PILSEN – Diego Astorga drives to work like many Chicagoans. But the bright yellow bus he commutes in is also his job.
Astorga, 29, is the entrepreneur behind WellRounded, a resale boutique on wheels. Inspired by vintage Americana, Western wear and modern apparel, Astorga describes it as a food truck but with clothes.
He launched WellRounded in summer 2022. After a few successful stops at local markets, he briefly pivoted away from his full-time job to devote more time to the business. Now going into his second year, and after several setbacks, he is back on the streets of Chicago to build his brand with the aim of one-day finding a permanent home for WellRounded..
“A lot of people consider me creative, a pioneer, innovative. Just for the fact they’ve never seen a retail bus used [this way],” Astorga said in a recent interview. “When I feel like I have self-doubt, people always remind me that it’s a clever idea. There is a lot of support.”
Astorga is from Tijuana, Mexico, but grew up in Kansas City, Missouri. His mother, Patricia Perez, moved her family to the United States when Astorga was 4, he said.
A single mother of three children, Perez started a successful hair salon in Kansas City. Owning her own business allowed Perez the flexibility and financial means to support her family, Astorga said.
“I’ve always been under an independent woman who just figured it out and gave me the motivation to do my own thing,” Astorga said. “She planted the idea that you’re not gonna make better money than being your own boss.”
Astorga got his first job in retail when he was 17 as a sales associate at Abercrombie Kids and continued to build his resume at a luxury department store Halls and later Marine Layer. But the thought of having something of his own always sat in the back of his mind, he said.
He didn’t think he could achieve that in Kansas City and knew he needed a change, he said. In 2017, he talked to the district manager at Marine Layer about a recent trip to Chicago. He felt the energy of the city and thought it could be the fresh start he needed. With their encouragement, he packed up his belongings and made the move. Unfortunately when he arrived the transfer hadn’t been processed and his district manager wasn’t taking his calls.
“I was kind of burnt out. Anybody who knows Kansas City knows it is a small city. Same old, same old, there is nothing new anymore, so I needed a new chapter,” Astorga said. “I reached out to [the district manager] to make that happen, and when I got here I was left with no job.”
In a new city with no connections, Astorga knew he would have to pivot. A short-stint in real estate helped him get familiar with the city while a few modeling gigs paid the bills until he found his next full-time position in retail, he said. He started at Saks Fifth Avenue, made his way back into Marine Layer and finally landed at Shinola Detroit, a luxury watch brand, he said.
He had a talent for connecting with customers and worked hard to prove his worth aiming to move into a management role one day, he said. But after four more years he found himself roadblocked from any meaningful career advancement with the positions he was applying for going to other employees, he said.
Astorga was getting his oil changed at the mechanic when a bright yellow bus on the lot caught his eye. He remembered the movie Chef where Jon Favreau leaves his restaurant job and an unsupportive boss to start a successful food truck. For Astorga, the thought of proving his managers wrong and creating a business for himself was too good to pass up. Motivated for a change, he called the owner of the bus.
“During the pandemic, the bus was still there so I thought why not pull the trigger and just buy it and see where it goes?” Astorga said. “Instead of me finding it, it found me.”
Astorga bought the bus for $4,500 in October 2021. It was a decommissioned Spirit Airlines shuttle the owner said just needed a new battery. As it turns out, the battery would quickly drain until the dashboard shut off completely and the engine died. Three batteries and a painful tow later, the bus was turning out to be a money pit, he said.
Just on one trip to the mechanic, the engine died four times, requiring Astorga to pull over on the highway to jumpstart it, he said. It would stay at the mechanic for another six months, he said.
“They had that bus for about half a year and I can only tell you that I was anxious, nervous, confused and slightly angered cause it just took way too long for what the problem was,” Astorga said.
During this time, Astorga focused on getting everything else in line for the eventual launch of the business.
With a boom of eco-conscious shoppers and his experience in retail, he knew a resale boutique was the way he wanted to go. He built up stock from antique markets, wholesalers and Salvation Army stores. He researched what business licenses he would need to operate legally and created branding for what would become WellRounded. The name was inspired by his ability to connect with people from all walks of life as well how he always adapted to changing circumstances. His girlfriend Kelsey Conner helped him brainstorm and design a western influenced typeface that would pop against the yellow bus.
Astorga finally got the bus back in May 2022. He redid the flooring, installed industrial pipe clothes racks, and applied a decal with the name WellRounded on the outside of the bus. WellRounded debuted at the Chicago Vintage Festival in July 2022. The bus was a hit and he made $3,000 in that weekend alone, he said.
Later that month, he went part-time at Shinola so he could invest everything into WellRounded.
During his first summer, Astorga took the bus out three times a week in Pilsen, Bucktown, the South Loop and Logan Square. If he wasn’t at a farmers market or vintage fair, he would find another thrift store to post in front for the afternoon hoping to pick up some customers, he said. He didn’t have regular business hours, but would keep his followers updated with a post on instagram once he was set up for the day. Twice a month, he took the bus out in search of new stock taking into consideration what was selling well.
“I heard a quote saying if you want to see where your business is going to be, try to do it as much as you can in six months and see how that goes,” Astorga said. “One thing led to another, and I just built momentum. Now I have a bus with clothes and a fanbase.”
Currently, Astorga is working full-time again at Shinola and operating the bus on the weekends. He learned a lot in his first six months of business, but needs a steadier stream of income while he continues to build up the brand, he said. Astorga’s experience in retail and a curated eye for apparel gave him a strong foundation for his business. But a mobile business has its own unique challenges, he said.
“How do people find you again?” Astorga said. “They say [the] internet is the best way, but as an independent employee, it’s hard to maintain the bus, an online presence, personal life and my job.”
He launched a website, but keeping it updated with the cycle of new and sold inventory was time consuming and had little payoff, he said. Other obstacles have been the harsh Chicago winters, further bus repairs and the always elusive parking. Also bathroom breaks.
“The bus does not have a bathroom, so you have to be dehydrated beforehand,” Astorga jokes. “ Don’t snack, don’t eat. If you're a faster, this is the business for you.”
Traveling around the city, he wants to build name recognition and a customer base with an eye toward opening a brick-and-mortar vintage shop one day.
“Out of so much disappointment and failure…it gave me that drive,” Astorga said. “I was an underdog and now I’m becoming an entrepreneur.”
On a recent outing for WellRounded, racks of clothes jostled against the walls, held in place by bungee cords as a mirror in the back tips over. “I should have tied that down,” Astorga said, while pulling over to his final destination in Wicker Park.
The windows are propped open with large white tree branches, western style boots are lined up on the floor, and racks of leather jackets and vintage tees are pushed against the interior of the bus. Astorga plops down in the driver seat and swings open the doors.
“Now we wait,” he said.