Former Cop Finds Side-Gig Success

After frustrations with long hours, Joe Cain built his own business instead.

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As a captain in the New York Police Department, Joe Cain noticed that many of his fellow officers held side jobs to supplement their income. He also knew that “cops only trust other cops,” and would much prefer to hire a handyman or contractor who also carried a badge. So he launched sidegig.com, a website that connects cops and firefighters with second jobs to people who want to hire them. Today, more than a decade after he started it, thousands of people across the country use the site.

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“Cops and firefighters have always had side gigs,” Cain says, because historically, the jobs did not pay well. He adds that the economic uncertainty of today’s market, even in public sector jobs, further motivates police officers to find side-gigs, often as security guards or contractors. “In New Jersey, they’re laying off cops like crazy. The public sector does not have the security that it used to,” he says.

Partners of police officers and firefighters also use the site to offer their services; current listings highlight attorneys, mortgage brokers, artists, and Realtors. “A lot of wives started saying they have side gigs, and I said, ‘You’re absolutely welcome here,’” says Cain. The site currently has thousands of registered users; posting service or product offerings costs $150 to $200 a year. Cain says he doesn’t make money off the site and all proceeds pay for website-related costs.

To boost his own financial security, Cain started his own side gig when he was working as a captain in the New York Police Department. In the late 1980s, when he worked as a foot cop in the Bronx, he became a certified tax specialist and started helping fellow officers file their taxes. Over the next decade, he built his side business slowly, maintaining about 100 clients.

Then, when his son was born on Sept. 11, 2001, he realized he needed to leave the police force to become the kind of father he wanted to be. “I said, ‘I could be the chief, or I could be Daddy.’ I loved being a cop, but I was working nonstop. The phone rang all the time [at night]. I said, ‘Everybody I care about is asleep under this roof.’”

His side gig, as well as his pension, gave him the freedom to retire in 2004. “This side gig made the decision a no-brainer for me,” says Cain, who lives in a suburb of New York City. He and his wife saved money in advance to get through a couple of lean years as he built his business, which eventually replaced his former salary.

Now, he says, with a client base of more than 1,000, 80 percent of whom are also former or current police officers, his office is just a mile away from his home.

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Since Cain works for himself, he now has the freedom to set his own schedule. While he works 60- to 70-hour weeks around tax season, he scales back during the summer, working three or four days a week. And even during his busiest period, he says, he’s always home at the end of the day, which wasn’t always the case as a captain in the police force.

He attends every baseball game, concert, and school event of his daughter, now 12, and son, now 10. “We’re the helicopter parents,” he jokes. Since he and his wife are both former police officers, he says, “We’re a little paranoid.”

His advice to others who dream of working for themselves? Start planning early, well before you go full-time with your small business. “Figure out what you like to do, and set yourself up,” Cain says. Just as you wouldn’t buy insurance after the house is on fire, you don’t want to wait to launch a business until after you retire or leave your steady paycheck. Says Cain, “The old way is to get a job at Con Ed and you’re set for life. That mentality is pretty much gone. People are more self-reliant. You have to be.”

Twitter: @alphaconsumer