POV: Founding a fashion brand that sold for 9-figures!

Chubbies was founded in, October 2011 by Preston Rutherford and three of his closest friends. The company has since been acquired for 9-figures and went through a 10-figure IPO - your classic overnight success that took a decade.

Hamish: Take me back to before you started Chubbies.

Preston: You know when you have a group of people where you talk about this kind of stuff?

That was me and my Co-founders - Kyle, Tom, and Rainer.

We all respected each other and thought we would like to work together someday, so when we reached this point in our lives of not enjoying working for other people and feeling ready to start something, we thought it would be cool to create something together.

Hamish: Did you know what it was that you wanted to achieve?

Preston: We all wanted to start something and be entirely responsible. Where everything was up to us, and no one could stop us - where there was no ceiling.

There's no universe where we could have imagined the scale at which Chubbies is today, but that isn't necessarily what I mean by no ceilings.

"At the time, I was just excited about the opportunity to work with my closest friends and create something that people would love."

But no, I never could have dreamed of where it's gotten today and where it will hopefully go.

Hamish: Was it hard Co-founding with your closest friends?

Preston: They are the best operators I have ever come across. Supremely capable, confident, brilliant, thoughtful, and driven.

And I know I need Co-founders.

I have so much respect for those who do it themselves - It's just so lonely and hard.

I also know that we got so much value from our different perspectives, you know? We would argue and work through things a lot, but we always ended up in a better place than we would have if we had just gone with our initial view.

"I think we made better decisions for our customers and created better products because there was a table full of different perspectives."

Hamish: What did you feel like everyone brought to the table?

Preston: Rainer brought immense product sense and a strong opinion on manifesting the vibe or brand we were striving for into a physical product. He had this intense creativity but also a distinct quantitative ability.

"That's one of the things that made our founding team extremely potent. A strong quantitative background and ability to back up creativity with numbers."

Kyle was an operational and strategic leader for us, but also the person on the team who always understood how everyone in the room was feeling and their perspective.

We joked that he was the father of the team.

Tom was just brilliant. The most brilliant writer, content creator, and student of human and consumer psychology. And again, a quantitative mastermind in a world where we would live in spreadsheets.

And me? I was a bit of a unifying force across all these strong personalities. I'm a little more go-with-the-flow, synthesize, and I think that brought us together and helped us find a way forward many times.

That's how I would think about it for the four of us.

Hamish: When did you first think "OK, this is working"?

Preston: At the beginning, we all stayed at our full-time jobs for quite some time. Quitting our jobs would have been that moment for us.

I think we got to a multi-million-dollar annual run rate before we started to go full-time. But even before that, other markers gave us a lot of confidence.

I remember being out in the real world and seeing people responding to our brand. We had people who loved our brand, but also people who hated it. People did not feel apathetic about it, we had created something noticeable enough to draw out a response.

"The 'holy s*** - this is crazy.' moment was when people we had never met started posting on social media and tagging Chubbies or doing #chubbies."

Hamish: What did transitioning to full-time feel like?

Preston: It was amazing. It's the best feeling. There was such a strong feeling of organic momentum, and we were excited about having even more time to work our faces off for our customers.

"You feel like - not the world is your oyster - but let's devote our lives to this. Let's capture whatever this is and give our all for our customers."

It's hard to describe, but it was way better than we were doing before working for other people.?

And then we started making our first hires and starting our first interns, and it was like holy s*** people want to join us and devote their lives to this too.?

That team kept growing and took our dream and vision to a place that we never could have imagined.

Hamish: Can I ask for one piece of advice as a founder 12 months into their journey?

Preston: View your customers as your friends.?

At Chubbies, we thought of the people who were buying our products not as a faceless source of money, but instead as a friend. And with friends, you invest before you extract. Treat people in a way that builds long-term relationships.

We were never perfect at Chubbies, but we tried immensely hard at it, and our customers saw it and respected it.