Featuring Kurt Andersen, host of radio show Studio 360, co-founder of Spy magazine and media news site Inside.com, and former editor in chief of New York magazine; Erica Cerulo, co-founder, Of a Kind, a fashion and design retail site that was acquired by Bed Bath & Beyond in 2015, and former editor at Details and Lucky; Choire Sicha, New York Times Styles editor, co-founder of The Awl blog network, including The Awl and The Hairpin, which closed in January; and Elizabeth Spiers, founder of The Insurrection, a political consultancy for progressive candidates, co-founding editor of Gawker, and former editor in chief of the New York Observer.
Gabriel Snyder: What inspired you to start a business in the first place? Why not just go get another job?
Kurt Andersen: Well, I had a job [as the architecture and design critic for Time magazine] and I was trying to not have a job—it wasn’t about starting a business. As Graydon [Carter, co-founder of Spy magazine] and I became friends, we started talking about the magazines we’d loved when we were younger that weren’t around now, and just as a lark, we thought, what would be that magazine today? Well, it would be funny, and it would be honest, and it would report all these things that we hear at the bar from our journalist friends and never get published . . . and it would be funny.
So it began, really, just as a way to have lunch, and to have Time Inc. pay for our lunches, and dream up this magazine.
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Then, at a certain point it seemed like, well, maybe we should really do this, and my wife, Anne Kreamer, introduced us to a college friend, a business guy, and that was sort of what we needed to make it go beyond just a larkish pretext for lunch. It wasn’t that we wanted to start a business but, you know, there was no internet then, so starting a magazine is what you did if you were us and you had the inclination to start a thing.
Erica, do you remember when you first wanted to start a business?
Erica Cerulo: Yeah, I definitely didn’t recognize it as entrepreneurial spirit at all. I was looking for a sense of ownership, of wanting to create and build this thing and have the vision to bring it to life.
I’d started working in magazines in 2005, and I was starting to see that the role of editors [was] really changing. It felt like I maybe wanted to be an editor in chief of something. So when we came up with the idea for Of a Kind, it became very interesting to me, not relying on this advertising model that had fueled media, and to be able to sell the things that we were writing about as our revenue stream.
People on the business side of media really like to ridicule the business sense of editorial employees. Do the skill sets overlap, or are they distinct?
Elizabeth Spiers: I co-founded a nonprofit when I was in college, and as a result ended up in a startup right after school. After that I was a buy-side tech equity analyst. I was concerned when we were doing Gawker that people wouldn’t take me seriously as a writer, and for quite a while, they didn’t.
I had a sort of quasi-stalker who followed me through five different jobs anonymously and kept explaining to me that I would never make it in journalism because I was a fraud, because I hadn’t paid my dues, and I didn’t go to J-school. I think I overcompensated for it, but then it backfired on me, where I got pigeonholed as a writer. I would go into business meetings, and I would have potential investors or partners look at me and say, well, you’re a good writer, but what do you know about business? I think sometimes when those criticisms come out, the people on the business side just don’t like the idea of you not staying in your lane.
Erica, I’m curious about your experience. I can see where you’re drawing on your work in magazines, but it’s different when you’re actually selling stuff.
Erica: I mean, we knew nothing—my business partner nor I—about retail when we got into it. One of the first steps we took was taking this summer class that Elizabeth offered for two summers, I can’t remember what it was called . . .
Elizabeth: I had a little bit of free time and I wanted to volunteer on some level, but I couldn’t find the thing that I wanted to volunteer for—which is that I wanted to [teach] young entrepreneurs who didn’t know how to set up a business. I said, It’s not a technical nonprofit. I’m not taking any money, just send me your business idea and apply. I got something like 28 applications for the first class, and I was enormously delighted that most of them were women entrepreneurs. Clare and Erica were in my first class.
Erica: One thing that transfers from being a journalist or an editor directly into running a business is your sense that you can find the answer to a question, that you can do the research and get to the bottom of something.
Kurt: And you are willing to actually do the gritty stuff, which every journalist, god knows, does herself or himself.
Erica: Exactly, like learning how to charge New York State taxes; you just figure out how to do these things.
Choire Sicha: I mean, you started a real business, but a lot of us started media businesses, which, most people will admit, aren’t real businesses.
Elizabeth: Well, I would say Erica and Clare sell actual things that you can hold in your hands . . .
Kurt: I think you guys are saying the same thing. It’s a matter of temperament, and whether your background was working at a magazine or at a newspaper, it’s this kind of all-in, obsessive, convince people to do things, to get it done. And to me, it overlaps a lot with the kind of journalist I never was, which is the actual shoe-leather reporter kind of journalist. Those people are entrepreneurs.
Are journalists who start businesses in a boom prepared for the downturn, or is that a different kind of skill set?
Kurt: I approach almost everything in life with a tragic sense of doom just ahead, so I was never surprised when things got hard. So again, I think it’s a matter of temperament. With Spy, we were able to raise money from people, many of whom had just made a lot of money in the beginning of the bull market of the 1980s, and then by 1991 there was a recession. I think people can be, if not fooled, at least encouraged to think it’s easier than it is in the long run.
Choire, what was the hardest or most surprising part of actually operating The Awl as an LLC?
Choire: It’s pretty [much] all horrific. I don’t see a huge line between job-having and being an entrepreneur. I’m always prepared to be fired on some level, so it seems all very temporary.
I mean, honestly, like any kind of legal framework, you make some choices in a business. We made some really weird choices with The Awl about ownership. We shared ownership with people who maintained websites and people who worked on the websites, and at a certain point, we were like, We have to paper this, and then the lawyers were like, What the hell did you do? and we were like, We’ll figure it out! It was just an unending nightmare. I’m not sure we actually even finally figured it out before the whole thing ended up in the warm arms of the grave. At the end I was just happy to be doing the Paypal and the bathroom cleaning.
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Elizabeth: There’s an analogy that Reid Hoffman uses—he’s the founder of LinkedIn—which is that entrepreneurship is like jumping off a cliff and building an airplane on the way down, which I agree with. But what he doesn’t mention is that 99 percent of the time you crash.
Erica: One of the things we always talk about when we talk about selling the business is that the stress before was existential. The stress now, it’s the same amount, but it’s just bureaucratic, corporate stress, or just the stress of being managers. But it’s not, Oh my god, are we gonna make payroll? Or, What’s our runway like? Or, What happens if we take this risk?
Well, I feel like we’ve gone in sort of a dire direction.
Kurt: Choire took us there.
I did, too; it was partly my fault. So what are the good parts of running your own business, being your own boss?
Erica: You don’t have a boss.
Choire: Yeah, it’s great.
Kurt: The one time in the last 30 years that I had a real job was editing New York magazine, that they fired me from. I realize I am done with that, you know? Things can collapse and this might not work, but simply being the captain of your own little . . . not even ship . . . boat, is a pleasure.
Elizabeth: I think I might be the only person at this table that actually gets off on the making-payroll-in-a-month kind of scenario. I enjoy it, and I enjoy the idea that you can evolve what you’re doing very quickly. I guess that’s startup speak, but it’s the idea that you can change on a dime. I think if you enjoy entrepreneurship, it’s probably because you have a little bit of a novelty-seeking gene.
Choire: I think I don’t like jobs because I’m very bad with male authority figures. Like, now that I have a boss, and they tell me to do things, I just like do the opposite, basically. So, I mean, working for myself is sort of the only answer, I think.
Kurt: Is this your resignation from The New York Times?
Choire: No! I need the job, I’m an old man, I need the money!
Elizabeth: There’s also an inherent thing, though: If you’re a decent journalist, you have a problem with authority anyway, which makes you a difficult employee.
Choire: That’s true. And not a good thing for my retirement.
Kurt, you mentioned that one of your founding inspirations for Spy was to not have a job; I was wondering if anyone else shared that.
Erica: I was pretty scared to start my own business. I am pretty risk-averse in general, and I remember the thing I was super stressed about when we quit was not having a schedule and not having any place to be. I remember sitting down with Clare in the café above Whole Foods being like, Okay, so we need to figure out where we’re going to work on what days, and I need to know where I’m going on Monday, because just working separately from home was not gonna do it for me.
Kurt: I certainly considered myself risk-averse until we started Spy. I was 31 years old; I’d never taken a big chance in my life until then.
I think this notion of being risk-averse actually has changed a lot, because now, having a job doesn’t feel terribly secure. I wanted to bring up another topic, which is how has it been dealing with the business press?
Choire: I always did feel like I was sort of being manipulative with the press. They just need a good quote. I mean, all I desperately want is for anyone to say something funny, so I would just be like, What horrible thing can I say that they’ll print? Then I am a horrible person, but everyone’s happy in this transactional way.
Elizabeth: Well, you have to tell a story . . .
Choire: Yeah, that’s right.
Elizabeth: . . . and you know how to tell that story, because you know what people are looking for.
Kurt: I feel grateful that back when I was starting Spy magazine, there was no social media, there was no internet, so it was, yeah, okay, the advertising columnist for The New York Times is going to do a story. He does it, fine. That’s that. You didn’t have the quasi-news coverage that social media provides of everything, and probably this conversation as we are having it now.
Erica: This is a real struggle we had with fundraising in general, of being able to paint this picture and tell this story; we always played it too straight. We were realistic about what we were going to do with the business. I think people who come at this with more of an entrepreneurial background, or just have different demeanors, are able to say, Here’s what the hockey-stick growth looks like.
Kurt: Was that in some sense a female self-sabotage thing?
Erica: I think partly, or just like a female way of thinking that we both ascribed to.
Kurt: Honesty.
Erica: Yeah, this idea of “honesty.”
Is honesty—or not liking to lie—sort of an occupational hazard of being a journalist?
Elizabeth: You give people what you think are realistic trajectories, because if you don’t, you get punished for them as a female entrepreneur in ways you don’t if you’re a man. If you’re a man, it’s a display of confidence; if you’re a woman, it’s a display of arrogance.
Well, you know, journalists don’t like to fail very much, and entrepreneurship, as you said, Elizabeth, is something that often does involve failure. I’m wondering how you cope with that.
Elizabeth: For me, Donald Trump has tested this aspect of my personality: I always thought I had a pretty good imagination with regard to the way things could go wrong, which I think is a journalistic talent, and it comes in handy as an entrepreneur.
Erica: I feel like I’ve taken kind of the opposite approach and try not to think about anything until it happens, because I can start spiraling really fast about all the things that can go wrong. Unless it’s actually a problem in front of me, I try not to think about it.
For many people who work inside media organizations, “thinking entrepreneurially” is a very en-vogue thing that management is saying. How much does that have to do with actual entrepreneurship?
Choire: I think about this a lot, because I’m really a workplace-culture junky. I have a theory I’m still trying out, which is the idea that we should be entrepreneurial is just anti-millennialism.
Kurt: Really? I would argue that it’s against old people. Or against people who have worked for decades. You have to be entrepreneurial, old man!
But I think it might be also just back to the question of staying in your lane. At its best it’s saying, Hey, don’t just stay in your lane, think of other ways we can do this.
Choire: It’s really hard in a newsroom to look up and try something new, though. Newsrooms are built upon people being very face-down at a desk.
Kurt: I mean, real newsrooms of a daily, hourly kind . . . . How can you get your nose out of whatever it’s in to think in business development terms, or whatever that’s supposed to mean?
Elizabeth: It’s convenient for news organizations when margins are being pressured to say, Go be entrepreneurial, because it’s a sexier word than saying do more with less.
Choire: Journalists are not typically great businesspeople—present company excluded. I don’t think I want to see a lot of business thinking from journalists, particularly. I don’t think they’re great at it.
What kind of journalist would you encourage to go start a business?
Choire: I mean, it’s gotta be better than most of the jobs out there. Is that a terrible thing to say?
Elizabeth: I think it’s absurd to believe that starting a business is going to be easier than being a journalist in this job market. I was a columnist at Fortune for a bit, and I got the contract because I had started a Wall Street site called Dealbreaker. I had an office at Fortune, and there was a guy who was sort of peer-level to me who was not happy about it, because I hadn’t gone through the normal channels to get a column at Fortune. I hadn’t interned; I hadn’t come up through Time Inc. infrastructure. At one point he came into my office and he starts grilling me about how I got the job, and I said to him, “Well, here’s the thing: I started a Wall Street site from scratch, I built up the traffic, it had some readership.” And he looked at me and goes, “But you never did the internship here.”
In this guy’s mind, going up the traditional way was somehow easier than starting a business from scratch, raising money for it, hiring people, monetizing it, growing the audience—in his mind, that was easier.
Are there any personality types you would say are particularly cut out for entrepreneurship?
Choire: There’s a difference between the lone people and the partner people. I can’t do any of this alone.
Elizabeth: If there’s a difference, it’s that I have less of a sense of self-preservation than the rest of you. I have a high risk tolerance. Actually, the hedge fund guy that I used to work for used to tell me that I had a very high tolerance for pain, so I do think that’s a piece of it. It’s the “if you can deal with a lot of uncertainty and you like it” that probably makes you cut out for this sort of thing.
Erica: I think you have to be passionate enough to accept that you’re only going to spend 10 to 20 percent of your working time doing that thing you’re passionate about. Because the rest of it’s gonna be the bullshit that makes up the rest of a work day.
Kurt: There is more bullshit involved in being a boss of anything than there is in just being a journalist—any kind of journalist—whether you love what you’re doing or not. Like, it’s mostly just typing the words. It’s doing the thing rather than talking to Joe about his unhappiness being in that office.
Choire: Actually, I would say everything’s an office now, that’s the Wing-ification of everything, right?
Kurt: Yeah, exactly, and we’re all getting fired!
I feel like we’re getting close to the sort of “brand is you” territory. Is that the same thing as entrepreneurship? I see heads shaking . . .
Kurt: No! “The brand called you” is just thinking of yourself as a free agent in the world, more than my father did, you know? But I don’t think it’s connected at all, and obviously it devolves often to just sheer self-promotion.
Elizabeth: There are people who have built businesses around personal brands, like Gary Vaynerchuk or Seth Godin. Those are really outlier businesses, because you can’t scale them. They’re more like what VCs derisively call “lifestyle brands.” But then they also give money to Gary Vaynerchuk and Seth Godin because they think of them as something that you can’t replicate. If the core brand literally dies, you know what happens to the business?
Kurt: Although we elected a president who was just a brand . . .
Elizabeth: That is true. And ran a terrible business, too.
Is it possible to be a journalist and an entrepreneur at the same time?
Choire: I don’t mean the term derisively, but the airport book writers that we all know and love, they are a business, but they pose as journalists or are journalists also. It’s an interesting case that these people are monster brands or, for lack of a better word, are enacting journalism. It didn’t work out for some of them kind of spectacularly recently, but I think that’s when their business got in the way.
Elizabeth: It’s really hard, when I think of somebody who’s written something I’ve found useful and also ran a company. Anybody who’s a writer knows you need a certain amount of solitude, and the entrepreneurial lifestyle is pretty much the opposite.
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Gabriel Snyder is a contributing editor to CJR.