Latest / Breaking Precedent / The Breakdown: Andy Dunn on Building Bonobos, Battling Bipolar and Baking Pie [Replay]

Transcript

The Breakdown: Andy Dunn on Building Bonobos, Battling Bipolar and Baking Pie [Replay] · Breaking Precedent

• # Revisit [00:00:00] Welcome back to Breaking Precedent. This conversation with Andy Dunn feels even more relevant today than when we first recorded it. Andy is best known for building [00:00:10] Bonobos and helping pioneer direct-to-consumer retail. But what makes this episode special is his willingness to talk openly about the parts of success we don't always [00:00:20] discuss: identity, mental health, and the stories we tell ourselves about who we're supposed to be. In a culture that often celebrates certainty and [00:00:30] perfection, Andy reminds us that vulnerability can be its own form of leadership. His perspective on building companies, navigating bipolar [00:00:40] disorder, and finding meaning beyond achievement has stayed with me long after our conversation ended. Here's my conversation with Andy Dunn. **Andy:** To build [00:00:50] something new, it needs to break precedent. It has to be non consensus. Only time shows whether you're right or wrong. **Leah:** Hi, everyone. I'm Leah Sullivan, and this is Breaking [00:01:00] Precedent, the podcast where we dive deep into the stories of innovators who are pushing societal boundaries, challenging precedents, and setting new ones in their fields. [00:01:10] Today, I am joined by Andy Dunn, founder of Bonobos, author, and a Chicago native whose journey is as remarkable as it is multidimensional. **Andy:** [00:01:20] We struck a deal. He made me the CEO. CEO, even though he got the initial idea going of, uh, better fitting men's pants. The only thing I really brought to the party at that time was, I was excited to go raise [00:01:30] money for it because I wanted to be an entrepreneur. **Leah:** Growing up in a biracial household in suburban Chicago, Andy's experiences navigating identity, humor and belonging shaped [00:01:40] his perspective on embracing differences and breaking norms. **Andy:** I wanted my identity to be another white kid at some point. I wanted to [00:01:50] shun that part of me that was different when I got to college, it was starting to dawn on me that there is actually a lot of power in what makes us different. **Leah:** After building and scaling [00:02:00] Bonobos to a 310 million exit to Walmart, his story does not stop at this entrepreneurial success. Andy also opens up about a deeply [00:02:10] personal and powerful aspect of his journey, his mental health. In his memoir, Burn Rate, Andy candidly shares his experiences living with bipolar disorder and the [00:02:20] challenges of managing mental health while building a groundbreaking company. He offers profound insights into resilience, vulnerability, and the importance of [00:02:30] of destigmatizing conversations about mental health, especially in high pressure environments like entrepreneurship. **Andy:** When I was 20, I was diagnosed with bipolar [00:02:40] one. It's a very hard diagnosis to absorb because if you are data driven as I am, you're like, okay, the most likely I way I'm going to die is to end my own life. We can't accept this. [00:02:50] We have to change it. **Leah:** And now Andy is embarking on a new chapter as the founder of Pi Social, a startup focused on creating meaningful connections and fostering [00:03:00] community in a digital world that often feels isolating. His mission to build a platform rooted in humanity and connection is yet another example. of his [00:03:10] ability to break precedence and redefine what's possible. **Andy:** There are these things that come to us in life that we don't want, that visitor at the door with the bad news, [00:03:20] invite that agent of doom into your home and sit down and have a conversation. You don't know what's bad news or good news in your life until later.[00:03:30] **Leah:** Andy Dunn, thank you so much for joining me here on Breaking Precedent. **Andy:** I'm so excited to be here. Thanks for having me. **Leah:** Yeah, me too. It's been a minute since we've seen [00:03:40] each other. So I'm excited to be able to see you here today, too. Although we're just sending out the audio recording. **Andy:** Totally. No, I've seen you in my inbox, but this is a better way to do it. **Leah:** This is [00:03:50] a better way to do it. So I want to kick us off by asking kind of a high level question, which is, do you think of yourself? [00:04:00] As a precedent breaker. And how does that show up in your life? **Andy:** I don't really think of myself that way. Now I think about myself as. Someone that couldn't [00:04:10] get my son to brush his teeth this morning in a good way. Our identities get wrapped up in the quotidian things of our lives. I remember I'm a big [00:04:20] Chicago sports fan. I live in Chicago. The Cubs were the worst team of all time. Then we won the World Series and the person who led us there, a friend, Theo Epstein is his name, the [00:04:30] general manager of the Cubs. **Leah:** Dude, I am a Sox fan. I know who Theo is. **Andy:** There we go. He did the **Leah:** same thing in Boston. **Andy:** amazing. Broke the curse twice. Yes. A truly [00:04:40] remarkable feat. **Leah:** Yes. And **Andy:** I think it was Fortune or someone called him, the best leader in the world. it was a crazy honor, and they asked him about [00:04:50] that and he said, I can't even get my dog to pee outside And I guess that's how I feel, that whatever the public accolades are, they don't [00:05:00] square with. My own sense of self. **Leah:** Well, let's dive into that. You grew up in Chicago. You and I have something in common, which is [00:05:10] we both grew up in this multicultural household. Paint us a picture. Tell us a little bit about what that was like as a young child. **Andy:** Yeah, it was the same [00:05:20] thing. David Foster Wallace speech at Kenyon College about the two fish who are swimming and then older fish comes by. And the older fish says, how's the [00:05:30] water and then swims away and then the two younger fish turn to each other and one says, what's water, right? And it's this idea that we're not even aware of our context. So in [00:05:40] retrospect, it's clear to me that I was raised in a really stimulating biracial household. But at the time, I had no idea. In fact, my first awareness of it [00:05:50] was I'm in high school, and I had one of those friends who's like a friend, but also sort of a frenemy who's developed a nickname for me that caught on wildfire in high school, which [00:06:00] is Windu for white Hindu, which I came home and I told my parents who are very empathetic people, and they both just died laughing because it's kind of funny in [00:06:10] retrospect. **Leah:** Right. **Andy:** But that was actually the beginning of my awareness of, Oh, I guess I'm different. I guess I have brown skin and a sea of mostly white suburban Chicago classmates. I guess there's something [00:06:20] different. **Leah:** Did he mean it in a vindictive way? Do you think at the time? Or is it just kids? I had a similar experience in high school as well. [00:06:30] And I think in my case. I bet that kid that said it didn't really understand what he was saying. But for you, what was your experience with that? **Andy:** I think a lot of people I [00:06:40] wanted to be the same as others. And so I wanted my identity to be another white kid at school. And I had a [00:06:50] white dad who was like, tall with blue eyes. And so it was weird to be like, well, no, I'm this other thing in the eyes of the community. [00:07:00] And I didn't want that. I wanted to look away from that difference. I wanted to shun that part of me that was different. And then later it was funny. [00:07:10] Like when I got To college at Northwestern, I was in a fraternity again, mostly homogeneous, and one of the guys, Frazier from Tulsa, Oklahoma used to say, if it can be done, [00:07:20] it's Andy done And it was this like, it's pretty catchy, very funny, like Indian accent . And by then it was starting to dawn on me that there is actually a lot of [00:07:30] power in what makes us different. Hmm. But in high school. Like trying to meet girls and trying to fit in and trying to not just be like the king of the [00:07:40] nerds. Yeah, that kind of hurt at the time. I don't think he was vindictive. I think he was just a high school kid, you know, making fun of his friend. I actually think it was like pretty solid, [00:07:50] dope, total nerd, math team, captain of the Scholastic Bull team. Wow. And that part was cool, which is that I did come eventually to embrace that. That [00:08:00] part I was kind of proud of. And then the usual stuff of trying to cross the aisle into the popular and athlete and all that stuff. And none of that worked out for me, but [00:08:10] I'm glad I'm a nerd. I'm happy to be one. **Leah:** Was there a creative part to you as well? Were you ever into fashion in high school? I mean, you went on to found [00:08:20] Bonobos, but were there pieces of you that had this creative aspect as well? **Andy:** Well, it's funny. We have a lot of the Bonobos ethos was around men caring about their fit. [00:08:30] And for some reason, just the other day, I was thinking about this party that I went to and we were down in Chicago on Belmont, which has these cool like shops and [00:08:40] discovering tight fitting clothes. And I had this silver glistening short sleeve muscle tee, which is not a good thing to have if you don't have many [00:08:50] muscles. And I remember being at this party, it was raining out and we were at a friend's house. It was her birthday party. like dancing, it was raining and feeling that early [00:09:00] twinkle of self expression. Maybe that was the early New Yorker in me of feeling I wanted to be different. I [00:09:10] wanted to wear things that were different than other people. I wanted to be a free spirit and I don't think I was particularly fashionable, but I did get a really nice compliment the other day [00:09:20] where a guy I know here in Chicago was like I don't know anybody that dresses like you, but he goes, you just do it different. And actually that gave me a little more permission to get even [00:09:30] weirder. And now my team at my company has to be doing like fit checks on tick tock, **Leah:** but that started in high school. I'd start maybe a glimmer of it at least. I love the **Andy:** [00:09:40] headwaters, right? The headwaters are all there. If we go back and trace where it began. **Leah:** So good. What about. All right. did your parents, their careers, their cultural heritage, how [00:09:50] did that influence your worldview? Did it broaden your worldview? Did you have this global view at all at the time? **Andy:** Yeah, majorly. First of all, [00:10:00] mom is a great leader. She led a team of 20 ultrasound techs for 20 years, had no turnover. She cared so much about them as humans behind the [00:10:10] colleagues that she worked for the phone would be ringing every night that was back in the era of caller ID. And she'd be like, Oh, it's Karen. And then she'd pick up the phone and be like, Karen, how are you? [00:10:20] And then half hour conversation where Karen would be talking about her kids or her whatever. And then we knew all these people in her world because their personal [00:10:30] lives were present in our personal lives, their joys and their struggles and their children and their husbands. It was very present. And in retrospect, it just seemed normal at the [00:10:40] time. It was like my mom talking about her work, but I now in retrospect, realize all the great markings of a leader, holding people to a high standard at work [00:10:50] and doing it by caring about the humans. behind those professionals. So that was mom and she was born in a refugee town on the way from Rawalpindi, [00:11:00] Pakistan to New Delhi, India at the time of the partition. So she was born in the context of She was born **Leah:** on the way. **Andy:** Yeah. 14 million people displaced, one to two million people killed. And she was [00:11:10] born on that journey, multi year trek. And then very differently, my dad's like a white dude from the Midwest, Scandinavian American, with a very global [00:11:20] perspective as a U. S. history teacher. And it was always the questions, then discussions about what was happening in the world. I mean, I just saw my parents live down the, you know. Street and I sat [00:11:30] down on Sunday and my dad and I were watching the Bears game and I was like, so what do you think about Syria? we just like dove into what his thoughts were and he's got such a great grasp of history. And [00:11:40] so those were the conversations that we were having and the normal stuff. You know what I mean? Like it was, Hey mom, can you make Indian food tonight? Right. And that was like a way to be aware of [00:11:50] being different. **Leah:** Yeah. Were there any moments throughout childhood, teenage years that shaped your path to entrepreneurship? Did you know what [00:12:00] being an entrepreneur was when you were growing up? Did you have that model in your mind? **Andy:** Total black sheep. No, I didn't have those role models. I wasn't [00:12:10] aware that that was a path. All my role models being Indian immigrants in the 60s and 70s in my extended family were doctors because that was, that's who got here, doctors and engineers.[00:12:20] My mom didn't get to be one. I think she, I be a great doctor because she had to send money home at a really urgent time when her father was dying. She never got to go back [00:12:30] and see him and really has never made peace with that because she was the daughter who was shipped off, send money home, live with your older sister. Her older sister was an OBGYN actually delivered [00:12:40] me. Which is kind of funny if you have an aunt who's like, I put you in this world, I can take you out of it. **Leah:** Yeah, right. That's power. **Andy:** Delivering your sister's kid, that's just crazy to [00:12:50] me. But that was our family and so I really looked up to all the physicians around me and like classic Indian American kid, I'm going to be a doctor. That was the [00:13:00] track. And then I had. an awakening once I got to college and met all these people whose parents had been entrepreneurs. And I had one in high [00:13:10] school, a friend of mine, his dad owned an auto parts store, five. And I was just fascinated by that. And that was my introduction to [00:13:20] retail, I guess, was Rick's auto parts. **Leah:** What do you think drew you to that particularly? **Andy:** I think it was because they were rich, like [00:13:30] growing up in Chicago in the nineties. It was the Jordan era, and I was obsessed, my dad and I didn't miss a game, but on TV because we couldn't afford to go. Yeah. And actually the [00:13:40] one game that he took me to for Christmas, Jordan scored 42 points, Pippin had 33, Bill Carrey was the player of the game. And there's that moment when you're there and the announcer. You know, [00:13:50] and now at guard, six, six from North Carolina, Michael, like, I still remember. **Leah:** Oh my God. I love it. **Andy:** Maybe the most thrilling moment of my [00:14:00] childhood was that introduction because he was my hero. He was like, God, and my friend's dad had season tickets. And I just remember thinking like, that's [00:14:10] the goal. Season tickets to the bulls. Of course, when I got back to Chicago a couple of years ago, what did I do? I went and bought season tickets to the bulls and now they're so bad. They're so bad, but I've got a [00:14:20] new love in sports, which is the WNBA. And so we've got seats at the Chicago sky. **Leah:** Nice. **Andy:** And watching like Angel and Caitlin. So I guess that's like my updated [00:14:30] realization of that dream is that if you are an entrepreneur, You can have amazing experiences, I guess, and I, I don't know, [00:14:40] somehow that got lodged in my brain from Rick who ran Rick's Auto Parts. **Leah:** Love it. You just never know how these things are going to stick with you and land, right? So you went on to Northwestern. [00:14:50] Did you end up studying business there? You started on this medicine track and then veered away? **Andy:** Yeah, totally. I had the Northwestern version of it, which is [00:15:00] economics. And then I also did a little follow in my dad's footsteps and studied history there. And he has been a history major at Northwestern back in the day. And then a little bit of [00:15:10] Spanish. So Northwestern doesn't have an undergraduate business program. But then in my fraternity, Sigma Chi, that was almost like the business program because most people went into business. [00:15:20] And so that was the beginning of my like, Oh, what's strategy consulting? And then there was a guy in the class who was going to work at Bain, a football player from the team who I really looked up to, who [00:15:30] was in our house. And then I went and interviewed there and I didn't get the job. And I was like, Whoa, that sucked like that for my internship. I want to figure out how to do that. And so that was my first job out of school [00:15:40] was once I got that consulting role and spending a few years doing that. **Leah:** And then you found your way. To Stanford GSB, talk a little bit [00:15:50] about what drew you to that program, how you found it, how you got in there. What was that like? **Andy:** I had this thing I wanted to do when I worked at Bain, [00:16:00] which was, I wanted to buy the rights to a local falafel and hummus restaurant that I thought was amazing called the Pita Inn. And. Literally, still to this day, the [00:16:10] best falafel and hummus I've had outside of the Middle East. And take it national. Cause I was like, we have Chipotle. We have fill in the blank, other fast, casual restaurant [00:16:20] concepts, Panera, but there was none in Middle Eastern food. And now there's, I think seven or 8 billion public market cap company. I think it's called Kava that's [00:16:30] doing that. Wow. So this was the idea for that 20 years ago. And then the son's owner of P to N heard about the deck and was like, who's this guy shopping like a deck about expanding my [00:16:40] restaurant? But my whole thought was like, I need to raise money around this concept and then I can approach the restaurant owners and see if they're open to like franchising or something. I was overconfident. Of [00:16:50] course. I was like, I'll be able to raise some money for this. I couldn't raise a penny for this idea. I couldn't get anyone interested as an angel investor in something entrepreneurial. And [00:17:00] it really bothered me. I felt like there was a lack of a growth mindset in Chicago. There was a lack of like, why would this work? And I was surrounded by first I worked in consulting and then I worked in [00:17:10] private equity, very smart, incredibly some brilliant business people, but who didn't have a mindset of what can we put in the world that isn't here yet. It was more about working with [00:17:20] businesses that were already at scale or already had profits. And then when I went to visit Stanford GSB, it was totally different. I was like, love is in the air. [00:17:30] Startups are in the air. What is possible and that whole ecosystem. And so that was a very nurturing place to be like, okay, it's okay to dream. And it's okay to try to raise money. And in [00:17:40] fact, it's expected. weird now being back 20 years later, building a new startup in Chicago and noticing that we still have those issues here that we're [00:17:50] trying to transcend. There is a tallest poppy syndrome. My wife refers to it as in the Midwest, which is you're not meant to stand out too much from the crowd. Unlike I'd say New York City where I lived building [00:18:00] bonobos for 15 years where it's all about chutzpah, right? Or the Bay Area where it's all about innovation and who's going to build the next huge thing. So that was a really nice [00:18:10] thing, because I felt like I was with my people in terms of let's conspire to build a different future than the present. **Leah:** And that's where you met your co founder, Brian, [00:18:20] who came up with the original idea for Bonobos, which then you came on board full time and helped scale up and take over. Tell us the story about [00:18:30] what originally inspired the idea. **Andy:** So I met Brian Spaley at Stanford GSB. He was actually my housemate the [00:18:40] first year. And the whole time we're going through the business school journey, he's percolating on this idea of making better fitting men's pants. And I was working on these pie in the sky [00:18:50] consumer internet ideas. I had a weird one to build something in the content media space. And meanwhile, Brian's identifying that there is this real customer pain point of [00:19:00] guys wear jeans because they don't like the fit of their pants and guys don't like going shopping. And that became a company. And so at some point I looked at him and I said, wait, can [00:19:10] I team up with you on this? And we struck a deal and it was a strange thing where he made me the CEO of the company, even though he got the initial idea going, uh, [00:19:20] better fitting men's pants. And the only thing I really brought to the party at that time was. I was excited to go raise money for it because I wanted to be an entrepreneur. And I was really passionate about the consumer internet and felt that maybe a [00:19:30] physical product brand could be a consumer internet company, which was the original genesis of digital brands. It was all happening then. I think we were [00:19:40] one of the first or maybe even the first in the U. S. in getting going with, wait, maybe we can build a Better customer experience by going direct to consumer over the internet. I think in [00:19:50] retrospect, it's hard to build a better business doing it that way, like from the benefit of 15 years of hindsight, that was the idea and that's how we teamed up. **Leah:** Yeah, I think it's really interesting [00:20:00] in hearing your description of bonobos because you really said, let's go build something on the internet that hasn't been built before, which is [00:20:10] this physical product of pants, right? And let's sell them online direct to the consumer. That wasn't prevalent at the time. This is like a new idea to [00:20:20] take. a brand and make it digital and sell it online. And so I think it's interesting the way you approached it. It wasn't [00:20:30] just about selling the pants for you. **Andy:** Yeah. I'm thinking about the name of this podcast and breaking precedent, setting aside the identity question. Do you think of [00:20:40] yourself? I don't know, but what I do think is so critical and you know this from your journey is to build something new. It needs to break [00:20:50] precedent. It has to be non consensus. And I had a mentor at Stanford who used to talk about, you can be consensus or non consensus and then you can prove to be right or wrong. [00:21:00] And what most people don't understand about startups is that they were all non consensus at the beginning and only time shows whether you're right or wrong. What you can't be is consensus [00:21:10] at the beginning, because then everyone's already doing it, right? There are a lot of concepts right now in AI that are probably consensus and right. There's so many [00:21:20] people that agree on what should be. that it's unlikely that that is going to be an asymmetric breakout compared to a team working on something that is non [00:21:30] consensus. And I think Bonobos broke precedent over time in three ways. I think the first thing is a credit to Brian, which is that we could get [00:21:40] straight guys to care about how their butts looked in pants. Like the original core benefit of bonobos was we made men's butts look good [00:21:50] because of the nature of the fit, the curved waistband, the length of the rise. There's a funny thing in menswear, and I love this dye workwear account that the [00:22:00] triangle that's made by your legs in the ground, maximizing the area of that triangle is how you. look as fit and tall as you can, and it's [00:22:10] normal in, let's say, women's denim. That triangle is maximized. Right. Not always silhouettes change. And now we're in a moment where it's gotten back drapey. But [00:22:20] if you think about the core of the skinny jean movement over the last 20 years, **Leah:** Yes. **Andy:** Hold on. Are we out **Leah:** of the skinny jean movement? I'm like, I need to get clear on this [00:22:30] for women right now. I don't know what to wear. Tell me. **Andy:** I think we're kind of a fun, I mean, I like to watch what my Gen Z colleagues are doing at Pi, but I think we're in a moment where the [00:22:40] vibe is going like a little more drapey. Like I bought this really drapey, rag and bone, loose. Canadian tuxedo and I'm getting torched for it. I wore it on a tech crunch interview and my friends are like [00:22:50] Canadian tux. So yeah, back to questionable fashion. But I think that the idea that we could get guys to care about that, to be thinking about it, even if not as explicit, [00:23:00] that was breaking precedent. That was a credit to Brian's genius. The second thing was then to realize, By building the brand digitally, maybe we could build a better experience for the customer. [00:23:10] We could offer 365 day returns, free shipping both ways, keep them out of stores. I saw this happening with Zappos at the time. Yeah. And that [00:23:20] was the fun part about being in Silicon Valley was there was this like percolation of Sequoia just backed this shoe company. And you're like, wait, what? Why is venture capital getting involved in retail? And [00:23:30] I really admired Tony Hsieh and the way that Zappos was so focused on customer service. And so the thought was, what if we combined the [00:23:40] ruthless customer experience by being e commerce driven of Zappos with being an actual Men's brand like Ralph Lauren. And [00:23:50] that was actually a pitch. That was the slide in the original deck. That nice, brutal slide. That's like this company is X plus Y. And it's a little annoying, **Leah:** it works for investors. Investors are [00:24:00] very simple. Yeah. You got to like really dumb it down. **Andy:** Yeah. I was like, but everyone's this Ralph Lauren times Apple. So that was a breaking of a precedent. And that was one where people were like, [00:24:10] wait, what are you doing? How are you going to build a brand? No one knows through the internet. And this was one answer to that now would be like, well, we're going to use Instagram. Instagram wasn't launched. Right. This was 07. [00:24:20] So how are you going to build a brand online? And we made a bet that that's where the world was going. And then if you make the bet coming back to non consensus and right, the ecosystem emerges to [00:24:30] enable that, right? Shopify comes up, Instagram gets launched. And you start to see all these tools developing that made it possible. Facebook advertising platform [00:24:40] went live. We were one of the first 50 brands on Facebook. That was how we acquired a lot of customers the first year. And then five years later, we discovered. We actually needed a brick and mortar [00:24:50] experience too. That was the third. precedent breaking moment we had, which was developing a fit to ship store that doesn't have inventory. So I think for a good company, you keep [00:25:00] breaking precedent maybe every half decade. And that was actually funny that we like went back to it and we're like, wait, the future isn't all digital. It's also going to be Omni. And how do we now [00:25:10] figure that out and make sure that it works and still delivers on that same customer promise and that became the bonobos guide shop, which is a thousand square feet dedicated to great customer service. [00:25:20] We don't carry inventory there. We ship it to you. And a lot of people were like, that's really dumb. Who's going to shop at a store? where you can't take out the product. **Leah:** Yeah. **Andy:** And then it's like, wait, first principles, why is it good [00:25:30] to walk home with the product? Like, why is it good to carry a bunch of bags around a city or around a mall? Is that actually better? And then it was cool when that, when that worked. And I think there's [00:25:40] 60 bonobos stores now. So, **Leah:** so interesting. And then how did the Nordstrom partnership fit into that as well? Did the guide shops come first [00:25:50] and then Nordstrom or was it the other way around? **Andy:** this one's funny because it's not breaking a brand precedent, but it's breaking a direct to consumer brand precedent. And we were on the cutting edge of that, which is, [00:26:00] wait a second, wholesale isn't the enemy here. If you can find a great retailer that takes care of its customers, that pays its bills on time, that's not going to cannibalize your direct to [00:26:10] consumer business. That's going to enhance it. And that's when I flew out to Seattle and I met with the Nordstrom team. And we got on a whiteboard and said, okay, what would winning look like? And it was a million of sales, 2 million of [00:26:20] sales, 4 million of sales year one, two and three. And then we went 2 million, 12 million, 53 million. And that was like a holy guacamole. Like [00:26:30] you can sell 50 million of chinos, another account. And now for example, my sister's company where I'm a co founder and on the board, Monica and Andy, which [00:26:40] is organic baby apparel, Now it's all about how do we build the right wholesale relationships? And we're live in Walmart and we're having other conversations. of course you want [00:26:50] wholesale, but that was a breaking a precedent for this tiny cohort and crop of new brands that we were leading the charge on where we were mistakenly saying it's all digital.[00:27:00] And I actually don't think you can make money all digital for the most part because effectively it's just transferring venture capital to Mark Zuckerberg. Like that is how [00:27:10] digital brands work and we could nerd out on this, it's a topic for another day. The cartel power of the people that control digital customer acquisition, [00:27:20] Meta, Google, Apple, those landlords. Um, have far more market power than any physical brick and mortar landlord or wholesaler has ever [00:27:30] had. **Leah:** Right. **Andy:** So we kind of come back full circle to where we started with brand development, right? Now what's new and in vogue is figuring out how to be a DTC brand. That's getting great wholesale accounts lined up.[00:27:40] **Leah:** So as you back on the Bonobos journey, how do you feel like it has influenced your [00:27:50] I **Andy:** think what's coolest about Bonobos's legacy is that no one even knows now, right? Everyone has [00:28:00] digital. And I think we were followed by some entrepreneurs that built brands, Warby Parker, Harry's, Glossier, a way to name a few. Yep. Where I was so fortunate to [00:28:10] get to meet them early and talk to them and make angel investments. And it's like table stakes now. Right. Of course, you need to have a great digital experience. Of course, you need to have a great Instagram. [00:28:20] Of course, you need to figure out how to activate offline with experiential retail. It's we're invisible now. The contributions are known to just a few historians of how [00:28:30] digital brands emerged. Right. And that's a humbling thing to, it would be cool for people to be like, and Bonobos did this, but it's also really cool when [00:28:40] the innovation that you bring to the market becomes the norm. **Leah:** Super validating. You were able to see the wave that was [00:28:50] coming and you really timed it in the right way to ride it all the way through. **Andy:** Yeah. And I decided I'm not doing that again. This time, the precedents that [00:29:00] we break at Pi are going to be known because we're going to build a massive company. And that was the thing about Bonobos. It was always a tension for me is I wanted to take what we were learning and [00:29:10] turn that into a company that could have a bigger impact than just in quote unquote, this segment of premium menswear. And that actually led us to make a near [00:29:20] catastrophic mistake, which is We opened and built a huge team in Palo Alto to build software for digital brands, because we observed that there was no good software.[00:29:30] And we spent probably 20 or 30 million trying to write our own software. And it turns out and I would later have breakfast a couple years later with this guy named Toby. We sat down [00:29:40] for breakfast in New York City, and he was building this little company called Shopify. And it was like, Oh, this is a really good example of you can have the insight. You can see what's [00:29:50] coming, but you might not be the right person to do it. And you're also very unlikely to do it inside of another company. So the legacy of G2C, I feel [00:30:00] like the great company that got built is the company that empowered everyone to do it, which is Shopify. And it really burned me up that. I saw that, that that was like a big company, [00:30:10] but I couldn't manifest it. And of course, in retrospect, with all humility, it makes sense that that company would be built by a computer scientist and that company would be built by a computer [00:30:20] scientist who was going to focus a hundred percent of that company's energy on that, not trying to do it as a side hustle to selling pants. that's one of the thing that animates me [00:30:30] now is if you have the insight about the game changing opportunity in the market, Be that company rather than being the company that helps you develop the [00:30:40] insight. But as you know, once you're a founder and you're building something, you have an obligation to see that project through. Right. you know, I'm older now, I'm 45 and I'm so proud of [00:30:50] what Bonobos is. We put something in the world that's still here 20 years later. years later. And I think my son might be wearing bonobos, right? Like, I think it could be one of those [00:31:00] companies if things go well. it's funny, I'm an advisor to the new owner. Now that Walmart has divested it. **Leah:** Yeah. **Andy:** I think it could be here in a hundred, 200 years, the way that Brooks Brothers is still [00:31:10] here 200 years later, because guys, once we find something we like. We are not fickle. We are not fickle about our fashion choices. It's not like women's fashion where you got to re earn trust [00:31:20] every couple of years with menswear. It's like, I don't want to think about this ever again. This is where I get X, Y, and Z and I'm just like done. And then you shop that brand hopefully for 30 [00:31:30] years. **Leah:** Andy, as all of this is going on, you're running Bonobos, you sell Bonobos. You're at Walmart, there's this kind of big [00:31:40] secret that you're holding. And I remember when your book came out, Burn Rate, you and I are friends. I was [00:31:50] one of the first to buy it, read it, review it, a whole thing. I was like, Whoa, I had no idea. Can you walk us through [00:32:00] the decision to write this incredible book, The Courage? to come forward and be so transparent and be a really [00:32:10] important voice for mental health. Walk us through like, why now? Why then? What happened? It was a lot to [00:32:20] carry. **Andy:** Yeah, I had a good little secret cook in there behind the scenes the whole time. So yeah, the headline here is when I was 20. I was diagnosed with Bipolar [00:32:30] 1. It is a disorder of mood. It basically means your highs can get too high and your lows can get too low. On the low side, depression, [00:32:40] catatonic depression, suicidal ideation, super scary stuff. The suicide attempt rate for Bipolar 1 from diagnosis over the course of a lifetime is [00:32:50] 60%. So by definition, you're on track to experience some really dark times. And tragically, historically, the suicide rate is 20%. [00:33:00] So it's a very hard diagnosis to absorb because if you are data driven as I am, you're like, okay, the most likely way I'm going to die is to end my own life. And we can't accept [00:33:10] this. We have to change it. And I'm very sure that these numbers are changing because of the way the conversation is changing. And maybe even more importantly, or symbiotically with that, the quality of [00:33:20] the treatment is improving. so much, which we can get into. **Leah:** Okay. **Andy:** Then on the high side of bipolar, the unique characteristic of bipolar one is you're [00:33:30] not just capable of getting into an elevated mood state where you have higher energy, decreased need for sleep, grandiose ideas, rapid speech, increased [00:33:40] irritability. You've got all that. That's called hypomania. That is hallmark to bipolar two. It is also all of us at some point get into a hypomanic state for a [00:33:50] period of time. My doctor likes to say, might we all be controllably hypomanic every day? It's just being psyched. It's having a peak experience. So you've got a lot more of that than [00:34:00] is normal or healthy with bipolar two. With bipolar one, you have that and you have mania or psychosis, which is Vincent van Gogh cutting off his ear. That's [00:34:10] walking down the street thinking you're Jesus. That's people who have fully lost touch with reality and are behaving in ways that are very much not grounded in reality. And [00:34:20] typically it's a messianic delusion, which makes it hard to talk about because later it's like, Oh, That person kind of thinks they're God. And it [00:34:30] actually took me a while to work with my psychiatrist on this is actually incepted in all of us that we have this we're born unaware of our mortality. And then at some [00:34:40] point we watched Disney movies and realize our parents are going to die. **Leah:** So is Disney. Absolutely. Disney is the **Andy:** way that we educate our children, that they are going to outlast us, hopefully, and [00:34:50] that. We have a rage that develops inside that we have to leave. And so we are incepted with the wish to be superheroes or immortal. And of course, I joke about [00:35:00] Disney, the world's religious systems. Most of them are built on the promise of eternal life because it's very hard to cope with the idea that we're not going to be here forever. [00:35:10] And so I guess with bipolar, that kind of id, that desire to be all powerful or omnipotent or immortal [00:35:20] or the savior goes unchecked. You start to actually believe that it's true. And typically it's accompanied by not sleeping for several days. When I was [00:35:30] 20, when I was diagnosed in college, I was asleep for four nights in a row. So at that point, anyone's synapses are fraying. And I got this diagnosis, And the Indian half of [00:35:40] my family and the Scandinavian half of my family, very different, had one thing in common, which is like, let's just bury this shit. Let's bury this thing. And also the Midwest and my friends [00:35:50] and everything. It wasn't a culture of let's face this head on, let's talk about it. And the person leading the charge on that was me. I was in denial, didn't want to take my meds. [00:36:00] No, I don't have this. And we had a competing narrative that we could all belong to, which is that I'd been. doing a lot of stuff, mushrooms, smoking a ton of [00:36:10] pot, drinking a lot. So there was a narrative that it was the substance use that had induced the psychosis and this other medication I was taking that's a severe acne [00:36:20] issues on my back. There was a medication called Accutane and Accutane was great. It like was great in one regard. And then on the other hand, there was all this literature around [00:36:30] Accutane and mental health stuff. Which I think, I don't know, it feels like it could have been a correlation, not causation because if you're suffering from severe acne, you're probably a young person, [00:36:40] you're probably dealing with some stuff mental health wise, you're at a life moment where there's a lot going on. **Leah:** Yeah. **Andy:** almost tragically, we just buried it, myself leading the charge in. Mm hmm. I [00:36:50] pretended at least externally outside of in my darkest moments that I didn't have bipolar for 16 years. And of course I did something that a lot of people with bipolar [00:37:00] do, which is I started a company. And I say that jokingly, but the data bears fruit from UCSF, 2% of American adults we think have bipolar. 11 percent of the [00:37:10] entrepreneurial population we think has some form of mood disorder. So I have people come up to me now and they say, Hey, I have bipolar. Should I start a company or not? And I'm like, you have a five times higher [00:37:20] probability of being successful in theory. So there's a lot to what we could talk about here, but that's how it started for me. **Leah:** So, and I'm curious in [00:37:30] those, 16 years where you get the original diagnosis, but you're like, let's bury this. Let's not face it head on. Do you forget about it? Does it stick with you? Are [00:37:40] you worried that it's going to come back at some point? Like, how does it sit with you during that time? **Andy:** Yeah, it's funny. I had this conversation once with my mom when I was a kid. I remember [00:37:50] it about how there's this concept of repressed memories. of something that happened to you, that you can somehow your brain can become unaware [00:38:00] at the conscious level that it happened to you. And I remember having this conversation with my mom where we're like, yeah, that's BS. That's not possible. And it was actually a weird moment to knock the mental [00:38:10] health ecosystem because it was like, yeah, you go to therapy and they discover these memories. And I don't think it's true. It was funny, maybe unfunny moment, but in retrospect, it, **Leah:** in the arc of my life **Andy:** [00:38:20] story, it's darkly comic. Yeah. Yeah. Yeah. **Leah:** Yeah. And **Andy:** it was a little bit like that where I would go, as I recall, for months without thinking about what [00:38:30] happened, without having a conscious awareness that this thing happened in my life. And then maybe something would come up, what comes to mind for me a little bit is the early days [00:38:40] of feeling. Depression, which kicked in in my late twenties, particularly with having started a company and some of the stresses that came with that. So **Leah:** you had started Bonobos at that point. [00:38:50] **Andy:** I had started Bonobos and that was the beginning of having depressive episodes. **Leah:** Okay. **Andy:** So I had in a weird way, an unfortunate thing happened, which is that when I was diagnosed at 20. My [00:39:00] discharging psychiatrist said if Andy has no recurrence of mania or no onset of depression for the next five years, it's possible that this diagnosis isn't [00:39:10] right. There's a differential diagnosis quality. And my now doctor, who you can tell I adore from how often I bring them up, is like, she should not have said that. Not because it's not true, but [00:39:20] because it created a life raft. **Leah:** Kind of gave you an out. **Andy:** It gave me an out. I made it five years. I was like, all right, I made it. And then I would remember that it happened. And I would have this like [00:39:30] crazy rising anxiety and fear. then just push it back down. It was too traumatic to think about.[00:39:40] And now I get it. I understand that sometimes there's something in our lives that feels like it's too hard to bear [00:39:50] and we are blocked from it and we have to do some kind of work. I don't know. For some people, that's therapy. I think that's therapy is generally pretty good. Maybe for other people, it's [00:40:00] ayahuasca. We've got to do some kind of work. to get that out of our body to be able to look what happened to us in the eye, in a clear eyed way and [00:40:10] somehow make peace with it so that we can deal with that. And obviously that's a very tall order. **Leah:** It is a tall order. And 16 years later, you had [00:40:20] another episode. It happened again, this time You were able to face it head on afterwards and really take the steps [00:40:30] to get better. **Andy:** Yeah, I was very lucky. And also had grown up a lot. And also the world had grown up on this topic. [00:40:40] So the headlines here were, I had a second messianic episode. This time I didn't think I was Jesus. I thought I was some kind of a hybrid of Batman and the U S [00:40:50] president, which is badass. If you think about it. Extremely **Leah:** badass. Yes. Yeah. The dark **Andy:** night in the oval office, like what couldn't we get done? And of course I was just a guy [00:41:00] on nine street in New York city losing his mind. And. What made that episode so difficult, there were two things that made it difficult. One was the stakes were [00:41:10] so much higher. I wasn't a college kid doing things you expect college kids to be doing. Staying up all night, doing shrooms, drinking too much. [00:41:20] You're sort of in context of central casting college kid behavior, and you're early enough in your life where there's a lot to the story to be written. So if you can [00:41:30] make it through that, and that's typically the onset. In a weird way, there's less at stake. It feels like everything's at stake though, because it's like your whole identity and you're young. And it's like this thing of [00:41:40] being neurotypical is taken away from you. For me at 36, I had raised a hundred million bucks. I had 600 employees. I had a woman I was in love with who I was hoping to [00:41:50] marry. The stakes were much higher. so that was one thing that made it. hard. And then the second thing was that during the mania, I had a violent episode [00:42:00] where my now wife and mother in law tried to prevent me from running naked into the streets of Greenwich Village. And when I was discharged from the psych ward after a [00:42:10] week, I thought, okay, now I'm ready to deal with this. Mm-hmm . And I'm ready to take medication and see a doctor and patch up these relationships and talk to my work colleagues about this and [00:42:20] figure it out. And I was discharged straight in handcuffs because during that violent episode, I had assaulted my now wife and mother-in-law. So the charges were misdemeanor assaults and [00:42:30] felony assault of a senior citizen. And that just opened up a whole new ocean of shame and pain. And after mania, you typically have a very [00:42:40] long period of depression. So I was catatonically depressed for six months. I didn't want to live. I was in and out of the legal system with the charges. I didn't know if things would work out with Manuela. [00:42:50] And I didn't know if I had to step down from my job. I actually remember being worried about there being press about me being a domestic abuser. Like I could even picture the headline [00:43:00] of Bonobo's founder, named after a brand peace loving chimpanzees as a white beater or something like that. so it was kind of a horrifying time. And then [00:43:10] everything went right. Got a great doctor who helped me figure out the right medicinal cocktail, the right meds to get out of it. Took a half a year, but got through [00:43:20] it. So the medication working and having a great mental health provider, that's 80 percent of the battle. Got my sleep regimen down. didn't have to resign my job. My work [00:43:30] senior management team rallied around me. The board rallied around me. My family rallied and like really got clear eyed about it. And then definitely most importantly for the arc of my life, Manuela [00:43:40] stayed with me and her mom forgave me. And that was the most redemptive part of this because they were the only people that didn't have to deal with me. You know, your own family's got to take you [00:43:50] on. You've got a good family. Your family's your family. The work thing was magical, but also they kind of like, there was an existing thing. History there, but Manuel and her mom [00:44:00] should have maybe headed for the hills. That's what I thought would happen. And I remember sitting down a week after this all went down. I sat down with my mother in law and [00:44:10] try to picture this. The last time you saw someone, you were out of your mind and you assaulted them. And you're going to lunch. And I recommend Flatiron if you have to have this [00:44:20] conversation and we sat down and I literally thought it was going to be kind of, Hey, we love you, but you need to go get well conversation. **Leah:** Yeah. **Andy:** And I sat down and the first thing she put her [00:44:30] hand on my hand and she said, Andy, look me right in the eyes. This is just like diabetes or some other physical health condition. It's no different. But all you [00:44:40] have to do is take your meds. And see your doctor. And if you do, and if Manuela wants to be with you, then you have my blessing to continue in this relationship. And [00:44:50] then she goes, but if you don't, you're out, which was perfect. And then I cried for 20 minutes straight because on some level, this bipolar diagnosis [00:45:00] was a human stain that I felt. It was this darkening, blot on my, who, what my character and my soul. And it's in the language, right? on my Ted [00:45:10] talk. This was the main thing I wanted people to come away with, which is we don't say someone has bipolar. We say they are bipolar and the analog would be someone doesn't have cancer. They are cancer. And [00:45:20] so by conflating identity and illness and making people who are neurodivergent feel like. Not only do they have a mental health issue or maybe a mental [00:45:30] illness or maybe a severe mental illness, you are the severe mental illness. It's just like way too much to take on. Mm hmm. And so the act of love and acceptance [00:45:40] that Manuela and her family provided to me was to help me expunge that stain. Yeah. Because they basically said, you are not some broken person. You are not a [00:45:50] disorder. You're a human dealing with a health issue. And as long as we're going to hold you accountable to you dealing with that health issue, which is like super [00:46:00] critical, it's important to hold our loved ones accountable and to hold ourselves accountable to trying to improve how we show up. But if so, then yeah, you're good. You're just [00:46:10] Andy. You're the guy that Manuela was dating two weeks ago before this happened. And we're kind of cheering this whole thing on. And it was just amazing. I really rebuilt myself on the strength of [00:46:20] Manuela's love and her family's acceptance because they didn't need to do that. **Leah:** Yeah. And maybe not typical either. I mean, we're both parents now, right? And [00:46:30] if you put yourself in that. parent role, Manuela's mother, where do you think she drew that empathy from for you? **Andy:** I think first the [00:46:40] culture is different. Okay. Their origin culture. Jews from New York City probably have the highest percentage of therapists.[00:46:50] The highest percentage of people in the world in therapy are probably Jews in New York. And so I think there is something in the culture that I really was attracted to. And [00:47:00] part of why I converted had nothing to do with the religion. Well, the religion was important in my story for the conversion, because I candidly, I needed to belong to a religious worldview. [00:47:10] I needed a system to belong to just for me, because I was raised, you know, my dad is a Christian, but agnostic lapsed. Now my mom's Hindu. And I remember thinking like, well, they can't [00:47:20] both be right. And so I was really attracted to belong to a system and Judaism being the oldest monotheistic religion appealed to me. And I. met a great rabbi and that helped me a lot. That was happening at [00:47:30] the same time in my life as this, it was grounding for me. But then setting that aside, let's say you're an atheist or you're like setting that aside. Part of what I think is amazing about Jewish culture [00:47:40] is the candor is the idea that the most important conversation to have is the most difficult one to have. And even the gravitation towards [00:47:50] disagreeableness. or making it the norm that you're going to kind of like duke it out. I remember the first times I had dinner with Manuela and her mom, they got into what [00:48:00] I used to call a fight that I now just call a spirited disagreement. And Manuela was crying at the dinner and my Scandinavian Dad's side, I went to the bathroom and I was [00:48:10] literally dry heaving because I was hoping that this relationship would work. And now I'm with this family where you make someone cry at a dinner table. The first time you're [00:48:20] meeting like the meet the parents like dinner. And on some level, that's better than a family not having the conversation, which [00:48:30] is my dad's side of the family. He doesn't talk to either of his siblings. I just brokered a peace treaty dinner for him and his sister. who live 40 miles apart and haven't seen each [00:48:40] other for 17 years. waspy shit. Like you don't deal with your problems and it becomes Gothic and then you don't [00:48:50] talk. And then my mom's family, who are the Punjabi Indians, you don't roll like that at all. I like to joke that in that culture, you say exactly what you think in real time to everyone except the person that [00:49:00] you think it about. So there's very low confrontation, but very high transparency. Whereas in my wife's family and a lot of the [00:49:10] people around the ecosystem that I've met, like you just call a spade a spade. so I think that's part of it. And then so confronting hard [00:49:20] things and then also acceptance that mental health is not different than physical health. And I remember hearing about Manuela had a boyfriend once back in the day who was like very depressed and had a lot of issues, [00:49:30] but it was normal. Like they were just trying to get through that. Or my wife will now say like she feels like she was what my doctor calls dysthymia, like mild depression. She's [00:49:40] basically had mild depression for 20 years and that's her journey and figuring that out and what are the right meds. All that stuff is just like in the water in [00:49:50] a way that not at all. I wrote a fricking book about this and I literally just had to convince my uncle that it might be okay. for his daughter who was very unwell to take medication and [00:50:00] he felt resistant to it or I can't get anyone in my nuclear family to see a therapist for a year to save my life. And it's like, guys, this is so messed up. I wrote a book about [00:50:10] this. Yeah. Why am I the only one in this family actively trying to address my mental health stuff? What about you guys? So that's how. strong. These forces [00:50:20] are, **Leah:** yeah, well, the book is incredible. Your Ted talk is incredible. I encourage people to read it. Go watch one takeaway. I [00:50:30] have from reading and watching is that you do deeply understand. The science and the mechanics behind the [00:50:40] neurodiversity. And I'm wondering, do you think that understanding deeply someone's neurodiversity for themselves [00:50:50] is an important piece of being able to manage it? Or is that just maybe something that you needed to do for you to be able to come up with the [00:51:00] plan and the regimen and all the things in order to function well? **Andy:** Yes, I think so. I don't think you have to turn it into sport the way that I have. You [00:51:10] don't need to write a book and give a TED talk. **Leah:** Yeah. **Andy:** You probably don't need to see a psychiatrist twice a week for a lot of Let's call it neurotypical people. If you have pancreatic cancer, you've [00:51:20] got to get pretty into your chemo regimen, right? Yeah. But even if you don't have pancreatic cancer, you need to get into your fitness and nutrition and sleep program. We all have kind of table [00:51:30] stakes, things that we need to do for our mental health. We all have dental hygiene, right? Like you're going to end up with cavities if you don't brush your teeth and floss, you're going to have issues later. And I think mental hygiene is like that. [00:51:40] And I think part of a mental hygiene. or a mental fitness routine is first understanding that we all have mental health. Second, understanding that there are tangible things that we can do to improve it. And [00:51:50] I think part of that is, and I'll just give you my hottest take. My hottest take is that no matter who you are, you should do therapy for a full year, once every three years, because it will just help you [00:52:00] understand yourself better. And I try to appeal to self interest and say that this is one of the investments you can make. in having meaningful relationships in your life, in [00:52:10] being professionally successful, in finding inner calm and peace. And so treat it not because you're broken back to 2000 [00:52:20] Midwestern values. Treat it as like having an awesome personal trainer for a year because you really want to get in better physical shape. So I think that's something that we all should [00:52:30] do if we can get the care and afford it and solve a lot of those problems, which are non trivial problems to solve. **Leah:** Yeah. I want to talk about the concept, which I [00:52:40] love, of turning a perceived weakness into your superpower. Yeah. Because. That is incredibly powerful. And I [00:52:50] think we all have something that we're dealing with, something that other people see as a weakness of ours. But for you, how has this actually been a [00:53:00] superpower strength in your journey? **Andy:** I was at a dinner once in New York City with a bunch of CHROs and entrepreneurs put on by the guy who started Project Healthy [00:53:10] Minds, Philip Schirmer. And we were talking about this thing, there's so many different. little sayings I've learned that I love. So, strengths have shadows is one that I like to say.[00:53:20] I've heard that. Another one is the gift is in the wound. Another one is there's beauty in the brokenness. All these things are true. There are these [00:53:30] things that come to us in life that we don't want. It's like the dark visitor at the door. with the bad news. And the normal frame is like, slam the door. [00:53:40] But the inverse is invite that agent of doom into your home and sit down and have a conversation because you don't know what it means yet. You don't know what's bad [00:53:50] news or good news in your life until later. And there's a lovely book called Falling Upward by Richard Rohr, who's a Franciscan friar. It's actually the only book that I had [00:54:00] space for whatever reason to read while I was writing my book. And he basically says that by the time you get to your 45th birthday, by definition, there is something that has happened to you in your life. [00:54:10] That you did not see coming or you didn't spend time anticipating that turns your life totally upside down. That just crushes you and [00:54:20] that feels like I didn't want this or this was never going to happen to me. It can be a divorce. It can be the loss of a loved one. It can be so many things, professional, financial ruin, but something pretty [00:54:30] bad that feels bad and that the secret to having a good second half of your life is to embrace what that is. And make it a part of your [00:54:40] identity, internally and externally, that he refers to as taking off a mask. That we spend the first half of our lives constructing an ego, because it's in our nature. [00:54:50] We're looking to mate, we're looking to gain status. Whether we do those things or not, we're looking to self express. We're looking to figure out who we are to express our [00:55:00] identity. But it is a mask. It is not your soul. It is a mask that you've constructed to define who you are, to tell yourself who you are. And it's the mask that the world now sees you through. [00:55:10] And the goal of the second half of your life to become, he always refers to the elders, like to become like an elder that is of great service to the community, to be a person in your seventies and your [00:55:20] eighties and your nineties, who's just a to the community. Is that you now have taken that mask off and just shown people who you really are. [00:55:30] And here's the secret. Nobody fucking cares. Nobody cares. No one is thinking about you except your mom or something like [00:55:40] no one cares. So if we have a chance to show who we really are or to pretend to be someone else, what is our choice? **Leah:** Yeah. **Andy:** And I think it takes a certain amount of life [00:55:50] experience to have that messiness to share, to metabolize it and process it. And that's why I think therapy is important because it's hard to figure this stuff out on our own. I mean, maybe if you've [00:56:00] got the coolest friend in the world, you can sounding board this out for a while, but I think it's been such a gift to me to realize how much acceptance there is for doing this. Because it's what the [00:56:10] people want. Give the people what they want. Like who you are, you're suffering, what's hard, that's like the good stuff. And as I learned in my day job now, like focused [00:56:20] on platonic friendship creation with my startup pie, the two ingredients in a great. relationship, the headwaters of a platonic friendship are seeing someone again and again in a group [00:56:30] setting, and then at some point getting to mutual disclosure of vulnerable information. And so I think if we can get to a place in our lives where we lead with that vulnerable information, man, it's amazing [00:56:40] how much power there is in that. Hence the gift is in the wound. **Leah:** Let's talk about pie. I'm so excited to talk about pie. How did this start? What is [00:56:50] it? Give us all the details. **Andy:** Well, it's funny cause I don't normally tell the full version of the story cause there's not time and context, but actually the original idea for pie was something called [00:57:00] pumpkin pie. And it was maybe to return the favor to the remarkable role that my mother in law Lenny has played. It was to build a dating app for seniors. Because one of the things that I [00:57:10] identified was people are living well, I don't know if men are living longer, but people are living longer. And how do you meet someone as a senior? And I had been a early investor and a [00:57:20] board member at hinge. And so I got to see the hinge bumble tinder thing happen. And that was super cool to be a part of. And I started to wonder, maybe the product is different for seniors. Cause I [00:57:30] started ghosting as my mother in law on the dating sites. Like I'd be like, Hey, can I have your phone? I wasn't swiping or messaging people, but I saw what the experience was like. And [00:57:40] we all struggle with writing profiles and expressing ourselves. I think those challenges are more acute. Find a 75 year old man who writes a good dating profile. Like I'm still looking for one on her. I had been, [00:57:50] and it's in a different era of life where there's this very knowable body of. work about who you are that's behind you. I think when you're dating in your twenties, [00:58:00] a lot of what you're trying to do is project your hopes and dreams onto the future and find a person to do that with and co build the future with. But a lot of who you are hasn't been [00:58:10] revealed yet. Whereas if you're dating in your seventies, The lion's share of your life is behind you empirically by definition. You have made so many choices in life that have shaped [00:58:20] you and that reveal who you are. If you were going to have children, you did it. If you were going to get married, you probably did that once, right? Your professional stuff [00:58:30] is behind you. So I thought, gosh, there's so much data as like a data nerd. How do we get people to actually share that relevant data And then [00:58:40] how do we use algorithms to connect people to help seniors cut through the noise? And that's how Pumpkin Pie started. so the [00:58:50] headlines are, we built a really cool gamified quiz based intake with matching. And then very quickly, we discovered that our algorithm sucked for dating it like [00:59:00] statistically, we couldn't get it to matter, but it had really high signal for platonic friendship. **Leah:** Nice. **Andy:** And that then led to this moment of like, well, wait a second, let's savor the surprise here. And the surprise [00:59:10] here is that senior citizen dating is a hard problem and we're not going to solve that. But there is this other thing. Wait, what about platonic friendship? And this was like pre COVID when we [00:59:20] started it, it was prior to the loneliness pandemic being articulated by the Surgeon General last year. So we kind of saw some of these things coming and we started leaning into that. And then [00:59:30] we spent a few years building it and getting nowhere, partly because I think in retrospect, we were building a company about connection and forming IRL connection in real life. We're building the [00:59:40] company remotely due to the pandemic. And so we had a come to Jesus moment last year where it was like, we got to figure out how to get momentum here. And the decision was let's build it in person here [00:59:50] in Chicago. And I made offers to the whole remote team, not big, but like eight, 10 people, no one came, which was a little bit of a, no one came. And I think it's like a, [01:00:00] it's a good commentary on the air that we just lived through, which is that people became very attached. to their personal lives. People became more balanced, maybe in healthy ways between professional and personal [01:00:10] lives. And so the psychic attachment to the company wasn't as high as I recall it being for the people at Bonobos. **Leah:** Yeah, **Andy:** certainly for some people, like for my co [01:00:20] founder, Jen, it was, but for the whole team, it wasn't the same. I'm not necessarily a big believer in hybrid or remote for pre product market fit companies. I think it's [01:00:30] very different if you have a real culture that you've built in a real business. And you are now taking advantage of hybrid, then literally trying to build something hybrid. I don't know. I'm kind of short [01:00:40] that whole portfolio of overvalued pandemic startups that think they can build a work life balance utopia. And so then we started doing it in person and now we're just cooking. It's growing fast. We've got a [01:00:50] great team, great culture. We're live in Chicago, approaching 50, 000 monthly active users, and we're just having a blast. **Leah:** I mean, it's awesome. I love that you've put this stake in the ground [01:01:00] too, around in real life, IRL in Chicago. Office there in person events. And, you know, it is we're coming out of [01:01:10] this COVID era where everyone's on Zoom, everyone's remote, everything's changed. And you said in the beginning of this episode, [01:01:20] You wanted to be the big company and build something that's brand new, that no one's done before. This is a moment in time, it feels [01:01:30] like, where you are putting that stake in the ground and you're saying, this is how we're going to do it. **Andy:** I think the next big social network is going to be the competition [01:01:40] for offline attention rather than online attention. I think it's going to be, how do we take all these things that we've learned to do for good and evil with technology in the consumer [01:01:50] internet. And how do we point that same set of learnings and technologies at getting people to connect in person more? I think [01:02:00] there's going to be one to two really large companies that emerge. I don't know who it's going to be yet. I think you can probably guess who I believe it's going to be. And it's going to be, whether it's Pi or not, from the [01:02:10] vantage point of anyone listening, it's going to be so cool because we need to have some forces of getting people addicted to being together in real life to compliment.[01:02:20] These incredible forces and powerful ones that have gotten us addicted to our screens. **Leah:** Yeah. **Andy:** Not because social media is going away, not because we're going to be watching less Netflix. Not [01:02:30] watching it, but because we need to watch less. We need to compete with the quality of the experience of watching Yellowstone or being on TikTok. And that's going to take kind of hacking the human [01:02:40] psyche in algorithmic ways. and really smart ways. And we built those skills. And so now how do we apply that? And the AI inflection point is super [01:02:50] exciting because the hardest thing about platonic friendship formation, other than getting into a ritualistic environment of seeing someone again and again, which is very difficult to do once you've [01:03:00] left the places of social collision of your youth. And especially with hybrid work, like how do you run into someone five to 10 times? But the hardest part, even beyond that, is [01:03:10] then how do you get to this mutual disclosure of vulnerable information? Which is to say, how do we get you in front of who you're going to click with? And that's a very big data problem. And it's one where [01:03:20] prior to LLMs, I don't know that it could have been done that well because it would have been done that well. our most exciting initiative right now is called Spark Connections. And it's taking a lot of [01:03:30] the information that we have and putting together dinner parties of six. And I went to one last week and I actually was really tired and I wanted to just go home and hang with Manuela and see Isaiah. And I was like, I have to go, it's my [01:03:40] job. And I went and I had the most amazing night. I met two public school teachers who were at my table, a guy who had been through rehab and was a drummer in a blues band. And I just was like, [01:03:50] this is what makes Chicago so awesome. And I never meet people like this. And the public school teacher thing really stirred something in me because my dad has stage four cancer. He's doing okay. [01:04:00] Thank God, modern medicine, but he's a public high school teacher. And so I grew up around teachers and yet I haven't met a public high school teacher [01:04:10] since I was in high school. I don't have any teachers in my social life for 20 years. And now I'm at dinner with two and I'm like, I fucking love teachers. Yeah. It's like, yeah, really in [01:04:20] it for the right reasons. And yeah, it was just cool to get outside my bubble and it's fun when you get to drink your own Kool Aid and be like, okay, this is special. **Leah:** If you were tasked [01:04:30] with redesigning how society defines and measures success, not just in business, but in life in general, what would that model look like? **Andy:** The most [01:04:40] spicy thing I can say is that we need to acknowledge that there are going to be seasons in our lives where we need to distort our attention and [01:04:50] energy into building the future, which is about families, primarily. It can also be about professional endeavors in ways that [01:05:00] sacrifice some of our present mental health for the future meaning that we're creating and the potential for others to be mentally healthy, right? What [01:05:10] is parenting, if not an exercise in sacrificing your mental health for the future wellbeing of this person? So **Leah:** true. Well said. And **Andy:** I'm on team procreation. [01:05:20] I'm all for people that are doing life differently, don't want to have kids, whatever. That's great. Yeah. I'm all for that and I'm also for the importance of family and the importance of investing [01:05:30] our attention to energy in future generations. And so what I tell my team now with Pi, because Pi is also a distortion of energy. I like to joke, we are [01:05:40] sacrificing our mental health for the quality of our community. But I try to be careful with it and say like, please don't come if you are not in a season of your life where you want to put a lot of your energy into [01:05:50] building something. In return, you will have hopefully opportunity to grow a lot, learn so much advance in your career, build great [01:06:00] friendships. Maybe there are differential economic rewards. Let's go build the PayPal of Chicago. We call it PayPal culture of let's throw off 10, 000 angel investors and a thousand [01:06:10] entrepreneurs. But by the way, that requires 50 to 60 hours a week of work. So we're talking about if it's table stakes, 50, that's nine hours a day. So it's not an [01:06:20] eight hour day. And that's five hours on the weekend. And that's the expectation set here. It don't come if you don't want that. It don't come if you haven't built the infrastructure to be able to do that. [01:06:30] And so that is this thing that we have to acknowledge is it's not about 10 mental health days a year. It's not about everyone needs to just have this Zen thing and we're going to turn [01:06:40] into Western Europe or whatever. I guess we could, but it's about choosing those seasons, investing in. being robust for it. And then I hope and God bless and [01:06:50] life willing having other seasons of your life where you've got a different vibe and a different approach. That's how I think about it. **Leah:** I love that. Okay. If you could [01:07:00] wave a magic wand and break any societal precedent, what would it be? Um, **Andy:** right now there's a big one, which is I want it to be [01:07:10] totally normal for people to hang out with folks who belong to the other political party. **Leah:** That's very timely. The **Andy:** first two Trump eras, I didn't have any Trump [01:07:20] friends and now I have a ton because I actively over the last four years did two things. I sought to identify this very pernicious allergy that [01:07:30] we have to people that have different political views than we do and treat it almost as a mental health. thing. Like this is just weird. Why it's okay. [01:07:40] Right. And then the second thing I did was I spent a lot of my time and energy ingesting concepts, thoughts, ideas, perspectives from quote unquote the [01:07:50] other side. So I read the wall street journal opinion page every day. I listened to a lot of these heterodox male podcasters who actually are kind of homogeneous in what [01:08:00] they say and think. It's kind of cute that they call themselves the heterodox, but like, I do it. I like listen to Theo Vaughn and I think his Netflix stuff is hilarious. And I'm not like, [01:08:10] I would never listen to the Joe Rogan or not. I listened to it. And I also found there are people in my life who are politically very different. And I leaned into it. I've got a cousin [01:08:20] who's super pro life and I just kind of got in there and we text about it and he's like, Hey, this is a dark note to end on, but he's like, do you want to see a bunch of pictures of a 13 week old fetus? And [01:08:30] I was like, I guess I do. And then I got the text and I was like, that looks like a baby. And it didn't change my personal beliefs. But it did change a little bit like, eh, [01:08:40] maybe we could be like Western Europe and it should be abortion through 25 weeks, right? Like, whatever. Setting aside that issue, which happens to be like a pretty big, hot bidden, dismissive issue, [01:08:50] how do we expand our minds and say, it's like the Dr. King? Love your enemies. And part of that is it's not your enemies. It's just other Americans. So that's like a big [01:09:00] dream that I have for our country is that we can learn to be friends again with people who are politically different. It doesn't have to be a lot, but just literally like one [01:09:10] friend in your life. Who's different in that way specifically, because you know, what you'll find from what I found is If you love that person, it will just soften you [01:09:20] will enable us to make a lot more progress and be much kinder to each other, which I do think is important. **Leah:** All right. Last question. Do you tend to follow your mind, your [01:09:30] gut, or your heart the most in decision making? **Andy:** I think my mind, I've learned from Manuela to really value gut, I think [01:09:40] the heart's overrated. I don't know if the heart makes good decisions, but that you have to apply an empirical frame informed by your gut to [01:09:50] make a decision. I'll just give you a quick example, which historically I've been mediocre at hiring because I love people and I can always see an angle for why this person can do it. I'm [01:10:00] defaulting to yes, and now I default to no. which was very hard for me. I assume going into interview that the probability that this person is the best person for the job is below 50 percent [01:10:10] if we're doing our job. So if you're getting to at least three to four good finalists, that means by definition, and how do I disprove the null hypothesis rather than try to start it? Yes. [01:10:20] And disprove one leg of it, which then invites, okay, probably I've got to do two to three back channel references. to figure out how to prove or disprove that. So I think the gut and the heart are [01:10:30] so important as like the ingredients in decision making, but the mind has to make the final. **Leah:** It's great. Well, Andy, you have done [01:10:40] so much in your career and life and your journey. And I just want to thank you for being so brave and courageous and bold to be [01:10:50] transparent about your story, because I think it just is so helpful To everyone. So many people it's so high impact and I'm really excited about. [01:11:00] Hi, and everything that you're doing next. So thank you. **Andy:** It's great seeing you. Thanks for doing this. It's an honor to be here. **Leah:** That was Andy Dunn. I [01:11:10] found his take on turning perceived weaknesses into superpowers, incredibly compelling. Everyone has something they struggle with, and if you're able to shift your perspective and leverage [01:11:20] your differences as Strength, that can be a huge unlock. I also appreciated Andy's vulnerability and authenticity in this conversation, breaking precedents around [01:11:30] mental health and neurodiversity. Thank you for listening to Breaking Precedent. Remember to click the follow button on your favorite podcast apps so you never miss one of these [01:11:40] exciting conversations that challenges the status quo and inspires change. And if you know someone who is trailblazing a unique path, I wanna hear their story. You can send a [01:11:50] note to me on my website, breaking precedent. com until next time. I'm Leah Sullivan.