Inside a Double Alpha Household: Building Startups and a Marriage

What happens when two founders build companies—and a family—under one roof?

In this episode of Unbottled, Manuela sits down with Andy Dunn — a founder of Bonobos, Monica + Andy, and Pie, venture investor, and author of Burn Rate — for a candid conversation on entrepreneurship, partnership, and the reality of a “double alpha household.”

But this isn’t a typical founder interview. It’s a behind-the-scenes look at what it actually takes to build ambitious companies while building a life together—navigating mental health, parenting, competing priorities, and the constant tension between ambition and presence.

Together, they unpack how to support each other without collapsing into each other’s work, what venture capital often gets wrong about long-term bets like hardware and infrastructure, and why betting on your partner may be one of the boldest (and riskiest) investments you can make.

In this episode, you’ll see:

• What a “double alpha household” really looks like (and why winning isn’t the goal)
• How to balance being a partner, investor, and operator at the same time
• Why startups can feel like a “mind virus”
• The role of sleep, exercise, and routine in protecting mental health while building
• How parenting reshapes ambition, time, and identity
• Why venture capital struggles with non-consensus, long-term investments like hardware

Andy also shares how his relationship with ambition has evolved—from chasing outcomes to finding meaning in the process itself.

Because when you zoom out, building a company is just one part of the equation—the harder challenge is building a life that can sustain it.

💧 Unbottled is brought to you by Kadeya — building closed-loop beverage systems for a world beyond single-use.

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Follow Andy Dunn

Linkedin: https://www.linkedin.com/in/andyrdunn/

Instagram: https://www.instagram.com/dunn/

Substack: https://dunn.substack.com/ 

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Follow Kadeya: 

Linkedin: https://www.linkedin.com/company/kdy/ 

Instagram: https://www.instagram.com/kadeya.club/ 

Tik Tok: https://www.tiktok.com/@kadeya.club 

Website: https://www.kadeya.com/ 

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Follow Manuela: 

Linkedin: https://www.linkedin.com/in/manuelasweb/ 

Instagram: https://www.instagram.com/manuelasweb/ 

Substack: https://manuelazoninsein.substack.com/

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Transcript

SPEAKER_04 0:05

Today's guest is someone who knows a thing or two about building companies and living through the highs and lows that come with it. An active venture investor through Red Swan Ventures, and the author of the best-selling memoir Burn Rate, Launching a Startup and Losing My Mind, where he candidly shared his journey with entrepreneurship and bipolar disorder. But today's conversation is a little different because Andy also happens to be my husband, and along with myself, the largest investor in Kadea. So instead of a traditional founder interview, we're talking about what it's actually like to build companies and a family at the same time. The reality of a double alpha household, how we try to keep work from taking over our lives, and what it means to bet on each other through the chaos of startups, parenting, and everything in between. Let's do this. So you recently wrote about the double alpha household on your Substack. What do you mean by that?

SPEAKER_07 1:15

I've got a friend named Jackson. I won't specify his last name. And he has this saying, I don't know exactly what the norms are around what kind of language we use on the show, that when you get home as a man, you hang your balls with your keys and you walk right in. But if you forget to, like you're gonna have a really bad, you're gonna have a really bad evening.

SPEAKER_04 1:35

And I So what are you saying?

SPEAKER_07 1:37

Well, I think that if you're an entrepreneur and a founder and a CEO, at work, you are an alpha, right? You are the head pack animal. And I don't think that serves one particularly well at home. And so I think this concept of the double double alpha household is fun because what do you do when you have two equally alpha people who spend their whole day being the boss, right? Come home and have to be a partner.

SPEAKER_04 2:08

Okay, so two entrepreneurs, one marriage, one home. What could possibly go wrong?

SPEAKER_07 2:14

Yep. Well, and I think it's it's even better when you're investing in each other's businesses.

SPEAKER_04 2:22

It makes it more fun.

SPEAKER_07 2:23

Yeah, you just further like at that point, just go for it.

SPEAKER_04 2:27

Um no more, no more boundaries, just everything blurred.

SPEAKER_07 2:31

Well, I think we've done a pretty good job at the boundaries, but maybe too well, like as we've been talking about. Like it's one thing to be backing someone spiritually, and then another one to be backing them financially and figuring out what's the right amount of helpful or unhelpful. And I think for a while, my my mindset has been just let Manuela do her thing, and then you know, this is a funny thing about an interview with the actual protagonist that we're talking about. It's also not supportive necessarily to not get in there a little bit with questions and ideas, and you know, as we've been talking about. Um, being a cheerleader is nice, but maybe a great partnership is more about being an instigator and an interrogator and uh and a supporter and a cheerleader.

SPEAKER_04 3:23

One thing that you had said early on in our marriage was at the end of the day when we'd come home and then you'd hear whatever I was complaining about, and you would ask, Well, do you want me to listen and agree? Or do you want me to respond and give suggestions? And I think that's been a really helpful distinction for me as well.

SPEAKER_06 3:50

Um wait, I said that?

SPEAKER_04 3:52

Yeah.

SPEAKER_06 3:53

Whoa.

SPEAKER_04 3:54

Yeah, it was pretty smart. Clearly, you don't remember that.

SPEAKER_07 3:58

Oh, come to think of it, I remember that.

SPEAKER_04 4:01

I held on to it. Um, but it's been, yeah, I agree with you. For me, it's kind of uh a step-by-step, occasion by occasion call on when does it make sense to talk work and business. Um, so before we get into the serious stuff, I'm curious. You can tell me as well as every single person in the audience at the same time. What do you think people assume about our relationship that's wrong?

SPEAKER_07 4:34

I think they can't, they don't really think that we're this good looking. Yeah. Um, it just would be hard to believe. So I think they assume I use a lot of makeup and um hair gel. I don't know. Do you do you remember? I tell a story about the origin of my book that I don't even know if it's true. So you can help me audit this. But do you remember the day that the architectural digest piece came out in New York of our lives? Did we do you what do you remember about that day?

SPEAKER_04 5:09

I think I got a lot of messages on Instagram.

SPEAKER_07 5:11

Yeah.

SPEAKER_04 5:12

But nothing more. Oh, I do remember you were embarrassed about your nails, your toenails.

SPEAKER_07 5:19

Oh, yeah, my toenails.

SPEAKER_04 5:20

And like deep in the Instagram comments.

SPEAKER_07 5:23

Um, they I was like zooming in. She's like, oh man, those are some snappy nails.

SPEAKER_04 5:29

She just gave birth and her toenails look nice.

SPEAKER_07 5:31

Yeah, someone was in the comments about that.

SPEAKER_04 5:34

Go get a pedicure.

SPEAKER_07 5:36

I just felt like such a fraud that day because it just all looked so good. Our house looks so good, we look so good. Like it just was this is all going so awesome. And it's such a fucking shit show life. You know, it's just not, it's hard.

SPEAKER_00 5:55

Yeah.

SPEAKER_07 5:55

And back to the point about conversations at home, we're we're also often exhausted, right? And I think that's normal for parents in general, but I don't know what people think, but it's definitely not what they think. It's different than what you think.

SPEAKER_04 6:11

Yeah, I mean, I agree with you. It's it, we're we're exhausted all the time. So it's not like we're also getting ahead of things. A lot of times it's reactive and like we make the mistake, we make a mistake three, four, or five times, get annoyed with each other three, four, five times, and finally one of us, usually you, will be like, should we step back and not do that again? But a lot of the times it's just us.

SPEAKER_06 6:36

Is that usually me? I think so. How come you don't talk about any of this at couples counseling?

SPEAKER_04 6:42

We gotta bring her in saving the good material. Bring in Mary Joe.

SPEAKER_06 6:46

Be like, look at this.

SPEAKER_04 6:47

It's true. Um, maybe I'm hard too hard on you in couples.

SPEAKER_06 6:51

Yeah, but we do it on Friday.

SPEAKER_04 6:52

But it's like what you said the first time we had session, you were like, I'm ready to win. Like you came into therapy to win.

SPEAKER_07 7:00

The goal of therapy, someone wins and someone loses, right? That's like the healthy mindset to take into it.

SPEAKER_04 7:05

Yeah, so I'm holding on to that. Still want to win. So, what has it actually felt like for you watching me build Kadea, especially as someone who knows firsthand how hard company building can be?

SPEAKER_07 7:18

First of all, I'm just so proud. I'm so proud of you because I get to see what goes into it. And I think it's a courageous thing that you're trying to do here. It's just all startups, I think, are hard. Kadea is particularly hard, right? It's got capital intensity and long-term conviction that is required from the team and investors. And it's it's like uh one someone I know recently told me, like, hey, I really like what you're doing with something. And I was like, Well, what do you what do you mean? And I don't think it applied exactly to my my day job at Pi, but he was like, It just seems almost impossible what you're trying to do. Yeah, like it's like I really he was like, I really good for you.

SPEAKER_04 8:10

But I'm not gonna bad.

SPEAKER_07 8:11

It's like a math class in college that's like you know, 300 level, where you're like, well, I wouldn't take that class, but really proud of my friend Bob. And I think there is an element with seeing the cadea journey, we're like, holy shit, like this is this takes a 30-year view of the future, and then you gotta orient it against a five to seven year investable time horizon. So I'm just proud. I think that's the main thing.

SPEAKER_04 8:41

Um I also I hope you don't say that in therapy.

SPEAKER_07 8:47

I'm trying to win, she'll see right through it.

SPEAKER_04 8:50

Yeah.

SPEAKER_07 8:51

Um I also feel like it's been special to see how much you've evolved and grown through it, like it's tested you and also it let your star shine, you know, which is why I was loath to come on this podcast and share the glory. I don't want to sh I mean the the backstory for for the group out there, I guess, is that um I used to steal the spotlight was a narrative in our marriage.

SPEAKER_04 9:23

You still do, but I'm okay with it.

SPEAKER_07 9:26

Well, now I'm stuck in a box in this particular environment.

SPEAKER_04 9:29

Okay, sorry, I take that back.

SPEAKER_07 9:30

No, but it's it's like um I don't know.

SPEAKER_04 9:34

I tell myself I've become used to take the spotlight.

SPEAKER_07 9:37

Yeah. I've just gotten to see you shine and the world get to know you, and I love that because the world needs more of you.

SPEAKER_04 9:49

Thank you. So you want to get into some tougher questions?

SPEAKER_07 9:54

Those were not tough.

SPEAKER_04 9:56

We're gonna get more specific.

SPEAKER_07 9:58

Okay, good.

SPEAKER_04 9:59

What does it mean to be married to another founder?

SPEAKER_07 10:02

It means you're fucked, you know, if you think about it.

SPEAKER_04 10:06

Like I feel like if if the if you yourself are a founder.

SPEAKER_07 10:10

Yeah, it it's like you're right, you have a fundamentally undiversified strategy financially, uh parentally, domestically. So it's it's like not a good idea unless it's inevitable, right? And I feel like when we got married, I knew I was going into the double alpha. But the thing about the double alpha that we didn't talk about is you can't really win as a double alpha as a man. Because it by winning you lose.

SPEAKER_04 10:48

I want to hear more. I feel like it's true for the woman as well. But you you you state your case first.

SPEAKER_07 11:01

You already know these stories. That's why this is like funny to do. It's like paranormal paranormal. But do you remember the Uber driver, the Uber X driver in San Francisco that I told you about when we were engaged? Yeah. And he was talking, I was sitting in the front seat for some reason, and he was talking to his pre-COVID. Yeah.

SPEAKER_04 11:19

Someone reminded me, we used to sit in the front seat.

SPEAKER_07 11:21

I was in the front seat. He picked me up in the presidio, and he was talking to his presumably wife in Portuguese, and he was just chatting away, but he was talking Portuguese in an Italian accent. And so I when he got off the phone, I was like, Hey, you know, is your wife Brazilian? And he was like, How do you know? And well, speaking Portuguese. I said, I have, you know, I'm engaged to a woman who's from Brazil, and he goes and he goes, Oh, let me tell you, do not fight.

SPEAKER_06 11:50

Never fight with her, always just carinho. There's no point to argue. You you if you win, you lose. So just lose every day. You're going to be with her anyway. And it was this like whole pep talk. And I think we were, you know, engagement is hard, I feel like, in some ways.

SPEAKER_07 12:08

Like we were going through some moments. And it's just true. Like, you don't, there's no point to win, like, you don't you don't want to win, I guess. We're having this, you know, series of conversations we're making right now, lifestyle-wise. And if I discover that there's something that you want to do, it's just better to do that. I feel like you can't be a CEO in a good marriage.

SPEAKER_04 12:32

But that's true anyway, right? That's that's a lesson for everybody. When you whatever your role is at work, you know, the idea is that you're not gonna try to be the boss or the manager.

SPEAKER_07 12:49

I don't know. My mom's kind of the CEO. That's what I grew up. I grew up watching all the women as CEOs.

SPEAKER_04 12:57

Yeah. I think that's why one of the many reasons why I wanted to be with you. Um, because you have such a positive outlook on on your mother and on women leaders. Doesn't make it easier at home necessarily. But I think for a woman, it we also lose because we're still expected to do all the traditional female tasks, right? And projects while being CEO.

SPEAKER_07 13:30

It's definitely worse to be the woman, I think.

SPEAKER_04 13:33

That's good. Glad you agree. See what I mean? Yeah. Well, continuing on that thread, how do we avoid letting work take over the relationship?

SPEAKER_07 13:46

I don't feel like we have that problem, actually. Yeah. Yeah, what's your take?

SPEAKER_04 13:54

Well, I think the challenge is we've avoided talking about work for a long time.

SPEAKER_07 14:00

Yeah.

SPEAKER_04 14:00

Or more recently.

SPEAKER_07 14:02

Well, let's have it out right now.

SPEAKER_04 14:04

And increasingly at home, we have been talking more about work, or you've been asking more about Kadea. Even before I started Kudea when I was still at Palantir, though, I'd come home and I'd be like, tell me everything about your day. And you'd be like, uh, I don't want to tell you anything. Like, I I wanted to like pull it out of you. And now I think both of us come home. Neither of us wants to talk about work. Yeah. We're just tired. I want to either chit-chat and relax, or we end up talking about logistics, yeah. Which is the other thing that happens when you're a parent.

SPEAKER_07 14:36

Yeah.

SPEAKER_04 14:37

You like go to bed talking logistics, yeah, wake up talking logistics.

SPEAKER_07 14:42

Yeah, it's like you need to have enough time to get through all the logistics to even see what's on the other side of it. And I think back to the double alpha, there's so much logistics and so little time. So I like what we've been doing recently on occasion by actually having a meeting during the week when we both have that energy and we're in that mindset, right? It's like it's like a paradox. What we actually need is to be more CEO and founder like sometimes in our personal lives, which we can do, right? Like it probably only takes half an hour a week of like being on. But when someone's I won't specify who, but like someone's scrolling Instagram, the other one's playing chess, you know, you're there for a period of time, but your attention attention is distorted, right? And these phones, right? It is the damn phones. It's like being fully present is just as big of a trick as being co-located and not working.

SPEAKER_03 15:42

Yeah.

SPEAKER_07 15:43

And then I think there's the track in your mind of what you're doing at work, what you need to do. It's a I joke with my team, I'm not the originary of this, but startups are like a fucking mind virus. Like it just takes over your brain. So it's like, how do you get out of that and be present without like being on vacation?

SPEAKER_04 16:04

Yeah. Yeah, and learn to do that every evening and every weekend. Do you want to talk a little bit about how we've some of the boundaries we've put in place?

SPEAKER_07 16:15

We have boundaries?

SPEAKER_04 16:17

I'm talking about on the with a cell phone.

SPEAKER_07 16:19

Oh.

SPEAKER_04 16:20

Like your cell phone Sabbath.

SPEAKER_07 16:23

Yeah, I mean those are my best experiences of Friday evening into Saturday, is just airplane mode on the phone. And still interesting, like how hard it is to do, or like just to have it in like the bathroom or something. Because I I do think there is like a thing where even just having it nearby robs attention.

SPEAKER_04 16:47

Absolutely.

SPEAKER_07 16:49

But then you're supposed to work seven days a week or something, right? And what I found is that my team would prefer, they prefer smartphone Shabbat.

SPEAKER_04 16:58

Like they want to check out a day.

SPEAKER_07 17:00

Yeah. Yeah, they want to break. It doesn't necessarily need to line up with my break. But if someone's on, I feel like I need to be responsive to that person, right? Or there's like this one thing to do. So we've all had that experience. Like you're about to whatever, put your phone to the side and go to bed, and you're like, oh, I got to do this one thing. And it could even be life logistics related.

SPEAKER_00 17:20

Yeah.

SPEAKER_07 17:21

And and so you could just go back into that universe of stuff. And then there's all these other adjacent possibilities. Okay, I sent that message or email or I calendared that.

SPEAKER_04 17:32

But I got another message.

SPEAKER_07 17:33

Got another one. Or let me just check this for a second, right? And I even had this, I think like two nights ago, where I was like, okay, I'm just gonna put it down and start reading. And just for a second, I was like, I'll just check, check the bears trade wire.

SPEAKER_04 17:47

I love this.

SPEAKER_07 17:48

And I just disappeared. I suppose. For two hours. And I at one point I was watching a YouTube video of a linebacker's college highlights who the Bears just signed. And I was like, this is fun. And I thought about it the next day. I was like, what am I doing? Like, why am I watching college highlights?

SPEAKER_04 18:04

So I saw the like the glow, the yellow glow of the screen over your shoulder.

SPEAKER_07 18:11

Yeah. And I I told you this. Like someone calls it revenge scrolling, which I hadn't heard, where you're like, you have your whole day is like fucked with your life and your job. And then finally it you have some time to yourself. Yeah. And it's like, now I'm gonna revenge scroll. Like, I'm gonna just do this for me. But you know, as you pointed out, that is a direct offset to more productive uses of time or getting up early and spending time with your family. Yeah.

SPEAKER_04 18:42

We actually haven't talked about this explicitly. So I'm curious, what can I do to support you? More support, be more supportive of you when you are down, but maybe I'm up. And I'd be curious to flip that then as well. So when like maybe you're having an up day, I'm having a down day.

SPEAKER_07 19:06

Well, you know I told you you should do more drugs. Yeah. I feel like.

SPEAKER_04 19:10

Yeah.

SPEAKER_07 19:11

Just let loose.

SPEAKER_04 19:12

More you mean some drugs.

SPEAKER_07 19:16

Way more slash some. I mean, I'm joking a little bit, but I think this is this is so stressful, I feel like. Parenting, husbanding, wifing, startuping, that like brushing your teething, like exercising. Yeah, it's all it's all for something. Yeah. You know? And time like for nothing. But that is communal or where you can kind of access a headspace that is getting out of that mind virus. Um I don't know. That's fun. And I and I think some of it with the the feedback that we got from our nanny, she was like, of all the couples I've ever worked with, and I only work with power couples, you guys are the worst I've ever seen at taking a vacation at the same time. Right?

SPEAKER_04 20:14

But in those cases, did the women work?

SPEAKER_07 20:17

I don't know if yeah, I don't know what exactly she meant, but it was pretty awesome, I thought, our trip to Brazil this last time where we actually took time off together.

SPEAKER_00 20:29

Yeah.

SPEAKER_07 20:30

And then it's the question of like how do you bring that back into your day-to-day life? Yeah. Takes a lot of intentional calendar design and then compliance. Neither of which are my strong suits.

SPEAKER_04 20:46

Yeah, we also have to be honest with ourselves, I guess, which is not my strong suit.

SPEAKER_07 20:52

It kind of is.

SPEAKER_04 20:53

Sometimes. Sometimes. Sometimes hope becomes a strategy.

SPEAKER_07 20:58

Well, it has to be sometimes.

SPEAKER_04 21:00

Yeah. But I I mean, I I remember there were periods where you were both succeeding, like when you were going through the Walmart acquisition and I was like at Palantir just grinding away. I tried to be supportive of it, but there were also pangs of like, I don't know, envy that I wanted that, you know, um, and wanting and feeling that envy and then stopping and setting it aside to be like, but this is wonderful for someone I love so much. This is great. I'm gonna be supportive of it. But having to kind of pause and set aside the envy. On the flip side, when you're down, you're having a tough period, you'll tell me, you know, in general, I've tried for the last almost 10 years to pause and figure out how I can be helpful and support. But I've also had periods where I'm like, yeah, but I'm finally starting to hit my stride. Like, why do I need to slow? Down. I don't know if you have comparable experience. Or you're just selfless Zen Buddha master.

SPEAKER_07 22:09

Yeah, right. We should always do podcasts. I know you should invite MJ. Travel around with these microphones if you're gonna say if you're gonna whisper these sweet nothings. Um when when I saw, yeah, when I saw our MJ. MJ is our couples counselor, if you can't tell. Or coach. She calls herself a coach. Um, she's also the sponsor of this podcast. No, she's not.

SPEAKER_04 22:35

Uh and and she refers to us as a trio.

SPEAKER_07 22:38

Yeah, she does. I think it will be great for us to do a half day together. What? When you didn't come to the last one, which is totally fine.

SPEAKER_04 22:49

The last session?

SPEAKER_07 22:51

Prior to. Uh-huh. Um she went like deep into the timeline of our marriage. That's what she wanted to know. She wanted to know like she's taking notes. And one of the things that I hadn't really thought about, it's obvious in retrospect, was that I sold my first company a month within a month of our marriage.

SPEAKER_00 23:15

Yeah.

SPEAKER_07 23:17

And we didn't get too deep into it, but it was sort of like all of the chaos of that.

SPEAKER_00 23:24

Mm-hmm.

SPEAKER_07 23:25

Yeah, I was able to like end that journey at the beginning of our marriage.

SPEAKER_00 23:31

Mm-hmm.

SPEAKER_07 23:32

So that I don't know, it just kind of gave me a moment to like reflect and have insight into like what if I had gone through the chaos of that or was going through it now. And not, it's not your first company, but some of the challenges of scaling something with inventory, right? Where you have to finance both your team and you know, the investment in the product that you're building. I don't know. It was just I just had never really thought about how hard it is. And I know it, but I hadn't thought like, man, like that was just a new way of thinking about it for a second. Because I always say like I never would have been able to have a partner like during that. It was so all and I think that's not exactly true, but yeah.

SPEAKER_04 24:24

Well, we were already living together then, but I think also not having kids for the last few years of it. Yeah. Not having a kid at that time. Yeah. I think we were both in like just it was like career or bust. So it was easier.

SPEAKER_07 24:41

It's a lot easier to do the double alpha thing without kids, right? Because you just have your and it, you know, there's some wisdom to it, right? Like, yeah. Then the time that you do have you can enjoy in theory.

SPEAKER_04 24:57

When when you don't have a kid, I think so.

SPEAKER_07 24:58

Like, I think back to that era of our lives, and I'm like, well, that was fucking easy. Like we just worked and hung out. Like, and somehow our time got filled. And then it's this beautiful thing having a child, as you know, it's like it's amazing. But then how where does like the jigsaw puzzle go of that third little piece of the pie? You know, time for each other. And how does that how do you find that time if your wife does not have put your child to bed?

SPEAKER_04 25:30

I just go to bed with the child. I know. Easy, two and one.

SPEAKER_06 25:34

He is cuddly.

SPEAKER_04 25:36

Well, on that note, what have we had to let go of to make this season of life work? Or what have we outsourced?

SPEAKER_07 25:46

There is some value in like doing the dishes together and the laundry and all these things like that I saw my parents doing. But I just don't, it's hard to pick imagine where that time would go.

SPEAKER_04 26:02

Yeah, that's a concept.

SPEAKER_07 26:03

I guess we've been lucky to triage for us. Have a team. Mary Joe is making fun of it. She's like, You talk about your team like at home.

SPEAKER_04 26:14

But well, that's one of the challenges as the woman, right? Is a lot of those are activities that the woman normally in traditional gender roles would take care of. Yeah. Right? Like doing the laundry, cooking dinner, cleaning up.

SPEAKER_05 26:30

Yeah.

SPEAKER_04 26:32

So it's it's in part um because I work.

SPEAKER_07 26:36

I mean, I would be great at that stuff if I didn't work. We would have dinner once a week.

SPEAKER_04 26:40

When I met Andy in his frid his kitchen, you had no utensils, no plates.

SPEAKER_07 26:49

No.

SPEAKER_04 26:50

I think you had what did you have in your f- That's what restaurants are for? Yeah. You you had nothing in your fridge. You had you had an egg? I had an egg. You didn't know how to fry an egg.

SPEAKER_07 26:58

I fried you a great egg.

SPEAKER_04 27:00

You've learned to fry an egg.

SPEAKER_07 27:02

That's okay. That's fair.

SPEAKER_06 27:05

Wasn't there one with a little fresh red pepper?

SPEAKER_07 27:09

Anyways.

SPEAKER_04 27:10

What? No? Fresh red pepper. I think you had milk in case you bought a coffee.

SPEAKER_07 27:16

No, for cereal.

SPEAKER_04 27:17

Oh, cereal. You had a box of cereal. That's what you had.

SPEAKER_07 27:21

It's pretty much nothing's changed.

SPEAKER_04 27:23

Yeah.

SPEAKER_07 27:24

Those are the three things I make fried eggs, coffee, and cereal.

SPEAKER_04 27:29

Yeah, what else? You've learned one other thing, haven't you? Salmon.

SPEAKER_07 27:33

Green chicken chili.

SPEAKER_04 27:35

Yeah, and chili. That was good. Um, but yeah, for outsourcing, we we have child help, we have child care help. Yeah. We have housekeeper.

SPEAKER_05 27:44

Yeah.

SPEAKER_04 27:46

You order, you get someone to cook you food.

SPEAKER_05 27:49

Yeah.

SPEAKER_04 27:50

I've been cooking more.

SPEAKER_05 27:53

Yep.

SPEAKER_04 27:54

Um what else could we outsource? But that is a that is.

SPEAKER_07 28:01

We can outsource the logistics.

SPEAKER_04 28:03

Someone else to do it? AI agent.

SPEAKER_07 28:05

That's what I'm working on. Yeah. Sounds weird. It can make calendar invites now from text.

SPEAKER_04 28:12

Okay. Cool. Um, so is there such a thing as balance or is it just constant reprioritization?

SPEAKER_07 28:21

We could outsource cuddling.

SPEAKER_04 28:23

Yeah.

SPEAKER_07 28:24

Cuddle, cuddle, cuddle AI. And then we could just sit there and scroll on our phones all day. Humanoid robot.

SPEAKER_04 28:29

Yeah.

SPEAKER_07 28:30

Just rubbing your back next to someone. Is that you? Edgar, quiet.

SPEAKER_04 28:35

There isn't there is a robotic uh massage company, actually now.

SPEAKER_07 28:40

Sounds about right.

SPEAKER_04 28:41

You talked a little bit earlier about, you know, the mess behind the appearances. What don't people see behind the polished founder or operator identity?

SPEAKER_07 28:53

I don't know how to say this exactly, but I I feel like we're um we're just or such ordinary people. You know, like we're just, I don't know. It's like a lot of this stuff, I feel like is made up. You know, even now, like the lights, the microphones. Let's talk about our jobs and our marriage. Like it's there's an element of theater, I feel like, to the startup world that maybe this is obvious, I guess. And then at home, I'm like, I just want to get on the sofa and watch the bears with a cold cadet bottle in my right hand.

SPEAKER_04 29:36

And you just prepared dinner in front of you.

SPEAKER_07 29:40

Yeah, exactly. Perfect. I don't know. We're just like a couple that does this thing that's semi-public. Yeah.

SPEAKER_04 29:48

But well, everything is semi-public these days, anyway, right? Increasingly, there's that pressure to be public.

SPEAKER_05 29:55

Yeah.

SPEAKER_04 29:56

I one thing that we've been doing that I think is funny. I don't know if you posted it, or maybe we could post it in like the show notes. I cut your hair.

SPEAKER_07 30:05

Yeah.

SPEAKER_04 30:05

I started cutting your hair.

SPEAKER_07 30:07

Is this ongoing, you think?

SPEAKER_04 30:09

Um I auditioned. Did I not make the cut?

SPEAKER_07 30:12

You did great. It was free.

SPEAKER_04 30:15

Yeah.

unknown 30:16

Yeah.

SPEAKER_04 30:17

This is the product. What do you guys think? No? All right. So you're going back to outsourcing your cuts?

SPEAKER_07 30:25

I haven't decided yet.

SPEAKER_04 30:26

Okay. I'm still in uh the audition phase.

SPEAKER_07 30:29

Yeah.

SPEAKER_04 30:30

Okay. Um, okay, so you've you've been incredibly opening open about bipolar disorder and mental health, uh, especially in your book, Burn Rate, which is a great read. I live through it and I still read it and I still laugh out loud.

SPEAKER_07 30:46

What do you still read it?

SPEAKER_04 30:47

I still read it. I'll read parts of it. Um I haven't read the whole thing since that the draft version, the galley version, where I where I was surprised about some things. You know, it's good to I was like, oh, you did that?

SPEAKER_07 31:03

Yeah.

SPEAKER_04 31:05

Um, so how has your relationship with ambition changed over time?

SPEAKER_00 31:11

Hmm.

SPEAKER_04 31:16

You talk about this a bunch.

SPEAKER_06 31:18

Yeah.

SPEAKER_07 31:22

I I'm toying around with this idea that another founder shared with me that is basically it's basically Buddhism, but that uh it's just all an illusion. So if it is all an illusion, what's the point of trying so hard? And I guess because it's fun and it's meaningful, and most of all, it's great to be with a great team and to spend your days with the great team that's trying to win together. You can tell winning doesn't matter to me. And what I remember now, because I got to go through the first rodeo, is like getting to the goal is what animates your the locomotion of that team. But what is the goal? And I think in the venture capital world of startups, which by the way is a small corner of the business world, it's like an exit. It's an IPO or it's a sale is like the two ways to do it. And then having gone through that, when you know, at the time of us getting married, like being like, oh, I'm just me, like six weeks after that. It's sort of like a somewhere in there was a letdown period of my personal life took a step forward, but in some strange way, now I work for this big company. And my professional life, I've sort of lost that. Like I'm building something. It was cool, it was new challenges. And unfortunately, now or fortunately, that like brought me back into it, which is something I talked to Mary Joe about because I said I feel I don't know if I want to tell you this, but this was in your one-on-one.

SPEAKER_04 33:08

Yeah.

SPEAKER_07 33:09

Yeah.

SPEAKER_04 33:10

Tell me in front of everyone.

SPEAKER_07 33:11

Well, I feel selfish that I did it did another one when I didn't need to, right? Like that's the that's the underexamined part of the double alpha, is I didn't need to do it again. Um but part of why I did it, and that has changed my relationship with ambition, is that I love the doing of it that the goal inspires, but the goal itself is like an oasis. Like when I just get there, when I just get to that financing round or that X milestone, and then you get there and then you just keep going. So you kind of, I don't know, it's cliche. But I just I enjoy it now more because I'm not actually trying to get, I don't believe the there is there. Yep. It's just the here. You have to be present, yeah, and having fun with it.

SPEAKER_04 34:04

Although you did say yesterday with MJ that you were talking about how at the end of your life, you know, at some at someone's funeral, at one's funeral, no one cares what what company you built.

SPEAKER_07 34:19

They don't care. And I just, you know, I guess for the benefit of the group at our my cousin's husband's funeral, Rahul, who, you know, passed away at 47. It was amazing to see how many friends came up to testify as to what a great friend he was. And it just reminded me of that cliche thing of you know, no one on their deathbed is like, oh, if I'd only if I'd only worked more.

SPEAKER_00 34:51

Yeah.

SPEAKER_07 34:52

And then the curve that folks show you of like time that you spend with like your parents, and it's like, you know, and even your own kids is like, hmm.

SPEAKER_01 35:03

Yeah.

SPEAKER_07 35:04

And then there's like time alone.

unknown 35:06

Yeah.

SPEAKER_07 35:07

And like work is so long. And so even acknowledging our child, it's like this is a fleeting experience of having this human in our home, let alone its beautiful, magical young age. And that's messed up because for the from the founder vantage point, because it is either so fun or so immersive or so stressful, you are distorting so much energy and attention to this thing that maybe isn't the biggest long-term creator of meaning and sustenance in your life. It's not so binary, I don't think, but it's it's definitely makes you wonder.

SPEAKER_04 35:45

I think it is in large part what gives us meaning, right? Purpose. Get up in the morning. Yeah. Like, what are you getting up for? I think you and I both share the trait of wanting motion and feeling like we're uh overcoming obstacles and maybe changing people's minds or changing the world in some small way. I don't know that we'd be as as available to our friends and family if we didn't also have that.

SPEAKER_07 36:24

I like this narrative. I'm gonna go with it.

SPEAKER_04 36:26

Okay. I've been thinking about it. I like what you did today.

SPEAKER_07 36:29

Really?

SPEAKER_04 36:30

I was like, well, I don't really care what people say about me at my funeral. Where's so true? I don't. I'm not gonna be there.

SPEAKER_07 36:38

I'm hoping not to be there either. Um legacy. But where does it where's what is my legacy? Legacies are so dumb. Where what's the edge though, then? Edge of Well, if you're you are changing the world and you do love doing it, where how do you I don't know, you probably don't have enough time to think about it. But what's the what's the outer limit of that? Yeah, relative to the constellation of yeah.

SPEAKER_04 37:10

I the I I'm not good at that.

SPEAKER_07 37:12

You know what else I've been wondering is do you think it's good that we both know so much about startups?

SPEAKER_04 37:18

Why?

SPEAKER_07 37:19

I don't know. It's like it's funny to work in this arcane corner of the world where you know you go to bed talking about cap tables or some fucked up shit. Like we I in my mind, like we take I take it for granted that we both have such an understanding of it.

SPEAKER_04 37:34

Yeah. I've been thinking more and more frequently as I learn about new, like I've you know, I've been obsessed with debt lately, like learning all about debt and how debt is gonna be a part of the capital stack for Kedeya. And now I drive by like on some main street and I see a bank. I'm like, oh, that's what you're there for. Like, that's what the bank has been sitting there for all. I used to drive by and be like, what is what do banks do? Why is there a building? They're just gonna have a check account. I can do that online.

SPEAKER_07 38:09

What do they do at the bank?

SPEAKER_04 38:10

I'm still actually not 100%. But one thing I think they do is they meet with people like me to make sure we know how to put our clothes on correctly and brush our teeth. And we look like normal human beings, like they could trust us.

SPEAKER_07 38:25

Do you think there's a study that people that brush their teeth are better at paying off their debts?

SPEAKER_04 38:31

Ooh, that's a tough one. At first, I would say yes. But then are they spending too much time brushing their teeth?

SPEAKER_07 38:38

Yeah. Like not enough time. You want someone that brushes their teeth, but if they're really good at flossing, like you're screwed.

SPEAKER_04 38:44

How do you think about protecting your mental health while building at a high level? I can think of some examples of of how you're managing that, but you go. Well, you you talk in your book a lot, uh, not a lot, but you've talked in your book and then you reference often. I think it's great how sleep is so critical. You have a great regimen with um a psychiatrist who you check in with two times a week now. Used to be three. And you guys have you have your your medicines, your menu of medicines that you kind of have your your, you know, meat and potatoes every day. And then you've got a few toppings that you can layer in. Um and then you spoke a couple months ago at the brown, was it brown man therapy? Was that, and you were on the on you you spoke on the panel, or you were the the guest, the headliner. Um, and you talked about how with our physical health, we all, you know, we know that we've got to brush our teeth every day to prevent cavities and got to eat right to make sure that you stay healthy and fit. You got to exercise so you don't get a heart attack eventually or any long-term problems. But with mental health, we don't do that. We wait till the equivalent of a heart attack to then start taking care of our mental health. And how you took you talked about treating your mental health as part of your health regimen. So I thought that was really cool. Um I know I'm answering your question.

SPEAKER_07 40:23

That was great. Keep going.

SPEAKER_04 40:24

Uh but the other thing that you talk a lot about is how important now exercise is for you and like eating right. You stop drinking. And that's been really helpful for you. Yeah. So I I see how you're editing your day-to-day as well, so that you can hopefully be healthier over the long term.

SPEAKER_07 40:47

The sleep one is the one that intrigues me so much because, and I think this era is over, but I definitely felt like there was a thing when I was building bonobos that it was a badge of honor to not be sleeping much as a founder.

SPEAKER_00 41:05

Yeah.

SPEAKER_07 41:06

Like, whoa, you know, Andy's on until like two in the morning, and then is back at it, and you're just like always on, and something is getting past your way, and like you're passing the ball back, and sleep takes away in the jigsaw puzzle from the time that you could be spending working. And from a mental health standpoint, like that just didn't work out for me. Like, that wasn't gonna be sustainable. And now I it's it feels like if I can't get at least that to 1.5 to two hours of REM and you know, 45 minutes to an hour and a half of deep sleep, then like it's like taking a brick out of something like that, everything else is just worse. It's harder to exercise, tired at work, tired around family. And so once you start optimizing for that, set aside the seven or eight hour typical thing, but the actual restorative sleep. And as you know, I have a few gadgets to measure this. Um, then all of a sudden it's like, well, why drink? Right? Because alcohol makes it very hard to get that restorative thing in, and it's also kind of fun. So it's like now you're up late and all this stuff. So that was another that just kind of pulling that out, like supported the sleep part. You know, and exercise is the one that's been harder for me, whereas you're like to have 20 years of pretty being pretty consistent, just everyone can note. For me, it's very hard to do that rhythmically. Like this morning, I did not want to go. I was so I just want I I I even got sad in my own mind. I was like, I don't want to go.

SPEAKER_06 42:54

Like that was the conversation I had with myself. I want to have to exercise.

SPEAKER_07 42:59

And that's just been big. So it does feel like the nerdy bro term of a stack, where like the bottom of the stack is sleep. Then I don't want to make it a pyramid because it's I'm not sure what's more important for someone with bipolar one medication, for someone like me with with that mental health challenge, seeing a psychiatrist or therapist with rhythm, which is also just helpful to unburden oneself. We never talk about you. And then as you go up, there's just more that you can put in place, you know, exercise, nutrition, et cetera, where okay, now we have like infrastructure built where like some shitty thing at work you just can absorb it because it's not it just doesn't matter enough. But it feels like it does. And I have to step outside of myself, like recently we let someone go at work and It just was a very consuming experience. And then, you know, that person now has a new job and some things are better because of it. And it's like, well, why was that such a big deal? So I feel like I'm liking doing this second company more than the first because those kinds of things were just all consuming. And I didn't have that stack to lean back on.

SPEAKER_04 44:26

Yeah, that's crazy. I don't know how you did that. Well, you did it with lots of coffee and lots of alcohol.

SPEAKER_07 44:34

It was fun.

SPEAKER_04 44:37

So you you've built in in retail, as we were referencing, in brand and consumer for a long time. Um, kind of taking a little bit of uh um diversion here away from mental health to talk about your perspective on retail innovation right now.

SPEAKER_07 44:54

Let's go.

SPEAKER_04 44:55

Yeah. Are you paying attention? You were telling me the other day, we where were we? Oh, when we were in New York and we were walking through the uh Oculus with all the retail shops, and you were commenting how previously you had to be so obsessed.

SPEAKER_07 45:11

Oh my God. And you don't have to Well, it's like reflecting on a different mind virus. Yeah. Right? I think whatever you're building, you just are trafficking and trafficking and thoughts about it all the time. Your own product, competition, investors, your team, what you could build in the future, what else, you know, it's it's like you're just everything in your professional world, which is swirling a lot, is about that company and that space that you're in. And now I'm in I'm there again, but in a different world, the world of you know, social apps and agentic AI. So when we were in New York, you know, walking through, it it wasn't I'm obviously around stores in Chicago, but that part of my brain of in New York with stores just reminds me of a decade of being obsessed with like, why is J. Crew doing that sweater like from that was that was ours last year, right? Or damn, why can't we have stretch denim that's as good as AG? Or, you know, like it just always thinking about the product and with retail, the product's everywhere. Everyone is a clothing customer. Yeah, there's clothing stores everywhere you go.

SPEAKER_04 46:28

Yeah, it's being advertised constantly.

SPEAKER_07 46:30

Yeah, and at some point we had stores, you know, 60 and online sales, Cyber Monday, like just so much in the popular culture is retail that I was reflecting on that life moment and being like, oh, I'm glad I don't think about this that much anymore. There were a few years where every single guy that walked by me, I checked out his butt. You want to see if he was wearing bonobos. Yeah. I became an expert in male butts for like five years. I could tell like what kind it was. And then it what kind of pants, not what kind of buttons.

SPEAKER_00 47:02

What kind of butt it was?

SPEAKER_07 47:03

Maybe I figured that out too. Or at least I could imagine it. And so, and then it was cool when to not do that when you're like, oh yeah, of course that guy's like wearing our pants. Like, I had that at this moment actually at the gym. A guy that I met at the gym today uh is a former NFL. This is funny with all the butt talk, former NFL tight end. And I was so interested talking to him, and then at some point he was like, What about you? What do you do? And I was like, Oh, I used to have this company, you know. And I I say the name because I'm always curious, like if people know it. Spinobos. He's like, Oh, yeah, I know that company. You know, and he was he had the product there, and it just it was just cool. I was like, okay, we built, we built something that matters.

SPEAKER_04 47:44

It's great, and it's and it's doing well, it's doing really well.

SPEAKER_07 47:47

It's just that's the most elegant challenge. Like, can you build something that survives you, both like the culture of the company and the brand, and yeah, that it can like keep going. Um, and I invited him to Daddy Dinner Club, and he was super excited about it. It was funny.

SPEAKER_04 48:01

We had like a I felt like You want to tell what it is, Daddy Dinner Club.

SPEAKER_07 48:06

I mean, the the idea here is like dads, we're bad at life, and one of the things that we're bad at is socializing and meeting new people is like, whoa, I don't have even time for my existing friends. So yeah, we're just trying to get together ideally six guys at a time, once a month, six times in a row. And the cool part, I haven't talked to you about this actually, I don't think, is uh I bring a question each time. And the questions are fun. So, like one we did was um what's something that your dad did that you never want to do? And what's something that your dad did that you want to like carry forward? Or maybe I did tell you this.

SPEAKER_04 48:50

You didn't tell me that question. You told me one about asking about drugs.

SPEAKER_07 48:56

That one was funny because yeah. Drug use? Well, it was like, what do you I made it as a joke? Like, what substances do you use? But basically the theme was like, what do you do to let go? Right? Like, how do you and and it's just fun being around dads because there's just such a it's all there, like the ability to like be funny, be vulnerable, you know, connect with new people, but I feel like it's so bottled up in your average like 45-year-old man who's just like preoccupied. Yeah, we did another one, it turns out everyone there had a son, and so I brought up like what's the most physical you've gotten with your son, which I thought was a weird thing, but I had just gone through our son being like, Bye-bye, you know, you squeezed me, yeah, and it was like this whole treasure trove of stories of like, yeah, my son like hit my wife, and you know, I don't think there was a a person there that I'm I felt like everyone was like a pretty ethical person, but everyone had lost it and had a story about it, and then it became a more interesting conversation than the stories of how do you create boundaries and like what's the right level of discipline? And I think I told you about the one guy who says I'll I'll take your toy away and then just disappears as toys, which I thought was maybe aggressive, but it's it's cool.

SPEAKER_04 50:22

But that's an example of something that you haven't you've actually introduced in this season, is figuring out ways to connect with other fathers, obviously, but people who you otherwise wouldn't meet, right? Because as in a family, it's harder to necessarily make new friends. Yeah. Um, to I think that's helpful with your mental health management as well.

SPEAKER_05 50:47

Yeah.

SPEAKER_04 50:48

Um, well, I'm curious going back to if you think back, you know, to to Bonobo's days to now today, how have you seen venture capital change the last 10 to 20 years? And where I'm gonna head into from there is talk to us about infrastructure and hardware. And, you know, the in the AI era, where that may be one of the few defensible moats. Curious, you know, your perspective on how VC has or has not risen to the occasion.

SPEAKER_07 51:25

It's a funny, it's a funny industry, I feel like. I've gotten to fundraise in it twice with two companies. Also be someone with the side hustle seed fund, be an angel investor in too much stuff. I actually went through a lot of uh angel investments from 2018 to 2022 today. I happen to be in, and it's like, whoo, we did okay, but 90% of stuff was like I did like a green, yellow, red, 90% of them were red. Yeah, they're just gone. And it also we've done some well with a couple of companies that have won, right? And I think that's what disappoints me about venture capital is and I participated in this, is it's like it is a herd mentality business in a category where long-term winning is about being non-consensus.

SPEAKER_04 52:17

Right.

SPEAKER_07 52:18

So it's this paradox of like it's called venture capital. Like the whole point is the power law distribution. The whole idea is that if you're investing in things other people are investing in, there's a good chance that it's not a long-term like way to build a franchise. So I feel like it's gotten worse because it's proliferated so much. There's so much capital out there. There's all these kinds of funds that didn't used to exist. And now they all just, you know, invest in one thing, right? Which is AI. But it was always like that, you know, and and that's where I think about the the pitch of why this is different than what's out there is actually how to make money and build long-term value, and it's how those investors are gonna make money. But it's remarkable how many people you have to go through to find someone, you know, that that believes in it. And I think finding those people are as hard as ever.

SPEAKER_04 53:21

Yeah. Definitely as hard as ever. All right, so we're gonna go into our rapid fire section. Okay. I think you'll be good at this. In part because you took um stand-up comedy class at Second City. So we gotta see what you what you learn there.

SPEAKER_05 53:40

Oh boy.

SPEAKER_04 53:41

Okay. Who is more likely to bring work drama to dinner?

SPEAKER_05 53:47

Me.

SPEAKER_04 53:48

I agree. What's one thing I do as a founder that drives you crazy?

SPEAKER_07 53:57

Unit economic spreadsheets.

SPEAKER_04 53:59

Yeah. One thing you think I'm uniquely world class at courage. Finish the sentence. The key to surviving a double alpha household is alcohol. For one of us.

SPEAKER_06 54:20

I don't know. I lost the key.

SPEAKER_04 54:24

One thing you hope our son learns from watching both of us build.

SPEAKER_07 54:29

Independent thinking?

SPEAKER_04 54:32

He's got that.

SPEAKER_07 54:33

He does. Already, already learned somehow.

SPEAKER_04 54:37

Yeah. And one word for this season of life.

SPEAKER_07 54:42

Sacred.

SPEAKER_04 54:44

I agree.

SPEAKER_07 54:46

Yeah.

SPEAKER_04 54:47

Thank you.

SPEAKER_06 54:48

Thank you.

SPEAKER_04 54:50

Great episode.

SPEAKER_06 54:53

Let's go home.

SPEAKER_04 54:54

Thanks for listening to Unbottled. If this episode got you thinking about plastic, systems change, or how we build a better future, don't just be a listener, be an owner. Kadea is raising a community round on WeFunder, and that means you can invest as little as$100 and help us bring closed loop beverage systems to more people in more places. Because real change doesn't happen alone, and the future of hydration needs all of us. Learn more and join our investor community at WeFunder.comslash Kadea. Let's build it together.