Phil Tadros, serial coffee entrepreneur

Phil Tadros’s dream was always to open a restaurant or a bar. Instead, he opened a coffee shop. It was 2000, and he was 19—not old enough to sip a drink, let alone sling one. “I was looking for an excuse to drop out of school,” he recalls, when he saw an ad in The Reader: coffee shop for sale to the right person. “I called the guy, Don Selle, and he was like, ‘You don’t want this place, you’ll never make any money.’” Undeterred, Tadros finagled a $20,000 bank loan, and Don’s Coffee Club in Rogers Park was his. He sold it ten months later for $34,000.

Eleven years later, the 31-year-old serial entrepreneur presides over six cafés, including Dollop, Noble Tree and Kickstand Espresso Bar on the North Side. He also has three just-opened spots at Columbia College—a windfall contract from the same school where he’d called it quits a decade earlier. The new acquisitions make his the largest network of independent coffee shops in the city.

While the cafés draw neighborhood regulars with Metropolis beans and snacks by Southport Grocery and Hoosier Mama Pie Company, Tadros has greater schemes for the spaces. “I look at opening a coffee shop as providing an office for the public, a place where people can be productive,” he says. He’s especially catering to the growing ranks of the freelance nation: young developers, entrepreneurs and design talents looking for a comfortable place to plug in a laptop and (in the case of Noble Tree) hit up weekly Jellys—casual coworking sessions geared toward professionals “with flexible working arrangements.”

The cafés’ “public office space” vibe paid off for Tadros in a big way in 2008, when he launched his own Web-design-focused interactive agency, Doejo. “There was this guy [at Noble Tree], and I was looking over at his computer. He was rocking out these incredible graphics.” That designer, Darren Marshall, is now Tadros’s partner at Doejo, which has grown to 37 employees and boasts clients such as Adult Swim’s Homeless Cop show, Burton snowboard gear and Groupon.

Always looking for a new project, Tadros has taken the mingling of online business and coffee even further. He recently bought up 30 percent of WEBbeams, a wireless Internet service common in cafés and other public spaces. “We’re changing the design and adding an interactive component that will let users set up profiles,” he says. “So if you’re in a café working, other people can see who you are and what you do, and communicate with you—if you want.” The new features will be rolled out in a few months.

Another caffeinated business venture in the works is a transformation of Doejo’s current space at 2934 North Broadway once the office moves to its new, larger location near Clark and Adams streets. What’s currently the employee coffee bar will become a public café, while about 40 desks in back will be rented out to people looking for office space. “We’re going to be selective about who we let in,” Tadros says. “I want to curate that group so that they benefit from each other: writers, graphics people, developers.”

Tadros also launched a Web-based event-planning directory called Galaist last September and an online expense tracking application, TextHog, in 2009. He even made a run for Rahm’s congressional seat last year.

If this perpetual multitasker seems to have clicked open more windows than he can manage, his employees don’t seem to think so. “He’s totally an idea guy, with maybe 30 crazy ideas per day,” says Katie Bezrouch, who manages Tadros’s cafés. “You think it’s all bullshit until you look and—hey, suddenly he’s opening a doughnut shop across the street.”