VOL. I: EPISODE: 1, 2, 3, 4, 5, 6, 7, 8, 9

VOL. II, EPISODE: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12

EPISODE 1 (2007 – 2008)

No matter what happens, remember, you can always go on a hot fog safari

So at this point in the story, the Dig has been a subsidiary of the Philadelphia-based Metro Corp.—which is also Boston Magazine’s parent company—since 2004. Will the Dig and Metro Corp remain partners forever? Let’s find out… 

JOE KEOHANE (editor-in-chief): I think I left the Dig in January of 2007, and then I worked at Boston magazine for about a year-and-a-half before I moved to New York. But working in a quiet, professional environment … I did not have the tools to cope with that. I remember being bored out of my mind immediately. It was almost like a panic. It wasn’t a smooth transition into respectable society. 

LISSA HARRIS (managing editor): Working at the Dig ruined me for regular employment. The next office job I had after the Dig was an internship at a technology review. The office was like a tomb, and there was such an intense hierarchy that people would look at you funny if you spoke up in meetings, especially if you were me, because I was this whalishly pregnant intern. I would open my mouth, and people would go, “What?! The impertinence!” The office culture was just suffocating. You couldn’t go from the Dig to that. So, a bit later, I started my own news outlet.

CHRISTINE LIU (lifestyle editor): After [Michael] Brodeur was like, “We have a lifestyle editor job open,” and, like, “do it,” I started by figuring out what I wanted to do, then figured out how to do it later. I remember I wanted a hot dog spread, and I wanted it, like … you know how Younique makeup ads are? When the lipstick is, like, smooshed, and it’s an almost grotesque visual? I wanted five hot dogs piled onto each other like a bunch of really expensive handbags. I still remember going on this huge hot dog safari all over Boston and going to the butcher shop that took forever to get the Kobe hot dogs, which, in 2007, were big deal shit. Look how far we’ve come.

MARTIN CABALLERO (eventual associate music editor): When I went in, maybe a couple times a week or something, I was one of many interns. That stood out. But it was really cool just to walk into the office and think, “Oh shit! I’m at the fuckin’ Dig! This funny, provocative, awesome, alternative voice that I’m totally down with.”

GRAHAM WILSON (founding sales manager): Boston Magazine kept saying, “You can’t print that, maaan! You can’t say that, maaaan!”

DAVID LIPSON (Metro Corp. Chairman and CEO): There were those nagging cultural issues of, “Can we be a little bit more upbeat and aspirational?” But because I was older, I didn’t want to dictate the content. I felt like that would be really stupid. I would coach, but not make strict demands. The Dig was not targeting me. It was targeting younger people. 

CHRIS ROHLAND (co-publisher): The sales team at Boston Magazine didn’t get the Dig as much as we did, and I think we were willing to play ball with them more than they were willing to play ball with us. At the time, the economy started sucking a little bit, and I know David Lipson was concerned about keeping the mothership [BoMag] afloat.

STEVE BARIL (sales rep): The one thing I’ll give Jeff credit for is he always tried to stay true to his original vision. What I won’t give him credit for is taking Metro Corp.’s money and saying, “I don’t want any input.” You can’t do that. It doesn’t make good business sense.

JEFF LAWRENCE (founding publisher): Boston Magazine never had any control over our editorial. We never censored any of our content, and I fought them tooth and nail. We were a renegade fucking ship and it was awesome.

LIPSON: When you’re out of your wheelhouse, you’ve got to try to manage it as best you can. You can’t impose your will on other people … Well, you can, but it’s never going to work. You have to have a shared vision as to what you want, and I don’t think I ever got that shared vision with Jeff.

MICHAEL BRODEUR (music editor): It’s not as if the presence of Metro Corp. prevented anything I would’ve done at the Dig from happening. If anything, having Metro Corp. there increased the comedy factor, because it was a hardass financial institution and someone in some boardroom gave a shit about how we were doing. So acting like assholes, all of a sudden, felt a lot more important.

LIPSON: The recession affected business across the board—media companies in particular. The Dig had approached breaking even, and then we lost Joe Keohane and one of our key sales people, but we were so close to getting this thing on its feet and where we wanted it to be.

ROHLAND: The decision was Jeff would take the Dig back and build on what we all worked on together. I think he looked at the relationship with Metro Corp. as a way to grow and get some help on the editorial side, bring in better people and stronger voices, redesign the Dig and make it a little sexier for a while, and really try to be a little different but stay dirty. I think we accomplished that. But the timing just wasn’t right for the Metro Corp. guys.

LIPSON: The gratuitous use of foul language would sometimes get under my skin. That kind of troubled me. But a friend of mine who’s a Texan, he tells me, (imitates a Texas accent) “David, more money has been lost in the search of synergy than anything you can think of.” He’s told me that a number of times, and it always makes me think back to my adventure with the Dig when I thought there’d be tremendous synergy. The Dig would be this younger version of Boston Magazine, and it would be this beautiful thing. But business is always a lot more interesting and easy in the abstract. Youth is incredibly attractive to advertisers, so I thought this thing with the Dig was going to be a freaking layup.

WILSON: They thought we were just a bunch of fuckin’ scumbags putting out a paper, having a good time, smoking a bunch of pot. But they couldn’t give up that ultimate control and let us go nuts. We were going to have no readers if we started putting movie stars and Tom Brady and bullshit on the cover. No, we were going to put two fat guys making out and go fuck yourself.

LIPSON: Let’s just say I wish I could wave a magic wand and go back and talk to myself at that point. I’d say, “Dude, it’s all about the internet. Start focusing your time and money there,” because who knows where that would’ve led?

Next Episode: The Dig spends all its money on glossy covers everyone hates.