Reconnecting With My First Best Friend After 30 Years | EP 4 20-Year Timeout

There are conversations that take you back in time, and then there are conversations that erase time completely. Episode 4 of the 20 Year Time Out Podcast did exactly that for me.

Billy was not just a guest. He was my first best friend ever. Long before high school, long before social media, long before adult life, Billy and I were two kids figuring out the world, bonding over Mortal Kombat, dirt bikes, iguanas, and whatever chaos kindergarteners could get into.

This blog post expands on the episode and tells the story behind the mic. If you ever had a friend from childhood who shaped your early world, this one is for you.

Let’s dive in.

1. The First Guest From My Pre High School Life

Every guest I have had on the podcast so far was someone I reconnected with from high school or later. Billy was the first guest from before all of that.
Grammar school level.
Saint Mary’s level.
“Can two kindergarteners even ask their parents for sleepovers?” level.

When I hit record, I realized how wild that distance really was.
The last time we hung out, we were practically babies.

Yet somehow, the connection was still there. Completely intact.

2. Kindergarten Sleepovers, Iguanas, and Mortal Kombat

This episode turned into a time machine immediately.

We talked about:

His iguana named Speedy Harley
Swimming at his old apartment’s pool
The basement with the TV on the floor
The hot box (if you know, you know)
Prank calls inspired by the Jerky Boys
Chat rooms we had no business being in at ten years old

Every memory had the same vibe:
two kids having the time of their lives with no idea that they were building lifelong core memories.

What amazed me was how vivid these moments still were for both of us.

3. Growing Up, Growing Apart, and Growing Into Different Lives

Billy moved to Auburn in second grade, and that was it.
Life split.
Different schools.
Different friends.
Different paths.

On the podcast we talked about that transition and how rough it can be for a kid. One day you have your crew. The next day you are the new kid trying to make sense of everything.

But he adapted.
Sports helped.
Martial arts helped.
And eventually, life led him into a path that surprised even him.

4. From Police Academy to Psychology

One of the things I love most about the 20 Year Time Out Podcast is finding out how people’s journeys evolve in ways you could never predict.

Billy went from:

graduating the police academy
working in emergency settings
training people in gyms
discovering an interest in psychology
earning his master’s degree
helping people in recovery and substance use therapy

His path is a conversation about growth.
About changing direction.
About listening to the tug inside you that says you belong somewhere else.

Talking to him, I realized something:
Billy has always been the kind of person who wants to help others.
Even as a kid.

It just took life a few decades to reveal the exact form of that instinct.

5. Martial Arts, Alter Egos, and the Psychology of Fighting

One of my favorite parts of the episode was hearing Billy break down the psychology behind martial arts, performance, fear, and identity.

He talked about:

alter egos fighters create to overcome fear
why some fighters are killers in the gym but freeze under lights
how identity affects confidence
how martial arts becomes “the art of not fighting”
how fear shapes us in ways we do not even notice

It was one of the most fascinating conversations I have had on the podcast.

And it reminded me how much depth people carry beneath the surface.

6. Childhood Memories, Parenting, Movies, Philosophy, and Everything in Between

This episode did what real conversations do.
It drifted.
It expanded.
It got weird in the best way.

We talked about:

raising kids
what they are exposed to today vs what we were exposed to
The Simpsons
AI in storytelling
dream worlds and simulations
near death experiences
religion and spirituality
memory palaces
fears
hopes
growing older
staying curious
and why having hobbies might be the key to staying sane

It was deep.
It was funny.
It was nostalgic.
It was exactly what the 20 Year Time Out Podcast is supposed to feel like.

7. A Friend You Never Really Lose

The heart of this episode is simple.

Billy and I were kids together.
We grew up.
We grew apart.
We lived completely different lives.
And then one day we sat in a basement for over an hour and talked like no time had passed at all.

That is the power of old friendships.
They never really disappear.
They just wait.

Wrapping It Up

Episode 4 of the 20 Year Time Out Podcast might be the most nostalgic one yet. It reminded me why I started this show in the first place: to reconnect, to remember, and to give space to the people who shaped who I am.

If you grew up in the nineties, played Mortal Kombat in a wood paneled basement, prank called strangers, or hung out with neighborhood kids until the streetlights came on, you will feel this episode in your soul.

Watch the full conversation with Billy on YouTube.
Subscribe if you want more real reconnections like this.

I am Rich Marks the Spot.
Thanks for being here.