Here’s a quietly brutal truth: most adults don’t lose friends because they’re bad at friendship. They lose them because the system breaks.
You move cities. Jobs eat time. Relationships reorder priorities. Suddenly the scaffolding that once handed you friends for free—school, dorms, shared chaos—disappears. And in its place? A vague instruction manual that says: “Put yourself out there.”
Dorothy Li looked at that advice and did what founders do best: she called bullshit and designed a system.
She’s the co-founder and CEO of The Real Roots, a company building guided, matched, real-world experiences that help adult women form actual friendships. Not “let’s grab coffee sometime” friendships. Real ones. The kind that turn into bridesmaids, group chats, and people who show up when life gets messy.
This blog is for anyone who won’t listen to the episode but still wants the insight.
Loneliness Isn’t a Personal Failure. It’s a Design Flaw.
Loneliness feels private, almost shameful. Like you missed a class everyone else attended.
But zoom out and a pattern appears.
Adults today move more. Marry later. Work longer. Live farther from family. The pandemic didn’t create loneliness—it just ripped the social mask off and made it socially acceptable to say, “Yeah, I’m lonely.”
Dorothy’s key reframing: loneliness isn’t a character flaw; it’s a coordination problem.
Humans still want connection. The environment just stopped supporting it.
So instead of asking, “Why can’t people make friends?” she asked a better question:
What conditions reliably create closeness—and how do you engineer them on purpose?
Why Most “Friendship Products” Don’t Work
The internet has tried to solve adult friendship. Repeatedly. And mostly failed.
Why?
Because most products stop at matching.
They pair people based on interests, age, or location and then… shrug. Good luck. May the extroverts win.
But decades of social science point to three ingredients that actually matter:
Compatibility (values, energy, communication style)
Repeated contact (you need more than one hang)
Facilitated depth (someone nudges the conversation past weather and work)
Miss one, and the friendship stalls.
The Real Roots doesn’t.
Instead of saying “you two should meet,” it creates small, guided groups that meet multiple times, with structured prompts and a live guide whose job is to pull people gently—but firmly—past small talk.
Think less “networking mixer,” more “permission to be human.”
The Unsexy Secret: It Started Concierge-Only
Before AI. Before scale. Before decks.
Dorothy personally ran the early groups. She matched people manually. Facilitated conversations herself. Watched what landed and what flopped in real time.
This matters.
Because a lot of social products fail by assuming humans behave like clean data. They don’t. They’re weird, guarded, inconsistent, and deeply pattern-driven.
Only after seeing the patterns up close did Dorothy bring in technology—eventually using voice AI to capture nuance that surveys miss: tone, self-awareness, emotional openness, conversational style.
Not to replace humans. To protect the magic while scaling it.
A Subtle but Important Gender Insight
One of the more interesting observations from The Real Roots experience:
Women tend to bond depth-first (conversation → activity)
Men tend to bond activity-first (activity → conversation)
Neither is better. They’re just different.
So designing for women’s friendship meant designing spaces where emotional safety and depth happen early, not accidentally later.
This isn’t therapy. It’s just… permission.
Permission to skip the performance and get to the part everyone actually wants.
Why “IRL Doesn’t Scale” Is the Wrong Take
Investors love to say real-world experiences don’t scale.
Dorothy’s response is quietly radical: badly designed IRL doesn’t scale. Well-designed IRL does.
The Real Roots scales city by city as a three-sided marketplace:
Members
Guides
Venues
Technology handles matching and logistics. Humans handle presence and nuance. Each does what they’re best at.
The result isn’t virality. It’s retention. The rare kind driven by real outcomes, not dopamine loops.
The Founder Lesson Beneath the Product
Underneath the friendship thesis sits a founder truth many people—especially women—will recognize.
Dorothy talks openly about how many women wait until they feel “extra ready” to start. More credentials. More certainty. More permission.
Her lived lesson: readiness is usually a mirage.
The real work begins when you leap slightly before you’re comfortable—and build clarity through contact with reality.
Much like friendship, actually.
The Big Idea to Take With You
If you remember one thing, let it be this:
Connection doesn’t happen by accident anymore. It has to be designed.
Not in a creepy, optimized way. In a human one.
With intention.
With structure.
With someone brave enough to say, “Hey—go a little deeper.”
That’s what The Real Roots is really selling. Not friendship as a feature, but belonging as an experience.
And in a world optimized for speed, that might be the most contrarian product of all.
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Chapters:
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
Transcript
Brian Bell (00:01:34): 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.
Dorothy Li (00:01:52): Thank you. Thank you for having me. I’m excited.
Brian Bell (00:01:54): Yeah. So I’d love to get your background. What’s your origin story?
Dorothy Li (00:01:57): Well, my background from the very beginning is my parents were both entrepreneurs. 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, eAcademy, 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 matured and just spent 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 this solution for myself foremost and all the women like me.
Brian Bell (00:03:23): That’s amazing. And we met BYC, obviously we were an investor and 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?
Dorothy Li (00:04:14): Yeah, I mean, you raised a really good point. Loneliness has been a growing epidemic for the last 20, 30, maybe even 50 years, as illustrated by books like Bullying Alone. And that, I believe, 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 friends are your family. So those two trends are only getting worse. But what changed 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. It 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 shared 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.
Brian Bell (00:05:57):
Yeah. I have this problem myself. You know, my personal lived experience is I moved out of the Bay Area during COVID.
Dorothy Li (00:06:03):
Yeah.
Brian Bell (00:06:04):
So I entered this new area and I’m basically just living in my house. you know, with my family for a year before COVID 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 basketball, you know, pick up and league basketball, you know, two or three times a week. And then recently I started, you know, cause 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 how’s it going 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 was fun, you know, you 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. And, but maybe you could talk a little bit about, okay, so we know the problem, right? 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?
Dorothy Li (00:07:15):
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, like, 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.
Brian Bell (00:08:21):
Wow. So you got like this voice AI kind of onboarding flow.
Dorothy Li (00:08:24):
Yeah, yeah.
Brian Bell (00:08:26):
I think I told you my wife actually has a voice AI startup. You guys should probably talk about this.
Dorothy Li (00:08:30):
Yeah, I would love to.
Brian Bell (00:08:32):
It’s called a little plug, your360.ai, so you can look that up.
Dorothy Li (00:08:34):
Amazing.
Dorothy Li (00:08:35):
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 like 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 um in a personality that previously was only able to be done by a human in the very beginning of railroads i 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.
Brian Bell (00:09:39):
That’s important. It’s an important thread to tug on. Something that VCs care a lot about is like the why now.
Dorothy Li (00:09:44):
Yeah.
Brian Bell (00:09:45):
Before you’d have to do these like SurveyMonkey 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.
Dorothy Li (00:09:58):
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 their social wellbeing. 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 have been a very different price point than what we’re seeing today.
Brian Bell (00:10:40):
Yeah, that’s interesting. So how does your matching algorithm and process look at a high level? Like what’s some insights or surprises that the audience might be surprised to learn about?
Dorothy Li (00:10:50):
Yeah. Well, I think what’s really interesting for me is like when I first started working on Real Roots, I thought that there is 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 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 or 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 can be a little bit more generous with mismatches in other parts of my life or other parts of the personality.
Brian Bell (00:12:25):
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, I put them 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.
Dorothy Li (00:12:41):
That’s amazing. I love that.
Brian Bell (00:12:43):
Versus like the Silicon Valley, like everybody works in tech and it’s very rare you meet somebody who doesn’t.
Dorothy Li (00:12:47):
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 another thing that we do in Real Roots is 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, 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.
Brian Bell (00:13:39):
But there’s kind of the explicit what I think I want. And then there’s like the implicit.
Dorothy Li (00:13:44):
Yeah.
Brian Bell (00:13:44):
What you can kind of discern from maybe some stories in the background or like, hey, tell me a story about your your best friend or tell me a story about a friend that you wish you had in your life right now or, you know.
Dorothy Li (00:13:56):
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, it’s 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 mashing, 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.
Brian Bell (00:15:40):
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 the top of your head?
Dorothy Li (00:15:48):
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.
Brian Bell (00:16:00):
Yeah, 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.
Dorothy Li (00:16:07):
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 was mostly 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 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.
Brian Bell (00:16:38):
Yeah, that’s funny you mention that because 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 these other husbands and other dads, right? And the dads are dads of your kids, you know, kids’ friends or the husbands of your wife’s friends. And that’s literally how like middle-aged men make friends.
Dorothy Li (00:17:00):
Yeah.
Brian Bell (00:17:01):
Like you like beer? Yeah, I like beer. Okay, cool. You like basketball? No, I like football. Okay, I like football. And like, that’s it, you know?
Dorothy Li (00:17:07):
So easygoing.
Brian Bell (00:17:09):
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?
Dorothy Li (00:17:20):
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 in a way. Like they identify traits that they want to be around more and traits that they are pushed against and they want to distance themselves from a little bit more.
Brian Bell (00:17:41):
That’s why the matching is so important for women. 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 you know I didn’t realize it before, but you’re out. Yeah. 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?
Dorothy Li (00:18:23):
Yeah. Yeah. Yeah. Totally. I can’t imagine.
Brian Bell (00:18:25):
And then you end up with these friends as guys. And I have friends like this where you’re like, I 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?
Dorothy Li (00:18:36):
Yeah, you have a ton of shared context, right? That makes a lot of sense.
Dorothy Li (00:18:40):
Well, men and women statistically do bond differently. Of course, we have to be aware that there are individuals inside of each spectrum that 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 design Real Roots for Women first.
Brian Bell (00:19:10):
Yeah. So what happens next? So, you know, the ladies on board and in the area, what’s the next step in the process?
Dorothy Li (00:19:15):
Yeah. So ladies on board, they 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.
Brian Bell (00:19:38):
How many people are there in the group?
Dorothy Li (00:19:40):
About 10.
Brian Bell (00:19:41):
About 10. Okay. So that’s enough to have a couple of side conversations going at once. Yeah.
Dorothy Li (00:19:45):
Actually, you know, 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.
Dorothy Li (00:20:17):
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 uh do i want to get rematched and about 50 right now continue on and then the other
Brian Bell (00:20:31):
half interesting 50 half go you know what i want to do another intro dinner kind of thing and yeah try this again yeah or our matching is getting better over time but yeah that’s what it okay and so half so out of ten five will say hey let’s meet again
Dorothy Li (00:20:45):
Yes, let’s pay for the program, which allows us to have RealBreats coordinate and lead six more meaningful experiences for us.
Brian Bell (00:20:54):
Interesting. So how do you price it for the first meeting versus the six additional meetings?
Dorothy Li (00:20:58):
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.
Brian Bell (00:21:09):
$290. Okay. That’s pretty affordable to make some friends, I think. And then, you know, 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?
Dorothy Li (00:21:23):
That’s a really good question. It’s still 10, maybe 8 to 10 is the 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 It leans out together. That’s how we know that matching is super important because when we get it right, we really get it right.
Brian Bell (00:21:45):
And so the five would maybe do another dinner with five new, something like that.
Dorothy Li (00:21:48):
Yeah.
Brian Bell (00:21:48):
So five have leaned in and said, no, like I’m leaning into this group and five are leaning out. You do another... intro guided session with five new and try to get it up to eight to ten well
Dorothy Li (00:22:00):
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 is compatible but for the most part we see a binary outcome
Brian Bell (00:22:20):
That’s interesting. What have been some of the more interesting correlated traits to leaning in versus leaning out?
Dorothy Li (00:22:26):
Group dynamic. When we get it right, the whole group leans in.
Brian Bell (00:22:29):
Yeah.
Dorothy Li (00:22:30):
It is so fascinating. I almost think it’s a snowball. Once five or six women have leaned in, the rest lean in rapidly.
Brian Bell (00:22:37):
Right. Yeah, it’s kind of that’s kind of interesting social dynamics. And what are the next six sessions look like? What are those?
Dorothy Li (00:22:43):
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 another night might be board games and then And so on and so forth.
Brian Bell (00:23:21):
And it kind of depends on the group because you have all the insights on what they like, what they don’t like.
Dorothy Li (00:23:25):
Yeah, absolutely. And each night we have a different vein of conversation topics. So one night we’ll be talking about friendships, the next one family, the next one career, et cetera. 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.
Brian Bell (00:23:45):
Is it six sessions over six weeks or is it like every other week? Six sessions. So six weeks have gone by and now we’re roughly two months in and then what happens?
Dorothy Li (00:23:54):
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 you 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.
Brian Bell (00:24:56):
Yeah, that was a good problem to have, though. I mean, if you’re getting people through the funnel, and then it’s like, okay, 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?
Dorothy Li (00:25:14):
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 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 a 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.
Brian Bell (00:26:00):
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 every evening doing stuff?
Dorothy Li (00:26:09):
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, hosts, 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.
Brian Bell (00:26:39):
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?
Dorothy Li (00:26:50):
Yeah, that’s a really good question. So we’re super early. We just don’t know yet, but 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.
Brian Bell (00:27:12):
But I would imagine Instagram ads are pretty, pretty, you know, they are definitely effective.
Dorothy Li (00:27:17):
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. Yeah. Keep in mind, we currently only have three people.
Brian Bell (00:27:30):
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?
Dorothy Li (00:27:40):
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 love 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.
Brian Bell (00:28:02):
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?
Dorothy Li (00:28:09):
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, 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 if 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 there at the beginning where it’s really awkward.
Brian Bell (00:28:57):
Yeah, so the lesson is you can go spend 150 grand on an MBA like we did to make some friends.
Dorothy Li (00:29:02):
Or like 250, unfortunately.
Brian Bell (00:29:03):
Or like 300 bucks on Real Roots, you know? So it’s funny if it’s not too far off from the truth.
Dorothy Li (00:29:09):
It really isn’t. I did my initial user interviews were on campus at Stanford. 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.
Brian Bell (00:29:22):
So that was some of those friends are priceless. I mean, I wouldn’t be a VC if I didn’t get my MBA, like because the people I met and the exposure I got and the career acceleration I got and the network I got like led to Team Ignite and what I do now. Like I’m not confident I would be doing exactly what I’m doing right now.
Dorothy Li (00:29:39):
That that’s an amazing thing to hear. You know what? I feel the same way.
Brian Bell (00:29:43):
Yeah. Yeah. I mean, so if you’re thinking, if you’re listening and thinking about getting an MBA, you probably should. Like, just go spend 150, 200 grand, whatever it is now. You won’t regret it. You might, but...
Dorothy Li (00:29:55):
I think if you’re looking for a community that can really accelerate you, 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 would guess you can learn...
Brian Bell (00:30:08):
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, case study breakdowns. You’ll get the gist of it. I think if you want to build a network, it’s pretty unparalleled. It’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?
Dorothy Li (00:30:40):
Yeah. Yeah, definitely.
Brian Bell (00:30:42):
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.
Dorothy Li (00:31:00):
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.
Brian Bell (00:31:21):
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.
Dorothy Li (00:31:41):
Fair. Yeah.
Brian Bell (00:31:42):
It’s fair. It’s kind of true. So if you could go back and do one thing differently, what would it be?
Dorothy Li (00:31:48):
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 are there like i saw this meme the other day where
Brian Bell (00:32:06):
Like 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 20s that I would have not even given the time of day in my 20s. Something like that. It was like some meme like that.
Dorothy Li (00:32:21):
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 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.
Brian Bell (00:33:05):
I’ve known my wife long enough that I went to her 21st birthday. I’ll say that. And we were still just friends at the time. And I’m in my mid-40s. And then so we’ve been together since that age, over 23, 24 years now.
Dorothy Li (00:33:18):
Wow. How long were you friends for before you made them?
Brian Bell (00:33:22):
I wouldn’t call it friendship. I’d call me like chasing her and courting her for like seven months. But yeah, I was in the friend zone for about six months.
Dorothy Li (00:33:29):
not bad i mean it’s it’s really hard to get out of the friend zone so you clearly did it right
Brian Bell (00:33:33):
yeah i could be a pompous cocky asshole 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
Dorothy Li (00:33:56):
Oh, that’s amazing. What about learning? That being yourself is better than being any of it, right?
Brian Bell (00:34:01):
Yeah, that’s the lesson for any guys listening in their 20s. Just be yourself, you know?
Dorothy Li (00:34:06):
Yes.
Brian Bell (00:34:07):
And if being yourself isn’t working, then like she’s not the right girl for you.
Dorothy Li (00:34:11):
No, absolutely. Yeah. The same thing applies for all human relationships.
Brian Bell (00:34:15):
Yes. So let’s get back to business. What would you change? Yeah.
Dorothy Li (00:34:19):
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 roost 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 a startup as an early employee, learned a whole bunch, which was amazing and makes me a much better founder than I am 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
Brian Bell (00:35:13):
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 it’s starting to be a thing. Just like there’s more women college graduates now, I think in the future, maybe five, 10 years from now, there’ll be more women founders. Hopefully.
Dorothy Li (00:35:27):
I really hope so. I was just in the YC batch, as you know, and I think it’s about 5% 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 over 100 teams, maybe just two or three, maybe three.
Brian Bell (00:35:48):
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.
Dorothy Li (00:35:56):
It’s so rare. And thank you for backing us. We’re proud to be one of those.
Brian Bell (00:36:01):
Yeah. And 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.
Dorothy Li (00:36:18):
I don’t know if I’ve seen a stat, but that’s what my gut tells me, interacting with everybody.
Brian Bell (00:36:23):
That’s my gut. I mean, I backed a 17-year-old that dropped out of high school.
Dorothy Li (00:36:27):
I mean, that 17-year-old is incredible, by the way. Some of the smartest founders are super young, so I have nothing but respect for someone that is able to do it that young. I will say that I don’t know if I was ready at 17 or even 21.
Brian Bell (00:36:42):
I was still like grinding towards Wall Street in my early 20s. I’m going to 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...
Dorothy Li (00:36:56):
But it’s amazing that you tried so many things and you got there. A lot of people never get there.
Brian Bell (00:37:00):
Right. It makes me a great investor because I can kind of look at 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?
Dorothy Li (00:37:15):
Well, then you just have to make your own job, don’t you?
Brian Bell (00:37:17):
That’s it. Yeah, that’s Team Ignite.
Dorothy Li (00:37:19):
What do you think is your greatest regret in your career?
Brian Bell (00:37:22):
Oh, while you’re turning around, I’m on the podcast now. I think 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, 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.
Dorothy Li (00:37:49):
Yeah.
Brian Bell (00:37:49):
And so I was like, OK, well, if I had, you know, what do I want to do? I have no idea. OK, if I had 10 or 20 million in the bank and never had to work again, what would I work on?
Dorothy Li (00:37:57):
Yeah.
Brian Bell (00:37:58):
And that was like existential crisis. You know, like I was like, well, I have no idea who I am. Because if I was retired and I won the lottery tomorrow, I had no idea what I’d do. I’d 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? 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 100 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.
Brian Bell (00:38:41):
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.
Brian Bell (00:38:47):
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. Yeah. 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 martech sales tech i powered cool big data system stuff you know i led ai 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 and but it was never what i’d go do tomorrow if i had won the lottery or something, right?
Brian Bell (00:39:28):
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, you know?
Brian Bell (00:39:47):
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? Oh, 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’s where you start.
Dorothy Li (00:40:13):
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,
Brian Bell (00:40:24):
like half of my 20s, maybe, maybe 30 or 40% 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.
Dorothy Li (00:40:59):
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 had that process of discovering your own, what you wanted yourself.
Brian Bell (00:41:13):
It was so painful. It was so painful. People don’t like understand the self-doubt and 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.
Dorothy Li (00:41:28):
Yeah.
Brian Bell (00:41:28):
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?
Brian Bell (00:41:53):
yeah so anyway yeah 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
Dorothy Li (00:42:06):
me so happy to hear you’re an actualized human being
Brian Bell (00:42:09):
I’m 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.
Dorothy Li (00:42:22):
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 whole life? I agree with you. I would be doing exactly what I’m doing right now too.
Brian Bell (00:42:34):
That’s what I look for in founders. But this is actually 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 really kind of figuring out like, why are you doing this? And you’re trying to find basically a founder who like can’t do anything else.
Dorothy Li (00:42:58):
That’s how I feel. I can’t do anything else.
Brian Bell (00:43:00):
That’s basically it. 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.
Brian Bell (00:43:12):
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,
Dorothy Li (00:43:27):
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.
Brian Bell (00:43:35):
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, all the other things kind of take care of themselves, right?
Dorothy Li (00:43:44):
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 had 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.
Dorothy Li (00:44:20):
But when I would tell VCs on campus at Samford 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 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 turbocharge us.
Brian Bell (00:45:10):
Amazing.
Dorothy Li (00:45:11):
Yeah.
Brian Bell (00:45:12):
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?
Dorothy Li (00:45:21):
Well, 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.
Brian Bell (00:46:05):
Yeah, so it’s revenue, but it’s also conversion from the stages, right? So from... 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?
Dorothy Li (00:46:24):
That’s a good question. Well, we have a couple of really big challenges ahead of us. One is our retention products. 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. 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 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.
Brian Bell (00:47:07):
Yeah. Well, this has been an awesome conversation. I really enjoyed it. I got to talk about myself too.
Dorothy Li (00:47:12):
So yeah, thanks for sharing.
Brian Bell (00:47:15):
For the women listening, where can they find you online and find out how to join the network?
Dorothy Li (00:47:20):
Yeah, we’re in the app store in Google Play as Real Roots. And on web, we are at therealroots.com.
Brian Bell (00:47:27):
All right. Thanks so much, Dorothy.
Dorothy Li (00:47:29):
Thank you, Brian. Thanks for having me.
