Preston Rutherford, Co-Founder of Chubbies, on How to Build a Resilient, Human-First Business

Amanda Kahn
Amanda Kahn
Dec 19, 2023

Remember when shorts only came in black and khaki? Before Chubbies hit the market, shorts options were a little lackluster. In Episode 108 of Earned, Conor sits down with Preston Rutherford, co-founder of the California-founded shorts company, Chubbies.


To start, we dive into the unique story behind the founding of Chubbies, and learn about what sets Chubbies apart from the competition. Next, Preston shares what went into a couple of Chubbies’ creative marketing programs, such as its tailgate tour and “koozie palooza.” With the goal of maintaining “human to human friendship” versus becoming a corporate company selling to faceless customers, we unpack how Chubbies utilizes short- and long-term strategies to build resilience for its business. Preston emphasizes the role of institutional inertia, as well as the importance of remaining patient while deploying longer-term strategies. Additionally, we explore how Chubbies evolved based around the notion that the best creative constraint is a limited budget, which allows for the highest quality in idea selection. Preston reveals how Chubbies uses its metrics, and explains why he finds surveys to be the best indicator of customer temperature. To close the show, Preston encourages us to put on a show, have a little bit of fun, and most of all, be memorable. 

We’ve included a couple of highlights from the episode below, but be sure to check out the full video above, or tune into the podcast on Spotify, Apple Podcasts, and Google Podcasts!

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The following interview has been lightly edited for concision. 

“You have to look a certain way. You have to be a certain way. Our idea was to forget that. You be whoever you are”: How Chubbies Positioned Itself Through Intentional Advertising  

Conor Begley: You guys employed a few fairly non-traditional marketing tactics early on, like the bus that you took across the country. Tell me about some of the non-traditional things you guys did early on that you think really stood out.

Preston Rutherford: Just to touch on your first point, which was how content that seems like it was created by your friends or by yourself seems to resonate and get greater distribution—I think that was less obvious and less proven. Imagine a Ralph Lauren photoshoot or an Abercrombie photoshoot. Men's brands of that kind had a strong association with being highly produced, spending hundreds of thousands of dollars to get these beautiful people, this setting, these poses, right? That was the expectation because that was the norm. So then when you have an unretouched iPhone photo, these were not visually stunning images, and they clearly did not come across as being professionally done. It was just the opposite. It was one of those fundamental tensions where it's so bad, it's interesting. So that was our thinking: let's just try to be the opposite of everything else that exists where it's this very stuffy, very serious, very exclusionary, “you can't hang with us” sort of thing. You have to look a certain way. You have to be a certain way. Our idea was to forget that. You be whoever you are. Have a great time. We're not trying to be anything. We're just like you. We're all on this journey together. Those were some of the foundational things that guided how we operated.

“It's the best possible creative constraint when you don't have the money, because there's so much you could do, but there’s limited funds”: Chubbies’ Preston Rutherford on How To Make The Best Decisions

Conor Begley: You were doing these nontraditional marketing tactics, these community-building efforts, but then from a digital marketing perspective, you got in at the early stages. You started with, ‘what's the ROAS (return on ad spend) on these kinds of things,’ but then pivoted and realized that actually, I don't think this is the right approach for us. Take me through that journey, and what you learned there.

Preston Rutherford: To the beginning component, when you're a company and you've got no money, you've just got to do the free things, right? You've got to be as creative as possible. It's the best possible creative constraint when you don't have the money because there's so much you could do but there’s limited funds. I felt like it was where some of the purest, most creative stuff was happening. Then you either raise a little bit of money or you start selling some product and you have a little bit of cash. I wouldn't necessarily say that we got lazy, but we started doing the digital paid social direct response. It takes you down a path where you start to get this feedback loop. You start to generate some sales, you start to be able to grow. And for a while, I think that worked. That worked for a lot of brands, ourselves included. The economics were such that I think they're quite different than they are today.
You start looking at your business and you're like, “Oh, I'm growing the top line pretty nicely, but as I have to grow off of a larger base, it just gets harder from a percentage basis to keep growing as quickly.” Are we going to be able to raise more venture, or how are we going to fund this thing? How are we going to fund the future growth?

Keep up with new episodes of Earned by following the podcast on Spotify, Apple Podcasts, and Google Podcasts, or subscribing to our YouTube channel. To catch up on our previous episodes, featuring leaders from brands like Revolve, K18, Instagram, and Roblox, visit our Earned Podcast page.