Why Andy Dunn walked away from everything but one thing

Andy Dunn: father, entrepreneur, author, brand builder and a major advocate for mental health awareness.

You might also know him as “Andy” from Monica + Andy, the organic baby clothing company where he serves as Chairman of the Board.

Back in 2007, Andy co-founded Bonobos, one of the first digitally native menswear brands, helping to pioneer what we now call direct-to-consumer.

After selling Bonobos to Walmart, he spent two and a half years as SVP of Digital Consumer Brands before stepping away to figure out what came next.

What followed was Burn Rate, his powerful memoir about his experience with bipolar disorder - and the intense highs and lows of building Bonobos.

In our interview, we don’t rehash the Bonobos story - it’s well told in his book.

Instead, we pick up after the exit: what it was like working inside the world’s largest company, becoming a parent, navigating identity and building again…this time, with intention.

Allison: Andy, thank you so much for joining me here today.

Andy: Glad to be here. Thanks for having me.

Allison: First of all, I'll start by saying I'm very excited to finally meet you. We have a few mutual connections and so I've heard a lot through them. But also, if I have to be honest, I'm most excited because I read your book. I pre-ordered it, it showed up at my house. I think I, so I'm a huge reader. I read the whole thing in like, I don't know, 10 hours, 20 hours, however fast you can read a book cover to cover. And then I gave it to my husband, who is not a reader. He probably reads like three books a year.

He tore through it within a day. And so when I was preparing for this interview, I was going around looking for it because I was like, I want to reread certain parts of it because I just loved it. And of course, I can't find it because I gave it to I don't even know who because I was handing it around to all my friends. So I am a huge fan of your book. And because of that, I want to encourage people to buy the book, read the book. And so we're not going to even dive into what you talk about in there around the Bonobos piece, although I do want to touch on some of the themes around mental health that you mentioned in the book.

To kick us off, I'd love to talk about what happened after you sold Bonobos to Walmart. During that period of time where you've sold the company, but you haven't earned out, so you're now at Walmart, you started your own company, now you're working at the largest company in the world. What was that experience like? And how, like explain this sort of mentality and the way that you were handling that experience, because I believe from what I learned in your book, that was also the period of time that you were really getting serious about your bipolar disorder and figuring out what is the way to sort of manage your life. But tell me more about what that phase of your life was like.

Andy: It was oddly exciting. I think it was something new after 10 years of, of building in founder mode. As you know, it's, it's a lot, it's a lot to carry the company on your back. Obviously as you hire a great team, you're carrying it together, but you're also carrying it on your back. I felt that weight over time of hundreds of employees and having raised over a hundred million dollars.

And at some point I wanted something more stable, at least for a period of time. And I can remember meeting the CEO of Walmart for dinner before they even made us an offer. And he said, Andy, why do you want to do this? Why would you do this? And I said, Doug, Doug McMillan, said, Doug, I need a job. And he said, well, you have a job. And I said, founder isn't a job.

I want to be a part of something where I don't have to worry about making payroll. And I was pretty sure that Walmart was going to be able to make payroll regardless of what I did. part of it was the exhaustion, the desire to feel like we won, like the team won. We built something enduring a value to get investors their money back and to personally make money. Right. One of the reasons why entrepreneurs do what they do is to build wealth. And at some point, you know, you have moments of, it going to work or not? And gosh, I spent all these years and I'm not going to make a penny from it, let alone my management team and the team. So that was, it was exciting to feel that relief. I remember when the deal was closing, I called my mom and she said, congratulations, you did it. And I said, no, mom, we did it.

And she said, how do you feel? And I couldn't talk. just was tears were streaming down my face. Cause it was like a decade of accumulated stress coming out. So I couldn't even respond. And she goes, guess where I am. I said, where? She said, I'm at Walmart. She was at the Walmart on Broadway. So it was a relief. And then it was a whole host of new learnings, you know, which we can get into of what it's actually like to be an employee rather than a founder. It's quite different.

Allison: And I would love to hear what that's like, because I'm in the thick of the founder. mean, I'm five years in myself and totally resonate with like the carrying things on your back. What were the things that you were like most surprised that you actually liked now that you were an employee? Because I feel like with founders, we think, you just always have to build. You're always going to be in founder mode. But I'm sure that there were, in addition to feeling relief, there were also other things that you really enjoyed about being part of a larger ecosystem.

Andy: One thing that comes to mind is there is a joy to serving others. I think when you're building your own company, is a lot of it is about you and your creation and everyone works for you. And the board came together because of you and the investors invested in you. You join a company all of a sudden. And it's not about you. It's about someone else or it's about the mission of that company.

And Walmart's mission, save money, live better. We're going to decrease the cost of basic goods. That's going to increase the standard of living. It's such a strong mission when you get there, you know, save money, live better. And just to kind of study that and say, how did this culture get so strong? What did Sam Walton do in getting to know his kids and his grandkids? I think that was fun to belong to something bigger than something that I had created. And now as a parent, I feel that same joy. It's nice to be in service of someone or something that feels bigger than what you are building. And then I think it helps to work for people you admire. And I got both sides of it at Walmart. I got to work for Mark Laurie, who was my boss and who's an amazing entrepreneur, owns the T Wolves and the Lynx and he's got a new company called wonder and he's a billionaire. And I just looked up to him and in every day I felt, this is a better entrepreneur than I've ever been. And I get to work for him and learn and soak it in for the next one. So I could be more like him. I wanted to be like him. I still do. And so that's cool to look up to someone. felt like kind of like older brother energy. And I felt the same way about Doug. 

SoI was in sponge mode and I realized how fun it is if you work for people that you respect and admire and how much you can learn from them.

Allison: I do think it's interesting that you're working for Mark because while the picture I painted in my head was, you're working for this slow moving behemoth of a company, but you were actually working with one of the most incredible serial entrepreneurs. What are like some of the more interesting things that you learned from him or maybe even like the things that you learned from him that you think about most now that you're back in founder mode?

Andy: Yeah, I thought I was delusional as a founder and as a leader until I started working for Mark. And I was like, the scale of this man's delusions about the future is amazing. It's enormous. It's like, we're going to beat Amazon. And whether he believed that or not, his conviction was so strong and he had a strategy for it. And it was supported by math. Mark is really good at math. So he would explain, look, we're gonna leverage this Walmart super center. We are 10 miles from 90 % of America. We're gonna beat him in grocery where we're number one. And if we do that and hear the other pillars of the strategy, we can actually win. And what I discovered was you start to believe someone. And I remembered it from Bonobos. I remember people being like, do we believe him? Is this really gonna, are we really gonna beat J. Crew one day? Which is what we talked about when we were two million of sales.

And so Mark taught me to dream even bigger than I'd ever allowed myself. And now I'm applying that to what we're doing at pie.

Allison: And are you finagling some way to stay in touch with him and be involved in some ways? Or are you like, we had that experience, I learned a lot, and now I'm just laser focused on this?

Andy: Definitely have finagled. I try to be surgical with outreach. I sort of learn from people that are in his orbit, probably like a quarterly text message, an annual five minute phone call, and then maybe once a year making a bid for dinner or something. And Mark always picks up the phone. He always, like I could call him right now and there'd be a decent chance he would pick up and be like, hey, what's up? And he has this view of don't calendar it, just call. Because most things that we think we might need a half an hour, can we set up 20 minutes? Most of the time you can do it in like a minute or two, right?

Allison: Yeah, interesting. But yet you didn't stay at Walmart. You were only there, I assume, through your earn out, regardless, you were there two and a half to three years. So how did you make, like, what was that thought process like? Because you left Walmart, it was the beginning of the pandemic, you were newly married, then you welcome your son. Walk me through what happened next.‍

Andy: Yeah, I wanted to get, I actually wanted to stay at Walmart. I did, there was a job, the chief marketing officer role was open and I wanted it and I got passed over for it. And so I also felt the bummer of like, you believe you can do something and you want to move to the next level. And then I didn't get it. So I developed some humility from wait, well, why didn't I get it? And I learned a lot about, you know, I just wasn't an effective corporate executive.

Allison: Say more, what does that mean? Like what does it take?

Andy: Well, I think part of it is advice I got from Alexa Van Tobel. Alexa built a company called LearnVest and she sold it to Northwestern Mutual. Now she has a venture fund called Inspired. And I was maybe two years into my time at Walmart and she was in Bentonville and we sat down for coffee because I spent a lot of time down there. I really like Bentonville in Northwest Arkansas. I think it's a really compelling place. It's growing so quickly.

Allison: Yeah, I've met her. Love her. Yeah.

Andy: It's also very intellectually stimulating if you live in New York, which is one of the 10 % most blue places in terms of our politics. And then Northwest Arkansas's top test, Decile Red. So I just had a broader aperture for what was happening in America. And mind you, this was 2017 to 2020. you can kind of picture what was going on in the country then. So Alexis hits me down and I said, I'm not doing great here. Like I'm trying to get things done.

I'm trying to get acquisitions done, which was part of my mandate. It's not happening. Trying to get some things done on the diversity inclusion front. I don't feel like I'm making that much progress there." And she said, I know what your problem is. She said, as founders, our jobs are to be big. We're trying to get attention. We're trying to attract talent. We're trying to raise capital. We're trying to matter to the market. We're trying to do partnerships. We're trying to sell.

She says it at a company when you come in as a founder who everyone knows you got paid in a big way from the money that they're helping make, right? From the profit that they're generating. There's a little bit of a bullseye on your back, right? Like you're not coming, you're kind of coming in as a, who does he think he is? And so what you need to do is put your head down, get your stuff done and get small, like get small. And I was like, oops, I didn't do that the last two years. So I think something like discretion. So as an employee, discretion is critical. What you say to who and when really matters. As a founder, you say whatever you want, whenever you want, you can cause organizational chaos.

But at the end of the day, you're the founder. So what's going to happen to you as an employee? If someone gets angry with you, they can box you out. You know, so I remember watching Game of Thrones for the first time while I was in Bentonville being like, this is how it works. And it's not Walmart. It's corporate America. It's large organizations everywhere. Tribalism, trust, all these things that are in our nature when we organize in large groups, if you're not the chief, it's different. You can sort of undermine yourself if you're not deploying a lot of discretion and self-awareness. And I remember one executive sat me down and she goes, you know, Andy, everyone's not your friend. I was like, what do you mean? She was like, everyone's not your friend. You know, and I think

I think that's true in life, but as a founder, can delude yourself into thinking everyone likes you and everyone doesn't like you in this world. It's just that as a CEO, you don't know, as a CEO, getting, you're getting played. And that was another realization of like, I was getting like played and manipulated back by all kinds of people who were really thinking strategically about like, how do we approach Andy on this?

And then once you're an employee, it's like, I was an SVP, which is cool. had a thousand people in my organization, but Walmart probably has a hundred SVPs. So like Walmart didn't need me and I wish I could go back, take what I now know and I would show up differently. I would be less loud. I would work way harder to build bridges. You know, there's just a lot. And I did work at that, right? But you got to bring so much humility to being an employee. It's different.

Allison: I wonder if there's an aspect of speed also where in startups like making mistakes and moving really fast and you don't need to be perfect and or did that translate in Walmart? 

Andy: No, we were doing that because of Mark. Yeah. I don't think I had a typical experience of being an entrepreneur post acquisition. I was a part of a business unit that was brought in, led by a billionaire entrepreneur to move quickly and break stuff. So it wasn't…

Allison: Yeah. Okay. Hence why you wanted to stay. Because you were like, this is...

Andy: Well, yeah, and also stuff like that doesn't mean that everything you want to do is going to get done. And I remember one time I emailed Doug being like, oh, that was really demoralizing. And because I was working for six months on an acquisition and it just was like, no, we're not doing it. Like I took it to the exec team and the board and they were like, no. And I was demoralized. It was six months, right? That's forever. And Mark stopped by my desk and he's like, demoralized, huh?

I thought it was like, what do you mean? He was like, it's like, that's a big word for not getting a deal done. And so you also got to take it a little bit less personally and be okay, you know, with what I would tell people, which is, hey, you got to disagree and commit here, we're going to surface all the opinions. But then if you don't agree, we got to disagree and commit. But then when you actually have to be the person disagreeing and committing. That's different. And so I think I would have gotten less wrapped up in what I wanted to do versus what happened and just been like, okay, that deal didn't get done. That sucks, but let's just move on.

Allison: Yeah. So then once you left Walmart, how did you decide what to do next? I mean, you probably didn't have to find something to make money. Like you're in this really unique position where you, it's almost like could do anything and therefore, I don't know. I'm just so curious how you thought about what you do next and did becoming a father change what you wanted to do next?

Andy: I drove my wife nuts because every day I was like, should I start another company or become a venture capitalist? That was the choice that I felt. I felt like I wanted to stay in startups, but should I build or should I back people? Because I'd gotten a chance to make a bunch of angel investments and had a little side hustle seed fund. I'd had it for years and I liked that too. I liked backing other people. Candidly, I think it's much easier.

I don't think it's easier to be good at it. It's hard to be good at venture. Most, I think only the top quartile of firms outperform the S &P, but it's easy to do. It's hard to be good, but it's easy to do because you're not the one doing it. You're the one backing the people doing it. And I'm not trying to diminish what venture capitalists do. There are some, not most, but some that are quite good. many of they work quite hard, but it's just a different kind of stress when you're diversified, right? It's not like if this one thing doesn't work, whereas with an entrepreneur, you're single-threaded. Like what you're doing, all your eggs are in that basket. So I tried to do both and I kind of went back and forth and I started this experiment, science experiment called pumpkin pie. So it was called at the time and I made a lot of angel investments. Like I started making more, know, I was making one a week. I was really going for it.

And then I had this awesome moment of, know what, I need to go back and look at all the investments I've made. And what I discovered was I wasn't that good at it. I say yes a lot. I want to believe in people. Whereas being a good investor is like, you're saying no 99 % of the time. And that's not in my nature. It's like, I can picture how the person could make it work. And this is twisted.

But I want them to believe that I believe in them. Because I think if they don't feel like I believe in them, am I going to somehow bum them out? Which is funny because I know from having been rejected a thousand times, entrepreneurs are resilient and they're going to move on and figure it out. So I went and I looked at our fund, Red Swan, that I'd done with partners. And I looked at all the deals that had been done and who led them. And I was like, my deals are not that good.

I've got some great companies like Hinge, for example, but Hinge wasn't a great investment from a venture standpoint because Match got it for a song. Great company, but there's a difference between being able to get into deals and having great access and being a good picker of the best one. So that helped nudge me towards the path of building something. And also I had a chance to really reflect on my journey with Bipolar and how that intersected with being an entrepreneur and just how much we had learned and I had learned as a family and as an individual about how you navigate mental illness and how you navigate the intersection of building something. And I, so I spoke to my wife about that and I said, Hey, would you ever endorse the idea of us telling the real story of what happened? I remembered this day where my wife has great taste in everything but men.

And so we have a mid-century modern Brazilian vibe in our home. And the one we had in New York was featured in Architectural Digest. And it's just like, really? It's just like.

Allison: Was just reading it. I was just reading that article. Beautiful photos.

Andy: Yeah, it was just like stunning in the picture of us with the baby on the balcony and the flowers on the table. And I was like, we don't look like this. Like our house is never this, we don't have fresh flowers on the table. No, I mean, it just was, it was the photoshopped airbrushed version of it. And of course, like beautiful home, we're so lucky for having gotten to sell a lot of pants and winnings from Manuela's Ventures as an entrepreneur as well. And I guess that day I'd always chase that kind of status, not status in the entrepreneurial community, which I had accumulated, but status as like cool and stylish and from that side of things, know, the fashion side, architectural digest being about taste and all that. And then I remember the post got like 200,000 likes or something, you know.

And I felt like such a fraud that day. I just felt like really, I felt the opposite of how I thought. I felt sick. Like people think this is our lives and we've just been through hell. Like literally a year ago I was in jail and our lives were falling apart. And I asked Manuela that day, said, can we tell the truth? And she was like, F yeah.

And that led to the journey of writing Burn Rate. So it was a spirited time because it was writing a book and raising a new venture fund and starting a company. And then we had a baby and we moved. It always can lead too much. I was doing way too much. And I've had to unwind that now to get focused again and to be a good parent and a decent husband. You can't have a job in three side hustles. You can't be writing books and starting companies and making investments. So that's been a little bit of an out of body experience for me for the first time in my career to be just like laser focused on one thing.

Allison: So are you now, would you say laser focused on pie?

Andy: Yeah, that's it. That's all I do. So I've had to, you know, I've had to say no and just step aside from a lot of things. So for example, even just being on the board of a not-for-profit, I feel so bad, but I got to go, you know, and telling the founder, hey, I can't help you anymore. Like, I got to go. And so I've had to two of those or going to my partners on the investing side and saying, you know, I'm happy to be an investor in you and I'll forward all of my deal flow to you, but I can't dig in. know, and so as Red Swan 4 is now full, you know, close to fully invested stepping back there. I get a lot of emails, hey, can you talk about this or let me show you my company or I have bipolar and can you have 20 minutes? And I've just learned to say, I'm so sorry, I wish I had time. I have like my one-liner, it says I'm heads down building pie and focused on my young family. And I send, you know, between three to five emails like that a day, whereas before I would have been tempted. Just like, yeah, let's set up 15 minutes, right? And every entrepreneur I met, felt like, got to take a look at this in case it's good for the fund or what if I want to invest in it? Political giving, I did a lot of political giving after the Walmart deal and I would talk to Congress people and senators and governors. And I got a kick out of like that kind of, I'm gonna talk to the governor of Alaska today or something. By the way, it's Alaska. It's not like I never talked to, but I've set that down too. And there's a bunch of reasons I've set that down, but it's been, it's little things. It's like death by 10 to 20 minute distraction, and the context switching, and it's like…

And my wife helped me with this. am choosing to not spend those 10 minutes with our son. Like by definition, it is zero suck. So am going to spend 10 minutes with my son who already has parents who are working really hard. So it's not like his cup is overflowing with time with us. Or am I going to spend that 10 minutes helping an entrepreneur who I'm probably never going to meet, right? And who, if I invest in, it's probably not even going to be a good investment. And that, that it's so clarifying. And by the way, it's still, it's still a shit show. Like our lives are still a shit show, even with clarifying down to one thing. And then the last thing I'd say real quick, cause I just noticed that the best entrepreneurs only do one thing. Like we did a good job with Bonobos. I'm proud of it. But from spending time with Mark Lurie or Ev Williams, who's a big investor in pie, they just do one thing.

They're not dabbling. They're not investors and entrepreneurs. They're, they pick.

Allison:  It's so interesting how you talk about also everything that you say yes to, you're saying no to your son. Because I imagine there's also this like really powerful improvement in how you show up for pie as well. Because if you didn't have that pressure of your son, you would probably be saying yes to all of these other things. And that's also taking time away from the one thing that you should be working on in your like, you know, nine to five in quotes, so to speak.

Andy: So much to say about that. So much to say, for example, in Bonobos, I was really leaned into external opportunities whenever I had one. So if I could go on a trip to go sit with the Denim Conference for Women's Wear Daily in LA, or if I were invited to visit a venture capital firm, that probably was never going to invest in there in London, or if I could go talk to someone in New York. I was not at the company as a core routine. I was split. I was like 50-50 external, internal. And then when I was at Walmart, I realized like Mark and Doug were just internal. They were internal or they were on CNBC for like an hour. There wasn't this accumulation of status through external stuff.

They were with the team and I benefited from it. I loved it. I loved being around them. So I vowed to be really internal at my next company to only take external stuff. If I had to like even this podcast for me is I chose it consciously and intentionally because no, because of

Allison: Yeah. Thank you. As you're talking about this, I'm like, I owe some people thank you notes.

Andy: No, I chose it very intentionally and I hate to sound like it the way that this sounds, but I turned down nine out of 10 podcasts now because I just, don't, my story's out there. Like candidly, people can find their way to it. So it's really just like an ego boost. And that's a similar kind of a trade of I'm choosing to spend an hour externally rather than, you know, being in a meeting, talking about product or prepping for the senior leadership team meeting that's coming up. I love the Claire. It's it's nice to be 46 years old. Like I like being old. I like being older. I like being older and less insecure about who I am and more clear about my priorities. And it's just easier to have family and pie and not anything else. And then within pie to be like, build it with the team. Cause no meetings I'm going to take externally right now are going to help us do what we need to do to find product market fit and build, you know, build a great app.

Allison: Right. And you're clarifying something for me as well, because I'm 41. I have three very young children and started the business as a mom. And so I find myself all the time thinking if I were not a mom, I would not have turned down that party that Glamour hosted in DC with all these politicians that I love to hear about. But it had...

Absolutely nothing to do. I mean, a little bit to do with our business, but you're right. There's all these cool things that when you're a founder, you get asked to do that I tell myself, it's brand. And now I'm turning them down because I just can't go. But I don't have the comparison or I guess I didn't think of it as that's actually like good. Like I only think about, this would be such so different if I didn't have children almost in like a negative way for all those cool, flashy, fun things that I don't get to do.

Andy: 100%. And I remember talking to one of my board members at Bonobos about this because he was aware that I was spending a lot of time with other entrepreneurs and was investing as a side hobby and had a venture fund. And he's this French guy, amazing, know, very successful. And he would say, why do you spend so much time with other entrepreneurs? What about your team?

And I said, and I got extremely defensive because I used to get very defensive in general. And I've learned to just get curious when people say something like that. Now I know, now I say, say more. That's my like default for when I feel defensive is just take a beat and learn even more about why that person is saying it. And he was like, no, I just have noticed best entrepreneurs don't spend time with other entrepreneurs spend time with their team.

And I said, Charles, look, I'm 60 hours a week. And so if I'm taking breakfasts and meeting someone at night for a drink, why do you care? Like you have a family and you spend time in the evenings with them. Would I ever tell you not to spend time? And you would think I just like checkmate won the argument, right? And he goes, no, but I just heard this. You can't get married then. It was like a brilliant comment because now that I am married and am a parent,

He was right. Like you gotta pick, right? And there's sort of the list that people say of like, you have your work, you have your family. If you do, you have your friends, you have your hobbies and you have like exercising and taking care of yourself and you get to pick two of the five. And I think there's some real wisdom in that, which, and I'm trying to like squeeze in the exercise, but it is hard to do more than two.

And things like friendship and hobbies do go to the side, which is part of why, you know, I'm building what I'm building now because I don't have a lot of time to go find friends. I have like a very small amount of time to have platonic friendship in my life. And, know, how do you do that at our stage when you move to a new city?

Allison: So this is a perfect, and I know we are over time and I know your time is precious. I want you to talk a little bit about pie. Why is this the thing that you chose to do? You choose to focus on one thing. Why is it this? And what is next? And maybe even just like give a quick description, cause I could describe it, but you'll do a better job than I will.

Andy: Yeah, pie's pretty simple. Our mission is to defeat social isolation and help people make friends. And the reason for it and what I've learned about entrepreneurship is it's kind of hard to solve a problem that you personally don't have. And this was a problem that I had very acutely when we relocated from New York City to Chicago three years ago. And what I realized was first it's hard to acknowledge that you don't have friends.

Because my whole life I just, you know, I've been lucky and been blessed. I've had friends, you know, you have friends growing up in school and then maybe if you're lucky you go to college, more friends, then you go to a job, more friends, and then you go out, you know. And New York City, I've been there 15 years. My whole world was there, like all the people that I spent time with, all the Bonobos people, my single days, my married days, our couple friends. So it was, my cup ran over.

There was always something to do. There was always an invitation. There was always people that wanted to get together. I came to Chicago and I just was like, oh, this is great. My family's here. My sister's here. My parents are here. I'm moving with my own family. And then I was talking to my psychiatrist one day. I was a little down and he was like, hey, just question for you. When's the last time you had dinner with a man?

And I was like, well, what do you mean a man? He's like, you when's the last time you had dinner with another male? I'm like, my dad? He's like, no, not your dad. And I thought about it and I was like, it's been, exactly, I was like, it's been over, it's been three years because of the pandemic and the move. And I just sort of told myself I didn't need that. And that led me on the journey of like, well, wait, how do you make a friend if you don't have time?

Allison: Non-family member. You're like my brother-in-law?

Andy: Like how does a 46 year old with a four year old child and a remote at that time, remote life entirely make friends? And that was this, that is what brought us towards what we're doing now at pie is trying to solve that problem.

Allison: Do you feel like the highs are still as high now that you're doing this another time and you've had so much success before?

Andy: No, no way. The highs at Bonobos were too high. You know, it was, we're going to beat Amazon tomorrow, right? Like it was just flashes of what's called hypomania, know, delusions of grandeur and being so sure about my ideas and being distractible and irritable and talking too fast, making decisions too quickly, hiring someone who I really like right away. Some of which I still do, by the way, like some of that is still, it's still alive in me, but it's not the volume isn't as high. The volume is like 70 or 80 % on a really good day.

Whereas before sometimes it would be 90%, you know, or 95. And then, you know, I'd be sleeping maybe three to four hours a night and I was drinking a lot, all that. And now I'm pretty religious about averaging at least seven hours. And so I'm just more calm. Like I got a note an hour ago from someone on my team who said, hey, something's been bothering me and here's what it is. And what I would have done at Bonobos is I would have pushed back.

And actually said, this is like your fault and here's why. And I kind of think 80 % of it is on this individual. But she's also open to that conversation if I approach it in a way that is bilaterally curious and free from judgment or a sense of righteousness. And so I just wrote her back and I was like, totally hear that. And I can see that dynamic.

Do you want to talk about it at our senior leadership meeting with everyone or do you want to have a quick sidebar later today? And it was just so easy. Whereas before I would have gotten really riled up. Just really riled up inside. So it's nice to be like, I'm not like steady yetty, but my zone now is I can get a tiny bit depressed and I can get pretty excited. Whereas before I used to be way too excitable and really depressed, or really depressed depending on the season of the situation.

Allison: And I feel like in your book, you talked a lot. Now I'm not remembering if you explicitly said this or if this is my interpretation of you used those periods of manic periods to really drive a lot of innovation and get a lot done. Does it feel weird to now not have that? Like, how do you figure out a new way of working without that? I don't know, I just feel like so many people...look back at the way that they know how to work and you think that that will get you to success. So how do you find a new way? Or is that not even a question you ask yourself?

Andy: No, no, it's a great, I definitely asked myself the question. It's cool. It's actually better because I have the grandiose ideas, but I approach them a little bit differently. Like Epinobos, would have an idea and just go start doing it. And now what I've learned is, no, I got to bring people along. And by the way, they made it think it's a dumb idea and I need to make space for that dynamic. Like last week we had a leadership team offsite and we did a whole exercise on our strategy.

And I told my team, was like, kind of think I know what I want to do. So what do I do here? Like, do we have the meeting? Because I feel like it's sort of Kabuki theater. You know, like I don't want to pretend. and it was sort of, let's have the conversation because even if we decide to go that route, or you decide, like we talk and you decide, we'll be more committed to it if we had the conversation.

And I was like, all right, I feel like we'll be done with this part of the meeting in like 10 minutes. And then it was three hours and it was a really good discussion. Because by the way, I'm not the smartest person in the room. have the most power, but what a really powerful person does is they know they're not the smartest person in the room. And you surface ideas from other people and you consider them. You get clear on whether it's a consultative decision or a consensus driven decision.

It's important to say, look, I'm going to make this call. So let's have the discussion. First is like, I think we all need to be aligned on this. Those are two different kinds of meetings. Just feels so much healthier to have a different process. The same grandeur, the same energy underneath, but just so more chill about it.

Allison: We are way over time than what I told you I was gonna get you out of here. I had a whole like, you know, rapid fire at the end, which I'm not gonna put you through. Okay.

Andy: I'm okay personally. I'm okay personally through two o'clock, but I know you do these as 30 minutes. I don't know how you edit them. So I'll leave it to you to decide how much time we take.

Allison: I mean, if you'll let me keep going, I'm going to keep going. I almost feel bad that I didn't ask you about Bonobos, but I'm glad you said your story's out there so people can go read the book. I mean, the book is phenomenal. And so I'm like, I read all that. I had other questions more about pie. I guess like, and maybe let's talk a little bit about fatherhood. When you were writing your book, did you already have your son because I couldn't figure that out when I was researching you what the timeline was.

Andy: I was aware he would be reading it one day and that did influence a couple of things I didn't put in. If you read the book, if you read this book, it doesn't really feel like I left anything out, but I left a couple of things out. I remember reading Greenlights by Matthew McConaughey and he kind of doesn't kiss and towel in the book. And that guy clearly had a pretty good run. You know what I mean?

Allison: I was gonna ask you that. Yeah.

Andy: Like he's probably got some good stories from his bachelor days and he just doesn't go there. And so I thought, you there's a lot to leave out here. And also out of respect for other people who didn't, even though I disguised most people where I needed to, I did leave some things out. In terms of writing it, I was working on it while Manuela was pregnant. And he was born during it, during the process, which was kind of cool because I remember I was so worried about becoming manic due to his birth. Because the problem with mania is, and I mentioned this in the book, like I think the pernicious thing about it is it can come from a positive life event. think it's the Japanese who say mania is the flight from depression, that depression is so debilitating that when you come out of it, you want to run as quickly as you can to never go back. And if you're not well, the depression is really severe, which tends to mean the highs are equally severe.

And I was just, I mean, as we all know a dad's job at the time of the birth of a child is to be the most solid, right? Because the baby's pretty new to the party and mom is going through so much. I just like, the last thing I want to be is a liability. Like, Andy's headed to the psych ward while, you know, my baby's down the, just picturing it from Manuela's standpoint of.

So I was really dialed on making sure my regimen was good. know, luckily I'd been on that journey for three years when he was born. And then we could get into a bunch of stuff, I think. I always wondered, could I be a parent? Would I pass this on, this terrible illness? It's genetically heritable. How was I gonna be a dad when I was depressed? Like I knew that depression was a part of my cyclicality.

God forbid, what if I'm in psychosis? Am I gonna hurt him? So it took a lot of work to be like, no, I'm gonna be pretty good at this. Like if something unexpected happens, okay, but it's not gonna be this, because this I can expect. You know what I mean? Like you don't get surprised by tornadoes if you live in Kansas. Because you know what I mean? 

Bipolar is a tornado and I live in Kansas. So if it's an earthquake, I guess there's earthquakes in the Midwest sometimes. Like, okay, let's let that be the surprise, but no, not the tornado.

Allison: That's a great way to put it. I had to finish the sentence that I had written down. Becoming a dad made me realize that I am terrible at blank. Something that you maybe thought you were really good at before and it humbled you.

Andy: My God, I have such a long list. I'm trying to figure out which one is the most incriminating. The two things that come to mind are self-control and empathy, which are pretty important to parenting. But like one thing I struggle with now is my phone addiction. And so I'll find myself, like just yesterday, we had dinner, it was just me and him. 

He ran to his room to play and I just was like, I wanna play a quick game of Blitz Chess on my phone. I have like four minutes before he's gonna call for me. Or I'm just gonna check email quick or check Slack. And of course I do this all the time, right? Like what parent doesn't check their phone, you know, when they have a minute. And of course like checking one's phone when you are in front of your kid. And I remember thinking like, I'm never gonna sit on my phone while I'm with him. Like I'm never gonna educate him that like I care more about what's happening here.

You know, we're lucky we have good childcare and everything. And so I'm gonna shield him from that. And then when I'm with him, I'm gonna be present. But I actually find it like very difficult to be present. And for example, he'll say like, dad, play with me, play with me. And I'll be in the room with him and I'll be like watching him. I'm responsible, but like I'll just be sitting there and like daydreaming.

Allison: Yes, my sister and I talk about it all the time. Yeah.

Andy: And I like to sit on a chair in his room and watch him and he'll be like, dad, come here and play with me. So it was just an interesting example that this morning I had the self control to leave my phone by my nightstand. didn't check it before I got, so I didn't get the train going. Like I didn't check what was on it. Cause why do I need to check it at six if I can check it at eight. And I sat with him and we did magnet tiles on the kitchen table while we had breakfast. Of course, he didn't want the cottage cheese and toast I made him. So we solved that problem. But then he was I was like, what do want me to make? He was like a haunted house. So while he made the whatever I made the haunted house. And it just it was so special, right? You know, he really enjoyed the haunted house, you know, it made a difference in his day. Like that was a really good part of his day. For me, it was kind of a part of my day I didn't enjoy. Like I didn't want to make the haunted house.

But then you lose yourself and you remember that interplay is fun. Like actually, magnetiles are kind of fun, but it's hard for me to commit to the moment. It's hard for me to just like commit to being present. I don't want to. I want to be in my brain. I want to think about pie. I don't want to play. But being a dad isn't thinking about Pi. It's about playing. And I see that come naturally to a lot of other parents or I feel like it does. I'm so envious. Like I have a number of my friends like, my friends from college, I feel like they're all better dads, which is also a bad narrative. Like I don't want to tell myself that story. But they just like, they cook and they play and they coach sports. And I'm just like, I don't want to do that. I want to work. I want to work and come home for dinner and be a patriarch and be like, how was your day, And I ask him, how was school? And I've learned like four-year-olds don't know how was school. Like that's not a thing that they want to do. Like not in that way.

Allison: Right.

Andy: Right? It's like, I need to relate to him the way he wants to relate to me, not the way I want to relate to him. I'm kind of waxing poetic about something I feel like all parents understand.

Allison: No, and I think it's interesting too, because my oldest is almost eight and I just think it also changes so much when they get older. And I hear a lot of my friends talk about this too of like, I didn't like being a parent when they were young. And then when they started to read and have really interesting thoughts and questions, and you can ask about really complicated things, all of a sudden you realize you're fantastic at that, at being present in that moment. And that some people love babies. I mean, I hate babies. Like, I can't stand that phase and I think that's okay. And so, yeah. So I totally get that. I know we are almost out of time. I'm looking over my last questions to make sure I hit, I think I hit most of these. see the rest of the lightning round, I actually asked you most of these already. Something I love to do with my son.

Andy: Totally okay. It happened just last night. We listened to new songs and we talk about what the songs mean. It's very fresh. Like when we talk about the lyrics, yesterday we talking about Harry Chapin, Cats in the Cradle, and how it's about a father and a son and the son wants to be like the dad. And then later the dad realizes the son is like him or we went through eternal flame by the Bengals. And it's about loving someone and loving someone forever. And I was able to say to him, know, that's how I feel with you. I feel like it's an eternal flame.

I love you so much and that's never gonna go away. This is eternal." And you know kids, you just can see it land in a good way, right? Like just, that meant something to him. You can't really say it, but I know he was like, my dad's gonna love you forever. That sounds like a good program, you know?

Allison: Yeah. that's so cute. The other things I have is one thing I swore I'd never do it as a parent, but definitely do.

Andy: I think I mentioned the phone, but I'll give a new one, which is just like rejoice in feeding him junk food. Like at the first while, it was like, we just didn't. And last night I was like, you wanna have Wendy's? And he was like, yeah, Popeye, Wendy's. And just like with joy, it's like cheeseburger fries, let's have a frosty. I just, you know, it's bad for him. It's bad for him, but he likes it and it's fast for me. I just didn't see that coming.

Allison: Yeah. You're like how fast I crumbled. Fatherhood has made me softer about blank and harder about blank.

Andy: Man, I would say it's like the same answer, which is disagreements with my wife. Where like sometimes I have more empathy for how hard it is, because I know how hard it is. And then sometimes I'm harder about it. Like the other day I was like, you don't know how to put him to bed, know, like just move him along, you know, and it's like, well, that's not very empathetic. I know how hard it is. And she came in last night and I was like he didn't brush, didn't change, hasn't gone to the bathroom. And so it's like kind of a hypocrite. And then other times I feel so tender towards her, you know, of like, gosh, like I know it's a lot right now and you're dealing with that at work and like, don't worry, I got it. Like, yes, go on that trip, take another two nights or whatever. So that one's hard. It's just the relationship with her as we parent, you know, I think parents implicitly understand like.

It gets better and it's worse. Like you share, you share in the challenge and you're like kinder to each other. And then in other times you like are sharing the challenge, but you're less kind to each other. And I think that luckily we both do it.

Allison: That's a good answer. Last one, one example of how being a dad has made me better at work, which you've already shared some of those, but if there's anything new you wanted to add in for the final question.

Andy: You know, I think you'll like this one. Work doesn't matter. Like, I just know it doesn't matter that much. It's just like, you know, every parents, like, you have a moment of thinking your child has a health issue, right? Like you get a call and you hear something from the doctor, get a text about something. Yesterday was with my niece, she's going through something. And all of a sudden you're like, all that matters is helping my child.

And then it works. Sometimes you can get worked and it's like, it's just a company. You know what mean? Like who cares? It's just a company. You know what I mean? Like everyone who works at pie is employable. The people that put in money are rich. Like part of venture capital is you lose money on 40 % of your deals. I can go do something new. Like it doesn't matter. It matters so much and yet it doesn't matter at all compared to what really matters.

Allison: Right. And there's something freeing with that too. Yeah. My husband is gonna insist that I listen to that on repeat every night because this is what he's telling me all the time. And it's like, know it intellectually, but it's so hard to follow through.

Andy: It's so hard. You want to hear something crushing? Just a really quick story to end this. I recently met someone that worked very closely with Steve Jobs and he was on all the iPhone launches. And he said, everything you've heard about Steve is true, except he was 10 times worse. He was horrible to us. And now he said, my son is going to college and I have so much regret that I gave my time to Steve Jobs rather than to my son.

And he said, I would give anything to have quit working for that asshole and had been more present with my son. And he's like, by the way, my son thinks I'm a good dad. Like he doesn't have any issues. He's going off to school. We have a great relationship. But I know, I know that I can't get those years back. And he's like, I would kill to go back and have a four-year-old. And it just was like, gosh, the wisdom of perspective. It's like we don't have the wisdom when we need it, we only have it later. And I went up to him later in the day and I was like, you changed my life because that's gonna help me. That's gonna help me a little bit. I'm gonna try to show up a little differently. I mean, look, that was three weeks ago. But you know, I gotta remember that. There's just so much wisdom in what he said.

Allison: Yeah, you're a changed man. No. Yeah. Yeah. Well, thank you so much for your time today. I know I totally took advantage of your generosity with your time. But I'm glad we got to talk about all of these topics because I did a lot of research to see how much you've spoken about fatherhood and you haven't a ton. So this was really fun. And I think on just like a personal level to be able to talk to somebody who had so much success, who had so many learnings, and now the stage you're in, I just think you're in a really fascinating period of your life. And so this was really fun for me. So thank you so much for your time.

Andy: Thank you so much.