Amy O’Leary of Upworthy Extended Interview

In Lead by Change New York One, Jeff visits with Amy O’Leary Editorial Director of Upworthy and talks about the art of the story.

Share this Interview

The Interview:

Jeff Martin: I’m on my way to meet with Amy O’Leary of Upworthy. We’re meeting at the Grind Coworking Space on the West Side.
I’m really excited to talk to Amy. She’s doing something unique where she’s blended technology and storytelling. Early in Amy’s career, she was working with a software company, early days of mobile technology, studying at Salt Institute, working with Ira Glass, New York Times, and now she’s bringing it altogether to tell stories at Upworthy that combine tech and storytelling.

Jeff Martin: Thank you for meeting with me today. There’s been a lot of questions I’ve had for a long time, and I’ve gone to you for a lot of questions throughout the years because I think you’re the master of the story. I want to talk to you today because our audience are a lot of tech leaders, tech professionals, tech executives, and also CEOs of tech firms, and so, I wanted to sit down with you and learn a little bit more about storytelling.
Going back where we actually first met, I think it was about 15 years ago.

Amy O’Leary: Uh-huh.

Jeff Martin: A little startup called Gearworks where you were doing kind of mobile technology, how did you see your role at the time?

Amy O’Leary: I mean like any startup, we all had a million jobs, we wore a million hats, but I think you’re right. I think in the different roles I had at that startup over its 4-year trajectory that I was with the company, my job was really I was the one communicator at the company, in a company full of product people and engineers. And so my job was to go around and really listen to everyone and ask them questions about what they were building, ask them questions about their interactions with our customers. Ask our CEO and CTO questions about their interactions with investors. Then my job was really to synthesize all of that into easy-to-tell, easy-to-understand stories that will communicate what this company was doing, which was a crazy thing. We were building mobile technology at the turn of the millennium, which almost no one was doing. You really had to put some craft and effort in how you talked about the stories in such a newly emerging market.

Jeff Martin: So you transitioned out of tech-

Amy O’Leary: Yes.

Jeff Martin: From Gearworks, you went to Salt Institute. You said documentary. Is that right, radio documentary?

Amy O’Leary: Yeah. My ambition had always been to be in journalism in some form, and what I love working at a startup, I kind of knew that my real skill set was probably closer to storytelling than journalism. I made the decision to go, do a graduate program because my real dream was to work at This American Life, and so I did a program that taught me how to do interviews and how to find stories and how to be responsible about them, which is what you were in a documentary program. That’s really served me than through the rest of my career.

Jeff Martin: Yeah. If I remember actually back at that time when you were trying to get interned at This American Life, I believe you told me that you listened to their stories, and you figured out the formula –

Amy O’Leary: Sure.

Jeff Martin: And used that to apply to the role, which you ended up working there as an intern. Is that correct?

Amy O’Leary: Yeah. I’m a big believer that a lot of things that people think are talent are really skills that you can build and storytelling is no different, so if you look at someone like, “Man! They’re telling an amazing story! How can I ever learn to do that?” I’m a big believer that you can analyze stories, break them down, and then what was really wonderful about This American Life is they’re very good at taking lots of different stories and placing them into a simple but highly effective structure that makes almost anything you say utterly compelling.
If there is one superpower in the world that I believe in, it’s that, telling a compelling story. So I really wanted to work with them to understand that superpower, which I was able to work with them as an intern and then later as a fulltime staff producer.

Jeff Martin: What’s it like working with Ira Glass?

Amy O’Leary: Ira Glass is an amazing mentor. I mean I don’t know how he does it. He’s one of the hardest working people I’ve ever had the pleasure to work with, so he’s there all the time. What we did that was so remarkable was that even if you’re an intern, a kid showing up at a show, he will spend all this time just with you working on storytelling exercises to teach you his methods. He would give you a story that had been recorded 30 years ago and ask you to edit it. He had you know probably 50 interns edit the same story, so the minute you showed him your version, it was like a Rorschach test. He immediately knew you were maybe more emotional or you put that bit first and that meant something about who you were, so he really used a concentrated training program to build storytellers in his mold. So that his entire show, I mean he’s launched a generation of storytellers who know how to use his techniques, which was just an incredible experience.

Jeff Martin: What was one of the most impactful things that you learned by working with Ira?

Amy O’Leary: The biggest aha moment I had working in This American Life really had to do with understanding that you can take almost any story no matter how boring and make it much more interesting just by changing the structure. So there’s a little example I like to give, which was in one of the show’s episodes, and I can show you how this pretty boring story becomes utterly compelling.
So there’s a guy named Joe and he’s standing on the subway platform waiting for his train. He looks down at the end of the platform and he sees this shadowy figure, and the shadowy figure comes closer. He starts to get a little nervous and soon this person is going up to other people on the subway platform one at a time. He notices that this person is leaning in and whispering something. Now Joe can’t hear what it is, but as the person gets closer and closer, he realizes, “Oh, it’s like a homeless person. Maybe he’s even a little bit crazy.” But he still can’t make out what they’re saying.
Soon enough, he comes close enough and he could hear it. The homeless person leans in and says, “You, you can stay.” He goes up to the next person and says, “You, you got to get out of here. You got to go.”
Now they’re about to come up to Joe and he starts to feel this tension, this anxiety. Joe starts feeling like, “Wait! I really want him to tell me I can stay. I don’t want to be rejected from the subway platform.” And sure enough, the homeless person comes up to Joe and leans in and says, “You, you can stay.” This wave of relief comes over Joe.
It goes to show that there is just something about the judgment of strangers that it’s actually more powerful than our friends like it’s why the clerk at the bookstore when they look when they look at what you buy, their judgment means more to you than it might if your friend is like, “Why are you reading that book?” So that’s the story.
Now that is a very boring story. That is I could tell that story. A homeless man is going up to different people on the platform and tell some they can stay, and some they can go, tells this guy, Joe, he can stay. That’s a terrible story.
But if you can sequence it right and you keep something offstage and you kind of let the story evolve naturally, that’s one way you keep people’s attention. But the second most important thing is that little bit at the end and this is where all messaging, all stories have their true power. When I say there is just something about the judgment of strangers, that’s the moral of the story. You know we’ll carry that story with you and the moral and the message because there was this interesting narrative that you followed.
So learning that you can almost take any dry sequence of events and put them in that format with a sequence and a moral to make it stick was the best thing I’ve learned in my entire career.

Jeff Martin: From This American Life, you went to New York Times?

Amy O’Leary: So I was hired at the New York Times actually in 2007 as their first ever audio producer. Now that was this little window in time where everybody thought the future of journalism was going to be this really awkward thing called an audio slide show. But I was really glad I got in the door there because I actually had seven different jobs in 7 years.

Jeff Martin: Wow.
Amy O’Leary: I was everything from a traditional reporter to a news editor. I worked a lot on digital change because it was clear to me with my background having worked at a tech startup, being one of the few journalists at the New York Times who knew how to talk to engineers. Now there were some pretty significant things that we were falling behind on. I cared very deeply, I still do, about the institution of New York Times. I think it’s really important for society. I wanted to do what I could to help the paper make its transition towards a fully digital era, so that was a lot of what I worked on. And it’s exciting to be able to reach millions of people with the day’s most important is a hugely rewarding thing to do.

Jeff Martin: Yeah. How do you get a company like that to change? How do you drive change within a company that old, big?

Amy O’Leary: It’s hugely difficult. I mean the New York Times has been around under its current family leadership for over 150 years. It’s an Industrial Era company where it’s got you printing plants and trucks and machines and transition that to a digital company is a really huge undertaking, so a lot of things we tried and some worked and some didn’t. Trainings don’t work. I’m a big believer that you don’t train just to be digital. I don’t think that memos from the top saying, “We got to innovate now,” ever actually do anything to help people.
The most transformative thing in all the years I worked there that I was a part of was this really interesting report. Oddly enough, the most transformative thing that we did was a 100-page printed copy report. But what happened was they realized that the New York Times needed kind of a jolt, and so they asked about eight of us to spend 6 months in a back conference room and really study the paper. We used all of our journalistic training. We did over 300 interviews with leaders inside and outside the New York Times. We did interviews with the readers and customers. We watched them as they used their mobile devices. We did a deep, deep dive into how the paper was working in people’s lives today and how it could be improved.

The end result was again, a 100-page report where we talked abut some of the key blocks, cultural blocks, institutional blocks, organizational blocks, and we talked about solutions, the things that we felt we can learn from other companies, other industries to make the paper a thriving modern digital concern.
This report was originally intended just for six people and that was probably its fatal flaw, if there was one, because it was very well researched and it was a story well told. But what happened was after we delivered this report to the top brass, you know it was meant to be confidential but there was a leadership shakeup at the Times around that time. The day after our current editor had been let go, the full report was leaked actually to BuzzFeed, and so there was a grainy Xerox copy of this 6-month report that was now on the Internet for everyone to read. It’s been downloaded well over 1 million times

Jeff Martin: Wow!

Amy O’Leary: And it’s been called the Key Documents of Journalism’s Digital Age.
Jeff Martin: Fantastic.
Amy O’Leary: We got in the months after the report came out, we got calls from newspapers all over the world. We got calls from institutions like museums and libraries and kind of any true legacy institution that dealt with information was now looking to this report as the blueprint for the changes that needed to be made, which is a fascinating outcome that we didn’t expect. I’m frequently asked to talk about it and talk about that process of change, but if I were going to leave you with one main point for why this worked in a way that no other effort worked was that that 100-page report was a well-told story. When the entire newsroom, the entire company, was able to read it at the same time everyone got on the same page. All the resistance to change melted away because everyone could read in the story. “Yeah, if we don’t make this three to five changes, we probably won’t survive.”
Because the story captivated people, because it was clear, because it was well-told, and because we all shared it in this one unique moment, it was hugely transformative for the company. The year that followed, I’ve never seen more change take place more quickly than any other time in the New York Times. I’m really like even though I no longer work at the New York Times, I’m excited and proud by all the work they’ve done since because they’ve really have taken all those recommendations to heart and they swore with it. They now have over 1 million digital-only subscribers, which is a world that the Times couldn’t have imagined just 5 years ago.

Jeff Martin: Yeah.
From the New York Times, you now have moved on to Upworthy?

Amy O’Leary: Uh-huh.

Jeff Martin: And it seems like such a great place for you to be. You’re such a great person for Upworthy, melding the technology that you understand the technology world, the storytelling world, and bringing that altogether. What makes Upworthy different than the other digital online media companies?

Amy O’Leary: Yeah, Upworthy is really unusual. When I first started talking to them, I wasn’t actually planning to leave the New York Times. I was expecting to have a long and thriving career there, but something really got me about Upworthy, which is that – and you would know this just by looking at our website – Upworthy is the most data-driven storytelling company you can possibly find. Under the hood, we collect more data about how our stories work, if they’re effective, if they work on changing people’s minds, attitudes, and perceptions. And so it’s kind of –

Jeff Martin: How do you collect that data?

Amy O’Leary: Well, we do a couple of things. I mean we certainly watch every possible signal indicator from our online readership. I have a weekly meeting as kind of the lead editor at Upworthy where we look at up to eight different data factors for every single story we publish that week and we analyze what happened with it. But we also have a social psychologist Ph.D. on staff, and we run surveys. So we might tell a certain story and then ask people what their attitudes were about something before or after they saw the story so we can actually see if the story has changed people’s minds or opinions because we’re really interested in not just telling great stories but being effective with it. I think that if you look at most traditional journalism organizations, they would tell true and accurate stories, which is an important and noble mission. Upworthy is interested in something bigger. We have a mission, which is to tell stories for a better world. We ask ourselves with every story if a million people saw this would the world be a better place? We don’t publish as many stories as most other places, but the stories we do publish are finely crafted from story selection to creation to editing to be as powerful, impactful, and to reach as many people as possible. I don’t know anywhere else where storytelling and data are merged in a single pursuit.
I think the challenge for Upworthy, really any media company traditional or digital, is the same right now. The ecosystem, the digital ecosystem for me the company is changing so fast that every 3 to 6 months, you have to change your strategy to match it. I think really what we’re dealing with as an industry is disruption of traditional broadcasting print advertising, so figuring out how to monetize media companies in the digital space is the constant challenge. But because that is moving so rapidly with the rise of video, the growth of – there’s sort of the theory that all digital media companies will eventually be like the cable companies of the future. And so people are trying to figure out how to leverage all the expertise the digital media companies have grown in the last decade towards a space that is becoming increasingly not just a disruptor but a displacer some of the more traditional media channels.
It’s an interesting time, but things are very fast-moving, and like that’s a huge challenge for anybody let alone Upworthy who is a relative newcomer. We’re about 4 years old. We’re still very much a startup and we’re thriving and growing at an incredible rate especially in terms of our video right now. But things can change in the environment very quickly and you always have to be ready for that.
I believe very strongly that there are some fundamentals that never change. I think high-quality original storytelling is one of those things in the media business that is never going to go away. If you got something people crave, that they want, that they can’t get anywhere else, that’s your beachhead, so that was a big part of why I was brought into Upworthy to help establish that for the company whose history has mostly been curating other people’s work, so that’s the first thing.
I think the other thing is just the nimbleness. You have to have an awareness of the market. You have to be able to pivot when needed, and you have to have an agile-enough team that can accomplish multiple objectives at the same time. All those good classic startup things married with a real commitment to strong quality storytelling.
Jeff Martin: From the perspective of tech leaders, CEOs, and founders of emerging tech companies-

Amy O’Leary: Uh-huh.

Jeff Martin: These people need to tell stories, right?

Amy O’Leary: Yeah.

Jeff Martin: They may be telling different stories but they all need to tell stories. What is the one thing that most of those people get wrong when telling a story?
Amy O’Leary: I think it’s a great question because I get really impatient with bad storytelling. I see it from technology and business all the time, and the main problem is that I think most leaders, they know what their marketing materials say, they know what their company’s messaging is, and they kind of stick to that script. Unfortunately most marketing is meant to be completely positive, completely what I would say anodyne, stripped of any –

Jeff Martin: Vanilla, right?

Amy O’Leary: Yeah, vanilla like who’s interested in that like we all have seen enough stories and enough marketing messages to know like boring, turn it off, that’s not authentic. To break through, what you need to do is you need to find a real story of a real person, so whether if you’re recruiting a star you want to bring into your team, you need to tell them that somebody else at your company, you know, “We have this guy named Gerry, and he came in one day…” Tell them the story of Gerry and how he thrived at your company. If you are talking to customers or consumers, you need to tell them the story of another customer, another consumer, and you got to add those little details that actually have nothing to do with your product.
A good example is if I’m talking about a little kid. I’m talking about this little kid named Billy. I could talk about Billy just as the kid is going to use this new app, or I could tell you that Billy has got alligator tennis shoes. He calls his dogs stuffy head, and he hates green peas. Now you care a little bit more about Billy because you can imagine he’s a fully rounded character. Including details and including people not just including marketing messages is a big part of how you break through to use the human brain’s natural information structure, which is hardwired for stories, to kind of use that system to get your message across to tell the story. The moral is your marketing message rather than making your whole bit the marketing message.

Jeff Martin: How does an executive find a story like –

Amy O’Leary: Well-

Jeff Martin: Like you know they’re doing their job.
Amy O’Leary: Yeah, sure.

Jeff Martin: They’re making sure the servers are running and that the implementation is going well.

Amy O’Leary: Right.

Jeff Martin: You know where do they go to find their stories?
Amy O’Leary: I mean there’s two ways. One, great stories should be running across any executive’s desk. If you want to know how things are going, you know from your salespeople in the field, they should be telling you how things are going. Part of that is just having a radar and an alertness to the stories that exist within your company already, and know which ones to grab and hang on to for a presentation or for an interview.
But the other is really listening. I would encourage you know if a busy executive doesn’t have time to do that listening, which they seem generally don’t, it’s a great thing to send somebody out to do, to go on listening toward, to take notes, to record interviews with people inside and outside your company and to sift those back. I mean I’ve done consulting for companies where I’ve gone in and interviewed employees and customers, and then edited those stories down to be like beautifully told versions of what’s happening within their company. There are a lot of ways to do it but it really does start with listening. They’re not going to land on your desk neatly wrapped up in a bow. You got to go out and look for them.

Jeff Martin: Excellent. So the art of storytelling, the pattern is, what is it again?

Amy O’Leary: You want to have a sequence of events, and then an idea about what that means or moral of the story. Really, the big secret here is if you can take any story and make it vastly more interesting by putting a little bit of thought behind how you’re presenting it to your audience and what that moral is.

Jeff Martin: So today, what is the moral of the story?

Amy O’Leary: I think today’s moral is the storytelling is one of the most hugely powerful tools we have to communicate with each other. We can change people’s minds. We can explain who we are. We can connect with people, and we’re much more effective when we do that through a traditional story than when we do it through just saying, “Hi! My name is Amy, and I’m the editorial director of Upworthy.”

Share this Interview

Comments are closed.