Donate to the American Cancer Society:

https://www.facebook.com/donate/2452272278633311/

Sponsor the Next Episode:

CASHAPP - $TWIMH

🎧 This week, my headphones took me from one of the strangest true-crime stories in the news to some surprisingly powerful life advice—and a John Cena story that will make you think twice before taking a stranger’s drink!

🕵️ The Gypsy Rose Rabbit Hole: Ken Urker’s shocking death has reignited public interest in Gypsy Rose Blanchard. I walk through the complicated history, the latest reports, and the questions surrounding the case. Fair warning: I put on my tinfoil hat for a few minutes, but speculation is speculation, and the investigation is ongoing.

💪 LL Cool J on Becoming Better: What separates an amateur from a professional? Why do we give up when things get uncomfortable? And are we ever really too old to chase a dream? Two clips from LL Cool J offer a powerful reminder that growth doesn't have an expiration date.

🤮 John Cena’s Puke Burger: The WWE legend shares a wild, vulnerable story on What Now? with Trevor Noah that reminded me of one of my own spectacularly disgusting moments from my younger years.

🎙️ My Five Favorite Podcasts You Rarely Hear Me Talk About: Bad Friends, Brooke & Jeffrey in the Morning, How I Built This, Ray William Johnson: True Story, and 48 Hours.

Plus, a look at my week, my October fitness challenge supporting the American Cancer Society, and more from the 17 podcasts that made it into my headphones.

This isn't a podcast review show. I'm a truck driver who listens to a lot of podcasts, follows the stories that grab my attention, connects the dots, and shares the ideas and rabbit holes worth talking about.

💬 What have you been listening to lately? Send me your recommendations!

❤️ Support my 62 Miles in October fundraiser for the American Cancer Society: [INSERT FUNDRAISER LINK]

I'm Kevin T. Thanks for tuning in, and I'll see you next week in my headphones!

Support your favorite Content Directly!

Be a Sponsor of the Next Episode!CASHAPP - $TWIMHFollow me on Social Media - ⁠ https://bio.site/thisweekinmyheadphones

This week, I fell down a very deep rabbit hole.

It started with an episode of Diary of a CEO featuring WeWork co-founder Adam Neumann, and before I knew it, I was listening to podcasts, watching documentaries, digging through timelines, and trying to understand how a company once valued at $47 billion could unravel so spectacularly.

WeWork's story has everything: billion-dollar investments, massive ambition, questionable decisions, cult-like company culture, ego, financial chaos, and a founder who somehow managed to walk away with hundreds of millions of dollars while the company collapsed.

But the more I dug into the story, the more I became interested in something beyond WeWork itself: the relationship between the visionary and the voice of reason.

Adam Neumann was the big dreamer. Co-founder Miguel McKelvey was the grounded builder. Together, they seemed to make an incredible team—until they didn't.

And honestly, I recognized a little bit of myself in both of them.

I'll also revisit a clip from Rick Rubin about AI and creativity, where he makes the argument that "the creativity is in the prompt." My take? AI can be the storyboard, but you're still responsible for making the movie.

So this episode is part WeWork deep dive, part business lesson, part personal reflection—and, as usual, a collection of things I've been thinking about after spending way too much time listening and researching.

Welcome to This Week In My Headphones.

Thank you for your donations!

CASHAPP - $TWIMH

Follow me on Social Media - This Week In My Headphones — Bio Sites

This Week In My Headphones, I’m going in a LOT of different directions—but somehow, they all seem to lead back to the same question:

Who are you really, and what are you supposed to do with your life?

After listening to 36 podcasts over the last two weeks, I found myself coming back to a few big themes: wisdom, authenticity, creativity, happiness, failure, purpose, and betting on yourself.

I dig into conversations with Steven Bartlett, Arthur Brooks, Grayson Hart, Rick Rubin, and Druski, including ideas about the path to wisdom, being “ruthlessly authentic,” finding true happiness, and what it means to actually invest in yourself.

I also talk about upgrading my studio, getting onto more podcast platforms, experimenting with YouTube, investing money and time into myself, and why I’m choosing to build this thing before I have sponsors, advertisers, or even monetization.

🎧 This Week In My Headphones is my weekly deep dive into the podcasts, conversations, ideas, stories, and rabbit holes that made me stop, think, laugh, question something, or want to learn more.

If something in this episode makes you think, “Wait… I want to know more about that,” then I’m doing this right.

👍 Like the episode
🔔 Follow/subscribe and turn on notifications
📲 Follow me on social media for exclusive content and clips
💬 Tell me what YOU have been listening to
📤 Share this episode with someone who might enjoy it

And if you want to support the show directly, you can find my Cash App information on screen/in the episode.

Thanks for listening.

— Kevin T.
This Week In My Headphones

___________________________________________________

Full Podcast List

The Tim Dillon Show - #512 & #513

The Diary of a CEO with Steven Bartlett –

• Professor Jiang:Three Predictions On the Collapse of the World Order

• Rick Rubin: WhatJay-Z Did in 30 Minutes Left Me Speechless!

• Druski: They’reLying to You About Overnight Success!

Bad Friends –

• Bobby’s Moana Birthday! w/ Stavros Halkias

• Trash Rummaging with Rudy

Huberman Lab –

• The Art of True Happiness | Dr. Arthur Brooks

• Best Tools for Gut Health & Weight Loss |Dr. Chris Thompson

• Essentials: Optimal Protocols to BuildStrength & Grow Muscles | Dr. Andy Galpin

The President’s Daily Brief – September 14th,2026: China Helped Iran Carry Out Strike That Killed 3 U.S. Troops & Russian Drone Strikes Near Poland

2 Bears, 1Cave with Tom Segura & Bert Kreischer – WhatPercent Gay Are You?

The Ben Shapiro Show – Ep. 2506 – Everything You Need ToKnow About The AI Wars

Brooke and Jeffrey –

(9/14/26), (9/15/26), (9/21/26), (9/22/26), (9/23/26)

The Joe Rogan Experience -

• #2553 – Andrew Huberman

• #2527 – MrBeast

• #2554 – Carlo Rovelli

• #2555 – Ron White

• #2556 – Siddharth Kara

All-In with Chamath, Jason, Sacks & Friedberg –

• -Jensen Huang: The Doomer Hoax, Superintelligence Is Here, and The Future of AI (ft. President Tump)

• -Neveen Rao: 4D Computing, AI’s Energy Wall & Beating Biology

• -Luca Ferrari, Bending Spoons CEO: The $40K Origin Story, Buying Product-Market Fit & Why Private Equity Can’t Compete

Kill Tony -

• #785 – Duncan Trussell + Kurt Metzger

• #786 – Donnell Rawlings + Sam Tallent

Sexual Assault Survivor Stories Podcast – SASS -

• #173. Beth: When “Normal” was Actually Rape and Sexual Assault

• #206. Cat Wilson: Unapologetic, Unafraid, and Finally Heard

You Choose with Billy Garton Jr. –

• The Art of Being Ruthlessly Authentic – Grayson Hart - #023

• The 3 Rules for Getting Everything You Want – Koa Smith - #022

The Francesca Psychology Podcast – Harvard’s happinessExpert: Why You Lack Meaning (And 6 Ways To Find It) – Arthur Brooks

Lex Fridman Podcast - #502 – Psychiatry, Insane Asylums,Mental Illness, ECT, Lobotomies, Freud & Jung

Modern Wisdom – The New Way For Ordinary People To BuildWealth – Tony Robbins - #1153

What Now? With Trevor Noah – Jimmy Carr: My Mom’s DepressionMade Me Funny