You Made It Weird with Pete Holmes – Episode Summary

Episode: Chad Goes Deep (Tom Allen)

Date: March 26, 2025
Guests: Tom Allen (aka "Chad" from Chad & JT Go Deep)
Host: Pete Holmes

Overview

This episode of You Made It Weird features Tom Allen, best known as "Chad" from the YouTube and Netflix comedy duo Chad & JT Go Deep. Pete and Tom dive into Tom’s comedic persona, his family and upbringing, boarding school culture shocks, personal and professional insecurities, playfulness in comedy, spiritual practices, and psychedelic experiences. The conversation is candid, playful, and philosophical, with heartfelt detours into self-acceptance, existential anxieties, and finding one's true self both on stage and in life.

Key Discussion Points

1. Tom Allen’s Comedy Roots & Family Background

• Tom’s Upbringing & Family Expectations:
  • Raised in a high-achieving family—dad was a doctor, siblings in finance and attended prestigious schools.
  • Felt like a “secret goof” in a family that valued traditional success.
  • “I always kind of felt a little bit kind of in real life, that kind of scared to be myself a little bit when I was younger…” (09:07)
• Comedy as Self-Expression:
  • Found playfulness and his “real self” through stand-up and developing the Chad persona.
  • Got the “green light” from his father to pursue acting/comedy at age 21 after resisting more conventional career paths.
  • “He’s actually the reason I...just went like hard, full steam.” (28:55)

2. The Boarding School & Culture Shock Experience

• Transition from California to East Coast Boarding School:
  • Attended Hotchkiss after siblings; describes boarding school as highly competitive and a cultural shock from laid-back California.
  • “First guy I met...he’s like, ‘I want to manage a hedge fund.’ You know, we’re like 14.” (16:51)
  • Felt an increased pressure to fit in, leading to party culture and a search for identity.

3. Fitting In, Insecurity, and Playful Rebellion

• Openly discusses experimenting with drugs at boarding school, not for substance’s sake but as a way to find confidence and expression.
• Felt partying allowed him to “be himself a little bit,” a preview of how comedy would later become his primary outlet.
• Parallels between the rush of performing and the thrill (and social container) of party culture.

4. The Role of Naivete and Fearlessness in Creative Pursuits

• Both Pete and Tom discuss the “necessary naivete” to pursue comedy, echoing Anthony Jeselnik:
  • “You need like a large amount of naivete to go into comedy.” (13:24)
• The importance of playfulness and not worrying about long-term outcomes:
  • “There’s what I do, and I love what I do...But when you see people just playing and being purely silly…there’s something quietly inspiring.” (07:52)
  • Pete praises Tom’s work: “It’s like somebody woke up completely unafraid.” (08:08)

5. Spirituality, Non-Duality, and Personal Practice

• Deep dive into non-duality and spiritual inquiry, citing Eckhart Tolle, Rupert Spira, and experiences with psychedelics.
• Tom and Pete discuss the blend of Eastern wisdom (Vedanta/Advaita), the “playful, fearless” mindset, and living in the present:
  • “[Spirituality is] wanting to reach a place where you just always feel playful and secure, knowing who you really are is awareness and nothing can really hurt you.” (46:22)
• Gratefulness practice:
  • “The real thing is to say thank you for everything. I’ve been doing it. I’ve been, like, really stressed, and I’m just trying to be like, thank you.” (61:01)

6. Ego, Achievement, and Letting Go

• Open exploration of deep-seated anxieties about worth and the pressure to "kill it" in comedy:
  • “My biggest fear...I’m worthless.” (67:05)
• The role of inherited family values in shaping personal ambition.
• The realization that self-worth can't only be tied to traditional success or outside recognition.

7. Psychedelics, Death, and Consciousness

• Pete shares experiences with 5-MeO-DMT and ketamine, likening them to ego death and merging with awareness.
• Both relate these experiences to non-dual philosophies—“You don't go anywhere. There's nowhere to go. You can't move an inch away from source...” (77:39)
• Discussion of near-death experiences and the comfort found in merging stories from “the other side” with spiritual teachings.

8. Art, Joy, and “Fight Club”

• The importance of following one’s unique “triangle” (per Conan O’Brien): keep doing your distinct thing amidst the noise.
• Tom’s approach to his comedy videos: “following joy” and not just chasing what the industry expects.
• Validation through play and first-hand “feedback” in art and life.

Notable Quotes & Memorable Moments

• On Playfulness & Comedy:
  “It’s not only funny, but there’s something kind of quietly inspiring, like, why am I so tight?” – Pete Holmes (08:48)
• On Living Out Loud:
  "You woke up and realized the infinite potential of reality—and went at it without feeling fear." – Pete Holmes (08:32)
• On Spiritual Playfulness:
  “One of the indicators of knowing your true nature is a certain playfulness and a certain fearlessness.” – Pete Holmes (47:56)
• On Death & Awareness:
  “You don't go anywhere. There's nowhere to go. You can't move an inch away from source, God, being, knowing, consciousness. It's what you are.” – Pete Holmes (77:39)
• On Life's Challenges:
  “Your tax problems are a tiger chasing its food. And it’s like the happiest it’s ever been.” – Pete Holmes (63:06)
• On Marriage & Partnership:
  “Respect is a great avenue of love... putting your thing over here because you respect that they want that week to do that thing.” – Pete Holmes (129:16)

Timestamps for Key Segments

• [03:41 – 13:24] Family background; Boarding school and the California vs. East Coast divide; Pressure to follow conventional paths.
• [16:51 – 23:40] Culture shock at boarding school; Partying, experimenting; Realities behind “professional” careers.
• [34:03 – 43:55] Playfulness, comedy as identity; Open mics as “fight club”; Finding real competitive drive through comedy.
• [43:55 – 55:36] Existential anxieties before performing; Spiritual practice, non-duality, and fearlessness; Eckhart Tolle anecdotes.
• [61:01 – 67:05] Gratefulness practice, real-world stressors, therapy, and inherited ego.
• [77:06 – 87:58] What happens after death; Psychedelics, direct wisdom, near-death experiences.
• [108:17 – 111:55] Art and career: Forcing vs. flowing, following joy; Conan's advice about triangles; The origins of Tom’s Fast & Furious in-public bit.
• [124:14 – 126:52] Hardest laughs: Starship Troopers, dorm buddy mishap; Classic dorm humor.
• [127:02 – 129:55] Marriage, respect, and the surprise of deep partnership; Allowing space for feelings.

Additional Highlights

• Comedy in Character vs. Authenticity:
  Tom reflects on the paradox that playing a character (Chad) lets his real self shine.
• Culture & Success:
  Both discuss the difference between being happy vs. being “better than your enemies”—insight into American social dynamics. (113:03)
• Psychedelics as Death Rehearsal:
  Pete likens ketamine and DMT experiences to “dress rehearsals” for dying, returning always to the essential experience of being.
• Advice for Creatives:
  Echoing Conan, Tom, and Pete agree: keep hitting your triangle—consistency and authenticity will eventually cut through the noise.
• Anecdotal Gold:
  Tom’s hardest laugh? Watching Starship Troopers stoned in college and a dorm incident with shaved eyebrows.

Tone & Final Takeaway

The conversation sails between funny, weird, vulnerable, and philosophical, peppered with moments of stoner giggles and deep dives into why humans fear, love, and strive. Both Pete and Tom advocate for play, presence, and acceptance—on stage, in art, and in life. The episode is a candid celebration of weirdness, spiritual curiosity, and living authentically, “completely unafraid.”

Classic Sign-Off

Tom Allen: “Keep it crispy.” (131:49)
Pete Holmes: “Because when the wave tosses you down—just surrender, you cruise. Just cruise, man... that was the word we were looking for, and you got it.” (131:50)