It started out in 2011 as a side hustle for four friends from Stanford University who rebelled against “shirtless men with rippling ab muscles, some standing outside of storefronts coating you with cologne.”
They were also frustrated that shorts — their go-to piece of apparel — were getting longer and more complicated.
So these friends — Kyle Hency, Rainer Castillo, Preston Rutherford and Tom Montgomery — set out to create their own version of retro-inspired shorts in bold colors and bright patterns. They called their company Chubbies.
Fast-forward 13 years and Chubbies has created a $100 million-plus business that has moved beyond just shorts to include swimwear, polos, T-shirts, hoodies, loungewear, pants and other basic menswear pieces for regular guys who appreciate its irreverent attitude and everyday man assortment.
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Its motto: “Friday at 5:00.”
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In 2021, the brand was purchased by Solo Stove for $129.5 million in cash and stock and months later, Chubbies became an anchor company for the newly named and newly public Solo Brands. Sales last year reached $101.6 million, up from $89.3 million in 2022 with $9.1 million in net income, reversing a minor loss the prior year.
Only Castillo remains at the business under its new ownership as the other three founders have moved on. “They are entrepreneurs at heart and in pursuit of their own sort of technology start-ups at this point,” said Castillo, who serves as president. “For me, my heart’s still here. I want to make sure that if I leave this business, I’ve set it up for long-term success.”
He said since the acquisition, he’s worked to formulate a strategy to ensure that success. “What does the brand look like in the future?” he asked. “What is our focus? How do we make sure we’re building something that allows this company to continue to grow?”
Castillo said in its infancy, Chubbies created product for him and his friends. But now, that lens has been expanded to include a wide range of customers. “The mentality of the past is: hey, we’re really building product and gear for us, and now we’re really focused on this customer that we’ve fortunately nurtured over the course of the past decade, and have the ability to introduce new things to.”
Castillo said Chubbies benefited from the fact that it launched at a time when social media was just gaining traction. By embracing this new — and free — technology, the brand was able to build a “massive community” of like-minded men.
And the fact that it was a direct-to-consumer brand when the online businesses were booming also helped Chubbies quickly build a legitimate company.
“We were an e-commerce-era darling and things went really fast,” he recalled. “We went from $2 million to $20 million in the first few years. We launched our website in 2011 and didn’t have our first physical point-of-sale until 2017.
“Our very first pop-up was this empty space next to our favorite bar in San Francisco,” he said. “We would all go there after work, and one day, we asked them: ‘Why is this empty? Would you give us a deal to put a pop-up in here over the holidays?’ They did, and we realized we could create an energy and enthusiasm for the brand that was a completely different experience than purely engaging with us online.”
From there, the founders spent a number of years opening pop-ups in various places around the country learning about their customer and how to be retailers.
“We went into COVID[-19] with seven or nine stores, but we had five that were really profitable, so we narrowed it down to five markets where our customer existed.” The founders built the stores themselves and they were like “clubhouses, built by hand,” he described. “There was no hiring of outside resources to help us design these spaces or build them. They were like hangouts for our friends and for our customers in these markets.”
Last year, the company did a major renovation of its store on King Street in Charleston, S.C., and “immediately, we saw performance accelerate,” he said. “It was the same exact space, the same exact team, but just the setting and shoppability of the store allowed us to move faster. We’ve been rolling that out to a lot of our stores over the course of this year and opening a number of new stores that are reflective of that mentality.”
By the end of this year, Chubbies will have 12 stores, 10 full-price and two outlets. The stores are located in markets where customers already exist — Crabtree Valley Mall in Raleigh, N.C., and the Mall of America in Minneapolis, for instance, not Abbot Kinney in Los Angeles or SoHo in New York.
“We’re really data-driven so we’re looking for the best options for us,” Castillo said.
Chubbies’ core customer is a young Millennial man who grew up with the brand. “We’ve been a piece of his wardrobe probably since his first days in college. But he’s evolved now — he’s a dad or he’s married and has other interests in life. And we’ve been fortunate enough to have his trust for this sort of life cycle of growth. I call him The Weekender. He’s my bull’s-eye for the brand: 25 to 40 years old.”
But the company has managed to gain a foothold with younger men as well. Chubbies now offers boyswear because its customers started having children and would buy pieces for their sons in bright colors in the smallest sizes possible. “So we said, maybe there’s an opportunity here,” Castillo said.
And it’s worked. “We’ve seen really good traction with that,” he said. “And we’re similarly invigorating a generation of high schoolers and younger right now that will hopefully be with the brand into the future.”
Its bestselling items today are its swim trunks and its performance polos, Castillo said. “Our original mission for the brand was to create the most radical shorts on the planet, and that was very focused and very tight,” he said. “And for us, that meant loud and short and comfortable with an elastic waistband. As a result, when you think of Chubbies, you think of shorts. We’ve fortunately cornered a piece of that market.”
But swimwear has passed shorts as the top seller. “There’s no one short that is as big as our swim trunk,” he said.
Looking into the future, Castillo sees many opportunities for growth. But he stresses that any decisions will be based on solid research and data. Chubbies has a strong grasp of who its customers are, where they live and what they like to buy. However, the numbers also tell the company that the online shopper will generally keep buying the same product but the customer who shops in a store will be more likely to purchase other products.
“The ability to touch and feel and understand the brand is different than with somebody who’s not had that experience. The data is telling me that, so I have the ability to sell him more, introduce more categories to him, and that’s really freeing for me as a brand.”
While retail will continue to be a key growth strategy for Chubbies in the future, there are no immediate plans to add units. “We opened a lot of stores this year, almost doubling what we had, so my focus is to be really good in this world of physical retail. From there, we’ll start to explore what our best options are and how we continue to grow the brand.”
The company has also built a strong wholesale business at retailers such as Dick’s Sporting Goods, Academy Sports, REI and other sports- or outdoors-centric retailers.
Although Castillo wouldn’t say what percentage of the business is wholesale, he did say it was growing. “In terms of performance, 2023 was an historic year for us.”
That was also the year that Chubbies formalized its relationship with San Francisco 49ers’ tight end George Kittle. Castillo said the association was organic since the athlete, who is known for his fun and charismatic personality, had worn Chubbies in college. The company reached out and the door opened.
That led to last year’s creation of a George Kittle by Chubbies Collection of shorts, graphic T-shirts, polos, swim trunks and other products in colorful prints and functional fabrics.
And in September, the company signed a licensing deal with the NFL and named Kittle creative director of football.
“Over the past two years, we embedded ourselves with George, his wife, his family,” Castillo said. “So when we signed our license with the NFL, it was natural for us to go to the person we know, who’s closest to the NFL. One plus one equals three here.”
The company will focus on fan gear such as polos and swim trunks emblazoned with team logos. Castillo said Chubbies has no intention of going up against the Nikes and Under Armours of the world. But using Kittle as its “muse,” it now offers the Ultimate Training Short that was created in partnership with the athlete.
“In my mind, it’s the best performance short in the market,” he said. “It’s an amazing opportunity for us to have his feedback. But when it comes to these spaces, you have to earn the right by being consistent and dominant in a category. And for us, that’s swim.”