The Exchanges

Q not love an event first, but second is, kind of, once you've kind of established that, you said there about kind of ensuring medium success, if you do that, at the very least. I'm always a big believer in kind of setting benchmarks for what success looks like, So when launching products, how do you determine whether a launch has been successful? What does that framework look like for you?

A Yeah, for us, it was about, because we have this selective process, and we actually only admit in certain cities, it's 20%, in other cities, it's around 30%, but we're really accepting only a portion of our user base, and so for us, our success metric is similar to a college, kind of, it's yield, right? So it's, okay, we accepted 300 people in Minneapolis, how many actually Logged in on opening day. To me, that, that means, did we build enough buzz that this is a cool thing in Minneapolis? If everybody that, that got in, went and checked it out, that's a success. If nobody did, it's not, and somewhere in between. And so on, you know, on our first launch in San Francisco, 419 out of the 500 people we selected showed up, and that was well above kind of the 70% yield we wanted to get. So that was something we looked at. We looked at how many people messaged, how many people actually stayed to day seven, so actually came back at happy hour and kind of did the Full value proposition of the product, and then we looked at how many people invited friends. So, 50% of the users actually invited friends after they used the app, and that was a huge number when you're really small. Half your user base is helping you grow, is half your user base is being your salespeople. So, to me, those are the kind of metrics you want to be looking at, and that tells you if you have a product that people …

AI assessment note: “our success metric is similar to a college, kind of, it's yield”

Q invite makes you treat them so much more carefully, one. But I'm intrigued. You said there about the seven-day retention. In terms of retention, how do you think about that? It's obviously a problem that plagues the space more generally being consumer and also kind of romance and dating apps. Is the seven day the core metric for you? And how do you think about that maybe more longer term?

A It's not a core metric for us. I mean, for launches, it is, um, just because we, we look at it as a very focused event, but no, retention is an interesting one. You know, we, we have what we call good churn and bad churn. Good churn is when a user says, Hey, I need a timeout and they pay a dollar. That's a, we actually say, if you pay a dollar, we won't You know, your, your account's fine. You don't need to check in every day. You can kind of chill out. And so to me, if someone's willing to pay a dollar to kind of stay in the community, that's something we look at. That means they're, yes, they're, they're leaving the app, which, you know, is unfortunate, but that means it's probably for a good reason. What's not good churn is if someone's on the app and they haven't gotten messages, they haven't had matches, and you can kind of see from the data that they're falling out because they had a bad experience because no one messaged them. Um, and that's what we call bad churn. And that's, you know, that's what we're trying to focus our efforts on is What can we do in the algorithm to prevent that? Is it that we're matching them with people that have too many matches? Are we putting them in a different group? So it's really about kind of looking and making sure we're giving our users what we want is a match by the seventh day. So we're trying to figure out how our users can be shown …

AI assessment note: “It's not a core metric for us. I mean, for launches, it is”

Q mentioned that the kind of the paying of the dollar, so to speak, to kind of have a bit of a rest I'm intrigued. One interesting element that a lot of consumer founders talk to me about is when to monetize and the willingness to make users pay. How do you think about that monetization aspect early on in the journey, and how did you approach it, do you think?

A Yeah, monetization is interesting. I think the, the kind of classic playbook, at least when we were launching was in 2014, was don't worry about monetization. It reduces your focus on the core value proposition of the product, which, which I a hundred percent agree. So we, we did launch without About monetization. But what I did put in was a test for monetization. So I said, I'm not going to focus on revenue. I'm not going to focus on building a billing system. The developer I had didn't even have the capability to build a billing system. So we actually couldn't have monetized even if we wanted to. But, but what I did is I created an HTML fake page where I said, Hey, you want to upgrade for 15 dollars? If so, click this button. And then we just said, great, you're upgraded. And we, we gave them the advanced features without charging their card. And so that gave me a conversion rate That I used for that year and a half, kind of while we were on free product to give me, I guess, peace of mind that, okay, worst case scenario, we're going to have X percent of our users pay us 15 dollars. So here's sort of what I could expense and here's sort of what my budget could be. And I think that, I think doing things like that is a way to, to de-risk the strategy of, okay, we're not going to focus on monetization, but how do we de-risk the fact that it could totally fail? So having that conv…

AI assessment note: “we did launch without About monetization. But what I did put in was a test”

Q and we had Leah from TaskRabbit and Fuel Capital on the show the other day, and she suggested that with marketplaces, which in some case, you know, the league is, to a certain extent, that one side's always going to be unhappy to an extent. I'm intrigued. Would you agree with this, Kind of having seen the observations with the league, and how do you think about finding that equilibrium?

A Yeah, with dating, it's interesting, because you, you can kind of, there's a lot of different marketplace dynamics in play. There's obviously the kind of gender one, which is, you know, the majority of our user base is men and women seeking each other, so you have that, and then I think for us, um, because we have a wait list, and because we're a curated community, we can actually choose what ratio to keep the league, so we could make it way more female, less male, or we could make it way more male, less female, and you'll notice You know, I don't know if you, what other dating apps we use, but most of them don't curate their community. So it's just about who decided to log in that day. And usually on average dating apps are about like 70% active users are men, 30% women. So usually women are very outnumbered. They get a lot of attention. You know, it's pretty easy to be a woman on a dating app on most of them. And I would say on the league, it's actually quite hard in the sense that we keep the ratio of 50 50. So, you know, the women feel like they're kind of doing less well. They say, I'm not doing as well on the league because I'm on these other apps. And it's, you know, we're like, it's not you. It's literally just we're keeping the ratio balanced. And we're doing this as a service to both, you know, women and men, but it does change kind of the experience that people are u…

AI assessment note: “we keep the ratio of 50 50. So, you know, the women feel like”

Q not love an event first, but second is, kind of, once you've kind of established that, you said there about kind of ensuring medium success, if you do that, at the very least. I'm always a big believer in kind of setting benchmarks for what success looks like, So when launching products, how do you determine whether a launch has been successful? What does that framework look like for you?

A Yeah, for us, it was about, because we have this selective process, and we actually only admit in certain cities, it's 20%, in other cities, it's around 30%, but we're really accepting only a portion of our user base, and so for us, our success metric is similar to a college, kind of, it's yield, right? So it's, okay, we accepted 300 people in Minneapolis, how many actually Logged in on opening day. To me, that, that means, did we build enough buzz that this is a cool thing in Minneapolis? If everybody that, that got in, went and checked it out, that's a success. If nobody did, it's not, and somewhere in between. And so on, you know, on our first launch in San Francisco, 419 out of the 500 people we selected showed up, and that was well above kind of the 70% yield we wanted to get. So that was something we looked at. We looked at how many people messaged, how many people actually stayed to day seven, so actually came back at happy hour and kind of did the Full value proposition of the product, and then we looked at how many people invited friends. So, 50% of the users actually invited friends after they used the app, and that was a huge number when you're really small. Half your user base is helping you grow, is half your user base is being your salespeople. So, to me, those are the kind of metrics you want to be looking at, and that tells you if you have a product that people …

AI assessment note: “our success metric is similar to a college, kind of, it's yield”

Q Can I ask, how did you think about the right time to turn on that monetization tap? When was that inflection point for you and going, okay, now we're going to turn it on and offer this, this, and this?

A Two answers to that. One was when we, we had to rebuild the stack again, and this goes into my engineering nightmares podcast, but, you know, we were migrating to what we call lead two point oh, Um, entire different backends. And so at that point we actually had built the billing systems into that new product. So we actually were able to take users money on that product. And then as far as like when we actually ruled it out to the users, we were actually behind the gun. We were pretty under the gun in the sense that we were running out of money. I was looking at the end of our runway and pretty freaking out about it. And so, you know, it was a, I wanted to launch it. And then I also de-risked the fact that monetization might be a complete disaster by taking a small bridge round from my insiders. I think it was Two or 300 K just to kind of have as rainy day funds in case all hell broke loose. So again, I think you'll notice the trends are it's kind of risk mitigation and having a lot of different kind of plans in the air and it's, it's more work for sure, but it's, it pays off when something doesn't go the way you, you want it to, you have a backup plan. So that was sort of the way I thought about it.

AI assessment note: “we were pretty under the gun in the sense that we were running out of money”

Q hear your, your primary tips on the best opening lines, but I do want to move to the fundraising element. You mentioned that the bridge round, and then we've spoken about some of the incredible investors that you have on board, from the likes of Cowboy to Sherpa to Alex at Ridge. I'm interested, how was the fundraising process for you, given the immensely competitive nature of the dating space?

A It's not fun. Uh, I mean, I don't think fundraising is fun for anyone. And to be fair, our, our first 75,000 dollars that we collected was very painless. It was, you know, people have relations with three people gave me 25 K checks. So that was easier than the normal process, but you know, the next 300 K was quite the uphill battle. I think that was, you know, four to six months of just kind of going to coffee meetings, talking to people, trying to get the money in. And so what I ended up doing is, is more or less a kind of a party round strategy where I had some awesome VCs in that kind of gave me the credibility and some great angels in that gave me credibility. And so I said, I think I can get A bunch of hundred K, 50 K checks and get this round to a million faster than I could by going and trying to get kind of a classic VC to lead the round in a dating space with a single founder with a product that the backend was not even a real backend. It was built on Facebook's parse, which is no longer allowed. So I mean, it's, uh, no longer alive. So, I mean, we had, you know, we kind of had an uphill battle as far as trying to get kind of a classically led VC round. So we really went the alternate route. I actually priced my own round and then got negotiated down a little bit, but ended up Kind of closing the rounds pretty much led by Amanda, I like to say.

AI assessment note: “It's not fun. Uh, I mean, I don't think fundraising is fun for anyone.”

Q invite makes you treat them so much more carefully, one. But I'm intrigued. You said there about the seven-day retention. In terms of retention, how do you think about that? It's obviously a problem that plagues the space more generally being consumer and also kind of romance and dating apps. Is the seven day the core metric for you? And how do you think about that maybe more longer term?

A It's not a core metric for us. I mean, for launches, it is, um, just because we, we look at it as a very focused event, but no, retention is an interesting one. You know, we, we have what we call good churn and bad churn. Good churn is when a user says, Hey, I need a timeout and they pay a dollar. That's a, we actually say, if you pay a dollar, we won't You know, your, your account's fine. You don't need to check in every day. You can kind of chill out. And so to me, if someone's willing to pay a dollar to kind of stay in the community, that's something we look at. That means they're, yes, they're, they're leaving the app, which, you know, is unfortunate, but that means it's probably for a good reason. What's not good churn is if someone's on the app and they haven't gotten messages, they haven't had matches, and you can kind of see from the data that they're falling out because they had a bad experience because no one messaged them. Um, and that's what we call bad churn. And that's, you know, that's what we're trying to focus our efforts on is What can we do in the algorithm to prevent that? Is it that we're matching them with people that have too many matches? Are we putting them in a different group? So it's really about kind of looking and making sure we're giving our users what we want is a match by the seventh day. So we're trying to figure out how our users can be shown …

AI assessment note: “It's not a core metric for us.”

Q No, I do exactly the same. I do want to finish. So on the next five years for you and the league, what does the exciting roadmap hold?

A Oh man, so many things. Uh, I'm actually working on a presentation about this right now, but a couple of things I'm excited about are merging online and offline officially in the sense that when you want to go out, To a bar in New York City. And let's say you're fresh off a breakup yourself. Which bar do you want to go to? And where are the people that, you know, meet your preferences within New York City? And are they going to the West Village? Are they going to the Lower East Side? And where should you go out with your friends that night? And so I think having a little bit more of a compass on a, you know, not in a creepy way by any means, but more, you know, I call it a heat map or a compass in the sense that it helps you live your life offline with more efficiency and more, feel more focused. And, uh, I guess increased probabilities of meeting someone interesting without having to kind of Change the way you want to live your life. And to me that, you know, when we get there, that's, that's what dating should be like. I should be able to go to a, you know, a music show that I wanted to go to anyway and happen to bump into someone, you know, that's there because I know that from this map that, you know, this is a good chance of, of meeting someone that's in my preferences. So I think really merging that so that we're not keeping our users online. We want to be sending our use…

AI assessment note: “a couple of things I'm excited about are merging online and offline officially”

Q Oh, I love that pricing of the round yourself there. I am interested. Party rounds are often denigrated because there's no kind of real lead who's willing and incentivized to really go to bat for the company. Having experienced this yourself, how would you respond to that? Has that been the experience that you found or actually is it completely contra that?

A I haven't really had the need to have any of my investors go to bat for the company. I don't know if that's just because I like to fight and I like to go to bat myself. But, um, you know, I, I guess I can't comment on that in particular. I've commented that when, when I do need help from my investors, I think they helped me just like they would if they had put in two million dollars or five million dollars, even if they've only put in 25 K. So I haven't noticed a difference based on their responsiveness or their willingness to take a phone call or give me advice. And so I really think it's about the people you have on your cap table and actual, you know, the names and, and not so much the funds. I think you want the funds because they have the connections that help the people with the names provide value to you. But I think at the end of the day, it's about the people. Do you, who do you want in your family?

AI assessment note: “I haven't noticed a difference based on their responsiveness or their willingness to take a phone call”

Q mentioned that the kind of the paying of the dollar, so to speak, to kind of have a bit of a rest I'm intrigued. One interesting element that a lot of consumer founders talk to me about is when to monetize and the willingness to make users pay. How do you think about that monetization aspect early on in the journey, and how did you approach it, do you think?

A Yeah, monetization is interesting. I think the, the kind of classic playbook, at least when we were launching was in 2014, was don't worry about monetization. It reduces your focus on the core value proposition of the product, which, which I a hundred percent agree. So we, we did launch without About monetization. But what I did put in was a test for monetization. So I said, I'm not going to focus on revenue. I'm not going to focus on building a billing system. The developer I had didn't even have the capability to build a billing system. So we actually couldn't have monetized even if we wanted to. But, but what I did is I created an HTML fake page where I said, Hey, you want to upgrade for 15 dollars? If so, click this button. And then we just said, great, you're upgraded. And we, we gave them the advanced features without charging their card. And so that gave me a conversion rate That I used for that year and a half, kind of while we were on free product to give me, I guess, peace of mind that, okay, worst case scenario, we're going to have X percent of our users pay us 15 dollars. So here's sort of what I could expense and here's sort of what my budget could be. And I think that, I think doing things like that is a way to, to de-risk the strategy of, okay, we're not going to focus on monetization, but how do we de-risk the fact that it could totally fail? So having that conv…

AI assessment note: “created an HTML fake page where I said, Hey, you want to upgrade for 15 dollars”

Q because before we chatted, and you got very passionate about the element of the art of the launch, as you called it, and kind of pre-gaming that launch. So before discussing the tactics of maybe how to do it, maybe more importantly is why in today's MVP world of Fast iteration and throwing products out there and testing. Why is this pregame necessary? What are the benefits do you think?

A Well, I think having users before you launch is a huge benefit because we actually leveraged our users prior to launching to tell other users that we were launching. So if you think of it as kind of a slow roll and you're, you're spinning a ball of yarn, you think you get a little, little tiny ball. And so as you keep going and as you keep talking to people and not getting them to download your app and meeting 30 people here. I mean, it sounds like small numbers and it is for sure, but it adds up. And once you're actually, you know, once you're at 300, that's actually a decent amount of people to say, Hey, we're having an event over here. Do you have any friends? You can forward it to them. Let's say we had a hundred people go to an event and that was a, you know, our beginning user base. We would keep leveraging them and, you know, come to another event, come to another event. And so we pre-gamed for five months while my developer was building the prototype. And I was kind of doing this wash and repeat shampooing of our users and trying to keep Stirring them around. And so I think my takeaway was if you can get people buzzing about your product before you launch, you can almost guarantee yourself your launch is going to be at least medium success. You're maybe not amazing. And if you can get press and can get all the other things to happen and you can put all the marketing pie…

AI assessment note: “having users before you launch is a huge benefit”

Q In terms of kind of embarking on that journey, I spoke to Alan Chu, one of your investors before. Before the show, and you embarked on the journey as a solo founder, I'm intrigued. What were your big learnings from that single founder experience, and you maybe disagree with the conventional wisdom of kind of always having a partner?

A I totally disagree with it. I mean, I, I say it's the same advice I give to single people when they're struggling with the dating game. I, you know, I say it's really hard to date when you don't know who you are, or what you want in a relationship, or what your definition of love is, and you know, all the, all these other things that you kind of need to be able to To enter a healthy relationship. And I think a company is the same thing. You need to find out, you know, who your company is, what it does. Does it have legs? Do you have a profitable business model? Is there a, you know, a service or product here that people want? And then once you know that, once you have that and you kind of have that truth, I think, you know, attracting people onto your ship is a lot easier. And so I think people try to do that too early rather than focusing on, you know, can I build something that delivers value? So I think actually a solo founder is, Is a nice way to really focus on that. You know, you have no distractions and you actually can keep a lot more of your company if, if you can figure it out without having to kind of find someone to share the burden with. So, you know, I, I feel like I have regained a lot of control of the company. It's, you know, in my vision, I have complete control over the direction of the company. And that was something that was really important to me. I didn't…

AI assessment note: “I totally disagree with it. I mean, I, I say it's the same”

Q hear your, your primary tips on the best opening lines, but I do want to move to the fundraising element. You mentioned that the bridge round, and then we've spoken about some of the incredible investors that you have on board, from the likes of Cowboy to Sherpa to Alex at Ridge. I'm interested, how was the fundraising process for you, given the immensely competitive nature of the dating space?

A It's not fun. Uh, I mean, I don't think fundraising is fun for anyone. And to be fair, our, our first 75,000 dollars that we collected was very painless. It was, you know, people have relations with three people gave me 25 K checks. So that was easier than the normal process, but you know, the next 300 K was quite the uphill battle. I think that was, you know, four to six months of just kind of going to coffee meetings, talking to people, trying to get the money in. And so what I ended up doing is, is more or less a kind of a party round strategy where I had some awesome VCs in that kind of gave me the credibility and some great angels in that gave me credibility. And so I said, I think I can get A bunch of hundred K, 50 K checks and get this round to a million faster than I could by going and trying to get kind of a classic VC to lead the round in a dating space with a single founder with a product that the backend was not even a real backend. It was built on Facebook's parse, which is no longer allowed. So I mean, it's, uh, no longer alive. So, I mean, we had, you know, we kind of had an uphill battle as far as trying to get kind of a classically led VC round. So we really went the alternate route. I actually priced my own round and then got negotiated down a little bit, but ended up Kind of closing the rounds pretty much led by Amanda, I like to say.

AI assessment note: “It's not fun. Uh, I mean, I don't think fundraising is fun for anyone.”

Q Listen, I absolutely love that element of sourcing your best Best friend. It makes me think you should be a VC, but how did that sourcing of a best friend on AOL translate to the league?

A Well, I mean, I like to think that I was interested in connecting with people digitally from a very young age. I think I recognized the efficiency of being able to talk to someone across the country when that was what I was excited and focused on. I was excited to kind of start building my new life there, and the internet let me do that, and so I think, you know, I saw value really early on from that. I remember I met my college boyfriend. I reunited with him through Facebook, so I'm a big Facebook fangirl. In the sense that any service that connects people to people they might not have met in everyday life, that people that are life-changing and transformative people, I have a lot of love and respect for. And so I think subliminally, maybe that, that sort of pushed me in this direction. I don't know, you know, I didn't grow up saying I wanted to build a dating site or a matchmaking site, but I've always sort of been a kind of on social network creep, I guess you can say.

AI assessment note: “subliminally, maybe that, that sort of pushed me in this direction.”

Q Can I ask, is it difficult to make the transition from contractor to employee and knowing when the right time is, but also getting them on board with a stat that's been developed by some Michael mercenaries, so to speak?

A It's impossible. I mean, I would say I've probably been through every engineering horror story you could go through. I was probably a whole nother podcast for like engineering nightmares podcast, but there's one I'm Raising my hand to be tapped for it. But yeah, I think in general, the contractor mentality, you can't convert contractors to employees. You just can't. It's their DNA. It's fundamental. I'm doing this to fund something else in my life, and that's why I'm essentially extorting money from people, and depending on what the resume is or whatever they need, there's some people we paid over 350 dollars an hour when I was pretty desperate just because they had a specialty or something that we needed and couldn't find, and so I think those people are not trying to join a team. They're not trying to build something. They're trying to make money for another Passion of theirs, and so I think it's trying to put a square peg in a round hole, and I think I learned that by trying to get two or three contractors on board, and really getting close relationships with them, but realizing that a duck's a duck, I guess.

AI assessment note: “It's impossible. I mean, I would say I've probably been through every engineering horror story”

Q Oh, I love that pricing of the round yourself there. I am interested. Party rounds are often denigrated because there's no kind of real lead who's willing and incentivized to really go to bat for the company. Having experienced this yourself, how would you respond to that? Has that been the experience that you found or actually is it completely contra that?

A I haven't really had the need to have any of my investors go to bat for the company. I don't know if that's just because I like to fight and I like to go to bat myself. But, um, you know, I, I guess I can't comment on that in particular. I've commented that when, when I do need help from my investors, I think they helped me just like they would if they had put in two million dollars or five million dollars, even if they've only put in 25 K. So I haven't noticed a difference based on their responsiveness or their willingness to take a phone call or give me advice. And so I really think it's about the people you have on your cap table and actual, you know, the names and, and not so much the funds. I think you want the funds because they have the connections that help the people with the names provide value to you. But I think at the end of the day, it's about the people. Do you, who do you want in your family?

AI assessment note: “I haven't noticed a difference based on their responsiveness or their willingness”

Q In terms of kind of embarking on that journey, I spoke to Alan Chu, one of your investors before. Before the show, and you embarked on the journey as a solo founder, I'm intrigued. What were your big learnings from that single founder experience, and you maybe disagree with the conventional wisdom of kind of always having a partner?

A I totally disagree with it. I mean, I, I say it's the same advice I give to single people when they're struggling with the dating game. I, you know, I say it's really hard to date when you don't know who you are, or what you want in a relationship, or what your definition of love is, and you know, all the, all these other things that you kind of need to be able to To enter a healthy relationship. And I think a company is the same thing. You need to find out, you know, who your company is, what it does. Does it have legs? Do you have a profitable business model? Is there a, you know, a service or product here that people want? And then once you know that, once you have that and you kind of have that truth, I think, you know, attracting people onto your ship is a lot easier. And so I think people try to do that too early rather than focusing on, you know, can I build something that delivers value? So I think actually a solo founder is, Is a nice way to really focus on that. You know, you have no distractions and you actually can keep a lot more of your company if, if you can figure it out without having to kind of find someone to share the burden with. So, you know, I, I feel like I have regained a lot of control of the company. It's, you know, in my vision, I have complete control over the direction of the company. And that was something that was really important to me. I didn't…

AI assessment note: “I totally disagree with it. I mean, I, I say it's the same advice”

Q Can I ask, is it difficult to make the transition from contractor to employee and knowing when the right time is, but also getting them on board with a stat that's been developed by some Michael mercenaries, so to speak?

A It's impossible. I mean, I would say I've probably been through every engineering horror story you could go through. I was probably a whole nother podcast for like engineering nightmares podcast, but there's one I'm Raising my hand to be tapped for it. But yeah, I think in general, the contractor mentality, you can't convert contractors to employees. You just can't. It's their DNA. It's fundamental. I'm doing this to fund something else in my life, and that's why I'm essentially extorting money from people, and depending on what the resume is or whatever they need, there's some people we paid over 350 dollars an hour when I was pretty desperate just because they had a specialty or something that we needed and couldn't find, and so I think those people are not trying to join a team. They're not trying to build something. They're trying to make money for another Passion of theirs, and so I think it's trying to put a square peg in a round hole, and I think I learned that by trying to get two or three contractors on board, and really getting close relationships with them, but realizing that a duck's a duck, I guess.

AI assessment note: “You can't convert contractors to employees. You just can't. It's their DNA.”

Q Can I ask, how did you think about the right time to turn on that monetization tap? When was that inflection point for you and going, okay, now we're going to turn it on and offer this, this, and this?

A Two answers to that. One was when we, we had to rebuild the stack again, and this goes into my engineering nightmares podcast, but, you know, we were migrating to what we call lead two point oh, Um, entire different backends. And so at that point we actually had built the billing systems into that new product. So we actually were able to take users money on that product. And then as far as like when we actually ruled it out to the users, we were actually behind the gun. We were pretty under the gun in the sense that we were running out of money. I was looking at the end of our runway and pretty freaking out about it. And so, you know, it was a, I wanted to launch it. And then I also de-risked the fact that monetization might be a complete disaster by taking a small bridge round from my insiders. I think it was Two or 300 K just to kind of have as rainy day funds in case all hell broke loose. So again, I think you'll notice the trends are it's kind of risk mitigation and having a lot of different kind of plans in the air and it's, it's more work for sure, but it's, it pays off when something doesn't go the way you, you want it to, you have a backup plan. So that was sort of the way I thought about it.

AI assessment note: “we were running out of money. I was looking at the end of our runway”

Q No, absolutely. Help me though, as an investor, if there was one thing that would be most valuable to you that an investor could bring, what would it be? A lot of founders say empathy. I don't often buy it. What would it be to you that an investor could bring that would be most valuable?

A Awesome engineers, which is again, the, one of the hardest things to be able to provide value to, even as a VC. So it's, you know, I would say sourcing engineers in, in Silicon Valley is probably one of the most difficult projects, I've had, we're just now getting to a point where we, we can start to actually recruit kind of consistently and bring people on, but it's been hard. I think the dating space doesn't always attract kind of the, the Google type engineers. It's, uh, I think people kind of write it off sometimes when it's actually quite fascinating data and actually quite tech forward, at least the way we're running our company. But I think dating gets kind of a bad rap. And so a lot of people will say, oh, I don't want to go. They think of match.com or they think of these kind of old school visions in their head. So I think we, we kind of run up against that as well. Um, I think the other thing that VC does for me is, is just, you know, tell me what their other portfolio companies are doing. I think, especially as a single founder, I sometimes feel like I'm paranoid or crazy. I'm like, is this a good idea or a bad idea? Or am I running the company right to think that we should be thinking about real estate or, you know, sometimes crazy ideas. And so kind of having them, you know, to run by both from their personal experience, but also connecting you to other founders in…

AI assessment note: “Awesome engineers, which is again, the, one of the hardest things to be able”

Q So, your favorite book and why? What must I read on my next trip out to the West Coast?

A I'll give you my, my childhood favorite book, which was The Giver, and the reason I would say that book resonates with me, it's just always stayed with me as I, yeah, yes, I've gone through my life journey just because it, It was such a book of self-discovery, and I read it at such a young age when I was kind of understanding the world, and so I think I always just think back on, you know, he learned that there was a history, and there was a future, and sometimes I feel like, you know, when you're going through life, you start to realize, oh, wow, I took, you start to see the world a little bit differently, I think, as you age, and that's now, I understand the giver a lot more, I feel.

AI assessment note: “I'll give you my, my childhood favorite book, which was The Giver”

Q and we had Leah from TaskRabbit and Fuel Capital on the show the other day, and she suggested that with marketplaces, which in some case, you know, the league is, to a certain extent, that one side's always going to be unhappy to an extent. I'm intrigued. Would you agree with this, Kind of having seen the observations with the league, and how do you think about finding that equilibrium?

A Yeah, with dating, it's interesting, because you, you can kind of, there's a lot of different marketplace dynamics in play. There's obviously the kind of gender one, which is, you know, the majority of our user base is men and women seeking each other, so you have that, and then I think for us, um, because we have a wait list, and because we're a curated community, we can actually choose what ratio to keep the league, so we could make it way more female, less male, or we could make it way more male, less female, and you'll notice You know, I don't know if you, what other dating apps we use, but most of them don't curate their community. So it's just about who decided to log in that day. And usually on average dating apps are about like 70% active users are men, 30% women. So usually women are very outnumbered. They get a lot of attention. You know, it's pretty easy to be a woman on a dating app on most of them. And I would say on the league, it's actually quite hard in the sense that we keep the ratio of 50 50. So, you know, the women feel like they're kind of doing less well. They say, I'm not doing as well on the league because I'm on these other apps. And it's, you know, we're like, it's not you. It's literally just we're keeping the ratio balanced. And we're doing this as a service to both, you know, women and men, but it does change kind of the experience that people are u…

AI assessment note: “we keep the ratio of 50 50. So, you know, the women feel like”

Q Well, I died. It's a twenty-minute show, so we might have trouble fitting it in. But I want to get started today by discussing a little bit about you. When you were a little girl, did you always dream of changing the world of romance and dating, and what was the start of the league?

A I love that you asked that question, because I was actually known as Internet Amanda as a girl, because I was sort of crawling the social networks before there were social networks, so I was one of the people that used AOL Instant Messenger as a search for friends tool. There was buddy chat, and if you filled out certain profiles in buddy chat in AOL, you were able to find other people that matched your middle school, for example. So that's actually how I sourced my best friend, who's still my best friend to this day. I sourced her from AOL Buddy Messenger, because I found a guy who went to my middle school where I was moving to in three or four months, or maybe I was even six months ahead. That's how weird I was. And so he connected me with a girl named Molly. He said, Molly knows everybody. She'll hook you up. You'll have a good experience in middle school. Be friends with Molly. So I said, cool. That sounds like something I can do. So I messaged her and said, Hey, I'm this new girl coming to school. You want to hang out when I get there? And so we became fast friends on AOL, but I always joke that I guess the rumor was around school that Internet Amanda was coming for, for about six months in North Carolina, and so they all thought I was kind of crazy, because I was coming from Silicon Valley, where we kind of grew up around computers. My dad worked in startups, helped build…

AI assessment note: “I was actually known as Internet Amanda as a girl”

Q So, your favorite book and why? What must I read on my next trip out to the West Coast?

A I'll give you my, my childhood favorite book, which was The Giver, and the reason I would say that book resonates with me, it's just always stayed with me as I, yeah, yes, I've gone through my life journey just because it, It was such a book of self-discovery, and I read it at such a young age when I was kind of understanding the world, and so I think I always just think back on, you know, he learned that there was a history, and there was a future, and sometimes I feel like, you know, when you're going through life, you start to realize, oh, wow, I took, you start to see the world a little bit differently, I think, as you age, and that's now, I understand the giver a lot more, I feel.

AI assessment note: “I'll give you my, my childhood favorite book, which was The Giver”

Q No, absolutely. And you mentioned the bridge around there. I spoke to many of your investors before the show and a commonality that all mentioned was this incredible scaling and growth trajectory that you have enjoyed with the league. Unpacking it a little, Tina Sharkey at Brandless asks, how did you hone your city by city playbook, and what did that decision-making framework and process look like?

A I wish it was a really complicated answer, but again, filing this under the engineering nightmares thread, I guess, you know, we were behind on launching in the sense that, you know, we had people knocking down our doors saying, when is my city live, and we were only in San Francisco, and so, you know, we were on this pretty crappy MVP product that was, you Actually breaking down in the sense that you couldn't, when you log in, it would take about four or even five minutes to get your matches every day. And so it was, you know, we were having like massive scale issues. And so what we ended up doing was deciding that in New York, for instance, we had over 10,000 people on the wait list. So we said, okay, we're going to kind of have New York be our very last city. We're going to kind of bandaid this infrastructure up until we can. And then we switched focus and started rebuilding that new product. So Because of that, we were way behind in all the cities. So by the time we kind of were in a good place from a technical and a product perspective, we were kind of way behind where we probably should have been from a city launching perspective. So I guess we could just, we were lucky enough. We have a wait list in the app. And so we're constantly, you know, anytime someone says to download the league, anyone, anywhere can. And so these wait lists are building up in the background while…

AI assessment note: “which cities have the most people who've already registered”

Q Well, I died. It's a twenty-minute show, so we might have trouble fitting it in. But I want to get started today by discussing a little bit about you. When you were a little girl, did you always dream of changing the world of romance and dating, and what was the start of the league?

A I love that you asked that question, because I was actually known as Internet Amanda as a girl, because I was sort of crawling the social networks before there were social networks, so I was one of the people that used AOL Instant Messenger as a search for friends tool. There was buddy chat, and if you filled out certain profiles in buddy chat in AOL, you were able to find other people that matched your middle school, for example. So that's actually how I sourced my best friend, who's still my best friend to this day. I sourced her from AOL Buddy Messenger, because I found a guy who went to my middle school where I was moving to in three or four months, or maybe I was even six months ahead. That's how weird I was. And so he connected me with a girl named Molly. He said, Molly knows everybody. She'll hook you up. You'll have a good experience in middle school. Be friends with Molly. So I said, cool. That sounds like something I can do. So I messaged her and said, Hey, I'm this new girl coming to school. You want to hang out when I get there? And so we became fast friends on AOL, but I always joke that I guess the rumor was around school that Internet Amanda was coming for, for about six months in North Carolina, and so they all thought I was kind of crazy, because I was coming from Silicon Valley, where we kind of grew up around computers. My dad worked in startups, helped build…

AI assessment note: “I was actually known as Internet Amanda as a girl”

Q Listen, I absolutely love that element of sourcing your best Best friend. It makes me think you should be a VC, but how did that sourcing of a best friend on AOL translate to the league?

A Well, I mean, I like to think that I was interested in connecting with people digitally from a very young age. I think I recognized the efficiency of being able to talk to someone across the country when that was what I was excited and focused on. I was excited to kind of start building my new life there, and the internet let me do that, and so I think, you know, I saw value really early on from that. I remember I met my college boyfriend. I reunited with him through Facebook, so I'm a big Facebook fangirl. In the sense that any service that connects people to people they might not have met in everyday life, that people that are life-changing and transformative people, I have a lot of love and respect for. And so I think subliminally, maybe that, that sort of pushed me in this direction. I don't know, you know, I didn't grow up saying I wanted to build a dating site or a matchmaking site, but I've always sort of been a kind of on social network creep, I guess you can say.

AI assessment note: “subliminally, maybe that, that sort of pushed me in this direction.”