Billionaire or bust

Chicago entrepreneurs living by the skin of their teeth—until they cash in big

  • Jenna Compton works out of her apartment.
Jenna Compton works out of her apartment. (Lenny Gilmore/RedEye )
February 21, 2012|By Mick Swasko, RedEye

Jenna Compton has no TV. Her fridge contains Oscar Meyer turkey cold cuts, which she eats without bread or condiments. And her expensive gym membership has been abandoned in favor of a community workout center.

It's safe to say the 26-year-old Andersonville resident is light-years from being a millionaire. But she has one thing in her pocket—an idea—that she's really hoping to cash in on.

Compton, a freelance graphic designer with plans for a social media website, joins a burgeoning crowd of digital pioneers with their eyes set on becoming the next startup success in Chicago. The number of such ventures grew from about 80 in 2010 to about 120 in 2011, according to the Illinois Innovation Council. In January, Merchandise Mart tenants announced plans for an expansive center, dubbed 1871, to house office space for entrepreneurs with projects in their early stages. In the shadow of other multimillion-dollar startups born in Chicago—heard of Groupon or GrubHub?—Compton and other entrepreneurs say they are willing to live on the cheap and persevere in their quest to become the next big thing.

"It's something that I don't know how to explain. I have always had a tendency to go for my own thing," she said. "Whenever I am in a different atmosphere and I am someone else's employee, I tend to feel like creativity is stifled or you're playing by someone else's rules."

Compton, who works part-time and freelance jobs to make ends meet, has spent the past three months in her room behind a hand-sanded wooden desk with a Lil Wayne poster above it. She and two business partners are in the early stages of developing GoSosh, a site they say will allow businesses to reward customers through social media. Though she faces many obstacles, Compton said, the potential for success drives her.

"It's scary," she said. "But I feel it's more of a challenge of yourself to succeed as an entrepreneur."

Her partner, Waylon Janowiak, said working toward a profitable business is worth the sacrifices of sleep and social activity.

"The big thing is knowing [your idea] is going to help someone in some way or another," the 20-year-old Bridgeport resident said. Between school and a part-time information technology job, he handles technical aspects of GoSosh, where a 1 or 2 a.m. bedtime is common before waking up the next day at 7 a.m. for work. His office is his bedroom, where multiple monitors take up space on a glass desk next to the whiteboard where he jots down ideas.

The team is rounded out by Joshua Hensley, 19, of Bronzeville, who shares his ideas with the rest of the team on napkins and notebook paper. He said the group is able to operate without much funding because each member contributes skills to the project.

"Success is not achieved by earning a mountain of cash or securing some great corporate title," he said. "Success is finding your passion and using it to effect positive change in the world."

A bit further in the process is Richard Komaiko, 26, who said he remembers the cash-strapped days of his startup,

attorneyfee.com. He ate ramen and watched as his law school friends made tens of thousands of dollars working summer internships as he focused on his idea. He rarely went out, he said, and when he did see family and friends, all he could talk about was his site, which aggregates information about legal costs.

But, he said, the days of relying mostly on student loans is over. After the first version of the site turned a profit, Komaiko said the startup has relaunched with a new vision, and he has his sights set on a multimillion-dollar business he says will turn the legal world on its head. Still, he recalls the early days, living in one-bedroom apartments that also served as his office space.

"The reality of it was pretty bleak," he said, recalling working on the site two years into law school.

He said the decision to pursue a career outside law once he graduated was made for him. The premise of attorneyfee.com—publishing data on average prices law firms charge for basic services—wouldn't be looked kindly upon by future employers. In fact, the site was threatened with three lawsuits even before it formally launched two years ago, and media attention to his mission burned bridges.

He estimated struggling for about two years before things got better and said any small startup should anticipate a few years of living more than modestly. Now the 10-employee startup is housed in a brick-and-timber loft office in River North, and the company had enough money last year to take a trip to Puerto Vallarta, Mexico.

"That's not wasted time, it's time when you're learning," he said.

For Compton, who's only three months in to developing GoSosh and faces at least six months of estimated beta testing ahead, things do get tough.

"Once every month I go through a phase, I'll have one 'oh [bleep]' day and then I will be good," she said. "I think if I do ever make it to huge success, I know I am going to appreciate this time of growth. I just feel like I am fulfilling my talents, not just sitting at a desk job 9 to 5."

mswasko@tribune.com | @mickswasko

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