This is a story about a clown, a t-shirt, a band, and a livestream.

I'm not writing it for a lot of people. I'm writing it for one, whoever that turns out to be. Maybe it's you.

Here's the whole idea, as plainly as I can say it: don't try to make something for a lot of people. Make it for one person first. And take it one step further than that. The thing you make isn't finished when you finish making it. It's finished when it reaches that one person it was for.

I learned that before I understood a word of it.

The Clown

It starts with the photo above.

My dad was eleven in it. He'd painted a portrait of Emmett Kelley, the clown famous for playing a sad, broke hobo. It could have just sat around his house, the way most things a kid makes eventually do. Instead, he found a way to hand it to Kelley himself, in person, at the New York World's Fair, in 1965.

Basically slid into his DMs. Sixty years early.

He'd made something specific, for one person, and he wasn't going to let it just sit around until it reached him. I don't know if he saw it that clearly at eleven. He probably just wanted to meet the guy. But looking at it now, that's exactly what he was doing. Maybe I'm reading too much into a kid's afternoon at the World's Fair. But that's how I see it.

I didn't grow up hearing that story like some kind of lesson. I just grew up watching my dad paint. He's still doing it, actually, now that he's retired from a career in financial services and back at it full time.

The T-Shirt

I was 13 the first time I noticed the same instinct in myself.

I could already draw. Then I took a Photoshop class, and I started going to local punk shows in Freehold, New Jersey, standing around the merch tables. I noticed the bands with the better graphic tees always seemed to have something going for them, and I remember thinking, "I could design those."

There was a band called Postmark September. I found the lead singer's screen name on AOL Instant Messenger and messaged him directly. Told him I could design a shirt for the band.

That was the whole pitch. And it worked.

A few weeks later I needed someone to actually print what I'd made. There was a guy across the street named Gary. Retired UPS driver. Printed shirts in his garage for local businesses and schools. Never once wore a t-shirt himself, despite printing thousands a week. I called him "Shirtless Gary."

I knocked on his door and told him I lived across the street, heard he printed shirts, and had some local bands who could use some. He told me to meet him around at the garage.

I can still remember the garage door going up. The smell of Black & Milds and plastisol ink billowing out. His dog Bailey, waiting behind an old hollow-core door, the kind you'd find inside a house, off a bathroom or a closet, laid flat across the entrance so Bailey could hang around without running into the street, still able to hop up and greet you as you climbed over it.

A shared family computer, a bootleg copy of Photoshop CS4, a design I made for a local band, and a neighbor with the right equipment. That's how I got started. I became a designer.

The Band

A year later I started a t-shirt line called Kill the Pilot, built around a phrase I couldn't fully explain yet but believed anyway:

Fly your own plane. Kill the pilot.

Six years after that, the phrase became the ethos of a band I started, The Pilot Kids.

That part of the story I've actually told before, the short version is we signed with a Grammy-winning producer, met Skrillex in an airport, and got noticed by exactly the one person who'd understand what we were doing, not by trying to reach everyone. If you're interested, you can read more on how I almost became a rockstar here →

The Livestream

After the band, I spent the next decade in rooms full of other people's brands. But the moment that actually taught me something was a conversation with Pastor David at kings' Church in New York City.

It started as a livestream problem. The quality was suffering, and this was during COVID, so for a lot of people the stream wasn't a nice-to-have. It was the only church they had. Pastor David wasn't really asking me to fix a video feed. He was telling me who he felt responsible for, the people in the room, and the people who'd only ever be a screen away. I built everything after that, the app, the training, the systems behind a fifteen-person team, around reaching those exact people he'd described.

Same move, again. Not making something for everyone. Making something specific enough to one person's purpose that when they saw it, they recognized themselves in it.

The Takeaway

Somewhere along the way I stopped thinking of it as branding and started thinking of it as a portrait. There's a verse, Proverbs 20:5, that says the purpose in a man's heart is like deep water, but a man of understanding will draw it out. That's the whole job, as far as I can tell. Someone has something true and deep already in them. Someone else helps draw it out and hands it back to them in a form other people can finally see.

That's what my dad did in 1965. He looked closely enough at one man to paint him, then made sure that man got to see himself in it.

That's still the whole job.
Look closely enough at someone. Make something that reflects them back. Then put it in their hands.