Pickups and Drop Offs to and from Prison

Over my time driving Uber, I've had all kinds of passengers. Some were hedge fund managers going to LaGuardia. Some were college kids going to bars. And some were people going to or coming from prison.

I've dropped off prison guards. I've picked up people who just got released. Each ride taught me something about humanity, judgment, and staying calm under pressure.

The Pickup at the Wawa

It was a chilly Friday night near Secaucus. I got a ping from a Wawa right next to a prison facility in Northern New Jersey. Two guys got in—one of them had clearly just been released.

The smell hit me immediately. It wasn't subtle. This guy hadn't showered in three days. My car, which I kept meticulously clean, suddenly felt like a completely different space.

In that moment, I had a choice: react with disgust, or be professional.

I chose professional.

The Reality Check

As we started driving, one of them started Face-Timing a family member on speakerphone. Loud. Over the next 30 minutes, I got the play-by-play of their story.

They'd been arrested on the GW Bridge. Expired registration. Back child support. Allegedly a domestic dispute that wasn't true, according to them. They spent days in holding before getting released.

I had my headphones on, my music playing. I minded my own business. But I was listening. And I was nervous.

I hadn't ever been this close to someone who'd just been in jail—except in movies. And in movies, these situations don't usually end well.

The Fear Response

My heart was racing. My mind was going through scenarios. What if this goes wrong? What if he gets aggressive? What if—

Then I remembered my Cognitive Behavioral Therapy training. I grounded myself. Took a breath. Asked myself the critical question:

"Am I in immediate danger right now?"

I looked at the situation objectively:

Had this guy threatened me? No.
Had he harassed me? No.
Was he being violent? No.
He was just talking loudly on the phone, dealing with the aftermath of a terrible few days.

My gut told me I was safe.

People Make Mistakes. They're Human.

Here's what that ride taught me: People make mistakes. They're human.

I don't know the full story of what happened on that bridge. I don't know if the charges were fair or if the system worked properly. What I do know is that I was sitting in a car with someone who'd just had one of the worst experiences of their life.

And instead of treating him like a criminal, I treated him like a customer. Point A to Point B. Professional. Respectful.

He didn't ask for judgment from me. He asked for a ride.

The Lesson for Founders: De-escalation

Most people would have been terrified in that car. I was too—at first. But here's the thing: fear is a signal, not a directive.

As a founder, you're going to face situations that trigger your fear response:

Investors who are skeptical or aggressive
Customers who are angry about bugs
Co-founders who disagree on direction
Competitors who seem threatening
Market conditions that feel unstable

In those moments, you have a choice: escalate or de-escalate.

De-escalation is a superpower.

How I De-escalated

Grounded myself - Took a breath, assessed the actual threat level
Stayed professional - Didn't let my discomfort show
Minded my own business - Put on headphones, gave them space
Completed my goal - Point A to Point B, safely
Didn't judge - Treated them with the same respect as any other passenger

That approach works in business too.

When a customer is angry, ground yourself. When an investor is aggressive, stay professional. When things feel chaotic, focus on the goal. When someone makes a mistake, remember they're human.

The Bigger Picture

I've dropped off prison guards going to work. I've picked up people leaving after serving time. I've seen both sides of those walls.

What I've learned is that most situations aren't as dangerous as they feel. Most people aren't as threatening as your brain tells you they are. And most conflicts can be de-escalated if you stay calm and professional.

The guy who smelled terrible? He was just trying to get home after three days in a cell. The loud conversation on speakerphone? He was just relieved to finally talk to his family.

I successfully dropped off both passengers and was on my way. No incident. No drama. Just another ride.

Your Turn

As a founder, you'll face uncomfortable situations. Stressful conversations. People who trigger your fear response.

Remember: Did they threaten you? Did they harass you? Or are they just human, in a difficult situation, doing the best they can?

Stay calm. Stay professional. De-escalate. Complete your goal.

That's the lesson from the prison rides: not every scary situation is actually dangerous. And the ones that aren't? Those are opportunities to practice staying calm under pressure.

Because if you can handle picking someone up from prison at midnight without letting fear control you, you can handle a tough board meeting, a difficult customer, or a stressful pivot.

Fear is information. What you do with it is what matters.

Being a founder requires handling situations most people would avoid. But avoidance isn't an option when you're building something. Learn to de-escalate, stay professional, and trust your gut.