Life, Liberty and the Pursuit of Happiness

A COUPLE OF WEEKS AGO, we sat down with Kyle Hency, one member of the quadfecta that founded Chubbies, a weekend brand best known for their skimpy short shorts. We're sure you've seen boys donning these ridiculous and radical shorts around campus, but little did you know that the brilliant minds behind the Chubbies empire all went to Stanford. The four, Kyle Hency, Rainer Castillo, Tom Montgomery and Preston Rutherford have been tight since their first days on The Farm. They most definitely lived the Frat Star life as members of KA, Sigma Nu and AKPsi . Together, they've been living the dream, and striving towards Life, Liberty and the pursuit of Frattiness.

The boys sent over some shorts for us to check out- take a look at some of our very own Stanford boys in these Boomshakalaka-worthy shorts

Pulse: What is Chubbies all about?

Kyle Hency: We are a weekend lifestyle brand for the younger generation. We started all of this by creating Chubbies, the shorts, and we are slowly going to expand and build out the rest of The Weekend…anything that a guy would throw in a weekend bag, to have the most epic weekend ever is fair game for us. That’s the bag itself, the tank top, the hat, the shoes, all of that…


P: What’s your target age range?

K: It’s evolved over time, but down the fairway, its anywhere from 15-30 years old. It’s that market, and I think it’s because we know that market. I think there are a whole bunch of other guys that are digging what we’re doing, and that’s one of the things that we love the most. Getting a dad to come see what you are doing, and viscerally be excited about getting his shorts… is one of the coolest experiences.


P: How has Stanford culture influenced Chubbies?

K: The three of us, myself, Tom and Preston were KA’s and then Rainer was a Sigma Nu… super social, you can imagine the summer evenings playing drinking games outside of Lake Lag, and in Rainer’s case, outside of Sigma Nu, you know, in your shorts, and your Hawaiian -– the best times of your life.

If you look at the costume element of what we do, think about Special Dinners at Stanford. Our team still has Special Dinners, . We have a costume closet, and all of those things are fully in tact and a part of us. So those things are very directly Stanford-related.

At the end of the day, we are four good buddies from college; we all went our own ways. We all got to a point in our own careers where we said, "We gotta control our own destiny".


P: What are some of the most memorable times that you’ve had at Stanford? What’s your most epic weekend?

K: We can talk about my most epic day-- very much an inspiration for what we are doing, when I look at this from my own personal perspective… my specific day is this day at KA called Endless KA that I also organized for 3 years. I would wait for that day all year. That was the 10 am to end of day- retro shorts, backwards hat, a shirt sometimes, a tank most of the times, just doing my own thing.

When I think about the picture we are painting for people as a brand, I think about that alot. Being outside with all your best friends, the sun and the warmth and just hanging out outside. Just the idea that there are guys on campus, in our gear, doing the exact same thing, makes me so excited.


P: Did you have any doubts about mixing business with pleasure?

K: We’re really, really close friends, and so I would say it’s almost been crazy that we haven’t been more contentious, and we align naturally on so many different things. I think it gets harder over time, when… you have to start putting systems in place, so you feel like everyone’s connected and working together. So much of our brand, from the beginning, was about us being four buddies getting together. Our first 25-50 investors-- of that group 95% of them were just our best friends and probably 75% of them were from Stanford. And so, there was always something so cool and community driven. We founded this business as friends, to allow groups of friends to go out and have good times in this world, and used our friends to help us get there.

I don’t question it at all; I would do it again in a heartbeat. …. I think there are distinct advantages to starting a company with one, or two or three of your close buddies, or gals.


P: How would you advise kids at Stanford to do something like this?

K: You gotta be really interested, and you have to love what you are doing. So for us this was [about having] the ability to build a brand about the weekend, about the good times we’ve had in the past, and we can enable people to have more good times.  So that was something that we were able to have a ton of passion about. …It just makes it easier in the first year, when things are hard, when you try to get things going. There [are] so many points when you give up, and so when it’s really hard, and in that moment in time, you want to think “oh I really love this, I can’t give up”.


P: If you were to give your 20-year-old self advice, what would it be?

K: Don’t waste your time in Investment Banking and Private Equity, answering to The Man. Trust yourself in your abilities and get out in the world and start a business as soon as you can. 

I think depending on where you are from in life, college has the potential to put a lot of financial burden on you, and so that dictates how risky you can be in the grand scheme of things.  And so I think in a world where we can mitigate that sum, you have more and more people taking chances and chasing the things they’ve loved since day one…I think a lot of people tend to herd to the most conservative, highest upside things, but I think being a little more aggressive on the entrepreneurial front isn’t a terrible thing.  


P: How did you stop answering to ‘The Man’?

K: Each of us knew that we were competent folks, we wanted to control our own destiny, be our own boss, live how we want to live. We saw that we had a very unique opportunity to work on this where nobody would be as aggressive, as intelligent and as well situated to get after this opportunity.


P: What skills do you think helped to get you where you are today?

K: All of us have a natural tendency to put our heads down and work hard, and are willing to roll up our sleeves, put some elbow grease on things, and just get the job done. I think that that’s very much something that comes from athletics, and it comes from being in an environment where people all around you, are really intelligent and driven and you wanting to compete… I think that there’s an element of that that’s helpful, particularly in business. But really the thing that’s most helpful is wanting to work really hard and get the job done. All four of us really aligned on that, our employees are very aligned on that, and that’s something that we talk about. We’re all kind of goofy and funny, and it’s just kind of funny and out there, and it’s just a natural extension of who we are…


P: How are you guys dealing with so much demand?

K: We are continuing on focusing on being the shorts guys. If you are going anywhere on the weekend, for shorts, swim trunks-- anything in that vein-- we really want to be that guy. So the vast majority of our inventory is shorts. Over the next two to three years it will continue to be that. This year we launched tops, Hawaiians…we have a couple of experiments that we will come out with later in the year, but that will be very small. [We’re] just getting a sense of how people perceive us and whether they like us, and then we will start to scale on the things that work.


P: What sorts of people are you looking to add to your team?

K: Content marketing folks, general marketing folks. We are looking for front-end designers… in Photoshop. It’s going to be an exciting year of recruiting, which is not something we have focused on historically. All of our employees are one degree of separation of friends.