Andy Dunn on Entrepreneurship, Bipolar Disorder, and Cofounder Divorce

Andy Dunn: So my diagnosis became a little bit like fight club, which is “We don’t talk about fight club.” We just buried it, and my friends buried it, too. So I internalized that as an unspeakable shame, because what is shame but what is unspeakable.

Cyerra Homes: Welcome to View From The Top, the podcast. That was Andy Dunn, Founder and CEO of Bonobos. Andy visited Stanford Graduate School of Business, as part of View From the Top, a speaker series where students, like me, sit down to interview business leaders from around the world.

I’m Cyerra Holmes, an MBA student of the class of 2023. This year I had the pleasure of interviewing Andy. He shared invaluable insights on building community, driving impact and embracing change. (short pause) You’re listening to View From The Top, the podcast.

Cyerra Homes: Andy, welcome back to the GSB.

Andy Dunn: Thanks for having me.

Cyerra Homes: It is such an honor to be sharing the stage with you. Your story of founding Bonobos, from launching the company here at the GSB in 2007, to selling it 10 years later for $310 million, is truly inspiring. I’m so excited to dive into all of this today, but before we begin, I wanted to introduce Bonobos to those of you who may not be as familiar with the product. So, in a View from the Top first, let the fashion show begin.

Male Voice: On your left, you have [Yes Shane] in Italian stretch chinos. On your right, John Henry Styles in original stretch wash chinos. On your left, we have Diego Ramirez in original stretch wash chinos. On your right, James Underwood in stretch wash chino 2.0.

Andy Dunn: Oh my God.

Male Voice: On your left, we have Ashirwad Gupta in [Yandai] stretch chinos and Mike [Pang] in slim straight chinos.

Andy Dunn: Amazing.

Male Voice: On your left, we have Aramide Olaniyan. On your right, Jonathan Wilkins in original stretch wash chinos. On your left, Sonny Stephens in the stretch weekday warrior dress pants and Logan Randolph with the Bonobos light wash jeans. Last but not least, on your left, Jon Gilhooly in stretch weekday warriors and Joel Bateman with the stretch wash chino 2.0. Please give a big hand for our models.

Cyerra Homes: I’m sure you’ve seen and been a part of quite a few fashion shows.

Andy Dunn: No, not like that.

Cyerra Homes: How did that one stack up? Not like that?

Andy Dunn: Not like that.

Cyerra Homes: Me either. Well, Andy, many people know you for the pants that we just saw, and if they didn’t before, they do now. But not many people know about what you refer to as your ghost story. I’d like to read a powerful excerpt from your book Burn Rate, if that’s okay with you.

Andy Dunn: That sounds good.

Cyerra Homes: Thank you. “In 2016, on the precipice of selling Bonobos, the startup I’d been building for the previous nine years, I flew into a manic spiral and was hospitalized for a week in the psych ward at Bellevue in New York. When I was discharged, I was met by NYPD officers who took me to jail, where I was charged with felony and misdemeanor assault.” Whoa.

Andy Dunn: Good cliffhanger.

Cyerra Homes: Thank you. Not many successful business leaders talk about their struggle with mental health, so first of all, thank you for being so open in doing so. We’ll spend a good portion of the interview later discussing this, but every story has a beginning, so let’s start with yours.

Andy Dunn: Yeah. Sounds good.

Cyerra Homes: You grew up in the Midwest, the son of a U.S. history teacher and an ultrasound tech. Tell us a bit more about your upbringing and how it influenced you.

Andy Dunn: Yeah. Well, it was funny, because the editor and my agent basically said, “We need a chapter at the beginning of your book about your upbringing.”

My initial reaction was, “There’s nothing interesting about my upbringing.” I hadn’t really thought of anything that unique about it. Then, as I got to work on that, I was like, “Oh, there’s some stuff here.” My mom’s an Indian immigrant born in a refugee town on the way from Rawalpindi, Pakistan to New Delhi, India at the time of the partition. Somewhere between 1 and 2 million were killed at a time when 14 million people were displaced. So her origin story is in the midst of that strife. Settled in New Delhi, came to the U.S. when she was 20. Her father grew ill from emphysema. He was the only one who was of financial means, so it was, financially, extremely stressful. Her mother was a child bride, so promised to be married at about 10 or 11, married by 12 or 13, two miscarriages as a teenager, then two children who died in infancy, and then seven children, the middle of whom is my mom. My mom’s oldest sister, [Maimasi], delivered me. She became an ObGyn. So if you ever had this dynamic in your family where you have an aunt who can say to you, “I put you in this world. I can take you out of it. You’re being sassy” — so that was a bit on my mom’s family.

My dad’s family were kind of classic Scandinavian Midwesterners, so Danish, Swedish, Norwegian, all of that. So I grew up in a biracial household, and I think maybe the most interesting part of that, in retrospect, for me, is how different the cultures were around communication. In my dad’s family, you don’t talk about small conflicts. Those bubble up and become big conflicts, and so eventually you don’t speak at all. Very tragically, he doesn’t speak to either of his living siblings. On my mom’s side of the family, you say exactly what you think to everyone except the person that you think it about. All the information gets around, but with no conflict. My mom’s a little different with us.

Fast forward to later. Now I’m married to a Brazilian Jew who’s descended of the Brazilian in New York City Jews, and you say exactly what you think, in real time, to the person that you think it about, such that the first time I had dinner with my now wife and mother-in-law, either my Scandinavian side or my Indian side was in the bathroom, dry-heaving, being like, “I can’t be a part of this family,” but in truth, that might have been a family coming together versus falling apart.

This is some of the origin story for my family, and I think the other piece of it is my sister. I have an incredibly loving older sister. In Hindi, we call it our [didi]. We have a business together now, which actually is a really bad idea. We’ll talk about friendship and business and family and business. In truth, it’s brought us much closer together, because we have more time to spend, but also, it’s challenging. Family and business is challenging, just as friendship and business is challenging.

Cyerra Homes: Well, Andy, we have something in common. My mom also tells me that she brought me into this world and she can take me out, so I have heard that as well.

Andy Dunn: Yeah.

Cyerra Homes: You grew up in the Midwest, and you ended up leaving and coming to the GSB. Here in 2005 is where the idea for Bonobos was born.

Andy Dunn: Yeah.

Cyerra Homes: Your roommate in Schwab, Brian Spaly —

Andy Dunn: Yeah.

Cyerra Homes: — ended up becoming your cofounder.

Andy Dunn: Yeah.

Cyerra Homes: Take us back to those early days of Bonobos on campus.

Andy Dunn: Yeah.

Cyerra Homes: And why men’s pants?

Andy Dunn: Yeah. It was inverted, actually. Brian was the founder of Bonobos, and I became his cofounder, and the way that it went down is this. Brian came in and felt like there’s this one problem that he had, which is his pants didn’t fit, and so he did one of these projects. I can’t remember what they’re called. G300. It used to be called a 300 project. He went out and he got the survey with all of our classmates, and the basic insights were guys wear jeans because khaki pants and wool pants don’t fit that well. So that was insight number one. Insight number two was guys don’t like shopping in stores. Then insight number three was that J. Crew and Banana Republic were the two main places.

So his view about men’s pants was very specific, which is that, if the pants fit around your thighs and your butt, they were probably too tight in the waist, so that, when you sat down, you were really uncomfortable, back in an era where you had to wear pants to work, right? So then, as soon as you got home, you threw your jeans on, and your weekend going out was like denim. The thing that happened in premium denim in the ’90s was there was stretch that was added to the fabric, which had never happened before. Step one was Brian added stretch to khaki pants and wool pants, which was not a massive thing at the time.

The other insight that Brian had was that pants are kind of boring, and so he developed this contrast liner that would peek through the back pockets that would kind of create a conversation — they called it conversational prints — in a very specific place. He started just selling pants to our classmates. He found a factory in San Francisco and he found a pattern-maker in San Francisco, part of the last dying vestige of the fashion industry here, and he brought pants that he had worn, where he would buy a size 34 that fit his thighs and then tailor it into a 32, which is like an $80 alteration, probably that no one here has ever done, because you have Bonobos, right? Bonobos pants are made with that contour, like curved waistband. Then he drove to L.A. He bought a bunch of fabric. He picked a really cool pinwale corduroy, really thin, really lightweight. It had great stretch, which is kind of perfect for Northern California, because it’s cool in the morning, and then it kind of heats up during the day. He just started selling them to our classmates for $100, and it was like, well, one person was wearing them, then five, and then at some point like half of our classmates were buying pants. We did a pants party at our house. I don’t know if anyone has this house on El Camino Real. It used to be called the White House. Anyone live there?

Cyerra Homes: Still around today. Yes.

Andy Dunn: Still around? Yeah, so. Brian tried to rebrand it to Pleasure Town, which didn’t stick, so then it went back to the White House. Brian is an eccentric character, and hopefully, many of you will meet him in MGE or have met him. We had a pants party where people were playing whatever games and lawn games, and we sold $16,000 of pants that day. So, if you ever have a product or you sell that much and it’s a legal product, you might be onto something.

Cyerra Homes: Yeah, and you definitely were. That is incredible, to sell $16,000 worth of pants in one day. After the GSB, you decide to work on Bonobos full time, while Brian decides to take a job in PE and work on Bonobos on nights and weekends. What gave you that conviction? I know so many of us entrepreneurs and aspiring entrepreneurs are wondering whether or not we should take that leap of faith.

Andy Dunn: I went on a GSB service trip to East Africa, and it was like ‘12 or ‘13. You have these service learning trips still? We did a home stay for two nights, and I lived with a guy named Stanley and his wife and two kids, and it was a clay brick house without running water. They prepared a wonderful meal, of course, and then there was a big bucket where you dump it over your head, and generally, it’s cold water, which is like the ice bucket challenge. Of course, they found a way to heat it, which was wonderful, and it’s also an outhouse where you shower [very] close by.

Then I came back to the White House, the one here on El Camino Real, and my bathroom, you had to walk outside to get to, and it had two showerheads, which is plush. I turned them on, and the hot water hit me, and I had this moment where I was like, “We do not actually take that much risk,” the way that we define it in the U.S. For people in the cohort in this room, it’s actually not risky to start a company. It’s an insult to people whose lives are actually risky to think of it as risk in similar terms, and I don’t mean that in a judgmental way. Many of us have reasons. There are medical cost reasons and children, and there are things to be thoughtful of, but in terms of having our future net present value — is in pretty good shape. If you define the risk of not doing something that you love, and that I think is a spiritual risk rather than a financial risk — and so that trip changed me, and I felt like, “Okay. Even though I have $3000 in the bank and 182,000 of debt,” maybe a third of which was elective, just having fun and traveling, “I’m probably not going to starve one day.”

With that perspective, I was like, “Okay, then what can we go do?” I had no good ideas of my own, so I thought, “Okay, I’ll just steal Brian’s idea.”

Cyerra Homes: Worked out well. That is a helpful reframe around risk, and that reframe allowed you to take the leap of faith to move to New York and to work on Bonobos. At the time, you were truly a pioneer, building a direct-to-consumer, digitally native brand. Just to take everyone back to 2007, Amazon was irrelevant in fashion. People thought ecommerce was going to be an afterthought, and if you were a fashion brand not selling through the likes of Barneys and Bloomingdale’s, you were doomed to fail. Andy, how did you have this aha moment to build a digitally native brand, and how did you convince others?

Andy Dunn: Well, first, what is it? Great entrepreneurs are just thieves. Then, second, the future is here. It’s just not evenly distributed. If you want to build the future, don’t look to the future. Look to something that’s in the corner in the present. And then, past is prologue, which is that, more or less, we’re the same species the last 200,000 years, so there’s probably something in history that might alert you to what was coming.

For that third thing, for me, it was that I had worked at Lands’ End as a second-year Bain AC. Has anyone spent a couple winters in Dodgeville, Wisconsin? It’s cold. There’s not a lot to do other than just work. I got to see this storied catalog retailer that didn’t have stores. I remember one day touring the call center and seeing all the note from customers that had been mailed in, and there was a note from a woman that said, “Dear Elizabeth, thank you so much for calling me to wake me up the morning of my wedding. My mom was a mess. My bridesmaids wanted to sleep in. You’re the best, Carolyn.”

I was like, “Oh, the paradox of retail is that, by not having brick-and-mortar stores and going direct” — and this was the catalog innovation — “you can actually build a better customer service relationship.”

Then, in terms of what was happening in the present that was in the corner, there was this company called Zappos and an entrepreneur named Tony Hsieh and backed by Sequoia. You know startups, how there’s little rumors. You don’t know exactly what’s going on. You see that they exist. They were selling shoes. This was a time where ecommerce people were selling cars on eBay Motors, but it was like, “Well, you’re never going to sell shoes, because you got to try them on.” Well, don’t you have to drive the car? But Tony had three returns both ways, 365-day return policy, and a really spirited service team who were core to the company culture, and that’s obviously what Delivering Happiness is about, the book, and the irony of that title relative to Tony’s fate — I guess we’ll get to that type of conversation later.

I was like, “Well, if you can sell an existing soft goods product, footwear, then presumably you can sell an existing soft goods product, clothing. And why can’t you build your own brand?”

Then I kind of looked at the history of The Gap, which used to sell Levi’s jeans and records. Then an entrepreneur named Mickey Drexler came in and said, “Well, the margins on Levi’s jeans are here. Why don’t we make Gap jeans? We would get another 20 percent margins.”

Well, it’s like, “Well, you’re a retailer with stores. You’re not a brand.”

But he said, “No, let’s vertically integrate that.” Now everything from — you pick it, right, from IKEA to Zara, it’s all vertical now because of that margin trade.

So I took those three ideas and put them together, and then I went out to pitch people on the concept, and everyone said no, and that made me really feisty and also is a part of innovation, which is that it’s got to be contrarian at the time.

Cyerra Homes: Well, you were really on to something in building this direct-to-consumer brand. On the surface, it seems like things are going well. This is 2007, 2008. But internally, if you look under the hood of Bonobos, you were dealing with quite a bit of friction with your cofounder, Brian Spaly, as you’ve alluded to. Can you take us back to that time in the life of Bonobos and —

Andy Dunn: Yeah.

Cyerra Homes: — what happened there?

Andy Dunn: Well, I blamed everything on him. It’s easy in life, I think, to see someone else as the problem in your life story, and then, if you get to my age or beyond, 43 now, at some point, hopefully, you realize that you’re the problem in your life story, and it’s a little bit debilitating to take that on, but it’s also very freeing, because then you don’t have to stand in judgment of others in the same way, and you also have agency to fix it if you don’t need someone else to change. But in 2008 and 9, I was 28, 29 years old, and I had these issues with conflict that I described. I wasn’t able to verbalize conflict and have really difficult conversations with Brian because he was my friend.

Now there’s this whole school of radical candor that talks about, if you’re high on caring but low on conflict, you’re in a bucket that they call ruinous empathy. I was like, “That’s me. I’m the ruinous empathy person.” The problem with ruinous empathy is, in theory, you care about other people, but you care about them so much that you never actually tell them the truth, which is not that caring. So we ended up in a place where my anger was building and building towards Brian for perceived slights. My stresses at the company, as we hired more people and raised more money, were going up. I remember having a call with one of the professors at the GSB. The only reason Bonobos exists, outside of Brian’s innovation, from a financial standpoint, is that two professors backed the company, Joel Peterson and Andy Rachleff. I called Andy one day and I sent him our P&L, and I was like, “We have a major inventory problem. We designed this swimsuits thing. It’s not working.”

Andy, literally, on the call, was like, “No, the problem on your PL is your opex. It’s your operating expenses,” which is actually what Brian was, I felt, criticizing me for, but it wasn’t necessarily criticism. It was challenge.

Because he’s like, “We’re hiring too many people.” And I was convinced that we had to bring on a great VP of engineering from Zappos and that we had to build this tech company. Brian was like, “Eh, it’s kind of a pants company.”

And I was like, “Well, it’s a tech company, and it sells pants.”

We had all these vectors of conflict, but we were unable to resolve it, I think, in retrospect, due to my limitations. Brian’s not perfect, of course, but in our relationship, the friendship was ultimately sublimated to the business discussion, which is the business conversations, which is also common. So I woke up at some point, dealing with a lot of depression. I really disliked Brian. I wasn’t so happy with myself, and that led to a cofounder divorce that happened two years after the company’s formation.

Cyerra Homes: Yeah. Given the conflict you describe and that leading to the cofounder split, is there any advice you would give to GSB students in terms of thinking through how not only to select a cofounder, but also safeguards to put in place in the case —

Andy Dunn: Yeah.

Cyerra Homes: — of a cofounder divorce?

Andy Dunn: Yeah. I think, when it comes to selecting GSB cofounders, don’t. I do think there’s something to be explored, which is that the right cofounder for your company might be at Stanford, but it might not be a GSB student, someone from another school who brings an entirely complementary skill-set. Very likely, you are going to be the CEO of that company, which is cool, because CEO is a fun job, and you won’t have the same kind of complementary skill-sets. If you do insist on founding a company with a Stanford GSB classmate — and I wouldn’t do life any other way; there was no way for me to access what became my life without partnering with Brian, because he was the product innovator and the product genius — it’s worth really thinking about what you’re going to do differently, not at time zero, because that’s pretty straightforward, but like four years later. So, once the company has 40 people, how’s it going to work? Because, when everyone’s in a room, it’s kind of like okay if you have two people running the company, but once you have 40 people, it’s extremely difficult, the co-CEO thing.

I love Ben Horowitz’s comment on co-CEOs when he meets them, which is, “Let me get this straight. It’s more important to optimize for your egos than it is for having a clear decision-maker at the company.” That’s a tough one to respond to. Some people do pull it off, friends of mine, Dave and Neil at Warby Parker. It’s remarkable. But I would hope that someone at the GSB will write a case about how they did it, because it’s so rare.

Cyerra Homes: Yeah.

Andy Dunn: And it’s so much more often the case that there’s someone that leaves before the other person and that that leaving has acrimony attached to it. I would love to teach a class on cofounder divorce, because there is a bunch from the GSB. The founders of StubHub didn’t speak for a decade. There were founders from my class who had a venture together who were married and literally got divorced. I think it’s important, if you’re going to do it, recognize that you are putting the friendship to rest. The friendship ends the day that you go into business together because the partnership eclipses it.

Cyerra Homes: Those are good considerations and great advice. Also, I’m sure we would love to have you come back to the GSB and teach that class. Brian Spaly does end up going on to sell Trunk Club to Nordstrom, so he does have a successful exit of his own. But, Andy, now it’s 2009. You’re alone at the helm of Bonobos as the sole remaining cofounder and CEO. Over the course of the next eight or nine years, you are constantly innovating and trying to figure out how to grow the brand, whether that’s introducing new product categories, figuring out if you should utilize ecommerce in different ways, and then continually innovating. You end up actually revolutionizing the brick-and-mortar shopping experience with Bonobos Guide Shops. Can you tell us a bit about how you were able to innovate and constantly see gaps that others couldn’t at the time?

Andy Dunn: Yeah. I love startups because they’re a collision of fantasy and reality. There’s many genres of human work where you develop ideas and you get to get really passionate about those ideas. There are a few where those ideas are tested and really interrogated and evaluated on a sub-five-year timeframe. One of the most humbling things about being an entrepreneur is that you certainly have enough vision at the beginning to start something. If it exists, you have done that. But the false conclusion that you might reach is that you’re going to be able to do that again and again. So you might convince yourself that you’re really good at vision, and the truth might be that you were really good at the beginning. What I learned was the innovations that were the most profound were not ones that I envisioned, but ones that I noticed.

Just to talk about the stores, we had two fitting rooms that we fabricated in New Jersey that were ostensibly to take around and do different pants parties. One night we rented out a bar and we invited our best customers, and it took 18 people on our team to move these fitting rooms, and it was a massive effort, and we had a bar tab, and everyone drank a lot, and we sold like eight pairs of pants. So it was like, “Well, that wasn’t great.” The traveling fitting rooms concept is not going to be our next thing. So they sat in our lobby, collecting dust. Then, when we were moving from product one to product two, from pants to button-down shirts, thinking about how to eliminate some of the — we called it billowing muffin-top of the shirt, which you saw on none of the gentlemen who walked out. It was a very tailored look. We wanted customers to come in and try it on. We called it the dress shirt alpha. We put it out on Twitter, and Facebook was a not-reviled company at the time, and people came in, and they tried it on, and they were like, “Your dress shirts suck, but can we buy some pants?”

And we’re like, “Well, we don’t sell any pants here.”

It turned into this thing of “Well, can we just try on some pants?” So we had a fit run in navy of every size, and then they would say, “Well, we see the other colors?” and they started transacting. It would be like, “Can we buy some?”

It was like, “Well, we can just do an ecommerce transaction in person.” At the time, we were about a $10 million business, and we started doing a million of sales out of our lobby unintentionally. I remember we had recruited a merchant from J. Crew, because, after Brian left, I had to quickly fill the Brian-sized hole at the company, which was merchandising, design, sourcing and production, supply chain, the creative eye. It was hard. That was the hardest part about that year.

Our VP of merchandising, a guy named Brad Andrews, who’s now up at Nike, a remarkable person, was like, “I kind of like what’s going on inside this little part of our lobby.”

Then we said, “Well, why don’t we try to experiment with putting that at street level?” The unit economics were really interesting, because we didn’t have to stock the store. Having sold watches at Marshall Field’s growing up and worked at Abercrombie & Fitch on the night shift — this was 20 years before the documentary, so don’t judge me, but Abercrombie & Fitch sweaters, when I was at Northwestern, were the rage, and they cost $72 — I still remember this — which I couldn’t afford, so I was like, “I will go fold sweaters at night so I can pretend I’m rich like my classmates at Northwestern.” Very sad. Folding sweaters on the night shift kind of sucks. Sweater after sweater, there’s the board you put in. I remember thinking, “If we could build a store where no one’s doing that, what could we put in instead of the inventory management? We can put in one-to-one service,” which we turned into calling it the Guides. We opened 30 great stores, and then we opened 30 stores where we spent too much money and did need incremental doors in the markets. That was the second innovation in the history of the company, after the selling pants online innovation.

Cyerra Homes: Wow. Well, these innovations helped you grow Bonobos to a company that was doing over $100 million in revenue. It’s 2016.

Andy Dunn: Yeah.

Cyerra Homes: The world’s largest company comes knocking on your door.

Andy Dunn: Yeah.

Cyerra Homes: They end up acquiring Bonobos for $310 million. Many people saw these headlines and were wondering how this acquisition might affect the Bonobos brand.

Andy Dunn: Yeah.

Cyerra Homes: Can you tell us a bit about why an acquisition, and an acquisition by Walmart, was the right path for Bonobos?

Andy Dunn: Yeah. We were right on the cusp of doing a deal with a private equity fund that’s really good in consumer, and there’s two of those globally. That was a joke, guys. But it’s hard. When you start a company, it’s hard to identify private equity investors who you want to work for. It’s a big change. So we figure out a way to barely work for them, which is they were going to buy a 40 percent stake in the company. We were going to maintain the majority as existing investors. They made a really good offer. I went out to dinner at a restaurant called Otto with my CFO and our general counsel, the founder of the firm, and the partner that had worked on it, and they gave me the term sheet at dinner, and I walked home, which was a few blocks to where Manuela and I shared an apartment on Ninth Street. They’d given me a bottle of wine as a gift. I was fumbling with the keys because I was about to show my wife a $300 million offer. As I was fumbling, I dropped the offer and the bottle of wine at the same time. There was this guy named Newton who said that two things will drop at the same rate regardless of size. So the bottle of wine exploded on the offer, and I walked in with an offer that was dripping red, and I was like, “Manuela, I’ve got the blood money.” You know? “We’re selling out.” In truth, I really did like these people and I felt like they got it.

They had this thing they needed to do, which is they needed to put their capital ahead of everyone else’s in the preference stack. I was like, “You guys just got to the party. Why are you the first in line?” We were messing around for weeks and weeks.

Then I heard from someone. “Hey, you should talk to Marc Lore.” Marc had founded Diapers.com and sold it to Amazon. Then he founded something called Jet, and it was wild. He came out of Amazon and was like, “We’re going to beat Amazon,” and the rumor was that he was burning 20 million a month in cash. Then he sold the company to Walmart for 3 billion, which was the only buyer on planet Earth. Who does that?

I walked in to meet Marc in Hoboken, and he was wearing a Vineyard Vines shirt. I was like, “I didn’t walk in here in an effing Amazon T-shirt.” He didn’t care that much about the meeting, but then we sat down and we mind-melded on this concept that the future of commerce might look a little bit like the history of video, which is that, initially, the big platforms were streaming other people’s movies and shows, and eventually that was a race to the bottom on price, and so they would need to develop their own content to win. When Netflix launched House of Cards and Orange Is the New Black, if you go back and look at it, their share price took a hit, because Wall Street was like, “What are you trying to do? Become HBO?”

Cyerra Homes: Mm-hmm.

Andy Dunn: In fact, that turned out to be an astute move. Marc and I mind-melded that I would come in and run this new digital private brand group at Walmart. He said, “You got to meet Doug.” I went down to Soho one night and met this Doug McMillon, an unassuming guy, for dinner with Marc. How do I put it? I came out of the dinner being like, “It would be a privilege to work for this individual.” I fell in professional love, and I’m still in professional love with Doug McMillon. He’s the best leader I’ve ever seen in action, and we should get him up in this chair at some point. I was like, “Whoa, it would be really cool to see this Walmart-Amazon battle play out with — not a front-row seat, but a second or a third-row seat.”

Cyerra Homes: Well, it’s quite impressive that you became a part of the digital transformation of the Fortune 1 company. This obviously was such a big milestone in the life of Bonobos. All throughout you growing and scaling the company, you internally are dealing with so much, so I’m going to pivot now and talk a bit about your bipolar disorder diagnosis. Tell us more about not only the diagnosis in college, but also your initial reaction.

Andy Dunn: Yeah. I was diagnosed when I was a senior in college. I had a few weeks where I kind of took my partying to the next level. I was already drinking a lot, smoking a little bit of pot, but I moved into a bit of ecstasy, and I had my first experience with psilocybin mushrooms, which for me, luckily, was the last. A few weeks later it was the turn of the millennium, so it was 1999 to 2000, and it was a very exciting time, because there was this Y2K narrative about how the digital world was going to melt down, and then there was this “What does the new millennium mean?” As I was using substances and had really fallen in love in a really meaningful way for the first time in my life, I was watching one night a special on people who thought that this was going to be the end of the world or that the Messiah was going to arrive. As my mood escalated, at some point I realized I was arriving. I thought that I was the second coming.

Part of what was so humiliating about mania is that we have these messianic, grandiose delusions. When you come out of it, you’re like, “Ah, everyone now knows that I have this underlying God complex.” It took multiple years later of therapy for my psychiatrist, who I affectionately refer to in the book as Dr. Z, to make me aware that everyone actually has a God complex, and the God complex begins in infancy, because, when you scream, you get milk, and when you cry, you get comforted. This is for the vast majority of infants, not everyone, sadly. We begin our lives as all-powerful beings, and then we slowly part with that reality year by year, at the same time as Disney and Harry Potter incept us with the possibility that we may be orphans who turn out to have superpowers, which is to say that our popular culture is built around the struggling childhood to superpower thing. Most of us discard the idea that we have superpowers, should they ever come up. When you’re psychotic — and one of the things that might help you understand a person in psychosis is that you don’t have the ability to disregard that thought, the irrational thoughts that you might have at any point in the day. “The plane hit some turbulence. We’re all going to die” or “That deer — maybe that’s my daughter who passed on,” like the movie with Frances McDormand. Those kind of thoughts are fantastical, and they’re not discarded by a psychotic person.

So I spent a week as Jesus 2.0, and it was amazing. It was amazing. Being the Messiah when manic is so fun, if you actually believe that’s true, and then it turns out that you’re actually the biggest liability on the planet for everyone around you. I stopped eating. I stopped drinking anything, including water. I stayed up for, we think, four nights in a row. Somehow, through my friends figuring it out, calling my parents, my parents bringing my home, me lecturing my dad on all kinds of stuff — my whole theory was that I was the Messiah, and my message — and some of you may like this message — is that God is actually a woman. It’s like, “Why did men get all this credit throughout history, when women make life?” So I was yelling at my dad about this and I was like, “All your heroes are white guys.”

My dad was a master. He just went full Socrates on me and was like, “Mm-hmm. Mm-hmm.” Then they called over my aunt, the one who delivered me, and they called my uncle, who are both physicians, and they sat on either side of me in the back of a car and took me to hospital, and that happened to be a hospital where I had worked growing up, in the hospital where my mom worked, which just compounded the humiliation afterwards. When the diagnosing physician said, “You have bipolar disorder Type 1,” I remember thinking, “No. No, I don’t. Like, what is that? Two weeks ago I was having fun with my friends. I don’t even know what that means.” Then I went home and I did some learning and found out that the suicide attempt rate is 60 percent, and the suicide rate is 20 percent. When you’re 20 and you’re like, “Well, there’s statistically a 1-in-5 chance I’m going to end my own life, and by the way, this whole mania thing can come back at any point. It could be two weeks or 10 years, and you might do anything in that state, like cut off your ear,” it’s very hard to take that diagnosis on as a 20yearold, and it’s most frequently diagnosed between 18 and 25.

Back to the family norms of communication, very different families, but one thing the cultures did have in common was an abject desire to not speak about mental health. So my diagnosis became a little bit like fight club, which is “We don’t talk about fight club.” We just buried it, and my friends buried it, too. So I internalized that as an unspeakable shame, because what is shame but what is unspeakable. The amazing thing about the human mind is you can actually bury this trauma yourself. I became unaware that these events had transpired and on occasion would remember this thing that happened to me in college. I wasn’t even aware, and then I would remember and have this rising panic and fear. “What, what does that mean? Is that true?” and then push it back down. I lived that way for 16 years and I lived asymptomatic for the first eight, which lulled us, collectively, as a family, into a feeling that perhaps it had been an inaccurate diagnosis. Then, in the Bonobos years, depression kicked in, and ultimately, it came raging back.

Cyerra Homes: Yeah. You mentioned it came raging back. Can you tell us a bit about the episode that I described at the beginning of the interview —

Andy Dunn: Yeah.

Cyerra Homes: — where you found yourself in Bellevue for a week?

Andy Dunn: Yeah. One of the most pernicious things about mania is that it can be triggered by positive life events, having a child, getting married, let’s say selling a company. In my case, it was falling in love with Manuela and coming to the decision that I was going to ask her to marry me. I did it in a very romantic way, when, while manic, I showed her a picture of the ring, which is a great reveal. I was so excited during that time in my life that I kind of replicated the going off the rails of going out a lot, drinking a lot, not sleeping much. Sleep quality is poor if you’re drinking a lot. She left. She was working and splitting time in Beijing at that moment. While she was out, I was just going off the rails, burning the candle at both ends, which wasn’t terribly uncommon for me, but it was more acute.

When she came back, I was off, but she wasn’t quite sure how to process it, because, while I had told her that I’d had this incident in college, I told her what also was true, which was that bipolar disorder is a differential diagnosis, and people aren’t always definitely sure that that’s what it is. It’s both over-diagnosed and under-diagnosed. I had gone to a few mental health professionals in New York when I was dealing with acute depression, and most people were like, “The company that you’re running, that’s a really stressful thing, and you don’t strike me as having this illness.” I had a few people who kind of dismissed it. So she wasn’t really prepared, and it got bad that night. I was lying in bed. I was howling at the moon. I was playing Tupac really loud, and music sounded so good, and she didn’t know what to do, so she called her mom. Her mom came over. Her mom lived in New York.

They were trying to kind of comfort me and manage the situation, and I got up with a start to go to the bathroom. We lived in a little garden apartment where there was kind of a low ceiling, and I hit my head on the ceiling and cracked open and was bleeding, and it hurt really bad. Plus, with the mania, you feel more acutely. We’d had this fight with our landlord, and there was a heating grate that had rats that could come out of it, and I hated our landlord, and so I did something I had wanted to do for a long time, which is I ripped the grate off and threw it, and then I punched a large glass window pane and opened up both of my knuckles here. I can still see the scars as kind of — I take it as a healthy reminder of what’s possible.

Then Manuela came to help me, and I remember seeing the fear in her eyes, and my immediate thought — and this is sort of weird, but I thought she was the alien from Ex Machina, because she kind of is stunningly beautiful and smart and a little bit robotic sometimes, with her intelligence and logic, and so I struck her. Then her mom came out. The felony charge was that I pushed her mom to the ground and I kicked her. They were extremely brave. Manuela got her mom to the bathroom. Her mom called 911. Eight New York police officers showed up within about two minutes. They pinned me to the ground, cuffed me, and took me to the psychiatric emergency room at Bellevue, where I spent a week, unaware of what had happened. As I came down from it, Manuela came to visit every day, which was incredible. I noticed that she had a black eye. It was about day five or six. And I just said, “Did I hit you?”

She said, “You’re kind of a wuss, and it didn’t hurt.”

Then it was like a noose to the sky of shame, to know that that had happened.

Cyerra Homes: Wow. After that episode, how did you think about your bipolar disorder diagnosis? And what do you do today to help to keep it under control [of it]?

Andy Dunn: Yeah. Coming out of the hospital, walking into handcuffs, the next six months were like a hellscape.

Cyerra Homes: Mm-hmm.

Andy Dunn: It was “Was Manuela going to leave me? Was I going to have to step down from my job? Was there going to be PR about it?” I remember being in the Fourth Precinct in New York, a place I never thought I’d be. It was across the street from my favorite restaurant, this Italian restaurant called L’Artusi. I never even noticed that there — this is going to sound funny, but a cute police department across the street, and now I’m in the cell there. The arresting officer is the one booking me. He took my mug shots, and I said, “Officer, are these mug shots going to be online?”

He was like, “Yeah, but, dude, you’re not the founder of Google. You sell pants.” And that was true. That was true, right? If I had had a higher public profile, there probably would have been press because of the mug shots.

It was under my legal name, Andrew Dunn, which is not a thing, and I was in and out of court, and there are court reporters, but it never happened on the PR front. I was supported by the board. Manuela stayed with me, but with condition, which his that I took my medication, saw a doctor, and I became religious about staying healthy. I started seeing a psychiatrist in lower Manhattan twice a week for 45 minutes. I did whatever he said medication-wise, and that included 6 months of experimentation, where I felt suicidal every day. I also knew, because, after the big high is usually a long low, the big high is fast. It’s like a week. The low that follows it can be a half a year or years, depending on the kind of treatment that you have available.

I had great treatment available, which is a fundamental injustice that we have in our society, which is that mental health is reimbursed at a very low rate, and it’s hard to find the right provider. But I got through that, and so now I have a pretty robust system of medication. I still see that doctor twice a week. And sleep is so critical. Sleep is foundational, so I have a sleep report that I send, screenshot of a Fitbit report, a WhatsApp group, and it goes every morning, and so everyone knew yesterday, which is a little bit annoying, because I know my mom worries about it still, that the night before last I slept four hours and 33 minutes, and everyone knew I was coming to give this talk, which I was excited about. So last night was a high-pressure sleep night. I was getting dinner. It was fancy. I treated myself to dinner at Nobu last night, and I was at the bar, and I looked down at the menu and I saw cocktails that looked good, and then I saw the non-alcoholic yuzu thing. It’s like $15, and I had three.

Then I had a friend text. He’s like, “You’re in town. Do you want to meet up?”

I was like, “Oh, I so badly want to meet up,” and I was like, “I can’t. Slept four hours. Big day tomorrow.” I went home and I took the right medication. My doctor and I had a plan, and I had an 8-hour night, and I sent it to my family, and my mom was like, “Good.” It’s humbling to be in this kind of a dynamic, but I know that transparency with my loved ones is a critical part of my health and therefore theirs. So it’s a pretty Olympic regimen at this point.

Cyerra Homes: Yeah. Well, it’s great to hear that you have a process that helps you today. Whether you have bipolar disorder or not, mental hygiene is so important.

Andy Dunn: Yeah.

Cyerra Homes: I know mental health is the focus of your newest venture, Pumpkin Pie.

Andy Dunn: Yeah.

Cyerra Homes: Tell us a little bit more about that.

Andy Dunn: Yeah. Pumpkin Pie started as an idea to find a husband for my mother-in-law, who’s amazing. She’s amazing. How do I put this? She’s very talkative, and boundaries are not her strong suit. She’s got a lot to offer, and you know, she’s lonely. I think she’d be okay with me saying that. We started the company as an idea of “How do we build a dating app for senior citizens?” I had been a founding investor and board member at Hinge, so I got to see the social mobile dating wars play out, and I remember thinking, as I spent time entertaining the idea of helping my grandmother, I should just go with her on the dating apps. So I took over her Match account. Have you ever dated as a 75yearold woman? The guys aren’t the best at writing the profiles, and yet there’s so much knowable at that stage about someone’s life. When you’re 25, so much of your life story is in front of you. When you’re 75, there’s so many choices and experiences you’ve made, how you spent your professional time, whether you got married or not. Did you have kids? It’s this amazing amount of knowable information, and it’s not really there, other than the profile.

So we developed this — it’s kind of a game, where you reveal your personality by opining on polarizing things, and then we hired a computer scientist from this school, and I recruited a GSB friend to be my cofounder. Some lessons die hard. He’s the founder and CEO of Chess.com as his day job, so he’s had an entertaining last couple months. We built the algorithm in the app, and it had zero predictive ability around romantic relationships, but the sample group we sent it out to included people who were platonic friends with each other, and it was highly predictive of platonic friendship. So that’s when we kind of said, “Maybe we could build Tinder, but for platonic friends.” The problem we discovered with that, and the reason it hasn’t been built, is that the two ingredients in a platonic friendship are mutual vulnerability, and continuous, ongoing, unplanned interactions. How do you plan off of an app an unplanned interaction? That’s the conundrum that we’re trying to transcend.

Cyerra Homes: We will stay tuned. Andy, I have one final question for you, before we have a quick lightning round. This is a question that we’re asking all of you from the top speakers this year.

Andy Dunn: Yeah.

Cyerra Homes: Principled leadership is paramount at the GSB. What do you view as your role in leading with responsibility to not just your organization, but also society at large?

Andy Dunn: Yeah. I love Ken Chenault, who ran American Express, one of the great black CEOs and pioneers. He ran AmEx through many things, he was a phenomenal CEO, and also through 9/11, and coming out of 9/11, where some 50 American Express employees perished. He came out of that at some point and said that the job of a leader is just twofold. It’s two bullets, two words each. Create hope. Define reality. I love that. I think creating hope and defining reality are almost impossible to do at the same time, because reality is scary and bleak, and then hope is something that we need to magnetize people to follow us, and we need to lead them somewhere winsome. I look at where we are societally, and hope is hard at the moment. Hope is hard from a climate standpoint. Hope is hard from a justice standpoint, whether racial, gender, sexuality, otherwise. Hope is hard from a political divisiveness standpoint. There’s a lot to not be hopeful about, and yet your job is to be hopeful and to convince other people to be hopeful, too, the people who will be following you in whatever you do next. Then your job is also to not let those people down by not being realistic about what you’re trying to do. Doing those things together, it takes a rare human that can do both of those things, and many of those rare humans are right here.

Cyerra Homes: Well, thank you. That’s a great note to end on. We’ll do a quick lightning round now, just in the interests of time. This is a View from the Top tradition. So, Andy, I’ll ask you four questions.

Andy Dunn: Okay.

Cyerra Homes: Please say whatever comes to mind first.

Andy Dunn: Okay. I’m ready.

Cyerra Homes: All right.

Andy Dunn: It’s like being at the doctor’s office.

Cyerra Homes: Yeah. The first one is best piece of advice ever received.

Andy Dunn: You catch more flies with honey.

Cyerra Homes: Nice. Next time the Cubs will win the World Series.

Andy Dunn: 2034.

Cyerra Homes: Oh, wow. Okay. Most memorable GSB class.

Andy Dunn: Interpersonal dynamics.

Cyerra Homes: Yeah. Fan favorite. Favorite Bonobos pants print.

Andy Dunn: The Pink Panthers, before the trademark shut us down.

Cyerra Homes: Ah. Wish we had a model wearing that today. Andy, you didn’t give your talk here on campus when you were a GSB student, but thank you so much for coming back and sharing your story today.

Andy Dunn: Yeah. Thank you.

Cyerra Homes: Yeah.

Andy Dunn: [Thanks].

Cyerra Homes: Thank you so much, Andrew.

Andy Dunn: Thank you.

Cyerra Homes: Thank you.

Andy Dunn: Thank you so much.

Cyerra Homes: Yeah.

Andy Dunn: Thank you.

Cyerra Homes: You’ve been listening to View From The Top, the podcast, a production of Stanford Graduate School of Business. This interview was conducted by me, Cyerra Holmes of the MBA Class of 2023. Lily Sloane composed our theme music and Michel Reilly produced this episode. You can find more episodes of this podcast at our website gsb.stanford.edu. Follow us on social media @stanfordgsb.