How long does it take to turn a side hustle into a small business?

June 19, 2019

The 2019 Hiscox Side Hustle to Small Business™ Study found that, on average, entrepreneurs work their side hustle for 19 months before they are ready to make the leap and turn it into their full-time job. During that time, the average entrepreneur worked 20 hours a week in addition to their full-time job. In most cases, they worked on the weekends and at night, juggling their responsibilities for work, family and their side hustle business. 

Jared Novack founded Upstatement as a side hustle with some friends he met while working on the student newspaper at Syracuse University. He said it took them about a year and a half from the project that launched their side hustle, until they were able to turn it into a small business. 

A side hustle is born

After college, Jared and his friends Mike and Tito went their separate ways, to the newsrooms of The New York Times and The Boston Globe. Eventually, the three met up again in Boston. 

One night, Jared and Mike were at a party together and Mike mentioned that he was working as a freelance web designer. Someone said their company was looking for a web designer. According to Jared, “Mike said, ‘Oh, awesome. Where do you work?’ and he says, ‘Harvard University Undergraduate School of Design. Are  you interested? And the answer was definitely, ‘yes.’”

Jared and Mike put together a pitch (“making the case way harder than it needed to be made,” said Jared) for the project and it was accepted. 

“That was one of the first big projects we had,” said Jared. “That led to other opportunities. Meanwhile, Mike is doing this full time. Tito and I are doing this part time – nights and weekends while we’re also working at The (Boston) Globe.”

Networking and word of mouth

Finding a core client can be the impetus to consider making the move from side hustle to small business. Once you find that first major customer, you may find that others follow.

“We found that the work started to find us,” said Jared. “We did a good job, I think, sort of accidentally networking. We just knew a lot of people, and word that we were doing this got back to us in the form of other project opportunities. We said, ‘Actually, this could just be our job.’ But this was when the recession hit. This was early 2009 and I think the hopes we had about that turning into 50 other projects didn’t materialize.”

Despite the shaky economic climate, Jared decided that the time was right to make the move, and turn his side hustle into a full-time job. 

“I was 25,” Jared said. “I had no kids, no mortgage, no house – nothing I have today. The question came to me as, basically, where I am going to do my best work? I knew that the worst thing that would actually happen to me at that point was I would go back and get a job. I could do this.”

The three created a partnership and left their ‘day jobs’ to do design full time. Today, Upstatement employs 35 people and does design work for some of the world’s most recognizable brands. 

Hiscox's side hustle to small business podcast

Hear Jared’s story on the Hiscox Side Hustle to Small Business podcast, and learn more about how to turn a side hustle into a small business. Download the study, subscribe to the podcast, and get behind-the-scenes looks at entrepreneurs who’ve done it.