In our latest episode of Earned, we sit down with Jason Wagenheim, President and Chief Revenue Officer at global media company Bustle Digital Group.
To start, we dive into Jason’s long-spanning career in publishing at Condé Nast, with stints at Vanity Fair, Glamour, and Teen Vogue. Jason reveals how accurate “The Devil Wears Prada” was, then unpacks how digital publishing took the print world by storm. We learn about the triumphs and challenges of acquiring and integrating a portfolio of independent media companies under one roof, including Elite Daily, The Zoe Report, and Inverse, before Jason emphasizes the importance of being comfortable with change. We discuss how publishers were the original influencers, and why advertisers should continue to see their value. Next, Jason shares the learnings he’s applied from his background in sales, and explains why empathy is key to being a successful leader. We close the show with the origin story of Jason’s current side hustle and passion project: East End Cowboy barbecue sauce.
We’ve included a couple of highlights from the episode below, but be sure to check out the full video above, or tune into the podcast on Spotify, Apple Podcasts, and Google Podcasts!
The following interview has been lightly edited for concision.
“It was the Wild West”: Jason Wagenheim on the Evolution From Print to Digital Publishing
Conor Begley: When I was looking at your career, you went through the bloodbath transition from physical publishing to digital publishing. I think right around the time The Devil Wears Prada came out  was when publisher revenue hit its peak; it was about $46 billion at that time. Then just over the next five, six years, it got cut in half down to about $24 billion. What was it like to be at the center of that transition? When an industry goes through so much change in such a short period of time, specifically from outside influences—social media blew up that business model for a little while.
Jason Wagenheim: It did, and it's a critical time you're talking about in 2006, because I think the iPhone came out in either 2007 or 2008, and the iPad was in 2009. Social media was around in 2003, 2004 with things like MySpace and Facebook. The critical juncture for that change from consumption was not so much social media, but it was when social went mobile, and all of a sudden you didn't need a Canon point and shoot camera that had like 128 megabytes. You had this really great camera in the palm of your hand, that was also your phone, that was also connected to the internet. You had apps, you had mobile websites, responsive design. That was the critical change.
Once that started happening, the re-adjudication of what Condé Nast did or didn't do back in the early aughts was up for discussion. What the mistake was at Condé Nast back in 2000, 2002, was launching brands like Style.com or Epicurious.com or Concierge.com. These were the internet homes of brands like Condé Nast Traveler, Vogue, GQ, Bon Appetit, and Gourmet. I don't think Condé Nast fully appreciated how well their brands could travel online if they just stuck to the brand. There was such fear that print would have massive attrition, advertisers would flee print for the internet, and “let's protect our core business that's 99.9% of our revenue by almost imagining the internet didn't exist for these brands. Let's launch other things around it.” I'm convinced that when we talked to S.I. Newhouse in 2001 or 2002, we wouldn't have had Style.com, we would've had this powerhouse called Vogue.com, and we wouldn't have had Epicurious.com, we would've had Gourmet and Bon Appetit. The critical mistake was not embracing the internet quick enough while other companies just passed us by.
I remember very specifically being the publisher of Teen Vogue in 2013 and watching this little startup in Brooklyn called Bustle launch out of a brownstone with seven people, as the tech bro internet story typically goes. I was banging my fist on the desk going, “How are we allowing this little thing called Bustle to happen?" The amount of unique users, the engagement, the advertiser demand, all within two years, was just epic. It was an interesting time. We got really big on social first. If you think about influencers, we were on Instagram first. We were on Snap first. We were on Facebook first as publishers. Publishers and editors are the original influencers. It was just a different form. It was ink on paper instead of a screen.
Conor Begley: I've never heard that take before, but it makes a lot of sense because if you think about it today, you think about NewYorkTimes.com, these have become very large digital assets. At the same time, it's very difficult to look at something that's making all of your revenue and to take out a piece of that. They also wouldn't have known how to monetize it, right? It's like, “Okay, I put it online, now people can access it for free, but I can't charge one-tenth what I was charging for the print publication.”
Jason Wagenheim: Yeah, it was so wild west. When the iPad came out in 2009, we were charging advertisers $300k to be included in a PDF version of the magazine that you could read on the iPad, because that's all we really had to sell. We thought that would be super interesting. We had no scale, we had no context. We didn't even know if readers were interested in reading a PDF of Vanity Fair on the iPad, but that's all we had to sell. Condé Nast and the legacy publishers could not accelerate digital growth as quickly as print was declining. They spent years righting the ship, and now they're caught up. They're savvy digital businesses now. They're doing great in a lot of places, but it took longer unfortunately.
Jason Wagenheim on Why Empathy is Key to Being a Successful Leader
Conor Begley: You spent a lot of time in this CRO role, and a big portion of that is overseeing sales. I think one of the more difficult transitions for people is to go from a really successful salesperson to successful sales leader. It’s just a very different skill set. What do you think are the ingredients that make a successful CRO?
Jason Wagenheim: It's a great question, because I've seen so many great sellers fail as managers. The story typically goes like this: killer seller crushed their numbers, got the salesperson of the year trophy and a big bonus because they were up a hundred percent, they crushed it. You don't want to lose that person. That person wants to climb and they have every right to want to climb. You make them a manager, you make them a VP, you make them an SVP, because you're afraid to lose them and you're afraid to lose that magic that they brought as an individual contributor.
When you are an individual contributor, you are CEO of yourlist.com. You're just running your business and you have hundreds of people. When you're the boss, when you're a CRO or VP or you're running a team, you have to put everything aside and solve everybody else's problems. You have to be empathetic and you have to understand everybody's point of view. I think that’s a human quality that maybe is something you're born with—it's hard to learn. When you're an empathetic leader, when you can lead from behind, when you don't have to be the hero and you can let other people do that, and really put your ego aside, that's the difference that makes a successful leader.
That sort of empathy or compassion for the way others view the world is a difference-maker in whether you're going to be successful or not. I've unfortunately had some situations where I've lost some really good people because they didn't get that and they couldn't see the world through a manager's eyes. They can only see it through me, me, me. That's the fundamental difference.
There's a great book called The First 90 Days by Michael Watkins. I ask a lot of my leaders to read it because somebody asked me to read it 15 years ago. The most important thing when you come into an organization for the first 30 days is to shut up and just listen and observe and not come in with opinions. Understand who your allies and enemies are. Look for the pitfalls in the company. Really just be a student and find some wins. A win doesn't have to be a big win on a deal. It could be that you literally helped somebody get a meeting, or you took something off their plate to make their day a little lighter. I really subscribe to that theory of listen, learn, understand the environment, and then attack and pick your spots where you're going to try and make some impact. I think the most successful leaders and people that transition are just really great observers and students, and they can pick their spots accordingly once they understand the lay of the land.
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