Alex DiMattio

It starts with a question.

Not a branding exercise. Not a pitch deck fantasy. Just a simple, disarming ask from a sponsor at an AA meeting.

If you could do anything in the world, what would you want to do?

For Alex DiMattio, the answer came fast.

Clothing and motorcycles.

So he did it.

We meet Alex inside his world. Not a showroom version of it. The real one. Tools out. Materials everywhere. Ideas half built and constantly evolving. He owns Jane Motorcycles, but ownership here feels less like a title and more like responsibility. To himself. To the people around him. To the culture that raised him.

“I got out of prison,” he says plainly. No drama. No polish. Just fact. And from there, the story doesn’t arc upward neatly. It moves sideways. Forward. Back again. Like real life does.

Jane isn’t built as a seasonal brand. There are no drops planned by committee. Everything starts in Alex’s closet.

“Everything we make is just an extension of my closet,” he says. “We don’t do things as a line. We do things as individual products.”

Each piece is personal. A jacket made for the days he wants it lighter. Shorts with pockets that fit baby bottles. A bag that has taken three or four years to get right because it has to work for him first.

Perfection is not the goal.

“There is no perfection,” he says. “Perfection is boring.”

That line hangs in the air for a second. Because it explains everything.

Alex makes things in Brooklyn. Not because it’s efficient. Not because it’s cheap. Because it’s home.

“I didn’t base this company around just making money,” he says. “It’s more about the people I interact with and where it’s made.”

You can feel that lineage in the room. Skateboarding. Nightclubs. Old New York energy. Urban culture before it was commodified. Jane doesn’t chase trends because it doesn’t need to. It exists inside a lived-in ecosystem.

The motorcycles aren’t just machines. They’re meeting points.

The clothing isn’t just apparel. It’s utility shaped by experience.

And the brand itself feels less like a business and more like a stance.

After thirteen years, Alex is still in it. Still battling. Still rebuilding.

“A lot of times in business, you’re going to have to go back to the beginning again,” he says. “You’ve got to do everything.”

That moment where things get uncomfortable. Where ego wants to step aside. Where the work asks you to start over.

“It’s scary for a minute,” he admits. “But it’s actually fun.”

Fun because it’s real. Because it’s his.

“When you put finances before it,” he says, “it’s not cool anymore. It has to be your thing.”

And maybe that’s the quiet thesis of this whole day. That the thing you build should still feel like it belongs to you. Even when it’s hard. Especially when it’s hard.

“I wanted to make a clothing brand,” Alex says with a shrug. “I made a clothing brand. I don’t really give a f***. It is what it is.”

No overthinking. No permission seeking.

Just one foot in front of the other.

Every single day.

And then he looks up, half smiling.

“You guys ready to go make a f***ing clothing company?”

The room laughs. The engine hums somewhere in the background.

And the movement keeps going.