Student, Athlete, Businessman: The Rise of Jack Holway’s Clothing Enterprise

A man in a white sweatshirt stands in front of a jean jacket and two graphic T-shirts hanging from a lofted bed.
Antioch, Ill., sophomore Jack Holway stands next to several articles of vintage clothing hanging from his bed. Holway sells these clothing items out of his dorm online, which “probably ranges to 50 items a week” (Photo illustration by Killian Altayeb).

Hours of homework, attending lectures, writing papers and managing free time are only some of the activities that accompany the life of a college student. However, one Albion lacrosse player, on top of academics and sports, finds time to nourish a growing clothing business, which operates right out of his dorm room in Seaton.

Jack Holway, a sophomore from Antioch, Illinois, has “always been big on fashion.” It wasn’t until winter break last year, however, that he decided to turn that interest into a full-on business. 

“I went to the Goodwill bins once with my friends, and it was fun,” Holway said. “Then a bunch of my friends wanted me to help them build an outfit, so I just sold them an outfit I made from Goodwill bins.”

According to Holway, what started as friends wanting fashion advice transformed into a “community” of people who would “come over to my garage and buy stuff.”

“Once my online picked up, I stopped doing it in person,” Holway said.

However, Holway’s method of picking up clothes from Goodwill wasn’t an option once he returned to Albion for the spring 2025 semester.

“I would have to go to garage sales I found on Facebook, and I met a good amount of people around here,” Holway said.

Garage sales aren’t the only way that Holway acquires his merchandise here in Albion.

“Sometimes I’ll go on auctions,” Holway said. “I’ll buy the stuff for like a dollar to $5, and then I resell it for like $30.”

Holway added that managing a business alongside academics and sports can be “kinda hard,” but the mailroom clerks in the post office help him out to make the whole process “really easy.” One of those mailroom clerks is Mike DeWaters.

“A lot of students actually send things out,” DeWaters said. “Jack, that I know of, is the only one with a business.”

DeWaters added the process of sending a package out is actually “pretty easy,” with a bin of recycled boxes at students’ disposal to package whatever they’re sending out.

“I get all the shipping supplies from Walmart, and then I’ll pack them all and then just drop it off (at the post office) after one of my classes,” Holway said.

Back in Antioch, Holway said he runs a larger-scale operation.

“I have an entire little shop in my basement,” Holway said. “And my mom actually helps out a ton with this; she ships out the stuff that sells from home for me right now.”

Holway said he ships out around seven articles of clothing from his dorm room each day, which then “ranges to like 50 a week.”

One review on Depop described Holway’s business as “easy to work with,” and their purchase as “better than described.” Another five-star review said their shirt was “probably the best item I’ve bought on here.”

A screenshot of a review for an article of clothing—a black t-shirt with a soccer ball merged onto an alien head. To the right of the t-shirt is a username reading “@fabian93”; below the username are five red stars and text reading, “Seller is easy to work with & shipped quick! Item better than described 10/10.”
A screenshot of a review on Holway’s Depop page. This is one of 318 reviews on Holway’s page as of Monday, with a majority of them being five stars (Photo illustration by Kai Taylor).

Boasting hundreds of five-star reviews on Depop, Holway has sold over 1,000 articles of clothing on that platform alone. On Whatnot as JacksGrails, Holway has an average rating of 4.8 out of 5.

“I’m just about making money,” Holway said.

About Kai Taylor 11 Articles
Kai Taylor is a freshman from Beverly Hills, Michigan and an english major at Albion College. He is working at The Pleiad to build expereince in the realm of journalism and hopefully pursue it as a career. He loves watching the Detroit Lions, talking walks in nature, and reading. Contact Kai via email at [email protected].

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