Sean Rad: Lessons Scaling Tinder to the Fastest Growing Consumer Social App in History | E1199

1. 0:00 – 0:56

   Intro

   1. SRSean Rad0:00

      So product-market fit isn't one moment in time. Product-market fit is a constant iterative process. When I was there, when the team was there, we had a rule that every year, we had to redesign the entire product because we didn't want people to get bored and stagnant, and we didn't want to become complacent as a team. And every lesson we learned, the lesson was always focus. Focus on your mission. Focus on what you're good at. Stop trying to be something you're not. Every company needs to continuously fucking relearn that.

   2. HSHarry Stebbings0:31

      Ready to go? (upbeat music plays) (mouse clicking) Sean, I am so excited for this, dude. I- I've been looking forward to this one for a while. So thank you so much for joining me today, man.

   3. SRSean Rad0:51

      My pleasure. Happy to be here, Henry.

   4. HSHarry Stebbings0:54

      I want to start with a bit of a kind of tougher

2. 0:56 – 3:46

   Handling the Transition After No Longer Leading Tinder

   1. HSHarry Stebbings0:56

      one. You tie your identity to your company as a founder, and suddenly it's no longer part of you. Did you h- how did you deal with that detachment from identity when no longer CEO of Tinder?

   2. SRSean Rad1:07

      It's really hard because in my case, I sacrificed so much. Not only was it my identity, it was, it was sort of all I did for a big portion of my life. So when you walk away and one day that's no longer your identity, it's- it's- it's really, uh, existentially rocking to your core. It took me a while to recognize that that is not my identity and that is actually not healthy to make that my identity and that founders are better when their company is not them, because it's not about you. And it took me a while to sort of step away and see that. And actually reflecting back, you know, our most successful moments when we were, is when we were a little detached and can see the bigger picture beyond the individuals, and I think it's really important. I mean, a company is a group of people that are on a mission to solve a problem, and you need to take the individuals out of it. That's when companies perform the best, when there is sort of a, to some extent an all for one, one for all mentality, but we are here to accomplish a mission. We are all aligning against that mission. We understand our individual contribution to that mission, but we also have the humility to understand that none of us are significant enough or matter enough to success, and if we did, then that's actually a problem. We haven't built a great organization that's greater than us.

   3. HSHarry Stebbings2:38

      Do you think that's the case for many companies today?

   4. SRSean Rad2:41

      No.

   5. HSHarry Stebbings2:41

      I look at many companies and I'm like, actually, they are individual led in so many respects, and if you were to take some of those great individuals out, it's tough.

   6. SRSean Rad2:51

      To me, leadership, truly great leadership is when you see your, you know, when you sort of try to abstract yourself away, you know. If- if- if- if things are dependent on you, then you haven't really achieved something, you haven't really been a great leader and given to the next generation, sort of shared your talents and empowered other people. So I think truly great leadership, you know, the- the greatest CEOs are the ones that are there, always available, killing, you know, pushing the company forward, but are building organizations that if they step away, can run without them, because that's when you have a healthy organization. You- you- you- you can't have any individual be the source or single source of success or failure. Then you haven't matured the organization and that organization will never outlast

3. 3:46 – 11:51

   The Inspiration Behind Tinder

   1. SRSean Rad3:46

      you.

   2. HSHarry Stebbings3:46

      We mentioned that kind of it's a collection of people coming together to achieve a mission. I do want to kind of rewind the clock back. I hear there's some great stories that I have to unpack. I just want to start at the beginning, which is like-

   3. SRSean Rad3:58

      Yeah.

   4. HSHarry Stebbings3:58

      ... when we think about the inspiration, we forget today just how revolutionary the swipe was. Um, I might have been on a swipe swipe before this interview, um (laughs) -

   5. SRSean Rad4:07

      (laughs)

   6. HSHarry Stebbings4:08

      ... which shows you the importance you have to pay if you want to be successful on dating apps today. (laughs) But, um, it was such an innovation. Tell me, what was the inspiration behind Tinder? And when you go back, what did that look like?

   7. SRSean Rad4:22

      When, before I started Tinder, I'd just sold a company and was thinking again, what is next? Reinvention. And around that time, the mobile phone, the iPhone had just come out and been in the market for a few years, and it was really obvious, maybe this was a little early thought at the time, that this thing is going to change everything. The- the idea that we have, um, the world's most powerful computer in our hands with us all the time was going, bound to change the way we interacted with each other and the world, but I also saw very early that there were some potentially bad outcomes of, of that power. Um, you know, with great power comes great responsibility, and I think I saw very early that as much as the phone was connecting us, it was also separating us from the real world. You know, I'd sit at restaurants and I would just like observe my friends were, you know, heads down in their phone. It was the weirdest fucking thing. We're all together in a table, but everyone's head's down in their phone. And so, you know, for me, I- I- I was obsessed with this notion of how can the phone actually empower the real world and not take us away from it. So I had this insight one day, just kind of hanging around looking at my friends on their phone, um, at a restaurant, I'm like, "How can this phone help me connect with people around me?" And I realized there was a group of girls at the table in the restaurant and I would-... probably not walk up to one of the girls that I was looking at 'cause it would be inappropriate in that setting. I would have to really put myself out there. I run the risk of getting rejected, looking desperate. So I sort of wondered, "What if I could just tell the phone that I like her? And what if she also would tell the phone that I like her, that she likes me? And if we both like each other, now the ice has been broken and now that fear of rejection is gone, and now we can connect." Um, and that was like, that, what we call the double opt-in was the revolutionary thought behind Tinder, because every system of connection prior to that was riddled with this emotional angst and barriers to connection.

   8. HSHarry Stebbings6:47

      Do you remember when you released it? Do you remember when you pressed Go Live?

   9. SRSean Rad6:50

      Yes.

   10. HSHarry Stebbings6:51

       What does it look like from there? Does usage just go skyrocket from the moment you start?

   11. SRSean Rad6:55

       No, no. So when we released it, nothing happens 'cause no one knew about it, right? So it was a very anti-climactic, uh, uh, anti-climactic moment. Um, but the, the, what, what we started doing at a certain point, you know, sitting with the team and it's like, "Hey, we built this great product. We know there's something special here. What, what the fuck do we do?" And I think as an entrepreneur, you sort of have to, like, work with the resources that are around you. You have to make the most of what you have. And for us, it's like, we all had friends. So I was like, "All right, let's just start there. Everyone take out your phone, text 300 friends or whoever you have. Text your entire, text your entire address book." Um, and I think the thing that we texted was, uh, "Download this app and thank me later." Sort of wanted to create this, like, FOMO, mysteriousness. Um, and I think in total we texted 500 people. Over the course of a few days, uh, we, we had, I think it was, like, 700 signups. I sort of looked at the team like, "D- did anyone text anyone else?" Like, "W- where did this additional come from?" And we realized that it started going viral amongst our close group of friends. And then what we started to see, which was sort of confirmation of this thesis that we had, that we could uncover connections that would've never have existed if we removed these barriers. We, we started hearing that friends who already knew each other were now getting together. So I would have friends calling me like, "Oh, I never, you know, s- shit, I, I never knew she liked me. We never put two and two together. I'm going on a date with so-and-so." And, and it's like, whoa, okay, we've, we've been in the same friend circles for years, but neither of you expressed that interest. So, you know, it was that, like, confirmation, like, okay, this thesis that we have, that we're walking about our lives not maximizing the potential of our relationships is true. And it was working. And that was the-

   12. HSHarry Stebbings9:00

       Mm-hmm.

   13. SRSean Rad9:00

       ... that was the initial spark.

   14. HSHarry Stebbings9:02

       So we have 700 people then. We have the initial spark and we start to see that outgrow from the core. What happens then? How do we-

   15. SRSean Rad9:09

       So-

   16. HSHarry Stebbings9:09

       ... grow more fuel on the fire?

   17. SRSean Rad9:11

       So then, so first of all, Tinder, Tinder was a relatively complicated product to market because it is very much location specific, and you're building network effects, right? So, you know, th- the, you, the, the strength of the network, you don't want random people just sort of downloading the app and never opening it again, right? So, so you need a sort of strong connection amongst the net... So we kept thinking like, "What are, what are areas where, um, groups of friends or, or similar people sort of gather and congregate?" And one of those are parties. And, um, an intern of ours was, was, uh, in college at the time and his friend who was sort of like, she was the, one of the most popular people at USC was having a big birthday party with like, h- you know, I think it was like a thousand people were invited to this party. So we, we told her, we're like, "Look, we'll, we'll pay for the party. We'll throw the party. Um, but in exchange under one condition. Um, you have to do it at another location." So we shuttled all the students to another location where we had a bigger venue and we can invite more people. But the other, the other condition was that no one gets into the door unless they have Tinder on their phone. So we literally had bouncers at the door, the, you know, whether you are invited or not, anyone can come in, but you needed to have Tinder installed on your phone. Now, no one even knew what Tinder was, but the next day everyone woke up and saw the people that they saw at the party. Again, this, this, you know, confirming this thesis, it's like maybe there was that girl or guy that I didn't have the courage to walk up to, but now I see them in the app and now I can swipe right and now we're matching. We noticed that, that bringing people together and then empowering them through the app was a great marketing strategy. And that worked. So we had, um, once we, once we did that party at USC, over the coming days, it went viral on campus. Everyone was talking about it, everyone was sharing it. And we realized that was a great mechanism of when we introduced Tinder to the right groups of people, it takes a mind of its own. Um, but I can't stress enough though that none of that would've mattered if we didn't build a great product. Marketing's important, but I think this is another thing people sort of miss. They think like, "All right, I need to figure out how to get it out there, get it out there." But they don't spend enough time focusing on whether or not they have the right thing

4. 11:51 – 16:34

   Lean Startup vs. Perfection

   1. SRSean Rad11:51

      to promote.

   2. HSHarry Stebbings11:51

      Let's just delve into that then. It's on the product for, first before we do distribution. You know, a generation has been taught about the lean startup, just ship, get it out there, see what works. A lot of other people say, "No, actually you need to be a lot more of a crafts person and really build a great product experience and be very deliberate about it." Which side of the fence do you sit on?

   3. SRSean Rad12:11

      Well, first of all, you gotta be very clear about the problem that you are solving.And I think you have to feel, as a founder, a connection to that problem. You have to be the customer. I think products are incubated and grow in phases. And phase one is that you're using it, and the team is using it, and that you have, you have product-team fit. And then I think once you cross that boundary, then I think you could go to, like, product-friends fit. And then I think once you cross that boundary and it's working amongst your friends or, you know, network of close customers, then I think you slowly start expanding it. The idea of throwing shit at the wall and seeing what sticks is a very soulless, you know, effort. I, I, I, I don't, I don't subscribe to that. Um, I think you have to have a clear vision, test, iterate the vision. And don't put the cart before the horse. If it's not ready for a million people, you don't want to give it to a million people. You want to slowly start expanding your circle of reach, and test at every step. So product-market fit isn't one moment in time. Product-market fit is a constant iterative process because as the co- as the product grows, it sort of faces new challenges at scale. And just because it worked with a thousand people doesn't work, mean it'll work with a million people, doesn't mean it'll work with a billion people. Um, so, you know, and I think the idea of MVP, one thing people really miss in MVP is that if, you know, yes, you want to launch and get feedback, but if you launch a shitty product, what's the point? So I think there is a bar of quality that you still have to hit before that product is ready for people to play with. And if, and if you haven't achieved that, then whatever data you're getting is corrupted data to begin with. So this whole idea of laun- And, and another thing I'll say, w- we always believed in this, you know, Tinder, we always believed we have one shot. There isn't a second chance with users. We have one shot to impress them, and if, so, so we have to make that one shot count. And we would not take that shot until we're very ready. And I think that's the, the sort of lean startup, throw-shit-against-the-wall, I think, um, lacks a little bit of soul.

   4. HSHarry Stebbings14:41

      I completely agree with you. I'm, I'm writing. There's a lot that I want on that.

   5. SRSean Rad14:44

      (laughs)

   6. HSHarry Stebbings14:45

      The, the one-shot wow, is that for you match? Is that for you surfacing a girl that someone finds pretty? Is that for you surfacing a friend? What was the wow moment that you craved and coveted in those early days?

   7. SRSean Rad14:57

      You know, for us, it was 100% about connecting you with someone and you walking away with meaningful experience.

   8. HSHarry Stebbings15:08

      I think product marketing is such an important skill. And I always say to founders, be as narrow as possible, because you want to find your thousand true fans. You want to find those people that go, "Yes, that's me." And I worry that-

   9. SRSean Rad15:20

      I think you can be narrow with the problem you're solving, but maybe you do yourself a disservice if you're too narrow in the audience that you're serving, right? Because that problem that-

   10. HSHarry Stebbings15:29

       Mm-hmm.

   11. SRSean Rad15:29

       ... you're solving can speak to many audiences. So for us, the problem we were solving was to make a new connection. Everyone felt, at that time, and I think even more so now, a little isolated. They wanted new connections, they wanted to meet someone for whatever reason, if it was marriage, friendship, whatever. Um, we were all about make a new connection. We, we actually had a rule, you were not allowed to say "dating" at Tinder. You were not allowed to call Tinder a dating app. You were not allowed to say "marriage" because we weren't about that. We were about an introduction, we were about connecting you with someone for any reason. And the, the, the sort of marketing message that we would always repeat is, "Find out who likes you." It's that FOMO. It's like, "Who likes me that I don't know about?" So that was the, the, the hook, right? The reason you would come in, is because, "I'm curious who likes me." The reason you would stay is because you made a new connection that was valuable, that was meaningful, for whatever purpose, for whatever intent you had.

5. 16:34 – 21:39

   How Tinder Measured User Retention

   1. SRSean Rad16:34

   2. HSHarry Stebbings16:34

      How did you define a retained user? You know, at Facebook they said, like, "After five f- friends have been added, we count that as, like, a retained and activated user."

   3. SRSean Rad16:42

      Wow.

   4. HSHarry Stebbings16:42

      How did you count a retained user?

   5. SRSean Rad16:45

      I think the, the, the thing that we really focused on is how many conversations we could drive. So, you know, there's swipe, match, talk. And the ultimate value proposition is that you're in a dialogue. So the number of unique conversations we were driving was, was one of the metrics we would look at a lot. Now, up-funnel, it was also we did look at retention in the sense of what was DAO to MAU, MAU to, you know, WOW to, to MAU. But over time, those metrics became less important. Um, the metrics that became more important were, uh, conversations, matches, sort of us delivering value, the metrics that measure true value, and revenue, which is your desire to compensate us for that value. Retention on its own, I mean, e- e- you know, I think it's a, it, it is a problematic metric that could lead sometimes, if you're not careful, to a lot more harm than it can good.

   6. HSHarry Stebbings18:00

      How so?

   7. SRSean Rad18:01

      Because I think when you're focused on retention, and you believe that retention equals value, you're, you can sometimes delude yourself. Because me spending hours doing something doesn't mean I extracted true value out of it. I could spend hours getting high.... doesn't mean that's valuable in my life. You know, so drugs have a great retention. Um, and they're really good at retaining people. But are they actually driving meaningful value? I would argue, you know, Facebook and social media is really good at retaining users and almost against your free will and hacking your desires and keeping you there. And they do that because they make money through advertising, and the more time they have with you, the more ads they can put in front of you. But is that truly enriching my life? Is that truly creating value? Or can you look at that and saying, "Well, that's actually distracting me from a lot of other shit that is more meaningful and more valuable in my life." So we were always very careful, like, you know, there was many times a desire to look at retention as sort of the end-all-be-all metric. And by the way, we had fucking phenomenal retention. You know, we had, we had retentive powers beyond social media platforms. But what you were doing on Tinder, I always thought was 10 times more meaningful than kicking back and just swi- you know, watching content. You were actually connecting with human beings. And I think to me, what we have at the end of the day, all we have is connections. You know, it's like all the other shit is just noise. At the end of the day, all we want is an e- is to experience love with other human beings. Remember I told you, as things scale, right, new problems form. They take a new shape. If I was still at Tinder, and, and in fact while I was there, this, this was sort of a metric of success I always drove home for the team, is that retention and the number of connections isn't as important as the quality of connections. So the, the, the natural course of Tinder I always saw is actually we're moving to a world of no swiping. Where Tinder is so smart that I could just say, "Harry, I have the person for you. And why don't you focus on that? And if I was wrong, great, I'm happy to introduce you to someone else." So it's sort of like, you know, technology bec- becomes, I think, the better it gets, the more human it gets. And to me, the ultimate archetype was the matchmaker. You know, could we achieve the success of the human brain matchmaker who was able to say, "Harry, here is the girl for you. Again, I'm not gonna judge what you wanna do. You know, I'm just gonna introduce you guys. You can do whatever you want."? So, I think, you know, once, once the core team left, I think that promise, that mission was maybe replaced with a desire for retention, a desire for revenue. And, and, and I think that, that this, this sort of intention of why we created that company, what we were tr- what we were trying to achieve got lost. So over time, the quality of the product decayed because no one's actually sitting there and saying, "How do we scale the impact of the product?" Everyone's saying, "How do we scale the metrics of the product?"

6. 21:39 – 28:41

   Is Monetization Inevitable for Improving Product Quality?

   1. SRSean Rad21:39

   2. HSHarry Stebbings21:39

      Is that inevitable? These are businesses with costs. They have to post quarterly numbers. I agree with you totally and you feel it in the product. Now, the products today, as we said earlier, unless you pay, they're pretty horrible. And you hit paywalls. I mean, they're just, they're just bad products unless you pay. And then when you pay, it opens up. But, is that just inevitable?

   3. SRSean Rad22:01

      Look, you could make the argument that everything dies. It's just a question of when and how, right? All companies are organisms, just like humans. Humans die. Companies die. And it's just a question of c- uh, of how long and, uh, what is the longevity. And I think if you don't keep disrupting and you don't keep setting the bar higher and higher and higher, you will achieve complacency. And complacency, which is a lot of big companies sort of die by complacency. You have teams who don't care. You have politics. You lose sight of why you are there. It's every person for themselves. You lose sight of that mission. Or you're not intellectually honest and you're not forcing yourself to disrupt yourself and re- and question the mission and improve it. So, I wouldn't say it's inevitable. I think, I think we've had, I mean, organizations that have outlasted my lifetime, your lifetime. Maybe they'll outlast my kids' lifetime. So nothing's inevitable. But yes, I think everything has a natural decay or conclusion. The question is, when? Nothing's forever. That's for sure.

   4. HSHarry Stebbings23:33

      Before we talk on nothing is forever, which I have to touch on 'cause you said that in a kind of wonderfully calm and cavalier manner, um, how do you feel about founder-led companies being so central to enduring success? This is something that, you know, we had Deleon at Founders Fund really eulogize on in terms of the importance of it, and many do, but others say no. How do you feel about it has to be founder-led?

   5. SRSean Rad23:55

      Founders are really good at keeping and reiterating the mission, because they care the most. Sometimes, you know, founder/market fit, team/market fit is essential. When it is your personal story, which it often is for founders, it's, it's, it's another level of storytelling. And it doesn't mean that the founder is the best person to execute it. I actually think great founders put the company before themselves and are intellectually honest and self-aware enough to say, "Hey, you know what? Maybe..."... I've taken it to this point, and there's someone else better than me to take it to the next point. I don't believe that a founder is forever. I think the founder energy is required for success, and I think over time, you can have different founders. You know, you, you, you, you could, you c- you have people who can come into an organization with a new vision, a better vision, and I think you would call them a founder, at that moment in time.

   6. HSHarry Stebbings25:01

      You can, and I hope I'm not being too spicy here. But I also heard that when you were not in the role of CEO at, at a point, um, your exec team came and said, "Well, if he's not in the role of CEO, we're leaving."

   7. SRSean Rad25:16

      (laughs)

   8. HSHarry Stebbings25:16

      (laughs) Which is quite a jarring position for anyone-

   9. SRSean Rad25:21

      Yeah.

   10. HSHarry Stebbings25:21

       ... to, to be in. Can you just take me to that? What happened? (laughs)

   11. SRSean Rad25:24

       There was a moment in time where I think Tinder was growing so fast, it-

   12. HSHarry Stebbings25:30

       When you say growing so fast, like what was that? Like users? Like w-what sort of scale?

   13. SRSean Rad25:35

       Users, revenue. I think, you know, if I, if I, uh, we used to play this game where we would chart the growth rate and figure out how fast we would get to a billion users if we held the growth rate. And I think if you, if you charted the growth rate we experienced in the, um, at a certain moment in the first year, we would have reached a billion users in three months. That's how fast we were growing. Um, so now obviously we didn't sustain that growth rate. Um, but the product was growing fast, the organization was growing fast, revenue was growing fast. Um, and we were growing so fast that we couldn't even solve problems with humans because we couldn't hire humans fast enough. We had to get creative at solving problems. But at a certain point, I had felt like, "You know what? Like, I need help." I felt like I wanted my Sheryl Sandberg. I wanted my partner who can help me scale the organization while I focus on product and technology. So we brought in, um, a very, very experienced person, and I think the board sort of... I mean, he was, he had a, he was, ran a public company, very experienced. And I think the board sort of felt like, "Well, Sean, you know, maybe we should give that person the CEO title 'cause they would carry more authority, and then you do the same thing you're doing, but take president title." And I was like, "Okay, fine with me." But when I stepped out of those other functions or I kind of stopped being in the room for a lot of those other functions, it created a lot of issues in the organization. And at one point, yeah, I don't know if this is about me or maybe the other person wasn't that good, um, but at one point there was like mutiny. We had the entire executive team, uh... I don't talk about it, but since you know the story I'll say it. I don't know how you found out, by the way. (laughs) We, we try not to talk about this. But there was one point where the entire executive team, u- un- unbeknownst to me went to the board and basically said, "If Sean doesn't come back in the CEO role, we're all quitting." Um, I found that very flattering. I think the more... Um, I mean, it was definitely like a crazy moment for me personally. Um, I think the translation, what I took away was that the team was saying that product and engineering isn't everything. The other parts of the organization equally matter. In fact, every part of the organization equally matters. And maybe it was a mistake on my part to say, "I'm gonna maybe play favorites and spend, give a little more love to this part of the organization, and, um, as a leader, outsource another part of the organization." And I think the truth is that the take, you know, the learning that I had is everything matters equally. You know, unfortunately, the team didn't come tell me that. (laughs) They sort of just threw up their hand and said, "Come back or

7. 28:41 – 35:17

   Which Challenge Was Hardest: International Growth or New Product Development?

   1. SRSean Rad28:41

      we quit."

   2. HSHarry Stebbings28:41

      I have to ask. I was thinking this ever since you said it, but I so agree with you when you said about product market fit comes in kind of chapters. When you look back on the different chapters, which was the hardest one? Was it international expansion? New city? If so, what city? What country? Was it new product? If so, what product? What segment was the hardest in unlocking the next?

   3. SRSean Rad29:04

      International expansion was, was one of the hardest things to wrap our head around because first of all, building a global organization is not easy. Building a global team and making people in another country feel like they are part of the team, even though the executive team isn't there, you know, sitting with them, that's not an easy thing. But it was particularly difficult around the Tinder product because in the beginning, in the early days, we thought localization meant that the language of the app had to adapt to the language of the user. But localization is much more than that because particularly around social human connection and relationships, there are cultural differences in everywhere in the world, which means the product had to adapt to meet those cultural differences, which means Tinder was slightly different as a product in every country, which means we had many product organizations servicing the same core product. And this-

   4. HSHarry Stebbings30:08

      What was the str- what was the strangest product alteration that you had to make?

   5. SRSean Rad30:15

      I think the strangest thing was that in... (laughs) I'll, I'll give you two stories. So in, in Korea, group dating is actually the, like the ex- I don't know if it is now, but back then when we were looking at it, that's like the socially accepted norm.Like it's actually- it's actually very rare that I would go out one-on-one. It's usually friends, or double dates. Like we're going out as a group. So group dating was a huge thing. Which like, so we had to like really think about that experience, like reorient Tinder as a group dating app, not as a individual dating app. Um, so that was, but then what was interesting as we, as we ro- as we reoriented that, it got us thinking like, "Well, could that be a thing everywhere else? Maybe that's actually a more effective means of connecting. So could we bring group dating, could we make that a thing? Could we make that easy?" I mean, naturally a lot of the times we go out with our friends, you know, and, but, you know, we didn't really double date until it's later into the, into the relationship. So that was one thing that was interesting to tackle. Another thing was that in India, it was not really, like e- there was a system of dating and marriage that was, uh, very much curated by your parents. Your parents decide. And I think that was a moment in time where we were like, "Hey, we could, we could adapt the product to that, but actually no. We're, we're not going to," because we believed in empowerment, and we believed that you should be in control of your own fate when it comes to love. So, that was actually sort of a moment where we were like, "No, we're not changing the product. Even if it means we're gonna have less users," because it was socially less acceptable. And we're gonna let society sort of take its course and correct itself. And maybe if we gave this capability to people and made it easier for them to take their romantic life into their own hands, then maybe they could break out of social norms, which is what happened, and I think that's- that's evolved in India. Um, so it's like unique things like that where it's like, wow, the- the- s- the social norms and the dynamics are just completely different.

   6. HSHarry Stebbings32:38

      Okay. In hyper-scaling, you have so many decisions coming at you so fast. What did you do that you wish you hadn't done?

   7. SRSean Rad32:45

      I would say the Tinder team was maniacally good about focus and prioritizing and saying no and keeping the product simple. And in fact, we believed in simplicity. I think if you look at the Tinder product, it's very simple. You know, I- we- I would always reiterate the Albert Einstein quote, which is like, I don't know the exact words, but if- if something isn't simple enough, it's because you don't understand it enough. And I think the more you get to the essence of something, the simpler it actually becomes. And it's like fools make things more complex. Prioritizing and picking our battles was very critical. And that became a little harder as we scaled. I often, so at a certain moment, you know, in- in- in the early days, we were very much one team, f- all building towards one product. Everyone was involved in one release. We all knew what everyone was doing. Even by the time we were like 100 people, that was still the case. And then at a certain point once we expanded, you had to sort of divide and conquer, and you had more capabilities and you had more teams so you wanted to feed them with projects, so you lowered your bar of what you would do. And then I think the- the clarity and focus started to dwindle, and then we had to figure out how can we divide and conquer but all map towards one cohesive vision, which became the next challenge. So, I mean, we- we had an environment where we really wanted to give people freedom-

   8. HSHarry Stebbings34:33

      Mm.

   9. SRSean Rad34:33

      ... to execute. Like, I- I- I hated the top-down bureaucratic approach to creation. It was horrible. Now I can come to the company and say, "Here's my vision. Here's where I think we should go, but I'm not gonna solve it. Everyone sort of bottoms up, come up with solutions and take ownership." So we really wanted to instill that bottoms up, everyone has a voice, the best ideas will win mer- merocratic culture. Um, and then sometimes the bigger you get, that could lead to a little bit of drift and people doing things that maybe they shouldn't be doing or they have no, or the company has no business doing. So I think as you scale, you have to build new systems to protect

8. 35:17 – 42:36

   Biggest Failure & The Lessons Learned

   1. SRSean Rad35:17

      against drift.

   2. HSHarry Stebbings35:17

      What was the thing that didn't work biggest and what did you learn from it?

   3. SRSean Rad35:22

      So, the- one of the biggest things, okay, so in- in the early days, very few people know this, but- but we had a lot of, every user sort of got to the point where they had a lot of matches, where it was almost like you would open the app and you're like, "I don't want to meet someone new. I need to make sense of all the people who already want to connect with me." So we started shifting our focus to like post-match. And one of, and- and what we wanted to do is create more moments where you could get to know your matches and find opportunities for connection. So we created this product called Moments, which was sort of Instagram Stories before Instagram Stories. You could, uh, share a moment, like something you're doing in the real world, and it was an expiring 24-hour moment and people could reply to it and your matches could be like, "Oh, you know, great." Um, and we- we all loved the product so much that we were like, "You know what? Maybe this could be for friends. Maybe we let Tinder be more than just, you know, br- romantic connections. Maybe you can add your friends and you can share moments with your friends." So we sort of, we sort of tried to shift from a dating product to a social network, and we very quickly learned-... we have no business doing that. Our brand, our mission, our thesis is very much about creating new connections, m- introducing you to someone new. We weren't in the business of connecting you with your friends and our users didn't want that. At some point we also said, "Hey, let's create an app to help you make friends." Um, and we very quickly learned that no one wants to open an app to make friends. Like, that's a very desperate, weird experience. And then we said, "Well, could we apply Tinder's mechanism to business connections?" And then we quickly learned, well, no one, no one wants to swipe and match and make new business connections.

   4. HSHarry Stebbings37:30

      And so that was a real realization actually, that that wasn't what people came to you for.

   5. SRSean Rad37:34

      Yeah. It was a reminder, I think the more we scaled and every lesson we learned, the lesson was always focus. Focus on your mission. Focus on what you're good at. Stop trying to be something you're not. And I think every company needs to continuously fucking relearn that. It's like even when Steve Jobs left Apple and he came back, what did he do? He killed a bunch of products 'cause he said, "We have no business doing these other products. This isn't in the DNA and the soul of the company." So I think when you get bigger and you have more money and you have more resources, you, you fall in this trap of, "Oh, we could do more things." But you have to stop and ask yourself, are, like, just because we can, should we? Like, do we have any business doing those things? Does that map to our core competencies? Is that why the thousands of employees we have actually joined this company? And if you're gonna change that vision, there better be a very good reason and it's gotta be bottoms up. It's gotta be start with because your users are asking for that. None of our users asked for a friend-making app or a business-making app.

   6. HSHarry Stebbings38:46

      How effective was paid in the early days? I'm just thinking about what you said there on constraints. If you don't have the constraints, you could have spent a lot of money on paid.

   7. SRSean Rad38:55

      It was highly effective. Our perspective on paid features was the only reason we would charge you is if charging you for that feature made the ecosystem better. Meaning, if we gave that capability to free to everyone, it would actually dilute the quality of the ecosystem. The first feature we launched that really started making a lot of money was the Super Like. So we wanted to have this signal that you're not just someone I swiped right b- right on. You're extra special. I'm not just like any Joe Schmoe. Like, I actually, it's sort of like in the real world, I can walk up to someone and say, "Hey, what's up?" Or I can walk up to someone, and maybe this might not be a good idea, and say, "You know what? Like, I feel a strong connection. Like I really, really, like please g- you know, like I really like you." Like, there was sort of like the next level of romance. So that was what the, um, that was what the Super Like was. But if we actually gave it to free, for free to everyone, it would have no value. So we gave one free to everyone and then we charged if you wanted to Super Like again. So what the one free did is it took away the desperation. So someone didn't know, did I use my one free on you or did I actually spend money to get your attention? Which could make me look desperate. So it gave me the sort of excuse, like the out, but then I can spend money to buy more Super Likes and Super Like more often. Um, but again, charging for that not only allowed us to build better products, it created more revenue, allowed us to fulfill our mission, it built the business, but it also made the product better because it created a new feature where it made sense for us to charge.

   8. HSHarry Stebbings40:54

      The free is smart 'cause it removes the desperation. The hard thing is you don't wanna look like you paid for it and it's too desperate. I am intrigued, you said about kind of the curation on liking. How do you feel about the league which takes it to the extreme, which has like three per day and that's all you're gonna get?

   9. SRSean Rad41:12

      I don't subscribe to anything that's elitist. Um, I think in many ways a lot of these dating apps are elitist. They are living in a world where one person or one group is better than another. Bumble is elitist. Why, you know, women go first. Women have all the control. Why? Who are, you know, like, that, that is a, I, actually, I'm not even sure that's good for women.

   10. HSHarry Stebbings41:43

       It puts the onus on them to be-

   11. SRSean Rad41:45

       Yeah.

   12. HSHarry Stebbings41:45

       ... creative. Why should they be? It's unfair on them.

   13. SRSean Rad41:49

       Yeah. Yeah. It was, it was always a weird concept. I'm like, "What?" It was a good marketing gimmick, but I, I don't think it actually ever made sense. And then, you know, the league's perspective is, you know, you have to be, you know, some educated, highly educated, or Raya's perspective is you have to be cool and rich. Like, fuck that. It's like, Tinder was always you're yourself, you're human, we're gonna find and match you with people who love you for you. And everyone deserves love and everyone deserves a match and everyone is beautiful and everyone is amazing. We wanted to solve core human issues. We didn't want to give a leg up to one group or another group.

9. 42:36 – 45:45

   Is Sean Proud of the Tinder Product Today?

   1. SRSean Rad42:36

   2. HSHarry Stebbings42:36

      Are you proud of the Tinder product today?

   3. SRSean Rad42:38

      I haven't been there in a long time, so like would I look at the product and say I'm proud of the existing iteration of the product? Um-I, you know, I think I would look at the product now and say, "Fuck." Like, all the missed opportunity 'cause I think w- when, when the core team when I left and then others left, there was a lot of unfinished business. You know, like we, we had a road map that I would say was, like, 10 years long. We knew once we achieved this, it's gonna open the opportunity to this, it's gonna open the opportunity to this. So I think I would look at the product right now and I would say, "It looks the same as when I left." That makes me sad because when I was there, when the team was there, actually we had a rule that every year we had to redesign the entire product. That was a rule. We, we would redesign the entire experience every year because we didn't want people to get bored and stagnant and we didn't want to become complacent as a team. So we would have to have one major redesign every year, which then forced us to reimagine all the features. And I think it was brilliant to exercise because it kept upping, taking it to the next level. I think you see that in companies, uh, like Apple. There's this, um, commitment to always improving and perfecting and the product is never done. The product is always at 1% good and there's always so much more to do. So that was kind of the energy we had when, when it was... I, I don't know. I, I, I think it's still there. A lot of that still exists today. But I think that, um, the energy, the passion, the, the, you know, maybe isn't as strong as it was in the early days, but that's also, again, natural course of businesses. As you scale, you lose some of that.

   4. HSHarry Stebbings44:32

      Do you agree with Whitney's take that we're gonna have essentially AIs talk to each other, coalesce, see if you like me and I like you AI, and then we both like tennis and yay, and then we form a match? Is that how we'll have like a virtual dating self?

   5. SRSean Rad44:51

      I think that is a very sad idea.

   6. HSHarry Stebbings44:55

      (laughs) I'm so glad you do. (laughs) I do too.

   7. SRSean Rad44:59

      Um, I, I, I think the journey is part of the reward. Me actually talking to someone, getting to know them helps me learn about myself, helps me learn about them. It's not about a transaction. Romance is a journey. It's not just an ends to a means. So I think abstracting away the journey is the stupidest idea I've ever heard. Um, and you learn a lot in that journey. And, and look, it's like addiction is when something is too easy, when you get a free dopamine hit without doing a lot of work, and you actually feel worse about yourself. When you have to work for something, the reward is even greater.

10. 45:45 – 50:30

    Sean’s Relationship to Money

    1. SRSean Rad45:45

    2. HSHarry Stebbings45:45

       I didn't have money when I grew up and I, I read on the tin that when you got money, you would be happy. Um, I got a little bit of money, (laughs) not quite nearly as much as you did from Tinder. But, I wasn't very happy and it was a very awkward time of like, "Shit, if the thing I've always been chasing isn't actually the thing that I was promised it was, what do I do now?" How do you reflect on your relationship to money?

    3. SRSean Rad46:13

       Number one, you, you said it, money does not buy you happiness. I think up to a certain point, right? You know, n- you, you want freedom. Money brings you freedom. Freedom does enable happiness. But after a certain point, it doesn't make you happier. If you're not careful, it could actually complicate your life a lot more. You can accumulate more shit. It could change your relationships.

    4. HSHarry Stebbings46:41

       What stage does it complicate? 'Cause at some stage you have to have a family office, and then you have t- have people to manage your family office. And then taxes become a complete nightmare. And all of this becomes chains.

    5. SRSean Rad46:53

       And i- it took me a while to see this but I live a life that is much less than I can afford to live, because I don't want chains, I don't want stuff, and I don't value those things. I don't care about yachts. I don't care about... Like my, my friends are my childhood friends. Building, creating products, solving problems is what makes me happy. Um, and I think there's a lot of other things. When you have a lot of freedom, you can kind of get crushed by the paradox of choice and possibilities. So I think and, and... You know, when I have, when I achieve that freedom, it was also very hard because what do you do when, at least financially, and to some extent as an entrepreneur, you can kind of do anything? So it's, it's sort of a harder problem, harder to find meaning when you're living in a world of infinite possibilities. And I actually think that's why globally there is a little bit of a crisis of meaning, because we're, we're at a moment in history where regardless of your w- wealth, by any means, we are all way wealthier and have accessed to way more resources than previous generations. Which also has expanded the options and possibilities and who we can become and I think-

    6. HSHarry Stebbings48:28

       D'you think, d'you think that's actually the case though? Sorry, I don't mean to be provocative but, you know, when we look at the, the price of food today, when we look at the increasing homelessness, when we look at the increasing levels of drug addiction, does not feel like the standard of living is getting much better. Yeah, we can get-

    7. SRSean Rad48:45

       No, no.

    8. HSHarry Stebbings48:45

       ... doors-

    9. SRSean Rad48:45

       I didn't say the standard of living is getting better. I said our access to resources are getting better.And the more abundance we have, if we're not careful, can actually impact our quality of life. Because more choice isn't necessarily better. It's like when you show up to the restaurant and you have a book this big of items, it's not easier to make your choice of what you want to order than if, if it's just one page of something that's highly curated. So I think, you know, in a world where anyone, more than ever anytime in history you can get on YouTube and learn anything, you can become anything, we're more free than any generation, we have more possibility than any generation, I think it also becomes harder to identify who you are, what you want, and meaning in your life. And I think at a different scale, success sort of created that same challenge. My whole life was building companies, trying to make money, getting to the point that I wanted to be. And then when I got there, I was kind of like, "Okay, now what? Who am I? What do I do with my time?" And I could do anything with my time. So what is meaningful? And that requires you to look inward and really self ex- you know, explore. Or you could look outward and replace it with a bunch of noise and shit that actually distracts you from answering that question of meaning. So in a sense, that's why I say, you know, kind of getting what you want sometimes can create the next challenge. Life is a journey of challenges. There's never, you're never gonna get to the end of the road.

11. 50:30 – 53:01

    Choosing The Family Office Over Starting Another Company

    1. SRSean Rad50:30

    2. HSHarry Stebbings50:30

       Yeah, I think I'll just buy the Bugatti. Yeah.

    3. SRSean Rad50:32

       (laughs) .

    4. HSHarry Stebbings50:32

       That's m- n- much, much better. I don't want a Bugatti.

    5. SRSean Rad50:34

       Y- You'll, you'll buy the Bugatti, you'll enjoy it for two weeks, and then you'll get over it.

    6. HSHarry Stebbings50:39

       I, I, I won't actually 'cause I'm legally not al-

    7. SRSean Rad50:41

       (laughs) .

    8. HSHarry Stebbings50:41

       I'm not, I'm not allowed to drive, Sean. So I, I'd have to sit in it stationary. Uh, but I wouldn't enjoy it. So then you decide, okay, I'm gonna do a family office and I'm gonna invest a lot more, work a lot more hands-on with many more companies. Why? Why not do another, uh, company? You said you had a 10-year roadmap. Can-

    9. SRSean Rad51:00

       I've, I've, I've done, I've done both. So I, I have a family office where we've invested in over 100 different companies and fund. And I enjoy that 'cause it, it, it allows me to meet other great entrepreneurs, to give back, to mentor, uh, to learn myself. Um, and then, but at heart, I'm a builder, I'm a problem solver. That's what gets me up in the morning. I like to solve problems. I don't talk about it 'cause I don't wanna... I've, I've started four companies since Tinder. Um, but I just kind of purposely, I think I kind of learned, like, it's a little easier to build without a lot of attention.

    10. HSHarry Stebbings51:39

        Post-success, do you have a lot more leverage? Do you see what I mean by-

    11. SRSean Rad51:43

        Of course. I think, I think any, any anyone who has accumulated experience and wealth also accumulates freedom and leverage, no matter at what stage. So, of course. I have, I, I, I would say, I would say I can, I have more options. I can think bigger.

    12. HSHarry Stebbings52:03

        And so you have a CEO for each business-

    13. SRSean Rad52:05

        Yes.

    14. HSHarry Stebbings52:06

        ... that runs day-to-day, and then you finance and do strategy with them.

    15. SRSean Rad52:10

        Yes. And I think it's a really rewarding position to be in, um, 'cause I can focus on strategy and trust others to run the business. Doesn't mean that I don't come in and get detailed and help in the areas where maybe I'm the best person to do something. Um, but, but I've, I've, I've, I've found a lot of meaning in, in building. So I'm not gonna stop building.

    16. HSHarry Stebbings52:37

        What were the biggest lessons you had in setting up the family office?

    17. SRSean Rad52:41

        Um, investing is hard.

    18. HSHarry Stebbings52:43

        (laughs) .

    19. SRSean Rad52:44

        And it's a full-time job. Investing requires a lot of discipline. It requires, um, you to really experiment, understand what works for you, understand what doesn't work.

12. 53:01 – 58:00

    Biggest Lessons from Setting Up The Family Office

    1. SRSean Rad53:01

    2. HSHarry Stebbings53:01

       Setting up a family office is not a simple thing to do, actually. What are your biggest lessons from setting up the family office?

    3. SRSean Rad53:09

       Look, investing is hard. Uh, y- you know, at a certain point, you have to build an organization. It's like building a company. Carries all the challenges of building a company. You have to have a vision, a thesis. You make mistakes, you learn, you iterate, you become better over time. Um, so, you know, the family office is no different than building a company. We're just in the business of investing.

    4. HSHarry Stebbings53:38

       Did you have a clear strategy from day one? I'm gonna put 25% in directs, 25% in funds, 25% in cash, 25% in property?

    5. SRSean Rad53:46

       I, I, I had a high-level vision, but I was also, I iterated the more I learned.

    6. HSHarry Stebbings53:54

       What did you start with and what did it change to?

    7. SRSean Rad53:57

       The, most of what the family office does is we invest a lot in real estate, 'cause I think r- real estate is an amazing asset class. Um, we invest a lot in venture. Um, that's direct or through funds. Um, and we, we invest a lot in public equities. We invest a lot in credit and debt. There's, uh, different things and then there's a lot of things we don't do. There's a lot of things that we don't do either because I don't feel like we understand it enough, we're not good at it. So I think, you know, for me, it's really focusing on the areas where we can add value, where we have an edge. And, you know, who knows? It, it morphs as, as, you know, as new opportunities presents itself, we're, you know, we're opportunistic. But for the most part, it really is following passion and love and the things that I enjoy working on, and I wanna work on, and I wanna spend time on, and-... eliminating distractions as much as possible.

    8. HSHarry Stebbings54:58

       What's been the single best investment?

    9. SRSean Rad55:01

       Probably SpaceX. Invested a lot in SpaceX very, very early.

    10. HSHarry Stebbings55:05

        That'll do it. (laughs)

    11. SRSean Rad55:08

        Yeah, and I, and I think, look, I, I, I think the, the thesis there was actually very simple. It was I admire Elon. I think he's a once-in-a-lifetime entrepreneur, and I was just willing to let him invest my money.

    12. HSHarry Stebbings55:25

        (laughs) What was the worst investment and lessons from it? If you don't wanna say what it actually was, by all means, um, but what were the lessons from it? So for example, I invested in Pakistan once, and I lost all of my money, and my lesson from that is a business is more than the numbers on paper. There are externalities that can kill a company, like a presidential election in this case, which I had never factored into the death of a company.

    13. SRSean Rad55:50

        Yeah. I, I, I think, I think the worst investments were when I overlooked, when I chased the idea and not the team. So there were moments where I'm like, "Fuck, this, this idea is so good, but I'm not really sure-"

    14. HSHarry Stebbings56:10

        Ooh.

    15. SRSean Rad56:10

        "... about the team." Like, "Do they have the, the, the passion, the energy to go and execute? Is their heart really in it?" And I kind of ignored those elements 'cause I'm like, "Oh, the idea's so good, I don't wanna miss out." Um, and nine times out of ten, never works. So I think, you know, my, the, the number one thing is team and passion. I think you want a team that, you know, it, their, their heart and soul is in it. Like, you have a founder/market fit. They are building the product for themselves. They are the customer. They understand it. It's coming out of some personal problem or experience, so they won't give up when times get tough. They'll power through. They'll iterate. They'll morph. Um, teams that are humble, self-aware, are able to recognize when they made a mistake and adapt versus constantly make excuses. "Oh, it wasn't my fault. The market was this. This didn't work out. Let's blame the market. Let's blame the circumstances," rather than, "Let's look in."

    16. HSHarry Stebbings57:19

        Will you invest in someone you don't like?

    17. SRSean Rad57:21

        Not anymore.

    18. HSHarry Stebbings57:23

        Why not anymore?

    19. SRSean Rad57:24

        'Cause it just never works out.

    20. HSHarry Stebbings57:26

        (laughs)

    21. SRSean Rad57:26

        And because I think I have the l- the, the luxury, the gift of being able to work with people that I really enjoy working with. And again, that's what life is about. It's about relationships. The money doesn't matter if you don't have great friendships, relationships, partnerships, and love in what you're doing. It's like love is, love is the energy that I think produces the best outcomes and the greatest results.

13. 58:00 – 1:01:18

    Advice to Maintaining a Thriving Relationship

    1. SRSean Rad58:00

    2. HSHarry Stebbings58:00

       Good segue. Thank you for that. That's very nice. You teed me up perfectly, because y- y- l- you, I, I think you literally must have facilitated more love in the world than anyone else in human history, could be a, a fair enough statement.

    3. SRSean Rad58:13

       Maybe.

    4. HSHarry Stebbings58:13

       Maybe 50 billion matches, eh, according to your Twitter bio. Um, my question to you is, you have an incredible relationship with your other half. What are the most non-obvious secrets, pieces of advice on how to have a thriving relationship? Non-obvious.

    5. SRSean Rad58:30

       It is very, very hard. Relationships, I think, force you to, when they're good, to become better as a person. But in order to become better, you gotta stick through the hard times and not give up.

    6. HSHarry Stebbings58:47

       Do you think we give up too easily today?

    7. SRSean Rad58:49

       I think because we have more options than we have had in any moment in history, that increasingly, we have the ability to switch and give up. Like, when we were, uh, y- you go back in some moment of time, it's like you were in a tiny little village, and if you're lucky, there was one person that you love, and cutting bait, I mean, where were you really gonna go? You had to stick through it. Now, you could quit, and you could say, "Okay, I'm gonna trade this for something better." But I think the reality is, there is no, tsk, every relationship comes with challenges. It's just a question of which challenges. Once you stick through all the hard moments, and you keep getting better and elevating, and then you look back, and it's like with my wife, it's just like w- what we said about companies. Like, all those challenges made us better. They brought us closer. We're stronger as a result. We're more resilient. You know, the other day, the other day, um, tsk, I got into a little thing with my wife, and she had this moment. She's like, "Oh, like, is this gonna always be a problem? I don't," you know, like, "Are we gonna get through this?" And everything. And I kind of looked at her, and I'm like, "You know, babe, we've been through way worse. We've overcome all these challenges, so the answer is yes." I mean, if this is like, you know, we've overcome every other challenge, every other moment where it's been like, "Oh, this is so hard," we've prevailed, and we've become better, so this is no different. So I think when you have that mindset, when you have the mindset that every challenge is working for you and is bringing you closer, I think that's when you grow. You can't grow without challenges. I mean, that's, that's kind of the thing of life. I mean, if it- if it was all rainbows and butterflies, what's the point?

    8. HSHarry Stebbings1:00:53

       Sex, honesty, trust, and laughter, the four pillars, sex, honesty, trust, and laughter.

    9. SRSean Rad1:01:03

       I think it's a good formula. I think that's a good formula.

    10. HSHarry Stebbings1:01:05

        Yeah. Where would you put one through four?

    11. SRSean Rad1:01:08

        To me, it's like one thing leads to another. When you have honesty, you have trust. When you have trust, you have laughter. When you have laughter, you have sex.

14. 1:01:18 – 1:05:53

    Reflecting on Spirituality & Thoughts on Mortality

    1. SRSean Rad1:01:18

    2. HSHarry Stebbings1:01:18

       Listen, dude, there's one thing I wanted to discuss before we do a quick-fire. And it's you said kind of cavalierly almost that things end, and it, it, it almost seemed quite natural. My question that I have for you is, how do you think about your own spirituality? How do you think about dying? Just talk to me about that. I think it's quite an important one.

    3. SRSean Rad1:01:39

       I'm gonna get really spiritual with you. I don't believe our soul dies. I think our soul carries on, and our soul through many lifetimes, including what we leave behind and the memories, we're sort of always contributing and always growing and always facing new challenges of elevating at maybe a soul level. Um, but our body dies. Our presence on this earth dies. But I think our soul doesn't.

    4. HSHarry Stebbings1:02:18

       Are you scared of that?

    5. SRSean Rad1:02:20

       No. You can't have light without darkness, and you can't have life without death. If you would never die, then what... And you're, then that means you're never willing to die for something, and that means you don't have a life of meaning. If you never have darkness, that means you're never overcoming anything and you're never risking, and you have a very bland, monotone existence.

    6. HSHarry Stebbings1:02:52

       Is dying for something the ultimate form of meaning?

    7. SRSean Rad1:02:56

       Standing for something and willing to take risks for what you believe in, and, and really love, I think the energy of that is love, right? So love is what makes me overcome obstacles, what makes me stick through. That, to me, is the meaning of living.

    8. HSHarry Stebbings1:03:15

       What was the hardest thing to stick through?

    9. SRSean Rad1:03:17

       Building a company is not easy. You have moments when you're getting crushed. Any entrepreneur knows this. When you're resilient-

    10. HSHarry Stebbings1:03:27

        Did you, did you ever have an 800-pound gorilla come into the room and outspend you?

    11. SRSean Rad1:03:31

        People tried, but money, money doesn't solve, money doesn't create innovation. I think if, if money resulted in innovation, then you would never have disruption. I think, so it's like just because you have more money doesn't mean you can beat us, because it doesn't mean you're the most creative. In fact, I would actually say sometimes constraints f- force creativity, forces you to focus, forces you to prioritize. When you're resource-constrained, you automatically don't do the shit you shouldn't be doing. You're forced to make a decision with your time, with your money. So I don't, I don't think necessarily more money. In fact, there's many startups that actually failed because they raised too much money, and they threw money at the problem or they threw people at the problem, and they didn't actually tussle or force themselves to think out of the box or get creative and find new ways to solve a problem. So I don't think more money necessarily solves problems.

    12. HSHarry Stebbings1:04:31

        Did making a lot of money change the dynamic of your relationships?

    13. SRSean Rad1:04:35

        Yeah, I think, look, it, it, I'm, I'm fortunate enough that I was able to navigate all of that and kind of, um-

    14. HSHarry Stebbings1:04:43

        Did you take money out of the way through Tinder? I don't mean that too invasively, but-

    15. SRSean Rad1:04:47

        A little, a little bit. We did, we did.

    16. HSHarry Stebbings1:04:48

        It wasn't like...

    17. SRSean Rad1:04:49

        A little bit. We, we took enough, and I'm a big believer in this, that, you know, if, if, you know, you should take a little bit along the way to live and be comfortable. The more you can create freedom, the more you could give to what matters, which is your company or your relationships. And, and sometimes money buys that freedom, and it allows you to sort of focus even more. So we did take money along the way, and our investors wanted us to do that, 'cause I think they realized that, that if we alleviated some of that pressure, then we can go even harder. Um, but we didn't take too much.

    18. HSHarry Stebbings1:05:29

        Sorry, I'm being specific, but a lot of founders go like, "I don't, I don't get it." Like, is 5 million in secondary for a founder too much? Would you say, "Whoa, Harry"?

    19. SRSean Rad1:05:39

        I think, I think the, the better way to think about it is in terms of percentages. Is 5 million too much if you have a billion-dollar company? No. Is 5 million too much if your company's worth 20 million and someone... You know, that's a different scenario.

15. 1:05:53 – 1:07:13

    The Biggest Misconception About Wealth

    1. SRSean Rad1:05:53

    2. HSHarry Stebbings1:05:53

       What do people not understand about wealth that they should do? Final one.

    3. SRSean Rad1:05:57

       I think if you're not careful... So first, first of all, wealth does not bring you happiness. Meaning brings you happiness. Wealth can create meaning up to a certain point, um, or it could give you freedom to sort of create meaning up to a certain point, but wealth on its own does not bring happiness. And I think the other thing people don't ask enough is, what is wealth? Am I, if I have great relationships in my life, I have a job that I absolutely love, I feel like I'm making a contribution to those around me, I'm giving, I'm living a life of meaning and purpose, am I wealthy? Even if I don't have a lot in my bank account, I would say, yeah, you're wealthy. So I think, I think people also have to question, what is wealth? Is wealth the Bugatti? Is wealth the yacht? Well, if the person sitting in the yacht has cancerous relationships and is secretly really lonely and isolated-... and has a lot of noise and has no freedom and no time to be thoughtful, then is that wealth?

16. 1:07:13 – 1:12:50

    Quick-Fire Round

    1. SRSean Rad1:07:13

    2. HSHarry Stebbings1:07:13

       I could torch you all day, but I do wanna do a quick fire round. So I'm gonna give you some-

    3. SRSean Rad1:07:17

       Let's do it.

    4. HSHarry Stebbings1:07:17

       Okay. So what do you believe that most around you disbelieve?

    5. SRSean Rad1:07:20

       That America is the greatest country in the history of all countries.

    6. HSHarry Stebbings1:07:26

       Do you think you are in a good spot right now?

    7. SRSean Rad1:07:29

       I think we're going through growing pains, but I think we're still the greatest country in the world.

    8. HSHarry Stebbings1:07:33

       (laughs)

    9. SRSean Rad1:07:33

       And that there's no, there's, there's... I, I, I know you're in the UK. UK is pretty great too. But-

    10. HSHarry Stebbings1:07:38

        No, no, no. We are an ailing economy that is slowly moving into complete irrelevance. But I l- find it funny because you wonderful Americans still love to spend your wonderful US dollars on our soil and go, "Ah, ............................" This is so nice.

    11. SRSean Rad1:07:52

        The UK, the UK is one of my favorite places in the world.

    12. HSHarry Stebbings1:07:54

        There we go. Yeah, we welcome you.

    13. SRSean Rad1:07:56

        Call it fair. (laughs)

    14. HSHarry Stebbings1:07:56

        We, we should just embrace hospitality as the only thing that we have and recognize-

    15. SRSean Rad1:08:00

        (laughs)

    16. HSHarry Stebbings1:08:01

        I'm being serious. Like, you know what? Fuck it. Just take everyone's dollars and get them all to come here.

    17. SRSean Rad1:08:06

        (laughs)

    18. HSHarry Stebbings1:08:06

        Um, but you feel America is in good shape? Do you think DEI is bullshit and the woke mind virus is this cancerous thing pervading society?

    19. SRSean Rad1:08:15

        Look, I think diversity is important. Diversity of perspective, diversity of thought. Creating an en- an environment that is meri- meritocratic is equally as important. And allowing-

    20. HSHarry Stebbings1:08:30

        Do you not agree that we have let diversity invade meritocracy? Now-

    21. SRSean Rad1:08:34

        I think we've had identity politics invade meritocracy. I think we wanna live in a society where I am judged not based on my identity, my age, who I am, but I'm judged based on my contribution and the merits of my work. And what's beautiful about tech and innovation is that you have an ecosystem, you know, where, in my case, you could be a young kid who's... Or in my parents' case, they came to this country with $20 in their pockets and had the opportunity regardless of their background to work hard and succeed, and that is the American dream that, that it's the underdog story that you can, you can overcome obstacles and pursue your happiness without your identity being a limiting factor. I don't think we're a perfect meritocracy. I think we need to improve our meritocracy and we need to have equal, more equal opportunity. Um, but I think equal outcome is a very bad thing.

    22. HSHarry Stebbings1:09:48

        What concerns you most in the world today, Sean?

    23. SRSean Rad1:09:51

        We lose... America's fragile. The ideals that built America are fragile. And that we easily take them for granted and we lose those values such as freedom of speech, such as free will, such as meritocracy.

    24. HSHarry Stebbings1:10:13

        Do you feel that you have freedom of speech today?

    25. SRSean Rad1:10:16

        I think we do have freedom of speech. It is under attack now. Whether people actually use their freedom of speech and feel safe to speak up is a different story. I think, you know, courage, courage is... You know, there's a great Winston Churchill quote. Um, "Courage is the strength to stand up and speak, but also sit down and listen." So I think we need more of that. We need the courage to speak up, but we also need the courage to listen. And one thing that is, that makes America the greatest country in the world is our openness to debate. And debate leads to better ideas and it leads to a stronger meritocracy. And when you have a cancel culture where people don't feel safe to speak up and speak their views or you have a culture where people don't, are not willing or tolerant of other people's views or sit down and listen, then the outcome's never gonna be great. We've seen that story before. I think something that scares me that, you know, we talk a lot about freedom of speech, but we don't talk a lot about freedom of free will. I think right now social media platforms are, to some extent, violating my free will by algorithmically picking what content I see and not giving me choice in that equation. It's the equivalent of turning on the TV and Comcast deciding what I see, but I can't switch the channel, can't switch from CNN to Fox News. There's no opt-out button. There's no opt-in button. When social media was a follower-based economy, I think it was a lot healthier of an ecosystem. This move to an algorithm-based economy has its benefits. There is some amazing things about that. But I think we are slowly sacrificing free will. And if you have free speech but you don't have free will, then there's no point of having free speech.

    26. HSHarry Stebbings1:12:24

        When I plot out 10 years, Sean, where do you wanna be in 10 years?

    27. SRSean Rad1:12:29

        Doing a job I love. Having (clears throat) meaningful relationships, family, um, children. Just having fun. Enjoying every moment, good or bad. Just having fun.

    28. HSHarry Stebbings1:12:44

        I can't thank you enough for being so open. This has been incredible and I really appreciate it.

    29. SRSean Rad1:12:49

        Thanks, buddy.

Episode duration: 1:13:00