Ultimately, even entrepreneurs who keep their day jobs often take the leap

Liza Adams talked to Anita Okemini (right) in Boston about her business, DecktOut, a website for buying high-end, second-hand handbags. Liza Adams talked to Anita Okemini (right) in Boston about her business, DecktOut, a website for buying high-end, second-hand handbags. (Kayana Szymczak for The Boston Globe)
By Scott Kirsner
Globe Correspondent / June 12, 2011

E-mail this article

Invalid E-mail address
Invalid E-mail address

Sending your article

Your article has been sent.

Text size +

Is it possible to be an entrepreneur without sacrificing a steady paycheck?

A small subset of office workers — from State House staffers to Web designers to equity traders — believe they can temper the risk of launching a start-up by holding tight to their 9-to-5 jobs. With businesses that sell second-hand luxury handbags or iPhone apps, some are just looking to earn a little income on the side, while others hope they’ll be able to keep revenues climbing and eventually make the transition to full-time entrepreneur.

Supporting a “side hustle’’ can consume nights and weekends, and keeping your entrepreneurial life from your boss can sometimes entail a little secret agent-style duplicity. But anyone who has ever worked for a company in a position of low-to-moderate authority has at times felt powerless to change things. And one of the best features of a side project is that it’s entirely under your control.

“What’s awesome about it is that it’s up to you to figure out how all of the processes should work, and you get to make all of the decisions by yourself or with a cofounder,’’ says Mike Isman. “You just don’t have that kind of freedom and autonomy as an employee at a big company.’’ Isman started a longevity website called while working at Plymouth Rock Assurance, collaborating with Boston University professor Thomas Perls, who oversees the New England Centenarian Study.

It can also be a way to acquire business or technology skills that you wouldn’t necessarily learn in your day job. “At work, you may not be dealing with the latest and greatest technologies,’’ says Jay Meattle. “But with a side project, you can look at a new database or a new programming language and just decide to give it a try, to see how it works.’’

Meattle initially created Shareaholic, software that makes it easy to share interesting online content, while working at a full-time job; it’s now a standalone company in Cambridge with two employees.

And, says Robby Grossman, it’s a way to “combat the day-to-day monotony’’ of a job that may not feel like your destiny. While working in the Cambridge office of giant business software company SAP, Grossman began building Paperphobic, an iPhone app that helps users keep a digital record of receipts and other information for expense reports. He later joined a start-up company, but still runs Paperphobic on the side.

“I think I was less open about the business when I was at SAP, but now my manager and the CEO of my company know about the project, and they’ve both tweeted about it to help me get users,’’ Grossman says.

These entrepreneurial jugglers say cultivating a start-up on the side can also be a way to test an idea, or give it time to grow, without the pressure of needing business revenue for living expenses. With Paperphobic, says Grossman, “I wasn’t at a place financially to just dive in and work on it for a year, and I didn’t want to raise money from investors because I wasn’t sure how profitability would play out.’’

Peter Brennan, cofounder of the news site Offshore Wind Wire, which reports on the wind energy sector, says the industry hasn’t yet gained enough momentum in the United States to support a business with full-time employees. The site generates a few hundred dollars a month in online advertising, says Brennan, who serves as chief of staff to state Senator Robert Hedlund.

“It’s a small enough commitment that it takes probably an hour or an hour-and-a-half a day, and I do it before and after work,’’ says Brennan, who started the site with a friend after finishing Suffolk Law School in 2009.

But not every boss is supportive of extracurricular endeavors, especially if there’s the perception that you’re putting more effort into your side hustle than your 9-5. Liza Adams confesses that she kept her side project secret from her supervisor at a Concord Internet design firm because “I thought if I told him about it, he’d start looking for my replacement.’’

And then there’s the time required. Adams, who started DecktOut, a website for buying and selling high-end, secondhand handbags, recalls countless late-night photo sessions taking pictures of merchandise. “I was sleeping three hours a night, and I had no social life,’’ she says.

Working on side projects using company computers or other equipment can also create questions about ownership. “In general,’’ explains Michael Barron, a lawyer at the Boston office of DLA Piper LLP, “if an employee uses the resources of his employer in the development of a new product, the employer can assert ownership rights to the intellectual property.’’

Entrepreneurs hoping to attract outside investors to a side project may find them reluctant. “If you don’t believe in the business enough to take the leap, then why are you asking us to jump into the deep end?’’ asks Jean Hammond, a local angel investor.

Of the multitasking entrepreneurs with whom I spoke, two had already quit day jobs to fully dedicate themselves to what had been their side projects. Jay Meattle shifted to Shareaholic full time in early 2009, and has since raised several hundred thousand dollars from investors.

Adams quit in March. “I didn’t know how much longer I could do both, and a mentor I’d found said to me, ‘If you’re really passionate about this, there’s a point where you have to decide to take the leap,’ ’’ says Adams. So she did, even though “the thought of not getting a direct deposit every other Friday was scary.’’

Scott Kirsner can be reached at Follow him on Twitter @ScottKirsner.