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Meet Ted Upton of Cheeky Fishing in Watertown

Today we’d like to introduce you to Ted Upton.

Thanks for sharing your story with us Ted. So, let’s start at the beginning and we can move on from there.
Cheeky Fishing was founded in 2009 out of a shoebox apartment in Boston. I had moved to the city (I’m originally from Maine) after graduating college and was working for the man in a downtown corporate firm. Three lifelong buddies of mine we’re doing the same. After a couple of years of the corporate grind, we’d all had enough. All passionate fly fishermen, we wanted to start our own thing in an industry we loved. We pooled what little resources we had and founded Cheeky Fishing, working nights and weekends at restaurants and fly shops to make ends meet while we worked on our business during the days. We had the technical expertise to make fly fishing reels, but we had no money, so it was a slow process. It took us nearly two years to bring our first products to market. Our goal was to manufacture a technologically advanced fly fishing reel and market it to an emerging demographic of anglers looking to push the limits of the sport. We succeeded in doing just that, and fast forward 9 years, we sell our products on six continents to some of the largest retailers in the world, including Bass Pro Shops, Cabela’s, L.L.Bean, and hundreds of other specialty fishing dealer locations around the world.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Starting a business is never a smooth process, at least not that I know of. We’ve had countless challenges along the way, but that’s what makes our business what it is. One of our biggest hurdles was transitioning manufacturing facilities in the second year of operations. We outgrew our first facility fast, and had to figure out how to transfer our entire production process in a matter of months, all without losing customers in this critical early stage of our business. There were definitely some sleepless nights…

Please tell us about Cheeky Fishing.
Cheeky Fishing manufactures high performance fly fishing reels that are known for their innovative technology and edgy designs. Technology aside, one of our calling cards is our use of loud color combinations. We take a lot of our inspiration from the ski industry, which has no shortage of bright and bold designs.

In 2015, we launch a second “sister-brand” called Wingo Outdoors. Wingo manufactures a variety of outdoors accessories, including belts, hats, socks, totes, tees, lanyards, dog products, etc., in outdoors and fishing themed designs. We are very proud to operate both brands side-by-side in Watertown.

Do you look back particularly fondly on any memories from childhood?
It won’t surprise you that my favorite childhood memories are on the water fishing. In particular, time spent with my family at an extremely remote lake in Western Maine. Hands down still my favorite place on planet earth to go fishing is that little lake deep back in the logging roads of remote Maine.


  • 11 models of Cheeky Fly Reels ranging from $129-$525
  • Wingo Outdoors accessories ranging from $8-$35

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