A conversation with Esquire’s Ross McCammon

I admit that when I called Esquire Senior Editor Ross McCammon in mid-October to profile him for a class, it was in part an excuse to write about the inner workings of one of my favorite magazines. We ended up spending more time talking about McCammon’s journey to his dream pub.

As it turned out, that was the more interesting conversation.

McCammon didn’t set out to be a journalist. He studied English at the University of North Texas in Denton, outside Dallas. There, he got a job as a fact checker at Spirit magazine, the magazine of Southwest Airlines, which was rebranded in September 2014 as Southwest: The Magazine. That turned into his first job out of school, about which he thought… meh. He left. It took the chance to get in on the ground floor of a new publication to get him back into journalism.

That magazine, Travelocity, was doomed from the start, but they had fun with it on the way down. We talk about that at length below. He spent a year there, then several back at Spirit before getting a call: Hello? Yeah, Hearst here, mother of your dream job, are you interested? Coffee, meet desk.

May we all be so lucky.

Not that McCammon isn’t brilliant and hasn’t earn it. He definitely is and he definitely has. For Esquire, he created the Best Bars franchise, which sparked a show on the Esquire Network. His design work has helped the Man at His Best section earn six National Magazine Award nominations in the last eight years. And his long list of responsibilities at the magazine has continued to grow through the years.

Today, he also writes a column for Entrepreneur magazine and is working on a book. Follow him on twitter here.

Our full conversation is below. Enjoy.

What’d you study in college, was it journalism?

I didn’t have any real ambitions to be a journalist. English – those were classes that interested me, so I did that. Other than being editor in chief of my high school yearbook, I didn’t do any kind of publishing. I wasn’t super interested in publishing as a career, certainly.

So then did you end up doing grad school? What was sort of your first job as…

No, no. I actually, when I was in college I got a job as a fact checker at Southwest Airlines’ Spirit magazine, which is the in-flight magazine for Southwest Airlines. I think I was a junior in college. I got that just because somebody knew of a job, and I needed a job and it sounded pretty interesting. And I went, from doing that, I got a job right out of college. I didn’t do any kind of publishing program or magazine program or anything like that.

So, Spirit magazine when you’re in college. I’ve seen that they’re doing some longform type of stuff now. Has that always been the case? What was that magazine like?

It’s actually a good magazine. There’s a limit to how good those magazines can be because they’re sort of connected to the larger, corporate entities. So there’s this inherent conflict there. But it was really interesting. It’s really good for anyone in journalism, especially anyone going into magazines, to have been a researcher, to have been a fact checker. To see this sort of micro-focus that I think is really important throughout your career. To look at it word by word, sentence by sentence.

The most basic question for a journalist is, ‘Is this true?’ As a fact checker even at an in-flight magazine, that was my job. My job was to make sure that everything was true. And I think that was just a huge, incredibly important lesson for me. So it was a great way to start out my career. It wasn’t the best magazine in the world, but there was actual journalism being done, and that’s really all you need.

Did you start to think of yourself as a journalist at that point? I saw on your LinkedIn, it looks like you were at Travelocity magazine – which I’m just finding out existed now – before you went back to Spirit. I’m wondering sort of when you started to think about yourself as a journalist.

It probably was with Travelocity. I got a job out of college with the same organization I was with, the same publishing group that did Southwest Airline’s Spirit magazine, American Way magazine, the American Airlines in-flight. I got a job doing, I don’t even remember what it was, it was some web-based travel thing. It was really boring to me. Nobody knew at that point how anything web-based would work. Everyone was just trying things, and it just wasn’t very fun to me. I wasn’t working on a print product, and that always interested me more.

So, I left. I went back to school. I took some undergrad courses in design. I didn’t know if I wanted to be… you know, it just kind of soured me on the whole thing. So I ended up getting a copy editor job at an internet marketing agency. I was completely out of journalism. And then I got a call from a former colleague named Chuck Thompson, who is a fantastic editor and writer, and he worked at American Way. We got to know each other that way. He was going to be the editor in chief of Travelocity magazine and he called me up and just said, look, do you want to do this? And it just seemed like the right thing to do. And that was the moment I realized that’s what I wanted to do because there was just no option. Of course I would go back and work for a magazine, especially a startup.

And it was just a really interesting thing to do because it was pretty much doomed to fail from the start. For lots of reasons, it just wasn’t ever going to work out. But the staff was amazing. I worked with some amazing people. And you can’t find that magazine anymore, but if you read it, it is completely insane. It was just this gonzo — it’s just so wild. The stuff that we got away with, it was like this combination of Maxim and Esquire and Conde Nast Traveler. It was very, very bizarre. And needless to say, the people at travelocity.com weren’t huge fans of it. We were just doing our own thing. And more than that, it was just funny, irreverent. It was such an experience working on something that, we didn’t know if it would be around much longer.

It lasted only about a year, but it was a great magazine. So that was an amazing experience. So from then on, that’s just what I wanted to do. It was fun and it was interesting, and I seemed to be good at it. And it was the first time I was able to be funny, try to be funny, and try to make a funny magazine. For me, that was a really big deal.

You were there for the duration of that magazine’s existence?

Yeah. I came in one month after it started, but I was there when it ended. I can’t recall, but I think it was a little over a year.

So from there, you went back to Spirit?

Yeah yeah, it was the same publishing group, so when that magazine folded I was offered a job at Spirit magazine.

When you describe that Travelocity magazine… Have you ever read, what’s the Dave Eggers memoir, My Beautiful… (Editor’s note: Full disclosure, I would have accidentally named Kanye’s album, My Beautiful Dark Twisted Fantasy.)

A Heartbreaking Work of Staggering Genius.

Yeah. I drew a comparison in my mind to his description of the magazine he was working on in his 20s.

Yeah, absolutely. He was working on Might magazine, and that was a little different, right, because that was his thing. I think it was an independent publication and that was the whole deal, he was supposed to do what he wanted to do. We were sort of doing that even though we weren’t supposed to be doing what we wanted to do. We were supposed to be doing what this corporate entity wanted us to do, and also make it interesting for readers.

So yeah, I remember reading that, and responding to it and relating to that, a lot of those stories. Very, very different, but in some ways, it’s a really good point. I’d never really thought of it but in some ways, it is kind of the same. It’s just trying to make a good magazine.

Very interesting. So tell me a little bit about your time at Spirit. What did you start out there as?

I started out doing the front of the book. I redesigned the front of the book, which was the first time I’d redesigned something. And that was really interesting. It wasn’t very good. But it was the first time I could kind of do what I wanted, so I did. There was a colleague there named Chris Philpot, who was a designer there, and we just had a similar sensibility. He’s very funny and very smart, and he was really great to work with. So we started what has become a longtime collaboration with that gig.

So that’s what I did. I worked on the front of the book and I worked on feature stories and had the chance to work with writers. And it’s an interesting thing to do because it’s this massive readership, millions of readers, just so many people reading this magazine.

And captive, too. Not distracted.

Absolutely. Captive readers. It was just an interesting exercise to do that sort of thing because again there was a large company that had to be happy with the magazine as well. So there’s a lot of pressures placed onto that situation. I always advise people to work for a magazine they don’t want to work for at first, because it kind of forces you to make something interesting out of something that you might not find inherently interesting. And I think that’s a real challenge. I think there’s a lot of benefits to that.

That’s how I looked at my time there as an associate editor or whatever I was. It had all these limits and limitations, so how do you make something good anyway? So that was great. And one way you do that is just rip off magazines like Esquire, (laughs) and just make inferior versions.

Was Esquire – might be jumping ahead a little bit here – but was Esquire a dream job for you? Was that a magazine you’d been reading for awhile?

Yeah, definitely. I was a subscriber forever. All during this time, I was reading the magazine and kind of absorbing it. It was definitely my favorite magazine while I was doing all this stuff.

You were associate editor first at Spirit, and eventually editor in chief, correct?

Yeah, I was editor in chief. I was promoted. I almost didn’t do it because I had moved to Chicago, I was working from home. I almost didn’t come back. I didn’t really want to live in Dallas, and I almost didn’t come back to do it. But I’m really glad I did because it opened up a whole ton of opportunities for me.

I did that for about a year and that was really great because I learned how to have a staff of people. I learned how to get new writers. I learned how to redesign a magazine. I learned how to work very closely with designers, which I think is a really important skill, an underrated skill – collaboration with the design department. And just make what I thought was a readable, engaging magazine. So it was an amazing experience.

So now, nine years, it looks like, at Esquire. What did you come in as there?

I was a senior associate editor. But I’m obligated to tell you how I got hired here because this is by far the most interesting part of my life.


I was working at Spirit in Dallas and I got a call from a guy in New York. He said he was with Hearst Magazines and started asking me a lot of questions about me. He asked me if I’d ever be interested in moving to New York, etcetera, and I said I would. And then, finally, at the end of the conversation, I said, ‘Well, what’s this about?’ And he said, ‘Well, there’s a job at Esquire.’ I almost spit out my coffee. And he said, ‘Well let me pass your resume on to David Granger,’ who’s still my boss.

The next day, he said, ‘Well why don’t you come to New York?’ I came for one day. I interviewed with four people, including the guy who called me, and two senior people at Esquire, and the editor in chief. And I was offered the job before I was back in my hotel gathering my things. And I was taking a cab and got a phone call from the editor. I had a job offer before I flew back to Dallas, and I knew I was going to take it. So I had to figure out how the hell do I move my entire life in less than three weeks. How do I get an apartment. How do I do this, this, this. It was crazy.

What did he say he was looking for when he called originally?

He asked me lots of questions. He said the editor in chief here would kind of like the idea of somebody who wasn’t in New York, who was kind of an outsider. So I think I benefited from that. Although, I don’t know, actually. I don’t even know if that’s true. It might be part of the mythology that I’ve created. I think that he was looking for somebody who was right and was willing to kind of wait.

A.J. Jacobs, I don’t know if you know A.J., but he writes a lot of books now, and he used to be an editor at Esquire. He did Dubious Achievements. He did a lot of the funny stuff. He did a lot of the pop culture stuff. So they were looking for someone to kind of fill that role, and that was a pretty natural fit for me.

Oh, and the reason the guy called is because he happened to be on a plane and read the magazine. He happened to be flying from Long Island to Philadelphia, I think, and read the magazine and saw that I was editor and the he gave me a call Monday morning.

What have your responsibilities specifically been there and how have they changed through the years?

I do a lot of what I consider fun things here. I started out and I was working on Dubious Achievements. I created the Best Bars franchise, which we do every year. I was also tasked with creating a new section that goes before Man at His Best that incorporated letters, the table of contents, the editor’s note. And trying to make that a unified section. It had become kind of an editorial wasteland. My boss really wanted that to be an engaging part of the magazine. So that was a really interesting job to make that interesting. And we did. We ended up getting a National Magazine Award nomination for that. And it was just a really gratifying thing. We were creating something out of nothing. It was essentially wasted pages. So that was really cool.

From there, I’ve always worked on pop culture stuff. So, the interview at the front of the book. Film. TV. Music. Those are kind of my beats. And then I just kind of added onto that. I became the drinks editor. I’m now the cars editor. Those are things I have to be responsible for. But then I’ve done some writing, I’ve done some cover stories. And lots of other things. One of the great things about Esquire is that you’re not closed off, you can work on any part of the magazine. And if it’s a good idea, it’s a good idea.

What’s it been like getting out of Spirit magazine where you did have that corporate pressure, and coming to somewhere where there is a greater threshold for creativity?

It’s amazing. It’s the best. It’s a magazine I’ve always wanted to work for. And it must be interesting. It has to be interesting. It has to be good. And that’s the pressure you want. You have to be as good as the people who’ve done this magazine before you. And there’s no other pressure other than the pressure you put on yourself to do very good work. That’s what everyone should have. Everyone should have that kind of opportunity, and that kind of pressure.

So, it was amazing. It was incredible. If it’s funny, it’s funny. You don’t have to worry about sending somebody something in an office somewhere. If it’s interesting and engaging, if it’s a great story, if it’s great journalism, you just do it. And I wouldn’t trade having those limitations for anything, but I’m glad I don’t have them anymore.”

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