I thought I lost

(Watch me tell this story here)

It was the last game of my senior year.

We'd just lost. Season over. No playoffs. And I was sitting on a bench in the visiting team's locker room, shoulder pads still on, head in my hands, crying next to guys I'd spent every summer with since sophomore year.

We went 5-4. Didn't even sniff the playoffs. And honestly? It was crushing.

See, I'd spent three years chasing something specific. I wanted to be a football player at my school because football players mattered. Girls wore their jerseys in the hallways. Your name was literally on someone's back. You were known. I wanted that so badly I spent every summer getting stronger, showing up to every practice, doing everything right.

I ended up being a 152-pound left guard who won second team all-league honors.

(I was tiny. Like, comically small for that position. But I was strong.)

I never got to be captain. We never won a championship. And sitting in that locker room, I thought I'd failed.

But something happened in that room that I didn't have words for at 17.

Sitting next to my teammates — guys who'd pushed me, challenged me, who knew exactly what I'd sacrificed — I felt something I'd never felt before. I felt like I belonged. Like I was part of something bigger than me. Coming from a divorced home, wanting so badly to feel connected to something solid, I'd found it. Not in the trophy. Not in the jersey. In the people next to me on that bench.

I didn't know that's what I was looking for. But it was.

I carried that with me for the next twenty-five years. And somehow I still managed to forget it.

Because when I started building a business, I did what a lot of entrepreneurs do — I built alone. On an island. Making every decision by myself, second-guessing constantly, and quietly wondering if what I had to offer actually mattered.

I had this idea for a course. A community. Eventually, a mastermind — for video business owners who were ready to grow. And I kept not launching it. I had a hundred reasons. The timing wasn't right. It wasn't ready. I wasn't ready.

What I didn't realize is that every day I waited, there were people out there who needed exactly what I had — and I was keeping it from them. I was calling it patience. But I think it was just fear. (I'm still not totally sure where the line is between those two, if I'm being honest.)

I didn't figure that out on my own.

I was sitting poolside at a mastermind retreat in Santa Barbara. Round tables, warm afternoon, my wife Andrea was there. And my friend Graham Cochrane — who had been listening to me hedge and delay and explain myself for months — looked at me and said what he always says.

Go ugly early.

Meaning: stop polishing. Stop perfecting. Stop waiting for the moment you feel ready, because that moment isn't coming. Just launch the thing. It's going to be messy and imperfect and that's exactly how it's supposed to start.

I went home and launched the course. Then the community. Then the mastermind.

And it changed the course of my life.

Not because everything magically worked out — honestly, there's still a ton of room to grow. But because I stopped building alone. I found my locker room again — a group of people who push me, challenge me, and remind me what I'm actually capable of. And I get to be that for other people now too.

I keep coming back to this: the thing I thought I was chasing is almost never the real thing.

At 16, I thought I wanted a championship. I needed belonging. At 40, I thought I wanted to launch a perfect product. I needed people around me willing to say go ugly early when I was stalling.

If you're building alone right now, I'm not going to tell you it's wrong. But I will tell you it's how I spent years moving slower than I needed to. And the thing that changed wasn't a strategy or a system — it was finding people who got it.

I'm putting together a small group — twelve business owners max — who are done building on islands. We meet, we challenge each other, we go on retreat together. It's the thing I wish I'd had a decade ago.

If that's resonating, I'd love to talk. Just reply to this email or grab a spot at the link below.

And if you're not ready yet — that's okay. Just start noticing who's in your locker room. Who's on your bench. That might be the win you didn't know you were playing for.

To belonging,

Ryan

P.S. I've been reading Storyworthy by Matthew Dicks and it's messing with how I think about every story I tell. If you want to get better at telling yours, it's worth picking up.

P.P.S. If you don't just want to tell a better story but want to build one — with a small group of entrepreneurs who actually push each other — that's what the mastermind is for.