COO of Reddit, Jen Wong: Inside the Platform That Shaped the Internet
43m 19s
Jen Wong’s journey from Time Inc. to leading Reddit as COO highlights the power of serendipity, personal values, and deep alignment with a platform’s mission. She joined Reddit in 2018, drawn by its community-first ethos and the opportunity to build a business that respects user privacy and authenticity. Unlike traditional platforms, Reddit scales its business through contextual advertising that leverages users’ real-time interests and community engagement, avoiding intrusive data collection. The platform’s success is rooted in its unique architecture—where each community governs its own rules, fostering safe, passionate, and highly relevant discussions. This culture of openness and trust has made Reddit not only culturally resilient over 21 years but also a critical source of human-generated data for AI development. Through strategic partnerships with major AI firms like OpenAI and Google, Reddit ensures ethical data use while preserving user privacy and control. Founders leverage Reddit for organic growth by adding value to conversations rather than selling products directly. The episode ultimately celebrates Reddit as a living ecosystem of human connection, where authenticity, community, and reinvention are central to both personal and professional success. Jen’s journey underscores that leadership and self-discovery are ongoing processes, not linear achievements, reinforcing the idea that one can continuously evolve and stay inspired throughout life.
- Reddit's like real life. It's like coming to a dinner party or hanging out with friends. - Yeah. - If you showed up in a dinner party and you're like, "I'm just gonna sell you my new product." You're not gonna have a lot of friends. - They're like, "I don't want to talk to you. "I'm trying to enjoy my dinner right now." - Exactly. - You went to Stanford, I went to Harvard, Shree went to, you also went to Harvard, Shree went to Stanford. - It means we're all still paying off debt. - I did not dream of being a business leader. I did not dream of being a technical person. I did not dream of these things. I often tell people that it's very hard to sit down and architect. You're like, "Some people do it successfully." Well, for most people, it's like a journey of discovery and reinvention. We say, "You can reinvent yourself at any time." - I like to think that all the time and that keeps me just excited. - I'm Shree. - I'm Jean. - I'm Jen. - And where are the tiger sisters? - We are your Wall Street and Silicon Valley big sisters. - And we're a top 10 business podcast bringing late night sister talk meets boardroom strategy. When Jen Wong joined Reddit at COO in 2018, it was already one of the most influential corners of the internet. The challenge wasn't building the community. It was building the business. Over the next several years, Jen scaled Reddit from the front page of the internet to a public company. She scaled its advertising business, secured major AI data licensing deals and helped lead the company through its 2024 IPO. She's had a front row seat to some of the biggest questions shaping the internet today. Free speech, community trust, AI, advertising, and what happens when a platform built on authenticity now has shareholders. Today, we are sitting down with Jen at Can Lions in Can France to take you on an inside conversation into one of the companies that has consistently shaped culture, conversations, and communities. And it's helped build a global forum for people to feel less alone in this world. Jen, welcome to Tiger Sisters. - Thank you. Thank you, thank you for having me. We're so excited to have this conversation. And can we also say, hello, we're in Can Lions in France. - Pretty great. - Crazy room. - In the Reddit daily. - Guys, if you're not watching this right now, turn on your video and look at this amazing set that we're in, you can't see what we see, but we're in a bubble right now. And people can see that we're having this conversation with Jen, it's pretty epic. - Yeah, it's pretty fun. - Okay, Jen. So let's go back to 2018. When Reddit was a private company and relatively under the radar compared to its internet company counterparts, you were the COO and president of digital at Time Inc. So you were a pretty big deal. A lot of our audiences in the stage were thinking about their next career steps. What was it that convinced you to leave Time Inc. and join a COO of Reddit? - You know, eight years ago, that was a pretty easy decision, but I was not actually on the original call list or the recruitment. - Say more. - So I lived in New York and I live in New York. I'm a diehard New Yorker. - Go next. - Born and raised. And Reddit was headquartered in San Francisco. - Yeah. - And the search was for a COO who would be in San Francisco, obviously. And so I did not get the call, actually for that, but they called a friend of mine. And he said, you know, it's not right for me, but I really think you should call Jen. And I'm so grateful for that. - Yeah. - That I met Steve at the Gordon Pierce at the SFO Airport at some ungodly hour as he was passing through and I was passing through. And we hit it off and we had more discussions at the office and I knew it was right for me because when I left Time Inc, there are a couple of things. One, I really wanted to go back to pure growth. And even though Reddit was still a little bit of a turnaround plus growth, I think I really saw the opportunity. It's very rare that you have a pillar of the internet with a very large audience that doesn't have a business. It's just like an open canvas, which is amazing. And the second thing was I had at my time at Time Inc and just working in publishing a pop sugar, I'd watched all my editors go onto Reddit and like look for ideas. All the editors were constantly looking like social media ideas, what's the next trend? Like kind of mining Reddit already. And I'd watched Reddit grow just on its own without a lot of investment, just growing sort of in the advanced portfolio. And so I really believed in the opportunity. I had been a long time user. And even at Time Inc, when Steven Alexis came back, I'd reached out and actually just to know, hey, what's going on in that time? So I was really excited like putting all these things together. It just made sense. And I was on the beach because in January, we had sold Time Inc. And so I was taking Time off because I had a newborn at home and I hadn't had time with them. And so I said I was going to take Time off maybe six, nine months. And when this opportunity came up, I was like, okay, I'm going to do it. I'm sort of cutting my break short. - So you ended up taking how much time off? - I ended up taking three months off, okay. Instead of my six to nine, and it was worth it. It was the right opportunity for me. Even though I knew I would be on a plane, going back and forth, then a remote leader on the team. I think at the time I was the only remote exec. - And what a good friend of yours? - Yeah, to offer your name up to be like, Jen would be perfect for this role. - Incredible. And that's why I often tell people, take the phone call from a recruiter. And even if it isn't right for you, nominate three great people you know for that opportunity. Like you can spread that to other people and make amazing things happen for people. I always tell people that might do that today. - That's such a good recommendation. Okay, my question is, so when you joined Reddit in 2018, was there already the plan and sort of like a pathway to going public? And if so, or even if not, like what were the things that you knew had to change to get there? - It's a great question. I think Reddit always being like a pillar of the internet and so different from everyone else. And so special, I think. We, Stephen, I spoke earlier. We always thought that IPO was the path and that was sort of the context of thinking about the companies to be independent and for Reddit to fulfill its mission independently. So that was the dream, I think. And there was a lot of work to be done there. - And so wait, so you knew that going into taking the journey through the role? - Yeah, that idea that that was going to be, I also think that we wanted to do. - Yeah. It made sense for Reddit. But obviously between getting there, you really needed, we needed a business. And that was less clear what the business would be. There was some advertising at the time. There was also some programmatic advertising. It wasn't all sold by the Salesforce. Not clear what the ad products were. And there was also a little subscription business. And so there was a little bit of a debate of like, which do you do first? Both are probably really viable on Reddit, which do you go after first? And we decided on ads because ads scales with users and it keeps the platform open. And Reddit is just a born of the open internet for people to get information. We don't want any friction for that. So I think the ad model really, I mean, one, it's a great model when it works. And two, I think was really in line, it could be built in harmony with our values. And that was really important because, I think the digital advertising business has gone through these arcs of really collecting a lot of first party data on people for targeting. And we of course have anonymous users. So we thought, okay, well, how do we build a great marketing platform that has great outcomes, but doesn't have that apparatus and is different. And so we built this business that's predicated on context. The environment that you're in, you're reading about whatever it is, vegan spices now, like gosh, what are you interested in? What would be the right ad there? That was based on converting that high, high intent and high signal that people give on Reddit for their interest into action. - Yeah. - And I think that's worked out really well, but we took the bet then. Advertising platforms are really expensive to build. And so if you only do it, if you think you're going to be big and therefore can stomach that investment and that build and we're eight years into this, and we still have a lot more to build, but that was the journey that we decided to take. And I think it was one of the best bets that we did. - Yeah, quick pause. Here's the productivity hack for you, outsource your content curation to us. You can count on us to bring you the well researched ideas, topics and conversations that people are having. To help us keep making this content, subscribe now, wherever you get your podcasts, YouTube, Spotify or Apple podcasts. And we're launching a Tiger Sisters newsletter coming soon. You can sign up in the link in our description. And now back to the show. Okay, so this is a little bit in the weeds, but the context is I also used to work in advertising at Snapchat. I helped build and scale our AR advertising business. So as you were talking, I was like having all these thoughts. I was like, okay, so building advertising business, but the users are all anonymous. So like then how do you like monetize that? But then you're like, oh, it's based on their interest. And we know what they're doing because they're writing about it. So then that's how you create all the like lookalikes or like affinity sort of targeting, right? - That's exactly right. It's based on your activity on Reddit, the context that the conversation you're sitting in, the communities you spend time with. And it doesn't matter that we don't know your gender, age, et cetera, although a lot of that is inferred from- - Sure, okay. - You can probably infer what you're spending time on.
et cetera, et cetera, but that's not important. And what is important and what is special about red is that when you are anonymous, you reveal things that you don't reveal when you're under PIA. So when you're on, when you're under your name, there might be a little bit more posturing, you might be editing, who you are, and you might not be sharing everything. Do my friends care that I'm an avid gardener? They do not. They really don't. Do they care that I went through this long journey and buying my first car at a very late age? I didn't bought a car until I was like, ooh, be something. And that was a tough journey for me that I went through on Reddit, but I didn't go through with friends because I was a little embarrassed to do that. So you reveal things that are more personal to you, which also means you're an incremental customer that somebody can find that you think can't find elsewhere. Yeah, this is like one level deeper because I think the way that I have thought about ads is obviously the demographic information that you have up front, but what I'm hearing you say is that that's not even as valuable as the niche information that we have on people. Maybe they're most like vulnerable questions and vulnerable answers that they're getting on Reddit. Yeah. I think for some things, there might be a correlation. For other things, I think there is none. If you're going through an illness, a lot of conditions are just a human condition, right? It's not about your gender, et cetera. And it doesn't matter who you are. It's just a matter of like wearing the same life circumstance, buying a car is a universal life experience. It doesn't really matter. I mean, in this case, it was pertinent that I was a parent with two kids and I was solving for car seats, but that was pertinent, not my gender. Yeah, I think this is the secret sauce of Reddit and also Gene speaking about her experience at Snapchat. I used to work at LinkedIn on the product side and love my time there. I have a LinkedIner, but there is posturing and there is a professionalism 'cause your name and identity and work history and resume is tied to what you're putting out there. And so, there's a little bit of this going on on LinkedIn. It's very professional. And I would say, and I say this in a loving way, Reddit feels the opposite. In its design, which I think is very clear to me, like the LinkedIn design versus the Reddit design, I think there's something there about how Reddit curates the community where people feel comfortable sharing, obviously with the anonymity that we spoke about, but also something in the design and the forum space where people want to contribute. And even if you're not contributing, you feel like you're gaining a lot of value just in the place that you're in. I think it's architected fundamentally differently. The anonymity I think allows for people to reveal things in a very safe way. And I think what makes Reddit different is the structure of communities. So the communities are, they have different objectives, they have different things that they are trying to do and they help the conversation stay on topic and accomplish whatever it is that the community wants, right? If you're passionate about gardening, if lots of different flavors of gardening, there's vegetables, there's flowers, there's succulents, there's specifically what it is that you are interested in. And the people who come to that, I mean, you can imagine if you come to a succulents community, you are really passionate about succulents or your lens. Really trying to make sure that your plants grow, right? And that's your purpose and that's why you're there. You're not there to talk politics or other things that are off topic. And neither of the moderators are there to have a great conversation about succulents and be helpful on that. And so that makes the quality of the conversation so high. Yeah, because everybody's there for a purpose and they're often very knowledgeable about that subject. So in that way, it's like self-curating. - I'm laughing because Sheree-- - I need that Reddit, I need that Reddit thread about succulents 'cause mine will not stay alive. - Sheree is very into gardening and she's a very successful gardener except for succulents. - Really? - I think they should be the easiest, I think, because they don't have to ignore them. - I cannot, I cannot. I overwater them and they die. My Jane plant is very sad. - All my plants are very, all my succulents are very sad. But yes, I need that. - I'm an avid gardener and I've gone through a huge vegetable gardening journey on Reddit. Lots of success and still some consistent failures. Like carrots will be the death of me. - So that's why it's your go-to example 'cause that's your community. - Yes, I mean, I love it. And I love the gardening UK community. I think UK gardeners are really another echelon of gardening. - Shout out to that community. - So Reddit is often described as the front page of the internet and it can be a place where people find learning, culture and real belonging as we're talking about in these very niche topics that really feel like you belong. I do want to address too. I think there is a perception of Reddit fairly or unfairly that it can be a place for I think lonely people, disaffected people to find community, but not in a great way or promoting anti-social world views and potentially resentment. How do you think those two realities which can exist, I think at the same time? How do you think they reinforce one another? How do they live together? And what is the responsibility of Reddit to shape both sides of that? - I think that's the breadth of the human experience. Honestly, that's the reality. It's like the human experience has all of those things. And I think Reddit has space for all of those feelings and experiences and that's okay. Like the point is to have an open discourse and to maybe have different points of view and opinions and life experiences and reactions to different things. I think that's okay. All within our policies, I keep it safe and civil and open. And that's what's really important for the health of the community. And that's what our community wants. They want that open discourse, but they want that safety and that civility in the conversation. I think we have a system that's very different than everybody else, which is just a set of simple rules that govern policies like, no, hate, harassment and citing violence. These things that you would expect for a universal like safety and comfort on a platform that we enforce. The thing that's really unique about Reddit is that every community has its own rules. - Yeah. - And the moderators and the community designs those rules. And those rules are very specific to the community. And so you have communities that are like, you know what, I just want to be like curly hair. This is a community about positivity about curly hair. And the moderators and the community keeps it really, really positive and celebration of curly hair. Great, that's what they want. And in those spaces, that's the experience you're having. Overwhelmingly, I'd say most communities, which are communities of interest and passions like that are overwhelmingly positive and supportive. There are communities of debate, right? There's communities like change my mind where you're like debating a profound belief or news where the political backdrop is so many things going on. Yes, there's gonna be a lot of debate. And that's okay too, right? Those are different spaces with different vibes. So there's space for all of that on Reddit. I would say that overwhelmingly in my eight years at Reddit, I see kindness and positivity and humanity and people being helpful and supportive. I think it is overwhelmingly positive. But there's no doubt that in our 21 years, we definitely had a period of time where I think we were still applying our policies in a scaled way. And I think during that time, I think the platform did not deliver everything it could in policy and some of that, I think probably lingers in the perception. I think in the last eight years, that's changed pretty dramatically. But yeah, I should acknowledge that there've been different phases of Reddit and somewhere better than others on that front. - And was it like an intentional company goal or objective to change that question? - 100% think it's like the first thing when Steve came back that he focused on. And it was a continued focus when I joined eight years ago for application of policy, safety, relationship with moderators and supporting the moderators, building our community team and a building that foundation of supporting them with tools for both safety and for accomplishing their goals, the foundation of brand safety and our advertising business, all of it, explaining how we do moderation, building those tools, that was absolutely a focus. - I want to talk about another use case that I'm so curious about for Reddit. I went to Stanford's business school and I'm in a WhatsApp group of people in my class who are now founders. And there was this really interesting question that someone posed in this WhatsApp group and they're just like, how are you guys using Reddit as startup founders to promote your product? Whether that product is director consumer, CPG or whether it's like a B2B SaaS, how are you using Reddit as a marketing tool as a startup founder to do product placement to generate conversation, whether organically, or honestly, I don't know if it's paying people to do it, I'm just so interesting, 'cause I hadn't heard of this side of using Reddit to do product placement, I think it makes a lot of sense. But I wonder, how does that work? Is that something that you guys are thinking about? And where does the line, where is the line of like, oh, this is a natural conversation of people who are aligned with the moderator, wanna contribute versus a startup founder going in there plugging their product? - Yeah, I see the general rule on Reddit is to always add value.
to the communities and the conversation. If you remember in the community space, the community has table set the conversation and you are there to add value to it or to add value to whatever it is that the poster was asking for help on or discuss it. And so if you think about founders of, and people building new products, there's a lot of value that you can add. You can provide scientific knowledge. If you're doing research, you can give an opinion on a product, you could do an AMA to show your expertise. You can listen to, you can actually ask questions to people. I'm building this product. You seem to be experts in it. What are the things that you want to see it? So there's a lot that you can get out of communities. I would say advocating for your product, like IE marketing and selling your product is something that is really not successful at scale unless you use the marketing platform. Because many communities, they don't want selling or offers in their community. And it's explicitly in the rules for the community. And if that's, think about Reddit's like real life. If you showed up in a dinner party and you're like, I'm just going to sell you my new product. You're not going to have a lot of friends. They're like, I don't want to talk to you. I'm trying to enjoy my dinner right now. Exactly, versus if you were there and you're like, talking about it and like, whoa, this person's really knowledgeable at this, how did that happen? It's like, oh, that's what I do for a living. And I think about this problem a lot. Wow, OK, that's a really different way to join the conversation. So I always say use human analogs to think about how you show up on Reddit. And if you want to table set the conversation, that's why the marketing platform is there. That's where you get business outcomes at scale and how the community expects you to show up when you are table setting the conversation. I love that. Human analogs for how you show up and read it. It makes a ton of sense. I'm like, people should be thinking about that more. And that's how we build product. That's how we think about the interactions. We want things to happen that reflects real life and what humans want and how they naturally behave. Love it. If you guys enjoyed our recent episode about communication with Professor Matt Abrahams, you should check out his podcast Think Fast Talk Smart. Yes, this was one of my favorite conversations. And Professor Matt Abrahams was my speaking coach when I did my TED Talk last year. We basically manifested this episode because we literally talked about him in an episode the year before. And then now here we are besties with him and recommending his podcast. Check out Think Fast Talk Smart. It's a podcast that comes out twice a week on Mondays and Thursdays. They go over everything about communication and speaking, whether it's presenting, small talk, networking. They cover it all. And communication is such a universal topic. There's something for everyone. So one thing, Jen, that's very interesting to me is that we have seen over the fullness of time many platforms, internet platforms come and go. So we have MySpace, Vine, BeReal, Clubhouse. All of these are in the graveyard, the internet graveyard. Yet, Reddit has still remained culturally relevant and heavily used to this day, even after almost 20 years. So why is it that you think Reddit has won out over time? And is it some magical combination of serving innate human need, plus well-executed business strategy, or is that giving it too much credit? So Reddit is 21 about now, which is pretty wild. And if you think about the arc of Reddit, it's wild to think how much has changed in the secular behavior of people in the background. I mean, Reddit has consistently grown through mobile, like the iPhone, like just a smartphone. The emergence of video, the birth of social, right? I mean, all of these things are profound, secular, changed, now AI. And in all that time, Reddit continued to grow. And I think about that a lot. And I think it's because what Reddit does is so different and unique from what anybody else does. There's just no other place on the internet that is structured around communities. And it has this very scalable model that where the moderation scales with users, and now the business model scales with users. And so I always think, we look at what other people do, but Reddit wins by being Reddit. And over the years, I think there's been a lot of discussion and debate about, wow, gosh, seems like everybody likes this follower model. And look at that viral growth, look at advertising. Seems like it has to be really transacted on identity collection, et cetera. And yet, we've done something different in every case and stuck to who we are, building a business in harmony with our values, user privacy anonymity, and sticking to those dynamics. And I think that has really served us well to be the-- so we really focus on being the best version of Reddit possible, which is we should be the biggest trove of human intelligence. We should have the best conversations about every topic, in every language, on everything on the planet, for every human, and everybody who has a passion and interest to be able to find a home on Reddit. So we focus on that, and less on mirroring, I think, what other people do. And I think that's served us well. Now, we are a consistent grower. We're not a viral grower, in that sense, because we don't have a follower-based model, a dump-your-address book model. And that's OK, because it's this really healthy way of consistently growing, while also maintaining a very high quality content and experience. I think those things are really important in tandem. Yeah. I think one thing that is kind of crazy is that this commitment to remaining a very straightforward product, where you said it was the-- it's almost like the primordial goo of humanism, right? It's like everybody's private thoughts, and deepest musings are put into Reddit, and that has turned into this huge conversation. And that has almost ironically somehow turned into your most valuable product in the age of AI. Now, because AI doesn't know anything, yeah, unless it gets it from humans. It just has no thoughts or opinions on anything. Yeah. And it doesn't-- it didn't even know how to talk, right? If you think about Reddit, Reddit is added value from pre-training to post-training, to grounding, to obviously reference in search. And that's because on Reddit, you learn how people talk to each other, you learn how to stay on topic. You know what's appropriate? You know what new emerging perspectives are, like people's opinions. You learn how people speak, right? The other vernacular changes. And you know what an opinion is on a new product that came out yesterday, because some human had to interact and make a decision whether they liked it or not. All of that is on Reddit. And we build Reddit for our mission of empowering communities and making their knowledge accessible to everyone. We don't build Reddit for that purpose, but it turns out that that is one of the most valuable things, because again, AI doesn't know anything unless humans tell it something. Yeah. I mean, so is it just like the luckiest coincidence in the world? I'm not coincidence, but, like, right? I think-- Market timing, I think, is what you're talking about. It kind of is, like, if you think about the ARK REST, we're 21. The first 10 years of Reddit, we were just a destination with normal word of mouth and sharing. We were not-- we didn't have a corpus that was big enough to be indexed in search or found by anybody. You just found us through people sharing and telling each other, like, you know. And we still are a destination today with that same dynamic. But five to 10 years ago, that's really when our corpus got so big that we were indexed. So now we started to be appreciated by search, and people could find us. And, you know, at the beginning, they would find us on broad-based queries, or just even narrow queries, but not navigating to Reddit specifically. Be like, well, you know, what are the best running shoes? Or, I'm a parent who has this issue, and, like, turns out, the best answer to that question was on Reddit. And then, over the last couple of years, because people have realized that, they now navigate specifically to Reddit. And we're a top 16 search term. So it's, like, best running shoes Reddit. I just am using this tool to get to Reddit as a destination again. And now, the next incarnation of that is, you know, AI to get to search, or for to get opinions, and assist that, and still, that become valuable. And so this happened to us because of the fundamental work that we do, but it's not because we did anything for it specifically. And nor are we really now. I think we continue to think about communities and conversation. And it turns out, yes, that is incredibly valuable. Yeah, I mean, just what we always believed. So one of the things that you were at the home of was these data deals with Google for Gemini and OpenAI. And so I'm curious when did those conversations start to happen internally at Reddit? Where you're like, hey, I think we're on to something here, where we have something everyone wants, which is this data. Yeah, I think it was, it's, it's like an evolution and it's quite complicated. Okay. So we, we've been open and enjoyed being part of the open internet and crawls. And, you know, that dare was part of real life.
research for these LLMs, 'cause they're before they became commercial entities. And, you know, at some point, they became commercial or commercializable businesses instead of research projects, right? And so that became complicated because one, you want appropriate value exchange two, on behalf of our users and their thoughts, which we are stewards of, we wanna make sure that we protect their right to deletion. So if they take down a post, it should go away in the internet. They're right to privacy. I mean, all these things that are really important to our users and making sure that, you know, they're good stewards of this corpus. - Yeah. - And so, you know, that's when we went through the process of, you know, striking partnerships and trying to figure out how to make this work. And so we have two partnerships with OpenAI and with Google and, you know, which addresses all these things, value exchange, how the data is used. You know, we help with training and we also are a reference resource. And so, you know, it's kind of under that context that we move forward on these partnerships. I think, and there's still so much to learn. I mean, at that time, you have to remember, you know, now Reddit is one of the most cited sources, but we didn't know at that time, right? We just, you wouldn't have found that out. Have we not been in those models? So this is a, you know, a constant learning process. And those experiences and product experiences are constantly changing too. I don't think that's settled. I mean, the architecture of the internet, the economy, the internet is changing. So fundamentally right now, where that will land, like nobody knows yet. - Yeah. - But we tend to be a company that like, we believe in this technology of AI. We also believe in its limits in terms of, you know, what it can do and where humans, I think we are still better. And we like being a part of, of helping that technology come to fruition and we're a user and beneficiary of it. So I think that's allowed us to do that, you know, in a way with structure and appropriate value exchange. - I love that because I feel like a lot of the conversations lately have shifted from like SEO to like AEO, answer engine optimization. And it was the foresight or like the, at being ahead of the curve that like, you guys are in that right now, where you guys are being cited and answer engines and they have the conversations that are from Reddit. I think it's so cool. - Yeah, and also in some ways, you're very much like the stewards of defining AI going forward because you are, you're the stewards of like the data that is taking us into the, I don't know the future of what AI says to people. - Yeah, for sure. - I mean, so much of what it, no pressure. - You know, I think what we have, I think is really, really special. And we think about, you know, growing it and making sure it's appropriately, like we're good stewards of that trove of human intelligence. I think we believe in humans. We are focused on being the most human place on the internet, maybe ironic for a tech company. And I think that when you look at even where we are today, from, you know, let's say how LLMs, give very succinct, succinct, efficient answers, which, you know, it accomplishes that task. I think you look at Reddit and it stands in contrast to that. And maybe in complement, right? It's like, people will maybe want efficiency and an opinion on an answer from an LLM, but they right now are validating more than ever in contrast to that on Reddit, that exact query. They're literally typing in the same query. ChatGPT told me these were the best running shoes. Reddit, what do you think? Or they're typing in that same query. What are the best running shoes here? And then what are the best running shoes on Reddit to get the compare, contrast, and the validation? And I think, I don't think, I think that behavior is becoming more commonplace and will not go away. I think people will always want that, even if their behavior changes and they use more LLMs, et cetera. So it's a really interesting moment to play that role. Yeah, in that triangulation, I think it also goes to show how important, and I mean, how much people trust Reddit as a source for triangulation for the answer. Hey, guys, so it's come to my attention that many of you don't know. Jean and I have a matcha brand called Sisters Matcha that we created and founded ourselves. What, no way, a matcha brand? Yeah. We started it in October, 2024. Jean and I have worked and lived on this matcha farm in Japan. It's sourced from Wazuka, Japan, which is an hour and a half outside of Kyoto, and the brand means the world to us. It is a small family-owned farm, and we actually travel back to the farm and handpick the matcha ourselves. So you can find out more about Sisters Matcha to try it, check it out, buy it, buy it at www.sistersmatcha.com. That's SistersMatcha.com, and already back to the show. All right, so on the topic of reinvention and closing, I'm a little confused because you went to Stanford, I went to Harvard, Shree went to. You also went to Harvard, Shree went to Stanford. We are the Tiger Sisters. You are on the Tiger Sisters. We're all still paying off debt. Yeah, true, true, expensive educations. So out of all that, what part of your educational journey do you think taught you the most about being a business leader? I think I learned different things from different places. I think my undergraduate was. I went to Yale, I think, was really taught me to think very broadly about the world. It's just such a diverse environment with people who are different angles on society and big ideas, which I think is really important when you think about strategy, and you're thinking about the future of human behavior or internet, that's those kinds of questions that are very tangled with society. Liberal arts coded. Liberal arts foundation, right? I think that's what I got from that part of my education. I think from my time at Stanford, which was a master's in the engineering school, I think that gave me what I call technical confidence. Like the ability to go head to head and be like, you know, I can dive into infrastructure. I can deal with the math and the ML models. And, you know, I can lead a team that does that work confidently. And I think that's what I got from that. And being viable in that community, feeling comfortable in that community. I think similarly, at business school, it was becoming conversant in business vernacular, which is a thing unto itself, I guess. And I think I got a community of business leaders and professionals who are like my personal and professional sounding board for my career. We're just like my go-to on so many things. And I think is so valuable as you go through like different arcs in your personal career and your job. And I think that's what I got from the business community. And part of that was I had not met a lot of LGBT to business professionals until I went to business school. And so that became a community for me as well. And that was amazing, to gain also, you know. - So it sounds like Harvard was your favorite then. - No, I think Stanford. (laughing) - No. - I love all of them. (laughing) - I mean, all of them have shaped you in different ways, right? - I was building yourself up, building your confidence up, growing your relationships. - All different and not all experiences, maybe other than the undergrad that I hope that I couldn't have architected. And I almost couldn't have imagined. - Yeah. - The college is like this like monolith in my mind is like you go to college and you know, I wanted to go to a good college and I wanted to have a good job. And that was like this very high level idea. - Yeah. - And then you go there and you have this experience you're like okay, that's, and it took me probably while to reflect on that and be like that's what I got out of that. And this is what I got out of this. Like it takes some distance to maybe reflect and see, this is actually what I got out of it. I could not have architected that and nor could I have predicted it for myself. - Yeah. I did not dream of being an like a technical person. - Yeah. - I often tell people that like you, it's very hard to sit down and architect. You're like some people do it successfully. But for most people it's like a journey of discovery. - Yeah. - And reinvention in there. And like I think the two of you, I think of reinvented into tiger sisters, which I think is really awesome and inspiring. And I have one thing for myself. Like maybe there'll be another reinvention in incarnation. Like I hold out that hope, you know, it was many years ahead. - Absolutely. - That'll be another one. - We say you can reinvent yourself at any time. - Yeah, I mean it's multiple chapters. I like to think that all the time. And that keeps me just excited. - Yeah. - I love that. Well, thank you Jen so much for joining us on this episode of tiger sisters. It's been such a pleasure to talk to you. We're so badass. - Yeah. - That's very nice. Thank you for having me. It was great. I enjoyed the conversation a lot.
Podcast Summary
Key Points:
Jen Wong joined Reddit in 2018 as COO after being recommended by a friend, drawn by the platform’s unique community-driven model and its potential for sustainable growth without heavy investment.
Reddit’s advertising strategy focuses on contextual targeting based on user interests and community engagement, leveraging anonymous user behavior to deliver high-intent, niche, and personalized ad experiences.
The platform’s structure—built on autonomous, community-specific moderation rules—creates safe, high-quality spaces where users feel comfortable sharing personal, vulnerable, and authentic thoughts.
Despite perceptions of Reddit as a place for disaffected or isolated individuals, the majority of communities are positive, supportive, and rooted in shared passions, with strong emphasis on civility and safety.
Reddit’s enduring relevance stems from its unique focus on communities and human conversation, making it a vital source of real-world insights and a key data trove for AI training, especially in natural language understanding.
Reddit’s partnerships with OpenAI and Google for AI data licensing reflect a balanced approach to data use, prioritizing user privacy, deletion rights, and value exchange while contributing to AI development.
Founders use Reddit for organic product promotion by adding value to conversations—such as sharing expertise or hosting AMAs—rather than direct selling, aligning with the platform’s culture of trust and authenticity.
Jen emphasizes that personal and professional growth, including reinvention, is a journey of discovery, not a planned outcome, and that staying open to change keeps one excited and adaptable throughout life.
Summary:
Jen Wong’s journey from Time Inc. to leading Reddit as COO highlights the power of serendipity, personal values, and deep alignment with a platform’s mission. She joined Reddit in 2018, drawn by its community-first ethos and the opportunity to build a business that respects user privacy and authenticity.
Unlike traditional platforms, Reddit scales its business through contextual advertising that leverages users’ real-time interests and community engagement, avoiding intrusive data collection. The platform’s success is rooted in its unique architecture—where each community governs its own rules, fostering safe, passionate, and highly relevant discussions. This culture of openness and trust has made Reddit not only culturally resilient over 21 years but also a critical source of human-generated data for AI development.
Through strategic partnerships with major AI firms like OpenAI and Google, Reddit ensures ethical data use while preserving user privacy and control. Founders leverage Reddit for organic growth by adding value to conversations rather than selling products directly. The episode ultimately celebrates Reddit as a living ecosystem of human connection, where authenticity, community, and reinvention are central to both personal and professional success.
Jen’s journey underscores that leadership and self-discovery are ongoing processes, not linear achievements, reinforcing the idea that one can continuously evolve and stay inspired throughout life.
FAQs
Jen left Time Inc. to join Reddit because she was drawn to the platform's potential for pure growth and its unique position as a community-driven, open internet space. She also valued the insight she gained from editors at Time Inc. who regularly used Reddit for inspiration, and saw an opportunity to build a business from a clean slate.
Reddit prioritized advertising as its primary business model because it scales with users and aligns with the platform’s open, community-first values. The strategy focused on context-based targeting—using users’ interests and activities in communities to deliver relevant ads—without relying on personal data or user identity.
Reddit’s communities are self-curated and focused on specific interests, with strong moderation and clear rules tailored to each community. Unlike LinkedIn, where professional identity and resume-based content dominate, Reddit fosters authentic, personal sharing in a safe, low-pressure environment that encourages real belonging.
Reddit hosts a range of community types, including positive, supportive ones and debates on controversial topics. However, it maintains safety through clear community-specific rules and a strong emphasis on civility. The platform actively works to ensure moderation is effective and that communities remain positive and inclusive.
Founders are encouraged to add value to conversations rather than directly promoting products. By sharing expertise, offering insights, or hosting AMAs, they build trust. Direct product placement or selling is generally discouraged, as it violates community norms—like interrupting a dinner party to sell a product.
Reddit’s unique structure around communities, user anonymity, and high-quality, niche conversations has allowed it to stay relevant. It consistently evolves with user needs and avoids mimicking other platforms, focusing instead on being the most authentic and human-centered space on the internet.
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