Mountain warning

From the Trenches: The best and worst moments of building the Daily Dot

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When you’re climbing a mountain, you don’t realize how high you’ve gotten until you stop to look back. Almost exactly one year ago, there was nothing more to the Daily Dot than a full-time CEO (me) and two part-time cofounders (Nova Spivack and Josh Jones-Dilworth). We were shifting strategy once again—this time, vowing to stop screwing around with fundraising and just get to market already.

Today, we’re like a real website and everything—with 19 full- or part-time employees and almost 240,000 monthly unique visitors*. Just four months after launch. Crazy!

But the end of the year is the season of lists and looking back, so here’s how we got from there to here, as a listicle: the five worst and five best moments in Daily Dot history.

WORST

5. Not making any money yet. We’re a startup. We were never expecting to be making money by now. I knew this was how it was going to be all along. But a whole year with only expenses? I would really like some revenue, please.

4. Losing our development lead. It was an amicable breakup, and we’re all still friends. In a startup, though, much like in a college relationship, you stay up late at night and dream big. So even though I believe all parties came out just fine, you hate to give up on any part of the dream, even if it’s just who’s going to be standing together when it comes true.

3. The leaderboards. We’ve got a big vision for the leaderboards, which I still believe in. I don’t have a problem with the fact that you’ve got to start somewhere and build from there, but this feature has stagnated for months.

2. Taking six weeks longer to launch than we thought it would. I grew up in a newspaper family. We live and die by deadlines, so while I am told that we actually did a pretty good job of launching on time for a start up, it still kills me and sends me into a tailspin of depression. It took longer to hire reporters than we planned. We did not manage the site development process as effectively as we could have.

1. Having to write again that we didn’t do what we said we would. Every month so far, I’ve had to tell the team, our advisors and board, and our investors, that we didn’t quite do everything we wanted to. We’ve gotten better, and we will get there, but I hate it every time we fail to execute our own plans.

BEST

5. Getting the paper out every day. Just the fact that we’re doing it is a great feeling. In print it was called the “daily miracle.” What should we call it online—the continuous miracle?

4. Traffic! We hit 125,000 uniques in September, our first full month. We expected that to decline before going back up and it didn’t. It stayed flat for a while and now it’s almost doubled! #boom, as the kids say in our chatroom.

3. Our comics section. Our comics weren’t exactly planned. We never put them in our strategic Gantt chart. We always loved the idea, but, well, we were busy. We had a website to launch. And then Liz Jones-Dilworth said, for, like, the hundredth time, “So you guys gonna actually have a comics section, or what?” And Josh said, “Why don’t you make one?” And she did. And it is good.

2. The team. OK, I know every douchebag CEO is like, I’m just so honored to work with these people. But I really mean it. I get to go to work every day with a ragtag crew of hard-working, surprising, often strange and wonderful people who are true journalists of the next generation (and I don’t mean just the ones who write and edit).

1. Getting to be a part of the online community. I believe deeply in the online community. Perhaps the most clarifying moment in my own life was reading Robert Putnam’s Bowling Alone. In that book, he argues that we are losing our connections to each other and that loss is the true weapon of mass destruction. It’s what solidified my belief in journalism and in the media. Imperfect as it is, the news is about connecting us, about helping us see over the fence.

I believe the Internet is also about connecting us, and I believe that connection is the foundation of peace, justice, and every other desirable thing in civilization. And, much like our own team, the Internet is wall-to-wall with interesting, exciting, inspiring, strange, and extraordinary people. We’ve gotten to meet some of them, and introduce some of them to you. We’ve gotten to help them tell their stories and we’ve helped others find their way into this diverse and delightful world.

*Please tweet/like/+1 this story. We’d really like to hit 250,000 by the end of the year. Hey @Mediagazer, can I get a RT?

Photo by itzafineday