Esquire editor-in-chief David Granger is figuring out how to make money in media again.

To do it, he’s making Esquire‘s bevy of articles and essays written by some of the most prominent writers of the last century available for a subscription fee. The new archive launched in tandem with its 1,000th issue. When tasked with finding a way to promote the product to readers, Granger tapped Shazam, a mobile app known for figuring out that song you recognize but can’t quite name.

This is just the latest way that Granger and his colleague research and development head Tyler Cabot have devised to “tell and sell” stories on the Web and mobile.

Shazam peppers throughout the latest release, appearing next to references to articles from the past. Taking a photo of the icons with the Shazam app sends readers to archival content. A reference to John Lennon might bring up a 1980 cover story on the legendary Beatles frontman’s life. For now, Shazam and Esquire‘s partnership isn’t financial. However, if Esquire were to use Shazam to direct readers to sponsored content, they might strike up a monetary deal down the road.

VentureBeat talked with Granger and Cabot on how technology can help fuel paid content on the Web and mobile. Here is an edited transcript of the interview.

VentureBeat: You recently struck up a partnership with Shazam to bridge references within your 1,000th issue to old articles. How did that happen?

David Granger: When we decided to do both the print magazine and the complete digital archive dedicated to looking back at Esquire‘s 1,000 issues, we wanted a bridge from the present to the past. In my editor’s note I wrote about this concept, I started talking to my staff about called the “eternal now.” Which is, because of things like iTunes or now Esquire‘s digital archive, the past is constantly present. You can always access it.

So, six months ago, I heard that Shazam, which is the fifth or sixth most downloaded app in the U.S., was introducing this print-to-digital capability. And so we, Tyler and I, took a meeting with them and some people from Hearst business development and agreed to become one of the magazines that would commit to using Shazam technology for this right off the bat. That’s why we did it. I wanted to be able to make references to our past in the 1,000th issue and then immediately take people to the items they’re referring to.

VentureBeat: When did you start experimenting in digital media?

Granger: In 2006, I had a dinner that I brought all the writers and editors in for. I asked my staff and contract writers to start over with what the concept of a magazine is. We actually started experimenting 2007-2008 actively. In 2008 we published the first moving cover of a magazine. We did this thing along with E Ink, which was kind of unknown then — later it became the basis for the Kindle, but we created an E Ink cover of the magazine in which words and images moved for the first time. It was kind of amazing.

And then shortly thereafter, we did the first augmented reality issue of a magazine, in which Robert Downey, Jr., was on our cover, and if you held it up to the computer, he would sing, dance, explain what the issue was about. Inside we had that actress from Community, whatever-her-name-is [Gillian Jacobs–Ed.], tell us a funny joke and if you came back after midnight she’d tell you [another] joke. Then we had Jeremy Renner in our fashion story changing clothes via augmented reality. It was hilarious, and we were the first people to do it.

We were the first magazine to have a regularly published iPad app. We’re one of the first magazines to have an iPhone app. So we’ve had this print-to-digital transition for many years, but the problem is that it’s very difficult to induce people to download a proprietary app.

VentureBeat: Are you doing anything different now than what you’ve done in the past?

Granger: We’ve always been interested in exploring new forms of creative expression, and this is a little more concerted effort to experiment with what technology makes possible but also to try and make money off of it.

VentureBeat: People are so used to content being free — how do you get them to pay for stuff?

Granger: I think there’s two strategies. Hearst has — at least in the magazine division, all of their digital offerings, with the exception of subscriptions for the iPad, have been free. Whether it’s Cosmo.com or Esquire.com or whatever. So we have been trying to experiment with a paid model. I think the whole media and entertainment industry has decided that’s one of the ways to go. It’s the way the entire music industry has gone. So we happen to be in the position, which is not true of every magazine, of having an amazing backlist. We have got 82 years of history. We’ve got 50,000 stories; 33 of those are by Ernest Hemingway. We have every famous writer in the history of American fiction and nonfiction, or world fiction and nonfiction, having written for Esquire at some point. So we feel we’ve got an interesting enough past and compelling enough past that we can induce people to pay $5 a month or $45 a year to have free reign over this.

Then Tyler took the additional step, which has never been done on our archive before, of actually curating it. So we curated this site with a design firm called Cantilever, which is the homepage to the archive, on which we make recommendations every day. We tie old stories to news events from today. We, on the day that Stephen Colbert took over The Tonight Show, had a collection of stories that Esquire has done on late-night hosts. So I think subscriptions are the way forward.

Tyler Cabot: I just think free is not going to pay for what we need to do going forward. Really, it’s about clearing out the best way to get people and give them something that is valuable and worth something. That’s one of the big things we tried to do with the site was create a great beautiful reading experience and make it necessary. And I’d say overall whether it was ‘the Falling Man’ experiment* or the archive or some of the other things we’ve done this year, we’re experimenting and we need to figure out what works and what doesn’t and change fast.

VentureBeat: Do you think curation plays a big role in helping to monetize content?

Cabot: What the big difference is that if you go to the New Yorker archive or Vogue or Rolling Stone, it’s really just you sort by issue, so you can see the cover of the issue, and you hit and you can read anything in that issue. But you have no real idea of what is actually in the issue. So we try to curate from the top down. So we built a special system in this flat form so that each issue, when you pull it up, shows you the top three highlights right there. You know; there’s no guesswork there. On the homepage we can say “read these five stories today, read Stephen King’s favorite fiction stories of the week. This new movie is coming out on ‘Whitey’ Bulger — read our five best gangster stories.” This is all new.

One of the things we did before we launched the digital archive [was launching] what’s called Esquire Classic. We did it for about four months to build an actual audience for the archive, but also the main point was to curate and say this is the one story you should read today or this week.

Granger: We [launched] it on the anniversary of Martin Luther King’s assassination. We ran this article from 1968 where Gary Willis actually went to Memphis and then rode to King’s funeral with the sanitation workers union, and it was like this vibrant piece that puts you right back in the 1968 civil rights movement. We surfaced it on the anniversary of his assassination. And we were doing that every week: finding a reason to surface a story, and there was a committed audience for that. I’m not saying it’s a big audience, but tens of thousands of people. And if we can get tens of thousands of people reading our archive, then we’ll have a very profitable archive.

VentureBeat: Have you considered other ways of allowing users to pay for content besides subscription?

Granger: Right now it’s subscription. I could see sponsorship, possibly. You know, I think the key here is we’re sitting on 82 years of paper with some of the greatest stories written whether it’s … [Norman] Mailer’s stuff or Tom Wolfe, Philip Roth, and now we have the capability to use it and to create a great reading experience from it. Up to this point we only had the last three, four years of Esquire online. Now we have everything else, and some of it is a very valuable asset.

VentureBeat: Would you ever consider a pay-per-article model?

Cabot: Absolutely, before Foley**, years before that in 2013, the first experiment we did with Tinypass was a single by Luke Peter called “The Prophet,” and that one I think was $3. And I’ll tell you what was amazing was six months later, there was no press on it, and we would still make $5 to $10 a day on it, which is better than having that article living on the back of some website. I do think there are some articles that people really need to find, and what we decided with archives is that if you really need this article, just sign up for the first month. The first month’s free, and we’re pretty confident that it’s a great product and that it’s something that you are going to stay with; otherwise people can cancel.

Granger: I think there is some potential in selling articles on particular occasions. I don’t think we’re necessarily going to be pulling apart the magazine on a regular basis. But if there is a regular article that we own digital rights to fully, then I think there is an opportunity, if there’s a news event that makes it suddenly important again to offer for a very low fee.

VentureBeat: Do you think curated archives introduces a new rabbit hole for getting lost on the Web?

Granger: The experience I kept having over and over again as we were creating this archive, and as we were doing this thousandth issue, is that I would find myself immersed in this old issue of Esquire I had no idea existed. There was an issue from 1960 — it was the New York issue of Esquire, and it was just an amazing collection of pieces, basically a prose poem to New York by Gay Talese. There was an amazing essay by James Baldwin called “Fifth Avenue, Uptown,” which is about his portion of 5th Avenue in 1960, which was a ghetto, not the 5th Avenue that everyone knows. There was an essay called [“Moving Out”] by John Cheever, just like one all-star of American literature after another writing, and it was just like you get lost in it. And it seemed immediate and relevant even though it’s from 55 years ago.

VentureBeat: Will this permeate to other areas of media?

Cabot: I mean curation for sure. … We are very unique in the sense that we have such a deep bench. There’s some great stuff at some of the other Hearst titles, and I think that you know the company will continue exploring that. In many ways this is the first major archive we’ve done here. The first one that is consumer-facing, for sure, and we’re trying to see where it goes.

Granger: Tyler took a year off to do a Nieman fellowship at Harvard, and it was with the explicit expectation that he would figure out sort of new ways for the magazine industry to move. And this is explicitly an experiment on the part of Hearst to see if this works and if we can generate new revenue streams. I do think there are other magazines here that could do this. I mean, Harper’s Bazaar has an amazing library. I mentioned Cosmo. … I mean Popular Mechanics has an incredible history. So you know there are many magazines that have lengthy histories to who I think this would be valuable, so we’ll see how ours does and then move forward.

VentureBeat: What else are you experimenting with, Tyler?

Cabot: I spent a year mainly at the business school and MIT trying to find ways to tell and sell stories and came back and we established this little incubator lab here and we’ve been working on stuff all year while doing this. So what we did was partnered with Medium, and we created a microsite for What I’ve Learned, and those are famous interviews that we’ve done every year or two for almost 15 years. Whether it’s with Gorbachev or Neil Young, pretty much anyone who’s amazing has done an interview there, and I realized we had this whole audience. And we worked with an amazing animation team, and we created these two-minute animations, about 10 of them. We then partnered with Medium, and we got Microsoft to actually sponsor the site, and it was a really cool thing. Again, it was using very old assets, old stories, actual audio performed this time, and we were kind of upgrading them and making them new.

Granger: One of the most interesting things that Tyler is working on right now is in combination with the launch of the archive he’s creating a series of podcasts with PRX [Public Radio Exchange], where we take a single story from the archive and we have a professional actor read excerpts from the story, and then David Brancaccio, the host of Marketplace, leads a discussion with one or more writers. The first one was “The Falling Man” with Tom Junod, and it’s gripping and it will be there for October.

We’re taking two other classic stories, Nora Ephron’s “A Few Words About Breasts” and “The Crack-Up” by F. Scott Fitzgerald, about having basically a nervous breakdown. This is yet another way we’re mining our past. And this will be advertising-supported. PRX has already found a sponsor, a few sponsors, for our podcast series, but it will be another revenue generator. It will also serve as promotion for the archive, and the archive will promote the podcast series with PRX.

VentureBeat: Everyone has a podcast these days. …

Cabot: We feel the same way!

VentureBeat: Monetizing a podcast seems like an art, not a science. What are you finding? 
 
Cabot: We’re brand-new. With PRX, we’re in the 1 percent that launches with sponsors. But again, it’s another experiment we’re going to figure out. And if it goes well, we’ll keep going. It’s a very busy space right now, and I think it was a very unique challenge. You know, what do you do with an old magazine story? You know if you read it, it just feels crusty.

Granger: I mean podcasting is in a weird moment. It’s extremely popular, but it’s kind of where the free Web has gotten to. Advertising isn’t going to support everything. So there will be a big filtering out of podcasting efforts that just don’t gather a big enough audience. We’re hoping that we can aggressively promote our efforts there and through the magazine.

VentureBeat: Are there other people in media that you think are innovating in interesting ways?

Cabot: I don’t know that we’re looking at other magazines, as we’re looking at everybody in every different sector.

We’re in a place where we need to think well beyond what we’ve done every month for 82 years. We have to have a new way to get our stuff in front of other people, because it is competing with everybody.


* In 2013, Esquire wrote a new introduction and put up a paywall on its most-read story, “The Falling Man,” which was linked to in a feature about the execution of journalist James Foley. “We asked people to contribute to the James Foley scholarship fund in order to read the new introduction and ‘The Falling Man,’ and we raised a significant amount of money, what was it? I think $25,000 or something. We asked for $2, and people were giving us an average of $5 or $4,” said Granger.
** Refers to the pay-per-article experiment explained in the above footnote.

Update: This article has been corrected to reflect the spelling of writer Gary Willis, who wrote a 1968 article on Martin Luther King for Esquire magazine. An earlier version referred to him as Perry Wells.