Investing in Mental Health & Embracing Vulnerability with Andy Dunn

0:00and then there's the whole meaning meaningfulness what was it the three schools of Viennese psychology um and then search for pleasure man search for happiness man search for meaning and I think that there's that sort of like I think about my mom where I'm like I just want to be like my mom I want to I want to be as invested in my grandchildren as she is in my son I want to work out six out of seven days a week without fail I want to get seven hours of sleep like I want to have this um defining your terms social wealth mental wealth physical wealth

0:41and like if you've got three of the five there it kind of it does beg the question of like what is the goal of financial wealth and and I like your friend's Journey right which is that it is the output of having done something meaningful [Music] what is up you guys so excited to share this amazing conversation with Andy Dunn the founder of bonobos and more recently the author of burn rate launching a startup and losing my mind it was an incredible vulnerable conversation truly unique uh One of a Kind conversation that I'm just excited for everyone to listen to and hopefully benefit from I know there are a lot of people out there

1:25who have struggled under the surface with different mental illnesses a lot of entrepreneurs wrestle with this that I've talked to and I think this conversation with Andy will be truly eye-opening and really benefit a lot of people both on the building journey and afterwards as you try to improve your own life so without further Ado please enjoy my conversation with Andy Dunn well Andy thank you so much for joining the show today man this has been a long time coming I feel like I have been a big fan of yours from afar for for a long time and uh you know we're just now getting to connect thanks to our mutual

2:00friend Jim kunahiro pick shout out to him who who actually brought us together to to have this chat so super excited to have you and excited to dive into uh all of the cool stuff that you're working on and inspired by right now so thanks for joining thanks for having me excited to be here so you know I generally like to start these conversations with um you know this idea that I think of or call um the map of reality and you know this is like this general idea that we all have our own set of paths circumstances experiences Etc that kind of frame our map of the world and and how we view

2:35things and Pursuits that we've gone after things were inspired by Etc so I'd love to start there and just like set the stage a little bit before we get into all of your work and career and some of your your recent writing and Inspirations by just understanding a little bit about your background and path like what established your map of reality you know where did you kind of come from grow up were you entrepreneurial as a kid would love to just set the stage with that totally yeah I think for me the the origin story for me has to tie back to coming from a heterogeneous

3:10environment culturally you know my mom is a Punjabi Indian immigrant my dad's uh Scandinavian Midwestern American white dude you know we have this in common no I know I think this is part of why Jim connected us yeah I you know I but I don't think I put that together until just now I mean my mom is from Bangalore you know uh immigrant from from Bangalore India and my dad is a white Jewish guy from the Bronx so we are we're both part of the the half Indian Clan here yeah there we go and to make matters even more fun I'm now married to a Brazilian Jewish immigrant

3:43and converted the Judaism right before I got married so wow so you're a you're a Hindu then you're like me I you got that or I'm half Punjabi depending on how you want to talk about it that's that's a good one I've never heard that one before you know I am convinced that the uh you know like mixing of Gene pools and um you know like the G the uh the like genetic strengthening that comes with that is something that I'm convinced by I don't know if there's any research around that but everyone that I meet that comes from like mixed race backgrounds I just find have these like

4:17like super good looking or like really smart interesting like I just think that there is some strengthening that happens from the mixing of uh from the mixing of Gene pools so you've clearly done a lot of that which is fantastic yeah I mean maybe there's something to that I think there's also something for me that I've learned about just communication Styles and family traditions around communication I like to joke my dad's family they don't speak about small issues small issues become big issues and eventually you don't speak at all my dad doesn't speak to either of his siblings really my mom's family who are the big Indian family

4:55you say exactly what you think in real time to everyone except the person that you're thinking about so it's like a perfect exchange of information through gossip with Minima you know minimal conflict this is yet another thing by the way that we have in common I feel like we have this Eerie set of similarities in our lives now um you know my dad I haven't shared this really publicly in the past but my my dad uh was disowned by his family when he wanted to marry my mom um so my dad has four siblings I've only met one of them um you know I have first cousins that

5:25I've never met uh never met my dad's parents um I think his mom actually lives near me um somewhere in the in the general New York area I've never ever met her um in a similar vein right like small issues become big issues when you don't address them um and uh you know and then there's too much water under the bridge at some point in life where it becomes really challenging to remedy those big issues so um yet another thing that I feel like we have a Common Thread in that uh in that vein yeah 100 and I want to hear more about that someday or at some point or we can flip

5:56chairs or something yeah but it did set the stage for me for a lot of transformation when I met my wife because in her family you say exactly what you think in real time to the face of the person you're thinking about so like the first time I had dinner with my now wife and mother-in-law my Scandinavian side was in the bathroom dry evening being like I don't think I can be a part of this family because they got in a quote-unquote fight which I've turned out you know turns out it's just a spirited disagreement um but I came out of this heterogeneous context culturally you know religiously

6:30it was fascinating because my dad was a Christian but was lapsed really became agnostic when the Swedish Lutheran Church that he belonged to um basically everyone left when black people started moving into the Austin area of Chicago so he was like well this isn't very christ-like you know we have some kind of racial diversity emerging and let's get the hell out of here right which mirrors a lot of the challenges we have in in modern day uh religion which we could talk about and then my mom's family were you know not openly religious but pretty my Mom feels pretty connected spiritually so I came out of

7:06this environment where it was amazing because I had so many questions I had so much stimulation you know from from different places and everyone I was around was homogeneous right like I was I was the only quote-unquote person of color in my school you know until until one you know young black man showed up from Cabrini Green on like an exchange program which is at the time where were projects on the near north side of Chicago so had this really amazing mixture of identities you know to navigate was it amazing growing up or was it a challenge like did you did you feel um you know as a kid it's like fitting

7:48in is the most important thing in your own mind you're like I want to just fit into a group and it's you know you want like I remember struggling to just figure out was I a jock or was I a nerd was I you know brown or was I white like what what was I and how did I Define myself like was that a challenge for you or did you feel like it allowed you to kind of toe the line and be in many groups it was both it was both an asset and a liability as is the case with so many things in life I wasn't really that

8:15aware of it um until I got to an age where there there was this sense of otherness that I began to process around being half Indian or you know being singled out as different um my my real wake-up call on it was almost getting my ass kicked at a bar in Ohio for being like a quote-unquote sand fill in the blank that was in college and that was the first time where I like I actually experienced the threat of physical harm for being Brown and it just blew my mind I had never really I'd never really thought about it as someone that could fall into Harm's

8:49Way which by the way is like 101 for skin color in some and so many other Stripes right um was that post 911 or what was the like it's just it's surprising I know no it's pre-911 huh um fascinatingly so you know growing up it was um I think it was both it was a sense of otherness in in to be honest I just avoided the Indian side of the equation like I distanced myself from what made me different and so I had this contrast where my cousin celebrated Hindu holidays they spoke Hindi maybe they spoke Punjabi they were really immersed in the culture because both of their parents spoke that

9:34language in the home and my mom was a rebel right my Mom married a white guy in the late 60s and my dad was a rebel because he married an Indian immigrant and so I was raised by people who didn't subscribe to the importance of cultural norms or homogeneity and yet I was in an environment where everyone was from one or the other world and so it took a long time to kind of re-embrace what made me different and I probably didn't want to go there even in college because I went to college in an environment at Northwestern I was in a fraternity where it was mostly white guys right and and

10:08it was there actually were Jewish guys you know what's called Jewish and not Jewish because I don't want to describe the rest of folks as Christian but yeah I was in a fraternity called Sigma Chi and there were so many Jewish guys in the house that we used to joke at Sigma I had that at Stanford too yeah so um you know that that's a bid on my origin story I think I guess I think I would think I would add is I have an older sister who I'm really tight with and that was a big part of my upbringing was having this like protective Overlord

10:40female presence and same thing with my mom's family where she has four you might know the name like four mossies which is a endearing term for your mother sister and so I was just raised by a strong female environment and so you know at some point it occurred to me I was building an apparel brand named after a matriarchal great ape and I was like okay and by the way what makes bonobos the animals different is they have no violent conflict and we think part of that is because the women are in charge I definitely want to come back to that point there are two sort of through

11:16lines that you mentioned in in talking about your background that I want to I'm going to keep hammering on so I want to like call them out here one is the idea that something is both an asset and a liability um because I do want to come back to that I think it's a Common Thread um for a lot of things that we'll talk about and the other one is this idea of like early on distancing yourself from your differences like fearing being different and really wanting to um really wanting to kind of embrace um being the same as everyone else but then learning as you kind of go on your

11:47own hero's journey quote unquote to embrace what makes you different as the unique attributes that create your Edge and that make you you know the special person that you are and I want to talk about both of those because I think a lot of the listeners here will um you know really hear a lot about your journey and what you're working on today and where you've come from um and it'll resonate with a lot of people um you know it certainly has with me so um maybe we can transition as you know with those two in mind to talking a little bit about your path to

12:14entrepreneurship you got done at at Northwestern I believe in 2000 um and you didn't start bonobos right away you kind of had a journey from there to Stanford Business School um what was like were you an entrepreneurial did you have an entrepreneurial bent right away or did you kind of go down a traditional path first you know you have the the Indian uh Indian parent so I know they would have wanted you to do medical school or become a PhD or something so what was the path yeah I guess we're continuing your through line because my mom's side of the family the Indian side it was all

12:47doctors yeah which was you know one of the two ways to get a visa to the US my mom actually worked in ultrasound because she didn't get a chance to go to med school for reasons of her father uh being ill and she had to send money home and be a more innocent source of income because it's a little bit delayed as a doctor she never got to go back to India for her father's passing which is very tragic and then my dad is a U.S history teacher but his family there's lots of Physicians as well so my only Role Models growing up were doctors and then I won somehow the high school

13:19yearbook was like the most likely to be a millionaire I don't know how that happened I remember being like this is weird because I wasn't I wasn't particularly coin operated I wasn't one of those people with like a side hustle you know whatever mowing lawns or something like that and so it it took a long time to let go of that family sense of success which in my mind was tied to going to med school and so I actually went down the whole path in college I took all the coursework I was signed up for the MCAT and I was studying for the MCAT and I had this moment where I was

13:55like I just don't care like I had all these part-time jobs at a hospital I'd worked in the dark room and that was a thing developing x-rays the front desk of the emergency room got my EMT degree or whatever you call it and I just didn't want it as bad as my classmates wanted I saw how much harder they were working particularly three friends of mine who are now all surgeons and when you're when you're bumping up against people who care about something more than you do that's just a good sign that you you haven't really found your swim Lane yet you should be swimming in a swim Lane

14:30where you feel like you can go the fastest and you want to go the fastest if you don't want to be there then back to your word Edge you know you might have the edge and I might have had the edge like intellectually to get there but I didn't spiritually or will or drive wise and so that then invited this crisis of well if not this one thing I've been thinking about for 20 years then what and so I did what a lot of people do who don't know what they're doing which is I became a consultant you know I became an analyst at a consulting firm which I

15:03feel like is a way to delay you know it's kind of like a way to delay a decision yeah and that's where you met Jim I assume at Bain uh yeah yeah Jim by the way Jim is you know one of the most incredible mentors in my life I think he was he was a mentor to you he's also one of the most fun people I've ever been around like his ability to go out his he has the most infectious and hilarious sounding laugh uh in the world but um it's just someone that is like a true joy to be around at any point in time

15:35and so um I'm glad that glad that he brought us together in this context um totally funny story about Jim's laugh by the way we were at a bar night one night at the Sears Towers like outdoor bar that they had back when it was called that and Jim was laughing so much I think mostly because I'm that funny and um they we got caught he got cut off before he had a drink because he was laughing that way yeah like they thought he was like so hammered because his laugh was so big that they were like it's hard to describe other than that it sort of

16:06sounds like a dolphin call uh if you actually break it down I'll leave people with that but uh it uh it is a pretty unique and interesting laugh uh but an amazing person you know what one thing you mentioned um that I do want to hit on there was like um you know this this idea of like how you decided not to be a doctor because you realized you just didn't you weren't really in it you didn't really care I've always had this General framework um that I've been sort of like wrestling with recently of um sort of the idea that there is like a societal

16:38um like Max net benefit uh to finding the right thing for you to do and you know I'm kind of uh word gaming this a little bit in real time but basically the idea is like you could have been a doctor and I'm sure you would have made a great doctor you know you could have done you like put your head down grinded it out studied become a you know perfectly serviceable doctor and you probably could have impacted a decent number of lives right you would have saved some people you would have helped people they would have felt good um you know you could have changed a few

17:06lives that way but if that is not what you are like best equipped to do like not you're not you were probably weren't gonna be because you didn't care enough about it the top point zero one percent of doctors in the world but there was something out there that you were equipped like you had the tool kit to become the point zero one percent in the world at and impact way more people and at scale in a very different way you didn't know what that was yet but you kind of had an inkling that it wasn't being a doctor because you weren't pulled in the direction becoming like

17:35that true Obsession and nerd there were people that are and that's amazing for them to go and become doctors because they will impact tons of people and they will be so invested in it but you should always my framework for young people has always been that you should find that thing that you are going to have the unique ability to be point zero one percent at like if you're ambitious don't settle for being a consultant because you can be like a decent consultant and make a good living find that thing where you're like Circles of success or Circles of passion come together to make you uniquely qualified

18:07to go and truly win that game on a grand scale that resonates and I think what you're saying is even more nuanced which is you may not know what that is but if you know what it isn't you may have to walk away from what you know it isn't even though that feels like a safe and comfortable path to create the space to figure out what that what it is but that might be years later so for me it was effectively eight years from when I walked away from the idea of becoming a doctor to the beginning of the entrepreneurial Journey and there's a lot of confusion in that

18:49eight years because you've walked away from something but you don't know what you're walking towards and I think that's one of the hardest it's like breaking up in a relationship that's not working part of what makes it hard isn't the deepening awareness that you might not be with the right person it's the fear of the unknown on the other side and potentially having to start over I mean I had that hard experience I I mean Jim who we talked about I was working with him at an amazing firm that I had been at for you know the first six seven years of my career and I knew that

19:19I wasn't ever going to be the best at what I was doing there because I wasn't so invested in it the way that others were and there was this thing that I had started doing creatively on the side that I started to realize like oh maybe there's something there and it was the incline but I didn't know what it was yet it wasn't a thing and um you know over the course of a year or so and honestly with the mentorship of some great people that transition happened for me but the fear of that like oh my God I'm giving up something that is very secure very certain

19:48um you know there's a great trajectory to it there's a path in order to go after this thing that like I don't even know what to call it I don't know what it is um is terrifying in the moment when you do it I mean there's no other way to to describe it like the scarcity that we all feel of oh my God I'm gonna be broke which is so you know sort of misguided for 99 of people you're not going to actually end up broke you have skills you'll figure something out you'll be okay but that fear is so Primal uh when you're actually making that change

20:16totally I think it can be paralyzing and I think I wonder what is it about someone where they kind of cultivate the conditions or the courage to do that you know versus not because I do think the Paradox is that it all makes sense in retrospect and some of the happiest and most fulfilled people I know are ones who've taken those kinds of risks and succession and so I worry about I worry for the idea that you're taking Financial Risk when the risk is in fact spiritual which matters so much more you know yeah spiritual I mean happiness fulfillment like I just I would say I've

20:56generally and I'm sure you're in a similar boat like I've generally shifted what it means to me to be wealthy uh dramatically over the last year and a half like I just Define wealth so much more comprehensively than just being about money and financial gain and that's made all the difference in my life in terms of my happiness on a daily basis um which is a huge what have you added into that time I imagine having time yes I mean I would say I now you know and I've written about this and I might want to write a book about this at some point um and I'm going to need to pick your

21:25brain on the book process at some point offline um you know I would say today I Define wealth in kind of five buckets I think there's Financial wealth I think there's physical wealth you know Health Fitness Vitality mental wealth which I would kind of bucket um you know like General mental health mental Fitness like knowledge accumulation you know ability to learn and retain information I would bucket like spirituality and faith into that mindfulness um uh and uh and then time wealth um you know uh just the uh the general you know freedom freedom of time and then I guess the last one sorry of five would be um social wealth relationships

22:02people family um status uh in that bucket and so that's kind of how I would think about it more comprehensively I would say and my general mental model for this has been um you know the blind pursuit of financial wealth often robs you of of the other four forms of wealth and you don't want that to happen you know that's a that's a race to the bottom it's such a great point I know someone who recently has become extremely wealthy through a series of events and I I must admit some Envy you know that I felt less towards like just the sheer amount of money but more what

22:38I feel like I could do with it if I had that kind of money and then someone I know ran into him and was like oh man he looks rough and I really hadn't thought about it because I I met him recently for a meal and I was like it definitely has come at the expense of his physical health there's just no yeah I made a doubt about it I had dinner um recently with a close friend um who I won't name but um who sold his company last year for a billion dollars um and uh you know made probably 300 400 million dollars in the transaction owned

23:12a big chunk of the company um you know and basically went from like working on a salary on this thing that he was his baby for many many years to all of a sudden being extraordinarily like mind-blowingly wealthy get anything you want the rest of your life you're pretty young guy still too um he's single and I asked him I was having dinner I was like so are you much happier he's like well I'm definitely happier because it was a real grind um but I wouldn't say I'm happy like in a in an absolute sense I was like well why not he's like well you know I went

23:38on the like big you know trip after the sale and uh you got this boat and you know he had all my friends come out and everyone was so excited to come and celebrate that we did this and you know we're in there and we're getting on the boat and there's these two much bigger boats right next to mine and all the people are going and getting on those and the whole time I was just wondering like who the hell is that you know who got that boat like how is that boat so much bigger than mine and my friends are all looking at it being like damn that

24:02boat's sick my boat's not good enough and it just made me think like wow there's always going to be a bigger boat like to use the metaphor no matter what like if if Financial wealth is your scoreboard there's always going to be a bigger boat and yeah the reality is like we glorify it like you go to a party and there's 100 people in the room um generally speaking Financial wealth is the easiest way to like stack rank people that are there and so when there's someone that's extraordinary really wealthy there there's some billionaire in the room everyone is attracted they want to learn about what

24:31made that person so great and made so much well now if you flip it and you say like thought experiment let's imagine that everyone walks around with a happiness meter on top of their head and it tells you how happy the person is if you walked into that same room and you saw the billionaire and it was like a one on a scale of one to ten and you saw a you know an accountant who has a 10 I probably would go over to the accountant and be like what is your secret you because happiness at the end of the day is sort of what I want like I want

24:57fulfillment I want happiness money people think is a means to that end but it's a flawed one for sure yeah and then there's the whole meaning meaningfulness what was it the three schools of Viennese psychology um and then search for pleasure man search for happiness man search for meaning yeah and I think that there's that's sort of like I think about my mom where I'm like I just want to be like my mom I want to I want to be as invested in my grandchildren as she is in my son I want to work out six out of seven days a week without fail I want to get seven hours of sleep like

25:37I want to have this um defining your terms social wealth mental wealth physical wealth and like if you've got three of the five there it kind of it does beg the question of like what is the goal of financial wealth and and I like your friend's Journey right which is that it is the output of having done something meaningful but once it arrives it can be a very unhelpful yeah you know barometer in it yeah I mean realizing that is a huge step um and we'll talk about that in the context of your own Journey but before we get to um burn rate which I do want to talk

26:16about your new book super excited about and loved um can we just talk for a few minutes about the bonobo story um we referenced it in the context of uh of the of the gorilla um what was like the foundational Insight behind bonobos I mean what what was it you know you were at Stanford Business School I believe you met your co-founder there um what was like the Insight that that sparked it I think there were two colliding insights one all credit to my co-founder Brian spaley was men's pants don't fit that well you know we were coming off of the 90s and the 2000s where there was a

26:51revolution in the fit of men's denim stretch became a thing five pocket fit improved there were lots of different Silhouettes so people just started wearing denim and I think people in a certain demographic that could afford it started paying over a hundred dollars for jeans I remember the first time my dad was like I was trying to buy a pair of seven the original Seven For All Mankind genes and he was like a hundred dollar you know it was just mind-blowing yeah and so I feel like the fit of denim and the investment that men made in great denim paved the way for someone to do something comparable

27:25in pants and my co-founder was a savant and figured out this whole curved waistband thing that enables you to to fit your thighs and your butt in a pair of pants that also fits in the waist and he was brilliant about fabrication and the right kind of soft pinwheel corduroy that was to where we started the company in Northern California it worked for like the 85 degree middle of the day and it worked for like the 60 55 degree you know evening so that was sort of insight one was There's an opportunity to do a better fitting men's pant non-denim non-five Pockets so chinos and corduroys

28:00and then the other Insight was that Brands were going to be built on the internet and back in 07 this was very much not clear yet this was it was wasn't obvious and there was Zappos which we heard about was selling a lot of shoes but they were selling other brands the way they were doing it was category of soft goods was assumed it'd never go online like remember this is before Amazon had a fashion business and I can remember when Amazon went into fashion and the New York Fashion industry that I was a part of were like mocking it like oh they're never going to be able to do that so we were pre the

28:33big e-commerce platforms going into apparel and here you had you know this guy Tony Shea selling shoes by offering great return policy great customer service and having this highly energetic customer service team on the front lines and so my thought experiment was well if you can sell existing soft goods Brands online meaning you know fashion Footwear home why can't you build one and the more we pitch the idea the more we heard like who's done this and the answer was you know we didn't have an answer and that that of course became you know the beginning of the digital direct to Consumer brand movement which was very exciting to watch unfold

29:13because I think you know we got to we got to be a first mover on that whole movement you raised a lot of money um which I don't think I had appreciated um in just being kind of an outside Observer of the story I was a consumer of the of the product you know from my I'm trying to think what year you must have you must have started it but I you know when I was at Stanford I was there from 2009 to 13 and I think I started to First hear where about maybe in like 2012 or so and then during my early career years it was like you know the

29:41go-to um you know pants and product um but I didn't realize you would raise a lot of money along the journey would you have done that in hindsight you know do you think that was necessary um did it you know hurt or help in any material ways that you'd kind of flag for entrepreneurs that are just starting out today no I would I wouldn't have done it if I could go back I think there's so many problems with raising money I think the first is psychological which is that entrepreneurs can associate Capital raises with success and I prefer another construct now which is think of capital raising as a sign of

30:19failure like the more money you need the more open questions there are about the future you know business potential and and I think we could get nerdy about it but there's only very there's a very small number of businesses out there that are emerging that require over 100 million of capital and usually those are companies with asymmetric upside where the fundamental product is technology or software and I think that leads the second problem that Capital can create and try to solve for us was like there was no good technology stack for building our brand and so we added one of those like classic I had one of

31:02those classic delusional moments that you have as an entrepreneur where you're like well let's go build that like let's go build that other thing that actually has nothing to do with what we're currently doing and so we put a lot of energy and time and capital against trying to write better e-commerce software and it turns out that it's hard to write software inside of a pants company and it turns out there was a guy doing that in Canada named Toby and he's now got a company called Shopify I heard of it and that's that's what they do right and so there's this fine line between fantasy

31:32and reality as an entrepreneur and that line gets pushed out further when you have access to Capital yeah and then thirdly I would say you know most retail Brands aren't meant to raise a lot of outside Capital like retail is meant to be done profitably and I think the direct consumer world that's been built is a lot of profit losing companies and I think the the irony is that what could make a lot of those Brands great is really opening up their brick and mortar distribution not through company on brick and mortar which can work bonobos with 60 stores we made it work but actually through

32:09wholesale which is the relationship commercially that most DDC entrepreneurs frown on and if like for my sister's brand and the baby apparel space we're now live at Target we're live at bye bye baby we have a new partnership coming that actually is where you re you can raise money from from wholesale operating profit and and I think we've been through a decade-long delusion that I feel like I helped spearhead which is that a standalone direct consumer business is a good business it's not look at what's happening in the public markets and soon to be coming in the private markets and that you have to go It Alone pure play When

32:49the truth is that 80 plus of retail is still spent in brick and mortar stores and if you pick the right allies that can be a massive win and that was part of my logic of of actually selling the company to one of the probably the best brick and mortar company ever which is Walmart there's a lot of interesting stuff um in the bonobo story you know as we walk through it there that kind of traces the d2c journey and like what has happened in the d2c space like the early days of bonobos I mean there was a time when you could literally um you know any keyword in the world on

33:25social on Google you could put it in and like there wasn't anyone competing against you and you could acquire customers so cheaply and there was great Returns on acquiring customers in the early days on social and on those platforms now you know if you try to go acquire customers uh through Instagram so like you Toby actually tweeted something you mentioned Toby tweeted something hilarious recently that was like I think you could smash your face into the keyboard and have a hundred people competing against you at whatever jumble of words you know comes out jumble of letters comes out it's just gotten competitive everyone started flocking to that just like in any market

33:58and so it was interesting to me because bonobos was also early you know in addition to being early and thinking about d2c you were the first ones that I ever saw innovate around what a store looks like and you had I think you called them guide shops um your look shops but I remember going into my first one and being like wait what do you mean this is like I can't actually buy the clothing here it was like to experience it to see it and then they were sent to me direct um and now I think you've seen a lot of companies following on to that Pete you

34:28know there was the whole movement around owned retail where like you know um rent became the new the new CAC and there was like that whole meme around you know consumer Brands opening up all of their DDC stores and Soho like you know the streets were aligned with every single direct consumer mattress brand that decided they needed to open a showroom there or whatever it was um where do you think we are today so do you think um you know the d2c brand or the consumer brands of the future are going to be built in this um you know kind of wholesale or at least uh Channel agnostic manner like

35:01what do you think the future looks like for the consumer landscape yeah I think that the direct consumer part of the company what you said is perfect which is that the it used to be disruptive to bring in customers digitally and now it's just another form of middle person so when we when we launched an enterprising early employee of ours discovered that Facebook's ad platform was about to launch and we were one of the first 50 brands on Facebook's ad platform and so there was a period of time for a few years where that was interesting as large corporations which were suspicious of Facebook weren't on it

35:38and then as you had larger flows of capital in and people started to realize wait a second maybe this is going to be a way to spend ad dollars because back then it was like not clear that there was a great digital ad spent outside of Google and what was so interesting about Google was it's hard to advertise the je ne sais quoi of a pair of pants on Google it is a more utilitarian thing not that many people wake up in the morning and Google pants that make my butt look good right but if you're on a Facebook platform and you see a pair of pants that looks

36:11attractive and there's the right copy you have a more ineffable reaction which we used to think applied to let's say magazine advertising and fashion or whatever and now it turns out like actually you can do that in any medium that has imagery you which is why partly why Facebook became enormous with ads certainly Instagram as they brought that in and so you're right there was a period of time where it was there was Arbitrage and that that quickly changed and yet the Venture Capital Money pouring in to fund digital cpms basically turned Mark Zuckerberg and Larry Page and Sergey Brin into the landlords of the digital age yeah

36:53collecting rent on everybody collecting rent and by the way with far more Market power than your average real estate landlord right at least the real estate landlord world is competitive here we have yeah duopoly I would argue and I guess Amazon's getting into that game now so that's a scary player to have moving into that so you're right and I think as we learned that that wasn't going to be the thing and as I woke up to the fact that I had been imagining that a pants company and a menswear company was actually a technology company once I came to grips with the fact that I had been wrong and I feel like that's

37:30one of the strengths of an entrepreneur is being able to say like I was dead wrong about that that thing I was shouting from the rooftops about two years ago was wrong that thing I raised my last round on turns out not to be true that that freed us up to go after not only our own brick and mortar but also in critically this relationship with Nordstrom and what was cool about that was we got to 100 stores within like 18 months yeah and super cost effectively and totally and you don't you don't own the inventory once they've bought it you've got National reach and so that's kind of my aha is like you

38:05don't need your direct consumer business to be the majority of your business you just need it to be the thing that tells the story that enables you to have a direct relationship with the customer and then wholesale actually is an amazing way to monetize that if you pick the right partners and I think the narrative even five years ago was well all those people are going bankrupt right like brick and mortar's dying software eats the world and the truth is Walmart Target Sephora Costco you know over General Dick's Sporting Goods Dollar General 25 billion dollar market cap company there is a react fundamental reality that the Lion's Share of retail dollars

38:48in in the United States are transacted in brick and mortar and you have a small cohort of DDC entrepreneurs who think for some reason that they shouldn't engage with that eight percent and and I'm seeing that start to evolve um in entrepreneurs who figured that out earlier by the way many of them are raising no money or very little money and I feel like that's the new playbook in GDC is get the brand to scale and GDC open up wholesale relationships thoughtfully strategically perhaps some brick and mortar and raised less than 20 million dollars certainly at the high end I was talking to a entrepreneur friend

39:25recently who started a um a consumer a food food business or like spices and foods and he was actually telling me that they make more money they make more margin dollars on an Amazon sale than on a website sale through their d2c website and I just thought that was so interesting because a few years ago the narrative was a complete opposite it was like man you gotta buy through d2c that's where I make all my money and I'm making nothing on Amazon Amazon's killing me and they're actually making more money and having better um you know actual delivery and customer service on the Amazon sales 100 I was

39:57just writing a note to two Founders where I we were talking about the delusion that we have around looking at gross margins rather than margins after marketing and so I have this nerdy metric now I call cpam contributed profit after marketing which is like what actually are you making in terms of before your fixed costs and most people are vaporizing all of their contributed profit on marketing so if you're spending 30 or 40 or 50 percent of your total revenue on marketing you're you're basically building a fundamentally worse business than anything you could do in brick and mortar yeah the last realization I have from what you said is

40:41um you know there's this tendency I think you were at Stanford Business School um you know you'd gone through Silicon Valley the tech Hub of the world like techno optimism everything um you were in this environment and I think now the world is sort of in this environment because we've had this 10-year Raging Bull Market of like this is what I'm supposed to do I'm a tech founder and you know I went to Stamford business school I'm going to start a tech company and what you do with the tech companies you go and raise money you go in Sand Hill Road and you go raise money from the VCS and then I'm

41:09gonna go become a unicorn and that Mantra and that story and narrative has permeated so deeply into the like entrepreneurial Roots globally that I think it only will happen in a bear market like what we're experiencing right now that we'll be able to break that and that Founders will think from first principles about does it make sense for me to raise money what is my use of this Capital does it make sense to take on the dilution should I prove product Market fit before I raise money because now I know what works and what I can actually deploy it into to grow um but I think that'll be a great thing

41:41and I actually think some amazing companies are going to be founded and built and the founders are actually going to own a bigger chunk of the companies when they you know reach maturity because of that shift totally and the other question can I can I even raise the money right because the market will help force that answer onto people yeah because it's it's quite hard and we started bonobos right and right before the Great Recession and so 0809 2010 we had to raise our first 8 million from 100 plus investors and so we had that forced Capital constraint and it wasn't until we had Venture Capital that I could pursue some

42:18of these other you know ideas and anyway we could we could I digress a little bit but I do think there's to your point enormous opportunity that gets created by the focus of um a bear market in terms of what it means for fundraising and by the way the valuations get more realistic too and I think that's a good thing for entrepreneurs in the long run although they don't they don't view it as such in real time I know I didn't sure so I want to shift gears a little bit um to your book and to really the message um and some of what you're sharing and

42:54the vulnerability that you've you've been sharing more recently You released a book um it's called for people who haven't seen it it's called burn rate launching a startup and losing my mind you can find it anywhere today I'll post the link when we share this and in the show notes you'll be able to find it it's fantastic I read it and I I found it to be um you know both deeply emotional um causing me to reflect a lot on the journey but also really inspirational um and I want to sort of dig in a little bit to that story if you don't mind um to be able to tease and kind of share

43:30for for other folks some of what you shared you know by by writing it um there's so much about the journey and your personal Journey your spiritual mental emotional Journey that you covered in the book um you Embrace a level of vulnerability in the book that I think is basically unprecedented I would say from an uh from an entrepreneurship standpoint I've never really read a book where I felt like someone shared that much rawness um of their journey and of the ups and downs of that Journey every now and then you hear it maybe from creatives from you know writers comedians Etc but I have never seen that you know from an

44:08entrepreneur um and I think it was a beautiful thing that you shared that so what what inspired you to write this book what was it I was tired of being ashamed you know I spent 20 years living in secrecy with this illness and you know we talk back earlier about belonging and difference and I think one of the ultimate forms of difference that one wants that I wanted to keep hidden as a severe mental illness who would want to present that information to others if they didn't know it and that's the way our that's the way our culture determines what's shameful implicitly is what's unspeakable and so if you can't talk about something

44:57what I internalized from my inability to talk about bipolar disorder was there must be something to be profoundly ashamed of that there was something fundamentally broken in who I was that I was a disorderly person because if you have a disorder and then this horrible thing that we do with mental illness which is that we say someone is bipolar rather than has it imagine being told you have cancer versus you are cancer it's like unimaginable to tell someone that they're cancer um and yet that's what we do with bipolar we we basically say your identity and this illness are now one and the same you actually are that

45:42illness and so that was a that hit me like a sledgehammer when I was diagnosed when I was 20. the the force of the slab Sledgehammer was met by the same level of energy that I put into denying that it existed so I spent a decade where it was really a suppressed memory didn't deal with it didn't take medication didn't see a doctor episodes during that period or was it largely not an issue it was it was latent um and that actually was really unhelpful in our diagnosing the diagnosing psychiatrist had said you know if Andy doesn't have another episode for five years it could be that

46:24this was a one-off event and I had I would say I had about 10 years asymptomatic and then if and that was after the first episode which was a manic episode which for people who weren't aware of it think about delusions of grandeur mess ionic seal incoherent speech Rapid Cycling of moods laughing crying ranting raving across while you were in college I was in college and so the sheer Ingenuity of my family got me to the hospital came back down to earth over a week you know a week of medication and then got out and everyone basically pretended like it never had happened well it was unfortunate timing but I had

47:11done mushrooms a few weeks earlier and so that was kind of the thing that everyone hung on their hats on and amongst my friends at Northwestern we know it was like Fight Club you never talk about Fight Club right like we all knew it had happened including me but we didn't talk about it and the fact that it wasn't spoken about was to me a source of Shame and then it wasn't until a decade later when I fell into like fearsome depression as I was navigating co-founder divorce and the trials and tribulations of building a company that I started to experience the other side which is just catastonic

47:47depression didn't could barely get to work didn't want to live and and you would think at that point that the that it would start to compute but it wasn't until you know 2016 where I had a really the second meaningful manic episode hospitalization ended up you know at Bellevue in New York City for a week and and walked out finally ready to deal with this and and walked out straight into handcuffs and was arrested for a felony and misdemeanor assault and that that began you know the process of of really confronting this and um a credit to my wife and a credit to my doctor and credit to a family that

48:26rallied around it I got through it and so to your question on writing the book I felt like the normal thing to do having dodged the bullet of almost anyone knowing about this would be to say nothing but the the thing that I would be condoning if I did that was the fact that this has to be unspeakable and so I felt it would be a disservice to the community to not share given that I was lucky enough to get through some of this stuff and I felt selfishly like I just wanted to expunge the shame and so the way to do that is to say I'm

49:03going to actually put the whole story on the record because there's this wasn't my fault and if it wasn't my fault then this is just a story about something that I've been through um and it's been beautiful it's been beautiful how accepted I feel I feel like a fully known person for the first time so there's so much you said there and I appreciate you sharing so openly you know there's so much you said that I want to dig into a bit one of the things that I just have this general feeling or realization around is that the way we treat mental illness in this country really globally

49:41um you know is basically like if we don't have to talk about it let's just not talk about it we're just gonna like hey oh yeah maybe that happened but let's just like push that aside I don't you know it's like very difficult for us to confront and so our response to that is like hey let's just not confront it it's fine you know Andy you were fine too you know it happened in 2000 or whatever year it was one-off episode and I'm sure your family embraced that you know Indian family I imagine um you know is challenging for and um that is such a negative thing

50:11um you know broadly speaking that we do that and and I hope that through sharing you know your story other people who have you know come forward and shared their experiences the people that your book inspires to come out and share their experiences I hope that we can start to kind of shift The Narrative on that uh more broadly a hundred percent yeah and it was this Indian side and the Scandinavian side too my dad's side it was fascinating that my my dad's mother actually had profound mental health issues and was institutionalized twice by her husband who had become a psychiatrist we we now think or my dad

50:48thinks partly because of his mom's issues and so here we had this like intergenerational family issue that you would think had opened up the con that would open up the convo but um it served to do the opposite it served to prepare us for the silence and I think this is what we have to invert in all these situations families at companies societally we've got to invert it so that we can have a conversation about things that are hard enough without the silence and the shame and I think we've seen that happen generally entertainment leads the way right like with with the gay rights movement you know we start with our

51:32entertainers right or even with with uh you know movement within the black community there's sort of like entertainment is first then Sports and I feel like business goes last um and and so I felt like if we could pierce the veil of the conversation in the business world in Corporate America where it's assumed that a steady hand is what's required shepherding Capital hiring Talent if we could pierce it there that could start you know a snowball a more meaningful snowball do you think I don't know if you've ever heard this um concept well I think it was Jerry Seinfeld was on an episode with Tim Ferriss and talked about the idea that

52:24um you come with like a kit in life you're kind of born with a kit um and for Jerry he was talking about it in the context of creatives comedians who have um generally in a in a population experience extreme depression um alongside this incredible creativity and intelligence that allows them to be exceptional at what they do and he calls it part of the kit he's like look I just have this kit and I experience these you know periods of downness and um and then these ex incredible periods of Flow State and Brilliance um that I that I work through you talk about a little bit in the book you know

53:01this idea of like hypomania um which are kind of the the upstates of bipolar disorder as I understand it where you have this amazing creativity and flow and energy um do you think that like to go back to the idea of asset and liability ability was was this an asset and a liability for you like did it also uniquely enable you to go and do these things that you accomplished and and you know create this amazing business and do some of those things I think we have to be careful I remember there was a moment in the process of the book where there were some folks that wanted to

53:37call it Here's To The Crazy Ones after the Steve Jobs commercial from from I think it was the 80s um or early 90s and I remember thinking I don't like that title partly because let's not celebrate or lionize craziness we do a disservice to the imminently sane people who are doing very creative and Brilliant things um so I wouldn't want to conclude that it's this like necessary requisite ingredient in the creative process but I would say there's clearly a correlation of it over indexing and that's in the data so three percent of the general population has some form of mood disorder most commonly bipore disorder we think that

54:23index is seven to one in entrepreneurs so we'd be talking about one in five and and that definitely resonates with me so for me was it a was it an asset and a liability absolutely this hypomanic state that is before you're really going off the rails with Mania but that is a highly energetic state where you have elevated speech more Vision more ideas more excitable everything happens for a reason tremendous energy often for me anyway like a lot of extroverted energy you know five internal meetings in a day with the group three one-on-ones two interviews a press interview dinner maybe dinner was with a candidate then afterwards out and New York City

55:18was perfect for that and by the way it was it was totally fun it was dizzyingly fun and then these massive crashes that would come it wasn't alternating day by day it would be like three months of hypomania and then like three months of depression and I'd say look depression terrible for building a company you have to act when you're around other people you don't have positivity or ideas it's hard to get to work so I think there's something too aspiring for a more stable place and still allowing as my doctor calls it for like peak days and so I think that becomes the challenge and you know I'd love to talk

56:01to Jerry Seinfeld about that because here's someone who he's talking about you know the downsides no doubt that said I mean what a decade-long series or 12 years so there was like a prodigious amount of of positive mood State there as well and like for my part I'd rather trade some of those hypomanic days to trade away the depression um so it's a way of saying yes to your question with an asterisk of like let's be careful not to celebrate it or assume that it's a prerequisite sure so we're coming up to the to the end of our time and there are a few things I

56:36wanted to ask you to kind of to wrap this um wrap this all up and you know one of them is like we're not investing enough in this as a society we're not investing enough in mental health in supporting people who are experiencing these things in making people feel comfortable sharing in the way that that you did to your point it was like it was shame you know you wanted to hide it you didn't want to be different it was easy to um to just not talk about it and you know and keep it from the Limelight rather than embracing that difference to go back to that

57:07what should we what should companies be doing um to invest in this in resources to um you know to help kind of change the tune around this massive problem that so many people are experiencing under the covers yeah I think well here's the good news five years ago there was like 100 million in Venture Capital that went into mental health Tech last year I heard that was five and a half billion wow so the money's coming in and that could speak also to the Venture Capital glut that we've been talking a little bit about but there's been a lot more investment coming upstream and so I think what

57:44companies need to do now is is three things first create an environment where disclosure is encouraged I think that starts with leaders When leaders go first disclosing their mental illnesses their mental health issues and by the way you don't need a diagnosis to have struggled with your mental health you know as you know you don't get to a certain age in life without having had some things that you've really that have really almost um taken you down second is community so having a neurodiversity community group ERG whatever you want to call it where we can trade those stories internally and find a way to to identify

58:20our common experience and if you look at the span of it bipolar disorder is just a tiny part anxiety OCD grief addiction um the autism spectrum high functioning Asperger's unipolar depression which affects one in five people it's hard not to get a check mark on one of those as a person and if you assume one degree removed in families a hundred percent of families have got these stories so we got to build community around it and just make it normal to talk about it and then thirdly and the hard part is investment investing in treatment investing in care so that means actually having a relationship with Modern Health

59:02Lira one of these mental health providers that becomes a resource to your teams and then second reimbursement so the reimbursement rate says we all know on Mental Health Services are bismal you know they're they're not so great on typical physical medical issues and yet we have like dental and vision in part because that's not covered so let's take care of your teeth and your eyes but as for your brain best wishes and and yet that's like the stuff of how we conjure reality that's how we understand the world and so the pitch that I'm making to companies is treat this as one of your best investments

59:40because it's going to improve the productivity of your teams and that that means we need to do things like what my friend Ariel safira is doing it real which is she acknowledges that she's a mental health tech company the reimbursement rates are too low and so she provides a two thousand dollar a year per employee stipend for reimbursement of out-of-pocket expenses related to mental health wow and if a company with you know 50 employees can do that then we need to we need to call to action our Fortune 500 companies to make the same investment because we know that psychiatrists and therapists are not going to voluntarily

1:00:18reduce their rates we know they're not going to voluntarily join and affiliate with insurance companies that takes down their after tax and we know that insurance companies aren't going to pay more money than they currently do for reimbursement so the only part of the ecosystem that the money can come from are corporations investing more in the productivity of their teams yeah productivity and retention I I mean I imagine for your friend that drives a lot of affinity with the employee base that the company is investing in them and in their brains in that way so it's it's brilliant it out last um last two questions so one you know a lot of

1:00:56entrepreneurs are going to listen to this aspiring Builders investors Etc many of whom I imagine will or have struggled with mental illness in some way shape or form what advice would you would you give to someone who is going through this currently um and who is struggling I think um I think there's a two-step process the first step is to acknowledge it with yourself like to be in the conversation with yourself about it and I think that's such a remarkable thing to do like to even say the word I am depressed when you've never said it it's a big Journey because we attach a lot of

1:01:37significance to not being the kind of person that has that issue and so I think Step One is try to cultivate the courage to be honest with yourself about how you're feeling or how you're doing or what's happening to you and then once you've done that and maybe someone else helped you with it but once you've done that then the second step is to acknowledge that you're unlikely to be the person that can solve that on your own because otherwise you would have you know what I mean and and that's where the next big step is to go see a mental health professional and that starts with

1:02:13a simple simple talk therapist just go talk to one person that isn't your boyfriend or Mom or co-worker someone whose sole job is to find a way to get you healthy and that is the best investment that you can make and and I think that's like you're in the 10th top 10 percentile if you've acknowledged a problem in sought help and I think for most people you know remarkably um they haven't taken both of those steps yeah it's a scary thing to take that first step because you know we attach a level of shame to it the way you expressed earlier because we you know I

1:02:54think especially for people who are high Achievers and you've you know accomplished a lot you've graduated from some school and you feel like um you know from an external perspective your life is supposed to be great and I'm supposed to be happy and um why wouldn't I be happy I have you know a wife or whatever it is that you have in your life and you're supposed to be happy quote unquote and yet you're not and it's very hard to make that mental flip as you said um the other thing that I would say to to anyone out there is um just talk to your friends and ask

1:03:21them how they're doing like it's it's such an easy thing to do to just reach out to someone that you haven't chatted with in a while and just ask like hey how are you doing you know anything I can help with love to chat about Etc because one of the things about your story um that I find so interesting and compelling is you were on you know from an external view on top of the world like had raised 100 million dollars from Excel all these amazing Venture funds you had founded this amazing company you were selling it for all this money reading the news articles you're like

1:03:52man this guy's crushing it this is the most amazing he must be so happy um you know everything's good good looking guy you know everything right and yet you had you had this internal struggle deep deep struggle that you were wrestling with and so my whole thing has always been you never know what's going on behind someone's eyes so never judge someone because you don't know what type of struggle they are dealing with internally and always ask just you know reach out to people and say hey how are you doing because that small little thing might be the one step um that that kind of takes them to get

1:04:27help and to to improve their lives so so much to to take away from this conversation I um I found it an absolute Joy I I have to admit this was one of those conversations where I came away feeling like I can't believe I get to do this for a job so um I really really appreciate your time and super excited to get to do this in person and hopefully over a meal with our with our common friend Jim as well so Andy Dunn thank you so much where can people find you and um where can people buy your book yeah thank you it's awesome to be here

1:04:58and I would add one small thing to that check-in with people is be honest with other people when they check in with you we have this beautiful thing um in the English language anyway which is how are you and the typical answer is like I'm good how are you and I would encourage you to experiment with I'm not great right now and you'll be stunned it stops people in their tracks and it leads to some of the best conversations because see people are so surprised that you're actually being honest and so in addition to checking in with others role model being honest with them and sometimes that kind of frees up the

1:05:30convo in terms of finding me yeah I love I love to I love to be in happy places so email is an unhappy place for me uh because it's just work so I like to be in happy places my happy places are uh Twitter DMS um Twitter banter Instagram DMS banter there playing around with Tick Tock which is addictive and fun and then I love LinkedIn because LinkedIn I feel like is a great place to have iterative you know it's kind of like slack for strangers so I love LinkedIn too by the way that's like I've been where I've been growing the most recently I love

1:06:03LinkedIn it's really fun and then book yeah um would love you to buy it in an independent bookstore uh but if not amazon.com walmart.com are great places amazing well we will um we'll post everything in uh in the show notes so that people can find you and uh until next time I'm so so excited to uh to be able to release this and look forward to all the benefit that people will be able to take from it so thank you for thank you for writing this book thank you for all the vulnerability and congratulations on on the entire journey I look forward to hopefully being a part

1:06:35of the next phase of it amazing thanks so much thanks so much for listening to today's episode if you have any questions that you want featured in a future episode email us at hi T R W I h.com leave us a review at Apple or Spotify to help us grow the reach of this podcast until next time we will see you soon [Music]