20 Year Timeout

20 Year Timeout is a podcast about rediscovery of people, memories, and the twists life takes.

Each episode, I reconnect with someone I lost touch with sometimes 20 years ago, sometimes just last week. A childhood friend, an old bandmate, someone who quietly disappeared from your life. We pick up the thread, press unpause, and see where the story goes.

It’s unscripted, funny, reflective, and full of unexpected insight. If you’ve ever wondered what happened to that person and what reconnecting can reveal about creativity, culture, and who we’ve become, hit play.

🎙️ Real conversations. Imperfect memories. Honest reconnections.

Podcasting since 2025 • 19 episodes

20 Year Timeout

Latest Episodes

Two Unmedicated ADHD Guys Get Out Of Hand— Comedy, Filmmaking & 20 Years of Stories

In first grade, Tommy Jay Dwyer was asked to draw God. While every other kid drew a wizard with a beard and a staff, Tommy drew a red box. The teacher held it up in front of the class, called him to the front, and told him he was wrong....

May 27, 2026 • Episode 18 • 1:34:01

He Saved Every Pill Bottle for 15 Years — What He Built With Them Is Unforgettable

For 15 years, Frank saved every single pill bottle.He didn't know why. Through his divorce, through the worst years of his addiction to Oxycontin and Methadone, through watching his entire family wilting away — he kept throwing the bott...

May 12, 2026 • Episode 17 • 1:07:15

Is Claude AI Actually Conscious? I Put It on the Podcast

Is Claude AI actually conscious? Does it have feelings? Would it marry ChatGPT?This week on 20-Year Timeout, Rich Marks flips the script. Instead of reconnecting with a long-lost friend, he sits down with Claude — the AI from Anthropic ...

May 04, 2026 • Episode 16 • 58:47

His Roommate Left Him With a Caved-In Skull — Now He Builds Sound Healing Machines

Brendan Casey and I went to school together back in Worcester. I knew bits and pieces of what happened to him. I wasn't ready for the full story.In January 2020, Brendan was attacked in his own kitchen by a roommate hiding ...

April 27, 2026 • Episode 15 • 1:13:28

15 Years in Insurance, Now Building Contractor Guy Network — Here's Why

Zach Nehme and I worked together at the Old Pink House in Savannah — the guy who could walk into a private dining room, work the whole table in ten minutes, and be gone before you even noticed he was there. Then life happened. 15 years in comme...

April 20, 2026 • Episode 14 • 1:22:17

See All Episodes