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“As long as you have your phone and a way to look up what an item previously sold for, you're already ahead of the game.”
Matt Myers, a PE teacher, knew the coming months were going to be financially tight. His yearly teaching contract was ending, and he needed money to bridge the indefinite gap between school years. Back when he was a child, his dad had made extra money buying and reselling items from estate and garage sales — so Matt figured it might work for him too.
He took $500 from savings, hit a couple of thrift stores, and planned to sell whatever he found on eBay. To guide his buying, he focused only on items he'd once owned or felt a strong connection to — if he'd wanted it, others probably would too. He came home with about 75 items, and while he'd grabbed a few electronics, he felt especially drawn to sports memorabilia: jerseys, jackets, caps, and cards.
His first sale, surprisingly, wasn't sports at all — a $2 iPod Touch he'd bought at a garage sale sold within hours for $140, a nearly 7,000% margin. He treated his girlfriend (now wife) to a nice dinner and got right back to work. Still, he stuck with sports memorabilia, where he knew the most and could trust his instincts.
For two years it stayed mostly a hobby that bridged his contract gaps — the occasional garage sale, nothing major — until one find showed him the real potential. At a local garage sale he spotted a rare 1952 Boston Braves pennant priced at 50 cents. He bought it, listed it, and sold it days later for $450.
That win convinced him to get serious. He opened an eBay store named Kevin's Clubhouse in honor of his dad, and began treating it like a real ecommerce business — consistently hitting garage sales on weekends and school breaks, finding new items to flip each week. The more he invested, the better his finds and sales. He's since made $62,000 flipping, now averages around $8,000 a month in profit, and reinvests much of it. Instagram, with team hashtags and DMs, drives a lot of his sales.
His advice for starting with your own $500: pick a topic you're interested in and knowledgeable about, and find items you feel a connection to. Don't worry about getting it right every time — sometimes things won't sell, and that's the nature of the business. But if you're right even half the time, you can be profitable.
