Chubbies: The Success Story of Shorts with Unique Design

Igor Izraylevych
Startup’s Success Stories
3 min readDec 13, 2018

There were two things that connected four Stanford graduates — friendship and their love for shorts. Back in college Kyle Hency, Rainer Castillo, Preston Rutherford, and Tom Montgomery used to find retro short-shorts in thrift stores or hand them down from their dads — so they always stood out from the crowd wearing unique-designed pieces of garment. And luckily their love turned into a successful company with thousands of devoted customers all over the world — read the story of Chubbies success below.

How it all started

After graduation four friends pursued nine-to-five jobs, until 2011 when they understood they want to share their love for shorts with the world. They wanted their clothes to be associated with weekends and chilling out. All of them were somehow involved in the garment industry before — Castillo worked in The Gap and Levi’s, Hency was an analyst in online sales, Montgomery worked with IDG Ventures. And their experience helped guys a lot — founders knew not only how to produce clothes, but how to promote it as well.

Young entrepreneurs decided to test the water by wearing shorts with their own design to the Fourth of July beach party. Their friends were wearing red, white, and blue shorts, while guys hit the beach in their unique Chubbies. Few pairs they took with themselves were sold out immediately right on the beach. After that, they started a serious work on the project: building a website, making a few hundreds of shorts, selling their merchandise.

The success

The website was launched in September, showing quite good sales results. Founders started preparing for the spring season, so they emailed college fraternity presidents and head of other campus social groups introducing shorts to them.

Shorts with a fresh and unique design that helps to express a person’s individuality were welcomed warmly by college guys. If you walk around any big college campus today, you will see at least a few students chilling in Chubbies.

Since Chubbies is constantly developing and improving:

  • founders raised $16 mln of investments
  • additional sizing, options, and items are offered
  • beyond shorts, the company is producing underwear, swim trunks, shirts, jackets, and hoodies
  • over 40 employees work in Chubbies
  • it has a brick-and-mortar retail store in San Francisco.

Why did they succeed?

Creating a great product is not enough, you have to make people want to buy it, and Chubbies is great at it. There are a few reasons for the company success:

  • building the brand — product design and brand is all about chilling and enjoying life;
  • fearless promotion — guys weren’t afraid to write college fraternities directly telling about their product;
  • high-quality marketing — founders hired special editors to create outstanding and inspiring content;
  • attention to details — everything from order confirmation letter to package in which a client gets their purchases expresses the spirit of the brand;
  • Instagram page — politics of Chubbies is “Make your client a hero” which you can clearly see in their Instagram profile — pictures of sportsmen, divers and bikers wearing short-shorts.

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Igor Izraylevych
Startup’s Success Stories

Co-founder and CEO of S-PRO, Entrepreneur, Advisor & Expert in Mobility & IT Strategy. Custom solutions for enterprise and startups http://s-pro.io/