Ignite Startups: Building Real-World Community with Dorothy Li of Real Roots | Ep220

what's an insight about adult friendship building do you wish more people understood i wish more people understood that it takes a long time and it's normal for it to be awkward in the beginning if you expect friendships to feel like magic from in every second from day one to day two to day three you're just not going to lean into any friendships that will become meaningful over time i remember the first day of business school i joined a large group of people who are complete all strangers to me and i And every conversation felt like fishing, like, what do we have in common? I just didn't know. And it felt isolating even though I was with so many people. But I remember that moment in time vividly because you fast forward three months later, six months later, one year later, those people became some of my closest friends and almost family-like members. So every relationship starts at the beginning where it's really awkward. If you share your same life stage, then you have so a breath of uh topics to discuss that really cement that friendship and as the friendship evolves maybe life stages can diverge a little bit which is normal and that friendship still has the foundation to maintain but in the very beginning we find it's super important to be in the same life sleep hey everyone welcome back to the ignite podcast today we're thrilled to have dorothy lee on the mic she's the co-founder and ceo of real roots the startup reimagining how adult women build friendship circles via guided matched experiences she brings deep operations and growth experience and a strong mission to this work really excited to dive in thanks for coming on thank you thank you for having me i'm excited yeah so i'd love to get your background what's your origin story well my background from the very beginning is my parents were both entrepreneurs we grew up in i grew up in socal and i just saw how two immigrants who barely knew the country could really take charge of their own destiny and make a really great service that a lot of people. So they're both structural engineers, so they built an engineering firm. And as an adult, I've always been working in startups. So I worked in two mission-driven edtech startups in the beginning of my career, E-Academy, which is mine, and then Cambly, which I was an early employee at. And both I chose because I just felt at that time in my young adulthood that education was the most important problem I could solve for the world. But as I... you know, matured and to spend more time living as an adult, I found that the greatest problem that I faced in my own life was the sense of isolation when I would move from city to city or change life stages or go through a breakup or get in a new relationship. Anytime something like that changed in my life. It created a need for new people that supported that new life stage. And it took me a long time sometimes to find that new group. During that period, I felt isolated. I oftentimes would be following a move. So I would go from a community where I was like very, you know, ingratiated and felt really supported into a city where I knew nobody. So I wanted to build a solution for myself foremost and all the women like me. That's amazing. And we met BYC. Obviously, we were an investor. What really struck us was the momentum and traction. You know, like you guys were some of the highest ARR coming out of the batch that we've ever seen. And it feels like you kind of struck kind of the right idea at the right time. What do you think is causing the kind of the rise of social isolation? You know, there's this famous book, famous for me, Bowling Alone, that came out probably 20 years ago. And it talks about this phenomenon in America where we're increasingly isolated from each other and kind of just, you know, maybe we're just stuck in our screens. But I think it was before social media even. What do you think is kind of and maybe social media compounded it, but maybe you can talk a little bit about the impetus for real roots and kind of, you know, your own personal lived experience, which you just talked about, but also like kind of like economic and social zeitgeist, especially in the United States. And this is a worldwide phenomenon. Do you see or is this like isolated to the U.S. and more like Western countries? Yeah, I mean, you raise a really good point. Loneliness has been a growing. uh epidemic for the last 20 30 maybe even 50 years as illustrated by books like bullying alone and that i believe is is global what is happening now is not so much that loneliness is new it is growing of course because we're more geographically mobile than ever before and women and men are getting married later than ever before meaning there's this longer period of time where your your friends are your family so those two trends are only getting worse but what is really what changed um In a pivotal sense overnight is the pandemic. And the pandemic was a period of time where everybody felt lonely at the same time. And because of that, it made it socially acceptable to think about the problem at large, like how does this span into other parts of my life, even when I'm not in the pandemic, became normalized to talk about being lonely and also other mental health concerns as well. And off of the back of the pandemic, a lot of people share the same struggle of rebuilding communities they lost. during the two years of being a little bit more remote and also rebuilding their own social skills as well. And because of that shared cultural resonance of us all going through the same thing at the same time, we have destigmatized talking about loneliness. maybe 10 years ago we would have said we would have been hesitant to say that we were lonely because it would have made people feel that there was something wrong with us if we couldn't find our friends but now it's pretty clear that loneliness is just something that happens to all of us from time to time and we all need to rebuild our social circles when we change life stages because of that there's openness now especially with young women to admit that you're lonely and if you can admit that you're lonely you can find solutions for that problem yeah i have i have this problem myself you know my personal live experience is i moved out of the bay area during covet yeah so i entered this new area and i'm basically just living in my house you know with my family for a year before you know covet kind of lets up and i can go out and do stuff with the local community we meet some parents you know we kind of make a little bit of friends with some preschool age parents but most of my friends come from basketball right you know going out and playing you know pick up and league basketball you know two or three times a week and then recently i started you know because i'm out east of sacramento you know so i'm pretty far out here where nobody cares about startups or vcs and well not not nobody but pretty much and so recently i just uh i saw how much fun my wife was having with her book club so i started a men's book club amazing it's good we just had our first meeting we read extreme ownership which we all voted on which i had read like you know almost 10 years ago when it came out but it's fun you know you just get together have some drinks talk about the book and i think guys too also need like an excuse to get together You know, I noticed my wife is able to kind of, she's a social butterfly. I mean, she goes out and just, she has her pickleball group and she has her this and that group. But maybe you could talk a little bit about, okay, so we know the problem, right? Women's loneliness. So what is the solution? Walk us through the early build of Real Roots. How did you define the problem, validate it, arrive at the kind of initial product? Yeah, absolutely. Well, first of all, I wanted to point out that paying for a way to find new friends is not a new phenomenon. What's new here is that we're talking about it openly. Women have been paying for sororities. They've been paying for book clubs or social clubs for many, many decades. And a lot of times when women join one of those institutions, they're actually looking to rebuild community or find new friends, but they're doing it under the guise of saying they want to do something else. And the friendships are almost a byproduct. But we're now turning that on its head and we're just saying openly, this is created for friendships. And because we can say that, we actually can design a program that specifically targets the conditions you need for friendships to occur so that we can create high quality friendships in a shorter period of time in a very consistent fashion. So that's what's new about Real Roots is we systematically create the three conditions needed for friendships to develop. And those three conditions are core compatibility amongst the participants. which we screened through a matching survey, as well as an AI matchmaker, which women talk to for five to 10 minutes. Wow. So you got like this voice AI kind of onboarding flow. Yeah, yeah. I think I told you my wife actually has a voice AI startup. You guys should probably talk about this. Yeah. Yeah, I would love to. It's called a little plug, your360.ai, so you can look that up. Amazing. We'd love to talk that out. Voice AI is magical in many different ways. Well, it's starting to feel more and more human-like. So it can ask follow-up questions that deepen upon the tangent the person is going on. So you can get to a customized route of where that conversation and discovery goes versus just going through a survey, which can be a little bit more one-track for every individual. So that's one really amazing thing. But the second thing is... Voice AI can pick up on nuance in a personality that previously was only able to be done by a human. In the very beginning of Real Roads, I actually matched people myself, but... as a result of a short interview that I would do in person or via video. And I found that I was able to do a better job at matching people than when I only relied on the survey. Of course, because there's this additional human layer where you can pick up on the vibe of a person and also the subtext behind some of the answers they're giving. There was just, before Voice AI came out, there was just no really good way for me to replicate that at scale without hiring a really large ops team, which would be unwieldy. That's important. It's an important thread to tug on, something that VCs care a lot about. like the why now yeah before you'd have to do these like survey monkey kind of survey things and then have this like whole team kind of doing this stuff and now ai and agentic workflows can automate a lot of this curation and connection and discovery we are very lucky that we are kind of mirroring two very important trends one is increased focus on in real life connection and we talked about just now with like the increased awareness of loneliness and people willing to invest in there social well-being so that's one and the other is finally we're able to create matching and also experiences that are very customized at scale without a lot of human labor and previously the best experience if we had created real roots maybe 10 years ago we would have created this quality of product we would have to have humans interviewing people and humans custom designing experiences for that group and each group would be unique and that would that would have been a very different price point than what we're seeing today yeah that's interesting so how does your matching algorithm and process look at a high level like what have you what's what's some insights or surprises that the audience might be surprised to learn about yeah well i think what's really interesting for me is like when i first started working on real roots i thought that there was going to be so many factors that matter in a friendship i really thought that there might be like 50 to 100 factors that really matter but and and i i still think that's true but there are a few factors that matter the most it's people's people really value others who are in the same state as them and who can who lean in and support them so a lot of it is even just priming on the individual side and that's part of why it's so important for us to create facilitated experiences because we create environments where everyone's leaning in validating and sharing deeply about one another so that's like one so we basically de-risk and guarantee one really important trait of matching even before we match which is everyone's mentally open and everyone's going to be sharing deeply about themselves and receiving openly about other people's shares so that's guaranteed and then when we look at the traits that we use for matching we look at three major types of traits The first type is traits that people can define about what they're looking for for a friendship. And we use open-ended responses for this, a voice AI component as well as a version component. And we ask people, you know, what's important to you specifically, like Brian, what's important to you in a friendship? And you might say, I'm looking for, you know, someone who lives nearby and where I live, I don't. have a lot of tech people to talk to so i'm specifically looking for that and i'm i can be a little bit more generous with mismatches and other parts of of my life or other parts of the personality i literally have a tech guys you know we call tech bros chat so every time i meet like a tech bro you know that's like you know yeah i put him in a whatsapp group so we can all like communicate because there's so few of us up here you know east of sacramento like anytime i always like you work in tech like that's amazing i love that versus like the silicon valley like everybody works in tech and it's very rare you meet somebody who doesn't you know that's really clever of you because one another major barrier of friendships is you just don't see them ever again you have that initial click and then if you don't take action like what you do in terms of creating a group and then maybe organizing another follow-on that connection just goes off into the ethers and that's that's another thing that we do in real reasons we ensure that you see the same people enough times as long as there's mutual buy-in we make sure you see each other enough times for real connections to form yeah but before going on a tangent going back to the question of matching so the first bucket of traits we look for is just what you self-report is important to you because you are self-aware to a certain extent as to what's missing in your life the second bucket is traits that you maybe aren't as self-aware about that are important to you but we are because we look at a lot of we look at tens of thousands of success outcomes but there's kind of the explicit what i think i want and then there's like the implicit yeah what you can kind of discern from maybe some stories in my background or like hey tell me a story about your uh your best friend or tell me a story about a a friend that you wish you had in your life right now or you know yeah yeah an example of this might be we might ask you whether you're extroverted or introverted in initial interactions like how socially comfortable are you and if someone we've noticed that people who are a little bit more anxious in the beginning or a little bit quieter in the beginning they prefer or have better outcomes with people who are more extroverted or social in the beginning because that personality type can draw them out. And that's something that a lot of people who identify as maybe slower to warm up aren't self-aware about. But we are because we look across a large set of data. Other examples of this are like if they happen to be from the same hometown or same region as you are from, you might not know that that's super important to you. But statistically, we could see that that is important for friendships. And even more superficial is like even if they were in the same clothing item as you, if you have an aura ring and they have an aura ring or you like band T-shirts and they're wearing a band T-shirt, things like that even predict friendships. And then the last bucket is the bucket that voice AI has been really useful for, which is traits that people are not very self-aware about. So it's very hard for them to self-report. And because of that, we have to use an external third-party assessor. Examples of this is your level of quirkiness, your level of emotional stability, your level of thoughtfulness, even your intelligence to some degree. A lot of these traits can be important for matching, but people are not. very good historically at self-reporting those traits so we use voice ai as well as open-ended survey questions where people write in almost an essay format response we use those two inputs to kind of determine those traits really fascinating so i'm guessing you have some fun success stories about some of the matches and groups you've created do you have any that come to mind off top of your head yeah definitely well countless bridesmaids But the most fun story I had was one of the first groups I ever ran. And I ran them by, I matched them by hand because we didn't have tech back then. You're a concierge. You're trying to find product market fit. You didn't build the tech first. You're a good founder, right? You kind of concierged it first. Yep. Gotcha. definitely i guided it myself as well so i was the first guide at real roots and that initial group i launched on the campus of stanford actually so it's mostly the the wives and partners of business school students and they are still hanging out today and their partners are closer as a result of their wives being such good friends i bumped into one of the male partners of the one of the women that were in my initial group and he says that they're still hanging out and they become best friends the men have become best friends because of their weekly dinners yeah that's that's funny you mentioned that because uh guys don't really make friends we make friends with our wives friends husbands that's very true yeah like you almost have to like you meet you meet these other husbands and other dads right and the dads are dads of your kids you know kids friends or or the husbands of of your wife's friends and that's literally how like middle-aged men make friends yeah like you like beer yeah i like beer okay cool you like basketball not like football okay i like football and like that's it you know so easy going you've probably looked at this and consider this as you're building the company what do you think those gender differences are guys seem to sort of just sort of fall into friendships maybe easier than women what is that gender difference if any at all well if you look at research women tend to get emotionally deeper with their female friends so because of that i believe that because of that they're pickier you know in a way like they identify traits that they want to be around more and trace that they are pushed against and they want to distance themselves from a little bit more and that's why the matching is so important yeah it's almost like it's almost like a marriage right like a match.com gotta be really compatible to be friends as a woman but like guys can be like i don't know like beer like let's go watch a game yeah because then later like you know it's funny though like later i think guys are more likely to lose friends too So I think maybe we're easier to make friends and easier to lose friends. And I've done that over the years where I'm just like, after you get to know a dude for a year, you're like, oh, I kind of don't like you. I didn't realize it before, but you're out. I shouldn't have been friends. Why am I friends with you? And this is how guys talk to each other. I can't believe I'm friends with you. You're such a piece of shit. You know, like guys literally like do that, like in a joking way, you know? Yeah, yeah, yeah, totally. I can't imagine. And then you end up with these friends as guys. And I have friends like this where you're like, can't believe i'm friends with you you know but i've like been friends for decades and so you can't like just walk away from that you know yeah you have a ton of sheer context right that makes that makes a lot of sense well men and women statistically do bond differently of course we have to be aware that there are individuals um on inside of each spectrum that you know maybe don't fall into some of these generalities that we're talking about. One common difference that we notice is that women bond through deep conversations first and men bond through shared activities first and deep conversations coming much later in the friendship. And because of those differences alongside other concerns as well, that's why we defend real roots for women first. Yeah. So what happens next? So, you know, the ladies on board and in the area, what's the next step in the process? Yeah. So ladies on board, they do. talk to an AI matchmaker. They fill out a brief survey and we match them into a group of compatible others. They get to meet their group in person one evening alongside a guide who is our point person and facilitator for the evening. And she leads icebreakers and deep conversations. So it makes it really easy even for quieter people. How many people are there in the group? About 10. About 10. Okay. So that's enough to have a couple side conversations going at once. Yeah. actually you know we we make it a group conversation that's why it's so important to have a live facilitator it's very common without facilitator for you to talk to just one or two people the entire night and not be able to form an opinion about the rest right and it's also really common to not go super deep because you would Generally, we're taught to just stay on the surface in initial interactions. But that facilitator just is able to launch in with some meaningful icebreakers and deep conversation topics so that you peer under the hood very rapidly. After that evening is done, you can get to decide, do I love my group enough where I want to commit to six more shared experiences with this group? Or do I want to get rematched? About 50% right now. Continue on. And then the other half. Interesting. Half go, you know what? I want to do another intro dinner kind of thing and try this again. Yeah. Our matching is getting better over time, but yeah, that's what it currently is. And so half, so out of 10, five will say, hey, let's meet again. Yes. Let's pay for the program, which allows us to have RealBreaths coordinate and lead six more meaningful experiences for us. Interesting. So how do you price it for the first meeting versus the six additional meetings? The first meeting we consider internally like a paid trial. It's $25. You get matched and you get that guided experience for the first evening. And then to continue on, $290 for six more. $290, okay. That's pretty affordable to make some friends, I think. And then out of 10, the five decide to do the six more. And so then it's like really a core group of five? Or do you try to match more people? Like what's the ideal group size going forward? That's a really good question. It's still 10, maybe eight to 10 is the ideal group size going forward. However, we find that groups, typically they decide together whether or not they join so either a whole group leans in together or a whole group leans out together that's how we know that matching is super important because when we get it right we really get it right and so the five would maybe do another dinner with five new something like that yeah so five have leaned in and said hey no like i'm leaning into this group and five are leaning out you do another intro session guided session with five new and try to get it up to eight to ten well sometimes but the most common outcome is people the whole group joins or the whole group doesn't join so there's really matching that needs what's more binary it's more binary yeah okay sometimes there are groups that are mixed and then we need to match them with another cluster that's compatible but for the most part we see a binary outcome that's interesting what have been some of the more interesting correlated traits to leaning in versus leaning out group dynamic when we get it right the whole group leans in yeah it's so fascinating it is so fascinating i almost think it's a snowball once five or six women have leaned in the rest lean in rapidly right yeah it's kind of that's kind of interesting social dynamics and then what are the next six sessions look like what what are those so because our stated goal is to help people make new friendships we're able to create in real life experiences that are extremely conducive to just that so each experience contains an activity and also deep conversation components all led and facilitated by the same guide the activity component is different each time and we strategically surface a different part of the person's personality each time so one night might be more arty one night might be a sheer challenge like an escape room or a scavenger hunt and then and another night might be board games and then and so on and so forth and it kind of depends on the group because you have all the insights on what they like what they don't like yeah Absolutely. And then each night we have a different vein of conversation topic. So one night we'll be talking about friendships, the next one family, the next one career, et cetera. But the goal is by the time you are done with a six week series of shared experiences, you feel like you know a little bit about every dimension. Is it six sessions over six weeks or is it like every other week? And then what happens? So six weeks have gone by and now we're roughly two months in and then what happens? And then we have a subscription pickup. And we're still figuring out what it looks like, though. And we've been experimenting with a number of different solutions. So if you can imagine, our value prop is matching plus the creation of meaningful experiences, right? That's our core value prop. After the two-month period, you might have found a core group of people that you are really excited about. So your need for friendship matching, whereas it might not be gone, is decreased. But your need for the planning and coordination and curation of meaningful fun experiences hasn't decreased. So you can imagine the follow on product just being a planning product for the group. Or you could also imagine us adding in different types of matching that you still have a strong need for. It might be more friends. It might be specialty friends like professional groups or neighborhood groups or mom groups or, you know, special identity groups like for me, maybe female founder groups, etc. So we're still exploring what it looks like going forward. Yeah, that's a good problem to have, though. I mean, if you're getting people through the funnel and then it's like, OK, how do we keep them engaged on a platform? You think about rolling this thing out. I mean, I would imagine you have to kind of do it city by city. and balance supply and demand and all that stuff it's kind of a semi-marketplace model how are you thinking about that yeah we're a three-sided marketplace model so we definitely roll out city by city like you described but i think what has surprised us with a lot of investors is uh we're our deal launch motions is very streamlined as soon as we tag in a city we can pretty much serve them like we have a very small list of things that we need to do in order to serve a city so we launch new city potentially every four days but that being said once the city is launched it is a marketplace we'll launch a city even if we have enough demand for one group because we might as well that group is well matched they're ready to go might as well launch but as we get bigger in that city as time goes on in that city we get bigger through word of mouth and through marketing efficiency we're able to form many more groups in that yeah I'm guessing the guide here is kind of remote right because you can't have a guide in every city or do you see like kind of the uber model where you have a guide locally kind of evening doing stuff the latter it's the uber model so we are a three-sided marketplace we have users we have guides who are 1099 workers just like uber drivers and then we have venue partners host some of these meaningful experiences that we're at like for example if we're hosting ping pong it would be with a ping pong venue or if it's a book club or something it'd be maybe at a restaurant or something like that so those are the three sides so before we are able to tack on a geo we ensure that we have some liquidity on all three sides right yeah yeah that's smart how are you thinking about growth levers i mean i would imagine you know you're getting some good word of mouth but how do you think about kind of filling that funnel as you roll it out yeah that's a really good question so we're super early we just don't know yet We're experimenting with a number of different new growth channels. So we have one channel that works well for us, word of mouth, of course, and two channels that work well for us, word of mouth, of course, and then Instagram as well, where we post organic and also paid content. And we just haven't really figured out any other channels that work yet. I would imagine Instagram ads are pretty effective. They are definitely effective. Then you have to think if they're effective, probably influencers are effective and probably TikTok is effective. we just need to spend the time to experiment and grow these things out yeah keep in mind we currently only have three people so super early startup super early startup with a lot of traction with the right idea at the right time it's a great investment thank you so looking ahead what are you excited about over the next you know 12 to 18 months i'm really excited to grow the team and to experiment a lot more with retentive products so what comes next for our engaged user base right they They loved Real Roots. What's the next thing that we can solve in their lives? And then, of course, how do we attract more users through new acquisition channels? Yeah. So we're going to figure out the next stage. I'm excited. So exciting. Let's do some kind of wrap up questions. What's an insight about adult friendship building? Do you wish more people understood? I wish more people understood that it takes a long time and it's normal for it to be awkward in the beginning. If you expect friendships to feel like magic in every second from day one to day two to day three, you're just not going to lean into any friendships that will become meaningful over time. I remember the first day of business school, I joined a large group of people who are completely all strangers to me. And every conversation felt like fishing. what do we have in common i just didn't know and it felt isolating even though i was with so many people but i remember that moment in time vividly because you fast forward three months later six months later one year later those people became some of my closest friends and almost family like members so every every relationship starts there beginning where it's really awkward yeah so the lesson is you can go spend 150 grand on an mba like we did to make some friends for like 250 unfortunately or like like 300 bucks on real roots you know so it's it's funny it's not too far off from the truth it really isn't oh i did my initial user interviews were on campus at sanford and i remember one of my classmates told me his primary reason for going to business school is to build his community because he wanted to meet new friends. So that was... Some of those friends are priceless. I mean, I wouldn't be a VC if I didn't get my MBA. Because the people I met and the exposure I got and the career acceleration I got and the network I got led to Team Ignite and what I do now. I'm not confident I would be doing exactly what I'm doing right now. That's an amazing thing to hear. You know what? I feel the same way. Yeah. Yeah. I mean, so if you're listening and thinking about getting an MBA, you probably should. just go spend 150 200 grand whatever it is now you won't regret it you might but i think if you're looking for a community that can really accelerate you um business school is amazing if you're looking to learn skills that you can't learn anywhere else maybe not as much so because i i would guess you can learn yeah you could just go watch some youtube videos if you want to like learn you don't have to go to business school or just read some case studies you know case study breakdowns you'll get the gist of it i think you want to build a network, it's pretty unparalleled. What's cool I think about grad school is everybody's at the same stage of life as you are. You're all like, you know, 25 to 35, somewhere in there, 25 to 30 and kind of like not, you know, kind of not sure about what they really want to do. Like maybe, you know, investment banking, maybe start a startup, maybe I'll be a consultant. Like everybody's in the same boat, right? Yeah. Yeah, definitely. You're in the boat with a bunch of the same people at the same life stage. And that's some of the matching stuff, right? Like, of course, you have a lot in common. So you make really deep, lasting friendships because you're all at the same life stage. It's kind of like, you know, when you go to high school or college. Yeah. You're kind of thrust into this experience together at the same life stage. You're just going to make friends. Absolutely. Especially at the beginning of the friendship. If you share your same life stage, then you have so a breadth of topics to discuss that really cement that friendship. And as the friendship evolves. maybe life stages can diverge a little bit, which is normal. And that friendship still has the foundation to maintain. But in the very beginning, we find it's super important to be in the same life stage. And I'd hate to say this because it's going to sound, I don't know, maybe bad, but you're also with the same level of intelligence people because there's a GMAT sorting mechanism. So like if you get a 720 in your GMAT, you could go to Stanford or Berkeley, Harvard or whatever. Like if you get a 650, you're probably at like, you know, like some UC school. And if you get a 600, you're probably at some state school. Fair. Yeah. It's fair. It's kind of true. So if you could go back and do one thing differently, what would it be? In life or in business? Okay. Well, in life, I mean, I'll get vulnerable here. For a long time, I was scared that I was single for so long. And I spent most of my 20s single and a chunk of my early 30s single as well. I saw this meme the other day where a woman was like, I spent my entire 20s saying no to a bunch of guys that would have been great husbands. And now I'm chasing a bunch of guys in my views that I would have not even given the time of day in my 20s. Something like that. It was like some meme like that. I know that's very relatable. I was lucky enough to find an amazing partner and husband now. But I do wonder what that other life would have been like if I had leaned in a little bit earlier and had a partner for a longer period of time because. my life is just really happy now i have a great partner and there's no doubt in my mind that if you're in a happy marriage you're happier than a single person and of course if you're not in a happy marriage i think you're less happy than a single person so true so it's hard to know what the counterfactual would have been would i have been more happy or less happy but i wish i had met my current partner earlier so i could have enjoyed this period of you know without kids or work and supporting one another longer because this part is really fun i've known my wife long enough that i went to her 21st birthday i'll say that and we were still we were still just friends at the time and i'm in my mid 40s so and then so we've been together since that age over yeah 23 24 years now wow how long were you friends for before you made i wouldn't call it friendship i'd call me like chasing her and courting her for like seven months but yeah we're friends i was in the friend zone for about six months not bad i mean it's it's really hard to get out of the friend zone so you clearly did it right yeah i could be a pompous cocky and especially 25 years ago when i was in my early 20s and so when she met me she was like who's this guy you know i was wearing gel in my hair you know like spiky hair and i'm not into i'm not into this guy and i had to like yeah i had friends around us that were like dude why don't you just like hang out with her and be yourself you know and that really worked you know oh that's amazing what if you're learning that being yourself is better than being any right yeah i don't try yeah that's the lesson for any guys listening in their 20s just be yourself you know yeah and if and if being yourself isn't working then like she's not the right girl for you yeah the same thing applies for all human relationships yes so let's get back to business what would you change yeah Yes, this is harder to be sure about because I definitely don't know what the counterfactual would have been like, given that the timing of hitting the market with real loose right now is so good. But I think a lot of female founders like myself struggle with feeling ready to start a company in the very early stages of our career. So I definitely felt that way. I mean, I did start a company, but it didn't go that well. And instead of getting back up and starting another one, I joined. um a startup as an early employee learned a whole bunch which was amazing and makes me a much better founder than i would have been otherwise but i do wonder did i need to be at a company for six and a half years to get ready and i wonder if that would that's because you know as women we second guess ourselves a little more and i waited until i was super super super ready and then i started a company do i do wish and i hope more women take the leap earlier yeah me too we need more women founders for sure and i've definitely over the last five years seen more and more i think i think it's starting to be a thing just like there's more women college graduates now i think in the future maybe five ten years from now there'll be more women founders hopefully i really hope so i was just in the yc batch as you know and i think it's about five percent in yc so it was very small and in terms of all female teams both founders were three founders are women it seemed to be in the whole batch of uh over 100 teams maybe just two or three maybe three yeah yeah that sounds right because i've backed over 100 yc teams at this point and i think only one or two of them are all women founders it's very very rare it's so rare and thank you for backing us we're proud to be one of those yeah and we i think we also talked about kind of the skew of age in yc too because you know as an mba a little older i think the average age in yc i don't know if you have a stat for that in the last batch that you're in but it feels like it's like 25 now like 23 is the average age or something this is pretty young i i don't know if i've seen a stat but that's what my gut tells me yeah interacting with everybody that's my gut i mean i backed a 17 year old that dropped out of high school that's that's an i mean that 17 year old is incredible by the way like some of the smartest founders were are super young so i have nothing but respect for someone that was able to do is able to do it that young i will say that i don't know if i was ready at 17 or even 21. i was still like grinding towards wall street in my early 20s i'm gonna be rich and successful in wall street and then i got there and i was like i hate this and i was like oh what do i like i don't know i don't even know who i am and i didn't figure it out until i was 40. just trying things trying things trying things you know but um but it's amazing that you tried so many things and you got there a lot of people never get there right it makes me a great investor because i can kind of look at every all this all this all these things and i've like done every role and like in a lot of different industries so i'm kind of a generalist like a super generalist but it makes me kind of unemployable too you know well then you just have to make your own job don't you that's it yeah that's that's team ignite yep what do you think if you're greatest regret in your career oh while you're turning around i'm on the podcast now i think my gr my greatest regret is chasing success and money too early and not like trying to figure out what i really like right and so when i got to wall street i told this story a hundred times on this podcast but so any regular listeners are rolling their eyes right now but when i got to wall street you know 25 26 worked really hard to get there and i'm like making good money and i'm like i hate my life and i don't want to do this yeah and so i was like okay well if i had you know what do i want to do i have no idea okay if i had 10 or 20 million in the bank and never had to work again what would i work on yeah and that was like existential crisis you know like i was like whoa i have no idea who i am yeah because if i was retired and i won the lottery tomorrow i had no idea what i do i travel of course i'd play guitar and i have my hobbies and stuff and play video games whatever read books But like, what would I build and what would I create? Yeah. And I couldn't figure it out, but it kind of guided me through this like long 15 year journey of iterating on lots of different things, living lots of places. I lived in Japan, I backtracked through Japan and China and I lived in Hawaii and lived in the Caribbean and, you know, I did like a hundred odd jobs, tried a lot of things, you know, had a small business and, you know, I worked in a variety of roles in a variety of industries, but it was never the thing that. i would do tomorrow i wouldn't go to work tomorrow if i had 10 or 20 million in the bank that really bothered me but it led me through this process of like career self-discovery and my wife would always say she'd be like stop trying to get so much fulfillment out of work i'm like well like i think it's really important you know i'm going to do work you know a lot 2 000 hours plus 2500 hours a year like i really want to want to go to work I, you know, I got into product and that was pretty good. You know, I liked building product. I built a lot of ad tech, more tech, sales tech. I powered cool big data system stuff. You know, I led AI at Amazon, the whole deal. And that was fun. Got the MBA along the way because I was, you know, kind of climbing the ranks in product and stuff. But it was never what I'd go do tomorrow if I had won the lottery or something. Right. So, but it wasn't until like I started helping founders at Microsoft scale in Microsoft. I was like, I'm having a lot of fun helping founders. So I started investing and I was like, oh yeah, like I can help them and I can invest in them and help them. This is cool. Oh, I would do this. I'd do this if I had a hundred million. I'd do this if I had a billion dollars. And it took me until I was 40, you know, 15 years of iterating and self-discovery. And so like, I always tell young people like, hey, I want to, you know, do this. I want to do that. I'm like, great. Imagine I'm your rich uncle and I leave you $10 million. You know, like, what are you doing? Like, what are you building? What are you doing? well i'll go travel great great so you just like traveled around you saw like 50 countries and now you're back home what are you doing what are you building what are you creating well like i don't know i'm like great that that's where you start yeah i love that thought experiment and i also love that you you fast forward them past the travel stage because of course everyone that's like the top response everyone i spent half of my 20s traveling like half of my 20s maybe maybe 30 or 40 percent of my 20s unemployed traveling backpacking in europe backpacking in china like Like living around the world. You know, see people on the road that have been on the road for a long time and you're like, I don't want to end up like them either. Yeah. Like literally on the road for two or three years. I think the longest I've been on the road is like six to eight months at a time. That's a lot. Yeah, it's a lot. Like you're just living out of your backpack and seeing stuff and doing stuff and hanging out with people. But you want to kind of return home and have a home base, make friends, build a community like Royal Roots helps and create and build something, right? yeah you can build something that has roots right like that you can go to and build another layer each day i totally identify with that but i love that you you had that process of discovering your own what you wanted yourself it was so painful it was so painful people don't like understand the self-doubt and the like i wasn't depressed but i saw a therapist at one point too but i was just like i see a therapist i'm like i'm kind of depressed and really what it came down to is like i don't want to do this job i'm doing yeah But I don't know what I want to do. And it was like, so I saw a career coach for a while. And that helped a little bit. That helped me get into a different career track. But it still wasn't what I wanted to do if I had 10 million in the bank. It was just like an insidious thought. It's like Inception, the movie Inception, if you've seen that. If somebody went down into the third layer of my dream state, my sub-psyche, subconsciousness, and like implanted this like, but would you do that tomorrow if you had 10 million in the bank? Yeah. So. anyway but now i do what i would do like i'm doing this i would do it if i had a bit if i was a billionaire i'd still be doing this podcast i still would have invested in your company i'd still go to yc demo days so it's cool that makes me so happy to hear you're an actualized human being i'm a fully actualized at least on the career front you know i'm still working on you know i'm not perfect but at least on the career front i feel like okay i'm doing my life's work here like this is what i'm meant to do you know i really feel like that anyway dire try it's a good one and i really love that thought experiment like what would you do if you had all the money you could ever need in your real life i i agree with you i would be doing exactly what i'm doing right now too and i'd be working that's what i look for in founders but this is actually the my little secret sauce you know if anybody any lps are listening this is how i like find founders it's not it's like it's my lived experience seeing your lived experience you know what i mean it's yeah it's the traction and all that stuff but it's it's really kind of figuring out like why are you doing this and you're trying to find out basically a founder who like can't do anything else that's how i feel i can't do it yeah that's basically it's like that's the little secret of like assessing founders is like why are you doing this and like is there anything else you could be doing that you're better suited to do or is this the best thing for you to do right now and the only thing that you want to do right now and there's no plan b yeah that's how that's a big part of how i figure figure out investing and how i've been so successful at it like the metrics show that i think for for my first two funds but it's like it's like my little secret sauce of like why i'm a good gp you know i'd love that and i'm honored you invested in us now because i just i feel like well we better be really successful you're good at picking i don't always get it right but i think if you find mission-driven founders like you that are doing it for the right reasons yeah all the other things kind of take care of themselves right yeah Definitely. Well, I'll give you one personal story that I think I wouldn't be able to overcome if I wasn't so passionate about this problem space. When I first started Real Roots, it was pre-AI. And I realized early on that an app, a mobile app that matched people was just not going to do the trick. So many apps already like that existed. None of them worked. And I didn't see myself designing any novel feature set that was better then. I just didn't think that it was possible. A lot of different iterations have been tried already. So I knew that to really solve this problem, you have to own the space where friendships are actually developing. And that's in real life. Because friendships are falling apart, not through the matching, they're falling apart in the in real life space. So you have to own that space. But when I would tell VCs on campus at Stanford and also professors and classmates that I was going to build an in real life social experience platform, everybody told me, don't do it. That's never going to scale. It's a bad idea. It's never going to scale. So that was the number one piece of feedback. And it was universal. Everyone said that. But then I thought, well, if I need to solve this, I do need to solve this problem. And it's the only thing that works. So I'm going to have to make a bet on myself that I can develop software. that can make in real life streamlined it to such an extent that it could scale and i was just very lucky that ai came around when it did when i've been already building in the space and it's been able to turbo charge us amazing yeah see the conversation really gets going at about 45 minutes that's why we schedule it for 90 minutes a few more questions so what metrics do you watch like a hawk every week well i i watch revenue very closely and this is why we design our product to be very aligned. Our business outcomes are very aligned with user outcomes. So you pay $25, which is a small amount comparative to the rest of the series to get matched. So we have to do a really good job with matching or else you won't join the full experience. And then the full experience is 290. And then we have to do such a good job with that full experience in terms of planning and coordination and curation that you're excited to do it again. or to buy just the planning component. So every step of the funnel, a user only advances through each step of the funnel if you do a really good job in the last step of the funnel. So as a result, I watch revenue. Yeah, so it's revenue, but it's also conversion from the stages, right? So from like, hey, I'm interested to I, you know, did the 25 to like, I did the events and then I converted to like an ongoing. True. What's the biggest decision you have to make in the next six months, and how are you thinking about it? That's a good question. Well, we have a couple of really big challenges ahead of us. One is our retention product that clicks on after the six-week program. We have individual features that seem to be resonating, but putting it together into a collective whole and developing new features that also provide a lot of value is ambiguous. That's an unknown problem. an unknown well known problem the solution is unknown and another unknown problem with an unknown solution is how are we going to continue to grow through other acquisition channels that we're not currently aware of so uh those are the two biggest challenges ahead of us if i had to rank them retention summer one and then figuring out new ways to grow is number two yeah well this has been an awesome conversation i really enjoyed it i got to talk about myself too so yeah thanks for sharing for the women listening where can they find you online and find out how to join the network yeah we're in the app store in in google play as as real roots and on web we are at therealroots.com all right thanks so much dorothy thank you brian thanks for having me

Dorothy Li is the co-founder and CEO of The Real Roots, a startup designing IRL, guided, matched experiences to help adult women build real friendships. With years in mission-driven startups—and a founder’s obsession with “what actually works in real life”—she’s tackling loneliness as a solvable systems problem, not a personal failing. 

With a clear read on why loneliness got louder after the pandemic—and why it suddenly became socially “okay” to admit it—Dorothy offers insights into modern community-building, the science (and art) of compatibility, and how AI can scale nuance without turning humans into spreadsheets. 

In this episode, she discusses why “friendship products” fail when they stop at matching, how Real Roots engineers the conditions for closeness (compatibility + repeated contact + facilitated depth), and what she learned by concierge-running the first groups herself—before tech (and later, voice AI) made the model scale.

In Today’s Episode We Discuss:
00:01 Why Adult Friendship Feels So Hard
01:42 Dorothy Li’s Path to Building The Real Roots
04:12 Loneliness Isn’t New—It’s Just Finally Admitted
06:38 Why Friendship Was Never Properly “Designed”
08:55 The Failure of Matching-Only Friendship Products
11:06 What Actually Creates Closeness Between Strangers
13:18 What You Can’t Self-Report (But Matters Most)
15:34 Early Proof: When Friendships Really Stick
18:06 Men vs Women: Different Paths to Bonding
20:11 Inside The Real Roots Experience
22:57 Why Facilitation Changes Everything
25:04 Designing for Repetition, Not One-Offs
27:09 Scaling IRL Without Killing the Magic
29:41 Building a City-by-City Marketplace
32:08 What Growth Actually Looks Like Early On
35:02 The Awkward Phase Everyone Wants to Skip
37:40 The Founder Trap: Waiting Until You’re ‘Ready’
41:12 How AI Finally Made This Scalable
44:10 The Metrics That Actually Matter
47:36 What’s Next for The Real Roots

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