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About eight years ago Matt Mickiewicz encountered a problem while scaling his latest company 99Designs. Today, it is the largest online marketplace for graphic design, but back then the CEO and wunderkind was having trouble finding the talent to facilitate such a large expansion. He consulted a number of online resources that weren’t terribly helpful, and raised the frustration with a number of fellow tech execs who told them they had encountered similar roadblocks. So, like any serial entrepreneur, he decided to solve the problem himself.

“That has always been my approach,” says the now 35-year-old. The result of his staffing conundrum was Hired, an online recruiting tool that matches tech companies with software engineers—one four Mickiewicz-founded companies with a combined worth of one billion. He stayed on as CEO and chief product officer until last year, when he left his active role in order to pursue angel investing and mentorship full time. It’s the part of the business he has always loved best—getting to make something out of nothing, exploring new worlds, identifying a problem and reframing it as an opportunity.

To date Mickiewicz has advised on 20+ startups including Optimizely, Gusto and PhenomPeople. In some cases his input is as formal as a scheduled weekly phone meeting. In others the relationship is a little looser. But it’s always been about empowering entrepreneurs to make their own informed decisions.

“I provide advice, not prescriptions,” he says, adding that he looks for start-ups that are fundamentally disruptive, both because consumers aren’t inclined to make changes for small gains, and because he wants his efforts to effect change.

Chasing opportunity has been a theme in Mickiewicz’ life since even before he was the one making decisions. When he was four his parents escaped communist Poland, carrying their two sons and two small backpacks. They spent a couple of years in Germany and eventually settled in Vancouver when Canada was the first country to offer them VISAs. Mickiewicz entered grade three speaking barely a word of English, but by the end of the school year he was reading and writing and at the top of his class. When most boys were passing around copies of MAD or Sports Illustrated, Mickiewicz got his first subscription to Fortune magazine. “I loved to read about Bill Gates and all of these entrepreneurs who were making a difference in the world,” he says.

“There’s a thrill that comes with seeing the way things are done in different parts of the world.”

Matt Mickiewicz

About halfway through high school he launched his first business, a web development resource called SitePoint. Once again, it was a case of coming up against a problem and recognizing it as a market void that he could fill in ia unique way: “I was trying to teach myself about building websites and online marketing, and there was a lot that wasn’t out there. I decided to just share my own learning journey, and that became SitePoint.” The website was a hit—written up in L.A. Times in its first couple of weeks, and featured in USA Today shortly after that. Nobody knew that the new tech hotshot was actually a high school student, who took phone meetings at the nearby Starbucks and cleared half a million dollars in ad sales before third period.

Mickiewicz’ parents and brother were supportive of their rising star, who opted out of a family trip to Disneyland because he had a busy workweek. He also opted out of another common path most young people take: higher learning.

“The opportunity costs of taking four years off were too high,” he says. He also feels that our education system trains people to be cogs in other people’s machines. Mickiewicz is no cog.

He is, however, a devoted student. He clears about a book a week and tries to keep his curriculum varied. On his bookshelf currently there is a Rockefeller biography, three books about Russian history, the latest astrophysics best seller by Neil Degrasse Tyson and a sci-fi title that contemplates the future of AI. When asked if he ever reads anything a little more lowbrow, he says he devoured Bad Blood on a recent trip to Tulum (tell-alls about disgraced tech giants are his version of a beach read).

Travelling is a more recent passion and a frequent source of inspiration: “There’s a thrill that comes with seeing the way things are done in different parts of the world,” he says, calling it “a good reminder that the way things are isn’t necessarily the way they have to be.”

Back home, he has recently taken up flying lessons because he wanted a challenging hobby. “I like the idea of flying because you’re using so many different skill sets at once—physics, mechanics, communication,” he says. Next month he will take his written exam and then he will take to the skies. It’s a whole new world up there full of new challenges and opportunities. And if he hits turbulence, chances are he’ll see it as his next opportunity follow a new path.


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