Jason Calacanis: Hey everyone, welcome to this week in Startups Thursday edition. Today is a Molly Solo interview with Bonobos founder, Andy Dunn. Bonobos, of course, is the menswear brand. You actually might remember them as one of the original online focused indie consumer brands that hit it big in the early 2010s. You know, Warby Parker, Dollar Shave Club, lots more. Bonobos was eventually acquired by Walmart for over $300 million in 2017. But what you might not know is that Andy, the founder and CEO, lives with bipolar 1 disorder.

SPEAKER_01: And earlier this month, he published a book titled Burn Rate, Launching a Startup and Losing My Mind. This book is intense. It is super deep.

Jason Calacanis: Andy's very open and honest about his experience living with bipolar 1 disorder. He describes his manic episodes in the present tense. It's so raw is the only word I have for it. In our interview, we go super deep on entrepreneurship and mental health, the crossover in many cases between those two things. We talk about how founders are up to seven times more likely to suffer from bipolar disorders than the average person. We talk about how his disorder impacted building his business and his advice for founders and navigating mental health struggles. And of course, where he is right now. It's a super important topic. It's a really great conversation. Stick with us.

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SPEAKER_01: Andy Dunn, thanks so much for coming on this week in startups.

SPEAKER_05: Thanks for having me.

Jason Calacanis: I mean, I feel like everybody probably starts with the same question or some version of the same question because it is very rare to read a book by anyone that's as honest and reflective and raw as this one is. Like it is not a business book in the way that we think about it.

SPEAKER_01: But it's also just there are people who tell stories about going through things.

Jason Calacanis: But the reading about your process of literally understanding yourself, even as you describe what you went through is like remarkable. What was it? What did it take to write it? And then how did the experience of writing it change you?

SPEAKER_07: Thank you for that. I think that having gone through over the last six years, two to three therapy sessions a

SPEAKER_08: week with a great psychiatrist, psychoanalyst, therapist, you know, he's all he's all three of those, I think I did a few, I don't know, a few thousand sessions.

SPEAKER_09: And so it's a privilege to be able to afford good mental health care. And to be able to process in such great detail one's life.

SPEAKER_08: And the way that for me, that one of the primary challenges in my life has been navigating this journey with bipolar disorder type one, hopefully over time, enabled me to reflect on my own life journey in a way that was almost like an outsider looking at it, too. And I think that mental illness is terrible, full stop. And also, if we're fortunate to have something lurking in our own mind that we have found some kind of way to cope with or subdue, it necessitates an objectivity about oneself. Checking in what's happening with me? Am I becoming hypomanic, which we can talk about? Am I feeling depressive, depressed? Why? Is it something unexplainable? I don't know why I'm just descending. Is there something happening in my life that I'm not paying attention to? Is there something that I have is on my mind has been in my unconscious that is affecting me? How do I bring that forward? That journey was a privileged one to develop that muscle. And so, the book is the product of having a really good therapist to unpack my life with and rebuild myself with. Coming out of this second manic episode, Hospitalization 2016, I felt like I was Humpty Dumpty. I don't know if that's a relevant cultural reference anymore, but I was shattered into- I'm old enough to get it. Yeah. Thousands of pieces and I had to put myself back together. And I think in a lot of ways, the book is the, I don't know if it's a culmination of

SPEAKER_16: that journey, but it was an important step along the way.

SPEAKER_01: Yeah.

Jason Calacanis: I think the third party aspect of it, the sort of diagnosing yourself as you diagnose yourself throughout is what is particularly striking. There's so much to dig into here, but I think for our audience in particular, this kind of crossover that you talk about, like bipolar type 1 is pretty rare, right? It's 4.4% of US adults, I think, according to the most recent statistics, but reportedly seven times larger in entrepreneurs. What do you think that crossover is about? Have you encountered that? Have you actually uncovered a group of peers who have had similar experiences to you in all

SPEAKER_21: the ways? For sure. For sure.

SPEAKER_08: And I think, you know, let's say it's 3 or 4% in seven to one would, I guess, mean one in five or one in four entrepreneurs are dealing with this. It doesn't, it's a shockingly high number in one way. And then in another way, it makes sense to me because the up state with bipolar disorder, the state prior to mania, where you're experiencing psychosis and require, you know, typically hospitalization to bring you back down to earth. That antecedent to that hypomania is a mood state of rapid speech, lots of vision, new ideas, contagious, positive energy, very kinetic, high energy, all of that is like virtually indistinguishable from an entrepreneur who's having a good day.

SPEAKER_09: And so, in a way, the job of being an entrepreneur can cloak that underlying mood disorder and also perhaps like attract it as well.

SPEAKER_08: And I don't know what's the chicken or what's the egg, but it's not surprising to me that there is a high incidence of it. And I think I'm relying on other people, including the UCSF, which has a center on entrepreneurship and mental health to figure it out. But I think it's going to be the case for a lot of other kinds of issues as well. You know, whether we're talking about autism, Asperger's, ADHD, anxiety, unipolar depression, borderline personality, narcissistic personality disorder, I feel like really over-indexes and entrepreneurs, that might be 100% of us, right? And because, you know, you have to have a lot of delusional self-belief to decide you of all people are going to go build this thing. And so, it's a massive issue in our society. I would argue that 3% or 4% is still a lot of people. And I think the startup community is a great place to start, pun intended, because it's both disproportionately here and we're also in a unique position to be able to de-stigmatize it because we get a little bit more of a free pass than our counterparts in corporate America. It's like entertainers, we expect to have mental health issues and we sort of celebrate it. I think entrepreneurs in a way are celebrated too, right? You know, Steve Jobs, here's to the crazy ones, you know, the commercial from the 80s or Elon Musk, you know, coming on record with his issues. So, we have to take the privilege of working for ourselves and being able to build stuff

SPEAKER_16: and recognize, we're in a great position to lead the charge on disclosure. Right.

SPEAKER_01: It's true. It's a great opportunity for de-stigmatization and also just a larger conversation, it seems

Jason Calacanis: like, about this idea of neurotypicality. That, in fact, there are self-selecting traits for all kinds of things in life and that mental health, certain types of mental health might lead to this outcome. Like, I wonder how far can we take that? Does it mean, okay, you want to be a startup CEO early in your life, let's get you into therapy early, but also not therapize it out of you because you might build a great company? Like, it sort of gets a little fuzzy in there.

SPEAKER_35: Yeah, I, it's funny.

SPEAKER_01: Obviously, I'm not advocating for, you know, staying in a manic state. Like, your descriptions of those experiences are horrific.

SPEAKER_08: Totally. And look, with bipolar disorder, the hypomanic state that I described as jet fuel for the entrepreneurial drive, it also comes with great costs, impaired judgment. For me, I tended to want to do new things at our company rather than build the one we were building.

SPEAKER_16: You know, trying to build a software company inside of a pants company wasn't too smart. Trying to build a multi-brand empire inside of a single brand company that still had a lot to work on wasn't too smart.

SPEAKER_08: So there's a lot of costliness to even the hypomanic state. And the price that you pay for what I would call like, more access to that hyperkinetic energetic state is being depressed a lot of the time, where you can't really do anything. You can't, you can barely function. I barely wanted to live. So when we were developing the book, one person at the publisher was advocating for calling the book, here's the crazy ones. And I was allergic to it on three dimensions. First, don't ever compare yourself to Steve Jobs, even subliminally. Second, crazy is a complicated word right now. And third, let's not celebrate this. Let's just deal with it. And also let's not create, I think the flawed assumption that disorder and perpetuating it in whatever form is a critical and requisite ingredient in creativity and innovation. I think it's frequently correlated, but I think we're much better off if leaders who have this neurodiversity that they're bringing to the table are doing so with the goal of practicing self-care and good mental hygiene so that they can endure and be as balanced as possible. So I'm careful to say, I don't think I was a better entrepreneur because I had bipolar disorder. Right. I just think I was an entrepreneur who had bipolar disorder. And there's some good stories that come out of that and hence the book. But I am so excited to be building my next company on medication and in therapy because I just feel more steady as a leader. And I would like to believe, and I guess we'll see in my case, that I can do it, you know, do it again and maybe better and maybe be easier to work with for those around me, at least marginally.

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Jason Calacanis: And you mentioned, for example, trying to build a software company out of a pants company. Can you dig into that a little bit more? Tell us how it impacted the direction of the business and maybe ways that your employees weren't aware.

SPEAKER_53: Yeah.

SPEAKER_08: I mean, picture 2007, some time ago, 15 years, we were at a stage where there wasn't really a proof point of a brand that had been built, internet driven. There was actually even a debate where it was clothing even going to be sold online in a meaningful way. You know, Amazon fashion didn't exist. I know I sound like a dinosaur here. But we saw this company, Zappos, its own leader with a future, you know, tortured mental health story, selling shoes and selling shoes online. And that was a category that people said, well, no way, because you have to try shoes on, the sizes vary, half size, the width. And they figured it out and they figured it out in part by out assorting the competition by offering more sizes and styles, which you can do if you're aggregating demand on a national level in one store. And then second, and just as important, great customer service and customer service policies. So our insight when my brilliant co-founder started selling men's pants out of Trader Joe's bags, you know, on the campus at Stanford was, why don't we just build this brand digitally from the ground up if the future is the internet and e-commerce? And the pushback was like, well, no one has built a brand online first. And of course, that was music to my ears because I wanted to do something that others hadn't done. Well, fast forward five years in, and we've discovered that the software solutions available to building a e-commerce brand were just not acceptable. They weren't good. We kept switching. And so we, I think, correctly identified that there was a need for the entire ecosystem of new brands that were coming to life. So much better software stack and platform. And so I convinced our board that that was an awesome opportunity. And we raised enough money and we opened an office in Palo Alto, a company. The company was based in New York City at the time. And we opened this technology office and we put a bunch of money into it. And we hired 20 great software engineers and data scientists and UX folks. And we woke up two years later with just total show on our hands, where we had the New York office that was like, hey, we're building a brand over here. What are we doing over there? And we had the Palo Alto office. It's like, we're inventing the future of e-commerce. And Bonobos is the first brand that we're going to serve. And so we ended up with a situation where we had two distinct tribes of people within the company who each thought we were doing different things. And companies are hard enough. Startups are hard enough, as everyone listening knows, when you already are trying to do one thing. When you can't disagree, when you can't agree on what that thing is, and when it's more expensive, and when two different kinds of cultures are required, it can become a disaster. And of course, it turns out, there was an entrepreneur in Canada that had the same idea. And, you know, Toby built Shopify, and it's now $100 billion plus thing. And it makes sense that he built that because he's a software engineer who built a company that was focused on writing software for e-commerce companies. And so I think the hypomanic part of that for me was seeing an opportunity doesn't mean that your company or you are the right person to go address it. And if you have a delusional level of self-belief and the ability to cajole and conjure these narratives to life that other people can believe in, you can not only start a company with that skill set, but you can sink one too.

SPEAKER_01: Do the people who worked for you know this story? Did they know it?

Jason Calacanis: Do you think before the book came out? Like, I wonder, will future, you know, potential startup employees have pause thinking, okay, well, if startup founders over index for bipolar, what am I getting myself into?

SPEAKER_07: Yeah, I think that no, people didn't know what I was dealing with, because I didn't, which is to say I hadn't accepted it.

SPEAKER_08: I was in denial. I wasn't engaged in a healthy dialogue with myself, let alone a therapist, let alone friends and loved ones, family, let alone the company. And the only way people found out was when I was in crisis after this manic episode happened, let's see, nine years in. And at that point, I had 600 employees and it was a disaster. I spent a week in the psychiatric ward at Bellevue. I was discharged into handcuffs. I was arrested for felony and misdemeanor assault. And then I had to go to work like the next day, because I'd been totally gone and no one knew where I was. And it was really a hellscape for the next six months of figuring out if I was going to lose my job or had to step down navigating the legal system. Figuring out if I was going to get healthy and emerge from the depression that just surrounded me entirely following that. And was I going to make this relationship work with the woman who, my now wife, who I really rebuilt myself on the back of her love and acceptance and her accountability, which was like, you need to be taking medication and be seeing a doctor, of course. And at that point, it was like, you know, it's too late to have created a disclosure from a place of stability and strength. And so I think it's so much better to get out in front of this stuff and share these kinds of facts about our life when we're not in crisis and trust other people a little bit, which is to say, yeah, I think there are some people who would feel like that might be a bit much for them. But the truth is, once I did tell people, no one was that surprised, you know, so they were, it wasn't like, oh, my God, you know, people didn't know the stories or the extremes, but they knew me. And I think we have to give each other some credit, which is we're all already dealing with each other, you know, strengths and shadows included. So naming what other people are experiencing already, if anything, is going to make you a more approachable and connecting person and leader to be around. Right.

SPEAKER_37: I mean, we all know who our bosses really are. Shout out, Jason. Just kidding.

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SPEAKER_70: And not for nothing, you were also navigating an acquisition at that same time, right?

Jason Calacanis: Didn't the Walmart acquisition sort of started while all this was happening?

SPEAKER_08: We were at the beginning of a process of raising capital for raising another round and comparing that to strategic options.

SPEAKER_07: And there was an aftershock of that episode, what I would call like a micro psychotic break. My doctor called it like a mini manic episode that happened in the middle of the deal process with Walmart the following year.

SPEAKER_08: So like we were under LOI, we were negotiating terms. It was six weeks before my wedding and had a terrifying recurrence that I talk about in the book, not as bad as the previous year's hospitalization.

SPEAKER_07: I wasn't hospitalized, but it was clear that I didn't have the medication dosages right yet. I hadn't developed a sleep hygiene regimen, the one that I now have that actually my mom, it's my mom's innovation, which is every morning I send a sleep report.

SPEAKER_08: Um, of how, how much I've slapped a screenshot of my, from my Fitbit to my doctor, wife, mom, and sister, because with my bipolar disorder, sleep is such a sign or a trigger. As sleep is getting lower, that means I'm ascending up in mood as sleep goes up. That means I'm becoming depressive. My doctor says there's two kinds of depression, can't sleep and can't get out of bed. I'm the can't get out of bed varietal.

SPEAKER_07: So I still was in the, on the journey of figuring out like the mental health hygiene routine, you know, the, the ramifications of that, you know, mini episode, it was a very destabilizing time.

SPEAKER_08: And I, I sort of shudder to think of what might've happened. And, and I don't think there would have been any recovering if that episode had been more severe, if I'd been hospitalized, it would have been confusing because we were like negotiating the deal. Where did Andy go? And I was weeks away from getting married. So I was so freaking lucky to get through this whole thing, you know, to end up professionally with a great outcome for the company and a great owner, the financial outcome for all the shareholders, the fact that I was able to marry the love of my life who saw me through it, that she, that she would stuck with it, that I was able to get healthy. There are all these like vectors of good luck that I don't think most people are fortunate to have that confluence of things. And that was part of why I felt so fraudulent. Just a couple of years later, there was this architectural digest piece on my wife and me and our, you know, the beautiful wife and son and the beautiful apartment. And I felt like such a fraud. I was like, this is just not the story. This is a airbrushed, photoshopped, BS slice of my life that isn't even my life. And that's where I was like, all right, I'm selling this book. I need to tell the real story because the real story is so much more interesting and nuanced and textured and I hope ultimately more powerful and more redemptive and more inspiring for people on their own journeys with this stuff. Yeah.

Jason Calacanis: Tell me a little more about the triggers. You know, my closest friend in the world, her husband is bipolar and has had a number of hospitalizations and people in your life and you yourself become so adept at tracking these super specific triggers like one too many glasses of wine or not quite enough sleep. And then add to that the stress of starting a company. Like, can you even separate them out at that point?

SPEAKER_08: I think there is a, uh, there is an avalanche of potential information to be attuned to prior to it being too late. And I think the goal is how do we identify, self-intervene, have mental health professionals around us who can help intervene like before we get to that point where it's so hard for anyone to deal with it. Like, we've talked about sleep, I would also observe irritability, like I start to notice if I have this like rising anger that is sort of inexplicable relative to the conversation that I'm having, you know, I'll notice it now sometimes at work where I'm like, someone's disagreeing with me and I just get mad.

SPEAKER_07: And it's like, well, what's that about, you know, what, what's so threatening about that competing idea and oh, wait, isn't the job of a leader to be able to hear a dissenting idea, lead a discussion or a process and get to the best answer?

SPEAKER_08: Um, or is it kind of a job just to be right, to want your idea to be right? And so, I'll notice that if that's happening, that must mean that something like on the ego side for me is flaring where it's more about my ego than the company. And then I'll be like, well, wait, what's happening in my life? I'll talk to my doctor and it's like, oh, yeah, I've been drinking a little bit more. I've been working a little bit too hard. I've been kind of slingshotting around between different things. And it's like, oh, that's a hypomanic ingredient. And one of the, sure enough, like diagnostic DSM criteria for hypomania is irritability or overly goal-directed behavior. So, like, I remember I had one night where I was just hanging, I was attempting to hang framed pictures in our apartment. And I just like had to get it right. And I had to get it done before the end of the night. And there were nine. And I was making a mess of the wall. And then I was just like, what are you doing? And like, let's get someone that can do this or just let me do it. Give me the damn drill and like, I'll do it myself. And, you know, same thing. I spoke to my doctor about it. He's like, oh, yeah, like you're on a path there with goal-directed behavior. Or on the flip side, just noticing a little bit lower mood. So, I think it's like anything with human communication. We have to deal with stuff before it's like blinding light 10 out of 10 problem when it's a 2, 3, or 4. But we tend to not want to notice something when we're at the headwaters of it. And so, I think the job for me, you know, as someone with bipolar 1, is to be really vigilant about mood at the headwaters. And then to have the people around me and the medication and, you know, the doctor twice a week is a real privilege because every 72 hours, I'm talking about this kind of stuff.

Jason Calacanis: Yeah. I'm going to come back to that because you mentioned the privilege. What happens if you don't have that? Like, you know, how do we translate this advice for the startup founder on the shoestring, sleeping on the couch, who may be experiencing some of these things? Like you were in college. You described the college experience of, in some ways, seeming like just like a partying college guy, but who was on the edge of collapse, you know?

SPEAKER_08: Yeah. I mean, I think it's such a hard question. It's such the right question. I got a note a few days ago from a woman who said, how lucky you are as Latino woman, like how lucky you are that you can even tell the story from your perch of success. And as a man and as a white man or a half white man, um, and she's right, she's right. And I think I was sharing it because I, I don't, I didn't really know how to process it other than to be like, you're right. And someone shared with me, like, yeah, exactly. Like if you have privilege, you got to use it so that it can cascade. And, you know, I think we need to develop pathways for disclosure that aren't inside the organization that someone works because it's often not going to be safe. Um, you may not trust your boss or your company or, you know, HR. And so I think we've got to find a way to do what the mental health community does, which is have people who, um, have norms and rules of discretion, um, where they can't share things back that companies are, are paying for. And there is an ecosystem on the mental health tech side that don't quote me, but five years ago, what I heard was five years ago was a hundred million in venture capital went into mental health tech. And last year was 5 billion, which I'm like really excited about that because that means talent and capital is chasing after these opportunities. And hopefully a lot of those companies will be monetizing through working with the fortune 500, fortune 1000 companies who can help change the culture. So that if I am a manager at PNG, and I feel totally like I can't share my battle with bipolar disorder at that point, I'm not calling out PNG here, but you get it that there is a resource, you know, that I can go and begin that mental health care relationship with that the company is funding. And I think we have a reimbursement problem in addition to it being hard to find health mental health care, the out of pocket is too high. Um, so we offer things like dental and vision insurance, right? But what about brain insurance? Um, so I think we need to offer people pathways to health and self care that don't require them to have to make some kind of a scary bet with who they talk to and who they seek help from to the entrepreneur on the sofa. I would say, raise your round, um, and then tell your, tell your investors later, which is to say, like, vulnerability doesn't mean going all the way and right away. You know, vulnerability is strategic, there's power in it, but it is also potentially unmooring and destabilizing for the person hearing it because we're not all ready for it yet. Uh, so I would like to think that it's something that you could share, but I, I actually would share it after as a part of a get to know me and maybe have it be a get to know me that isn't such a surprise because you've alluded to it or like previewed it. Um, and so I think we have to stage disclosure situationally appropriate. What I would say is a real problem is if you are that entrepreneur on the sofa, not getting help elsewhere. Right. And I, and I've told everyone just charge your company. Um, you create a mental health stipend, $2,000 a year per employee, give it to everyone. And when you have three people, that's you two, the two of you and you know, your first employee, you can afford the six grand because if you don't fund your own mental health care, there is no company anyway. Yeah. So just make the, make a micro investment, whatever, make whatever enables you to get the care that you need.

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Jason Calacanis: Should that be, given the sort of Venn diagram of mental health disorder and entrepreneurship, but also the sheer stress of entrepreneurship, like, should that just be what every startup does and what every company does?

SPEAKER_08: I think so. Yeah. There's a very intrepid company called Real being built by a woman named Ariella Sephira. It's a mental health tech company. And I was just one day on LinkedIn reading their benefits because I was curious, like, how does Ariella do it? Who I know and got the chance to back her as an angel investor in a tiny way. And it was like, oh yeah, $2,000 a year mental health stipend for out-of-pocket stuff. Like, that just makes sense because we can't be waiting for, you know, these insurance products. Like, I think they're coming, but we can't be waiting for it. And I think Alexis Sohanian put out a tweet building off of some conversations from the book that he said, like, I think it will be table stakes in the coming years for venture capitalists to be providing not only acceptance, but support services, coaching, you know, things like that. And that makes sense to me a hundred percent. And I've got a small, like, small fund and we're doing a little bit of that, but I can't wait until we have more assets under management to just be able to pay for it because it's like, it's too expensive. It's really hard. Executive coaches are the same way. Like, the more you need them is at the beginning, the less you can afford them. I can remember being, having the first executive coach I work with pitch me on a $10,000 a month retainer. I was like, dude, I pay myself 70 grand. I can't pay you 120 to meet with me for breakfast once a month. But I ended up reeling him in with some options and figured it out. And it was a total life changer. He just, he just didn't have an economic model for his business that was right-sized to startups. Um, so I think the more that venture capitalists with influence and cloud and a network and management fees can help get in there and help entrepreneurs with this problem. Look, I think it's better for their returns to say nothing of their reputation in the long run.

SPEAKER_01: That's a really interesting point that it can start.

Jason Calacanis: It doesn't have to be the responsibility of the founder that it can start with literally like if I as a VC want to have a great climate tech company, I need to, I need to help my founder. I think we've built up such a, um, such a myth of, you know, the, the great man theory for her lack of a, for lack of a less dated way to put that, that we don't think of support structures other than money or employees or founders.

SPEAKER_101: A hundred percent.

Jason Calacanis: Um, I also, speaking of my dated reference, want to ask you about men because maleness and masculinity. Like you talk a lot about that. That's a big part. There's a lot of, you know, there's dad stuff in here, obviously, but you talk a lot about this sort of traits that are common in male entrepreneurs, the, the, the emotional fragility, the hyper competitive stuff. Um, are those also traits of bipolar one, one in women that you know of, or was this, is it basically because you are one, you are a man.

SPEAKER_78: Yeah, I, I am so, um, careful to extrapolate anything about female experience or what, you know what I mean?

Jason Calacanis: It's like, I mean earlier when you were describing the irritability, I was like, yeah, I look for that too. It's called PMS, man. Yeah. Look out.

SPEAKER_08: Um, yeah, yeah, no, that's, that's helpful to hear in an example of something where I don't know, I can only speak for me and I think, you know, at some peril we extrapolate it to being related to our gender or something.

SPEAKER_09: But I mean, look, I was a very insecure, competitive, arrogant being the corollary to insecurity mercurial person and far from fully formed and integrated and able to be able to talk about it at that stage of my life, which I know stands in contrast to the book that you read.

SPEAKER_08: Because the book is like post exorcism of a lot of those qualities. It's like the wrong term to use, I'm sure. Um, and it's like, not to say that they're not still there. They're of course latent. Um, but I think it took me a long time to realize there was a lot more power and strength in tackling head on, you know, those things that I thought of as vulnerabilities. Um, and it took a while to realize it's actually in my self interest to do that because there's more, it's far more connecting to hear from someone who you think is living one way that there actually is something different going on for them. So I like to tell leaders like it is self interested of you to share your vulnerabilities because it will be more connecting than anything in your, what you might think about as strengths. Mm hmm. Like people are, people will follow your, your vulnerabilities.

SPEAKER_09: They will respect your strengths. Um, but I think that's how you build followership.

SPEAKER_08: And so, um, you know, men are stupid. I think in a lot of ways, like we think the stoic thing is what's going to be winsome and it's just not, and it ultimately it's not winsome because if you can't do the work on yourself, it's going to be hard to be a great enduring leader.

SPEAKER_109: Mm hmm.

SPEAKER_48: And if you're doing the work on yourself, then there's no threat in talking about, you know, the vulnerable stuff.

Jason Calacanis: Well, I think they're, I mean, they're just fundamentally is that difference in community building and what is sort of allowed socially. If we stigmatize mental health, we equally stigmatize the idea of men asking for any help or getting together in a community and, and sharing their same experiences.

SPEAKER_01: Like we've got mothers groups and the chief app and, you know, I don't know, the network of, I'm dramatically generalizing here, but it seems like there's those two things really go together in some ways.

Jason Calacanis: Like if you're already vulnerable and you're stuck in this sort of hyper masculine trap where you can't ask for help, it just spirals. Totally.

SPEAKER_08: It's hard to be in community with others. Um, if we're wearing a mask and while I was writing the book, I only had a chance to read one other book just kind of came to me at the right time. A friend gave it to me, it's called falling upward by Richard Rohr. And he talks about, he's like a Franciscan friar. He talks about how until we're 40, we're trying to serve our ego and kind of wear this mask that we think is good for us and is what people want to see. And it's generally in service of trying to leave some kind of legacy or accomplish something or be good at something.

SPEAKER_80: Mm hmm.

SPEAKER_08: And if we're lucky enough, by the time we get to the age of 40, there is something that happens in our life. Out of nowhere that feels calamitous and unexpected, that just throws us on our ass and turns our life upside down. It's just sort of like the statistical nature of life that that will happen to you. Um, and it certainly happened to me. Um, I never pictured being in a jail cell, being arrested for a felony. It was like the most unexpected thing ever and that the gift of that moment, if we can harness it is it will lead us onto a journey where we come to realize that that mask was a superficial thing. Yeah. And then how do we take it off so that we might spend the second half of our lives in service to others rather than in service to our own egos. And the analogy he makes is like, it's like going from the center of the dance floor, you know, that, you know, that circle at a wedding. Yeah. And my wife hates that thing. She's Brazilian. She's like, this is so stupid. Americans seem to like show off their dance moves. And she just, and she's a great dancer, but she's like, this is so dumb. Um, I was the center of the dance floor person. Yeah. And now I share her allergy to it. And Richard Ward talks about like, just becoming a part of the general dance. You know, being in that room with everyone moving, but not being there because you need attention, but to feel the communion with others, to feel connected. And I think, um, yeah, women are better than that than men. And I think we, we have a lot to gain from, um, focusing more time on belonging and less time on being, you know, being in service to our own egos.

SPEAKER_16: Yeah.

Jason Calacanis: How does everybody just want to hug you? Like, I mean, I just wonder, like really, I mean, that's been my response. I mean, I'm very, everybody can tell you like a little, I do overdo it in the mom department, but like, you must still be in pain.

SPEAKER_117: This isn't a thing that goes away. Like how have people responded to you?

SPEAKER_53: Haven't gotten any zoom hugs. Um, you know, I was yesterday at, um, business school at Northwestern and it was kind of the other way around.

SPEAKER_08: There was a woman who said, you know, what do you recommend for someone who is the family in the family of someone with bipolar disorder? Hmm. And then she like immediately started crying. And I said, what I say now, when I get asked that question, which is, I think the first thing to do is to secure your own oxygen mask before you secure the oxygen mask of the person next to you. Which is to say like, you immediately have to think about taking care of yourself because you are now in crisis too. You are now facing a separate mental health issue, which is caring for someone with a mental health issue. And if you fall apart, quote unquote, you know, there's going to be no, you know, you can't be useful to someone else. And yet, when we have a loved one in crisis who needs all of our attention and is taking all of the energy, it's very unlikely that we're going to make time for our own self-help. Like we're now going to be like, oh, I got to find a therapist now. So I don't know yet the answer. I do know that I was so inspired by an entrepreneur who's building a company that is a text-based asynchronous app for people who are experiencing family members with severe mental illness. I, that struck me as so smart. Her parents have one parent has borderline personality disorder. The other parent has bipolar disorder. And so she lived it. And I was like, this is awesome because a asynchronous text app probably makes sense. Cause like you need help, but you're not going to go see someone. Uh, and as I was describing this, this concept of like, you got to focus on yourself too. Um, you have to create boundaries, expect, expect defensiveness. Like it's not going to work right away. Hopefully it's not a 16 year journey to accepting the diagnosis as I had, but it's probably going to be six weeks in a best case scenario and ultimately accountability. Like we can't just keep helping people who don't want to help themselves. Like at some point there has to be a conditioned element to the relationship. I think it's impossible for parents with their children, but I'm hopeful. Um, and she was just tears were just flowing. Like the room was quiet. There were a couple hundred people there. Everyone could hear her crying. It was so moving and it was more like, I didn't know what to do. And so on the way out, I was so happy to give her a hug. So I don't know. So instead people are bringing you their pain.

SPEAKER_122: Great.

SPEAKER_53: I'm feeling like hugging other people. Cause I'm hearing so much suffering and people who've lost loved ones. And by the hundreds, these messages I have. And I think most people haven't had the good fortune. Uh, and I'm not saying I'm not still in pain.

SPEAKER_08: As you said, some times, like I'm still a patient. I'll never forget that. But I'm, I'm one of the very, very, very, very lucky ones to be able to be metabolizing it as a story. Might we all be so lucky to be as fully known and accepted as I have been and felt in the last few weeks.

SPEAKER_09: So I'm in the giving hugs business. Uh, but I'm happy to take some too. So.

SPEAKER_124: All right. Zoom hug.

SPEAKER_09: Zoom hug.

Jason Calacanis: And this is where we should say that from your place of stability and self-examination, you are the CEO of yet another startup.

SPEAKER_08: I am. And I, it doesn't feel, it doesn't feel like stable by comparison. Like I think I was just, well, no, no, sorry.

SPEAKER_106: It feels by comparison to the last time, but. Okay. By comparison. No, no, no, no.

SPEAKER_128: By comparison to this.

SPEAKER_129: I'm like, are you writing the sequel right now? Because.

SPEAKER_128: Oh God.

SPEAKER_129: More than a hug here, Andy.

SPEAKER_128: Come on. No, no, no.

SPEAKER_08: But my, my point is that, um, it is a fundamentally. Mentally challenging endeavor, mental health, challenging endeavor, no matter what you're dealing with, whether that's having had a diagnosis and dealing with it, you know, which we need to be doing or just a general journey of building something regardless of, you know, diagnosed or not. Yeah. Um, so yeah, I'm feeling a bit overwhelmed today by our, our journey to product market fit and the stress finding it in the team, different opinions on what we build. Um, and clearly I, I live for the challenge.

SPEAKER_127: Um, I know I was gonna say, like, I say this with care, but is this wise?

SPEAKER_53: Um, it's probably not wise, but also like someone asked my wife that I think it was a journalist from Inc magazine.

SPEAKER_08: And she was like, I, you know, what else is Andy going to do? Right. You are, you are.

SPEAKER_16: And so like, if he's taking care of himself, then yeah, you should do, you should do him. Yeah. Um, so. Do you want to tell us about it?

SPEAKER_19: The startup?

SPEAKER_08: Yeah. Oh yeah. So yeah, it's called pumpkin pie and it started as a idea to find a, um, a partner for my mother-in-law.

SPEAKER_07: And so I was surfing as a 75 year old woman on the dating apps. And I was like, this experience is broken.

SPEAKER_08: And so we built a personality driven, um, app where rather than swiping on people's faces, you swipe on polarizing conversation topics. Um, and so it was like karaoke, cilantro, other people's children, Dave Chappelle, God, you know, like all these things that people have a strong opinion on. And then we built like a personality graph from it and we tested it and discovered it had zero predictive power in romantic relationships of any kind, at least in its early incarnation, but it was very predictive of two things, which are friendship and siblings. And so since no one needs an introduction to their sibling, um, we built a matching app for siblings. Um, we decided to focus on, uh, the contrarian idea of building a matching app for friendship, which, um, is a really cool problem. And we're, we're in stealth mode, which is what you call it when your product sucks, but we're having a ton of fun. And we're on a journey that I think we'll, um, we'll land at building something important. I love this.

SPEAKER_01: I was also thinking 23 and me is like 23 and me is the matching app for siblings from, uh, what I can tell from my friend group.

SPEAKER_87: Oh, that's amazing that you say that. I just heard a good fun story about that yesterday.

SPEAKER_01: Oh yeah. I've got one friend who has found, I think six sisters, six half sisters. Amazing. It's a scene. It's a scene. Um, this sounds amazing and I really want to use it. And I also just have to say that our producer slack just went crazy about the topic of cilantro. So like this, just clearly we have validated at least some part of this product market fit. Um, perfect.

SPEAKER_62: Andy, thank you so much for coming on. I hope everybody reads the book and takes support and lesson and, and from it and wants to give you a hug or get a hug, whatever, whatever they need.

SPEAKER_08: Either way, hugs are good. So grateful to be here. Thanks for having me. I'm wishing everyone listening well on their mental health journeys.

SPEAKER_139: Thanks for coming on.