Twitter Facebook Instagram Google+ Tumblr YouTube E-Mail WhatsApp Sign In Check Close snapchat
Search
Exit Clear

How 4 College Buddies Built A Million-Dollar Empire Selling Short Shorts To Bros

How 4 College Buddies Built A Million-Dollar Empire Selling Short Shorts To Bros: Courtesy of Chubbies

Courtesy of Chubbies

Silicon Valley entrepreneurs love to “disrupt” things. Everything from the way we communicate to the way we move around to the way we eat and dress, so the thinking goes, is primed for dramatic change as technology evolves and makes our lives more efficient.

So when you hear about four former Stanford classmates launching a new startup, it’s easy for the initial reaction to be, “There goes another one.” But instead of focusing on creating the latest “Uber for disenfranchised Uber drivers” or something like that, the four guys behind Chubbies decided to make shorts. Short shorts. And loud ones at that.

Tom Montgomery, Preston Rutherford, Rainer Castillo, and Kyle Hency started Chubbies because they wanted to create a brand that gave you that same feeling you have on Friday at 5 p.m. They wanted to own the weekend and, to them, shorts symbolized that.

The thinking behind shorts that showed a helluva lot of thigh came from the founders looking up to their dads and the steez that they possessed. Chubbies isn’t for rail thin male models who are so pale that they border on translucent. It’s for guys who can appreciate how big of a stud Magnum, P.I. is.

After having a few samples made up and seeing them sell out almost instantly during a Fourth of July weekend in Lake Tahoe a few years back, the founders realized that they were onto something and dove full on into Chubbies. (That sounds kinda gross, I know, but the founders claim that the name is a nod to the shorts’ elastic waistband, which expands if you get a little fat, not an erection nom de guerre. We’ll leave it up to you to determine just how serious they are about that.)

What they found was that people instantly formed strong opinions about the shorts. They either loved or hated them; no one was indifferent. It was more of the former though, and the brand’s first run of shorts on its website sold out within days. Keeping up with demand has only continued since then and Chubbies is now a multi-million dollar company with backing from some of the same investors that are behind Thrillist and Bonobos and has expanded its product offerings into swim trunks and shirts.

We caught up with one of the founders, Tom Montgomery, while he was in New York to to find out more about the short shorts, creating a beer brand that sells clothes, and what happens to Chubbies in the winter.


How did Chubbies start?
Tom Montgomery: We were four guys out of Stanford and had all been working for a few years and had been looking for something to do. As odd as it sounds it was the most natural thing we could’ve done to start a men’s short shorts company. The product was something that we wore every weekend if it was nice out. It was the hallmark of all of our best weekends. They had a good retro feel. We really look up to our dads as the men, as these that dudes had it right when they were young.

Chubbies founder Tom Montgomery (Courtesy of Chubbies)

Chubbies founder Tom Montgomery (Courtesy of Chubbies)

What were you trying to convey with the brand?
That feeling you get Friday at 5 p.m., we want that to be the notion that our box carried when we delivered it to you. There are two pieces to that. The product—we’re always focused on product that is distinct and perfectly aligned with the weekend—and then the content. Even if someone is not purchasing we want them to have the ability to engage and talk with us. We were writing and creating videos from Day 1. Our photos shoots weren’t normal photo shoots. They started out with us going out and having fun and taking pictures of it. Now we’ve gotten a little more official, but our photo shoots are ridiculous. We built the business was off the backs of our friends. It just turned out that a lot of people were similar to our friends. So we think about our community as a conversation with our buddies. The way that I wrote the emails and all the content was the same way that I would write an email to my buddies, to try and make them laugh.

What were you guys doing before starting the company?
I was in venture capital for a few years. One of the guys was working at a tech startup. One of the guys was in straight-down-the-middle finance and then the last guy was in merchandising at The Gap so he had some contacts that we learned a little bit about the business from. But it honestly starts from the ground up. You do Google searches. you find people and talk with them. You hear about the garment district down in L.A., so you go down there and check it out. We do all the manufacturing here in the states so building that supply chain was from the ground up. Now the manufacturing chain is up to seven factories that are all just pumping out short men’s shorts.

Why was it important to make your product in the U.S.?
It’s huge for us as a company to be able to create jobs. These guys are keeping their factories on longer. They’re able to bring in more people so trying to be on the forefront of the rebirth of American manufacturing is awesome. That’s something that’s vital to the company. Our customer likes and appreciates it. The biggest thing is, it’s difficult. The supply chain for building wovens [in the U.S.] is practically non-existant.

What were the early days like?
We found a couple folks who could design the pattern for us and then could actually get that manufactured and made like 15-20 pairs. We took them out to the beaches of Lake Tahoe around the 4th of July and sold them. You either had people that were like “Hell yeah. I get it. Those are the shorts of our dads.” Or people were like, “We don’t want to see guys’ thighs. That’s not cool. Get off our beach.” So immediately there was an emotional chord that was being hit. We finally got to the point where we could manufacture hundreds of shorts and launched the website in September 2011. Then we really saw an inflection point in March 2012. We came into March like “It’s going down. We’re going to have enough product to get us through the summer.“ We sold out within the first few days. But then we were like "shit that was all the money we had” and so then we started pre-selling product—selling ahead of when we could actually deliver so that we could get the cash in and manufacture. Then we had to raise a little bit of money and leveled out for that winter, but then sold out again. Now, we’ve raised a little bit more money and now we’re at a pretty good state where we’ve been growing steadily each year.

Ridiculous photo shoots are a Chubbies signature (Courtesy of Chubbies)

Ridiculous photo shoots are a Chubbies signature (Courtesy of Chubbies)

How big is the company?
We’re at 34 employees. Our first real year of sales was 2012, and from the first to the second year I think it was 400% growth. Second to third year was something like like 60% and then this year ought to be another 40-50%. The cool thing is that you’ve got a humongous community of people that all react to our stuff. We have over a million fans on Facebook. We have a big Instagram community, a big Twitter community.

How did you grow such a large social following?
It was always something that was ingrained in the company from Day 1 because we were young guys and we were on [social media]. When we first put out products, you saw the links getting shared on Facebook. We saw a lot of organic community growth and as we were illustrating the fact that you didn’t need to be male models or be actual photographers, you also saw people start sending us massive amounts of photos. We get over 1,000 user generated photos and videos a week. In terms of the male selfie, dudes are down. It was really a community feeding itself and then us putting content out. We try to put out videos that contend with the viral videos on Jimmy Fallon’s page not with traditional brands. Videos that we try to make are getting millions of views.

How did you arrive at the design?
We grabbed a bunch of the shorts that we’re loving. I’m from Southern California and the ones that I was was wearing are like the old surf shorts with drawstrings hanging down, and neon colors. Some of the other guys were from Arizona and St. Louis and the Southeast, so they brought different perspectives. We laid out all the pairs of shorts we loved and took elements from them and then built the pattern off of that and it really hasn’t changed that much. We’re always trying to find ridiculous stuff and ridiculous photos online for inspiration.

What’s the culture like at the company? The mission of the company is to bring the weekend to all these people. That, in and of itself, is a fun task. We encourage people to take an hour of “vacation” every day, whether it’s going to hang out on our roof or going to get a workout, take some time to get a break and get away from stuff. Humor is a big part of the business and a big part of the internal value system. When we’re doing our Monday meetings, there’s funny stuff happening. Oftentimes, the idea that makes people laugh the most is the one that we end up doing.

The brand

The brand’s expansion into swimwear has been well received (Courtesy of Chubbies)

You are often described as the brand for frat guys, what’s your reaction to that?
It’s something where we’re just 100% open. We do not want to be exclusive. I just know those guys, the frat guys, were awesome. They found us first; they’re super enthusiastic dudes. I think that the way that we try to group people is often not representative of how an actual person is. We have a really diverse audience from being big in college towns to being big in large metro areas. For us the end goal is to build a humongous brand that affects everybody. It’s a welcoming brand. Let’s get everybody involved and have some fun. The weekend is not an exclusive concept.

As a shorts brand, what do you do in the winter?
We batten down the hatches and produce content. We still are selling a decent amount of product. Cyber Monday is a big day for us and the holidays. We have “future thank you cards” that we send out to moms that are basically a thank you in advance for the Chubbies. There’s going to be an interesting product coming out geared for winter that’s still in the world of shortswear. Then we’re also going to pioneer some uppers that are a little bit warmer that enable you to wear shorts year round.

Do you think you’ll continue to only produce apparel?
Tommy Bahama is a great example of a company that sells apparel products but they also run restaurants and bars. That works for their brand. For us I think we want to do the stuff that feels the most authentic for a guys’ lifestyle. There’s a big component of that that’s apparel. That being said we’re constantly looking for ways to add value. We have a store in San Francisco we opened in December as a holiday pop-up and then it worked so well that we decided to keep it open for the summer. We have an NBA Jam machine in there. We’re constantly hosting events there. We can base guys there on the weekend that are just having fun outside and passing out cups filled with coconut water to really enhance the neighborhood.

What is Chubbies perspective on fashion?
Men’s fashion is something that we didn’t relate with coming into this business. Honestly we didn’t quite realize we were a fashion company until somebody told us. We operated as a beer brand and we just happen to sell beer that you can wear, I guess. The way that we market and the way that we talk is very much ground in the everyman and not needing to have the washboard abs that you see in Abercrombie & Fitch. A great example is we’re working on a male model search right now that will be launching this summer. We’re going to try and build out our roster like the Victoria’s Secret Angels, but it’s going to be a diverse group of guys that are relatable. Then we will have a big fashion show that’s going to be part WWE, part Zoolander ridiculousness. That’s our take on a fashion show.


Justin Tejada is a writer and editor based in New York City. Follow him on Twitter at @just_tejada.

Playboy Social

Never miss an issue. Subscribe and save today!

Loading...