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


Turning a long-time hobby or side gig into a successful venture is no easy feat. It takes guts, laser-focus and a commitment to doing whatever it takes to advance the business. But once you’re on the other side? The potential benefits are seriously rewarding.

Read how these three business owners transitioned from employee to entrepreneur—ultimately earning more and improving their quality of life at the same time.

The Evolving Entrepreneur

Tyler Lundmark, 29, San Francisco, Calif.

Tyler Lundmark came up with the idea for his business RoomDividersNow as an undergrad. “A bunch of my college friends living in New York and L.A. were splitting bedrooms, and putting two mattresses in the middle of the room,” he explains. “I knew that a room divider solution could really pop.”

After graduating in 2010, Lundmark landed a digital marketing role, but didn’t stop developing his idea. When he finally launched in 2012, the company didn’t get much traction. So he spent the next couple months refining the process, using what he’d learned about online marketing from his day job.

Finally, sales started rolling in, and by the end of 2012, he’d earned $60,000. Just a year later, the business surpassed six figures. By 2014, Lundmark was spending so much time on the business that he knew it was time to his leave $70,000 job and turn his side gig into a full-time enterprise.

Last year, the business made $6 million. He credits its success to constantly testing new products and incorporating customer feedback. What started as a room divider curtain is now a kit, and he’s working on expanding internationally. To date, his business employs 11, including his parents and brother Jackson, who joined as a partner last year.

His advice for others: “Stay focused,” he says. “Hone in on ‘multipliers’ and projects that will help you scale the business quickly.”

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.”

The 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 Cruzely.com 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.