From Side Gig to $6M Business: 3 Stories of Employees-Turned-Entrepreneurs
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The Flea Market Flipper

Robert Stephenson, 36, Miami, Fla.

The youngest of seven kids, Robert Stephenson grew up in a family with little money to spare. They often shopped at yard sales, thrift stores and flea markets, where, in addition to buying household necessities, his parents picked up cool items to resell for extra cash.

At 16, Stephenson followed in their footsteps, selling his flea market and Salvation Army finds in the newspaper classifieds. Over the years, he’s flipped a prosthetic leg—purchased for $30 and sold for $1,000 the next day on eBay—and a commercial lobster tank, snagged for $100 at a thrift store and later sold for $1,500.

Despite generating up to a couple thousand extra every month, Stephenson never considered flipping full-time until March 2016. That’s when the company he worked for as a home insurance inspector, making about $30,000 per year, stopped offering health insurance—and he realized nothing was holding him back from going out on his own.

But the pressure was on: Stephenson had a new baby, and his wife recently cut her hours as a personal trainer. “We had to make it work,” he says.

It did. In 2016, Stephenson increased his profits from $42,000 to $133,000—thanks to devoting more time to sourcing larger items with even bigger profit margins, like a security tower he bought for $6,000 and flipped for $25,000.

This summer, he plans to take his gig on the road, visiting flea markets across the country in an RV with his family. He’s also focusing on his new online course Flipper University, which helps others break into the business.

His advice for others: “Don’t overthink it,” Stephenson says. “Because I had to [be successful], there wasn’t any room for self-doubt.”

1_Tanner1The Cruise and Travel Blogger

Tanner Callais, 32, Austin, Texas

After grad school in 2015, Tanner Callais landed a tech product marketing role in Austin. But he soon realized the slow pace of working for a large company didn’t suit him, and began devoting more time to an old side gig.

After receiving a cruise voucher as a wedding present in 2012, Callais got the idea to create a network of sites for cruise goers, covering specific ports. Through affiliate marketing and ads, he generated enough to carry him through grad school. Following graduation, he still passively raked in about $1,000 a month. But he knew there was potential for more.

So in May 2016, he aggregated his cruise sites under and took the plunge into self-employment. He focused on creating more quality content, covering new topics like cruise deals, and expanding his brand by contributing to and getting quoted in other publications.

It paid off: In December, he earned $4,000, and in January he surpassed his old tech salary, bringing in $9,000. What’s more, he’s saving $800 per month in child-care costs by sharing babywatching duties with his wife.

It’s been fun, exhilarating and scary,” says Callais. “But I’m happy that I’ve been able help support my family through my work, and extremely thankful that I’m able to spend time watching my son grow up.”

His advice for others: “Get creative and work harder than you ever could imagine,” Callais says.


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