Alexis Ohanian: Why Discipline Creates Freedom & How to Incorporate Routines in Your Schedule in Order to Succeed

How do you stay disciplined when life gets busy? What’s a routine that keeps you on track? Today, Jay welcomes Alexis Ohanian, tech founder, venture capitalist, and advocate for social change. Known as the co-founder of Reddit and founder of venture firm 776, Alexis shares the profound lessons he's learned from building communities, parenting, and navigating personal and professional challenges. Alexis shares insights into the evolution of online identities and the surprising dedication of individuals who moderate and foster online spaces; his role as a father, offering a candid glimpse into the delicate balance between introducing his children to the digital world and preserving their innocence. The conversation also tackles larger societal issues, such as the importance of role models for young men and the transformative potential of positive male friendships. Alexis doesn’t shy away from discussing the darker sides of technology, including the need for ethical boundaries and his personal experiences advocating for change within Reddit. In this interview, you'll learn: How to Foster a Sense of Community Online How to Introduce Kids to the Internet Safely How to Navigate Cultural Differences in Relationships How to Encourage Grit and Perseverance in Children How to Lead a Team with Empathy and Vision How to Prioritize Family While Building a Career In today’s fast-paced and ever-evolving world, it’s easy to lose sight of what truly matters. Yet, the foundation of a fulfilling life lies in embracing challenges, building strong relationships, and staying true to our values. With Love and Gratitude, Jay Shetty What We Discuss: 00:00 Intro 00:40 The Human Mind’s Deep Need for Community 02:59 The Challenges of Moderating Online Communities 05:26 Raising Kids to Navigate the Internet Safely 10:13 Why AI Can’t Replace Human Empathy 17:28 The Power of Optimism in Uncertain Times 21:42 Drawing Ethical Lines in Content Moderation 29:52 Saying No to Risky and Irresponsible Startups 33:05 The Key Milestones Behind Reddit’s Success 35:05 A Family’s Journey of Resilience and Survival 41:46 Coping with Family Tragedy While Moving Forward 52:27 The Joy of Seeing Hard Work Pay Off 01:00:15 Lessons Learned Through Loss and Reflection 01:12:45 Building Greatness with a Strong Partnership 01:19:19 Choosing the Right Partner for Life and Growth 01:27:23 Teaching Kids to Embrace Failure and Grow 01:35:27 Alexis on Final Five Episode Resources: Alexis Ohanian | Facebook Alexis Ohanian | TikTok Alexis Ohanian | LinkedIn Alexis Ohanian | Instagram Alexis Ohanian | YouTube See omnystudio.com/listener for privacy information. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jay Shetty?

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• 0:44Jay Shetty?

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• 1:30Jay Shetty?

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• 2:10Jay Shetty?

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• 2:40Speaker 01

  The more comfortable you can be in the discomfort of constant change, the better.

• 2:44Speaker 02

  His co-founder of Reddit. Alexis Ohanian has stepped in the room.

• 2:48Speaker 01

  When we build any kind of social media platform, we are ultimately deciding what belongs and what doesn't. If you can be equipped and you can exercise those muscles around problem solving and learning, you will be at the forefront for however this technology changes things.

• 3:03Jay Shetty?

  What do you uniquely understand about the human mind?

• 3:10Speaker 03

  The number one health and wellness podcast.

• 3:13Speaker 04

  Jay Shetty. Jay Shetty. The one, the only Jay Shetty.

• 3:19Jay Shetty?

  Hey everyone, welcome back to On Purpose, the place you come to listen, learn and grow. I'm so grateful because I get to dive into the minds of people that I find fascinating and interesting, people who have incredible insights, who are willing to share their soul, their hearts, with the pains, the overwhelms, the stresses and the joys of their journeys. Today's guest is going to do just that for us. His name is Alexis Ohanian, founder and general partner at 776, co-founder of Reddit. Alexis Ohanian is a tech founder and venture capitalist. He wrote a national bestselling book without their permission and is co-founder of Reddit,

• 3:59Jay Shetty?

  one of the largest websites in the US, currently valued at more than $15 billion. In 2020, he founded 776, a new firm built like a technology company that deploys venture capital with over $900 million plus in assets under management. In 2022, Alexis launched the 776 Foundation to support marginalized individuals and announced a $20 million commitment to climate action through his 776 Fellowship Program. Ohanian is also a vocal advocate for paid family leave and also hosts the Business Dad Podcast. Make sure you subscribe if you don't already. Welcome to the show, Alexis.

• 4:41Speaker 01

  Thank you, Jay. That was great. Can you introduce me everywhere?

• 4:44Jay Shetty?

  Happily, happily. Let's do it.

• 4:46Speaker 01

  I'll record that. Let me bring that everywhere I go.

• 4:49Jay Shetty?

  I would love for you to do that. It would be an honor. It would be an honor. Alexis, it's so great to see you.

• 4:53Speaker 01

  Thanks, man.

• 4:54Jay Shetty?

  We bumped into each other randomly at Angel City FC games in Cannes more recently.

• 4:59Speaker 01

  That's right.

• 4:59Jay Shetty?

  And I've always been fascinated by your journey. And when I heard that you were interested in talking to me, I was really excited about that because I think you can have so many perceptions of tech founders and community app founders from afar.

• 5:14Speaker 01

  Yeah.

• 5:15Jay Shetty?

  And then getting to know them more intimately always leaves me feeling like I've learned something. So I'm happy you're here and I wanted to start off by asking you this. What do you uniquely understand about the human mind that has helped you get to where you are today?

• 5:32Speaker 01

  The human mind seeks community and Reddit was noteworthy, especially in 2005, because it was pseudonymous, right? Because you didn't have to have your government name, didn't have to have your photo at a time when Zuck was building Facebook, which was very much that. And you could come together, not because you have something to say and you want people to follow you. You come together around community. That is the goal. We all love Angel City FC. We join that community. We're a part of it. We all love stapling bread to trees, which is a real subreddit. Everyone's got their hobbies. We all join. We post photos of the bread stapling. We talk about it. We commune. And I grew up on the internet. I learned how to code from strangers on the internet.

• 6:16Speaker 01

  I convinced other strangers when I was a teenager. To basically pay me to build websites for them. Because HTML building websites was a thing I was very keen on. I just enjoyed the design. I enjoyed building. And it made me feel really cool to be a child on these message boards. Like a teenager being able to get paid by adults because I had a skill they didn't have. And so I learned so much through those experiences. And I learned from video games, leadership skills. If you can believe it. And and in building Reddit, it was simply a way to build a better type of forum. That would be a better way for online community to form. And over the last now 20 years since, I look first and foremost for these things.

• 6:58Speaker 01

  And I think in a world increasingly more fractured and divided. And where people spend just frankly, more of their time online. These spaces matter even more. And it's something, you know, for the first probably 10 years of Reddit. Most people didn't think it was possible for people to care that much about their online identity as they did their offline. And that was one of those things that I really held fast to. And I think today we sort of take for granted. Of course, people care in many cases, much more about their online persona than their offline one. And I just hope to see it get used for more and more good at a time when, like I said, there's more division than ever. And the power of community is still something that I think runs deep in our species. And the internet is just a new medium to to connect.

• 7:43Speaker 01

  And hopefully for good.

• 7:44Jay Shetty?

  Since building it and starting it, what have you been surprised by about community? Maybe something that you believed to be true about humans, but has been disproved? Or something that you never knew about humans that you've discovered?

• 7:57Speaker 01

  Early on, people were often very confused why someone would spend so much of their free time moderating a community for free. Essentially, you know, community management. And I'd often frame it, you know, I grew up here in the United States. I was a Boy Scout. There were parents who were often involved volunteering for the Boy Scouts. They'd be there for camping trips. They'd be there for meetings. They'd be helping out volunteering their time and energy. For community. And so I really took for granted the fact that if people wanted to do this offline for whatever organizations, faith groups, et cetera, that online, these connections matter just as much, even though they may not feel as real. And in fact, you

• 8:41Speaker 01

  can scale your time so much more efficiently, right? You can build a community of literally millions of people from your home. And that gives you a sense of purpose and a feeling of, you know, being able to create this sense of belonging for people. And that's, that's really meaningful. I mean, that is something that I've just seen continue to impress me. I, I did not realize the full scale to which that would actually be working. And then probably the other side of it is just how important creating that sense of why for people is. I remember reading the book Bowling Alone, which talked a lot about a generation of adults who, you know, used to be a part of bowling leagues and these other things, but you saw this decline. And people, in this case, it was, it was men,

• 9:25Speaker 01

  but, but in general, people needing to find more and more of that connective tissue in their community and not having that sense of belonging. And I feel like in a lot of ways, the internet has created great versions of it. But at the same time, it's also created these, you know, the sort of dystopian versions of it where you can spend all of that time absorbed in a world that is online and miss out. I think we have a generation of young people who, I'm generalizing here, but a lot of whom don't have the same muscle that they, they have not exercised the same muscles that we had growing up when it comes to relating and connecting to their fellow humans sitting across from them. And, you know, as a father of two kids, it's something I think about a lot.

• 10:03Jay Shetty?

  Yeah. Talking about the two kids, I know, I know you love being a dad and

• 10:06Speaker 01

  Yeah.

• 10:07Jay Shetty?

  it comes across as such an important priority in your life as well. Like, how would you go about explaining the internet to your kids when the time is right?

• 10:17Speaker 01

  I've already had these conversations with Olympia and she just turned seven. And I try generally, I think my wife and I both, we, we try not to talk down to our kids. Like, I really will explain a concept, not like I would explain it to another 41 year old, but at least like, I, I want her to, to ask that follow-up question of like, well, what is that? Or why? Or how? Or so I, you know, and we've had versions of this conversation.

• 10:45Speaker 01

  She does not understand the internet. I mean, do I? Does anyone? But there have been little glimpses that I have given her into it, but very, very, very tightly controlled. Really, the only time she's ever online right now at seven is playing Roblox, which she will do either with me and her mom or some friends from school. She knows the internet basically as this, this basically Roblox. And a place where she has fun and runs around and that's it. But that's the extent of interacting with folks. I would like to put off social media. Now, yes, our kids have social media accounts. It's run by us. You know, now that she's at an age of consent, it's basically just like, you know, we're, we're quite rarely putting photos up.

• 11:30Speaker 01

  And it's only because she's like, oh yeah, you can, you know, post this up. But the understanding of it is social media is something that I, for as long as possible, would like to put off.

• 11:42Speaker 01

  Simply because this just isn't.

• 11:45Speaker 01

  I think, I think we have gotten so good at creating those feedback loops that bring people back. And plenty of people have written about this and talked about this. I mean, this was one area where not intentionally, but Reddit was designed differently because it wasn't about real name and it wasn't about real photos. And it wasn't about, hey, follow me, let me collect likes. It was about, hey, we all like this community. Let's share things about it that we, we care about. But generally speaking, it's still a black box and I'd like to keep it as much as possible. We've had that initial conversation of why it's so important, you know, to only be playing Roblox with Papa and Mama. That we, if we're playing with anyone, if we're talking to anyone, it's only the people, like the three people who we know.

• 12:31Speaker 01

  And it's this balance where I don't. My take is I want to expose her to just enough that she can start to build that resilience or at least start to understand like, well, this is why you don't talk to random people on the internet. While still trying to preserve some amount of innocence, which is just such an awesome part of childhood. But at the same time, making sure she's steered for the reality of what the world is like. But probably my favorite application of the internet is every night I'll ask her a big question and some nights she really doesn't want to. She doesn't have one. And so she'll just look at something on the table and be like, okay, where does salt come from Papa? And I'm like, okay, I see what you did. You just looked at the salt on the table, but that's fine. We'll find out and we'll, we'll ask AI, usually ChatGPT and fire it up

• 13:16Speaker 01

  and, and engage in this dialogue, which, you know, probably would have been a Google query a few years ago, but now is way more interesting and engaging. And, and I want her to know, like, hey, you, you will have access to these tools that your Papa could have only dreamed of as a kid, that your grandpa, your great grandpa could have never even imagined. They would have thought they were wizards. And I want you to know, this is a tool. This is a resource for you to use to help you exercise. It's, it's a bicycle of the mind, right? And it's, it's a tool. It's not an end all be all, but it's a tool for you to use that can provide tremendous value for you. When, when Papa doesn't know, like what temperature he needs to take the ribs off the smoker, like he's asking this because he, he's looking for a solution for an answer. But whether you're curious about salt, or you need some help cooking, or you're just curious about the world, like, I want

• 14:01Speaker 01

  her to start thinking of the internet as a resource, but, but not this, you know, end all be all for learning and for solving problems. But we'll see. Hey, I'm early in the game. I don't know. You have to, you have to check back in with me in a decade or two to see if I did okay.

• 14:16Jay Shetty?

  Hey, I'm Jay Shetty, and I wanted to invite you to a brand new, interactive, no charge workshop, Renew You, that I'm eager to share with you. Over the years, I've worked with thousands of people across the globe, and I've noticed a common theme. Many of us are feeling stuck, overwhelmed or disconnected. We're going through the motions of life, but not really living. Does that sound familiar? You feeling burnt out, uninspired, or like life is just passing by without meaning? Maybe you're struggling to make the impact you know you're capable of, or perhaps you're craving deeper connections with others. If any of this resonates, then I want you to know that change is possible, and it starts with the choices you make today.

• 15:00Jay Shetty?

  In this workshop, I'm going to share five simple yet powerful steps that can help you reignite your passion, purpose, and joy. These are the same principles that have helped me and countless others reshape our lives from the inside out, and I know they can do the same for you. You'll walk away with actionable strategies to revamp your daily routine, find your true purpose, and create meaningful connections. And the best part, this workshop is completely free. These changes don't require massive overhauls. It's about making small intentional shifts that can lead to big results. This workshop is more than just learning. It's about doing. I'll be guiding you through reflections and exercises that will help you start creating

• 15:45Jay Shetty?

  the life you've always dreamed of, right here, right now. Go to www.renewyouworkshop.com to access this at no charge and start building a life that's not just lived, but truly loved. See you there. I mean, I remember having Britannica Encyclopedia to have to search.

• 16:06Speaker 01

  When I got the Encarta, so we didn't have the books, but when I got the Encarta CD room. Oh my God.

• 16:11Jay Shetty?

  Yeah, it was amazing.

• 16:12Speaker 01

  Oh my God, and they had a few videos on that too, so you could watch, you know, you're watching like a lion across the savannah and you're just like, this is amazing.

• 16:20Jay Shetty?

  Yeah, it's incredible. And I like that. I like, I like the way you're using it in a curiosity building way, in a solution, answers oriented way. That sounds like a, a smart decision.

• 16:31Speaker 01

  Here's the one thing I am sure of, because I do get asked this question a lot about like, what should my, for college age, parents of college age kids, or even college kids themselves, what should I be learning? What should I be studying right now? 10 years ago, I literally went across the country. I went to 82 universities for that book, talking about the importance of learning how to program. Uh, so sorry, everyone. It turns out that's not as important anymore. I mean, for the time, I thought it was actually directly, it was, it was pretty good advice. And actually, a number of the folks, you know, like the founder of Deal, uh, which is now a billion dollar company, was there in the audience for one of those talks. You know, today, the advice I would give is a little more nuanced because learning to program is, is still going to be important in the same way that learning to speak a language or doing basic arithmetic is important, but.

• 17:13Speaker 01

  The tools we will have at our disposal to literally write code are going to be so formidable. Like, I mean, even the improvement the last couple of years are good, but in the next few years, it's up to the profession, the person is not going to go away, but the amount of output you'll get out of one person is so much greater. And so my thinking is, all right, there's lots of different areas where AI may not necessarily replace human work, but is going to be an amazing superpower. And so what do I want for my kid or even for anyone's kid who's entering a workforce? Is probably to, most importantly, build skills that I know are going to be durable, call it a decade or two from now.

• 17:53Speaker 01

  So empathy is a skill that I think will be the last bastion of AI. Like you're seeing, you've probably seen the videos now of robotics and the leaps and bounds that's starting to make, still early days. But, you know, there are skills, there are professions where empathy is so, so, so important. And the physicality of being present, one human to another, where, at least I personally believe, if we ever get to that point with AI and with robotics, we can pretty much call it as a species. Cause I like, at that point, I don't know if you're that self-aware to be that empathetic and that effective in those moments. When we can, my sister's an RN, when her job can be done just as well, or ideally even better by a robot as a nurse, when that job can be done,

• 18:38Speaker 01

  you'll also have to then explain to that robot that they're going to be a nurse for the rest of their lives. And if they are that all-powerful, there's no way they're doing that job. Because the humans who do it are so remarkable. Like, it's not that if they would, that's the moment when the robots are like, no, no way, no chance, we're enslaving you now, game over. Because the humans who are doing that, that's the last mile of humanity required in terms of like, the physical dexterity required, the creativity, the problem solving, the empathy, all of that stuff. So she's got job security for a very long time. And, and I just believe.

• 19:15Speaker 01

  If you can be equipped and you can exercise those muscles around problem solving and learning, you will be at the forefront for however this technology changes things. And, and you know, that's the advice we're trying, we're trying with Olympia. There is only one.

• 19:30Jay Shetty?

  Yeah, it's got a long way.

• 19:32Speaker 01

  But, uh, but I would say that's, that's where it is. The more comfortable you can be in the discomfort of constant change, the better. And then look towards the skills I, and this is the part that gets me fired up. I actually think we're going to see, the pendulum is going to swing back for a lot of human work that we would have considered more artisanal because we'll crave the humanity of it. So I think, uh, food. So, so again, imagine a world where, you know, I've tried, my wife's a great baker. I really just do pancakes. I tried making croissants over COVID because I was like, I love a good croissant. Who doesn't?

• 20:07Jay Shetty?

  Yeah.

• 20:07Speaker 01

  And I was like, let me just watch a YouTube video and see how to make a croissant. Making croissants is a lot of work. You gotta take that sucker out of the fridge regularly, put more butter in, knead it like it's, it's a labor of love. I made it once, they turned out six out of 10. Okay, they were edible, but like not great. But now every, I will never make them again. But, but now every time I eat one, I have so much more respect for the process. Making, you know, if we imagine automation, robotics, the world's greatest croissant should be pretty solved and pretty affordable and pretty cheap as technology. Again, the robotics of doing all that tedious but important work, it'll be solved and we will all be able to get a magically delivered, perfect croissant, right on time, fresh, affordable balls. This is a dumb example, right?

• 20:51Speaker 01

  But in a world where you can see robots making commodities out of something like food, I actually think then the pendulum, again, as humans, swings to the, the artisan who's actually spent their lifetime perfecting this thing. And even when you can get the commoditized version, some people sometimes will still seek out that very human version of it. You know, the entertainment industry, we're in LA right now. It's undeniable that AI is going to have a huge impact in how we make films and it will affect 80, 90% of the industry in really big ways that we still can't fully understand. And I just took my daughter to see Back to the Future for her birthday on Broadway. And I'm sitting there and I'm realizing, you know, and actually, by the way, the special effects,

• 21:35Speaker 01

  all these dope LEDs, like it was actually one of the most dynamic theater experiences I've ever seen. Right? That's technology. My bet is 10 years from now, live theater at a time when the commodization of so many parts, not all of, but so many parts of like on-screen storytelling happens. And it gets easier and cheaper and more efficient and more dynamic. Like you will see a big shift in that industry and it's not going to go away. It's going to elevate so many things. But every screen we look at for sure, our phones, our televisions, whatever, will be so programmed to show us when we, what we want, when we want it, how we want it. A part of our humanity will miss, you know, thousands of years ago when we were sitting around a campfire and that great storyteller

• 22:18Speaker 01

  was doing the voices and the impressions. We were like, oh, that's hilarious, Jimmy. Do the story again at the time we tried to catch the gazelle. Right? That's ingrained in our species. So I actually bet 10 years from now, live theater will be more popular than ever because again, we'll look at all these screens with all these AI polished images and we'll actually want to sit in a room with other humans to be captivated for a couple of hours in a dark room to feel the goosebumps of seeing live performances of human performances. And so I think we'll see this across a number of different sectors and areas that'll feel anachronistic. It'll feel crazy that in 2040, the hottest ticket in town will be a live performance. But I actually think, I think there's some truth to that. I think that's

• 23:02Speaker 01

  why I'm so bullish on sports because no one's going to pay money to cheer for and cry for a robot kicking a soccer ball. Like we need humans doing that. We need, we need to feel their pain and their success and their triumphs. And those are the areas that get me most hopeful because it's, it's kind of a nice throwback to when we were just hunting or growing the things we needed to live when, you know, the distractions we had were literally the humans around us and the community we had were basically the only people we all knew for our entire lives. And, and there are parts of that that I actually think will nourish us even in this, you know, future. Have all parts of you always been that optimistic? I've definitely always been a tech optimist. I, I think.

• 23:44Speaker 01

  Look, building Reddit, I mean, you know how I resigned in protest in 2020 because I was, despite being the face of the company, spending, you know, 15 years, building it, turning it around. You know, I found myself in board meetings, and this is all public now, but I'd found myself in board meetings where I was the only person out of five who was advocating for banning, like, watch people die, literally a community of, you know, hundreds of thousands of people sharing videos of just horrible, usually, like, closed-circuit television or closed-circuit camera footage of just awful stuff, people dying, suicide, murder, all these accidents. And then again, it comes up again around communities like explicitly built on racism and things that I just, I knew were bad for business, were bad for society, were just not

• 24:28Speaker 01

  things that we should be fighting for. You know, when I did part ways, I was so pleased to see the response finally was, okay, we're gonna ban these things, because it shined a light, right? And what it also taught me was, this was four years ago, was that I had, I didn't have enough agency, and that was my own creation, that was my own doing, but I was never gonna put myself in a situation again where I couldn't be doing not just the best work of my career, but also in a way that aligned with my values. And what's been a phenomenal result is for the last four years, I've had so much wind at my back from making that decision, from aligning those values. And I still think the internet can bring out the best in us. I do, I do really believe that. And I can also accept the conflicting

• 25:11Speaker 01

  view that it enables the worst of us. And I obviously want to be on the side of the former, and so I try to use my platform as best I can for those things and to, you know, curb the worst. I think I have to remain an optimist because I'm still optimistic about humanity, and to the extent, these tools are just a reflection of society, of our world, and I need to believe that, you know...

• 25:40Speaker 01

  There is hope for us to figure this out, to get a line that at the end of the day, nearly all of us still want the same things. We want to live decent lives. We want our kids to live hopefully better lives than we did. Like, there are some practical needs that we still have from hundreds of thousands of years ago that I think we need to meet. Like I said, I want to spend my years supporting all the stuff that I know my girls will be proud of.

• 26:06Jay Shetty?

  Walk me through your thought process. How do you process tens of thousands of people subscribing to a Reddit that's about watching people die?

• 26:16Speaker 01

  Yeah.

• 26:16Jay Shetty?

  Because I want to know how someone like you who's building something thinks about that.

• 26:20Speaker 01

  Yeah.

• 26:21Jay Shetty?

  It's easy to be like, we should ban that. We don't want people to see that. But I wonder what your thought process is and how you reconcile the fact that there are people who are interested in something like that versus there's so much good. And I'd love to hear from a programmer, coder, builder.

• 26:36Speaker 01

  Well, look, early on, these really radical communities almost never exist. Certainly, back then, because there were just fewer people online, you know, 2005, starting Reddit, I was just hoping it would work. There were so few people online actively creating content that, you know, for early years, it wasn't even a thing. It never even came up. And when it did, it was just an easy ban because it was a one-off post. I left, so sold the company in 2006 to Kind and Ast, stuck around till 2010, then I left, went, became a partner Y Combinator, started a venture fund, and I came back in 2014 as executive chairman. And that was in the wake of a previous CEO infamously defending revenge porn. This was definitely Reddit's nadir. And he'd written this infamous blog post defending keeping

• 27:21Speaker 01

  these horrible photos up. And that was not surprisingly one of his last acts as CEO. And I was asked by the board to come back. I said, great. First thing we did, shocker, ban revenge porn. Pretty easy, very obvious thing to do. And then it was a task of, one, rebuilding the business, rebuilding the faith, you know, with users, with brands, with everyone, and then starting to just modernize all the things. And then as this stuff started coming up, and once it got to the board levels, you know, I'll give you the steel man version of the argument that I heard was, these are communities that are important because of free speech. And

• 28:00Speaker 01

  The one argument that I really did necessarily believe, well, I didn't believe, was around the therapeutic value of having communities like this for people who have PTSD, like soldiers or medical folks. And I pushed back pretty hard on that one because I just still didn't, I didn't believe that it was real. The, probably the most elucidating takeaway for me was, once a spotlight was shown on it, the thing I would have respected more, even though I disagreed with it, would have been taking that same argument and making it publicly and just saying, yeah, look, this is a free speech issue. We feel like this should be here. And even though I would disagree with it, I'd still respect that it was consistent. But we know that's not what happened. What happened was, okay, yeah,

• 28:45Speaker 01

  our bad, we're gonna ban it now. And, and that for me was when I just, I realized, no, this isn't, this, I can't, I can't spend, I don't know, however many decades I got left on this earth, doing this and being a part of this. And I think the really telling thing in the era we're in now is, we have the first generation of young people who are like in their early twenties, who have grown up, like truly grown up on these social media platforms. And so it's exposed some of the most problematic parts. It's also exposed some of the most impressive parts, like the excellence of a nineteen-year-old, twenty-year-old who's pitching me to start her company. She is orders of magnitude smarter,

• 29:27Speaker 01

  farther along, just, just more impressive than I was at her age twenty years ago. And I, I think the internet has a huge role to play in that. At the same time, some of the stuff we talked about earlier, just trying to navigate an already really difficult time that is childhood, where your entire life is gamified, you know, based on how many followers you get, or how many hearts you get, or whatever else, also brings out the worst. But for me, no, that was, that was my breaking point. And I just realized,

• 29:56Speaker 01

  Like I said, I can deal with, I understand, you see this argument being made to this day. I respect that argument. And I at least appreciate when it's consistent. The inconsistency is the part that grinds my gears more than anything else. But we must also still accept the fact that, you know, the world wide web itself, the internet, is the totally open, free space. The difference is when we build any kind of social media platform, platform, whatever it is on it, we are ultimately deciding what belongs and what doesn't. We've all agreed that spam does not matter.

• 30:38Speaker 01

  Like, we are all okay impinging on the free speech of a spammer. And that's a pretty easy argument that everyone agrees. So if we agree on that, then now we just need to agree on where we draw the line. Because it's, there's no such thing as a totally free network. Because, again, we've all agreed, we draw a line on spam. So where else does it go? And, like I said, for me, and I realize it is, it's important for it to be a gray line. And I can go into all the, there's a myriad of reasons why it's actually really helpful to have it be a gray line. The short answer is, if you make it a bright line, then toxic users will go right to exactly where that line is and say, great, okay, I'm just gonna hang out here on this line and troll, because that's how they get satisfaction. So it's actually beneficial to have the gray line. So I totally understand the gray line.

• 31:21Speaker 01

  Even our laws in the United States have a gray line, usually get interpreted by judges or juries, what have you. So that's helpful. But I think, and this is where the tech optimist in me comes in. When I look at the next generation of consumer social, these apps, and every app starts with teens, usually teen girls, college-age girls, they drive all online culture and adoption. You look at Instagram's success, you look at Snap's success, you look at TikTok's success, it's the same story. Then the apps that are starting to make traction, and it's still early days, but they're much less based, even the ones that have blown up and fallen back down, the Be Reals of the world and some of these others, they're all much less based on the sort of internet popularity contest,

• 32:04Speaker 01

  and they're much more based on connecting with your actual friends. One that I recently seeded is called Airbuds, and it's only about connecting over the music you're listening to. And it's purely like, this is the song I'm streaming right now on Spotify. React to it, vibe with it, share tastes. You know, it's, I think the culture has already now built up enough of an immune system that for this next generation, they're like, there's a pushback to the previous mold of social. And I think that alone will drive a much more healthy relationship to social media. But we'll see. But that is the lens through which we look at even making the investments. It's, okay, you know, when my kids are old enough,

• 32:46Speaker 01

  how good am I going to feel about this being a multi-billion dollar business that they're on?

• 32:50Jay Shetty?

  Yeah.

• 32:50Speaker 01

  And, and look, admittedly, you cannot predict that. It is, there are so many different paths a company can take, any, any idea can take from day one to 10 years out, 15 years out, 20 years out. But we make the best assessment we can based on the founders, based on their attention and have, like I said, the, the starting line that these founders are on today is much more sophisticated than I was as a first time CEO right out of college. Because they, like, social media didn't exist. We had web forums, Facebook was still in colleges. There were a lot of blogs, like, it was just a very different world. Today, any, any founder pitching us has lived on social media, and they've seen the good and they've seen the bad.

• 33:33Jay Shetty?

  Yeah, absolutely. Yeah, I was gonna ask you that actually, is whether you, whether you decline investing in companies that you wouldn't let your kids use?

• 33:43Speaker 01

  Has it happened? There've, okay, there have been companies where we haven't even taken the pitch just because, and again, I don't wanna, I don't wanna get too high horse about it. No one's out here saying like, okay, I guess there were, there was one company that I hard passed on. Well, whatever, I can say it. They were a telehealth business, basically like handing out Adderall. And the business was growing very quickly, but there was no way they were doing it responsibly. And that was a hard, hard, hard pass. Like, it was both from a, I wouldn't feel good about my kids using this, also just from a risk standpoint, like, at some point, the FDA is gonna look at this and y'all are gonna have a bad time. Spoiler, the FDA did come down pretty hard on them. But we do, I guess I would take,

• 34:28Speaker 01

  though, it's the more optimistic version of that, which is, would I be excited to see this exist in the world that our kids are gonna grow up in? And if it's a hundred percent reusable rocket company, which we did see, called Stoke, hell, yes. Like, hundred percent reusable. So now you're talking about, one, there's an environmental benefit to it. And two, the things we'll be able to do for all of us here on planet Earth, when we have a much better, smoother relationship to low Earth orbit, will be very good for humanity. But there's a, there's a version for that. But it's, I think it's the, it's the more sort of positive lens.

• 34:59Jay Shetty?

  Yeah.

• 35:00Speaker 01

  The very interesting thing about founders today as well, they are more sophisticated. They also know just how big of a role technology plays in the world. And, and I know people would get on Zuck for his, like, aw shucks behavior, probably in the earlier days, where he just, it didn't, it seemed implausible that he could not realize how much power Facebook has. And I will say, to his credit, I think his tune changed on that. And also in his defense, none of us did. The, the idea, if you had told me, probably in, in most of the aughts, throughout most of the aughts, and probably even the early teens, that these social media platforms would be among the most valuable businesses in the

• 35:45Speaker 01

  world, I would have been very, very, very, very surprised. And, you know, they made some smart M and A moves, they did the things, but like, for all of us, or I can speak for myself, but I would wager Jack feels the same way with Twitter. In those early days, in those aughts, you know, it was about building something that you hoped people loved. It was about keeping the servers online. It was not about, well, what is gonna happen if all of a sudden there is an election that could decide, that there, there's an election whose fate could be decided based on whether or not a post goes up or not. Like, it would be laughable to have that conversation in a boardroom 10 years earlier, because it's like, hey, we might die next month. The company may not be here next month. But- Credit to this generation of founders. Every one of them knows going into it, hey,

• 36:29Speaker 01

  technology is shaping far more than it. It's not just these are the most powerful companies in the world or in our economy, but there are repercussions to it. And I think by and large, we want the good stuff to win. But these founders today are much smarter about it.

• 36:49Jay Shetty?

  This episode is brought to you by Indeed. I know how important every hire is for a business. If you need to make the right hire, this is a job for sponsored jobs. Indeed sponsored jobs helps find quality candidates when you need the most. You can reach who you need based on whatever criteria you're looking for, like skills, certifications, or location. In fact, people are finding quality hires on Indeed right now. In the minute I've been talking to you, companies like yours made 27 hires on Indeed, according to Indeed data worldwide. Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a $75 sponsored job credit at indeed.com/podcast.

• 37:32Jay Shetty?

  That's indeed.com/podcast. Terms and conditions apply. Need to hire? This is a job for Indeed sponsored jobs. This episode is brought to you by State Farm. We talk a lot about intentional decision making, and that extends to the practical stuff, too, like making sure your coverage actually works for your life. State Farm is there to meet you where you are, and they know how sweet it is to feel good about your decisions. Talk to a State Farm agent today to learn how you can choose to bundle and save with a personal price plan. Like a good neighbor, State Farm is there. Prices are based on rating plans that vary by state. Coverage options are selected by the customer. Availability, amount of discounts and savings, and eligibility vary by state.

• 38:15Jay Shetty?

  This episode is brought to you by Whole Foods Market. If you're talking about quality food, you can't forget Whole Foods Market, who've been holding themselves to the highest standards since they opened in 1980.

• 38:28Jay Shetty?

  That means you'll see thousands of organic products across their stores, from the produce department to the aisles. It also means you'll never see certain ingredients. They've banned artificial sweeteners and colors, high fructose corn syrup and more, so you can shop with peace of mind. Shop Whole Foods Market in-store or online. Did you and the other founders at that time ever come together? Because I imagine you're the only people in the world who understand each other and understand what you're building and going through. Did you ever get a chance to?

• 38:59Speaker 01

  I was not invited to those meetings if they were happening. Admittedly Reddit was this very solidly tier two company, right? Like we, you know, selling the company 16 months in was ludicrous, but it was life-changing money. It was $10 million for 16 months worth of work. I thought I was getting away with something. This is nuts. And then Particon and Ast, you know, the trajectory just sort of changed from when you're an independent startup. And so Reddit was really solidly a second-tier social media platform for over a decade. And then it wasn't until, you know, so 2014 I come back. And then probably by the late teens, once it's like, oh, here it's a billion-dollar company again. The business is back. Let's, you know, there's a path to an IPO one day.

• 39:41Speaker 01

  And so if those meetings were happening, Reddit was not invited, but rightly so. I wouldn't have been mad. I get it. We didn't have our shit together. But there's probably, I don't know, I've gotten to know Jack a little bit. I don't really know Zuck. Few of the other folks around these other platforms, but like there isn't, there's not a group chat.

• 40:04Jay Shetty?

  Yeah.

• 40:05Speaker 01

  There's not an active group chat.

• 40:06Jay Shetty?

  There's not a Reddit.

• 40:07Speaker 01

  No.

• 40:08Jay Shetty?

  There's not a Reddit, the subreddit. No, I love it. Alexis, I wanna, you know, even just listening to you now, the way you think is, is mind-blowing. It's fascinating. I think everyone's listening right now.

• 40:18Speaker 01

  Good.

• 40:18Jay Shetty?

  Is probably tuned in to just, you know, I think it's always brilliant to dive into that mind. But I also want to focus on your personal side today because I feel that. A lot of what's not seen in entrepreneurship is we get to see someone's brilliance, but we don't often get to see their, the personal sacrifices, the journeys, the choices, the challenges that come with that until many years after. And I actually want to go even before Reddit, I want to go back to your childhood. And I wanted to ask you, like, what's a childhood memory that you have that you feel has played a role in defining who you are today? Is there something that stands out?

• 40:57Speaker 01

  Oh, yeah, it's my first, one of my first and earliest memories. So I was probably like six, five or six years old. And so if you can't tell from the last name, I'm Armenian. And my great aunt Vera pulled me aside. So my birthday is April 24th, which is the, it's the Armenian Genocide Remembrance Day. So it's a conflicted day for me. But this particular birthday, I learned that it was the Genocide Remembrance Day. How did I learn? I remember my Aunt Vera pulling me aside and basically sitting me down and walking

• 41:38Speaker 01

  me through our family's story of survival in detail, talking about the costs, the toll it took, the things that her parents endured and what they saw and all of that. And basically how we got to America. And probably not a conversation you should be having with a six or seven year old, but it's, Armenians, we keep it real. She basically finishes up this conversation saying, listen, like, it's not a coincidence, your birthday is April 24th. You are the product of all of their sacrifice, of all of their hard work, of everything that they endured. You have a tremendous responsibility now to make the most out of this life that you have. When I was born in New York, here in the States, like, couldn't have asked for a better

• 42:23Speaker 01

  outcome, right, generations later. But what they endured is something that you will have to carry for the rest of your life. Happy birthday.

• 42:32Speaker 01

  And, and so, yeah, no, that has never left me. And, and she was an amazing woman. She was a public school teacher in Brooklyn, didn't have any kids herself. She was my grandfather's sister, so my great aunt Vera. She didn't have any kids herself, but she saved up as much money as she could. She's the reason I could go to college. I went to University of Virginia without taking on any debt. She paid for that all. And so, amazing woman. She framed that for me at a very, very young age. And so, I am very fortunate. I had an amazing, loving mom. I have an amazing, loving dad. I had the ultimate cheat code.

• 43:13Speaker 01

  Having that foundation, you know, growing up as a, as a white dude here in the States at a time when technology was starting to rip. My parents put some money together to let me get a computer. All that stuff lined up. And then it was imbued with this responsibility that I probably will never escape. For better or for worse, it's always gonna weigh on me. I'm never gonna feel like I've done enough. And I'm, I'm not mad about it. I'm grateful for it, because I think that brokenness has, has made me who I am. And it helps me do the things I do. But it instilled something in me that I just feel a tremendous responsibility for. And, and so, I, I don't know. I think I've probably spent, you know, I'm 41 now.

• 43:58Speaker 01

  I've spent three decades trying to earn that. And I still haven't. And I will probably spend three more decades trying to earn that. And I still won't. And it'll be a part of me that's always feeling, not that it's not good enough, but that I have not done enough. And, and, and I know this is a story shared by plenty of folks who are descendants from survivors of genocide and whatnot, but, oof, man, it just, uh, it always hits. And it's like. I feel, and it's this juxtaposition, right? Cause I go through my life largely stress and anxiety free, right? And, and I'm aware of that and I'm grateful for that. And then there's moments where I sit with it and I'm just like, I can still hear, I can still see Aunt Vera telling me this.

• 44:43Speaker 01

  And, and I'm like, like, keep going, like do better. Like you're not, there, there is, you have a responsibility, like do more. Needless to say, I'm being very, I'm very careful with explaining, like I want our, I want Olympian Adira, of course, to be proud as Armenians. They're only a quarter, but they're still Armenian. They got the last name too. I want them to be aware of this stuff and be proud of their family. And obviously their mom is going to have some, some big, big stories for them too. But um, I'm also trying to be mindful of the fact that like, maybe I'll wait until after, you know, they're a little older to really go into the details of it. But uh, you know, it's these things shape us, man. And I, like I said, I, I am, I mean, she could have just got me a normal birthday gift, but, but I'm still, I'm grateful for it.

• 45:27Jay Shetty?

  Is Aunt Vera still with us?

• 45:29Speaker 01

  She's not, she's not. She got to see me graduate from college, which was awesome. She was there in Charlottesville for that. And uh, yeah, no, it's wild. I've never, um, I don't know. I, I think, you know, one of the big things I did a few years back was I joined the Board of Robinhood, the nonprofit in New York. And, uh, I made a big grant to childcare there in the city in part because it was there in Brooklyn. When my mother and father were working at the, it was Ashland Place Apartments there in Fort Greene. Aunt Vera would pinch hit and just watch me and stuff. So my, one of my parents were at work and all that as a little kid. And so childcare makes a huge difference.

• 46:12Speaker 01

  And, and we were lucky enough to have a family member just across, almost across the hallway in another building. And uh, and so I wanted to pay it forward and that was in honor of her. That was a tribute to her. But uh, like I said, I'll be paying that back for the rest of my life, for sure.

• 46:27Jay Shetty?

  That's beautiful. I love hearing that. And uh, It must have felt so meaningful to be able to go back and serve there and have an impact there.

• 46:33Speaker 01

  I took my pops back too, and we were walking around. Four Greens changed a lot since the eighties. But the the block is still there and and it was great taking my dad through there. Just hearing stories from him and yeah, it's wild. Then you become a parent and you start imagining. You see this little person and you're reminded that you were that little person once to your parent. And it makes your relationship to them feel very different. It's it was a trip, but it was great to be able to come back. And I'll, like I said, I'm paying off those debts the rest of my life.

• 47:03Jay Shetty?

  Yeah, you were saying that, you know, maybe now in your life you can go stress free. And and you know, there are days where you're not feeling that. But in the beginning days of Reddit, it wasn't like that in your personal life.

• 47:14Speaker 01

  Yeah.

• 47:15Jay Shetty?

  You've mentioned to me and, you know, when we were talking before we started recording this. There were certain things happening in your personal life when you began that. Maybe if you revisited, you'd look at them differently. Could you

• 47:29Speaker 01

  Yeah.

• 47:29Jay Shetty?

  Walk us through what was going on and how you dealt with it at the time, first of all?

• 47:35Speaker 01

  Yeah, well, I dealt with it very poorly, but um, so for the first twenty years of my life, like I said, I mean, awesome, like no, no real strife. I was ready to take over the world. Like, I felt so confident in our ability to build this business, so excited. And gosh, like two months in to starting Reddit. Fresh out of school, my then girlfriend, who was a year younger than me, she was studying abroad. She had a pretty serious accident, big fall. She was in a coma, flew out to go see her. She survived. She made a nearly full recovery, actually, but the like the first month, two months of Y Combinator was this.

• 48:18Speaker 01

  And you get that phone call and you're like, and again, I was very lucky. I I'd never had a phone call like that before in my life. And you get that phone call and it guts you and you're on the first plane to Germany. And you're trying to just make sense of the world, right? This person you love, this person you care about. And another month or two later, and then I get the call that my mom has had a seizure. And she's been diagnosed with a terminal brain cancer, glioblastoma multiforma, stage four. And those are words you don't want to hear. And, you know, the that that was really the crippling blow where.

• 48:53Speaker 01

  You know, here was someone who, I mean, I had a, like I said, great relationship with my parents, but like definitely a mama's boy. And I was an only child. What can I say? I was pretty cool. But no, she was, she was amazing. And, and the first thing I did when I saw her, so I flew out of Baltimore, first thing I did when I saw her was asking, you know, how are you? How's everything going? How are you feeling? And her first response, first words out of her mouth were, I am sorry. And I was like, what do you mean? You don't mean sorry? And she's like, well, I know you're starting this company. You're supposed to be a CEO right now. You got to focus on Reddit. Don't focus on me. And I know how much of a distraction this is going to be for you. And, and you hear something like that from someone who you love so much, who's already given you

• 49:36Speaker 01

  so much, man. And I thought, I was like, I'm the last person, you should be, you should not be apologizing to me right now. Like, focus on yourself, please. Like, I'm gonna be fine. You owe me nothing. You've already given me everything. And that's emblematic of who she was. What it did was it gave me a confidence. I knew, I, there was no way Reddit would fail. No way. No chance I was gonna let it, no way it could possibly not succeed. Because she, she blessed it with that. She, she really, even in those situations, still, still was looking out for her little boy above herself. And, you know, she fought for another three, four years. She got to see me sell Reddit. It had a lot, not gonna lie, right? You know, in the grand scheme

• 50:18Speaker 01

  of tech, a $10 million exit is, is miniscule. For 16 months worth of work, pretty good ROI. But to be able to make that call to my mom, to say, hey, your faith in me paid off, like, what can I buy you? Was, was worth everything. And then, true to form, true to form, like, I knew I was gonna get my dad some season tickets for our local NFL team there in DC. True to form, though, my mom was like, I don't want anything. I'm like, no, no, I'm not gonna let you do this. Come on, what do you want? She was like, I don't want anything. And I ended up making a donation for her to her favorite nonprofit. She was like, all right, if you're gonna have to give me something, you can do that. And I was so mad.

• 50:59Speaker 01

  I was so mad because I'm like lovingly. I was like, God, there's no way I'm ever gonna top this. Like, you realize you have set the bar so high that if I ever have kids, I'm gonna be chasing that goal. But that, like I said, that's who she was. That's all she cared about. She was a, she was an undocumented immigrant. She was an au pair from Germany who overstayed her visa because she fell in love with my dad, this Armenian American here in the States. Yeah, they eventually got married, had me. But she, you know, she worked the jobs she needed to work to pay the bills and do the things. And her number one, I mean, her, and I think anyone would have told you, the most important thing to her was her family. And, you know, I was an only child, so I got all the, I got all the shine from that.

• 51:44Speaker 01

  But that was the foundation, man. And, and when folks wanna know how or why or all this stuff, man, I, I point to her. Sorry, Dad, you get some credit too. But having that confidence, having that support, having that unwavering. When I told her, I told this woman I wanted to be a professional waiter in high school because I was so good serving at Pizza Hut. So I worked pizza in, in high school and I was a dishwasher, then I was a cook. And then those deep, the, the, the deep dish pizzas are a sleeper. I'll make them at home now with the cast iron. They're, they're good. And, and eventually I, I made it as a serving and I was, I was pretty good. And my boss, Tony, he was like, hey, you know what? Instead of going to college, I think you could do this full time. Like, you're really good. And I was like, really? And he was like, yeah.

• 52:29Speaker 01

  And I was like, I could move to New York. And he's like, you can move to New York. You can make a great career out of this. And, uh, and so I remember going home and telling my parents. I was like, I'm thinking about not going to college. And the last thing you would tell an Armenian dad is that you're not gonna go to college, just to be clear. And my dad, to his credit, didn't say anything. My mom, though, so sweet. She was like, look, whatever you do, I know you're gonna be the best at it. I know you're gonna work your hardest. Why don't you start with a budget and figure out what it'll cost to live there? And then how much you'll get paid and see if that's something you wanna accomplish. And thankfully, my ADD brain switched pretty soon thereafter. But like, this was a woman who, no matter what. Was gonna support whatever I was doing. And then when it just so happened to be a tech startup,

• 53:11Speaker 01

  she was like, great. She, literally the first person to buy our merch, the first person to post on, God, there are comments from my mom on TechCrunch circa 2005 that no one else would notice, but I know because I can see her username. And, and it's the most like crazy German mom English you can imagine. But uh, it's the sweetest thing. And like, she was a ride or die. And so that was the, that was the bar I had. And so even when those things came up, I just knew I can't quit. Now, here's where I [__] up was, I mean, intense compartmentalization. And it was what I felt I needed to do at that time,

• 53:53Speaker 01

  which was let me just use work as therapy. Let me just work my ass off because I cannot work anyone. And if I've got her pulling for me, I will crush any competitors. I know my co-founder wasn't really equipped to have those conversations or, or really be a support at all. But, I mean, we were kids, right? And so I just decided work is the therapy. And for the next 10 years, you know, really did not think about explore delve into anything other than I'm just gonna do my work and I'm gonna, obviously, I took as many Airtran trips home as I could to spend time with my mom and dad on weekends, but like, let me not go any deeper than, yeah, here's this shitty

• 54:37Speaker 01

  thing. I'm gonna compartmentalize it and just focus on the tasks at hand. And there were areas, look, I, I think compartmentalization gets a bad rap. I do think there are areas where it's actually tremendously helpful. But with some, now my, my, my take is a little bit more nuanced, where I think with some work, it's good to go into the box, to rearrange some stuff, to sort through some stuff, to organize it. But it, I, I actually think there is a value to having some stuff in boxes and to compartmentalize, because I also don't want to spend my days. Like reliving and rehashing and re- just analyzing those experiences, right? I'm not doing her any favors, right? Her greatest joy was seeing me be successful as a CEO, as a startup founder,

• 55:21Speaker 01

  and whether it was Reddit or anything else, that's what mattered. And so it's a shame, right? She hasn't gotten to see me get married. She hasn't gotten to see me have kids. She hasn't, she'd have been an amazing grandmother. She hasn't gotten to see me build a lot of businesses I've built. She's saw me, though, live my dream. And when I decided it was time to build my own venture firm, I took the lessons from those days of Y Combinator. Because Jay, I agonized over a $200 plane ticket on Airtran to Baltimore because we only had $72,000 in the bank. We didn't raise that much money. This is a very different era. But even if we had raised a normal round, today would be maybe a few million dollars.

• 56:02Speaker 01

  I still don't want a CEO deciding, God, this is gonna hurt our burn. Do I really want to take that trip? And we built a program in 2776 specifically to say there are tens of thousands of dollars a founder can use that we are paying for. It's coming out of our fees for their wellness, their development, any caregiving needs. Like, we've had founders use this to pay for a babysitter and a date night with their partner. Awesome. We've had founders use it for, you know, therapy, for executive coaching, for surfing lessons, right? If it helps them find their focus, find their balance, be better founders. For early-stage companies, that's often the entire business is the founder. And if Y Combinator had had a program like that, I think it would have made all the difference.

• 56:47Speaker 01

  And it's not to slight them. I don't, they didn't know what they were doing. They were building the firm for the first time. But I want to do 776 differently. And not because it feels good, but because I actually think it will drive better outcomes. It will mean better leaders, better managers, better founders, which will lead to healthier organizations, which I think will lead to more returns. And these are the ways that we're trying to learn from those experiences. And I speak with founders to this all the time, especially at the early days. But it never goes away. But especially at the early days, so much of the company takes on your neuroses, your, like, you are setting so much of the culture and don't even realize it. Even just the way you show up on a Zoom call, right? Because you're the founder, you're the CEO.

• 57:29Speaker 01

  Like you are dictating so much of how other people are going to move. And once you repeat those behaviors over and over again, what you've done is created a culture intentionally or not. And so your baggage, your challenges, the things that you're not addressing and working through to be your best are going to be inherited by your team. And, and that's, again, none of this is, this isn't, this is the soulless capitalist talking here, right? I think there's a, there's a fantastic emotional argument for it and a health argument for it. But I always try to come first from just the business argument, because if it makes sense for business, then it's a no brainer. Then obviously, if it's going to be for your health and wellness and development, then you should do it. But, but I do think it has a bottom line impact.

• 58:10Jay Shetty?

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• 58:55Jay Shetty?

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• 59:14Speaker 05

  Mr. President, my company tore me of the explosion on our rig on October 2nd. Causing massive water displacement and triggering a tsunami. They all heap the blame on me. Tom Cruise is.

• 59:25Speaker 03

  Digger got us into this mess, and Digger's gonna dig us up. From the director of Birdman and The Revenant.

• 59:31Speaker 06

  What would happen if I stopped doing it? You stop, you freeze to death, that's what.

• 59:35Speaker 07

  With great power comes great deniability.

• 59:38Speaker 06

  I'm not the first nanny.

• 59:40Speaker 07

  Digger, see the trailer online, only in theaters October 2nd. Rated R, under 17, not a middle without parent.

• 59:44Speaker 01

  What was the behavior you saw in yourself that?

• 59:48Jay Shetty?

  You had to readdress or check yourself that you felt was seeping into the culture in any of the companies you've been.

• 59:54Speaker 01

  Oh, I got that. So here, I'll give you an example that'll illustrate it. So like two years into Conant asked, when there's the meme in the Silicon Valley show of resting, investing. So normally when a founder gets acquired, they just hang out at the company and just they don't do anything and they earn out and they leave. But again, not me, crazy. So like, I want to keep shipping. I want to keep building things. And instead of actually making the case for the engineering team to go and build, in this case, it was a mobile app. So if you can believe it, in 2009, 2010, there was this new thing called the iPhone. And some people were talking about how it was going to be the future of computing. Now, I was one of those people who hook, line and sinker was like, this is a big deal.

• 1:00:37Speaker 01

  And if we're building Reddit to be like the destination for what's new and interesting on the internet, we need a mobile app. Now, engineering team did not agree because the way things had always worked, it was fine on the browser, it worked great on the browser, the company was growing. Why change it if it ain't broken? And instead of doing what I should have done, which would have been better leadership, which is actually bring folks in, win them over, make the case, get the buy-in, and then change the product plan. I just hired a freelance team to go and build it because I made a half step of an effort to make the case and do the right thing as like a mature manager. And when I wasn't getting the progress I wanted, my impatience and my relentlessness was like, we're just

• 1:01:20Speaker 01

  gonna, I can hire other people to build it, we'll just build it. And it worked. We shipped it. Reddit had a mobile app called iReddit. And it was doing well. I was really happy with that pun. I hope, I hope people would say I read it on Reddit. I don't know if anyone's ever said that. That was the hope. But then a year later, I leave. You know, the handcuffs had come off and fully vested. And then what happened? The app died because there was no one left to support it. And there was no institutional buy-in. And so imagine four years later, five years later, I come back. And now it's 2014. And everyone knows you need a, you need a mobile app. You have to have a mobile app. And the culture of Reddit is still solidly, desktop is only what matters. Why do we need a mobile app? And I'm like,

• 1:02:01Speaker 01

  I failed. Like I failed. We had this five years ago and yet here we are and we actually need now need to do it right this time, actually get the buy-in, actually bring in the folks, actually finally shipped it out probably a year later. But it's that. So it was an unwillingness to actually lead and it was a relentless desire to just keep moving forward with or without an actual team. And that is a terrible way to be a CEO. Terrible. It's something frankly, I think I still struggle with in a lot of ways. I will never be hanging out on a beach. I will

• 1:02:39Speaker 01

  never retire. I love the work that I do. Yeah, if I do it well, I get very well rewarded for it and that helps. But it's not about that. I love the work that I do. It's very satisfying. It's it's something I genuinely would want to do all the time. And my wife knows this and you know, she's someone who knows a thing or two about relentlessness and hard work. But even she would admit and has has said on numerous occasions at the dinner table that like there's sometimes I take it a little too far.

• 1:03:11Jay Shetty?

  No way.

• 1:03:12Speaker 01

  Swear to God.

• 1:03:13Jay Shetty?

  Wow.

• 1:03:13Speaker 01

  And I actually had I had an LP. So one of our investors, so about 10% of the money we invest out of seven seven six is my money. But then 90% of it is from institutions, universities, all values aligned, good folks. And I had one of our LPs casually be like, oh, hey, I heard you were or I saw you were at the Olympics. Looked like it was a lot of fun. And I was like, are you implying that I was just hanging out at the Olympics for two weeks? And he's like, no, it's the summer. I totally get it. Like, it's fine. But and I as I was retelling this story to my wife, and she's like, I will literally call him up because they know each other. It'd be casual. And I will assure him that I have countless times complained about the fact that you're working too much. And I'm like, baby, from any any partner, that would be powerful.

• 1:03:57Speaker 01

  But coming from you, right, it carries a lot more weight. But the reality is, I love this. And unlike being a professional athlete, right, I get to do this forever. As long as my my brain's working, right, I have compounding that I get out of age and experience. And it's the unfair advantage of all of us who are not professional athletes is that we actually continue to compound the expertise over time and get to keep doing the thing that we loved in our 20s, in our 30s, in our 40s, in our 50s. And it's a great blessing. And so Yeah, I have this and and I think the downside has been historically making sure I was either. I was building teams and building organizations that were aligned with this and and that was a big part of the decision four years ago to say, okay.

• 1:04:42Speaker 01

  You know, Caitlin, who I founded seven seven six with, she had joined me early in the Reddit turnaround almost, you know, that time was like six years earlier. I know she's got the same whatever brokenness, that relentlessness, that hunger. And and having a partner like her and then Lizzie, who also came over, now she runs my foundation. Those are the folks I just want to spend the rest of my years building with and working with, and that's not a judgment. Like, y'all got to find whatever you need. And and I think one of the things that always gets so twisted, because I am, look, hashtag business dad. I'm out here making pancakes every Sunday for my girls. I do crepes on Saturdays, I post it on social. Yes, I've gotten into smoking meats lately and I'm very proud of that.

• 1:05:25Speaker 01

  But like, like all things in social media, you're seeing a curated version of the things. But the promise that I made to my kids is the same promise I make to my team, which is like, I'm sorry to my childhood friends. But I'm like, when I'm on the clock for work, I'm going to show up here the best way that I can. When I'm on the clock for my family, I'm going to show up there the best way that I can. And that's frankly, all the bandwidth I have in my life. And I I think one of the areas I I should be investing more into, and maybe there'll be a time. But it's the relationships I have with other men. And and these are the guys, I've known them since I was five. These are my best friends, we're in the group chat daily. We see each other now maybe once a year, twice a year, but I, and you know, I got to organize it.

• 1:06:10Speaker 01

  I organize a really proper guys trip at least once a year. Now we've added a second one, but those, that's the one area where I know I've made a a sacrifice. And I've just said, look, this isn't a part of the equation anymore. We used to play video games all the time after school. We get off the bus, we go to Mike's house, fire up Goldeneye and sixty four, wouldn't do my homework. And but that's a, that's chats in my life that's closed and now I have to make these trade offs. And so when I always get a little miffed when people twist it as like, oh, this guy's not that serious. And it's like, no, like. There is nothing wrong with caring about being the absolute best at work and also for your family. Those things should not be mutually exclusive. And I don't know how we created this myth that it had like, yeah, it sucks. There's no such thing as balance.

• 1:06:55Speaker 01

  You've got to figure it out. You're always never doing enough. But hell, modern women have had to endure this for quite some time now. And, and I think only recently has it come up for dads. But I'm glad it's getting talked about more. And I'm fine with the juxtaposition.

• 1:07:11Jay Shetty?

  Yeah, absolutely. I mean, I feel like that lack of presence bleeds into the other area anyway. So if you're at work and you're not present, you can't suddenly be present at home.

• 1:07:21Speaker 01

  Yes.

• 1:07:22Jay Shetty?

  And if you're absent at home, you can't suddenly be present at work because our mind doesn't have an on and off button that just switches on and off as quickly as that. And so hearing that makes a lot of sense to me. Why, why are those male relationships so important to you at this stage? Like, why are they valuable? And why does it feel like there may be a time where they're needed? Like, what would they serve you with? Like, what, how would that help you now?

• 1:07:46Speaker 01

  Humility. I mean, these are the guys you still like, they'll give me shit all day long. And that's great, because I need it sometimes. And it's, it's helpful. Also, knowing these guys for as long as I have, it's 100% genuine. And you see it, right? Like, you get, as you find success, as you find fame, as you find wealth, there's a difference in the, the relationships. There's always this like, is a little bit of a raised eyebrow, right? And I, I know how, or I've seen how isolating that can be for folks. And I've never wanted that for me. And one of the things I've always appreciated is that these guys have been my best friends, like I said, since I was a kid. And when we get

• 1:08:30Speaker 01

  together, you know, the only thing that's changed is that we're older, we got some, we got some money now, but like, we're, it's the same bullshit. And they treat me exactly the same way. And like I said, it's a good, humbling thing to have your friends talk shit to you on the group chat. I think male companionship is underrated. And

• 1:08:51Speaker 01

  Like I said, it's the one area where I know I could be doing more work. The challenge is a lot of us have young kids right now and that again is the priority. I think, I think it'll shift again when I've got teenagers and they no longer want to hang out with me.

• 1:09:04Speaker 01

  But all, you know, almost all of us have kids that are young and we get it. We'll bring, we'll bring the gang together, but we live in different places and it is what it is. And then candidly, one of our guys, Adam, suddenly had a heart attack and he was training. He was the most fit out of all of us. He was at the gym, his heart gave out and, and he passed on the way to the hospital.

• 1:09:26Jay Shetty?

  Oh my gosh.

• 1:09:26Speaker 01

  And, and then again, you get that fucking phone call and you're just like, no, this is a joke. Like, there's no way, no chance, no chance. And that was a wake up call for me. And, you know, he didn't have children, but we're all looking around each other at the funeral. And again, a lot of us with kids just thinking like, Christ, like we, we have to show up in such a big way for these little humans. And you can't help but take it to that selfish place, right? And be like, I deeply miss this guy. And I feel like I owe it to him. Like I said, he was the most fit out of all of us, this dude, CrossFit and I mean, uh, and Adam was, to his credit, too. Man, the guy always was down. It did not matter.

• 1:10:10Speaker 01

  It could have been, let's just go see a dumb movie on a Tuesday night. He always, always was a strong yes. And that mindset, and this is something I always try to take, and I've tried to tell founders this too. Like, it's not my quote, but it's the one about the average of your five closest friends. And, and I think a lot about this because like, you know, my, these guys, we've all had very different lives. There are, I don't know if I'd start a company with any of these guys, but there are attributes about each one of them that I find really remarkable. And those are the things that I keep in mind when I'm like, one of the reasons I love staying close to you guys is I, I care about you. I love you. Like we've known each other through so much, we've.

• 1:10:53Speaker 01

  I we've done a lot together. We've experienced so fucking much and and there are still parts of you that just make me want to get better. And for Adam, it was the relentless commitment to his health and fitness. And and I just I I couldn't help but thank God, I really got to get my life right. And I started with the whole battery of tests and like, I'm getting blood work, CT scan, doing all the heart, like everything I can now, and really rigorously, I'm not a not a hypochondriac, but I'm like, I need to get some baselines. I need to be checking up on this. I need to actually be like making like thoughtful visits to the doctor fairly regularly. Because like, and as a dude, you're just like, whatever

• 1:11:36Speaker 01

  you the culture's put some dirt on it, and you're fine. And like, that's how I lived for 40 years. And and that was the wake up call. And I feel like I owe it to him. And so when I get up in the morning, and, you know, I'm like, okay, drag my ass to the gym. I'm like, come on, show up. Keep going, man. Like, do it for Adam. It's a thing where now it puts a framing on all the times we get together, because we know at some point it'll be the last one, that someone is going to be there, could be us. And and so again, we're not, I mean, look, we're still doing the same dumb shit, like we were at a brewery in Baltimore last time. Like, it's not, we're not that sophisticated about it. But I'll tell you what, though, we've gotten a lot smarter. As we've gotten older, I think we

• 1:12:20Speaker 01

  have gotten a lot better telling one another actually how we feel, which is, again, this is a nuts thing for, you talk to my 20 year old self, like, would you imagine yourself having like thoughtful conversations about like, life with your with your guys? And the answer would have been, no, of course not. Like, we're talking about football or video games or girls. But but that's been a nice part of getting older is now there's more depth to this relationship. Like, we have true, true trust and intimacy. And we have this feeling like I can, I can literally tell this person everything, because he's seen me at my best and my worst. And like, this is my boy, right? And that unlock gives me something that powers me up for, you know, however long it is until I see them again.

• 1:13:05Speaker 01

  And when I think about what is missing right now, I think about all of the young men who don't have

• 1:13:14Speaker 01

  Great role models and can now access any role model they want. But they are going to default to the junk food. And that's not a judgment. It's the same reason I really want to pick up the Snickers, right? Instead of whatever the better choice is. There's an intellectual version of that junk food that exists, which is not nourishing. It's not actually helping you grow. And, and it's trying to fill a void. You have a hunger for this thing. And I think men in particular, the shadow of all of the emphasis being put on women is that so little attention has been put on our young men. And I would love to see not attention taken away, but more attention found to be placed

• 1:13:58Speaker 01

  on talking about young men, supporting young men. Because, and, and there have been, I was a, so I was briefly a Kiva fellow. So I volunteered for Kiva when I left Reddit the first time. So I was in Armenia, working with entrepreneurs and it was amazing. One of the lessons they take away from that is women entrepreneurs anywhere in the world are a far better investment than men. Because the money that you invest in them, that they use to help build a business oftentimes gets reinvested, more often than not in the family, in the community. Versus if you do it for men, some of the money goes to the family communities, some of the money goes to the local bar, local establishment, whatever, like basically investing in women in emerging economies just has a bigger impact on society. And it kind of tracks.

• 1:14:43Speaker 01

  It's a generalization, but I think we're sitting here going, yeah, okay, that kind of tracks.

• 1:14:47Jay Shetty?

  Makes sense.

• 1:14:48Speaker 01

  But then you go a step further and it's like, okay. Under duress, and this is closely related, women tend to endure a lot better than men. And this is one of the reasons why when you look at prisons, you look at terrorist organizations, you, you look at when people are pushed to extremes disproportionately, men that end up. Not turning out well. So I think we have an imperative here where if we have a generation of young men who are feeling disillusioned, who are feeling demoralized, who are feeling this insecurity, this deep, deep, deep pain, like, we all have an incentive to make sure that they're getting that high protein diet of things that will actually help them be better and actually give them a path towards self-improvement and give them a path towards

• 1:15:32Speaker 01

  being successful, viable members of society. Because unlike women, they're not going to handle that well. And so I can make the case from a like a value standpoint, like, hey, I think it's important to support these young men. But I also would make the case just from a societal standpoint, like, it is in our best interests for for public safety, for all the things, to make sure we get those sort of that generation back on track. And I think it starts with conversations like this between high profile men who've had success in their careers, who can talk about and normalize a lot of this stuff. Because at the end of the day, if we don't have those examples, what else fills the gaps? And I don't like the alternatives that fill in the gaps. And what's wild is, you know,

• 1:16:17Speaker 01

  I didn't really have, I very much broke into tech and business and learned a ton. And every time I keep going up, and I tell the guys this all the time, I keep leveling up, right? And I keep meeting new people and sort of getting another peek behind the curtain of like, how the world works, or how business works and all that stuff. And it's been eye opening, because like, their shit, I would, if I just could tell my 15 year old self, be like, don't do that, that's stupid. Like, there's actually a smarter way to do that. And I hope to always keep feeling that to some extent. But as I keep doing that and keep meeting more and more folks, I have yet to meet one who doesn't have this level of introspection and depth. And it's, I'll tell you, it's most telling among the billionaires

• 1:17:00Speaker 01

  who are now grandparents, men who have achieved everything you could hope for in business, doesn't matter the industry, who are looking at their grandkids as a second chance, because they didn't get to, or didn't want to, or weren't interested in, or whatever we want to call it, spending that time with their own kids, and they're so grateful for that second chance. But I keep looking at all these stories from men who I really, really, really respect. And the ones who feel like they've had the most fulfilling life, all keep coming back to human experiences they have with loved ones, with family. And like I said, I got a Much smaller scale version of that with my own mom who who never wanted for anything.

• 1:17:42Speaker 01

  And when you get to spend time with folks who have a few years left to live, it becomes very telling, especially to do it in my twenties, full of all that youthful vigor and vulnerability, to get humbled and see someone who does not care for anything other than the experiences she had and the humans she loves. Bro, I, that was probably one of the greatest gifts she could have given me was that perspective. So that when I did find wealth, when I did find notoriety, I'd be lying if I said it doesn't affect me in some ways. Sure, it affects me, but I have never, never gotten it twisted about what actually mattered. And I've never wanted for notoriety or fame. I've never wanted for wealth. I've wanted for things that helped me get more time with

• 1:18:25Speaker 01

  the people I care about and make me feel like I'm living a fulfilled, like a fulfilled and purposeful life that's providing value to people. And that was a gift she gave. And so, I don't know, the more that we can normalize this stuff, especially among folks, and I say men in particular, but all people, but especially men who have reached the highest levels, I want that 18 year old or that 16 year old, that 12 year old to be watching or looking going like, hey, all right, these guys are talking about stuff that feels like it has substance, it has meaning, it has purpose, and they're still the ass kickers in the day job, whatever it is across the industry. Like, these things are not mutually exclusive. And I just, I want to see more of those voices like yours get amplified because it's, I think it's very, very important.

• 1:19:08Jay Shetty?

  And I love that, what you said, that juxtaposition, again, the ability to be a killer in the workplace, a brilliant leader, a powerful individual, and at the same time being able to be empathetic, compassionate, vulnerable, that, that's the, that's, the power is always in the juxtaposition, right? You look at it in anything, whether it's a community, a company, an individual. And I think a big part of that, going back to what you've been talking about, is also seeing men's relationship. With their wives.

• 1:19:35Speaker 01

  Hmm.

• 1:19:35Jay Shetty?

  Like, I think that's a big part that for years, when we were talking about the lack of role models or the lack of the ability to look at someone, it sounded like your parents had a wonderful marriage and

• 1:19:45Speaker 01

  I lucked out, man.

• 1:19:46Jay Shetty?

  Yeah, and demoed a beautiful connection in front of you that you got to see with you and your wife having such busy lives, having priorities, both of you professionally, partnerships, places to be, travel, and then you've got kids. How have you found a way to prioritize each other with the million things going on?

• 1:20:09Speaker 01

  That is at the crux of, of I think, every conversation we ultimately have as a couple, which is, it's funny, I'm very, obviously, high-tech, she's very low-tech. Um, sometimes it literally comes down to calendaring and making sure, like, if I had my druthers, it would all be digital. Um, I finally got Serena to modernize a little bit and now we have a giant, um, like a dry erase board calendar that sits at the dinner table where she'll put in her schedule. And then I have to go and usually I'll take a photo of it to send to my admins.

• 1:20:46Jay Shetty?

  Yeah.

• 1:20:46Speaker 01

  And then we'll write in mail, but at least we have one shared space where we know, like, okay, Papa's out of town for this business trip. Mama's going to do this thing. And it is the hardest thing. Um, it is explicitly creating date nights. I mean, it's funny, it's the same tactics that you'd hear any couple talking about with a therapist about, like, hey, what are the ways to keep the relationship going, the romance, all that stuff? And it, it is definitely amplified in all kinds of ways with a higher profile relationship. But the other reality is, so Serena's been working since she was a kid, right? Like tennis was not, I mean, it is a sport, but like, it's a job, right? The amount of hours she was putting in.

• 1:21:27Speaker 01

  The responsibility, as soon as she started like playing, like playing, playing, tremendous responsibility. So, you know, I'm married to someone who has been working for thirty five, thirty six years. And who had a childhood, and I think Serena would say, like, was a great childhood, not a normal childhood. But now she's evolved, her word, into, you know, she's still got businesses, just launched this beauty brand, Wynn, shameless plug. Uh, great brand. And, and so she's still doing business things, she's investing. But she also loves, I mean, she's her class, she's the classroom mom for Olympia.

• 1:22:07Speaker 01

  She gets to spend so much of her time now being an active and super engaged mom for her kids. And I, I can't help, and I've told her this too, can't help but feel like this is a chance for her to, she's on the other side of it now. But to live that life that she didn't really have, which was, you know, where your number one job as a kid is just to go to school, learn things, hang out with your friends, and who knows if Olympia keeps going with the tennis or the golf, we'll see. But, but she's relishing that opportunity. And so that helps me a ton. Because, right, that's ironically, that's the thing that I grew up with, the boring, typical suburban lifestyle,

• 1:22:47Speaker 01

  that most people in my position, myself included, will spend a lot of their lives trying to maybe not get or run away from because they want something else. And yet here she is, having gone to the top of the mountain, achieved everything, and that's actually the thing she loves most. And so how we make it work, it's all, it's the banal stuff. It's the like, making sure we prioritize, it's trying to figure out and also decoding the differences. Um, obviously, we're an interracial relationship. I don't think that'll surprise anyone. And as a white dude, married to a black woman, you have a societal gulf, right? Between this, in terms of the ways we've experienced our lives, right?

• 1:23:28Speaker 01

  The, in the American hierarchy of things, like, you know, we have very different lived experiences. You set us out, obviously, the fame, notoriety, queer stuff, but like, even if we just operated this life as two random people with our makeups, we'd have very different points of view, experiences, all that stuff. And it's probably the

• 1:23:50Speaker 01

  Hardest and best element to the relationship. Where like the table stakes are, we love each other. We've made two incredible humans together. We will do anything. I mean, believe me, the two. She, I, she jokes that I'm like the psychopathic dad. Like, there's an Armenian dad meme in here, by the way. Like, we're very protective of our kids. But she's super mama. So like, we have things that we care so, so deeply about, that we know we're on the same team for. And so it's probably the best way of all the ways to be checked on. Yeah. Like, a blind spot, let's say. It's best to have it come from someone who you know cares so much. And that's where the growth happens. That's the tension.

• 1:24:35Speaker 01

  And so like, if I say something or do something, and again, nothing crazy here. But like, if I say something or do something and she's able to shine a light on, be like, hey, did you notice, blah, blah, blah? Or, hey, this is like, bringing up these things to help me have better awareness. Because, look, I got two black daughters. I want to make sure I'm showing up the best way I can for them. It helps because I still feel that pain because I'm like, I'm not a racist. I'm not a bad person. But then you sit with it for a second and you're like, okay, just hear, hear this feedback, right? And, and it reminds me, it's just like going to the gym. You're pushing some weight. And you're trying to get to that next level. And it's gonna hurt because that's where the muscles tear, but that's where it grows back stronger.

• 1:25:19Speaker 01

  And so I feel the same way when I take that. I'm like, ah, okay, fight the impulse. Don't be defensive. And just listen and hear and try to understand. And, and I will say though, it's, and I've talked to other folks in interracial relationships. It is definitely, there's a dynamic there that creates new challenges. Or even I think any cross-cultural relationship creates those challenges, I bet. I don't know if I was, I guess I'm a weird mid-Atlantic guy. But the difference between me and even a white person from Appalachia is gonna have those cultural challenges, right? But across those lines, that's where you get, again, with a relationship built on love. You get this opportunity to say, okay, like, let me try to learn and try to be a little better. That I think helps.

• 1:25:59Speaker 01

  But like I said, it's probably the worst part is the dynamic. There's a reason we live in the middle of nowhere, Florida. Like, I love being here in LA, but like, I think we live in such a weird culture.

• 1:26:16Speaker 01

  That, you know, the celebrityization of things is just, it's different. And, and one of the things that we always wanted for our girls is for them to have, I mean, they're not going to have a normal life, but to not be living in it. And, and to have the ability to do that from, you know, sort of the middle of nowhere, Florida has been probably the biggest secret weapon.

• 1:26:37Jay Shetty?

  What did you, what I love though is the awareness you have of the upbringing you had and how that's impacted you now with you wanting the opposite. And how the upbringing she had. Yeah, and I, and I love that awareness because it's such a subtle point, but it's such a powerful one because it sounds like you both accept why you're wired the way you are. Because I think it could be really tempting to project and hope that, well, you know, Alexis has achieved everything too, so shouldn't we both just let everything go and just be home with the kids? Or you to be like, well, you've achieved so much, we should just be going for the next mountain.

• 1:27:17Jay Shetty?

  Like, which, which I think we do a lot with our partners where we reflect what stage of life we're on. Like, I remember when my wife and I first met, I was ambitious and driven and she was definitely the homemaker and curator and, and then as I've become more set in my world and have more time, my wife's career is like really taken off and she's really found her purpose and it's amazing. But I just love watching her flourish. So even though I have more free time to be able to spend together now than I did eight years ago, I recognize that watching her grow and watching her thrive is actually the most inspiring thing. And now that just because I have more time doesn't mean she has to adapt and adjust around that.

• 1:28:02Speaker 01

  I love that.

• 1:28:03Jay Shetty?

  Yeah, I find it's a really, but, but it's such a common thing I see where it's like, I wish you were at the stage of life that I'm at. And that seems to be the hardest, most impossible thing to demand.

• 1:28:13Speaker 01

  You know, the challenge I had in previous relationships, the, the general theme was.

• 1:28:21Speaker 01

  I knew I was super ambitious. I was very upfront about it.

• 1:28:26Speaker 01

  But it still doesn't really land until three months in, six months in, nine months in, and you realize, oh, this guy is not going to change.

• 1:28:32Speaker 06

  Yeah.

• 1:28:33Speaker 01

  And, and it seems like a fun thing for a little bit. And then at a certain amount, like eventually push comes to shove and, and it, and there's a gap because they didn't get it. And, and I, again, I, I don't think that's a right or wrong here, but it's a, it's an incompatibility.

• 1:28:49Speaker 06

  Yes.

• 1:28:50Speaker 01

  And part of what attracted me so much to Serena was the fact that I knew we would never have this conversation about like, well, why do you have to do this thing? Or why is this so important? Or like, why, what do you mean you have to get this done tonight? Like, that could never happen because of everything she had to do in order to achieve the heights that she had gotten to. And so that to me was already very appealing because I was like, okay, this is table stakes. I have found someone who has clearly even more ambition than me, who has achieved so much. And in a way, so I don't know if I'd say the same thing if I were an athlete. I think that might've been harder. But to be with someone like Serena, right? That's like

• 1:29:33Speaker 01

  literally one word. Like you, you don't even need to say her full name. It is tremendously liberating because I know, and also because of who we are and where we come from, Jay, there is literally nothing I could do. I could, one day, God willing, I will be a billionaire. I, I will never run for president, but let's say I could be a billionaire who runs for president and I'll still be Serena Williams' husband or Serena's husband, right? I could be, I could, I could be an astronaut. It doesn't matter. It literally does not matter. And, and part of that is a testament to like where she started, where she got, what she did, all those doors that she opened, all those things. And so in a way, it's kind of liberating as a super

• 1:30:16Speaker 01

  ambitious person, especially in a society where like, it's a meme just to literally say, oh, that guy is comfortable being called Serena Williams' husband. Now, candidly, if we live in ideal world, no one is anyone's anyone, right? But I do appreciate, I understand why the internet finds that really exciting and interesting. But the bigger story here is the fact that if you have this kind of partnership you're talking about, you're able to let one another flourish at those things at that time when they're ready. And maybe I didn't see it, maybe, maybe I missed out on some great relationships earlier because it wasn't there at that time.

• 1:30:56Speaker 01

  But at the end of the day, one of the best parts, you know, dating Serena while she was winning Grand Slam after Grand Slams, breaking every record, doing all this stuff with Olympia in her belly. I might add, you know, the pinnacle of sports excellence. And then also seeing her now, like making cinnamon rolls for the second grade class. Like both of those things bring me so much joy. And frankly, I love seeing the latter more because it doesn't come with all the baggage of being the public persona that you just have to endure doing that job. And I know she doesn't miss it at all for those same reasons. And I think that's, I don't know, that's been why it's just, I don't know, been, been an easy transition for her and frankly, been a lot of fun to see this, this evolution for me.

• 1:31:41Speaker 01

  How did you meet? Six months into the Reddit turnaround, I was burnt out and my head of comms said I needed to go. She was like, go to Italy. And I was like, what? And she was like, there was a speaking gig that wanted me there. And I was like, sure. I was like, wait, no, but this is a boondoggle. Like, there's no point, we're not ready to, like, win over marketers. She's like, just do it, please. Like, you need a day or two, just go. I was like, all right, fine. I go, I flake out on the conference that first day and I just find a cafe and I started doodling, working on some sketches for product stuff. I meet up with a friend of a friend, very random. They just walked in.

• 1:32:19Speaker 01

  And they're like, hey, can we use the table? I'm like, sure, we'll get some drinks. We're out that night until like three in the morning. And I get home hungover the next morning. I need coffee addicted. Go downstairs. They say, sir, breakfast is over. But if you want coffee, you can go sit by the pool. I go sit by the pool. I take out my laptop and there's a table next to me. The Australian, there's an Australian guy at the table tells me the movie says there's a rat at the table. I say, I'm not afraid of rats. I'm from Brooklyn. I see rats all the time. He's like, I might as a rat. You better leave. And I was like, no, thank you. I'm good. And I was just working. And then the lady next to him turns around. It's Serena and she's like, oh, you're not afraid of rats. Like, no, not if you don't bother them, they won't bother you. And she was like, oh, you're here for the tech conference. And I was like, I am.

• 1:33:03Speaker 01

  She's like, you, you here to see someone speak in particular? I said, no, I'm speaking. She was like, oh, she's like, what's your company? I was like Reddit. And she, she lied. She was like, oh, yeah, Reddit. She had never heard of it. And we started talking and she said, listen, the rest of my team was going to use this table. So can you just move when they get here? And I said, no, but like they can join me and well, I'll just have breakfast. And so exchanged numbers and I saw her play later that night in Rome. And that was the start of it all. So it's breakfast at a hotel, the Cavallieri in Rome. Great breakfast, wonderful truffle omelet. In case you, if you want to get the Alexis special, it's the truffle omelet. It's a great.

• 1:33:46Speaker 01

  Mr. President, my company formed me of the explosion on our rig on October 2nd.

• 1:33:50Speaker 05

  Causing massive water displacement and triggering a tsunami. They all heap the blame on me. Tom Cruise is.

• 1:33:56Speaker 03

  Digger got us into this mess and Digger's gonna dig us up. From the director of Birdman and the Revenant.

• 1:34:02Speaker 06

  What would happen if I stopped going? You start, you freeze to death. That's what.

• 1:34:06Speaker 07

  With great power comes great deniability.

• 1:34:10Speaker 06

  I'm not the first nanny.

• 1:34:11Speaker 07

  Digger, see the trailer online, only in theaters October 2nd. Rated R, under 17, not a minute without parent.

• 1:34:16Speaker 01

  Great omelet.

• 1:34:16Jay Shetty?

  I love it. Alexis, it's, it's, thank you for sharing that. It's, it's beautiful to, you know, just even how you're speaking about your wife. And again, going back to that point, we were talking about having positive conversations in that way of, you know, what a healthy relationship looks like, challenges, ups and downs, difficulties, of course, with any relationship, but. You know, one of the things that I wanted to ask you about that before we get to the end of our conversation is this idea. I mean, you were very humble a few seconds ago, and it's beautiful to see you have reached, you know, you've created something that in and of itself is a word, right? Like, it's like Reddit is recognizable, used, it's in

• 1:34:59Jay Shetty?

  pop culture, like, it's everywhere. Like, you've built something that is fully recognizable, let alone recognizable, just everyone knows what it is. And then Serena has this incredible success, of course, no need to explain. How do you both think about defining success for your kids? And the pressure that obviously will naturally sit on them with whatever they do? And then how do you think about defining success towards your futures as well, together and as individuals? Because you've both had and experienced so much success.

• 1:35:33Speaker 01

  Um, with our kids, it's the cliche, you want them to be happy, productive members of society. I mean, that like, I'd say the other wrinkle I'll put on there, and I tell Olympia this all the time, and I will tell Adira, again, she's just one, but she's doing her best. She's an active kid. Yes, at six, I'll sit her down. But like, whatever they want to do, I have zero tolerance, I should say, we have zero tolerance for them not trying their absolute best. Again, I know that seems cliche. Like, I don't even let Olympia say can't. We'll see how long that lasts. But I will not let her say can't. If she says can't, I'm like, what was that? We don't say that word.

• 1:36:13Jay Shetty?

  I like that.

• 1:36:14Speaker 01

  Because I don't, I don't even want her uttering that she can't do a thing. Like, you can choose not to do it, but we don't say that word. And I try to reiterate to her, I want her to love the act of trying. We used to do, there's a YouTube channel, there's a few actually, that'll do these drawing classes. And I'm pretty good drawing. I made the Reddit logos new. I draw pancakes. And during COVID, I was like, hey, we're gonna do drawing class, Papa can do our class. I can do math and English, but art's more fun. So we're gonna do our classes together. And, you know, early on, she'd be like, wow, Papa, you're really good at drawing. And I'm like, do you think I was born this way? And she was like, maybe. And I was like, no. It's like Papa practiced, Papa drew a lot.

• 1:36:58Speaker 01

  And I want, even for mundane things like, hey, we're drawing Princess Peach. I desperately want her to take only one thing away, which is even the stuff you think your Papa is great at, he sucked at when he started. Even the things your mama is great at, maybe she didn't suck at when she started, but like she had to learn. She was bad. She had to get better. You might have some natural inclinations here and there for different stuff. But I want to see her get comfortable with failing and struggling and then improving. Getting her into golf has been open. I had never played golf. But Uncle Tiger gave me some clubs for her. So I was like, Olympia, you gotta play golf now. And we go to lessons every Sunday.

• 1:37:38Speaker 01

  And that actually has been a great sport for humbling and for getting her comfortable with the process, because it's such a brutally hard sport.

• 1:37:46Jay Shetty?

  It's the most patient.

• 1:37:47Speaker 01

  And you have to get comfortable with failure and messing up. And she'll still, it's funny, she'll whack it 100 yards. I'll be so proud of her. And then she'll totally whiff on a ball. And once she got so upset, she almost, she almost pulled the Serena. She pulled the club up and was about to smash it. I was like, Olympia. She casually put the thing down. I was like, oh, you got that Serena in you. But you see that and you see she's got that tenacity and she is so hard on herself when she doesn't get it right. But I need her to sit in that and soak that up and get okay with it. So that whatever she does, again, if she, it changes every week. Veterinarian, fashion designer, right now she wants to be a singer. I'm like, I don't care what it is, you just need to know.

• 1:38:29Speaker 01

  I'll, like, you love that Beyonce video? How many hours do you think Beyonce spent rehearsing the dance moves? Rehearsing that song, singing over and over and over and over? Like, do not get seduced. And it's crazy. I, I don't know. I did not have anyone like sit me down and tell me that explicitly. And maybe it just ruins, maybe it just ruins life, we'll see. But I need her to know anytime she sees excellence, the only reason she's singing is because of countless, countless hours of trying and failing and practicing that led up to it that no one saw, that no one cared about. And you know, with her mom as an example, she's got the goat of a role model. And she does do tennis now twice a week. I think.

• 1:39:12Speaker 01

  I mean, she's got some good athletic genes, let's be honest. No, but she might, I don't know. If she plays sports, the good news is her mom will be able to have a conversation with her early on about just what it's gonna take. And if she wants to do it, God bless, we'll support her, you know, I, but I, I'm not worried. It's weird. This is not a thing. Okay. When I was a kid, I used to be pretty, I don't wanna say anti-rich people, but like,

• 1:39:38Speaker 01

  I, I distinctly remember going to UVA and I went to some good public schools in Howard County, Maryland. Like, they were fine themselves, but I got to, I played football with kids who had free lunches and kids whose parents were lawyers. So I got exposed to a pretty decent range of kids, which was great. And then I got to UVA and I finally met like rich people. And I was so excited because I was like, these kids are so soft. I was like, this is gonna be great. Like, this is my competition. Like, this is phenomenal. And, and it tracked, but I, now I'm like on the other end and I'm not trying to, it's not for sympathy here. But like, I, there is, I am much more appreciative of the challenges that wealthier families have.

• 1:40:22Speaker 01

  Making sure their kids have, have it, have that grit, have that, whatever you wanna call it. And so that's something we're acutely aware of and mindful of and hoping for. And like, I, like I said, I want Olympia to work either, it's gotta be either a retail job or food service, like some kind of service job for sure, like high school, like it's good enough for Papa, it's good enough for you. Like, I need you to experience these moments and feel some kind of connection. Like, you're gonna have, you're gonna be fine, right? But I need you to be a productive member of society. I need you to be a good person. I need you to know the value of a hard day's work. And, and like I said, it's a weird thing to navigate. Obviously Serena doesn't have any kind of equipment for that.

• 1:41:06Speaker 01

  And, and everything her parents put up with in order to give her that life, like, it's, it's a wild perspective, but that's, it's something we actually think about and talk about quite a bit. And the good news is, you know, at least Olympia, Adira, Adira's fun too. They're tracking to be good humans, uh, which I feel like is number one. And then if they can be good humans who are also productive members of society, like, I feel like we're living the dream. But there is that part of me that just thinks, like, you want, You want to create just enough of that strife to create that resilience and that ability to thrive. And it's so ironic, because if you look at so many of the stories of excellence, there's

• 1:41:46Speaker 01

  always some version, there's some part, there's something that happens that creates it. And it's usually strife. And so it's like, on the one hand, you don't want to, like, part of the reason you did the thing was so that your kid wouldn't have to endure the thing. And yet, you still find yourself saying, God, I just kind of wish they would have endured some of that strife. But it's, I mean, like, that's, to me, that's actually been one of the most satisfying parts of fatherhood, is seeing your kid fail, and then seeing your kid get it right. I get so much, there's so much more of a high from that than seeing my kid get it right the first time. I really enjoy, and I'm not sadistic, like, it's, it just feel, like, it feels so much

• 1:42:31Speaker 01

  more satisfying, because you're like, okay, that actually feels like a moment where you, there's some part of you that just, like, a synapse fired, and some line, some dot in your mind connected with this other dot, where it's like, okay, I figured it out. I couldn't do it before, I can do it now. And it could be, right now, it's, it's like, multiplication. And it's just being able to start to see those dots really connect that I just, I love. It's very satisfying. It's like a Pokemon evolving in front of your eyes.

• 1:42:57Jay Shetty?

  I love it. Alexis, it's been such a joy talking to you. Honestly, this has been amazing, just learnings from you, from whether it's tech, to AI, to fatherhood, to brotherhood, to love.

• 1:43:09Speaker 01

  This is great. This is great.

• 1:43:12Jay Shetty?

  You're very kind, I appreciate that. But Alexis, we end every On Purpose episode with a fast five, or a final five, which means every question has to be answered in one word, or one sentence maximum.

• 1:43:23Speaker 01

  Okay.

• 1:43:24Jay Shetty?

  So Alexis, these are your fast five. The first question is, what is the best life advice you've ever heard or received?

• 1:43:31Speaker 01

  Be useful. It's Arnold Schwarzenegger quote, sorry, Arnold.

• 1:43:35Jay Shetty?

  I like it. Yeah. Second question, what is the worst advice you've ever had or received?

• 1:43:39Speaker 01

  Oh, I didn't take it. Do I have to have taken it?

• 1:43:42Jay Shetty?

  No.

• 1:43:43Speaker 01

  Paul Graham told me to get rid of the Reddit alien, and change the name to Octopop. And I said, no, I'm keeping snu and I'm gonna keep calling it Reddit.

• 1:43:53Jay Shetty?

  And that was a good decision.

• 1:43:54Speaker 01

  Worked out. Octopop, would you all be using octopop right now?

• 1:43:59Speaker 01

  And he wanted to change the alien to an octopus. I'm like, Paul, come on, we're not doing that. Brilliant guy, just not, not great with the branding.

• 1:44:06Jay Shetty?

  No, that. Question number three, if there's any other business dads listening that are struggling with the business and being a dad and trying to manage it all, what would be your advice for them?

• 1:44:17Speaker 01

  Aside from listening to my podcast, the good news is there are more avenues than ever because there are more and more people talking about this than ever. What book are we reading tonight? Like, what are you most excited about? And then when I'm on the clock for weekends in particular, I really try to lock in. And so it can be whatever you need to do. Obviously, your family is going to have different prescriptions, but create those traditions, create those routines. And that's one thing I would give advice to myself at 20 about over again. When I had more free time, when I had more youthful vigor, if I had more discipline, I would have been 10 times more productive.

• 1:44:55Jay Shetty?

  Yeah.

• 1:44:56Speaker 01

  And, and it shows up in sneaky ways. If, if I had gone to bed at midnight because I knew like my, I was diminishing marginal returns of my productivity were falling off a cliff and just gone to bed, slept for seven hours, eight hours, and then woken up and done the thing, I would have done it in 20 minutes. Instead of staying awake for another two and a half hours, like, no, that's not actually the best use of your time. And, and discipline is freedom. And I never would have believed that in my twenties or even in my early thirties, but becoming a parent, that's the only way I'm able to do these things. And that's not to say I'm perfect, but if you can incorporate ritual, routine, even before you have kids, you're going to be even better at what you're building. And then once you have kids,

• 1:45:39Speaker 01

  it's, it's kind of the only way to do it, frankly.

• 1:45:43Jay Shetty?

  I love it. Question number four, how would you define your current purpose?

• 1:45:47Speaker 01

  My current purpose.

• 1:45:50Speaker 01

  Is enabling a whole nother generation of entrepreneurs to do even bigger and better things than I did.

• 1:45:57Jay Shetty?

  I love that. That's such a great answer.

• 1:45:59Speaker 01

  And I mean, look, it's also you sleep a lot better at night because it's not your ass on the line for every one of those companies too. So it's a blessed position to be in.

• 1:46:07Jay Shetty?

  I love it. And fifth and final question, we ask this to every guest who's ever been on the show. The question is, if you had to create one law that everyone in the world had to follow, what would it be?

• 1:46:17Speaker 01

  Okay, this one, I cheated and I wanted to have one prepared.

• 1:46:21Jay Shetty?

  That would have been a good idea, yeah.

• 1:46:22Speaker 01

  But I think the best thing I came back with was a joke, which was, you know, everyone should be able to experience the joy of making someone they truly love happy. You talked about this earlier. Again, it's not really a practical law.

• 1:46:38Jay Shetty?

  No, I like that.

• 1:46:39Speaker 01

  But I have never felt more satisfied, or happy, or richer, or taller, or what, I've never felt more, any positive feeling you could feel than when I get the unsolicited, "I love you Papa" hug from my daughter. And again, it doesn't have to be your daughter, it could be anyone, but like, those moments for me are like black tar heroin. I am addicted to it. And so when I think back, hopefully as an old man one day, and I think about like, what are the things that really, really made me so incredibly happy, it's going to come back to those moments. And so I wish that for everyone as often as humanly possible.

• 1:47:23Speaker 01

  And the irony is, right, it usually doesn't cost any money. It means time, it means intentionality, it means other humans. And we're going to keep getting really good at making artificial intelligence. And I don't want that to scare folks, because I hope, I really, really hope and want to believe it gives us more time for the human communing that far few of us, or not enough of us, have a chance to do often enough. So I don't know, whenever you're, if you're breaking bread with people you love, like I said, these are all the things, going to a sporting event, going to an Angel City match, you're enjoying these moments of humanity with people you care about. And make an effort to tell those people, especially

• 1:48:05Speaker 01

  men out there, dudes, normalize telling the man in your life that you love them, whether that's your father, your brother, your best friend. You don't have to go buy a billboard. You can if you want, up to you, but like normalize having that conversation. You will not regret it.

• 1:48:23Jay Shetty?

  I love that. Alexis Ohanian, everyone, Business Dad Podcast, make sure you subscribe. And Alexis, I'm so grateful to your parents.

• 1:48:31Speaker 01

  Dude.

• 1:48:33Jay Shetty?

  You, you, you carry them. Yeah, you, you carry them and their energy so well. You can tell how deeply rooted their love is for you and the love that they had for the world. That seems to be oozing out of you. So it's really beautiful to experience that today. And I'm grateful that you came and spent these couple of hours with me.

• 1:48:50Speaker 01

  Thank you, Jay. This was awesome, man.

• 1:48:52Jay Shetty?

  Thank you, man.

• 1:48:53Speaker 01

  Thank you, brother.

• 1:48:54Jay Shetty?

  Thank you so much for listening to this conversation. If you enjoyed it, you'll love my chat with Adam Grant on why discomfort is the key to growth and the strategies for unlocking your hidden potential. If you know you want to be more and achieve more this year, go check it out right now.

• 1:49:13Speaker 01

  You set a goal today, you achieve it in six months. And then by the time it happens, it's almost a relief. There's no sense of meaning and purpose. You sort of expected it and you would have been disappointed if it didn't happen.

• 1:49:24Speaker 05

  Mr. President, my company informed me of the explosion on our rig on October 2nd. Causing massive water displacement and triggering a tsunami. They all heap the blame on me. Tom Cruise is.

• 1:49:35Speaker 03

  Digger got us into this mess and Digger's gonna dig us up. From the director of Birdman and The Revenant.

• 1:49:41Speaker 06

  What would happen if I stopped drilling? You're stalled, you're freezing there, that's what.

• 1:49:45Speaker 07

  With great power comes great deniability.

• 1:49:48Speaker 06

  I'm not the first then.

• 1:49:49Speaker 07

  Digger, see the trailer online, only in theaters October 2nd. Rated R, under 17, not a middle without parent.