Dan Morrell: Hi, this is Dan Morrell, host of Skydeck. When Jen Wong (MBA 2004) joined Reddit as COO in 2018, the user-generated content site wasn’t exactly a burning building...but it might have been smoldering just a bit. Cofounded by Steve Huffman and Alexis Ohanian in 2005, Reddit had seen its share of CEO turnover as it grappled with questions about how to moderate content and build a sustainable advertising model without crushing the site’s notoriously independent spirit. Luckily, Wong had experience working at companies in transition, including AOL, PopSugar, and Time, Inc. In the six years since she joined the company, Reddit’s balanced approach has paid off. Today more than 82 million users come to the site daily for advice and community on everything from 3-D printing to astrology to buying a car. Revenues have grown from $100 million to $800 million, and the company went public in March 2024 at a valuation of $6.5 billion. In this special edition of Skydeck Live, recorded at spring reunions, Wong sits down with classmate and FOMO Sapiens podcast host Patrick McGinnis to talk about her journey at Reddit with the candor and clear-sightedness that have characterized her career as a leader in the world of media.

Jen Wong and Patrick McGinnis (photo by Stu Rosner)

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Patrick McGinnis: So it’s been an incredible year for Reddit and for you. Let’s go back to 2018 when you, a rising star in the media world, with a great perch at Time, join Reddit as COO. And it was not a clear … the company was at a different place at that time. Let’s start with how the opportunity came to you.

Jen Wong: So I was actually not working at the time because we had sold Time Inc. And I was taking some time off, which means I was doing a renovation. Every time I take time off, I end up renovating and that’s why my wife is like, you need a job. So I did not get the call for the job. This is the first time I actually got a role through a recruiter. There was a recruiter on the role, and I didn’t get the call partially because I didn’t live in San Francisco. So Reddit is headquartered in San Francisco. I live in New York. I’m a diehard New Yorker. But a friend got the call and he said, it’s not right for me, but I think you should call Jen. I think she’d be right for it. And so that’s how I ended up with the opportunity, was the grace of a friend.

And I often say, if it’s not right for you, take the call from the recruiter, pass it on. I think that’s a really good thing. I had always known how awesome Reddit was. I mean, it had grown over the years. I’d watched the traffic grow. And if you work in the world of consumer media, you know how important Reddit is because it’s where all your editors are finding ideas. It’s where they get their memes for the social handle. It’s where they do quick surveys. It’s when they see trends, like cultural trends, really early and then write about them. They’re all on Reddit. And so I knew how important Reddit was, and I had been a Reddit user as well. So I was pretty excited because I knew how big it was and I’d seen that Steve [Huffman] and Alexis [Ohanian] had gone back to try to sort of right the ship.

So I met Steve at SFO, I think at like 6:00 AM. We were sort of ships passing and had a great meeting and I got really excited because it’s really rare that you get to work on an asset that is, I think, a pillar of the internet and has such a big audience. It was hard to get that large an audience even then, and that was six years ago, but that has no business model—where it’s a really open canvas where it has to become a business and that’s going to be your remit. That’s really, really fun. So I felt really lucky and excited, but I knew that I would have to go back and forth. The hardest part was sort of convincing, I had to convince Steve that I was not going to move. And I said, well, maybe I’ll move at some point, but if it turns out that we want to have an advertising business, I think you’ll be happy that I’m in New York. And that’s worked out. I did not manipulate our business model so I can stay in New York.

PM: Now you joined at a time when Reddit is going through changes. It had just had a management change. The CEO had exited, the founders came back. There had been, obviously this is a very active user base, so there had been some upheaval a little bit in the user base. And you are coming in with this mandate, which is I need to grow revenue. And that’s going to be through advertising and that is a trust-based business. You’re getting big brands and small brands to come on to your platform and put their content alongside a lot of UGC, user-generated content. And that was at the time, when you came, that was the big challenge that was in front of you. Obviously, there are risks, there are opportunities, but what was your personal calculus as you thought through the opportunity?

JW: Professionally, it actually didn’t feel like a big risk because it was already a little bit in crisis and in cleanup mode. So, I didn’t do that. The best I could do was help it and make it better. The bet was that there would be personal and professional upside that we could fix it. It was the opportunity cost of doing something else. It was that bet on whether we could do it and I could be a part of it. I didn’t worry about the downside risk. And I had done this twice. I have a pretty optimistic personality, which has led me to do two turnarounds, like AOL and Time Inc. I think were both seriously disrupted businesses, public company environment, it’s like running a little bit into at least a smoldering building, and I was okay with it.

So that was kind of how I thought about the personal calculus. But then at the same time, it’s like it’s Reddit, it’s a pillar of the internet. It’s been around since 2005. It has so many users, it had no monetization model. People still love it despite the protests and everything. They still come to it every day. To me, it was really obvious, this is a great asset, I’m going to do it. The other part that was part of the personal calculus is I lived in New York and I had a new baby who was less than one, and that was part of the personal calculus, is I was going to have to get on a plane all the time. But again, that was a bet that I think I took professionally and personally that paid out well. Reddit I think is, if you don’t know the mission for Reddit is community, belonging, empowerment for everyone.

I give that context because I think we’re a very mission-driven company, and I think that shaped a lot of how we thought about the business. So, because Reddit is so vast and because one of the principles is that we empower users, we could have had, and I think will have, many business models, so we believe that users can go beyond conversation and transact between each other. They do that today. They’ll ask for somebody to Photoshop a photo and tip them $5 with very informal mechanisms. We didn’t quite think about data licensing—that’s a business now, which we’ll talk about later. And then we thought about advertising, and we ended up starting out with advertising because it keeps Reddit free and open. So we do not force login. If you end up on Reddit through Google searches, you notice we don’t block you from the information because we believe in the open internet and allowing people to get the information that they need.

Now, if you log in, it’s great. You get a first-class experience, it’s personalized. So we love that. We want you to log in, but we don’t prevent you from getting the information you need. So first principle was, okay, we want Reddit to be free and open, and ads allow us to do that. The second was that our community has very strong values and we as a company had—these were not, I think, clearly articulated at the time—but we really believe privacy is a right. Users on Reddit are anonymous. We don’t target based on your demographic profile or tracking you all around the internet. We think that violates our user privacy. We don’t sell user data, et cetera. So we have these privacy principles and community values. And so when we crafted the ad business, we wanted a business that was in harmony with the community and the values.

That’s really important because the community has a big say in what we do. They’re equal stakeholders in Reddit, the platform. The targeting on Reddit is all first party. We don’t track you off property. People can delete their data, they can do anonymous browsing, which means that we don’t collect the data. We obviously use that data for advertising purposes, but we don’t reveal any PII [Personal Identifiable Information]. So all those principles still apply. And then when we decided to build the advertising business, we also thought about, okay, well what part of it? So there’s brand, there’s sort of mid-funnel where you drive traffic, and then there’s performance. And we work across all those funnels, but we’re very focused on performance because performance is, if a customer doesn’t purchase, then we basically don’t have a business. And I think that really aligns user interests. So the ads have to be good enough that they like them, they’re personalized, they’re relevant, they’re good, and they perform. And if we can align on performance, I think that allows us to make sure that the ads are not disruptive, but they’re logical and make sense. So that was another piece that we thought about in crafting the ad business, and that’s the journey we’re on.

PM: So you’ve taken revenue from a hundred million when you joined up to 800 million now. 98 percent of that is advertising. That’s pretty incredible first of all. But I imagine—you know how things are: Getting people to try new things and change behavior, especially when they are entrenched or organizations that are risk-averse, is not easy. And especially when you are part of a company that has a huge user base, but obviously is retelling its story. As you think about that trajectory from 2018 till today, what were the big things that you learned or what were the big hills that you had to climb and how did you do it?

JW: It’s a good question because we had a big protest in 2015, which was very, very public. Our communities went dark. And I think that for an advertiser is pretty odd to see, have people protest. We had one last summer too. It’s fine. You can protest on Reddit, but not all the time. But the first part was, I feel like the first year and a half was almost like an apology tour, frankly, just, recognizing that we had had a windy path and not done everything we should have done in some of those years before I was there, before Steve and Alexis came back. But we were not good about content moderation policy, which is really important. You can only have community and belonging if you have safety and you have context and you have a well-moderated space, you need a clean space for that.

Steve had done a good job when he came back in 2015, just really spending time on moderation, safety, and policy. And I think that bedrock had been reset, but it took a while for the market to understand that. So a lot was education about how we do layered moderation with layers of rules and human moderators and voting, which is very, very different than other platforms. A lot was education and acknowledgement of that. And that took probably a year to two. We still worked through that, but really almost a couple of years to lay that new foundation of trust. And then the other part was just proving it, was having Reddit be safe through election cycles, which were pretty tumultuous, through lots of events in the world, through Covid, through just a lot of world events. And I think we did a relatively good job. Reddit was safe. Reddit had civil conversation. We didn’t have a lot of the issues that I think peer platforms had, and I think that’s been recognized in research by regulatory folks as well. So we felt really proud of that, and I think that was the real proof that we had a safe environment and we’re really a different company.

PM: It’s interesting, I think about this. We’re talking about the users so much, and I love Reddit. I go on all the time. It solves problems for me. Like how long should I put my chicken in the air fryer? Thank you, Reddit. But I think about one of the things that we learned here at the Harvard Business School is how as managers, you have to walk the floor, you have to be connected. And I know that’s deeply central to your ethos, but how do you actually make sure that you’re always learning from the community, that you’re always up to date with what’s going on within it?

JW: Yeah, we spend a lot of time, and we have a team that spends all their time talking to the community, and we actually get the mods together in different cities. They’re all over the world. So they have a community within themselves of helping each other mod, which is pretty amazing. The other thing we do, and I enjoy this, I sort of guest-mod every year, a lot of our execs do this for a week. You do an adopt-an-admin and you become a mod in a community and you’re clearing the queue and you’re chatting during the day and figuring out the kind of content that’s coming in that’s appropriate and not appropriate. And that keeps it real in terms of how well we’re doing, in terms of our tool set, and what their experience is.

PM: Obviously a lot going on there that’s going to change the world. As somebody who thinks differently and has been able to see so much of the internet and in the inside from this really interesting perch, what are the big things you think about when you think about where the internet is going?

JW: My day job is thinking about online communities, but just this issue and question around communities I think is pervasive. It’s everywhere. I read The Life and Death of American Cities, and that was about changes in city communities, and I’m reading Anxious Generation now, which is about the demise of real-life communities in everything from religion to scouting, et cetera, that has made Gen-Z generations very anxious. So I think about communities a lot, and I think it’s reflected both online and in real life. And I definitely worry about them. I have two young children, so I think a lot about, okay, how do we make sure that Reddit does a good job of always reflecting the natural parts of human behavior in being an online community? Not ever creating interactions that are unnatural, which I do think that there are platforms that have created unnatural behaviors, and there are deleterious effects from that.

PM: You’re saying people don’t poke each other in real life?

JW: [Laughs] Yeah. So some of the behaviors I think that are fostered are unnatural. So I think about that a lot. And then I think in reading and just living in real life, I think about what are those actions that you want to preserve that build community? And I spend a lot of time thinking about, gosh, what will happen with my kids and what will their communities look like both online and offline, and how much will be online versus offline, and what will they look like?

PM: I want to thank people for acknowledging my deep cut Facebook reference there with the poking. [Laughter] Thank you so much. Alright. So shall we go to some questions from the audience?

Sam Clemens (MBA 2004): So question for Jen. It seems like discussion in society, maybe internet more broadly, just seems very polarized, very broken at the moment. Thinking about geopolitical discourse. In contrast, the one place where discussion seems to be working really well is Reddit. What guidelines might you suggest on how to like…can we fix discussion on the internet?

JW: I think so. I think Reddit does a good job with discussion, but I think it’s possible to just generally have better quality conversation online. At Reddit, everything we build is trying to mimic real life. So nothing unnatural, right? So if you think about how do you have a good discussion in real life, it’s usually knowing the context. So it’s like, okay, somebody’s hosting the dinner party. Okay, is it work colleagues? Is it college friends? Is it my sports buddies? Who is it? So you know the context, and that’s true, we have communities to provide the context, but you can provide that however you want. The second is rules of engagement. You know how to show up at your work event versus with your drinking buddies or with your college friends. You know how to show up. You know what to wear, you know what to say, not to say. Those are the rules. That’s important for keeping the space safe and having a sense of culture to it. Like, Hey, I’m a part of this group. We’re inside. There’s a certain set of mores and culture. And the third is that everybody can say, like, Hey, that person’s being an ass(beep) tonight and they gotta go. I’m not having fun anymore. And you have to be able to do that and say, you’re outside the bounds, this community or this group of behaviors because it’s not fun for everybody. You’re ruining it for everybody. So you gotta go. Those principles apply in real life. You can do that online, too. It’s just that I think a lot of the dynamics of what’s been built today optimize for not that. Maybe optimized for engagement, maybe optimized for monetization, or optimized for other things.

PM: In the back? Yeah.

Alicia Omans (MBA 2019): Hope you don’t mind a question more on the personal side, but as you look back over your career pre and post-HBS, what is your thesis behind how to be successful?

JW: I’ll tell you what I think has worked for me. And I often say I’m happy and I’m grateful because I’m exactly where I want to be, which was not always true in my career. There were moments where I woke up and said, this is totally not where I want to be, and I need to hit the reset button. The good news is you can do that pretty successfully and generally move the arc in the right direction and land in the right place. That’s definitely one thing I’ve learned. For a long time people always say, Do what you love. I’m like, what does that mean? That seems so trite. What exactly does that mean? I think I do what I love in that, so if I were to rewind to when I was younger, I was an only child. I spent a lot of time alone and I spent a lot of time alone watching TV, listening to music, reading People magazine, and living in pop culture.

It’s something I love. I love how people find information. I love the zeitgeist. I love changes in consumer behavior, disruption. I love all of it. I’m the first one to download the new music on Tuesdays. I’m the first one to download some new crazy app and test it out. I love that. And I think it makes me better at my job. I’ve generally worked in consumer businesses because I’m the first one there, and I’ve gained, I think, personal intuition about how these environments kind of play out. And now that’s my job. Day-to-day. I build a business around it, but I get to think about and live in that world every day. I believe that taking something that I have loved since I was little and merging that with what I do every day, I think has helped me be successful and just have a little bit more of an edge because I think about these things all the time for fun. And the merger of those two, I think has been very personally harmonious for me. Just feeling like, wow, I can bring my whole self to work in that sense. And that, yeah, I’m working sort of all the time a little bit, but it’s fun. It doesn’t feel taxing. It’s not an energy suck, it gives me energy.

Skydeck is the Harvard Business School alumni podcast featuring interviews and insights from across the world of business. It’s produced by the External Relations Department at HBS. Our audio engineer is Craig McDonald.

It is available on Apple, Spotify, and wherever you get your favorite podcasts. And if you could take a moment to rate and review us, we’d be grateful.

For more information, or to find archived episodes, visit alumni.hbs.edu/skydeck.

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