How the Founders of Philly Tech Week Built a New-Media Empire

What did it take for two young Temple grads to create one of Philly’s few media start-up success stories? A little recession-based desperation and a thorough rejection of the old rules.

This month’s Philly Tech Week is one way Wink, left, and Kirk, right, generate revenue. Photograph by Gene Smirnov

This month’s Philly Tech Week is one way Wink, left, and Kirk, right, generate revenue. Photograph by Gene Smirnov

It’s a frigid February day, and Union Transfer — as usual — is throbbing with young people. Only it’s not rock bands and sweaty, dancing concertgoers filling out the venue this afternoon, but bright-eyed, tech-oriented millennials and the companies that want to hire them. The event? A good old-fashioned job fair.

Playing ringmaster this day is Chris Wink, editorial director of Technically Philly, the website that covers the local start-up community. “Job fairs are boring,” he says. “Ours is not.” This is one of dozens of events Technically will put on during the year, and those events do most of the paying for the site’s journalism. Among the throngs of job-seekers wearing blazers and pressed slacks, Wink is easy to spot thanks to a Zuckerbergian hoodie and a pair of checkered Vans shoes. “It’s probably start-up chic,” Wink says of the outfit.

A closer look, though, reveals something a bit more formal than the insouciant uniform of tech. Wink, 29, is also wearing jeans, but they’re jeans that actually fit — “I was definitely a thrift-store kid, so I’ve stepped up a bit” — and underneath the hoodie is a crisp-collared oxford shirt. The adolescent rebel, it seems, is just barely covering the executive underneath.

Of course, that’s not the only contradiction embodied by Wink and his Technically Philly partner, Brian James Kirk, the site’s business director. Over the course of the past half decade, they’ve been both rule-breakers and defenders of the realm, showmen and sober-eyed journalists, millennial whippersnappers and “old heads.” Keeping track of it all can be dizzying.

What can’t be denied, though, is this: Those contradictions have made Technically Philly one of the few media start-ups of the past decade to actually survive the rough-and-tumble of Philly’s ecosphere. And the embodiment of Wink and Kirk’s approach has become one of the city’s most celebrated new traditions: Philly Tech Week. The fifth edition takes place this month — Wink and Kirk expect to host more than 125 events, upwards of 25,000 attendees, and one of the biggest, most important parties of the year.

“It is amazing to watch what the two of them have done,” says Andrew Mendelson, the former journalism chair at Temple University and now associate dean of the graduate school of journalism at the City University of New York. “I think, all things considered, they’ve done an amazing job in an uncertain journalism ecosystem.”

THE TECHNICALLY PHILLY story begins, as many millennial tales do, as one of recession and doom. Kirk and Wink and their friend Sean Blanda were buddies at the Temple News, graduating in 2008 just as the economy sank into recession — and media companies, facing a loss of advertising that never quite returned to pre-recession levels, found themselves sinking even faster. Unable to procure full-time jobs in the industry, the trio decided to create jobs for themselves.

“We thought, ‘If no one’s going to give us a job, let’s make one. What do we have to lose?’” says Blanda, who has since moved on to an editing gig in New York. “The Inquirer wasn’t going to come knocking on our doors.”

“We were not entrepreneurs,” Wink adds. “We were just scared out of our minds and desperate.”

The early site — a mix of links to pieces collected from around the Web, short interviews, and commentary about Philly’s tech scene — quickly drew attention, but the going was rough: Blanda would write posts on the bus to and from his day job, then again after dinner. The site grew as the founding trio tried to keep their respective heads above water. Wink made just $16,000 in the first year, including outside work. “I deferred my student loans,” he says. “I did not pay all of my taxes. It was an ugly, brutal year.”

But the trio made two choices early on that would prove fateful. First, they decided that Technically Philly wouldn’t just report on news in Philly’s tech community — the site would also be a cheerleader for that community. “I’m a believer that a reporter is always a part of the community that he reports on,” Wink says, and adds: “I’m supposed to be serving my community of readers.”

Second, they decided they needed a different approach to pay the bills. “What was unique about us in the early days was, we said that advertising wasn’t going to be a strong focus for us,” says Kirk, now 31. They started producing events instead — Philly Tech Week would soon emerge as the pinnacle of the approach, which would come to include job fairs, networking events, and conferences on civic innovation. The recent job fair, for example, had roughly 500 attendees paying $10 a head, Wink says — a tidy sum for an afternoon of work.

Taken together, the choices seemed to represent a bit of a minefield. “Cheering in the press box” is an ethical no-no for most journalists, and event production made it likely Technically’s founders would end up taking money from the same people they were reporting on — often a tricky situation.

“Events like that are so weird to an older generation of journalists. They never had to do that,” says Mendelson. Then again, he notes, those older journos “had a reliable form of income … and they didn’t have to do anything more to create community except put their product out.” Today’s journalists sometimes have to hustle a little harder, get their hands a little dirtier.

It’s in discussing such issues that Wink can veer from being the man in the hoodie to the oxford-shirted exec and back again. He can talk about “the ethical standards that sometimes hold us back,” but a few minutes later present himself as a fierce defender of those standards. “Whenever any industry goes through change, that’s an opportunity for that industry to reassess,” he says. “From the very beginning, everyone on our team has tried to pretty regularly say, ‘Is this an ethical rule that’s in place for a good reason? Or is it out of habit?’”

Then, a breath later: “There’s a lot of traditions we take really damn seriously. We talk about disclosures a lot.”

Another balancing act: Wink has his P.T. Barnum side — he’s a showman, knows it, is good at it, and wants the journalists working for him to learn to do the same — and his sober, Edward R. Murrow side. It’s not that either persona ever wins out, he suggests: It’s that both really are in the service of doing good journalism about Philly’s tech community.

“We’ve made people who have given us money angry; we’ve lost money from potential sponsors we reported on or when we reported issues that they weren’t interested in seeing reported,” he says. “I feel I have lost enough money to know that we have journalism DNA in what we do.”

WHATEVER QUALMS other journalists may harbor, out in the city’s tech community, it’s hard to find anything but love, both for Technically Philly and for Philly Tech Week. The site and the event are often given credit for helping the city’s legion of developers and tech workers coalesce into an actual community. “This region has historically had a lot going on over the years, but we’re not known as a tech hot spot the way some areas are,” says Paul Diefenbach, associate professor of digital media at Drexel University. “Part of that’s a PR problem, but in some ways we’re less flashy as well.”

The rise of Technically Philly changed things, helping techies find each other, learn about each other’s projects, collaborate and challenge each other. One prominent project: OpenDataPhilly, which provides data from City Hall to hackers and developers, who repurpose it as apps, databases and more. Observers say City Hall opened its long-hidden, long-dormant data to the public only after Technically Philly partnered with tech experts to advocate for the project. Diefenbach says the site has even helped tech-oriented college students start to see the city as a place to stay and try to make careers. It’s “a really good showcase,” he says, “of the stuff I know has been going on for the 25 years I’ve been here.”

Wink accepts the praise. “There was a community here before we existed — but selfishly, I absolutely believe we were a part in connecting the pieces,” he says. “I just think we’ve focused it.”

If Technically Philly helped crystallize the tech community, Philly Tech Week gave that community a place to gather, and a party to celebrate itself. It grew quickly, from a few dozen events in 2011 to more than 125 — including a mayoral forum where candidates will be pressed on tech concerns, an “entrepreneur boot camp” and development seminars — expected to fill out this year’s calendar. At its most basic, the week is “an amazing way to bring the community together,” says Tracey Welson-Rossman, chief marketing officer for Chariot Solutions, a software development firm that helps sponsor the week.

It’s also a critical business opportunity for Technically Philly. The first event paid enough that all three founders could work the site full-time. Today, most sponsorships, which generate the bulk of funds brought in by events, sell for between $2,000 and $35,000, depending how much a sponsor — they include notable companies like Comcast, Microsoft and a host of others — wants to spend on the exposure. Those funds, in turn, have helped Technically Philly set up similar sites in Brooklyn, Baltimore, Delaware and Washington, D.C., under the Technically media umbrella. (The sites serve a niche audience, collectively attracting 150,000 unique visitors per month.)

And the impact has spilled beyond the tech community, becoming a crucial element in how Philly has started to define itself as a forward-thinking, millennial-friendly community where discussions about innovation are probably just a coffee-shop table away. It doesn’t hurt that Tech Week ends — this year, like last — with a kick-ass party at Comcast headquarters.

“The rise of the millennial population has been reported on extensively,” says Mark Headd, who served as Philly city government’s first “chief data officer” before moving on last year. “But it’s interesting to see a pub like Technically Philly mature at the same time. You wonder if the rise of the millennials has powered Technically Philly, or if people read Technically Philly and say, ‘I’d like to go there.’ Perhaps a bit of both.”

Influence remains one of the enterprise’s chief compensations for its founders. Their business hasn’t made Wink and Kirk rich — Technically’s profit margins are under five percent, they say — but it’s been sustainable.

And after a half decade, the still-young men have become something like gray eminences in both the tech and media communities: Wink is heavily involved in journalism hangout the Pen & Pencil Club, where he serves as a board member, and the local chapter of the Online News Association. Technically Philly isn’t quite the last man standing, but it’s been around long enough now to prove naysayers wrong and watch other media start-ups falter and fail. These days, its founders know, a profit margin of any size — even below five percent — counts as a success.

“Whenever anyone starts anything new, the presumption is that it won’t last, so immediately people will describe why it won’t last,” Wink says, looking back to the early days. “Hey: We started. And we exist.”

Originally published as “Technically Speaking” in the April 2015 issue of Philadelphia magazine.