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Meet Tom and Preston from Chubbies Shorts!

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Chubbies Shorts launched in San Francisco in 2011 on a mission to make "the most radical shorts known to mankind." 

Four years later, they're inspiring thousands of customers across the U.S. to join Chubster Nation and celebrate the weekend in a pair of their unique, colorful shorts. As one our Final 3 in Small Business Big Game, we had to know more about their story and what keeps them inspired as small business owners day in and day out.

Take it away, fellas!


Names: Tom Montgomery & Preston Rutherford

Business: Chubbies Shorts

Started: 2011


How did you come up with the idea for starting Chubbies Shorts?

It was the most natural thing in the world for us to start a men's shorts company. We were four guys who always wore a particular style of shorts that were either handed down from our dads and uncles or found at thrift shops. When we wanted to find more, we couldn't find them anywhere to purchase. 

We had an idea and we wanted to see if other people would respond to these shorts the way we do. So, we made a quick batch of 20 pairs. We took them out to Lake Tahoe in California and sold them out of four backpacks, right there on the beach. They were so popular that we even had people offering to trade us their shorts for our shorts — they wanted to buy them right off of our bodies!

It was a really cool experience and it let us know that we had something with this product. The next step was defining a brand around it. 

Since we wore these shorts on the weekend and they defined weekends for us, we decided to create a weekend brand. 


What was the moment that surprised you the most so far about running your own business?

When we launched in September of 2011, we had no idea what to expect as small business owners. We were flying by the seat of our pants. At the time, we were just taking photos of each other throughout San Francisco and we had no idea if it would resonate. We also launched in the fall, which is not exactly the ideal time to launch a shorts company. It was just a little bit cold.

When March of 2012 rolled around, we kicked off the season with enough product that we thought could last us through the end of summer.

Turns out, we sold out of everything in two days.

We were shocked. Utterly, completely shocked by how much our message resonated with customers. We had to quickly turn that shock into producing a lot more shorts.

Fortunately, our community of customers was cool enough to participate in pre-sales, which allowed us to sell shorts before we even had them. That's initially how we were able to get our business going — our customers were willing to wait for us to create more product.


What is your favorite thing about being small business owners?

The opportunity to work with our best friends every day and create products for our friends is amazing. That's how we started this business four years ago, and we feel the exact same way today.

Having the freedom to build a business the way we honestly think it should be done, by making our products here in the United States, is by far the best thing about being a small business owner. We're living the dream by having control over our destiny and having fun every single day.


What is your least favorite part of being small business owners?

Every day we're challenged to learn something new that we didn't have any idea how to do. Whether that's payroll or being responsible for a growing group of people, there are stressful parts and there are moments of elation. But we wouldn't have it any other way.

We're pretty much doing exactly what we want to be doing.


 If you had a magic wand that you could use to make only one of your business challenges disappear, what would you use it for?

A magic wand that would make our products available in a limitless capacity everywhere in the United States would solve a lot of problems!

Manufacturing in the U.S. is a complex process. There is no end-to-end manufacturing. You have to get fabrics from certain places, you have to get it cut in certain places and you have to get it sewn in certain places. You have to be very operationally efficient to get all of that done and you have to find multiple factories that have enough capacity.

We would use a magic wand to own and operate Chubbies Manufacturing so that it just rocks and rolls and we don't have to worry about it.


How do you keep the passion alive in your business? How do you stay inspired day in and day out?

We're very lucky in that we're extremely passionate about what we do. We feel fortunate to have had wonderful growth with our business up until this point. But there's still so much more we want to do.

Every morning when we wake up, we're asking ourselves how we can improve our business. Is there a new way we can manufacture in the U.S. more efficiently? How can we make our audience appreciate their weekends a little bit more? How we can bring a smile to someone's face in their Facebook news feed or through an email?

We have the opportunity every day to do that better and better. That's what makes us more passionate about what we do, day in and day out.


If you had one piece of advice for a small business owner who is just starting out, what would it be?

Find your passion. There are a lot of ups and downs when it comes to running a small company and building a team. You have a lot of alternatives if you're not fully invested in what you're doing.

Find the passion in what you're building and commit to it. That is fundamentally the most important thing to do as a small business owner.


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