Building a big business in small batches

Wears Woody apparel brand founder chases his dreams while giving back

Business
 
Mike Norwood Gilliam Center talk1

SUMMARY: For Mike Norwood ('89), what started out as a fun summer side hustle in 2011 has fully matured into Wears Woody, an upscale apparel manufacturer and multichannel retail brand known for its “bold coastal style.” The company sells men’s and women’s sportswear, hoodies, jackets, hats and tees, all proudly made in America. Wears Woody donates up to 3% of sales year-round to organizations working to improve the lives of people with diabetes and to help fund a cure.


Mike Norwood (’89) lives with Type 1 diabetes. Growing up in the 1970s and ’80s, there were few treatment options available. Urine strips and insulin injections were part of his daily routine.

“When I was at JMU many years ago, that was a bit of a challenge to put it lightly,” Norwood, the founder of the Wears Woody apparel brand, told a group of students at a Gilliam Center for Entrepreneurship Open Coffee event in November.

After graduating with a degree in Marketing, Norwood started out in sports marketing and licensing before being drawn into the medical device industry. “I wanted to work with and help people just like me and believed I could make a difference,” he said. 

For the next dozen-plus years, Norwood sold thousands of insulin pumps and launched the first generation of continuous glucose monitors, both of which are now the standard of care in diabetes management. “Fortunately, I did what I set out to do and did pretty well,” he said of his time with industry leader Medtronic. But with the demands of travel and remote bosses and the increasing dysfunction across the health care spectrum, he came to realize he “wasn’t much of a corporate guy.” Norwood’s midlife crisis was in full effect, and he felt it was the perfect time to scratch a burning itch to venture out on his own. So, at age 40, he enrolled in graduate school at Babson College to study entrepreneurship.

While taking a class in Brazil, Norwood discovered Havaianas, a flip-flop brand looking to gain a stronger toehold in the U.S. market. He made a trip to New York City to pitch the company’s U.S. leadership team: “If I bought a funky old beach wagon, drove it around and sold your line out of it, would you make me a retail partner and pay me?” The company said yes, and Norwood secured a street vendor permit from Falmouth, Massachusetts, on Cape Cod for just $10. With his 1990 Jeep Grand Wagoneer — aptly named “Woody” — stocked and loaded, his mobile retail startup was born.

“The original idea was to bring our store straight to the people and not assume they would come to us, especially on a hot beach day,” he said. “We would park in front of the ice cream shop, liquor store, raw bar — wherever we could set up without getting snarled at by brick-and-mortar merchants too much.” His best sales days were when he parked along the street of the Martha’s Vineyard ferry terminal to target vacationers with plenty of disposable income. “We would sell $2,000 worth of flip-flops in a weekend,” he said. With proof of concept, his business was rolling.

Mike Norwood Wears Woody van
Norwood and his crew drive a 1990 Jeep Grand Wagoneer, aptly named “Woody,” and set up shop at sports and lifestyle events across the country.
PHOTO COURTESY OF WEARS WOODY

What started out as a fun summer side hustle in 2011 has now fully matured into Wears Woody, an upscale apparel manufacturer and multichannel retail brand known for its “bold coastal style.” Today, Norwood and his crew still drive Woody and set up shop at the finest sports and lifestyle events across the country — destinations that attract Wears Woody’s target clientele, which includes parents and young adults who play and watch sports and love the outdoors. 

“The idea of talking to your customer, interacting with them, shaking their hand, getting their email, getting their text [number], allows you to — very efficiently and very cost effectively — remarket to our fans,” Norwood said. “And that's how we've built the company — old school, organically.”

In addition to its nonstop road show, the company’s merchandise is available online and at select retailers across the Northeast. It also has a burgeoning B2B custom apparel segment that allows organizations to design merchandise that is made from scratch, just the way they want it. 

The company's product line has graduated from flip-flops to men’s and women’s sportswear (half zips, polos), unisex hoodies and jackets, all proudly made in America in Mike’s backyard in Boston. The company also sells headwear and tees. 

And, for all of us who bleed purple, Wears Woody recently released a line of JMU-licensed products that are available for sale at wearswoody.com, with plans to be in the JMU Bookstore this fall. 

Mike Norwood Gilliam Center talk2
Norwood makes a point during a presentation to students at a Gilliam Center for Entrepreneurship Open Coffee event in November.

Along his journey, Mike taught himself a new trade defined by core values that are beginning to separate his story and brand from the pack.

Interestingly, his decision to make Wears Woody’s finer goods in America was not just out of his pride for country, but also a financial one. He calculated that “small batch” domestic production — making dozens of units at a time instead of thousands — across a limited set of styles and colors was the most economical way to go. “These days I like to joke that everything is bulk-produced in Bangladesh. We believe in small batches in Boston,” he said.

Wears Woody’s mission is truly personal and a core value that not many companies can claim. The company donates up to 3% of sales year-round to organizations working to improve the lives of people with diabetes and to help fund a cure. “We take the percentage off the top line [sales], not the bottom [profits], so when people make a purchase, they’re making a donation. And we think that's a very powerful thing.”

In November, Norwood described to students the humbling experience of transitioning from a lucrative career in medical sales to a mobile retail startup. “It was a definite adjustment. You can’t stay in four-star hotels. You have to lower your expectations a little bit.”

When you’re starting out as an entrepreneur, he said, “bet on yourself. It really shouldn’t be about the money at all. It should be about your vision and where it may take you.”

Norwood draws inspiration from iconic brands like Coca-Cola and Amazon, which started out small and grew their concepts over time. “I heard Warren Buffett say recently that Coca-Cola sold 25 bottles of Coke in the first year. Now it’s an empire, right? [Jeff] Bezos was selling books on Amazon. … Hopefully we'll turn into a retail and apparel empire.”

He advised students against waiting for the “perfect” time to launch a company. “Many of us think the stars have to be aligned and everything,” he said. “No. Give that up. That’s not going to be the case. … I think the people who really make it don’t [have any regrets]. You’re all in.”

Norwood said he is fortunate to have worked in an industry that allowed him to help other people living with diabetes. Now he’s doing the same as an entrepreneur.

“Giving back is a big part of who I am.”

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by Jim Heffernan ('96, '17M)

Published: Friday, February 28, 2025

Last Updated: Friday, February 28, 2025

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