Simon Owens
Jul 31, 2018 · 23 min read
Philly Tech Week. Source: Visitphilly.com

When Christopher Wink graduated college in 2008, he had no intention of launching a media company. He just wanted an entry level journalism job that would allow him to work his way up within the industry.

But back then, when newspapers were hemorrhaging revenue and announcing mass layoffs, there weren’t a lot of journalism jobs to pass around. So, out of desperation, he and a couple other college friends launched a Wordpress blog called Technically Philly. It covered the local tech scene, an industry that at the time was largely ignored by regional news organizations.

Eventually, the blog gained traction and profitability, and the growth allowed Wink and his friends to launch local tech blogs in Brooklyn, Baltimore, DC, and Delaware.

I interviewed Wink about the early days of running an unknown tech blog, what it takes to launch a site in a new city, and why he’s never been all that interested in building out an advertising business.

To listen to the interview, subscribe to The Business of Content on your favorite podcast player, or you can play the YouTube video below. If you scroll down you’ll also find a transcript of the interview.

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A transcript is below.

Simon Owens: Hey Christopher, thanks for joining us.

Christopher Wink: Thanks so much for having me.

So you basically helped create this hub of local tech news sites. And it basically came about because you were unlucky enough to graduate college during the Great Recession. Can you talk about that?

Yes! I can talk about painful, early adult memories. Is that what you’re really asking me? All entrepreneurs are either brave or desperate, and I was more on the desperate side, and then perhaps later on there was some bravery but in the origin story I would admit it was much more about being terrified. So yeah, graduated Temple University in Philadelphia with a couple friends. Right after graduation we did the journalists did. I got a fellowship covering — — I was shared by two newspapers in Harrisburg, Pennsylvania covering the state capital. I was going to government hearings. I was trying to find a great lead inside an electric regulation government hearing, and the plan was to get a great mid-market newspaper job and climb my way back to a big market and be an influential reporter. That was the dream. And this is 2008, and that of course proved really foolish, both the decade plus decline newspapers generally, was sped even further by the recession, the story we all know.

Newspapers were just hemorrhaging jobs at this point. This was a really dark time for the industry.

It was incredible. It had been a decade of that. I was an intern at the Philadelphia Inquirer four or five years earlier as an undergrad. While I was there they had done a 400-person round of layoffs, and that continued since. So, yeah we recognized that we ought not sign up for the newspaper lottery, and so two friends and I came back to Philadelphia where we had some network. It was a large metro market, and we kind of said let’s stay hunkered down here. This is a city we love, we do have some relationships. The newspaper jobs aren’t going to come, let’s just try something. And so with these two friends and other friends, we recognized we have to try something, we have to build our own life raft. Even if it’s just a life raft. And among the ideas, my cofounder Brian Kirk was already somewhat involved in a tech scene in Philadelphia. I had done some business reporting and had some interest in regulatory policy, and some business reporting. So we kind of married that together. Brian had said there’s a bit of a tech scene in this city of ours that nobody’s paying attention to.

Because you guys were going to events and there was huge turnout? Tech networking events.

Exactly. Brian had gone and said hey, there’s a couple hundred people at this thing and they’re kind of cool and kind of smart. This seems like more interesting than what you might think tech reporting has to be. And there was a national conversation that we were aware of, TechCrunch is happening and a lot of the tech sites were in that post-dot-com bubble that had burse in 2001. A lot of that was coming back nationally. So to speed up a bit, we just launched a Wordpress template, started showing up at events with stenopads, and did the journalism textbook version of what it would be. Learned a lot of lessons along the way.

How did the local tech community react to you? Because I’m guessing they weren’t really covered all that closely.

Right. So once they realized we weren’t, I don’t know, like secret agents are deranged lost people, and were actually trying to do something. Obviously, you’re at whatever sub-community that hasn’t yet broken into the mainstream, you’re hanging out and some 22-year-old with a steno pad comes up and says I’m covering this publication you’ve never heard of — because still in the 2008–2009 range, blogging is almost a decade old, but digital news is not quite a thing. Metro dailies, they’re probably still doing print first strategies. It was really strange to say I’m writing for a site. So of course we would look bizarre. But once people were introduced and read something we actually publishers and the first few people were OK with interviews. We did a mix of aggregation but there was also a lot of original reporting. Once people were introduced to it, then yeah, there was a sense of OK, these guys are actually professionally trained. Not that anyone knew what that meant in the communities we were serving. But then there was incredible enthusiasm. Once people were introduced to the idea of wait, you’ll do free press that will be written in complete sentences and have some narrative arc and I actually do want people to read. And you help me understand my own story? That seems incredible. And really quickly people racheted onto it.

What was the early sign that you were actually getting traction and developing an audience?

There’s a real answer and a hilarious answer, and I’m going to give you both of them. The real answer is that we did our first couple breaking news stories. And a lot of them were decidedly not quite what you’d expect out of a local tech news site. But there was a fire in the building of one of the firms we reported a bunch on, and Sean Blanda, the third guy who we started the original version of the site with, a dear friend of mine, wrote about that fire and that company wasn’t quite sure what they would do next. And then another company’s founder who read us reached out and offered them space. And that was the first sense it was two founders who we actually didn’t know but we had covered news, and people were using us as a platform, which is exactly what news always is. It’s in some form a content platform. That was maybe a couple months in. And that felt like, OK, things can happen because we shared information in a way that might have been on Twitter — Twitter was obviously still only three years old at that point. But there was enough traction among our community. It could have happened there, but the community we were covering hadn’t yet coalesced. So the people we were reporting on didn’t necessarily know each other yet. We were turning on a light in a dark room that already had people but they didn’t realize other people were in there.

That’s the real answer. There’s a brief one that — I am a great believer in self-deprecating stories, because I think organizational myth stories take out the hard parts, and everything was great, everyone loved us, and we were perfect. So I like stories of when it didn’t work. So a very vivid memory I have is maybe six or eight months. So a little bit after that story, and we were like OK, we’re a platform, we are something. People are reading us. We’re seeing real things happen. We probably had a few more examples of that where someone reached out to someone else because we wrote a story, and that person, that source, told us, wow I was shocked a bunch of people reached out to me after it. I thought it was this site. Who are all these people? That was all great. We did the inevitable thing. It’s Summer 2009, we’re starting a little news site. And we had done a small conference that had been relatively successful. So we’re going to do a meetup of our readers, and do even more introductions. What an incredible thing. And this is going to be the start of our business strategy. So we got a meetup, we got a venue. It was at a local makers space. We put out a post. We put out tweets. We were like this is going to be amazing. We’re going to shut this place down, because we just had an event with a couple hundred people. We’re the biggest deal ever. And it was horrifying. It was stil,l til this day, one of the worst moments of my life that literally no one is going to come. And we had this existential conversation — I remember the maker space organizer couldn’t actually come, so we were just using the space. So literally it was just the three of us. But last minute he had to pick up something, and he came back to the space and was like, is this the meetup? Yeah, this is the meetup. It’s just the three of us. It’s small even for a meeting. So we had this existential conversation on the sidewalk of, oh man, that’s humiliating. We can’t devote our lives to something like this. And we had this conversation of are we going to push through. And we said, all right, we need to do a version of this a few times more, and if they go like this, this isn’t working. And of course, we had a couple that ended up being successful. We learned lessons from that, which is important. But I like remembering there are so many humiliating, earth shattering failures throughout the pathway, and that’s one of them.

We’ve seen a lot of local news startups over the years, including Jim Brady’s Billy Penn in Philly. And we saw the DNA sites in Chicago and New York. And we’ve seen a lot of hyperlocal news sites. But yours was kind of unique because it was local but it was also focused on a specific vertical. Do you think people would be surprised that cities outside of Silicon Valley to have robust tech sectors to support a profitable publication?

Totally. And there are two trends in there. There’s a trend that’s relevant to technology. And there’s a trend that’s much more related to news, generally. The tech specific ones is I think we got pretty early — yes I’ve had that same question for the last 10 years of my life. For 10 years of my life, had some version of the question of can it sustain? What’s the metric you look for to prove it? I think, at first intuitively, and then later we were able to articulate what we understood was — we weren’t covering, and we were quick to chase away the narrative of what’s the next Silicon Valley. I think we got that pretty quickly of it didn’t make any sense, It was never going to happen. Instead just local economies are changing. The types of work forces that any city’s going to need to survive. That’s not what’s happening. Instead just local economies are changing. The types of workforce that any city at all needs is going to change, and we’re just covering the people who represent the vanguard of that workforce change. And once we grasped that, there was a sense of this is going to literally in every city that will still be in existence in 50 years. It’ll be able to sustain some daily narrative about that community. So I think we got that quickly to understand people thought this was dumb. It thought it was everyone chasing being the next Silicon Valley, and they thought that was a fad. I think we got that that would be a fad, but that’s not what we were reporting on. We were reporting on how local economies were changing and the workforces that make them up. And so that was the actual trend we rode, and are still riding. And we think it’s just a more normal part of — just like every city has a restaurant culture. And no one knows only Kansas City has restaurants, and that’s where all the restaurants are. No, this is what a city needs to thrive in the same sense that’s how we view a tech community. That’s one trend. And the more news oriented one, the one I think anyone is interested in how we inform communities, or dare we use the word journalism. I think I’m a believer that what the web changed wasn’t the content business. It was ad-supported content businesses, and those were, by nature, about scale, and there was a type when journalism outlets were the best vehicle for scale. And now it’s not. There are way more cost effective ways to build really massive audiences. And that’s what we call tech now. Instead, journalism is an incredible way to build relationships and build trust. It’s much more, we’re talking about business models that rely on trust. So for us we’ve done quite a bit with talent acquisition, that’s a category that we’re trying to be challenging in. In the same sense that subscription businesses are competing with membership groups. Or events businesses that we’ve obviously dabbled in. That was the big macro trend, that because we’re going about quality relationships, you can go really niche. We don’t need the biggest audience. We have a super small audience relative to your 20 person team. We don’t have millions of pageviews a day. That was a critical trend also, that the business model we were building was about a quality set of relationships, so niche makes sense. And geography is one kind of niche, but so is topical. And if you put them both together, you have really small, but really effective, way of getting a community together you can actually do — you can be a platform on it. That’s obviously what media is almost definitionally. You’re a marketplace between two communities, your readers and your sponsors. In our sense, the double niche helped that. And I think so often going too general waters it down

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And you guys figured early on that advertising was just not going to be a viable business model. At least to begin with, because you didn’t have a sales team. You didn’t have the mass market distribution. So you guys kind of — I don’t know if stumbled on is the right word — but you guys launched this thing called Philly Tech Week, right?

Apparently I have to turn all my answers to your questions with feature leads, but here’s one. I have a vivid memory of a couple months into what would become Technically Philly, hand trembling, calling a bar to ask if they would buy a $150 display ad. And it doesn’t make any sense. We can all say, why is a reporter for a tech site calling a bar to put a display ad? That is one of the single dumbest business sentences that could probably be written. And I was terrified. There was a lot there. I was still in my early 20s, but I had already become quite comfortable calling influential people and asking challenging questions. But just asking a manager if they would talk to me about buying something was one of the scariest moments of my life. And there’s a bunch of things that we got from that. One: out the outset we already were not particularly interested in advertising. Similarly, I think that was intuition first, and then that experience gave us the words to describe it. A lot of us, we were built on the intuition. We were three nerdy kids who followed the industry trends as undergrads, who came out with a lot of strong opinions. Like these stories often go, the ideas were probably right. We probably should harvest all the ideas from young people. They’re just shitty at execution or follow through or articulating. We should probably do more pairing where we take the 20-something’s idea but take the 30 or 40 or 50 something’s execution and articulation and positioning. Because after that hand trembling experience calling the manager, we were able to say the reason we were intuitively disinterested in advertising is because it doesn’t make any sense. Obviously that was a particularly bad example, but more to the point, we had a super tiny audience, and on the whole, advertising is about buying mass. That’s the point. Particularly on display advertising, it’s about scale, not calls to action, necessarily. So we got the words to understand that our intuition of being disinterested in advertising was dead on. And that April, we launched in February, I probably did the hand trembling call in March of 2009, and then April we hosted this little unconference for other journalists, and then quickly we decided we’d never pursue an advertising strategy. And 10 years later that’s true.We do a little bit of it, more just because it’s an inevitability. But it’s not at all a line item. That was one of the core tenets we got right, and I think it’s one of the biggest reasons we’ve been able to succeed this long.

How successful was that Philly Tech Week when you launched it?

That was the second half of the question I didn’t answer. Philly Tech Week took us two years to get to. We did a few events. We had that first unconference with industry peers. We had that incredibly embarrassing meetup where no one came. That led to us doing a Fall event. That was a pitch demo event that we sold tickets and got sponsors, and we probably made maybe a few grand. I’m not sure. But I think whatever the number is, it was incredibly big my standards by then and incredibly embarrassingly tiny now. But it meant the world. And that led us to a couple other events. And then we launched the big festival, which was Philly Tech Week. That was April 2011. Two years later. We launched in 2010 to do the sales cycle. It launched a year or a year and a half after we started showing up to events and doing reporting. So big events series. Distributed calendar. We as a group organized a few of the events. And invited others to be on the counters to grow its size. Sold sponsorships. I also don’t remember the number, but $20,000, something like that, in sponsorships. Maybe it was a little bit more. Because one of us came on full time, because I think we were paying ourselves maybe like $22,000 a year. It was a bit of a rallying cry. There were probably 15 events in the calendar. We did 150 events this year. But a few thousand people came out, and it just felt like this is something a news organization can do, we can convene. That, doubled with the advertising approach we took, probably really informed our idea that we were obsessed with hating the idea of — what is the business model of journalism? It is any business model, but just one that uses the value of journalism, or content, to strengthen it. You can be a car wash business that uses journalism to go get faithful subscribers. Or whatever. And so the idea of doing events, which was one of our first ways we were able to come on full time. We were doing subscriptions….If it’s native advertising, or all these things we’ve done. They are all businesses that exist in the world. They’re creative agencies or events producers. But you’re tackling it in such a way where journalism is part of the strategy. Journalism is a strategy, not an industry. Philly Tech Week was hugely successful, both in terms of revenue but also in terms of realizing who we want to be and how do we want to approach this world.

So how did you decide to expand outside Philly into new markets?

Organic outreach is the quick answer. A few people reached out from Baltimore. Baltimore is our first community. There was a membership tech council that was doing some coverage. There are some people — they don’t always use the word journalism — but there are people who say or like or understand, an independent newsroom, that idea of being challenging is how communities get better. A lot of people get scared or excited, but we were decided to find this crew from Baltimore who said this is what we need. We think our community is growing, there’s activity, we think this is a part of Baltimore’s future. But we don’t anything is calling bullshit on each other. So we wanted to do that. And we want someone to tell a narrative, and we want it to be a news source that wants us to succeed, but is also willing to say what needs to be said. We’re not dropping public affairs journalism every day. But the fact that we’ll do the coverage of a company’s layoffs, even if that company doesn’t want it, or we’ll do the coverage of accusations of spammy practices. Or we’ll do coverage on policies in local government. That was stuff they reached out and said we need it. They helped us introduce some early sponsors. But it was a mess, our first expansion. It was my co-owner Brian and I, and basically three of us started technicallyphilly.com. Built it up to full-time, and that was the point Sean moved on. Still a dear friend. Brian and I decided there is something here, we want to build a business, not just a blog. So Brian and I rebranded as Technically, and went to other markets. It was this sense that if Baltimore has interest, others can. But Briand and I were getting our ass kicked because we didn’t quite know how to do it and how to do it well, so it was a mess. We were two young reporters who were still trying to figure out how to do it Philly and didn’t know what we were doing. But organic outreach is the much shorter answer.

You’ve since moved to Brooklyn, Delaware, DC. What’s your MO when you move into a new market? You’re moving into a market that already has its own media markets. How do you ferret your way in and carve out your own space for your publication?

The metrics answer, we care about the number of IT and engineering jobs that are open now. That’s our more mature strategy of choosing to go to somewhere. We care about how many corporates there are. If there’s a university footprint. Economic development groups. Some early dollars that might invest in us. That’s how we look at expansion now. We’re doing a pop-up in Pittsburgh right now. It’s a wonderful community. So that’s how we first test out whether it makes sense. How we ferret in, that actually we have put a lot of time into thinking about that. I’m in our CEO role. I am typically part of getting our very first relationships. So I’ll do trips. There’s usually some community anchor who will introduce us. Often the community anchor will get together some of the key stakeholders. I’ll share what we do. They’ll share about their community. If we have some of the quantitative metrics that we can look up and do, then I’m there for some of the qualitative, how that community talks about itself. That’s a good way to introduce what we’re about, and we’ll get that first five, 10, 15, 20 community anchors to know us and to know that we’re looking at a community. We’re trying to be deliberate. Every expansion we’ve done, I’ve done a couple — two to three — dedicated trips to that place. And it’s probably from the first time to the expansion, about six months minimum. I think we need to shorten that time, but the point is we know local news often has authenticity challenges, particularly when you’re trying to do a multi-local strategy. So we put a little time there. But the actual expansion is we lead with editorial. We say have to burn a year to a year and a half before we’re really going to do much business strategy. Editorial’s tip of the spear. We are reporting on a community. We might find some strategic ways to fund that. Sometimes we do economic development groups. We’ll do some underwriting, some native advertising, at our launch. But really the answer to how do we ferret our way in, we do what news is best at. Building a cohesive narrative that mirrors that place so that place can better understand itself and the people and the community they’re in.

And you’re usually hiring a single reporter to start with in that city. I think when I profiled you guys back in 2014, you had just launched in DC. And you had hired a recent college journalism grad to basically be your anchor reporter in that city.

Exactly. And the offering gets better over time. There was a time when that was a contractor role. Then it was a part time role. Now it’s a full time role. Part of that is how we’ve been able to grow. But exactly. So it’s an editorial person who can be a little bit more competitive as we grow. It’s a reporter that we have a model and an editorial calendar and some structure. But we do give that person some range to find that. We have a lot of opinions. I as an individual have an idea of what beat reporting looks like on the web today. It’s one of the things I will happily nerd out with anyone. So we introduce to someone about how we approach things. There are a lot of patterns we find across markets. So we can give a reporter of a cheat sheet of what to expect. But then they roll. And it’s a really effective way to build relationships.

And how do you manage your hubs from an editorial perspective?

Every piece we publish has been edited by some other human. Which we talk about a lot about how we probably haven’t introduced that concept to the readers. We are always amazed when we get feedback. Readers don’t understand the media’s process. Everything is edited. We have an editor. They’re active on Slack. That’s a distributed editorial team. We have editors in HQ. We have Slack updates. There’s a Slack that’s very lively with joke trends. There’s also the daily check-in with the editor on Slack. There are weekly one on ones via call or check in. We do a monthly all team call where we’ll sometimes highlight an editorial trend, but share things across markets. So we do have a fair bit of newsroom sharing of here’s what I’m seeing in Delaware. It’s different from DC. What about Pittsburgh. That’s the value we offer, we try to say that’s why the multiple strategies are good, both from a scale side. We do have business folks in our community, and they can share best practices and what deals have worked. Hey, this partnership worked in this city, would it work over here? Or I know the corporate buyer for this region, it’s based in this other city but would be relevant. We do a lot of that knowledge sharing. We’re pretty tightly controlled in HQ and distributed with a lot of Slack. But we have weekly check-ins with calls, and the monthly all team call is a big one for our strategy. We do have, three to four times a year, an all person meeting. It might happen otherwise, but we have four main ways we see each other, and that’s good for the idea sharing too.

From a monetization standpoint, you have events. There you can both sell tickets and also sponsorships. You have a local jobs board, so anybody hiring for any kind of tech position, they can pay to monetize there. You’ve also introduced advertising. I’m guessing now that you have hubs in several cities, across all those sites you have a nice mass audience. Especially since you’re kind of dominating the whole Northeastern seaboard. You now have enough scale to where you can start to attract more typical mainstream sponsors, I’m guessing.

I’m probably the weirdest small media publisher in that I just can’t get excited by advertising. So frankly no, we probably do understrategize there. Our native advertising package, we do some creative work, I love that. I do put that in that category where it is still working with a client to get a call to action and tell a story. Though we have pretty high editorial standards, and have some nerdy policies around that that I’m really proud of. So long answer of yes, we work with more regional spenders. The AT&T or the Wells Fargo or the Comcast, the Vanguard, those kind of bigger brands we’re able to do more with. You land on the site, it’s not a display advertising — sometimes it’ll happen because there are targeted opportunities, or certain clients where it’s part of their strategy. Obviously we can technically serve that. But we talk a lot about — a lot of those teams we’re doing talent acquisition strategies. Yeah, it’s a jobs board, but we have a bunch in the subscription style where you can subscribe to basically bundled jobs that come with company culture write-ups. That category, for me, is so much more interesting and exciting. It’s a truly different business model to compete in. In talent acquisition. But it’s a long way of saying that yes, the multi-local does help for that strategy and the kind of clients we can attract. But yeah, still probably lingering on display ad shade, that you’re probably right I should get over that. That’s the real answer.

Do you think part of your success came because the tech press was too centered on Silicon Valley?

Yes. Definitely. I think even if it wasn’t, that’s what niche players are good for. There becomes a pipeline where, you know, when I talk to founders or CEOs about their media strategy, you should use regional general interest press for early support. You should read niche national publications that are for your investor class, or your larger enterprise clients. You should ping national tech press for a different class of investor, or perhaps talent acquisition strategies, depending on what your hiring strategy is. Really it’s a talent acquisition player, we’re read by technologists and job seekers and people interested in knowing that community. And the general early adopters wherever you’re headquartered. That was a way of saying yes, our early success was tied to their lack of interest. But even if there was a sense of them covering a bunch of different metro markets, they’d never be able to, nor would it fit their model, cover those markets deeply. So I think it was just a hole that wasn’t quite filled that we filled. And now others have joined in that conversation, I don’t know if they’ll ever be able to do it. That is the media as ecosystem narrative that you want a healthy robust ecosystem where people can get their stories told in lots of different places for different reasons. And collect different audiences.

How scalable is this? Could there be a Technically hub of every city of a certain size?

Yes. I absolutely think it. I like to think — we’re 10 years old, there were seven years of us working in the business where my cofounder and I were transitioning from terrified, inexperienced journalists to founders. And then in the last three years. We’ve been working on the business, where I’m probably aiming to be a better CEO than I was a journalist. And so with that further refinement of who we are and what we can be, I think that’s where we create efficiencies, replicate the model, understand our core principles. Know that trust is what we have that is most valuable and how can we serve the communities we’re in best, and sustain our work. But that’s what allows us to scale. Us five years ago, when we were working on the business, and working in the business. And Brian and I were quite a bit more inexperienced. That probably wasn’t going to happen. But yeah, absolutely.

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

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