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20VC: Tinder Founder Sean Rad on Lessons Scaling Tinder to the Fastest Growing Consumer Social App in History | Leadership Lessons Scaling Tinder | The Future of Love, Dating and Social Media | The Secret to Your Relationship with Money and Marriage
Mon, 09 Sep 2024
Sean Rad is the Founder and former CEO of Tinder. Sean has made more romantic connections between humans than anyone in history with Tinder having matched 50BN different people. Sean is also the Founder of Rad Fund which has made over 100 investments in companies and funds. In Today's Episode with Sean Rad We Discuss: 1. Lessons Scaling Tinder to the Fastest Consumer Social App: Starting: How did the idea for Tinder come to Sean in a restaurant in LA? Scaling: What are Sean's biggest lessons for consumer apps scaling to their first 10,000 users? User Acquisition: How did a party change the entire user acquisition strategy for dinner? What did Tinder not do that Sean wishes they had done? What did Tinder do that with the benefit of hindsight, they should not have done? 2. Leadership Lessons from Tinder CEOship: Annual Product Redesign: Why does Sean believe that every consumer company should have a complete redesign of the app every year? What are the benefits? Detachment: How does Sean advise founders when it comes to detaching their happiness from the performance of the company? What works? What does not work? Common Mistakes: What are the most common mistakes that Sean sees early-stage founders make when it comes to leadership? 3. Money, Wealth and Creating a Family Office: How does Sean analyse his own relationship to money? How has it changed over time? At what stage of wealth does Sean believe you have true financial freedom? What is the single best investment Sean has made? What did he learn? What is the worst investment he has made? What did he learn? What have been the single hardest and most surprising elements of creating a family office? 4. Love, Death, Marriage: In what ways does Sean think love has changed with time? How do we deal with the loneliness pandemic? What does Sean believe are the most non-obvious but important secrets to a happy marriage? How does Sean approach and think about his own spirituality today? Why does he not fear death?
Product market fit isn't one moment in time. Product market fit is a constant iterative process. When I 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. 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.
This is 20VC with me, Harry Stebbings, and what a show we have in store for you today. Sean Radd, founder of Tinder, the man who has facilitated more love than anyone else in human history. Did you know Tinder has made, check this out, over 50 billion, 50 billion matches. Truly insane. Sean is also the founder of Radd Ventures, which has made over 100 investments in both companies and funds.
This was such a fun show to do. We recorded one eight years ago or so and so this was very special to do again and you can find the video of the interview on youtube at 20 vc but before we dive in when a promising startup files for an ipo or a venture capital firm loses its marquee partner being the first to know gives you an advantage and time to plan your strategic response
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So to learn more about the number one most active law firm representing VC-backed companies going public, head over to cooley.com and also cooleygo.com, Cooley's award-winning free legal resource for entrepreneurs. You have now arrived at your destination. Sean, I am so excited for this, dude. I've been looking forward to this one for a while. So thank you so much for joining me today, man.
My pleasure. Happy to be here. Dude, it's been so long. I want to start with a bit of a kind of tougher one. You tie your identity to your company as a founder, and suddenly it's no longer part of you. How did you deal with that detachment from identity when no longer CEO of Tinder? Yeah.
It's really hard. In my case, I sacrificed so much. Not only it was my identity, 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 really existentially rocking to your core. How did I deal with that? It took me a while to recognize that is not my identity and that is actually not healthy to make that my identity.
And founders are better when their company is not them. Because it's not about you. It took me a while to sort of step away and see that. And actually reflecting back, our most successful moments 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.
You need to take the individuals out of it. That's when companies perform the best work. When there is sort of, 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.
Do you think that's the case for many companies today? 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.
You know, to me, leadership is when you sort of try to abstract yourself away. 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, shared your talents and empowered other people.
So I think truly great leadership, the greatest CEOs are the ones that are there, always available, killing, 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 can't have any individual be the source or single source of success or failure.
And you haven't matured the organization and that organization will never outlast you.
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, when we think about the inspiration, we forget today just how revolutionary the swipe was.
I might've been on a swipe swipe before this interview, which shows you the importance you have to pay if you want to be successful on dating apps today. But it was such an innovation. Tell me, what was the inspiration behind Tinder? And when you go back, what did that look like?
Before I started Tinder, I'd just sold a company and was thinking again, what is next? Reinvention. Around that time, 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.
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 heads down in their phone.
And so for me, 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 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 because 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. Now we can connect. That what we call the double opt-in was the revolutionary thought behind Tinder. Every system of connection prior to that was riddled with this emotional angst and barriers to connection.
Do you remember when you released it? Do you remember when you pressed go live? Yes. What does it look like from there? Does usage just go skyrocket from the moment you start?
No, no. So when we released it, nothing happens because no one knew about it. So it was a very anticlimactic moment. But what we started doing at a certain point, sitting with the team and it's like, hey, we built this great product. We know there's something special here. 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. And I think the thing that we texted was download this app and thank me later. Sort of wanted to create this like FOMO mysteriousness. And I think in total, we texted 500 people.
Over the course of a few days, we had, I think it was like 700 signups. I sort of looked at the team like, did anyone text anyone else? Like, 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 have never have existed if we removed these barriers. 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, shit, I never knew she liked me.
We never put two and two together. I'm going on a date with so-and-so. And it's like, whoa, 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.
That was the initial spark.
So we have 700 people and we have the initial spark and we start to see that outgrow from the core. What happens then?
Tinder was a relatively complicated product to market because it is very much location specific and you're building network effects, right? So the strength of the network, you don't want random people just sort of downloading that app and never opening it again. So you need a sort of strong connection amongst the network.
So we kept thinking like, what are areas where groups of friends or similar people sort of gather and congregate? And one of those are parties. And an intern of ours was in college at the time. And his friend who was sort of like one of the most popular people at USC was having a big birthday party. I think it was like a thousand people were invited to this party.
So we told her, we're like, look, we'll pay for the party. We'll throw the party. But in exchange, under one condition, 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 condition was that no one gets into the door unless they have Tinder on their phone.
So we literally had bouncers at the door, you know, whether you were 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 confirming this thesis. It's like, maybe there was that girl or guy that I didn't have the courage to walk up to.
Now I see them in the app and now I can swipe right and now we're matching. bringing people together and then empowering them through the app was a great marketing strategy. And that worked. Once we did that party at USC over the coming days, it went viral on campus. Everyone was talking about it and everyone was sharing it.
And we realized that was a great mechanism of when we introduce Tinder to the right groups of people, it takes a mind of its own. But I can't stress enough though, that none of that would have mattered if we didn't build a great product. Marketing is important. This is another thing people sort of miss. They think like, all right, I need to figure out how to get it out there.
But they don't spend enough time focusing on whether or not they have the right thing to promote.
Let's just delve into that then. It's on the product. But first of all, we do distribution. A generation has been told about the lean startup. Just ship, get it out there, see what works. Oh, A lot of other people say, no, actually, you need to be a lot more of a craftsperson and really build a great product experience and be very deliberate about it. Which side of the fence do you sit on?
First of all, you got to 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. Have to be the customer because 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 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 network of close customers, Then I think you slowly start expanding it. But it's the idea of throwing shit at the wall and seeing what sticks is a very soulless effort. I don't subscribe to that.
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 in every step. So product market fit isn't one moment in time.
Product market fit is a constant iterative process because as the product grows, it sort of faces new challenges at scale. And just because it worked with a thousand people doesn't mean it'll work with a million people. The idea of MVP, one thing people really miss in MVP, 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 you haven't achieved that, then whatever data you're getting is corrupted data to begin with. And another thing I'll say, we always believed in this, you know, Tinder, we always believe we have one shot. There isn't a second chance with users.
We have one shot to impress them. So we have to make that one shot count. And we would not take that shot until we're very ready. The sort of lean startup throw shit against the wall, I think lacks a little bit of soul.
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?
It was 100% about connecting you with someone and you walking away with a meaningful experience.
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... I think you want to 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. Because that problem that 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, I think even more so now, a little isolated.
They wanted new connections. They wanted to meet someone for whatever reason, marriage, friendship, whatever. 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're 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.
The sort of marketing message that we would always repeat is find out who likes you. Is that FOMO? Who likes me that I don't know about? So that was the hook. 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 have.
How did you define a retained user? You know, at Facebook, they said like after five friends have been added, we count that as like a retained and activated user. How do you count a retained user?
The thing that we really focused on is how many conversations we could drive. So, you know, there's swipe, match, talk. The ultimate value proposition is that you're in a dialogue. So the number of unique conversations we were driving was one of the metrics we would look at a lot. We did look at retention in the sense of what was DAO to MAO, MAO to, you know, WOW to MAO.
But over time, those metrics became less important. The metrics that became more important were 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, it is a problematic metric that could lead sometimes if you're not careful to a lot more harm than it can do. How so?
Because I think when you're focused on retention and you believe that retention equals value, you can sometimes delude yourself. Me spending hours doing something doesn't mean I extracted true value in it. I could spend hours getting high. Doesn't mean that's valuable in my life.
You know, so drugs have a great retention and they're really good at retaining people, but are they actually driving meaningful value? I would argue no. 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. So we were always very careful.
Like there was many times a desire to look at retention as sort of the end all be all metric. And by the way, we have fucking phenomenal retention. 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 watching content. You were actually connecting with human beings.
And I think to me, all we have is connections. All the other shit is just noise. All we want 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 in fact, while I was there, 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 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. Technology becomes, I think, the better it gets, the more human it gets.
And to me, the ultimate archetype was the matchmaker. Could we achieve the success of the human brain matchmaker who was able to say, Harry, here's the girl for you. Again, I'm not going to judge what you want to do. I'm just going to introduce you guys. You can do whatever you want.
Once the core team left, I think that promise, that mission was maybe replaced with a desire for retention, a desire for revenue. The sort of intention of why we created that company, 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?
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. The products today, as we said earlier, unless you pay, they're pretty horrible. And you hit paywalls. I mean, they're just bad products unless you pay. And then when you pay, it opens up. But is that just inevitable? Yeah.
Look, you could make the argument that everything dies. It's just a question of when. Companies are organisms, just like humans. Humans die, companies die, and it's just a question of how long. And 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, 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. Or you're not intellectually honest and you're not forcing yourself to disrupt yourself and question the mission and improve it. So I wouldn't say it's inevitable.
I think we've had organizations that have outlasted my lifetime, your lifetime. Maybe they'll outlast my kid's 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.
Before we talk on nothing is forever, which I have to touch on, because you said that in a kind of wonderfully calm and cavalier manner. 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?
To me, founders are really good at keeping and reiterating the mission because they care the most. Sometimes founder market fit, team market fit is essential. When it is your personal story, which it often is for founders, 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 have people who can come into an organization with a new vision, a better vision, and I think you would call them a founder.
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 a point, your exec team came and said, well, if he's not in the role of CEO, we're leaving. Right. Which is quite a jarring position for anyone to be in. Can you just take me to that?
What happened? So there was a moment in time where I think Tinder was growing so fast.
When you say growing so fast, what was that? Users? What sort of scale?
Users, revenue. 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. If you charted the growth rate we experienced 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.
Now, obviously we didn't sustain that growth rate, but the product was growing fast. The organization was growing fast. Revenue was growing fast. 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 felt 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 very, very experienced people person. And I think the board sort of, 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 because 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 where I kind of stopped being in the room for a lot of those other functions, it created a lot of issues in the Yeah, I don't know if this is about me or maybe the other person wasn't that good. But at one point there was like mutiny.
We had the entire executive team. I don't talk about it, but since you know the story, I'll say, I don't know how you sound now, by the way. We try not to talk about this. But there was one point where... The entire executive team, unbeknownst to me, went to the board and basically said, if Sean doesn't come back in the CEO role, we're all quitting. I found that very flattering.
I think definitely like a crazy moment for me personally. The translation, what I took away was that the team was saying that product management 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 give a little more love to this part of the organization and as a leader outsource another part of the organization. And I think the truth is that the learning that I had is everything matters equally. You know, unfortunately, the team didn't come tell me that.
They sort of just threw up their hand and said, come back or we quit.
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?
Yeah. So international expansion was one of the hardest things 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.
What was the strangest product alteration that you had to make?
I'll give you two stories. In Korea, group dating, that's like the socially accepted norm. 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 need to like really think about that experience, like reorient Tinder as a group dating, not as a individual dating.
But then what was interesting is we, as we reoriented that, it got us thinking like, well, could that be a thing everywhere else? Maybe that's actually more effective means of connecting. So can we bring group dating? Can we make that a thing? Can we make that easy? I mean, naturally, a lot of 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 relationship. So that was one thing that was interesting to tackle. Another thing was that in India, it was not really a system of dating and marriage that was 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 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 law. So that was actually sort of a moment where like, no, we're not changing the product, even if it means we're going to have less users because it was socially less acceptable.
So it's like unique things like that, where it's like, wow, the social norms and the dynamics are completely different.
Okay. In hyperscaling, you have so many decisions coming at you so fast. What did you do that you wish you hadn't done?
I'll give you two lessons there. I would say the Tinder team was maniacally good about focus and prioritizing and saying no and keeping the product simple. We believed in simplicity. I think if you look at the Tinder product, it's very simple. I would always reiterate the Albert Einstein quote, which is like, if something isn't simple enough, it's because you don't understand it enough.
The more you get to the essence of something, the simpler it actually becomes. And it's like fools make things more complex. So prioritizing and picking our battles was very critical. That became a little harder as we scaled. In the early days, we were very much one team, 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 our server 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 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. We had an environment where we really wanted to give people freedom to execute. Like I hated the top-down bureaucratic approach to creation. 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 going to 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 merit, meritocratic culture. 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.
As you scale, you have to build new systems to protect against drift.
What was the thing that didn't work biggest? And what did you learn from it?
In the early days, very few people know this, but we had every user sort of got to a 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.
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 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. And we all love 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 romantic connections. Maybe you can add your friends and you can share moments with your friends.
So we started, 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, 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. 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 wants to swipe and match and make new business connections.
And so that was a real realization, actually, that that wasn't what people came to you for.
Yeah, it was a reminder. I think the more we scaled, 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. It's like even when Steve Jobs left Apple and he came back, what did he do? He killed a bunch of products because 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 fall in this trap of, oh, we could do more things. But you have to stop and ask yourself, just because we can, 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 going to change that vision, there better be a very good reason. And it's got to be bottoms up. It's got to be start with because your users are asking for that. None of our users ask for a friend-making app or a business-making app.
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 can spend a lot of money on paid.
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 link.
So we wanted to have this signal that you're not just someone I swiped right on, you're extra special. 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 this strong connection. I really like you. Like there was sort of like the next level of romance.
That was what the super like was. But if we actually gave it to free, it would have no value. So we gave one free to everyone. And then we charged if you wanted to super like again. 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. 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.
The free is smart because it removes the desperation. The hard thing is you don't want to be 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 going to get?
Look, I don't subscribe to anything that's elitist. I think in many ways, a lot of these dating apps are elitist. 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? Actually, I'm not even sure that's good for women. It was always a weird concept. I'm like, what?
It was a good marketing gimmick, but 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, you know, fuck that. Tinder was always, you're yourself. We're going to find and match you with people who love you for you. And everyone...
deserves love and everyone deserves a match. We wanted to solve core human issues. We didn't want to give a leg up to one group or another group. Are you proud of the Tinder product today? I haven't been there in a long time, so would I look at the product and say I'm proud of the existing iteration of the product?
I think I would look at the product now and say, fuck, all the missed opportunity, because when the core team, when I left and then others left, there was a lot of unfinished business. We had a roadmap that I would say was like, 10 years long, we knew once we achieve this, it's going to open the opportunity to this. It's going to 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 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 a bit. brilliant to exercise because it kept taking it to the next level. The energy, the passion, maybe isn't as strong as it was in the early days, but that's also, again, natural course of business as you scale.
Do you agree with Whitney's take that we're going to have essentially AIs talk to each other, coalesce, see if you like me and I like you AI, and then we both like tennis, form a match? Is that how we'll have like a virtual dating self? Yeah.
That is a very sad idea. 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. I think abstracting away the journey is the stupidest idea I've ever heard. And you learn a lot of that journey.
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.
I didn't have money when I grew up. And I read on the tin that when you got money, you would be happy. I got a little bit of money, 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?
Number one, you said it, money does not buy you happiness. I think up to a certain point, 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.
At what stage does it complicate? Because at some stage you have to have a family office and then you have to have people to manage your family office and then taxes become a complete nightmare and all of this becomes chains.
For me, and 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. I don't value those things. I don't care about a yacht. My friends are my childhood friends. Building, creating products, solving problems is what makes me happy.
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. When I achieved 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 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 at a moment in history where regardless of your wealth, by any means, we are all way wealthier and have access to way more resources than previous generations, which also has expanded the options and possibilities and who we can become.
Do you think that's actually the case? I'm sorry, I don't mean to be provocative, but when we look at the price of food today, when we look at the increasing homelessness, when we look at the increasing levels of drug addiction, does it not feel like the standard of living is getting much better?
Yeah, we can get... No, no, I didn't say the standard of living is getting better. I said our access to resources are getting better. 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 it's just one page of something that's highly curated.
In a world where more than ever, any time 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-explore.
Or you can look outward and replace it with a bunch of noise and shit that actually distracts you from answering that question of meaning. In a sense, that's why I say, you know, kind of getting what you want can create the next challenge. Life is a journey of challenges. There's never, you're never going to get to the end of the road. Yeah. I think I'll just buy the Bugatti.
Yeah. Much better.
You'll buy the Bugatti, you'll enjoy it for two weeks, and then you'll get over.
I won't actually, because I'm legally not allowed. I'm not allowed to drive, Sean. So I'd have to sit in it stationary, but I wouldn't enjoy it. So then you decide, okay, I'm going to do a family office and I'm going to invest a lot more work, a lot more hands-on with many more companies. Yeah. Why, why not do another company? You said you had a 10 year.
I've done both. So I have a family office where we've invested in over a hundred different companies and funds. And I enjoy that because it, it allows me to meet other great entrepreneurs and to give back, to mentor, to learn myself. But at heart, I'm a builder. I'm a problem solver. That's what gets me up in the morning.
I don't talk about it because I don't want to, I've started four companies since Tinder, but I just kind of purpose. I think I kind of learned like it's a little easier to build without a lot of attention. Post-success, do you have a lot more leverage? Anyone who has accumulated experience and wealth also accumulates freedom and leverage, no matter at what stage.
So of course, I would say I have more options. I can think bigger.
And so you have a CEO for each business. Yes. That runs day to day, and then you finance and do strategy with them.
Yes. I think it's a really rewarding position to be in because I can focus on strategy and trust others to run the business. It 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, but I've found a lot of meaning in building. So I'm not going to stop building.
What were the biggest lessons you had in setting up the family office?
Investing is hard and it's a full-time job. Investing requires a lot of discipline. It requires you to really experiment, understand what works for you. 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. So, you know, the family office is no different than building a company. We're just in the business of investing.
Did you have a clear strategy from day one? I'm going to put 25% in directs, 25% in funds, 25% in cash, 25% in property?
I had a high level vision, but I was also, I iterated the more I learned. What did you start with and what did it change to? Most of what the family office does is we invest a lot in real estate because I think real estate is an amazing asset class. We invest a lot in venture that's direct or through funds. And we invest a lot in public equities. We invest a lot in credited debt.
There's 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. 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 morphs as new opportunities present itself.
But for the most part, it really is following passion and love and the things that I enjoy working on and I want to work on and I want to spend time on and eliminating distractions as much as possible. What's been the single best investment? Probably SpaceX. Invested a lot in SpaceX very, very early. That'll do it. The thesis there was actually very simple. It was, I admire Elon.
I think he's a once in a lifetime entrepreneur. I was just willing to let him invest my money.
What was the worst investment and lessons from it? If you don't want to say what it actually was, by all means, but what were the lessons from it?
The worst investments were when I chased the idea and not the team. So there were moments where I'm like, fuck, this idea is so good. I'm not really sure about the team. Like, do they have the...
passion the energy to go and execute is their heart really in it and i kind of ignore those elements because i'm like oh idea is so good i don't want to miss out and nine times out of ten never works so the number one thing is team and passion i think you want a team that 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. Teams that are humble, self-aware, are able to recognize when they made a mistake and adapt versus constantly make excuses. This didn't work out. Let's blame the market.
Let's blame the circumstances rather than let's look at it. Will you invest in someone you don't like? Not anymore. Why not anymore? Because it just never works out. I think I have 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 the energy that I think produces the best outcomes and the greatest results.
Good segue. Thank you for that. That's very nice. You team me up perfectly because I think you literally must have facilitated more love in the world than anyone else in human history. 50 billion matches, according to your Twitter bio. 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. It is very, very hard. Relationships, I think, force you, when they're good, to become better as a person. But in order to become better, you got to stick through the hard times, not give up. Do you think we give up too easily today? 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.
You go back in some moment of time, it's like you were in a tiny little village. If you're lucky, there was one person that you loved and cutting bait. I mean, where were you really going to go? You've had to stick through it. Now you could quit and you could say, okay, I'm going to trade this for something better. But I think the reality is 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 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. The other day, I got into a little thing with my wife.
She had this moment. She's like, oh, like, is this going to always be a problem? I don't, you know, I'm like, are we going to get through this and everything? And I kind of looked at her. I'm like, 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. When you have the mindset that every challenge is working for you and is bringing you closer, that's when you grow. You can't grow without challenges. That's the thing of life.
I mean, if it was all rainbows and butterflies, what's the point?
Sex, honesty, trust, and laughter. The four pillars. Sex, honesty, trust, and laughter.
I think that's a good formula.
Yeah. Where would you put one through four? Sex, honesty, trust.
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. I wish I made lots of girls laugh.
Listen, dude, there's one thing I want to discuss before we do a quick fire. And it's, you said kind of cavalierly almost that things end. 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.
Well, I don't believe, 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 and elevating and maybe a soul level, but our body dies, our presence on this earth dies.
But I think our soul does. Are you scared of that? No. You can't have light without darkness. And you can't have life without death. If you would never die, then that means you're never willing to die for something. And that means you don't have a life of meaning.
And 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.
Is dying for something the ultimate form of meaning?
Standing for something and willing to take risks for what you believe in 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. What was the hardest thing to stick through? Building a company is not easy. You have moments when you're getting crushed. Any entrepreneur knows this.
Did you ever have an £800 gorilla come into the room and outspend you?
People tried, but money doesn't solve, money doesn't create innovation. 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... force creativity, forces you to focus, forces you to prioritize.
When your resource constraints, 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 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 and 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 the problem. So I don't think more money necessarily solves problems.
I agree with that completely. I think it also makes for problems in relationships. Did making a lot of money change the dynamic of your relationship?
I'm fortunate enough that I was able to navigate all of that and kind of... Did you take money out the way through Tinder?
I didn't mean that too invasively.
A little bit. We took enough, and I'm a big believer in this, that take a little bit along the way to live and be comfortable. I think the more you can... create freedom, the more you could give to what matters, which is your company or your relationships. 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 because I think they realized that, that if we alleviated some of that pressure, then we can go even harder. But we didn't take too much.
Sorry, I'm being specific, but a lot of founders go like, I don't get it. Like, is 5 million in secondary for a founder too much? Would you say, whoa, Harry?
I think 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 is worth $20 million and that's a different scenario?
What do people not understand about wealth that they should do? Final one.
So first of all, wealth does not bring you happiness. Meaning brings you happiness. Wealth can create meaning up to a certain point, or it could give you freedom to sort of create meaning up to certain points. But wealth on its own does not bring happiness. And I think the other thing people don't ask enough is what is wealth?
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 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. I think people also have to question what is wealth? Is wealth the Bugatti? Is wealth the yacht?
If the person sitting in the yacht has cancerous relationships, 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?
I could talk to you all day, but I do want to do a quick fire round. So I'm going to give you short. Okay. So what do you believe that most around you disbelieve?
That America is the greatest country in the history of all countries.
Do you think you are in a good spot right now?
I think we're going through growing pains, but I think we're still the greatest country in the world. I know you're in the UK.
UK is pretty great too, but... No, we are an ailing economy that is slowly moving into complete irrelevance. But I find it funny because you wonderful Americans still love to spend your wonderful US dollars on our soil and go, ah, Hermes on Bond Street.
UK is one of my favorite places in the world.
There we go. We should just embrace hospitality as the only thing that we have and recognize... I'm being serious. Like, you know what? Fuck it. Just take everyone's dollars and get them all to come here. 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?
Look, I think diversity is important. Diversity of perspective, diversity of thought, creating an environment that is meritocratic is equally as important.
Do you not agree that we have let diversity invade meritocracy?
I think we've had identity politics invade meritocracy. I think we want to 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, 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.
It's the underdog story that 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 more equal opportunity. But I think equal outcome is a very bad thing.
What concerns you most in the world today, Sean?
That we lose America's fragile, the ideals that built America 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. Do you feel you have freedom of speech today? 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 courage, there's a great Winston Churchill quote, 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 makes America the greatest country in the world is our openness to debate. And debate leads to better ideas. And it leads to stronger meritalkers.
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 are not willing or tolerant of other people's views or sit down and listen, then the outcome's never going to be great. We've seen that story before.
And I also think we're losing, 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, 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.
When I plot out 10 years, Sean, where do you want to be in 10 years? Doing a job I love.
Having meaningful relationships, family, children. Enjoying every moment, good or bad. Just having fun.
Dude, as you said, there's not many questions that I haven't asked here. I can't thank you enough for being so open. This has been incredible and I really appreciate it. Thanks, buddy. This was really fun. Now shows like that are why I love doing what I do. I interviewed Sean many years ago, we stayed friends, and having the ability to have that great conversation is just really special.
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