Quit Your Job, Live the Dream: A Q&A with Mark Armstrong, Longreads

The Awl: Mark Armstrong, you had a perfectly nice job as the Director of Content at Bundle, and presumably before that you had other real jobs, and then you went and quit your job to really focus on developing Longreads, which, duh, draws attention to longform writing. Why did you do that?

Mark Armstrong: So, here’s the thing: I’ve worked in the Internet coal mine for more than ten years now. I moved from Los Angeles to New York in 2001, and in that time I worked for both giant companies and tiny startups. During this time I noticed that the stuff that works best is a.) driven by people who are truly obsessed with what they’re building b.) useful to people as a service, and c.) resonates with an audience fairly quickly. With Longreads, I realized I was obsessed with the idea, and other people understood, liked it and found it useful, so for me I really had no choice. I had to pursue it or I’d kick myself in two years for letting it pass. Didn’t happen overnight, though: I spent a year and a half doing it as a small side project on Twitter, and that helped me determine what this thing was supposed to be.

The Awl: I have also always been told by VC and angel types that entrepreneurs have to be obsessed with their project, and that’s an indicator of future success. So your obsession is good! So, since you pioneered at Bundle the personal finance interview, I feel free to ask you this: how did you take your side business and make it into a real business? Did you sock away a little cash? Did you sell your sneaker collection?

Mark Armstrong: My sneaker collection is pretty horrendous. That didn’t get me far. But yes, that’s also part of the whole “preparation” thing, which was making sure you can afford to go a little while on the lean side as you build it out. I felt good about my window, but that’s the most important piece. And speaking of Bundle, I’ll refer readers to Logan Sachon’s interview with journalist Matt Davis, in which he talks about saving money as the critical element to having personal and professional freedom. Unless you have that financial cushion, you are not going to have the freedom to build your own thing. By the way, it’s also not an all or nothing thing. I still do quite a bit of consulting and freelance.

The Awl: Oh well, that’s very fancy of you. And I have heard of this thing called “saving.” It’s a fascinating concept. It seems like it has some value, maybe it will catch on. So what you have now is what they call a “multiplatform” vehicle: you have a well-followed Twitter account, a devoted hashtag, a Tumblr interface, a weekly email and a very nicely done website, with a searchable database. And you encourage people to use accompanying products in the market — Instapaper, Flipboard, etc. So do you have a sense of how you make this thing that people love — or really, this community, because Longreads is actually a community — and make it into a business?

Mark Armstrong: Well, the big goal from this entire thing was to rethink the media property as a service, rather than just one site. We existed on Twitter long before we launched Longreads.com, so that actually helped us clarify how we wanted the entire product to work. Longreads.com was created to do the things that Twitter couldn’t handle as well — archiving the thousands of long-form stories we’ve posted over the past two years, adding context with elements like word counts and reading times, quotes from the stories, and author and publisher pages for readers to browse their favorites. Without giving too much away, we think there’s value in this approach, and there are certainly ways to monetize through methods that don’t disrupt or degrade our (and the entire community’s) service to readers. They want the best stories from everywhere, they want it on their own terms, they want to take it with them on their phone through apps like Instapaper and Read It Later, and they want it from a source they can trust.

The Awl: In conclusion: how many nights a month do you wake up in a cold sweat thinking you’ve made the wrong choice?

Mark Armstrong: Never. Usually I’m just awake at 3 a.m. reading 25,000-word Scientology stories from The New Yorker.

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