The Cowboys Who Raised Me
A story from The Cowboy In You
They say, "Show me who you spend time with, and I'll show you who you become."
Well, I was lucky. God placed Cowboys in my path from the beginning.
I didn't call them that at the time. Back then, I didn't have this framework, this idea, "the Cowboy in you."
But they were Cowboys all the same. Each one different. Each one vital. Each one left a mark.
And thank God for that.
When I was growing up, most Americans still leaned Cowboy. This was the 60s, 70s, 80s. Men were hard because life was hard.
My family were Irish immigrants. Most of the cousins stayed in the city, but my father, he chose something else.
He moved us out to a small town with land. He loved the country. Maybe needed it.
He was hard. Probably too hard. But it was all he knew.
One night, much later in life, I had dinner with my Uncle, my dad's best friend since they were kids.
He looked at me, a quiet moment, and said:
"Your father had a very hard upbringing."
He didn't explain. Didn't need to. It just hung there.
That was enough.
My dad never had a bed growing up. Slept on the floor of a small NYC apartment.
We're Irish, we don't talk about our problems. We just suck it up. No therapist, no soul-searching. That's what Guinness is for.
But pain still finds its way in. It leaves a trail. Sometimes in silence. Sometimes in steel.
Thankfully, my mentors didn't stop at my father.
There was Uncle John: Navy SEAL, combat vet.
I'll never forget when he went missing after being shot in the jungle. For months, we had no idea if he was alive.
My mother was frantic. I can still see the stress in her eyes.
Then one day, a photo arrived. Uncle John, alive, wounded, in a hospital bed, smiling.
An American Cowboy.
Then there was Uncle Tom. The most charismatic guy in the room. He lit it up... energy, ideas, hope, vision.
One of the youngest executives on Wall Street. Started his own firm. Made it big.
Then hit rough times. The bottle got the better of him.
But he was a Cowboy to the end.
Flawed, but unforgettable.
These men weren't perfect, but every one of them carried at least one Cowboy trait. Often more.
And not just mine.
Our fathers grew up in the shadow of the Greatest Generation, men who survived the Depression and fought in WWII. They didn't explain grit. They embodied it.
They built the country we take for granted today.
As I got older, God kept putting Cowboys in my path.
When I joined the CIA, one of the first was Mike.
Marine. Vietnam veteran. Hard as nails. Inspiring.
He wasn't the kind of leader who kept you on the sidelines. He threw you into the fire, not recklessly, but with belief.
He trusted young guys. Gave us responsibility early.
That kind of leadership is rare.
After training, he called me.
"El Salvador," he said.
He was heading there as Deputy Chief of Station.
Was I in?
Hell yes, I was.
Steve, the Chief of Station, was a legend, a Vietnam vet who'd commanded Montagnard tribes in the jungle, training them to fight the Viet Cong.
Another Cowboy. Through and through.
I learned that fast.
Early on, there was an incident. A rescue that went sideways. I couldn't save my buddy. It tore me up. Still does, if I'm honest.
I went to Steve, rattled. He looked at me and said:
"Don't think one more minute about that. If you did, you'd be dead."
He'd been there before. He knew. That was Cowboy mentorship: no coddling, just truth.
Another time, I nearly got myself fired.
I worked a cover job at the embassy. My boss there was a Bureaucrat, classic. We clashed constantly.
One day she was riding me hard. I'd had enough.
I told her to fuck off.
Big stink. Huge. I figured I was done.
Got called into Steve's office. Walked in expecting a dressing down.
He looked at me. Paused.
"Did you really tell her to fuck off?"
I said, "Yup."
He just laughed. Hard. I can still see his face... tears in his eyes, shaking his head.
"Get out of here," he said.
That was Steve.
Now, in retrospect, I shouldn't have said it. I was wrong. That boss and I actually became friends later. But she was a Bureaucrat, and I was a Cowboy. Oil and water. Classic Cowboy crap. And Steve knew it.
Reagan had drawn the line: we would not let communism take El Salvador.
No massive troop deployment. Just special forces. CIA. Advisors. People who got things done.
Everyone there had Vietnam experience, except me.
I was the kid. But I soaked up everything.
It was hard. Real. Dangerous. And it was glorious.
I got to stand shoulder to shoulder with real American Cowboys.
And it changed my life.
Mike eventually retired and did what Cowboys do: built a new life. Started a company. A vineyard. Lived full, lived free.
He died skiing out West. Fast. Sudden.
A legend no one will ever hear about.
But I knew. I remember. And I honor him now.
When I left government, I stayed in Latin America.
Was supposed to go to Mexico next, drug war was heating up. Could've gone. Might've ended up dead.
But life took a turn.
I launched a business. And again, another Cowboy showed up. Tom Pownall. CEO of Martin Marietta. Naval Academy grad. Fortune 500 heavyweight.
He knew my past. Saw potential.
I had no money. Just vision.
He backed me anyway.
Most Americans wouldn't set foot in El Salvador after the war. He flew down with me. Met the locals. Shook hands. Built trust. Took risks.
We started a company together.
He co-signed my first mortgage. Attended my wedding.
We got married on an island called Teopan, owned by my father-in-law. Still one of my favorite places on earth.
The business worked, but it wouldn't scale.
Tom lost money. I hated that.
But he never complained. Never asked for anything.
When I pivoted to tech, he was the first to cheer me on.
He was a mentor. A friend. A Cowboy.
God rest his soul.
There have been others.
But the last one I'll tell you about, he may have been the most important.
The one I call the Quiet Cowboy.
Most of my mentors were hard-charging, visible, classic Cowboys. But the Quiet Cowboy lived in the rarest zone. The sweet spot. Not loud. Not showy.
He shaped my soul more than any man I ever met.
You'll meet him later. And when you do, you'll understand.
I didn't always live up to what they gave me. But I never forgot it.