Courtesy of Yinka Ogunsunlade
Yinka Ogunsunlade has had a profitable reselling business from the very beginning.
The first item he listed and sold was a perfume set that his mom received for Christmas and wasn’t planning on using.
“I saw what it sold for in the retail store, and I said, ‘Let me see if I can put it up on eBay,'” the DC-based lawyer told Business Insider. “It was a no-cost item, so anything that I made from it would be strictly profit.”
That was back in 2005. Ogunsunlade had just started law school and was home for the holidays.
He sold the perfume “fairly quickly,” he said, and then moved on to listing items from his closet. “I had way too many clothes.”
After working his way through his closet items, the next step was to start shopping at discount stores for inventory. Gradually, over the last two decades, Ogunsunlade has built a six-figure side hustle reselling shoes and clothing.
Between September 2024 and September 2025, his company, Fashionably Legal, did $120,000 in sales on eBay, according to a screenshot of his seller hub dashboard.
With this particular side hustle, the barrier to entry is extremely low, said Ogunsunlade: “There was no startup cost.” You just have to be willing to invest time, he added: “The more time that you put into researching items and sourcing items, the more items you can list. You see a direct return on the amount of effort that you put in.”
The eBay veteran shared where he shops, what he’s looking for, and strategies he uses to ensure he’ll turn a profit.
Source products from discount stores and sites
When Ogunsunlade first started reselling on eBay, he spent hours sifting through clothing racks for deals. He said he stopped by his two “go-to” stores — Neiman Marcus Last Call and Saks OFF 5th — almost every day.
He still spends a couple of days a week shopping in-store, but he’s shifted to doing more “online arbitrage,” which saves him time and gas money.
“I can just have the items sent directly to me, list them right away, and then get them shipped back out,” said Ogunsunlade, who uses sites like YOOX and NET-A-PORTER to find great deals on luxury items. “I’m constantly on those websites looking for different sales, refreshing pages, seeing items coming in and out of stock.”
Sourcing items is time-consuming and can sometimes feel like a grind, he admitted. But, as someone who enjoys shopping and the “thrill of the hunt,” he said, “it’s never seemed like work to me.”
Price compare using the ‘sold items’ section on eBay
To succeed in any category on sites like eBay, you have to pay attention to two numbers: the price of the item you plan to buy and resell, and what comparable items have sold for on eBay.
Ogunsunlade advises browsing the “sold items” section of your niche on eBay to figure out what is selling well and what isn’t. You can also reference the sold items to ensure you’ll turn a profit, rather than lose money on an item.
Courtesy of Yinka Ogunsunlade
When he first started on eBay, as he was shopping for inventory, he’d 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. Now, thanks to smartphones, he can look up products on the spot and decide if the margins are strong enough to purchase.
It’s essential to use the “sold items” filter on eBay, he said, as there could be a big discrepancy between what something is listed for and what it sells for.
Pay attention to seasonal items and trends, but stick with what you know and love
Having been on eBay for 20 years, Ogunsunlade has started to notice patterns.
At the start of football season, for example, he stocks up on cleats: “Once July and August roll around, I know there’s a parent somewhere in America with a kid that needs some football cleats.”
What he likes about his category, though, is that it’s more resilient than others.
“Everybody’s always going to need a pair of running shoes or walking shoes or less formal, athletic wear,” he said. Whereas, with a category like business attire, there can be more of an ebb and flow. “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 also enjoys selling active wear the most.
“I think it’s definitely beneficial to sell something that you’re passionate about — not to just sell it because you can,” he said. When selecting a category to specialize in, ask yourself: “Do you enjoy looking at this same style, this same type of item every day?”
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