#41 - Dating app that has an admissions process like Harvard

** In our Facebook group yet? We hang out there so come join and let's talk ideas: www.facebook.com/groups/ourfirstmillion ** Amanda Bradford (@amandabradford) was 28 years old, in business school and using dating apps. She got tired of stalking every match on Linkedin, Facebook etc.. to see if they were legit. Why doesn’t the dating app do this for me? So against all her advisors advice, she started a dating app called the League that checks your Facebook & Linkedin to verify that you are who you say you are. Strange idea, but It’s kinda working! They have over 100k paying members, profitable & been around for 5 years. We talk about: how she got her first 400 users at launch, how they figured out if people would pay $$ for subscription and what the future of dating looks like. See acast.com/privacy for privacy and opt-out information.

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

• 0:00Shaan Puri?

  What's up guys, Sean here. I got a couple of announcements for you. So we'll start with a little celebration. We crossed the 1 million download mark, which is amazing in just, I don't know, six months that we've been out. So that's kind of incredible. Didn't think it would get this far. Obviously, you've got a long way to go. In the words of Dr. Disrespect, "We're all the way at the tippy top of the mountain, but we're only halfway up." Okay, so a couple of other announcements. We've been doing these brainstormers, me and Sam from The Hustle, and they've been a lot of fun to do. Plus, I think, seem to be the favorites from listeners, more so than the interviews even. So, we actually are gonna do what, you know, most projects and startups should do, which is follow the demand. So, those episodes are the ones that get the best feedback, they get the most listens, and they're the most fun to do.

• 0:43Shaan Puri?

  So we're gonna double down and do more episodes of that style. So we'll still bring in awesome guests who can tell us about their company and how they did it. But in fact, we're gonna invite them in, instead of saying, "Hey, tell me your life story", we're gonna spend the time with them, saying, "Hey, okay, you know, how did you do what you do? And what else do you see out there? Brainstorm with us." And it'll be more casual, and I think it'll be interesting to see what really smart, successful people who are, you know, they're operating their company sometimes for 10 years, but they see all kinds of other opportunities that they can't go chase. And they have this list of ideas that, you know, they'll never get to. And so I wanna see that list of ideas. I want them to come share that on the podcast. So, going forward, we'll be doing more episodes like the brainstormers. Hope you guys like that. Okay, so those are two announcements. And then this episode is with Amanda Bradford from The League.

• 1:28Shaan Puri?

  The League is a dating app. She built this app because, to solve a very simple problem that she was having, she would match with somebody on a dating site, like OkCupid, or Match, or Tinder, or whatever. And before actually going to meet the person in real life, she wanted to know, "Is this a real person? You know, is this person, is this person who they say they are? Do they have a job? You know, I wanna kinda know about this person beforehand." And she wished that the dating sites would sort of vet the people in the dating pool, but they didn't. They just wanted to grow at all costs. So they didn't care. You can make as many accounts as you want. And so she created a dating app that would vet people. It has an admissions process, sort of like you're applying to Harvard, but like, cool company. And it was a fun conversation.

• 2:08Shaan Puri?

  So, hope you enjoy this episode. This is probably gonna be the last one like this, or at least on a regular basis where it's, hey, it's all about our guests telling their story from, from sort of start to finish. And going forward, we're gonna be doing a lot more brainstormings with me and Sam. Hope you guys like that. One other thing, the Facebook group is popping off right now. I think I just approved 100 members to get in. So if you go on Facebook and you just search "my first million," it's called like "my first million startups, investing and side hustles." And it's basically just a community of people who are hustling to make, you know, get businesses off the ground and make their first million. And I like it. I don't even, I mean, I'm in there as a participant. Some of the guests from the podcast are in there as participants, but it's just a cool community of listeners. Okay, that's it for me. Enjoy this

• 2:52Shaan Puri?

  episode. Thank you for getting to, getting us to the 1 million mark. And yeah, we're only halfway up.

• 3:01Shaan Puri?

  So you're here, you, we, I don't even know how we got connected. I think we got connected on Twitter.

• 3:05Speaker 01

  Yeah, I'm not, you're one of my few Twitter friends.

• 3:08Shaan Puri?

  You don't have that many Twitter friends?

• 3:10Speaker 01

  No, I was one of those people that started and only followed a couple of different people that were in industry leaders. And so I don't have like regular friends.

• 3:20Shaan Puri?

  I make all my friends on Twitter. In fact, I told Sam this, I, um, once a month, we'll just host a dinner, just to people I've only known through Twitter. I'd never met them in real life.

• 3:29Speaker 01

  Oh, that's cool.

• 3:30Shaan Puri?

  And those have become some of my like, good friends now. But that's like-

• 3:33Speaker 01

  Twitter tea party.

• 3:34Shaan Puri?

  Yeah, that's a good one. Yeah, we call it the Twitter dinner, but maybe Twitter tea party is better. Okay, so Amanda, you're here. You're the founder of The League. So, we're gonna go all over the place in this conversation, but let's start by giving people a sense of who you are, what you built, and what, what makes it interesting. So, so give us the rundown.

• 3:51Speaker 01

  So I created The League, which is a dating platform, now a community, really, because we, we do actually work for single and non-single people. Like, um, at this point, most of the users are single that use The League. It's so, first and foremost, it is a dating app. Um, and the concept behind it was really focused on designing it for a career. ...oriented, ambitious people that didn't have a lot of time on their hands and didn't really want to play a game of Angry Birds every time they wanted to go on a date. So it was for the people that

• 4:20Shaan Puri?

  A game of Angry Birds?

• 4:20Speaker 01

  It is like, well, you know, most dating apps were so gamified and they're all there to drive engagement numbers through the roof. And then, you know, a lot of them were doing advertising revenue models at that time. So they were really incentivized almost not to help you find a date, really to help you just keep swiping. So I just felt like it was so much time to even use these dating sites and most of them were really bad. And the people I met, it wasn't so much even that the people on the dating apps were bad. It was just the, the way it was designed was not designed for efficiency at all. And so I felt like I could just redesign it. And so I started thinking about it and wire framing it. And then I was graduating business school and I decided I might as well just try building it and at least it could work for me.

• 4:59Shaan Puri?

  So

• 5:00Speaker 01

  Dating app for one.

• 5:02Shaan Puri?

  So you started this back when, uh, how many years?

• 5:05Speaker 01

  So now five years ago.

• 5:06Shaan Puri?

  So five years ago and fast forward to today, give us a sense of how's the business? Is it big? Is it small? Is it just getting started? You know, like, give us a sense of scale of the business so we can understand. You started there. How far has it come?

• 5:18Speaker 01

  Well, yeah, for, I mean, for a sense of scale, we started in San Francisco with 419 users. So, and that was November 2014. Um, and so fast forward, at this point, we're well over 100,000 daily active users and we're in 70 cities. We just launched Singapore, Mexico City, Australia. So we're now officially global. So we've, you know, but we went really slowly and carefully. Like we don't have a Snapchat, like trajectory curve. I mean, we, we really built each city almost by hand at the beginning and then automated what we had been doing manually. I mean, I remember in San Francisco, I was literally manually going through profiles and saying, okay, you put in a good profile, you're in, you're in, you're in. And like

• 5:58Shaan Puri?

  Cause there is like an

• 5:59Speaker 01

  Essentially being the bouncer.

• 6:00Shaan Puri?

  There's an admissions component to it, right?

• 6:01Speaker 01

  Yeah. So we, you know, the idea behind it was, hey, if we, all the users that have these half-baked profiles or are just window shopping or there to message you and catfish you or, you know, just kind of the crap. Users that just happen to to find themselves being drawn to dating sites everywhere. I mean, it's a problem in the whole industry. If we just screen them out from the beginning, then we don't have to worry about them affecting the user's experience. So we basically have this like very curated community of of people that actually want to be there, that want to find a date, that put a good profile together, that aren't lying.

• 6:30Shaan Puri?

  So is it fair to say you guys curate not just people that are real, but people that are also like professional and kind of have their shit together? Or it's not that part?

• 6:39Speaker 01

  Yeah, well, I mean, it's definitely geared for for those people that are like, look, I will trade time for money, and I do want a platform that will help me find my partner.

• 6:47Shaan Puri?

  And what does it cost?

• 6:48Speaker 01

  So we we have an admissions model. So if you put together a really good profile and sort of the community that you're applying to needs someone like you in the community, there, you know, we do put let people in for free. We call it a guest guest access. And then we'll also, you can pay to to kind of skip the line and get expedited review. And then we'll help those people put together a good profile, give them optimization. So it's kind of like, you know, you can pay to essentially, you know, have more visibility, be seen by more people. And then dating it ultimately is.

• 7:19Shaan Puri?

  Kind of like university, you pay a little bit, your kid gets in.

• 7:21Speaker 01

  Well, I would say it's more like if you are a mathematician and you recognize that, okay, only one out of three people that see you like you, and you only like one out of three people, then the more people that can see you, the number of choices you have go up. And so, you know, I think it's for a lot of, we call them hedge fund Harvey, but we have a lot of these users that that do the math in their head and are like, yeah, it's totally worth spending a lot of money for this because I'm saving myself so much time and I'm getting to see see my options, basically.

• 7:48Shaan Puri?

  And you were just telling me right before we started that you got engaged?

• 7:50Speaker 01

  I did.

• 7:51Shaan Puri?

  So the question is, was it?

• 7:53Speaker 01

  I'm officially off the market.

• 7:54Shaan Puri?

  Was it through the app? Or was was it, you know, real life serendipity?

• 7:57Speaker 01

  No, it was actually through the league. Like ironically enough, I was, we always joked that if it didn't happen through the league, I was going to have, you know, a hell of a time explaining it.

• 8:06Shaan Puri?

  Yeah, I was gonna say.

• 8:07Speaker 01

  No, I actually.

• 8:08Shaan Puri?

  It either was gonna happen through the league, or you were gonna lie and say it happened through the league.

• 8:11Speaker 01

  We were gonna have to come up with something. But, no, it actually did. I I met him in LA, so I joined the LA league. I decided to move my location, having dated in San Francisco and decided it was time for a little break.

• 8:22Shaan Puri?

  What was wrong with the San Francisco market?

• 8:25Speaker 01

  No, it was good. I just have been here, what, ten, ten years now at this point. I knew the market really well. And I felt like I was, I joked, I felt like I was, you're standing on the edge of the pier, seeing the boats come in, because I knew, you know, I'm basically running this marketplace, so I can actually see. And I was like, or I could go to LA where I haven't met anybody. And so it seemed like a

• 8:46Shaan Puri?

  And when you saw his profile, what'd you see? What cut your eye?

• 8:49Speaker 01

  Well, he's a musician, so he plays a guitar. And yeah, he has kind of a different vibe than, than what I was, I guess.

• 8:59Shaan Puri?

  Used to.

• 9:00Speaker 01

  Well, yeah, wanting to, to try something, I think, a little bit different than me. So we're, we are, we are very different, like on our Myers-Briggs, I don't think we're very similar. So we definitely complement each other. But I think that was part of, you know, part of what I love about the league and working in dating is that you're essentially like, working in human psychology every day. And so much of relationships is, is kind of about understanding yourself, and what you're looking for, and what your childhood patterns are, and what is like a healthy relationship. And so I think, I think the process of dating is actually quite therapeutic in some ways, so.

• 9:35Shaan Puri?

  Do you almost feel like you know too much?

• 9:38Speaker 01

  I think that, well, I know too much about the, like, the top of the funnel, if you will, of like, you know, how to optimize your profile, and how to make sure your league score goes, skyrockets, like, we all know at the, at the league

• 9:50Shaan Puri?

  What goes into that?

• 9:51Speaker 01

  We all know how to hack our own league profiles and stuff.

• 9:54Shaan Puri?

  Photo selection? What are the key things?

• 9:57Speaker 01

  Well, of course, it's always photo selection. I mean, the higher res, the better, you know, better looking profile you have, the more model-like the photo works, honestly, it's the better your score is, unfortunately.

• 10:08Shaan Puri?

  Did you see this?

• 10:09Speaker 01

  I always tell people, like, glamour shots exist for a reason, guys.

• 10:13Shaan Puri?

  Right, they work. Did you see this show that came out on Netflix called The Circle?

• 10:17Speaker 01

  No.

• 10:18Shaan Puri?

  All right, so, so Netflix is pushing this hard. So if you open up Netflix, you're gonna see the circle up top. It's basically their first game show. But what's interesting about it, what you said reminded me of it, is they put these eight people in a hotel. So they're all locked in their room, they can't go out, can't meet each other. But they each create a little profile. And so the first thing they do when they get to the room is they pick their profile photo. And and some people choose to catfish. They're like, you know, it's a guy, but he's playing.

• 10:42Speaker 01

  Yeah.

• 10:42Shaan Puri?

  He's playing his girlfriend. He's like, she looks so sweet. People here will like her. And so it's a game like Survivor, except you're not out in the wild, you're just locked in a hotel room. And all you do is you put up your profile with a couple of photos and a little status or a little tagline. And you message each other. And then every whatever couple of days you rank, it's like rank all the other players and who you like, who you want to keep. The bottom player gets ranked, gets kicked out. And so it's very interesting in this because some people were trying to choose like the model photo. Everybody listed themselves as single because they're like, look, people will want to engage a little more if I list myself a single. Uh, but it's a fun show and I feel like it'll be.

• 11:18Speaker 01

  Did they move around a lot through the weeks? Like were their first impressions?

• 11:21Shaan Puri?

  Yeah. So basically the first impression would be like, um, you know, whoever was at the top would go down. And actually the optimal strategy was sort of to flip by in the middle. So you weren't seen as too big of a threat like, because if you're too beautiful or too likeable, um, some people would have a strong first impression, either for or against you. But you were almost too polarizing. Like you wouldn't make it all the way to the end of the show. And, um, so that was interesting. I don't know. It's a bad show to be clear. It's a really bad TV show. But, uh, the psychology and as they're talking through like why I'm picking this photo, because I want to show this other side of me. Right? My first photo was really professional. So my second photo I need with my dog.

• 11:56Speaker 01

  You need to show, I always say.

• 11:57Shaan Puri?

  Yeah.

• 11:57Speaker 01

  Like show somebody else besides yourself in one of the photos that you care about something other than yourself.

• 12:03Shaan Puri?

  And what do you feel about like people who put a photo, like let's say, uh, uh, you know, I'm a guy. I put a photo of myself and another girl, but it's a friend. Uh, good move, bad move in a, in a dating app.

• 12:13Speaker 01

  I mean, if you, if you really don't have any other photos, it's better than not, you know, not putting it in. If it's a good photo of you and it's better than a, a bad photo of another one, it's still fine. But I, I would say.

• 12:24Shaan Puri?

  Not optimal.

• 12:25Speaker 01

  Uh, not ideal. Again, it depends on how much you're trying to optimize. You know, I think, I think one of the things people like about the league is that you kind of cut your teeth or dip your toe in the water on the Bumble or the tenders of the world and then you're kind of ready to join the league and like graduate to the league. And so people are really there and they're like, they have their shit together, they have their profile together, they want to meet someone, they want to go on like two dates, four dates a month. And they're kind of there for, not for business, that sounds wrong, but you know, they're there for a reason. And so I think that's what we find works really well in the league is when you make a profile that that sort of shows that, that you're taking it seriously and you have the high resolution photos, you've asked a friend with an iPhone to take portrait mode. I mean, it's not that hard, right? So just putting a little bit of effort goes a long way, I think.

• 13:08Shaan Puri?

  So what I like about what you're doing is, you know, there was always like this sort of serious platforms, like an eHarmony or a Match. And then there were sort of the very casual platforms. And the problem with the serious platforms was that they felt very old, outdated, and the seriousness was very much around marriage. Whereas sometimes you're looking for a serious person, but not necessarily like, I'm ready to be married right away.

• 13:32Speaker 01

  Right.

• 13:33Shaan Puri?

  And I think you guys found a sweet spot that's in the middle of the sort of ultra casual stuff and then the like, I'm ready to get hitched right away.

• 13:41Speaker 01

  Totally.

• 13:42Shaan Puri?

  Is that kind of how you thought about it originally? Or how did you sort of decide where to position yourself?

• 13:48Speaker 01

  I mean, honestly, I built it for myself, right? So I, I don't know if I mentioned that, but I, you know, I was using like Hinge and OkCupid and I remember I was writing support tickets, being like, you guys should really build this feature. And then, you know, so I kind of designed it based on my own issues. And at the time I was 28, 29.

• 14:05Shaan Puri?

  You were in business school or came out of business school?

• 14:07Speaker 01

  I was still in business school my last semester. And I was like, you know, having to drive an hour into San Francisco to go on a date. So every date I had to, you know, the cost was two hours of commute time. So these dates had to be good. So that's why I was like, looking at everyone on LinkedIn and trying to find their Twitter and being like, okay, if I cross-reference him in this and if he had, look at his Wikipedia page. So I was doing like, you know, legit stalking these people before accepting dates, which is work, right? So that was like, why can't the dating app just do that work for us? So, but anyway, so that's really who it is designed for is like, I wasn't necessarily ready to like go and get married, but I want to start maybe dating more seriously and maybe dating with the eye to think about someone that could be a fit for marriage. Like you're not 23.

• 14:47Shaan Puri?

  Yeah, a candidate.

• 14:48Speaker 01

  But you don't want to like be freaking everybody out by saying, hey, I need to be married in a year.

• 14:53Shaan Puri?

  All right, it's 2020, new year, it's gonna be a big year, and you know we had to come in with some new awesome partners. So for January, we are partnering up with Microsoft and My First Million. That's right, this episode is brought to you by Microsoft because whether you're just starting out or you're well on your way to your first million, Microsoft Teams can help your team hit the ground running with must-have features like real-time chat, editing, and video calling, all in one easy-to-use platform. Teams is a no-brainer at a price you can afford. Yep, there is a free version of Teams, as in it costs $0. See for yourself at aka.ms/thehustle. Again, that's aka.ms/thehustle to check out Teams, brought to you by Microsoft.

• 15:35Shaan Puri?

  Love it. Microsoft, that is a trillion-dollar company, right? We're talking about My First Million, they're on My First Trillion, so that's goals for everybody. They got there because they build epic products, Microsoft Word, Excel, PowerPoint, these are products that stand the test of time, and now they've come out with Teams to help teams chat, communicate, and work together, and I think it's awesome. All right, great, let's get back to this episode.

• 16:01Speaker 01

  So yeah, I wanted to kind of make it more of a community, that's why I always say we're a community and not a dating app, because, you know, we also have like groups and events, like you can be in the yoga group, or the dog, people with dogs, and the surfers. And so it's, you know, not that that's like a giant use case that's necessarily taking off, but I think the point is, we want to be more like a local kind of social network that is very, very social people, which happen to be often single people, but offering more of that kind of in real life. And that's what I love about what we're doing with this video chat, is that we're actually putting people on live video together.

• 16:36Shaan Puri?

  Tell people what it is, what's it called, what's the feature called?

• 16:38Speaker 01

  So we're doing two different things that are kind of both designed to get people closer in real life. So one is through video, and it's basically kind of like Chatroulette back in the day, but you know Chatroulette was super random, and you would just be paired with anyone in the world, like any... Any age or anything.

• 16:53Shaan Puri?

  Every third person was naked.

• 16:55Speaker 01

  Yeah, exactly. And I heard that that happened too. So basically, we actually take your preferences into account. We know your voting history. We know who you've liked, who you've matched with, and we essentially put you into the same pool and match you in real time with someone that we think is going to meet most of your preferences.

• 17:10Shaan Puri?

  Others who are online right now.

• 17:11Speaker 01

  At 9pm.

• 17:11Shaan Puri?

  They have the app open at 9pm.

• 17:13Speaker 01

  Right.

• 17:13Shaan Puri?

  Everybody get on. It's a happy hour, basically.

• 17:15Speaker 01

  So it's kind of like serendipity in an app, in a way, because it's like, it depends on exactly what time you go that the, you know, then you'll trigger the algorithm to go search for someone. If the match score is a certain amount, you'll, you kind of will get matched up. But if your score isn't, you know, if you're not an acceptable match for each other, you'll keep looking. So it's like, it's kind of like taking what speed dating, those old speed dating restaurants and bars would host them and just have to do all this manual labor to like move people around. And now you can just do it with, you know, pushing a button. So I think that's going to be a huge trend. And then the other trend that we think is super interesting is getting people in real life offline at the same place at the same time and just helping them sort of navigate their social nightlife compass.

• 17:56Speaker 01

  So we call that like party scout, but it's basically if everyone's going to the marina on Thursday night, who's 28 and single, and, you know, in my city, maybe I should go to the marina instead of going to Hayes Valley that night or whatever.

• 18:09Shaan Puri?

  And so.

• 18:10Speaker 01

  Those are some of the like, I think, trends that will be coming down.

• 18:14Shaan Puri?

  That's where the puck's going.

• 18:15Speaker 01

  That's what I'm excited about, I guess. It's unclear how like much monetization that stuff happens, you know, comes with, but I think, I think that's where it makes sense. Technology makes sense as an application to solve a problem.

• 18:26Shaan Puri?

  Right. Yeah, I believe in that. I was, I lived in Australia back in the day and there was a dating app there or dating website, because this was sort of like, you know, smartphones weren't as big of a deal back then. And they did this. And I've always wondered why nobody else did this. So basically, the whole website was you were only matched with people who were also online right now. And people would naturally just get online kind of after work in the evening, these prime times.

• 18:48Speaker 01

  Yeah.

• 18:48Shaan Puri?

  And so you would see, all right, there's whatever, 42,000 people online right now. And you would just see people, you'd see a single photo of theirs and you start chatting with them. And you knew you were getting a response back right away. So like.

• 18:58Speaker 01

  It's like AOL back in the day.

• 19:00Shaan Puri?

  But you knew they're all trying to date, so you're not a creep for reaching out. Like, we're all here because we're saying we're trying to date. And so compared to OkCupid or Match, where you had to write, essentially write a letter and then wait. That was slow.

• 19:11Speaker 01

  Right.

• 19:12Shaan Puri?

  Even the Tinders, you still sort of wait for matches and then kind of come back later. This was like, it was exciting. You would get online and you'd be like, oh, it's gonna hap- I'm gonna meet, I'm gonna talk to a bunch of people right now. And so you'd start all these conversations. And then as the conversation was going good, they had this great feature where you would, the person could unlock more photos of themselves for you. And so it was kind of like, hey, I'm liking this, here's some more photos of me.

• 19:32Speaker 01

  I was like, take your clothes off.

• 19:34Shaan Puri?

  Yeah, but it was more photos, right? So, uh, yeah, and the last photo, who knows what's in that last photo? But I always liked that because it was like these little indicators of interest that you usually don't get online. With video chat, you sort of can see their face, you can see if they're into it or not. They can swipe away and leave if not. But I love this idea. That's kind of my long-winded way of saying this. I've always wondered why more people don't try this, like synchronous.

• 19:53Speaker 01

  It's hard. I mean, you have to have a, you know, our user base is small comparatively and it's hard for us. I can't imagine a startup doing it with no users because it's, you know, it's hard to get even, even the people. So we have the, like, the concept of an RSVP that, that they're gonna go. And then the concept of like, who actually shows up at nine?

• 20:10Shaan Puri?

  Twenty percent or thirty percent.

• 20:11Speaker 01

  Huge flake rate. It was like bigger than, you know, and I run events for a living and I've seen flaky people in San Francisco for sure. And it was like, you know, fifty percent flake rate. So I think it's hard to get just to get it.

• 20:22Shaan Puri?

  You need density.

• 20:23Speaker 01

  Building a user behavior, right? And we'd have to start training our users. But they are starting to come in at nine. And, and I do think, um, you know, it is, we are growing slowly the future, but it is scary for people, I think, to be like so exposed for two full minutes.

• 20:38Shaan Puri?

  So let me ask you, you come up with this idea in business school, like many people do, and, uh...

• 20:43Speaker 01

  An MBA with a PowerPoint.

• 20:44Shaan Puri?

  Yeah.

• 20:44Speaker 01

  Or Google Slides now, yeah.

• 20:46Shaan Puri?

  Unlike most people, you decided to do it. So let's go slow through the steps, so...

• 20:51Speaker 01

  Despite every single sane person that I respect telling me not to go into the dating space.

• 20:55Shaan Puri?

  Right, so first tell me this, you have this idea, who do you bounce it off of? Friends, mentors, who, who do you bounce it off of first?

• 21:00Speaker 01

  Oh, everyone, tons of classmates, tons of, uh, my professors, yeah.

• 21:04Shaan Puri?

  And the reaction you're getting is what?

• 21:05Speaker 01

  Run.

• 21:06Shaan Puri?

  Dating is too hard.

• 21:06Speaker 01

  Run away, do CRM.

• 21:08Shaan Puri?

  Yeah.

• 21:09Speaker 01

  Cause I, I worked at Salesforce, they're like, just what, what, you're such a great girl, why don't you just go B2B? Don't do consumer, cause, you know, consumer is so, so fickle, it's hard, you don't, there's not a playbook as much as there is in B2B.

• 21:21Shaan Puri?

  And so what made you, do you remember the night or the day where you were like, screw it, I'm gonna do it anyways?

• 21:27Speaker 01

  I mean, no, I started, well, I decided that I was going to build it anyway. And worst case, it could just be a side project while I go get a regular job. And then I decided to, one of my investors said he would give me 25K to put into it. So I decided that I wanted to launch it. And if I could launch it and raise at least 500K in funding, then I would do it full time. And that was the decision I made. So it was less, because I knew I wanted to build it anyway. And so it was more like, how do I evaluate if, because it's not even just, just when you build it, you don't know for sure if it's going to be a business that, that has legs. So I just wanted to, so I felt like getting funding was at least the closest signal I could do.

• 22:04Shaan Puri?

  And you're not a programmer?

• 22:06Speaker 01

  Um, not, I would say I'm more of a hacker.

• 22:09Shaan Puri?

  Okay, did you build the first version yourself?

• 22:12Speaker 01

  Uh, no, no, no, we had, I had an engineer build it and it was all front end and Objective C. I don't do, I don't do iOS.

• 22:19Shaan Puri?

  And so this was somebody you hired full time, is kind of like a freelancer? How did you get it built?

• 22:24Speaker 01

  Yeah, freelancer, Stanford undergrad who's looking to like learn, learn.

• 22:29Shaan Puri?

  So do you remember how much you paid for the first prototype, first V1? Because a lot of our audience is people who are, you know, in your shoes, they're in business school or they're thinking about starting something. And it's always these, and I'm going to ask a bunch of questions about the early phase, because this is where most people really want to know. And it's sort of like black box. It's like, so how much does it cost to make something like this? And how'd you get your first 100 customers? So those are the questions I want to walk through.

• 22:50Speaker 01

  Yeah, no, they're good questions. And, and I think people have crazy assumptions sometimes, but I think I paid him $4,000 a month.

• 22:56Shaan Puri?

  Right.

• 22:56Speaker 01

  And but I had, with that came him sitting next to me, working as an engineer. And I was the product manager and we worked side by side in a.

• 23:04Shaan Puri?

  And it took how long to get the kind of V1 ready?

• 23:06Speaker 01

  We, we started really working after I graduated in June and launched it by November. And he rolled off because we, you know, I just hired him to get the prototype out. And then I was going to, that was sort of our, our arrangement. And so he rolled off in December, so.

• 23:19Shaan Puri?

  So six months-ish?

• 23:20Speaker 01

  Yeah.

• 23:21Shaan Puri?

  And you said something about like 400 users in San Francisco. Was that the launch essentially?

• 23:27Speaker 01

  Yeah, that was our November 12 launch. I think it was 419 logged in and then it grew from there and-

• 23:32Shaan Puri?

  Who were those 419? Where'd you get 419 people?

• 23:35Speaker 01

  Oh, probably my Stanford friends. It was like, it was basically like, I pulled every single person I knew at Google, Salesforce, where I used to work, Stanford and Carnegie Mellon. And so there was a lot of that. I think one of my friends joked when he opened the app, he was like, "You should just call this MBA date."

• 23:50Shaan Puri?

  Right.

• 23:51Speaker 01

  Because it was like, "Oh, I got Harvard MBAs, Wharton MBAs, because I threw a mixer that summer with the sole purpose of like, you guys are going to be my launch."

• 23:59Shaan Puri?

  Right.

• 23:59Speaker 01

  Kind of my launch, my launch team essentially. So it was definitely a lot of like 30-year-olds that were in the exact demo of what I was designing it for.

• 24:07Shaan Puri?

  Right.

• 24:08Speaker 01

  You know, looking to start seriously dating, but you know, not necessarily ready for like any harmony type of experience.

• 24:13Shaan Puri?

  So 419 people who you kind of sourced through your network, or the mixers that you threw pre-launch, they opened the app, and now does it sort of start doing anything? Or is it like kaput after the first one? You have to re- because many startups have to restart up, relaunch-

• 24:27Speaker 01

  Oh, yeah. No, we had tons. We have, I mean, I could do a whole podcast on like, mobile app nightmares. But, you know, we were using Facebook's Parse at the time, which has now been sunset, but it was like a giant, giant disaster, more or less, because after we got to a certain amount of users, the algorithm that we had built was actually on the front end of the code and essentially it would take almost five minutes to load your batch of potentials. So that was, that was a pretty bad situation where we actually couldn't put more users in for like a couple of months until we fixed that. But now, you know, we did, so we ended up rebuilding that app from scratch. But, but because of that, it's like nice and new and, you know, it was a year of like terrible construction, but then we, now we can be an international and we've kind of got all the scaling stuff

• 25:12Speaker 01

  done with it.

• 25:13Shaan Puri?

  And so, so from that first kind of November 12 launch, how long did it take for you to feel like, "Hey, this actually might work"? You know, "I'm not sure, but like, I'm seeing something that's telling me that this is working."

• 25:25Speaker 01

  Well, I think when people kept logging in despite having to wait five minutes, that was like one indicator.

• 25:29Shaan Puri?

  That's a good way to test.

• 25:30Speaker 01

  It was like, "Wow, we gave them a really crappy experience and they still came back." Because I think it was at the ultimate- At the end of the day, it was like we had people that were interested in meeting and that was, that was what we did really well. We curated an awesome group of people. So I think that was a big one. When we started, when people started referring friends, we had a pretty high, I think it was like 40% of people referring, which is quite higher than the average. And then I think what, what we also did, which I always tell people to do is, so my engineer, he wasn't a backend engineer, so he didn't know how to do any of the billing or payment stuff. But I wanted to know like how many people would pay or what percentage of people would pay. So we ended up building a feature and just saying, "Upgrade." And then we just told the user that we would charge their card, their card on a file with Apple, and they just push "OK." And so we ended up finding that we had like

• 26:15Speaker 01

  a 15% conversion rate on, you know, a membership without me having to actually sell

• 26:21Shaan Puri?

  Payments.

• 26:22Speaker 01

  Handle payments because we were not ready for that.

• 26:24Shaan Puri?

  That's smart. I like that.

• 26:25Speaker 01

  And then we didn't, we actually started monetizing in 2016 with the new app. And then that's when you start having paying customers, which was another milestone, which I was a little unprepared for. And that's when you really need a good customer support team. So that's when we started building out kind of our, our customer success in our concierge team.

• 26:43Shaan Puri?

  And so is the business profitable to be?

• 26:44Speaker 01

  Yeah, we just, as of, as of our end of year 2019 financials, we are officially profitable.

• 26:51Shaan Puri?

  That's amazing.

• 26:52Speaker 01

  Not taxable profit, but thank goodness. Yeah, but yeah, we did.

• 26:56Shaan Puri?

  Don't worry, the IRS doesn't listen to my podcast, so we're all good.

• 26:59Speaker 01

  I know. I'm like, not giving it to California yet. But yeah, so that was exciting because that was something that was important to me was to be able, I wanted us to grow, but I didn't want to grow at the expense of profitability. I just think in our space is, you don't have to. People are willing to pay in our space. And it's also just, it's a huge risk to the business. You can kind of be in this unsustainable position where you're spending money to, to keep your revenue at the same rate. But if you drop your marketing, your whole ship drops. And I, I've just seen so many horror stories. So I really wanted to, to both grow profit and grow revenue. And we were able to do both, which is exciting because it's easy to like grow revenue and you. Grow marketing.

• 27:35Shaan Puri?

  Right. Yeah. And if people don't know this, I looked, I think we'd launched a dating app. I ran this idea lab for five years. I think one of the things we launched was a dating app. And I looked into it and there's this crazy thing. I don't know how true this was, but something I had read at the time was all the, let's call it, you know, sort of generation one of dating apps that got big, all the sort of IAC owned apps like Match and whatnot. Their business model essentially was you, free account, but there was, they would sort of get you to message somebody and then, but if you wanted to reach out past a certain point, it was like, you have to pay or to receive your messages or to like read your messages, you had to pay. And so what they were doing was they were showing you matches of people who don't use the service anymore.

• 28:18Shaan Puri?

  And so like, let's say you see 30 profiles, 29 of those would be people who don't use the service anymore. Deactivated, inactive users, because they want to message that person and say, hey, there's a message waiting for you. Come back and check it. And for you, you're basically talking to a dead end and you don't realize it because they make it look active.

• 28:34Speaker 01

  Right.

• 28:35Shaan Puri?

  And so they're using you to like reengage their users because they're trying to get them to come back.

• 28:40Speaker 01

  Yeah.

• 28:40Shaan Puri?

  Check their inbox and pay. And

• 28:42Speaker 01

  And that's what they got in trouble for doing with the scammers too.

• 28:45Shaan Puri?

  Such a shady model.

• 28:45Speaker 01

  The scammers. They, they sent the scammers to the people who hadn't paid for memberships, but they didn't send the scammers to the people who already paid. And that's what they're getting sued for right now.

• 28:53Shaan Puri?

  So they, they, how does that work? So they knowingly had scammers.

• 28:56Speaker 01

  So that's a big issue in our industry. There's all these people doing romance scams. And so that's, you know, a hard part every day. You're always trying to, to deal with that. But so what Match did, which was actually a, a solution to the problem, a very unethical one, but they just said, well, let me send the scammers to the people who have not yet converted to membership and tell them they have a message waiting from a very good looking profile because they're a scammer.

• 29:16Shaan Puri?

  Right.

• 29:17Speaker 01

  And then, so you get hundreds of thousands of subscriptions sold through basically a sales force full of scammers.

• 29:22Shaan Puri?

  Right.

• 29:23Speaker 01

  That you're using to, I mean, it was almost like genius in its evilness.

• 29:26Shaan Puri?

  Yeah. I was going to say, that's somebody like me in the company who's like, yeah, here's the idea, guys.

• 29:30Speaker 01

  Yeah.

• 29:31Shaan Puri?

  And then of course it comes around in the end.

• 29:33Speaker 01

  Succession or something. I was like, wow, this is like an evil. I mean, I'm sure it probably wasn't, you know, that nefarious, but, but it is.

• 29:41Shaan Puri?

  That was their model.

• 29:42Speaker 01

  Our industry is known for doing a lot of like shady. Stuff like that.

• 29:45Shaan Puri?

  And you have all these different apps that have these different models. Some raised tons of money. Others like Plenty of Fish, like kind of famously.

• 29:52Speaker 01

  He's like my role model, man. He didn't take any money.

• 29:55Shaan Puri?

  Why is he your role model? What did he do?

• 29:57Speaker 01

  Well, first of all, he coded. So I coded a lot. So I mean, part of how we were able to kind of keep costs down and be able to be super lean is that I I'm like super in the weeds on the product and I I'm handling. I'm doing heavy lifting, or I was at that time. And he's the same way. Like, he really, you know, he built all the algorithms. He would go and ship code at night and he was able to basically not have to raise any funding.

• 30:18Shaan Puri?

  Bootstrapped it to like some crazy scale, right?

• 30:20Speaker 01

  Kept the team pretty small and like just, you know, did a not like a lifestyle business. It was basically almost like the benefits of a lifestyle business with the exit value of a

• 30:31Shaan Puri?

  How much did they sell for?

• 30:32Speaker 01

  Andreessen backed startup or something.

• 30:33Shaan Puri?

  They sold for hundreds of millions, right? Yeah, 800 million.

• 30:36Speaker 01

  Yeah.

• 30:36Shaan Puri?

  Jeez.

• 30:36Speaker 01

  And he owned the whole thing. Isn't that insane?

• 30:39Shaan Puri?

  That is insane. Yeah. Congrats. And also, like, if you ever used Plenty of Fish, it was kind of the worst product.

• 30:44Speaker 01

  Oh, it's crappy. But I mean, he, he, so the thing in our industry is all the people that got big all hacked an acquisition channel that was new and they used Facebook News Feed before it got regulated. They used mobile, uh, Google mobile ads before they got, anyone knew what they were doing. Marcus knew Facebook ads inside and out. And when they launched countries, he would just, from what I heard, I tried to read all these people's secrets, but what I heard is they would just basically stuff the channels where you spend so much money, no one else can compete. And then so when you're in Brazil and you type anything in dating, it's all Plenty of Fish everywhere.

• 31:13Shaan Puri?

  Right.

• 31:14Speaker 01

  And they almost like sponsor the internet.

• 31:15Shaan Puri?

  Bought the whole market, yeah.

• 31:16Speaker 01

  For the month of their launch. And so you have to have enough money to do that, of course, but he was, nobody was paying for Google mobile ads at the time, so it was cheap. So you basically are finding arbitrage opportunities, which is why it's really hard to grow when you don't have one.

• 31:29Shaan Puri?

  What did the other dating apps do? So I remember with Tinder, uh, looking into it and they have some story. I don't know how important this was, but the story was they launched on college campuses and they would send somebody, I think Whitney, in and she would go talk at a sorority or fraternity and be like, hey, everybody in the room, download this app right now. They would get the whole sorority on, walk across the street to the fraternity, have them download it and be like, hey, look, all these matches are on. And then they would throw a party that night and you have to show Tinder on your phone in order to get it. I don't know if this is exactly the model, but I've read stories like this, which is really smart, but difficult to do in a way. It's, it doesn't sound that difficult, but most entrepreneurs don't like to get out of the room and go do this. So what did you look at that you were like, oh,

• 32:13Shaan Puri?

  I can do, here's my, here's my way to grow?

• 32:16Speaker 01

  Well, I did that. I mean, I did, I did the exact same thing, but with my MBA network or my Salesforce network. But I did, you know, I did a ton of events in San Francisco because A, I feel like that's how you build your brand, you know, when you're at the beginning stages, people don't associate well with a brand. They only know online. They want to know the person behind the brand. So I just felt like it was a good way to, to build a brand. And also, the main thing we're selling is people meeting each other, which is a physical product, actually. So it's like, why not give them the product they're looking for, which is to meet people. So it's makes so much sense for a dating app to, to market with events. I think the hard part is, we've done this, it's just, you can maybe break even on events, but it just becomes, you're eventually running an event marketing arm, which is opposite of running a software company where you're like focused on.

• 33:01Speaker 01

  So, and when you're small, you have to kind of decide which one you want to do really well. So we chose to, to be more of a product and a software company. But I still think like, we're partnering with Eventbrite now to, to try to, to still be offering, to still be able to offer events without having to kind of put them on ourselves. Because that's what we found. It was like, even with an ambassador programs, there's still overhead and management, you're still having if someone represent your brand.

• 33:22Shaan Puri?

  So when you guys go to a new city, you know, you want to go open up Moscow or wherever tomorrow?

• 33:28Speaker 01

  Always do a rooftop bar. That's our, that's our rule. Yeah, we have a playbook. Just pay for whatever the coolest rooftop bar is. We don't care about the venue cost.

• 33:35Shaan Puri?

  Why people love going to a rooftop bar? I love it.

• 33:37Speaker 01

  It's better to pay up and just not worry that your venue, you picked a bad venue. So we, we believe in rooftop bars have a very high success rate.

• 33:46Shaan Puri?

  And has there any, has there been anyone who's really helped you from an advisor mentor level? Can you tell us a story about, you know, somebody or a moment where they kind of helped shift your direction?

• 33:58Speaker 01

  Oh my gosh, so many. I lean on my business school network a lot. So I mean, I feel like the league was incubated at Stanford. I was in the venture studio. It's sort of like for the people that are getting ready to go into startex, we actually didn't get into startex. But there's, you know, there's a ton of entrepreneurial programs at Stanford and actually four of my professors invested in the league as angels.

• 34:18Shaan Puri?

  Nice.

• 34:19Speaker 01

  And so I basically took advantage of that.

• 34:22Shaan Puri?

  Do a lot of professors do that? A lot of professors do angel investing?

• 34:25Speaker 01

  I think they do. A lot of them. It's a pretty cool perk of the job, right? You get first dibs on a lot of Stanford startups. But yeah, so, so one of the things I always go back and talk to them a lot is about people management stuff, just because that's something I, I didn't come into doing a lot of that. When I started the league, that wasn't my background. And there's always these situations that you would never dream up. Like you just couldn't make some of this stuff up where you're, you know, you're dealing with human psychology and trying to understand how do you keep someone motivated, but need to hire above someone? And how do you deal with, it talks about equity and things where people feel, you know, you're almost like mediating really tough situations. And so I actually

• 35:06Speaker 01

  had one of my professors mediated between me and my first hire about the one who, who I'd contracted with about our equity split and actually helped us like come to a good agreement on that. Yeah.

• 35:18Shaan Puri?

  And for you, how many people are at the league now? How many people are on the team?

• 35:23Speaker 01

  So we're about 30.

• 35:24Shaan Puri?

  30. Okay, great. And do you like managing?

• 35:26Speaker 01

  I like building first. And then I like, and I like managing this, how do I say this? I don't like managing for the sake of managing. Like I like managing when it...

• 35:38Shaan Puri?

  To get stuff done.

• 35:39Speaker 01

  Yeah, when I'm seeing something done. So I love product management, for instance, because you're, you know, you're managing sort of, you're, you're building this thing and you're managing the team that is, is creating it. I think just sort of day to day, people management isn't my strength. Like I don't love, you know, doing performance reviews, or I don't love thinking about work charts, or compensation plans, or things like that. And so I think I prefer smaller teams because there's a lot of less... Less

• 36:05Shaan Puri?

  Less of that stuff.

• 36:05Speaker 01

  Overhead, yeah.

• 36:07Shaan Puri?

  Yeah, me and Sam talk about this all the time. It's like now that we've gotten a couple of exposures to, you know, different businesses and how they grew and some are small. Now we got acquired, so I'm at Twitch where there's like 2,000 people.

• 36:18Speaker 01

  Yeah.

• 36:19Shaan Puri?

  And so when I

• 36:19Speaker 01

  I want to hear about that experience.

• 36:20Shaan Puri?

  When I work with Emmett and he's a CEO of this big company and it's, you know, owned by Amazon, all this stuff. And I see his day to day and I literally had the thought, I was like, wow, I would never want to do this. And it's not that he's unhappy, he, you know, he enjoys it, but I realized through seeing it, I'm like, this is not what I want. I used to think that. I used to think, man, I want to build this big, huge company.

• 36:41Speaker 01

  I used to think I wanted to be Sheryl Sandberg.

• 36:43Shaan Puri?

  Yeah. And now I'm like, no, like

• 36:45Speaker 01

  And now I look at her job and I'm like, first of all, I'm not even good at any of those things now that I know.

• 36:49Shaan Puri?

  My trick, I need to figure out a way to get demoted, so I'm managing nobody.

• 36:53Speaker 01

  Yeah.

• 36:53Shaan Puri?

  But get paid more.

• 36:54Speaker 01

  A creative director, I decided that's what I want my title to be.

• 36:57Shaan Puri?

  Right. Yeah. Like special projects. Nobody knows what the hell I'm doing.

• 36:59Speaker 01

  Yeah. Google X.

• 37:01Shaan Puri?

  Yeah. You said, you said you wanted to ask about that. What did you want to ask about?

• 37:04Speaker 01

  Oh, just how, how that experience was going.

• 37:07Shaan Puri?

  Going from small, small company to big or what?

• 37:09Speaker 01

  Yeah. I guess, well, I guess just the journey or the after, aftershock, maybe how it feel, how it felt then, how it feels now and

• 37:17Shaan Puri?

  So when it happened, I had a whole bunch of assumptions.

• 37:20Speaker 01

  Joy, grief, like, I don't know.

• 37:22Shaan Puri?

  Relief. First relief because like I gave a talk at HustleCon called How to Sell a Failing Company, because we weren't taking off like a rocket ship when we sold. It wasn't Instagram getting bought by Facebook, right? We were like, hey, you built something interesting. You have an interesting user, user base, but this isn't like super profitable. It's not in hyper growth mode. And I, you know, I

• 37:43Speaker 01

  You have to choose one of those, right?

• 37:45Shaan Puri?

  Yeah.

• 37:45Speaker 01

  You need to be super profitable or

• 37:47Shaan Puri?

  And I told my investor, I was like, look, I think we have something, but the road to get where we want to go is long, A, and B, we also have way more information now that tells us this is not going to be one of those mega companies. You know, the reason we got together and decided to do this, I don't believe that outcome's going to happen. So my opinion is we should try to sell this thing. And he was like, okay, you know, if you want to do this. Yeah, I also needed a change. I've been doing it for like five, six years at the time of a couple of different pivots and

• 38:14Speaker 01

  But then none of the investors brought it up to you. You brought it up.

• 38:16Shaan Puri?

  I brought it up.

• 38:17Speaker 01

  Wow.

• 38:17Shaan Puri?

  And so he was like, I think his preference would have been to keep going, but you know, he was super understanding and was like, look, that that makes sense. So I said, here's what we're gonna do. Let's take the next 30, 60 days and let's see if we can get an offer. And so I went and started, I basically took the meetings that, you know, some people had been interested.

• 38:34Speaker 01

  Right.

• 38:35Shaan Puri?

  Other people had never even heard of us and I started knocking on those doors and taking, replying to the people who already showed interest. So by the time we got ready to do it, it was just a relief that the deal closed, right? Cause there's so much that goes into it. And that's what my talk at HustleCon was for is like, nobody teaches you how to do this. And now that I went through it, I'm like, oh, I should write this down because there's nothing on the internet about how to sell a company that's not in.

• 38:57Speaker 01

  Totally.

• 38:58Shaan Puri?

  You know, there's a lot of things about how to sell when you're big and successful.

• 39:01Speaker 01

  Right.

• 39:02Shaan Puri?

  And the answer there is pretty much just like hire a banker.

• 39:04Speaker 01

  Yeah.

• 39:05Shaan Puri?

  Yeah. Hire a banker and pick, you know, your offer. So anyhow, by the time it was done, it was relief.

• 39:11Speaker 01

  How long did it take?

• 39:12Shaan Puri?

  We went really fast. So we got our term sheet in 45 days after we decided to start the process. And.

• 39:18Speaker 01

  Your first term sheet, did you get more than one?

• 39:20Shaan Puri?

  Yeah, we got, we got two and then by the time the third, we were gonna get a third one, but we told them, like, they weren't close. So we were just like.

• 39:27Speaker 01

  Close.

• 39:27Shaan Puri?

  Yeah, they weren't gonna be close. And then, then we ended up closing 45 days after that. So the whole thing took 90 days, three months total. And from like.

• 39:34Speaker 01

  You're a closer.

• 39:35Shaan Puri?

  That conversation.

• 39:36Speaker 01

  That's awesome.

• 39:36Shaan Puri?

  Well, that's what I told my team.

• 39:37Speaker 01

  I can even fundraise like a million dollar seed that fast.

• 39:41Shaan Puri?

  Well, I told my team, I was like, unfortunately, the best thing I did as your leader was this last 90 days. I wish I had, I had run the company as well as I sold the company.

• 39:50Speaker 01

  Yeah, that's great.

• 39:51Shaan Puri?

  Um, but you know, whatever.

• 39:52Speaker 01

  But they say that's how you're supposed to do it, run a really tight process and time is the enemy of all deals.

• 39:57Shaan Puri?

  Right. And I, I had these people that I, I called my, my deal doulas. And so like, my wife just had a baby and that's when I learned what a doula does. And for the deal, I had these five deal doulas. And one of them, he told me, you know, he, when I showed him the term sheet, I told him, hey, we got the term sheet. And we're gonna sign this one. I thought that was the end of the process. And he's like, oh.

• 40:18Speaker 01

  Now you need to do all this.

• 40:19Shaan Puri?

  Now you need to sprint the hardest. And I was like, what? Cause I had mentally started to ease. Up.

• 40:24Speaker 01

  Yeah.

• 40:25Shaan Puri?

  He's like, no, no, no, no. Like you need to like now you need to sprint to the finish through the finish line because this is not the finish line. This just tells you there is a finish line and.

• 40:36Speaker 01

  Data requests.

• 40:36Shaan Puri?

  Yeah, we had to do our data room, get through due diligence, make sure that like nobody like the deal doesn't fall through, the the met execs on their side stay happy. My team stays together and doesn't start like, you know, getting itchy and.

• 40:48Speaker 01

  You told your team?

• 40:49Shaan Puri?

  I told my team, which was unpopular. I told him from day one, I said, look, I can't come in and look you in the face and say, hey, go work your ass off on this feature when I know we're not going forward with that feature. So I told him, I said.

• 41:02Speaker 01

  After you had it signed, I assume.

• 41:03Shaan Puri?

  Before.

• 41:03Speaker 01

  Oh, yeah.

• 41:04Shaan Puri?

  Which was, that's the part that was like unconventional. I said, I'm gonna run a process next, next thirty days. And I'm gonna know what type of appetite there is. You've been working hard for like four years straight, like really, really hard. I need you to relax. I need you to trust me and I need you to not talk to anybody. I will give you, I will tell you what's going on. And I'll tell you if it's gonna happen, I'll tell if it's not gonna happen and we'll wait, we'll figure out a way forward either way. But I need you to just chill and let me do my thing. And I said, if anybody wants to learn about how this process works to sell this thing, I'm gonna have to figure it out myself. There's an opportunity if you want to learn something. Nobody, nobody took me up on it.

• 41:39Speaker 01

  That's what I always say startups are like an MBA, much cheaper.

• 41:43Shaan Puri?

  I was like, I was like, where are these guys? Don't they want to know? Like, it was the most fascinating process to me to figure this out. But nobody took me up on it. I don't know. I'll never understand why. But yeah, it was just relief. And then when I got there, I felt rejuvenated, like, I was like, oh, here's a whole new situation. Bunch of new people, new shit to learn. You know, let's see what this is like. I've never worked at a huge tech company. Okay, let's go, let's go try that experience. So I'm still there right now. And so let's go try this out and let's see if this is great or if this is horrible. We'll find out.

• 42:13Speaker 01

  That's exciting, though.

• 42:14Shaan Puri?

  And so, you know, that's.

• 42:16Speaker 01

  Corporate life.

• 42:17Shaan Puri?

  Yeah, I got, you know, I get to do my podcast.

• 42:21Speaker 01

  That's the, that's the dream is if we get to a bigger, you know, you get the company bigger than you can have a little more time. You always think, but then it's like,

• 42:29Shaan Puri?

  Yeah, I don't think that ever happens.

• 42:31Speaker 01

  The time doesn't come.

• 42:33Shaan Puri?

  I found it only happened when the company had sold. And then actually I started this during due diligence because there's nothing for me to do at that point. I was just kept asking the lawyers, what's going on? And they're like, hey, we're waiting for, you know, Amazon's lawyers to get back to us. Nothing we could do.

• 42:46Speaker 01

  Yeah.

• 42:47Shaan Puri?

  And so I was like, okay, I started getting itchy and I was like, well, I can't start like a new business. That would be stupid. That would jeopardize the deal. I'll start a podcast. I've always wanted to do that. Let's see what happens. And then now fast forward like six months since then, and I think we're at about a million downloads in six months, which is like crazy. And so I didn't expect that, basically.

• 43:07Speaker 01

  So it happens. You put a founder on a podcast, man.

• 43:10Shaan Puri?

  Well, the, the fun thing is you probably feel this too, which is you meet people and you hear these stories. You hear their story. I hear, you know, if we had just met normally, that's be over dinner or drinks or whatever. And you hear it and you're like, holy shit, this is why people move to Silicon Valley is to be surrounded by these people. But I remember what it was like to not be in Silicon Valley. I was in Australia before I moved here, literally the other side of the earth. And so I remember wanting to be a fly on the wall for those conversations. And so that was the impetus is like, what if I just, let's start with this 10 people who I've already heard their stories and they're amazing. But this time I'll push record and now other people can listen to it and like, let's see, let's take it from there and see what happens.

• 43:45Speaker 01

  Yeah. No, I've always wanted to eavesdrop on conversations, which is why I think podcasts are so cool. Cause it feels like you're, it's what you're doing.

• 43:52Shaan Puri?

  Now you're the founder of a, of a tech company, you know,

• 43:55Speaker 01

  Thank you for calling it a tech company and not a dating app.

• 43:57Shaan Puri?

  Tech companies love, well, I was actually going to make a joke that tech companies love to spy on their, their eavesdrop on their users, but.

• 44:03Speaker 01

  Oh, I know. No, we're, hey, so we're one of the few independents left, so we're, we're trying to, you know, combine forces so that we can be the beacons of, of hope for the. Tech community.

• 44:14Shaan Puri?

  What goes through your mind when Facebook's like, oh yeah, we're doing dating now? Is it, what happens in the company that day you hear that news? Is it, does it even, is it even a blip on the radar? Do you address it? Do you think about it?

• 44:24Speaker 01

  Of course. I mean, it's, it's like one of the scariest things that can happen to any industry. Yeah, it was, it was crazy. We, it came right after they had started really cutting down the API access too. So about six months before they released Facebook Dating, they basically stopped letting anyone look at profession and education and your hometown and your age and your mutual friends, which most of us had built our whole apps around. Tinder had built around it. Bumble had built around it. Hinge, we've all did mutual friends. We all, so they basically just cut off that, that data source. And we luckily use LinkedIn as our primary data source. And Facebook is more of a like, nice to have. So we were actually one of the few that were left sort of okay.

• 45:08Speaker 01

  I mean, we're still bleeding, but the other people were totally cut, cut off. And they now have no social graph, which was part of why these apps even made it because they were, they synced with your identity and they, Facebook is better at scam detection than matches.

• 45:22Shaan Puri?

  Right.

• 45:23Speaker 01

  So people forget that, like Facebook gave us a lot of.

• 45:26Shaan Puri?

  They did a lot of work.

• 45:27Speaker 01

  And a lot of data. And then now they're taking it away. And so it's, yeah, it's almost like we're going backwards, back into the Wild West of like, and everyone's anonymous now on the internet. And so now the, the problems that, with an anonymous internet are happening worse.

• 45:40Shaan Puri?

  Right.

• 45:40Speaker 01

  So, yeah, I guess a long, long way, long-winded way to say that I, I don't think they're putting a lot of money or horsepower behind it, but, and I actually think it's good for demographics that live in rural areas and are not high density, because it's the biggest database wins in dating in general. But I don't see them as a big competitor in like, you know, New York City, like elite or professional dating or anything like that.

• 46:03Shaan Puri?

  You just don't want LinkedIn Dating to come out.

• 46:05Speaker 01

  No, I, you know, I pitched LinkedIn on letting me run their LinkedIn Dating when I interviewed there.

• 46:09Shaan Puri?

  Before or after?

• 46:10Speaker 01

  It was before. I interviewed at business school and I said, all we need to do is add one button, single or not single.

• 46:15Shaan Puri?

  Heart, yeah.

• 46:15Speaker 01

  And we got a dating app on our hands and let me run this. And I was like, you know, brash MBA that was asking to run my own division and they didn't give me an offer.

• 46:25Shaan Puri?

  They're like, not only are we not going to do this, we don't like your can do attitude. You stay out of here.

• 46:30Speaker 01

  It's a little too ambitious. So then that's why our tagline is an app for the overly ambitious. Cause I was like, I'm just going to do it myself. You have an API.

• 46:36Shaan Puri?

  Right. I like it.

• 46:38Speaker 01

  But yeah, LinkedIn, it now, but they got bought by Microsoft. I mean, the world changed in the five years I've been doing this. It was like a totally different place in 2014 than it is now. And now it's, it's kind of unclear what's, what's going to happen with all the privacy regulations and cookies are going away.

• 46:53Shaan Puri?

  Right. Yeah. The data, data stuff is interesting. So one of the questions I like to ask everybody who comes in is knowing what you know about your space now, two questions. So the first one is knowing what you know about your space. Oftentimes when you're operating a business, you see adjacent opportunities. It's like, we're trying to build this thing and man, it was so hard for us to take payments in India. There should be a payments Stripe for India. That should exist. Have you noticed any sort of like adjacent opportunities as you've been building your business? Either something that would help your company run better or help dating apps grow or, you know, like, is there anything you've observed that you guys aren't going to go do? But you, you've seen, you've noticed?

• 47:31Speaker 01

  Yeah, it's a good, it's a good question.

• 47:32Shaan Puri?

  It's a tough question. I know.

• 47:33Speaker 01

  Yeah. But I mean, we are on the ground floor, like building tools and we're, you know, we were one of the first, the first adopters of branch metrics. They actually were classmates of mine, but you know, around mobile attribution. So we're definitely kind of deep in the ad, ad tech space and seeing all the changes happen. I guess for me though, it's less about what we've wanted to always build is sort of this global blacklist. I guess you could think of it where there's always bad actors and all of us are the non-Facebook and the non-Google people. We like, don't have huge databases and machine learning teams and giant infrastructure to prevent like thieves from getting on the apps and stuff like that. And we're all literally solving the same problems.

• 48:16Speaker 01

  Every dating app founder and every social messaging app I talked, we're all solving the same problems.

• 48:21Shaan Puri?

  Repeatedly.

• 48:21Speaker 01

  Tons of different ways, different approaches. No one's learning from each other. So it's like a way to, to actually sort of solve off an identity without necessarily having to work with Google and Apple. And obviously you have to work with the hardware, but, but can. Can we, can we at least say, well, we checked with all of the other independent people and we all know that this person is a sexual predator. So we are all gonna not let him

• 48:43Shaan Puri?

  Right.

• 48:43Speaker 01

  be on Coffee Meats Bagel, or Hinge, or The League, or Bumble. And like, like, how do we like use, put the user safety first?

• 48:49Shaan Puri?

  Right.

• 48:50Speaker 01

  And, and I think no business models are really incentivized to do that, to share that data. And, cause it doesn't, so if there's a way to, I almost call it like the WW3C of like, online safety and trust and safety and data privacy and creating sort of a, I don't know, an alliance.

• 49:07Shaan Puri?

  Totally. You know, we, I had heard, so a couple of stories related to this. I had heard that back in the day when Facebook was growing like crazy, like kind of earlier tech. I talked to some of the guys who did like security ops, or like the scaling issues. And they were all trying to solve the same things, like, oh my God, we're growing like crazy, how do we scale? No companies ever scaled this much before, or security issues, they're getting DDoS'd and threats like that. And these guys would have this underground brunch, they didn't even tell the employer. It's just like, the guy who's stressing out about this at every company, and they would do this brunch. And at that brunch, they would be like, here's how we're trying to attack it, just share information. That was one. The second is, there's a company called Sif Science, you heard of them?

• 49:45Speaker 01

  Yeah.

• 49:46Shaan Puri?

  And so they, they were basically a Facebook fraud team, I think, or the Facebook sort of like, um, trust and safety team. That spun out and then tried to say, hey, we're gonna build

• 49:54Speaker 01

  Right, we looked at them.

• 49:55Shaan Puri?

  Facebook level tools and make it available. We used them and we had a lot of success when we had a, we built an app that was growing, it got to like four million users. But Martin Shkreli was one of them, do you know who this guy is?

• 50:07Speaker 01

  Mm-mm.

• 50:08Shaan Puri?

  If you Google most hated man in America, he comes up, uh, he's now in jail, just to give you a sense. He was the guy, you probably heard about it, he bought this like drug and then jacked up the price. It was like a drug for like, you know, a pretty niche disease. And it was the only drug on the market for it, and then he like 40x the price. And so people were just like, this guy's an asshole. And so, and he used to do all kinds of trolly type of stuff, uh, like, he bought the Wu-Tang, Wu-Tang came out with their one last album or whatever. And he bought it for $2 million and then just like stashed it and like didn't let, you know, like, he would just do things that would piss off different communities. And, uh, so he was on our network and 4chan was like, uh, F this guy, they didn't like him. Or these different little hacking groups on the internet. And so they started attacking us because he was on our platform.

• 50:51Shaan Puri?

  And so we had to deal with all this crap because of, uh, because of him, essentially. And so, you know, we eventually use safe science and it ended up helping us, but

• 50:59Speaker 01

  There's a lot of those ones, but it's like they're not, they're all kind of, they're giving you the tools, but there's not like a shared database of like

• 51:05Shaan Puri?

  Well, they're trying to keep the database for themselves.

• 51:08Speaker 01

  Right, everybody wants their own database.

• 51:09Shaan Puri?

  For all their customers.

• 51:10Speaker 01

  They want us to give them our data and I'm like, but wait, we're going to be all of our users that we spend all this time acquiring and you're going to just tell us if they're bad or not? And I'm like, no, I want it to be part of that. Like, I want it to be like quid pro quo.

• 51:23Shaan Puri?

  Right.

• 51:23Speaker 01

  Like, the people who own the data should be talking to each other, not all these brokers trying to sell. I mean, that's why the data, that's why the space is all effed up anyway, because we have tons of brokers in the middle selling people's data and no one's pointing to them. Everyone's pointing to Facebook and Google.

• 51:37Shaan Puri?

  Right.

• 51:37Speaker 01

  And it's really the, the middle people that are kind of the real nefarious ones.

• 51:41Shaan Puri?

  Gotcha.

• 51:42Speaker 01

  I think. I mean,

• 51:43Shaan Puri?

  I like that. That's actually a really good answer and opportunity. At Twitch, we talk trust and safety is like one of the main focuses. And it's just like, we're just trying to solve the problem from scratch. And you're right, it's a, there should be a little more collaboration. So, another question I ask is, let's say you're 21 years old, let's rewind, you're 21 years old again. You can't do what you're currently doing, so you can't go into this space again. What space would be interesting to you? Where would you go if you were going to start a new business?

• 52:09Shaan Puri?

  You know, from scratch and you, and you had, you had the time, but you can't go into your existing space?

• 52:12Speaker 01

  Cannabis 100%.

• 52:15Shaan Puri?

  Okay, what would you do?

• 52:15Speaker 01

  I actually looked into going into it at business school too, because the laws were starting to change. It just, I figured that software with like no regulations would be easier than a bunch of heavily regulated industries where it may or may not be legal, but I just think that there's a huge opportunity to really redefine the experience of, like, everything from what's happening with the kids aren't drinking anymore, to the White Claw movement, to the fact that people are doing jewel pens, to the fact that people have edibles now. I just think that we're sort of reinventing what socializing looks like and we're at the, we're at the point where you can kind of design how you want it to be. The entrepreneurs get to design this next world.

• 52:56Shaan Puri?

  What would that look like for you?

• 52:57Speaker 01

  Well, obviously, you can, obviously nightclubs with drinking and smoking. And I'm surprised that hasn't really happened yet.

• 53:04Shaan Puri?

  Yeah, strange.

• 53:04Speaker 01

  Or as fast as it, it would have in Denver or something like that. But I, so I, I mean, I'm thinking of it kind of from a, You know, of course, an owner of a dating app thinking about the events you would have. But, you know, I think, I just think that, A, from a socializing perspective, that's one sort of way to brand it. And then also, there's, you know, is it really good for you? And maybe the microdosing industry and the microdosing movement is something that is sort of burgeoning too. So there's so many different flavors of approaching what's happening with the fact that a huge regulation has just been changed. And you could have like 100 different flavors of startups to serve each niche, from your morning coffee, you know, the new next Starbucks brand of cannabis. And I think a lot of people are

• 53:47Speaker 01

  trying to do it. So that's, you know, I'm sort of watching from afar, but I'm very much intrigued. And I like, I like building brands. So I just think it'd be fun to build like a very, I don't know, cool, cool league-like brand for cannabis.

• 54:01Shaan Puri?

  Look, I mean, the look on your face, it seems like you're gonna do this. This is fantastic.

• 54:05Speaker 01

  Well, it's like the gold rush. And it's like, there's not that many laws that have changed while I've been around and able to be like an entrepreneur to go after these advantages. And that's what, I remember when I worked in Sequoia, that was like their number one rule was like, when things change in the industry, when, you know, consumer behavior shifts, or like huge regulation shift, or technology changes, turn a corner, that's when, that's when you all need to start running. And that's, you know, that's why the gold rush is called the gold rush. But, you know, I think, so I think that's exciting. And that's like the only one I see. You know, self-driving cars is cool, but I just don't see the regulations able to support that anytime soon.

• 54:37Shaan Puri?

  Gotcha. That's cool.

• 54:39Speaker 01

  I'm more into like near-term, near-term things.

• 54:42Shaan Puri?

  And is there anything else you want to share for the people who are listening? You know, stuff that you're interested in, or new stuff that you guys are doing? This is your chance to sort of shout that out. Also, where do people find you? How do they connect with you? Are you gonna, you want Twitter followers? You can get Twitter famous off this.

• 54:56Speaker 01

  No, I like being sort of discreet on Twitter a little bit, a wallflower.

• 55:00Shaan Puri?

  Right.

• 55:01Speaker 01

  No, this is my part, this is the part where I get to do self-promotion. Oh, great. So I'm more of a, I guess I'm Twitter and Instagram. I don't know. I'm just Amanda Bradford, boring. And then, one of the models for this League Live, I know I've been talking about it a lot, but the video chat, the chat roulette sort of feature that we have, I think there's a lot of really interesting applications, because essentially, we're We're essentially setting up an appointment, right? You're getting three appointments every day at 9:00 PM. And so, obviously, the use case we're solving first and foremost is, let me help you find a person to date, and then, great. And then, but, once you've solved that, there's a lot of other things you need to search for, that you need to set appointments for. Like, for instance, let's say you wanted to find a realtor to buy a house. Let's say you wanted to interview a nanny to take care of your kid.

• 55:45Speaker 01

  Let's say you wanted to talk to a therapist and interview three. So, I think, you know, and then Jeremy and I, actually, we're going to, they recommend, before you get married, you go to a couple, a couple of premarital counseling sessions. So, we've been doing that, which has been really interesting. And my wheels have been spinning, being like, well, we can use this same-

• 56:04Shaan Puri?

  So, what do they do there? I didn't do this.

• 56:05Speaker 01

  Oh, you didn't do this?

• 56:06Shaan Puri?

  I didn't do this, no. What did I miss?

• 56:07Speaker 01

  Well, first, you both talk about your past and your background and your family, and just kind of get to know each other's history. And, you know, you should have probably done that by now, but it's-

• 56:16Shaan Puri?

  I was gonna say, is that-

• 56:17Speaker 01

  It's nice to just sort of, the way they, they'll lead the questions, and you'll talk about the personalities of your family, in like, a very dispassioned way. So, it's just an interesting kind of experience to hear them, hear everybody be sort of described from, from their perspective. So, you do that, and then, and then you go through kind of how, you know, any, any conflicts that you've had, you sort of, you analyze them, and you put them under a microscope, and you talk about what, you know, why that made you mad, and why you didn't expect that to make me mad, but it did, and why, oh, that's because you really value people showing up at the same time, at the right time.

• 56:53Shaan Puri?

  Right.

• 56:53Speaker 01

  And maybe I don't value being on time that much. And so, you start to get into like, your value system. So, it's, it's actually quite interesting, and it-

• 57:00Shaan Puri?

  So, you'd recommend it?

• 57:02Speaker 01

  I think it's, I, I think it's crazy to think that you might, like, create a family without start, without kind of understanding where your differences are, and if they're, you know, and just sort of respecting each other's. And it doesn't mean you have to change, but just sort of knowing.

• 57:16Shaan Puri?

  Right.

• 57:16Speaker 01

  I like knowing, I guess, before. For that, so I kind of like to think of it as kind of like reading each other's, you know, little novel and it's this kind of fun, shared experience. So yeah, you go to a couple and they say it's supposed to be better. Then my parents and their last one, they wrote a letter to themselves to read at their 20th anniversary.

• 57:33Shaan Puri?

  Wow.

• 57:34Speaker 01

  So it's kind of cool.

• 57:35Shaan Puri?

  And would you continue this?

• 57:36Speaker 01

  But that was saying that could be something when we were going out, I was like, we should totally, this could be the next step on the league is once you've met each other and you're dating, then you could go and meet, if you had to do couples counseling or talk to a therapist or find a minister to marry you, whatever it is.

• 57:51Shaan Puri?

  Yeah, I sort of feel like.

• 57:52Speaker 01

  So that's what goes in line with the therapy movement right now.

• 57:55Shaan Puri?

  Yeah, I was gonna say.

• 57:55Speaker 01

  All the rage.

• 57:56Shaan Puri?

  Somebody tweeted this out, they said, it was kind of a stupid tweet, honestly, but it was like, you know, five years ago, the trend was X, I don't remember what they said, 2020, you know, 2020 was, you know, about meditation. What's 2025? And my answer was therapy.

• 58:10Speaker 01

  Yeah.

• 58:10Shaan Puri?

  Because, and I don't even go to therapy.

• 58:12Speaker 01

  I think I saw that, that was Brian Norgood, right?

• 58:15Shaan Puri?

  That's right, Brian, yeah, Brian said that out.

• 58:16Speaker 01

  Yeah, he's awesome.

• 58:17Shaan Puri?

  And so I think that's gonna happen and.

• 58:21Speaker 01

  I think I, I think I retweeted that.

• 58:23Shaan Puri?

  There we go.

• 58:24Speaker 01

  You're one of my retweets.

• 58:25Shaan Puri?

  Fantastic.

• 58:26Speaker 01

  I believe it.

• 58:27Shaan Puri?

  And I think that I've noticed for all the areas that matter in your life, fitness, your career, your relationship, it's only like five things that matter, right? Your parenting side of life, there's a handful of things and having A, an outlet or B, a coach or trainer of some kind or counselor of some kind, I've never seen it hurt. And but they're all, you know, they're sort of getting de-stigmatized. Each one's getting de-stigmatized where, you know, before, if you were doing something, it's like, oh.

• 58:53Speaker 01

  Means it's not working.

• 58:54Shaan Puri?

  Is it not working? Is it broken? It's sort of this admission of failure, which is kind of silly when it really should just be saying, this matters to me and I want to make it better. Yeah. You know, I don't go to the gym because I'm injured. I go to the gym because I'm trying to make something more fit, more strong, whatever. And that's what it could be for relationships, what it could be for your career.

• 59:10Speaker 01

  It shouldn't even be called therapy. It's like relationship coaching, which implies that it's something you do just to keep it in good health and good fitness. Yeah, I like that.

• 59:18Shaan Puri?

  So I think that's gonna continue to become less stigmatized. My friends are the guys who started Calm and I remember.

• 59:24Speaker 01

  Oh, yeah.

• 59:24Shaan Puri?

  Early on, it was just like.

• 59:26Speaker 01

  Crushing it, yeah.

• 59:27Shaan Puri?

  But early was not, and it was just like, yeah, this thing, I believe in this. I've been doing this for a long time, but it was fringe. And even when it started to take off.

• 59:36Speaker 01

  What happened? What made it change?

• 59:37Shaan Puri?

  So I was asking him, I was like, look, I remember when you guys were doing, you know, like a hundred thousand in revenue annually, and you couldn't raise money, and it was tough. And like, then all of a sudden, it was like, yeah, we did six million last year, 20 million this year, 80 million, and it went like, and now they're in a hundred million plus a year revenue. And I asked him, what changed? What was the tipping point? And I thought it would be a product feature. I thought it'd be some tweak they made. Obviously, they did improve it over time, but he's like, honestly, the wind just started blowing behind our back, right? Like, people started to care about this. People started to care about their mental health. People felt really anxious. They were looking for a solution. And all of a sudden, you know, Apple featured them as app of the year because it was one of the few apps that A,

• 1:00:19Shaan Puri?

  made money, which Apple likes, and B, was not like social media where there was all this like sort of toxicity behind it. This was like pure good. So Apple featured this app of the year. That was big. They got on like Dr. Oz or something like that. But basically, people started to care about meditation, just started to search for it. And they were already there. They had done four years of work to be like sitting there with a good product, ready to go.

• 1:00:40Speaker 01

  Ready for when everyone, well, that's what we're saying for this League Live feature, because not everyone's ready for video dating yet. We're like, we're just gonna at least be there, be poised. I bought up all this speed dating domains. So it's like, when people are ready to really do video dating, we're there. Because I just think we're early.

• 1:00:54Shaan Puri?

  Right, yeah, that's cool.

• 1:00:55Speaker 01

  And it's hard when you don't have the wind, right?

• 1:00:58Shaan Puri?

  Well, good luck. Good luck to you. Good luck to the League. I'm a fan of the concept. I had known about it, but I didn't know the story until you came in today. So I appreciate you sharing that. And yeah, everybody should follow you and reach out to you. But thank you so much for coming.

• 1:01:12Speaker 01

  Cool. Thanks for inviting me.