Vintage Sports, Unique Stories: Inside the World of Pro Seller Zach’s Trunk Show
In our Pro Seller series, we spotlight a standout seller from Sideline's talented and ambitious community and offer readers a look at their process and story. This month, it's all about vintage sports gear with Zachstrunkshow.
Zach Wolpoff never expected his passion for thrifting and sports collectibles to become a full-time career. But after leaving a desk job he despised in April of 2018, he dove headfirst into the world of sports resale—and hasn’t looked back.
"The first things I sold on SidelineSwap was a Space Jam SGA jersey from UMass Lowell and a Clint Dempsey Nike T-Shirt," Zach says. "I remember my dad being so impressed! Those first few sales were big moments for me."
Zach was hooked. He jumped head-first into sourcing inventory, scouring thrift stores, estate sales, and online marketplaces for the coolest sports gear he could find. And when the pandemic hit in 2020, his business took off.
"Everyone was at home cleaning out their garages and attics, so I was finding all kinds of amazing, unique vintage stuff. People who lost grandparents ten years ago and never worked through their stuff suddenly had time to go through it all. So, fifty hats from the '70s and '80s would suddenly appear on Facebook Marketplace or Craigslist, and I would buy, buy, buy. I got a lot of inventory during that time. It looked like that scene in Trading Places. One of Eddie Murphy’s finest films. I still bet my brother $1 on things."
Part of the thrill for Zach is finding gems hidden in unexpected places.
"I find a lot of lacrosse and smaller soccer jerseys in the women's athletic department. Especially the practice jerseys and the reversible pennies. People think, 'Oh, this must be women’s because they’re tiny.' I've found great things that way, including a Hong Kong National Soccer Team Jersey, which is incredibly rare to find, and a New York Lizards Game Used Al Maione Signed Jersey."
Today, Zach's inventory includes thousands of items—with hats making up about 60% of his total stock. By researching what’s available on the second-hand market, Zach has keyed in on trends that made a difference to his customers.
"Hats with leather straps are incredibly hard to find these days. Most modern hats use cloth, but back in the day, leather was the standard. So, when I come across a vintage hat with that leather strap, I know it's a special piece."
Beyond an impressive hat inventory, Zach’s developed a keen eye for spotting hidden gems, like the Colin Kaepernick Super Bowl champion jersey sample he found at Goodwill.
"Fanatics had dumped a bunch of stuff at a Goodwill by me, and this Kaepernick jersey was just sitting there. In another universe, the 49ers would have gotten that holding call on 4th & goal and won Super Bowl XLVII, and this jersey would have been in stores. It's a unique piece of sports history."
Zach's passion for preserving sports history shines through in the way he curates and presents his inventory. He takes pride in providing detailed, well-researched descriptions that give buyers the full backstory of each item.
During his ongoing quest for grails, Zach once found a former University of Delaware Defensive End Pat Mulhern jersey. He knew it was an obscure find immediately but couldn’t have guessed how it would connect him to the player’s legacy.
"Mulhern was known as the 'Parachute Man' because he loved skydiving and even parachuted into the Phillies' opening-day game in 1977 to deliver the game ball. When Mulhern passed away in 2022, his sister contacted me about the jersey I'd found."
Caption: Mulhern mid-air. Taken from the NFL Films production “Parachute Man”
Zach had stumbled upon Mulhern's rare jersey at a Virginia thrift store, not realizing its significance then. But once Mulhern's sister contacted him, he was able to connect the dots and provide her with a piece of her brother's legacy.
"It was such a meaningful moment. Mulhern's family and friends were so grateful to have this jersey to remember him. Pat always talked about his football career, but his family had nothing to show for it. That's the kind of thing that makes this job so rewarding."
Another benefit to this type of work, Zach says, is the freedom and flexibility it provides. As a full-time reseller, Zach gets to determine his hours, set prices, and choose what he wants to sell.
"I'm 100% in control. If I want to work late at night, I can. If I want to take a day off and thrift, I can do that too. I love traveling and finding new items in different markets across the country.”
Of course, managing a high-volume resale business comes with its own set of challenges. With almost 5,000 items listed on SidelineSwap, and even more in storage, Zach has to get creative with his inventory organization, transitioning from rolling racks to a system of labeled boxes and containers.
"It was a mess at first—I couldn't find anything. But now I have everything labeled and organized in numbered boxes, so I can quickly grab what I need when an order comes in."
That attention to detail and Zach's commitment to customer satisfaction is what sets him apart in the crowded sports resale market. Zach takes pride in carefully packaging each item, quickly shipping orders, and ensuring buyers receive exactly what they expect.
As for the future, Zach has no plans to slow down. He's constantly on the hunt for new inventory and ways to make reselling a sustainable business.
"I have a rule of thirds. If I buy something for $10, I need to get at least a minimum of $30. That way, I not only get my money back, but the fees are taken care of, and I make a profit."
Zach has made over 2,000 sales on SidelineSwap. On a typical weekday, Zach says he averages about five items going out the door. On busy weekends, he's shipping anywhere from 10 to 20+ items.
The highest margin item Zach has ever sold was a jersey from a charity soccer match for former Bulgarian National Team player Hristo Stoichkov's 50th birthday.
“Stoichkov is regarded as one of the best Eastern European strikers ever. For his 50th birthday, Stoichkov had a charity soccer match with a bunch of his old friends and teammates, including player Peter Nowak. I managed to find Nowak's jersey from that game for just $5 and resell it for $1,000!"
The Nowak transaction speaks to Zach's keen eye for valuable sports memorabilia and his ability to research and present items in a way that maximizes their resale value.
"I'm not trying to reinvent the wheel. My goal is to keep growing my inventory, improving my organization, and providing the best possible experience for my customers.”
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Interested in selling more on SidelineSwap? Learn more about the perks of upgrading to Pro and read more Pro Seller stories here.