Melissa and Rob Stephenson are experts at “flipping.” That’s slang for buying products cheaply and reselling them at a profit.  Three months after finding a discarded chair that they managed to sell for $50, they’ve turned that modest profit into $100,000 of merchandise. Their plan is to keep reinvesting the proceeds from each sale until they have enough to buy a house — hopefully by the end of the year.

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Flipping can be a profitable business, the couple says. They’ve been doing it full-time for the past three years, earning between $120,000 and $130,000 annually, while working about 30 hours a week.

“A lot of people think that what we do is gambling, but it’s not at all,” Rob says. “Anyone can do this.”

It’s all about consistency, research and shipping, he says. The key: never buy something unless you know what it’s worth. And realize you can get a lot of things for free.

“A lot of people assume that if someone is giving something away, it’s worthless,” Rob says. “That’s not true. Besides, worst case, you’ll end up throwing it away later. What do you have to lose?”

Flipping doesn’t have to be be a full time job, Rob adds. He and Melissa engaged in it as a side hustle for years, using the profits to finance vacations and little luxuries. But when they had their third child a few years ago, Rob decided he wanted to spend more time at home. They decided to take their profitable hobby more seriously. They now also teach others how to make money reselling through classes and their website FleaMarketFlipper.

Stephenson’s tips for turning flipping into a profitable side hustle:

Establish a routine

Rob spends 15 to 20 minutes every morning and every night, looking through CraigsList, LetGo and OfferUp for items that people are selling and giving away for free. He and Melissa also take walks on trash day, looking for throwaways that could be sold. (This is how they found the $50 chair that started this year’s flipping challenge.) They go to flea markets every week.

“Maybe you won’t find anything for a week or two. But if you keep going, you eventually will,” he says. “You’ve got to consistently do the things that are going to cause you to make progress toward your goals.”


When you find something that intrigues you, but aren’t certain of its value, turn to Google.

“If I see something that I have sold in the past, I know I can negotiate the price to what I need to resell it profitably,” Rob says. “Otherwise, I will snap a picture of the item. And I will try to find it on my phone. Once I have an educated idea of what I can sell it for, I will go back and negotiate a deal.”

Why would vendors sell to you cheaply enough that you could resell at a profit? Many flea market vendors are buying in bulk and have too many items to sweat the best price for any one thing, Rob says. That gives you the opportunity to cherry pick.

Choose your platform

While Stephenson scans other sites to pick up products, he sells almost exclusively on eBay. The reason: eBay gets far more eyeballs.

“It reaches so many more people. Facebook, Offer Up, Craigslist…you are reaching 40 to 60k people. eBay has 171 million registered users who have the potential to see what you are listing,” he says. “A lot of people get hung up by eBay’s [seller] fees, but we just factor them into our prices.”

Provide shipping but not returns

EBay favors sellers who will provide free shipping and returns, Rob says. But, allowing for returns opens you up for buyer fraud and for spending a bunch of money on return shipping — a net loss. Knowing that an item you’ve shipped is really sold is particularly important for Stephenson because he specializes in heavy, big-ticket items, such as construction tools, which cost a fair amount to transport.

To head-off buyer dissatisfaction about his no-return policy, he says he takes great pains to describe his products. He will take particular note of the fact that the products are used and spell out and photograph any flaws.

“I took the term ‘mint-condition’ out of my vocabulary,” he said. “It’s very important not to over-promise and under-deliver.”

Go big

You can specialize in selling anything — handbags, tools, crafts, clothing — but Rob likes specializing in big products, like exercise, construction and manufacturing equipment. Why? You can earn more on each sale.

If you’re selling products worth $10 to $50, your profit on each is going to be just a few bucks, he explains. To make a living with that model, you have to have a lot of sales. That means you have to work more hours.

Buying more expensive products means you have a little more risk since you’ve invested more in each, but you’re likely to make considerably more with less work.

“Our comfort zone of investment is $20 to $50,” he says. “I want to make $300 to $500 on those items.”

Ship smart

Shipping costs could be crippling if you tried to ship big items through the mail or UPS. However, there are a number of online marketplaces for shipping, such as UShip and Citizen Shipper, where you can get a much better deal.

These marketplaces allow individuals to communicate directly with big shipping companies, as well as side hustlers with trucks, to negotiate the best deal. Even big commercial shippers provide cut-rate deals on these sites because they’re filling their trucks for “on-the-way” deliveries when the truck isn’t full. Because that room would otherwise go wasted, the shipper is willing to take less for your one-off item, as long as the pickup and drop-offs are convenient.

One response to “Flipping a $50 chair into a $100,000 business”

  1. Elana McInerny Avatar
    Elana McInerny

    Rob’s point of view regarding eBay is spot on. I have sold items for the past 12 years at least through all the online sites he mentions. What was once enjoyable has become annoying because of bad, lazy, hostile, fake buyer behavior. eBay is the way to go provided you follow his advice regarding shipping and stay true to your intentions, e.g. not letting others push you into shipping if you are not offering that. It takes time but at Rob’s strategy makes perfect sense. Our massive American consumption habits makes product for resale easy to come by! Where I swore I wouldn’t resell things I get for free I’m willing to try again thanks to this article! thanks Kathy!

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