My dad went to prison.

It’s true: my dad was in the Navy, got out, spent the rest of his career as a corrections officer for 25 years. My stepmom worked at a facility for sex offenders next door.

Both of them went to prison every single day.

And I didn't realize how much an influence that was on me until a few years ago when a guy I worked with asked me what my dad did for a living-- I told him and he nodded and said, "That explains a lot."

Before I go on:

1. Don't worry, my dad is still alive and well. This isn't a memorial post!

2. I know the other side of prison pretty well too: my dad’s twin brother, my stepdad, 2 of his brothers, my aunt, a girl I dated for a while, and one of my close friends all did time.

I didn’t think anything of it as a kid— I thought it was just normal to have prison be such a big part of your life.

As I got older I realized that it definitely was NOT normal, but it did teach me a lot.

First of all, to be on top of your shit 24/7, with no exceptions or excuses.

Prison is a nasty place, and if you get caught slipping (as an inmate or a CO), it could be a very bad time for you. You don’t always get a second chance.

But beyond that, the biggest thing might not be what you’d expect from a CO: it was the concept of leading with influence rather than authority.

It might be counterintuitive, but think about it: This was a Level 4 facility (maximum security), so these guys were doing serious time and he might have to spend years with them. And there were hundreds of inmates vs a couple dozen COs.

So going in there thinking you’re a badass who’s gonna kick ass and take names is not the move (ask anyone who’s tried).

But as a kid, that didn’t make sense to me at first— why didn’t they just use their power as COs to make everyone follow the rules? Why not just drop the hammer?

But over the years, it started to make sense: he told me that he always treated the inmates with respect and built relationships rather than trying to control or intimidate them. Because why make an enemy out of them if you don't have to? Why take the risk of shaking down a cell block to find a weapon if you could just have an informant tell you where it is?

To be clear, he’s not a soft guy at all. He sets very clear boundaries and expectations— you always know exactly where the line is, and what will happen if you cross it. Call it “tough but fair.”

Above all else, you know you can trust him.

So when he did investigations after an incident, he always followed the facts even if it meant finding that a CO was in the wrong. That’s not popular with the other COs, but it’s the right call in the long run because it showed that he has integrity. After all, how could the inmates trust him if they felt like he'd always find them at fault?

He was also trained as a hostage negotiator, and YES he 100% used that sht on me 😅 He always let me make choices on my own, but he led me to the right choice by laying out the options for me. "Sure, you can do that if you want... but here's what will probably happen if you do."

Years later, I came back to those stories he told me when I was a kid.

I was maybe 25ish and clashing hard with some people at work. I thought about my dad, and I realized where I was fking up: I would just try to hammer people with facts, thinking they’d eventually realize I was right (or maybe just give up from the pressure) and they’d go along with my idea.

If you’re cringing right now, I don’t blame you 🫢 I came off like a pushy, arrogant a-hole.

And that’s when I realized why my dad did things the way he did. And as soon as I switched gears and focused on building relationships and earning trust, life got a lot easier for me.

“Cool story Finn, why are you telling me this?”

As an entrepreneur, you are a leader whether you realize it or not: leading your team, and leading your clients/customers/users where they need to go. And leadership isn’t pounding the table and telling people what to do. It’s building trust, relationships and helping people.

So when in doubt, ask yourself “is this what a leader would do?”

Make sure the answer to that question is a firm yes 💪

PS - If you like my emails, reply to this and say hi! I don’t have any room for new clients right now so I have nothing to sell you, but I always like talking with people.