Andy Dunn on building Pi, a social app to fix the loneliness epidemic, after his bipolar diagnosis and Bonobos exit

Speaker 2: to Yeah. To end the week. Thank you so much for taking the time to come chat with us. Congrats on the Yeah. Congrats to the whole team on the milestone and Yeah. Hope to have you back on soon. We'll talk to you soon. Surprise. Thank you so much. Nice meeting you guys. Thanks having me. Nice meeting you. Have a We'll good talk to you soon. Without further ado, we have Andy Dunn. He's the founder of Pi, Bonobos. He's the author of Burn Rate, and he's here with us on the TV finale drum. Andy, how are you doing?

Speaker 1: I'm doing amazing. Happy Friday, guys. Look at that. Look at that cardigan.

Speaker 4: What is what is what how deep is that? Some of you peeing green, man. That's fantastic. You're blended in I mean, not quite, but, like, pretty close. Yeah. You're blended perfectly into the Chiron. It's fantastic.

Speaker 2: Should we start with the new app? I I wanna go back and hear so many war stories. I've I've followed your career throughout my entire like the last fifteen years. I were texting yesterday. Let's

Speaker 1: kick it off. Hi. Is there's the app of the day. Let's start there. Yeah, what piece Maybe give us the brief history of PIE Yeah. How you got to be the app of the day, and then we can go from there. Yeah.

Speaker 4: Look, this one's pretty simple. I was talking to my psychiatrist one day, and I told him I was feeling a little bit low. I have a proclivity to depression. I've gone through some ups and downs. Got to write a book about that. Yeah. And we talk about a lot of things. At some point, said to me, when's the last time you had dinner with a friend? And I thought about it. This was 2021. We were obviously in the middle of a pandemic and a lot. Yeah. My wife and I and our young son had just moved from New York to Chicago, and, yeah, I think Jordy knows this. My whole world was in Chicago during the Bonobos days. My friends were there. That's where I met my wife. That's where all the Bonobos team was. And I thought when I came back to Chicago, you know what, this is going be great. This is my hometown. My parents are here, my sister who I have a business with, Monica and Andy. This is like a homecoming. And then I realized after a minute, like, I don't have any friends. It's a hard thing to admit to yourself, but I have friends, just none of them live here, right? Yeah. So then I got curious, because all of a sudden I was like, wait, how do you make friends if you don't want to make lame friends and you don't want feel lame? Yeah. Like, do you put yourself out there, and how we solve that problem for people? And that was the beginning of the pie journey.

Speaker 1: Yeah. And then take us up to the present.

Speaker 4: Yeah, so so what it is is is for friends. It's an app Well, it's evolved. It's an app and an AI agent to build infrastructure for your whole social life. Mhmm. So we want to be the operating system by which you get off your phones and back into real life. Mhmm. So the primary product is an app that has got events that we think you might want to go to, communities that you might want to belong to, and then people that we think you'd want to meet, and that's how it gets going. And then what happens, and maybe you guys are in a place in your lives here where at some point you actually have a lot of friends, you have a good social life, but what sucks is it's hard to find time to see them. It's hard to get out of this rat race to actually prioritize seeing the people that you care about, and so that's where we just launched an AI agent called Penelope, and her job is both in iMessage as well as soon in the app to help be a, what we call, social life instigator

Speaker 2: Yep. You know, and chaos coordinator to get you together with the people that you should be spending more time with. So we yeah. What's the actual, like, onboarding workflow? We see a lot of people set up Mac minis just to do stuff with iMessage. I imagine that you're handling all of that on on your end and and then, you know, do I start by downloading the app or can I text something? Like, what what's the workflow to actually start getting prompted to do something in my social life?

Speaker 4: So there's two ways to do it. The easiest way is to just go on the App Store or Play Store and download the Pie app Yeah. And then we can kind of get you going. That's live in Chicago, Austin, San Francisco. We're going live in New York and LA. We got other smaller markets percolating like Columbus and Milwaukee and Atlanta. That's kind of the core way to do it. The second thing you can do is just dig into the community on Instagram pie. What we're doing now is we're building pinelope.com. So that's pienelope.com. Yeah. And that enables you to go right into an agentic experience where you don't even have to get the app. Yeah. Because there is this tension between, well, we want to build an app that solves a problem, but also no one wants to download another effing app. Yeah. So we wanted to create an easier on ramp for people that want to just have the experience in iMessage, and it's like a super cool Wild West world right now with how do you manage that and do that the right way from an infrastructure and a compliance perspective. Sure. How do you how do you know if if the app is working in a specific market? What are what are the indicators?

Speaker 1: What are you what are, you know, what do you see in the data that says, like, hey. Okay. We have we have some product market fit in a place like, you know, Chicago or Austin or or the other cities that you've listed?

Speaker 4: Yeah. So I mean, you guys know the cold start problem, extremely difficult. Jordy, I know you've played in consumer, John as well. Our cold start problem solution is called the Pi Creator Club. It's at picreatorclub.com, and what we try to do is attract and incentivize people who love to bring other people together. Right? We like to say we're hunting for gatherers. These are the community hosts, the community builders who host run clubs and book clubs and NBA watch parties and trivia nights who get folks out there, and we wanna incentivize them. Those are our Airbnb super hosts. Those are our Uber drivers. Those are our Wikipedia article writers. Sure. And we can pay those folks up to $3,500 a month via a rewards program Mhmm. To light up plans and events on Pi, and then they typically distribute those plans through their social media followings. We've got about 800 of those community builders on our app right now, and in any given market, once we have 50, it starts to percolate. Yeah. How how important is going

Speaker 2: individual market by individual market? Because I I feel like one of the unique unlocks of AI is that you can probably go and scrape a bunch of data together, transform it, and do a lot of the grunt work a lot faster. But at the same time, like, actually getting to real critical mass and and putting extra care into it and attention into a launch is probably also very important.

Speaker 4: Totally. One of the tabs we just launched on the app is called the people to meet tab. It's right in the middle, and what it enables you to do is kind of flick through and see who's out there, and go into their profiles, and have it not just be about how they look, but about what are they into, what are their interests, what kinds of events have they gone to, which kinds of events are they going to. And then you can actually star people right on the app, and we hope to build a matching experience that is the first of its kind where it's across friendship, platonic, romantic, and group. And get those people to not have to figure out a plan to get together, but actually just join an event on the product. Back to your question, we think you need about a thousand people on that people tab, about 50 events on the events tab, and that's when we start to see percolation in social density and geographic density start to get momentum.

Speaker 1: How big is the team today?

Speaker 4: It's funny you asked that. At one point, the team was 23, and the age of AI is now 12, and we've seen what you guys are talking about, which is just a massive collapse of product design, engineering, and even go to market where people can do so much more. And so, you know, we didn't have a big moment. You know, we're not Block, we're not Jack Dorsey saying, you know, we're doing some big restructuring, but as you guys know, with startups, things evolve, the team turns over, some people go to do other things. We've got this thing in Chicago we call the PyPal Mafia, where I'll back people that start companies. We're trying to build the tech company Chicago deserves. We've never had a $100,000,000,000 enterprise value tech company built here in Chicago, and you need one of those, as you guys know, to change the market. So we're we're just so we're having so much fun right now because we've gotten leaner and we're moving more quickly.

Speaker 2: Yeah. What what what is the shape of the Chicago tech market broadly?

Speaker 4: It's bad. It's bad. It's really bad, guys. It's the problem in Chicago is two things. Might be the first person to call in

Speaker 2: from Chicago. It is rare, but it's such an interesting I I've lived there. It's a beautiful city. It's amazing. It's a beautiful city. Near Chicago, North Northwestern. Like, there's good schools. I'm sure that a lot of big tech companies have offices there. So there's a pipeline of established talent. Like, it has a lot of the trappings of it could be, you know, pretty quickly out in Austin or Miami or, any of these other LA, like these tiers, but it feels like it hasn't had its like, maybe it just hasn't been marketed, but it sounds like there's also just a lot less going on there.

Speaker 4: I mean, we have some cool things happening. Right? SpotHero was just acquired by Uber. Sure. It's a quantum computing center here. We have Tempest that just went public. Tigus that just had a great outcome. Oh, yeah. Tigus. But the market in general sucks, and I'll tell you why. There's a cultural factor set of factors, and then there's an ecosystem set of factors. Yeah. And they're both navigable, by the way. That's why I'm here. That's why I'm building Pi here. My wife is building Simon hardware company called Kadea Monica Nandy, which I mentioned, because we want to help be the change that we're looking for. The problem in the ecosystem here is twofold. There's no angels. There's no community of people throwing around $10.25, $5,100,000 checks. I mean, there's a few. Yeah. Like, there's, you know, we've got some Mike Gambeson type people here. There's some folks who do it, but it's very hard to get that first 250,000

Speaker 1: to a million. Yeah. And the angels are so influential because, you know, if if a great founder meets an angel on the West Coast or the East Coast, and they're gonna say like, hey, you seem smart. I love your idea, but you're you're absolutely, I'd love to invest, but I think you're kinda crazy to not move to SF or move to New York or etcetera. So that that there's there's definitely a lock in. There's like a talent talent drain that goes coastal. The second thing is the venture capital ecosystem here

Speaker 4: puts most of its money in coastal companies. So I heard something recently. It's a woman named Desiree Vargas Ridley who backs her funds. She's doing cool things, and she has a fund of funds. 90% of the alpha for Chicago based venture firms is created on the coasts. Yeah. Right? And 90% of the capital that the leading Chicago companies raise is from the coasts. Yeah. So when I was raising the pie series a, look, we didn't have the best metrics. Yeah. Maybe we didn't even deserve a series a yet, right? But we were inspired by what we could do. We had a little bit of a kernel of momentum. We had an amazing team. You know, there's just enough talent density here that that's not the issue. You know, we recruited a great VP engineering, Hunter Hussar, who's from Grindr. We've got an awesome, you know, kind of VP ops finance strategy. She's from WinTrust, Bailey Moore. We've got the talent here, but it's very hard to get funded. So I did 15 pitches in Chicago, because I wanted to raise our series a from a Chicago venture fund. Mhmm. I got 15 no's. I did one pitch on the West Coast with Kirsten Green from 4Runner, and we got a term sheet within forty eight hours. So that just illustrates that, you know, some of the challenges with Chicago. And I we believe at Pi, we can be part of the solution because you gotta build a $100,000,000,000 or at least a $50,000,000,000 company to create that ecosystem of angels and to create a training ground for the entrepreneurs of, you know, the next decade in Chicago. Yeah. What's the biggest lesson you're carrying from bonobos over to Pi? I mean, the main one is it just doesn't matter that much. You know? And I I don't know exactly how to describe that to you guys in a way that would make sense because obviously we're so passionate about what we do. Yeah. But having gone through the experience of, you know, being hospitalized in the psych ward at Bellevue, you know, when we were nine years into building bonobos, the cliff notes on my story were we had over a 100,000,000 of revenue, we had 600 plus employees, and I ended up in the psych ward of Bellevue because I had untreated and un medicated bipolar type one. And it felt like the whole world was falling apart. You know, I was losing my sanity. I might lose my job. I might lose the woman that, you know, the first great relationship that I'd ever been in in my life, now my wife, Manuel Sorenstein, and I came out finally ready to deal with it, thanks to the amazing work that they do at that hospital, and rather than walking into the loving arms of my family, I walked into four NYPD officers who booked me and charged me with felony and misdemeanor assault. And then I spent the next, you know, twelve hours in jail, and I remember thinking when I was in jail, because at this point I was now sane, I was medicated, I was ready to deal with this issue, None of this stuff matters that we think matters relative to our health, our freedom, and our liberties. And so I have that perspective now that I care so much about this, and I know my health, and your health, and family, and friends, and loved ones matter so much more than building startups. Yeah. It's an inspiring message. What what have you actually

Speaker 2: done? Who have you met through Pi?

Speaker 4: I've met some amazing people. One of the one of the relationships I'm the most excited about right now is with a woman named Nadia Okamoto. She just joined us as one of our creators. She's got a run club out of New York called Sumies. Yeah. Previously, was she's been a part of a company called August that she was co founder of, a period care company. Cool. And I just she got over 4,000,000 followers on TikTok, million, million on Instagram. What I love seeing is right now is people who are massive content creators and social media influencers pointing all of their following at in person community. Yep. Because the only way to get off these phones is through our phones. The people that were influential in hooking us on social media are very well positioned to say, guys, let's get out. Let's go for a run on Saturday morning for five miles or eight miles. We're gonna go slow. We're gonna talk. So I'm so inspired by our creators. We love we love seeing the spirit around the country. It's it's a huge movement largely driven by Gen Z Mhmm. To to who have realized that it is the damn phones. Yeah. Do you think do you think the

Speaker 1: like, do you think you have a a kind of a window here because, you know, maybe some of the digital platforms would rather we not meet up in person? They're like, actually, it'd be great if Saturday you just, you know, take that six hours, you're gonna go to the Run Club and go to this other thing and you should just doom scroll. Seriously, it'll be good it'll be good for you. And I I feel like that kind of creates creates an opportunity where, you know, a new platform can can emerge that that is not, you know, trying to deliver as many ad impressions as as physically possible.

Speaker 4: Totally. I was just reading this story last night in the New Yorker about the lawsuit that was with you know, that came up. I think someone won 6,000,000 in damages from having been to social media. You guys have probably talked about it. Yeah. Look, I think there's room for the next great American rooted social network right now, and I believe three things about it. Number one, it's gonna be AI native. Number two, it's gonna be focused on actual friends Mhmm. And your IRL local life, your in real life existence. Mhmm. And then thirdly, that that company is gonna be called Pi. I love it.