lectured about race, gender, and politics by a system designed to divide us” ([01:03]).
• Experiences being labeled with every pejorative—racist, transphobic, Zionist, fascist, etc.—by both left and right ([57:24]–[58:11]).

Art, Authenticity, and Responsibility

• Tom reflects on his journey from imitating rappers to using his own voice: moving from writing about “cars and girls” to tackling polarizing issues, always striving to be genuine ([43:34]–[44:45]).
  • “I just wanted to make music about shit that I really cared about.” – Tom MacDonald (44:49)
• He stresses the importance of not perpetuating cycles of self-destruction through his art—and the burden of being misunderstood ([44:49]–[48:41]).

Independence, Entrepreneurship, and Outworking the System

• Tom’s formula for “uncancellability”: Build your own ecosystem, never rely on gatekeepers, reinvest relentlessly, outwork everyone ([65:45]–[70:35]).
  • “Anything the system can offer you, you can do it yourself. It’s a longer road, it’s a harder road. But...if you are not afraid of hard work, you can…be successful.” – Tom MacDonald (69:46)
• On record labels: Describes their limitations and why he currently avoids signing other artists ([70:42]–[74:06]).

Safety, Fear, and Freedom in the Public Arena

• The consequences of being such a polarizing figure: Security threats cast a shadow over touring, and balancing courage with caution is a constant struggle ([80:18]–[85:07]).
  • “There comes a point where we can only do so much... I have to be able to live my life as well.” – Tom MacDonald (82:08)

Passing the Torch: Actionable Wisdom for Listeners

• Tom’s advice for those struggling: There’s no perfect formula, but resilience, hard work, and self-reliance are crucial ([64:32]–[65:19]).
• Community and family—keeping a tight circle helps maintain stability (“I have four dogs, a wonderful girlfriend, and a couple friends... That’s my circle.” [67:03]).

Notable Quotes & Memorable Moments

• On addiction and mental health:
  • “My life is divided by that moment. My entire life is pre mental breakdown and post mental breakdown.” ([14:11])
  • “If you don’t know where the fire started, you will surely burn in it.” ([14:33])
• On mainstream controversy:
  • “I can’t be canceled, there’s no way you can stop me. Fully independent, there’s no label who can drop me.” – Tom MacDonald (Opening performance, [00:08])
  • “There’s not a racist lyric in the entire song. They’re actually the exact opposite.” – Jillian Michaels, on “Dear Rappers” ([50:11])
• On freedom of speech and labels:
  • “So I’ve been called everything... racist, transphobic, homophobic, white supremacist, Nazi, Zionist, fucking Zionist.” – Tom MacDonald ([57:41])
• On dealing with fear:
  • “Fear is a strong vibration…You let a little bit of it in, it multiplies and it grows, and there’s a flood that occurs after it.” – Tom MacDonald ([83:46])
• On independence:
  • “If I want to be successful in this field...how do I create my own ecosystem?” ([65:45])
  • “No sponsor is going to drop us. There’s nobody that’s going to tell us, ‘No, you can’t release that.’ Let’s just do it our way.” ([67:02])
• Music as therapy and action:
  • “I usually can’t have a conversation about those things, but I can decipher enough to write a song about it.” ([92:12])
• On resilience:
  • “Anything that the system can offer you, you can do it yourself. It’s a longer road. It’s a harder road.” ([69:46])

Timestamps for Important Segments

• Opening & Performative Verse – [00:02]–[00:33]
• Childhood & Political Upbringing – [04:08]–[06:47]
• Addiction, Breakdown & Recovery – [14:10]–[27:38]
• Dear Rappers: Inspiration & Launch – [32:34]–[38:36]
• Music, Responsibility, and Outrage Culture – [43:34]–[48:41]
• Media Manipulation & Culture Control – [54:31]–[56:22]
• Being Uncancellable & Culture War Fallout – [57:24]–[62:44]
• Advice for Struggling Youth – [63:54]–[65:19]
• The Business of Independence – [65:45]–[70:35]
• Security & Touring Fears – [80:18]–[85:07]
• Fan Q&A w/ Phoenix – [87:13]–[97:57]

Phoenix’s Fan Q&A (with Timestamps):

• Favorite song written & why:

  • “Dear Rappers” — the turning point.
  • “Ghost” — a love song for Nova, first pop success.
  • “You Missed” — written after the Trump assassination attempt, capturing raw, current emotion. ([88:21]–[94:24])

• Favorite song of all time:

  • “Going to California” by Led Zeppelin.
  • Meaningful because of lines about chasing dreams and the American journey, reminds Tom of his family and the risks he took. ([94:33]–[96:52])

• Favorite tattoo:

  • The one on his stomach: “If you don’t know where the fire started, you will surely burn in it.” Symbolizes surviving chaos. ([96:53]–[97:37])

Where to Find Tom MacDonald

• Music: All major streaming platforms for singles. Full albums on CD/USB only at hangovergang.com ([98:43]).
• Tom is fully independent—purchasing directly supports him without intermediaries.

Tone and Takeaways

The episode is raw, honest, and at times vulnerable—a testament to Jillian Michaels’ interviewing style and Tom’s commitment to authenticity. Their conversation navigates trauma, controversy, and cultural fracturing without losing sight of hope and resilience. Listeners walk away with a deeper understanding of both the danger and the necessity of speaking your truth—especially when the “brand is me.” Tom’s story is a blueprint for carving out independence, facing fear, and defining your own success outside the boundaries set by institutions.

For more on Tom MacDonald and his message of resilience, independence, and truth-telling, visit hangovergang.com.

“You don't craft a messenger with cotton candy. Anybody who is going to be that voice has to go through hell, or people don't identify.”
– Jillian Michaels ([39:46])