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Yinka Ogunsunlade's earliest eBay memory is bidding on a watch as a teen. "It was one of those cubic zirconia style watches," he told Business Insider. "I won the auction and actually went to the post office, got a money order, and put it in the mail." Ogunsunlade, who grew up in Maryland, frequented eBay throughout high school and college: "I bought hundreds and hundreds of items — football jerseys, basketball jerseys. Jerseys were kind of all the rage in those early 2000s." It wasn't until he was home for the holidays during his first year of law school in 2005 that he considered listing items as a seller. "My mom always got the most Christmas gifts. She always had excess," he recalled. That particular year, she received a perfume set she wasn't going to use. Out of curiosity, he listed it on eBay. "I sold that item fairly quickly, and thought, 'If I can sell something I know nothing about, I'm sure I can sell items that I know a lot about.'" He started listing items from his own closet. "There was no start-up cost," he said, meaning anything he sold was pure profit. After working his way through his closet items, Ogunsunlade needed to source inventory if he wanted to continue reselling on eBay. Having received "the shopping gene from my mom," he said, there was a simple solution: "I love to shop, I love the thrill of the hunt, so I was like, let me go to these stores and see if I can find something to sell." From bringing in enough to cover his cellphone bill to building a six-figure business Throughout law school, Ogunsunlade had two go-to stores for sourcing deals: Neiman Marcus Last Call and Saks OFF 5th. To ensure he could turn a profit, he'd spend time browsing apparel and take photos of items along with their price tags. Then, he'd drive home, pull up eBay on his computer to look for what similar items sold for, and return to the department stores to buy the ones with the best profit margins. Finally, after buying the items, he'd take photos and list them on eBay with a detailed description. Related stories Business Insider tells the innovative stories you want to know Business Insider tells the innovative stories you want to know "Then, it's in the eyes of millions of people around the world," said Ogunsunlade, noting that his process is much more streamlined today. Thanks to smartphones and the eBay app, he can price-compare while shopping. He also sources items online now, which saves him time and gas money. His initial goal was to earn enough from eBay to cover one monthly bill. As a law student, "every sale counts, whether it be $30, $5, or $10," he said. While his sales fluctuated throughout his first few years on the platform, he brought in enough each month to pay his cellphone bill. "That was a light bulb moment: The money that I make doing something that I enjoy — searching for and buying items — can alleviate some of my expenses." From there, Ogunsunlade set a goal to grow his side hustle income every year. Since listing his first item 20 years ago, he has gradually built a six-figure reselling business, which he named Fashionably Legal. Between September 2024 and September 2025, he did $120,000 in sales on eBay, according to a screenshot of his seller hub dashboard. He's experimented with various product categories, including business attire, but has had the most success with athletic sneakers and apparel. It's the category he knows best. Plus, "everybody's always going to need a pair of running shoes or walking shoes or less formal, athletic wear," he said. There's more of an ebb and flow with the business attire category: "Especially when COVID came around, people weren't going into the office and weren't even wearing business attire, so I saw a drop in people searching for neckties and formal wear online. I don't see those types of pronounced dips in the athletic market." He pays attention to seasonal trends. At the start of football season, for example, he stocks up on cleats. He's learned that, "once July and August roll around, I know there's a parent somewhere in America with a kid that needs some football cleats." Reselling on eBay is a time-intensive side hustle. Ogunsunlade estimates he spends 30 hours a week researching, sourcing, listing, and shipping items. "Sometimes it's a grind, but the overall process is something that I enjoy," he said. "It's never seemed like work to me, and I never get burned out from listing items." The extra income provides "a double salary," he said. It allowed him to take a year off from law when his son was born and, generally, provides financial peace of mind. "It just changes your mental makeup — knowing that you don't have to rely specifically on a 9-to-5 job that could end tomorrow."
