A Discussion About Founder Depression and Wellbeing with Gabe Zichermann

Hey everybody, welcome to this webinar. My name is Jonathan Gritchen. I'm a co-founder of the Founder Institute, and I do see we got a bunch of people joining in now. Welcome to everybody. We're expecting a pretty, pretty international audience today. Please, at any time you have questions or comments, let's, let's get them into the chat. We're here to, we're here to have an open discussion with you all. And we have an interesting topic today. And before I introduce the— our speaker, let me talk quickly about the topic. So according to a UCSF medical study from 2015, 72% of entrepreneurs actually report mental health concerns. And founders are also 30% more likely to experience depression from non-founders. And if there's anybody on the line here who has been an entrepreneur, who started a couple of companies— and our guest today has started 6 companies, so he's got a unique take on this— but some of these statistics is probably— they're probably not going to be too surprising to you. As an entrepreneur, you are expected to fix every single problem. You're expected to work every single hour. You're not expected to complain about it or, in a lot of cases, share some of the challenges that you're going through because you're supposed to be the fearless leader. I think the fact that a lot of people don't share some of these challenges can be super unhealthy. And just for me in particular, right off the bat in my entrepreneurial career, I've lost 7 teeth. Every time I had a toothache or something, I was working so hard, I would just yank it out, deal with it later. I've also literally almost worked myself to death. I had internal bleeding where I lost half my blood and I spent several days in the hospital and they never figured out what the cause of it was, but I was working 100, 120 hours a week. Weeks for years at that time. And, you know, I definitely hit the bottle a good amount as well. And I think you'd be hard-pressed to find any entrepreneur that doesn't have, you know, kind of similar stories like that. And at the same time, a lot of people don't share it. So what we want to do today is sort of talk about these things in a little bit of an open setting. And let me bring on our speaker today, which is Gabe Zickerman. Hey, Gabe.

Hi. Hello, hello, hello.

So the reason why I really wanted to bring Gabe on today, just in addition to all of his positive qualities, is that Gabe wrote an article. And Virginia, if you could paste this into the chat, it's at the top of our doc. Gabe wrote this article a few months ago, 2, 3 months ago, about a term he was coining, startup psychosis. And honestly, it really just struck a nerve with me, and I know that this is something that I wanted people to discuss. So Gabe is a 6-time entrepreneur, used to run our New York program, public speaker, and anything else you'd like to share there, Gabe?

Yeah, sure. I mean, I started my first company when I was 16 years old. It's a very like classic story, and that promptly fell apart and failed. And I've started 6 total companies, since then, of which 2 have been successes, and the rest have been more or less a shit show of different proportions. And along the way, I've also, as John said, mentored a lot of founders, both through FI and other means, and I've just seen this— the reason why I felt animated to write this piece in the first place was because it feels like this kind of silent cloud, you know, that's like following our whole industry, all the people I love the most in the world, it kind of like sits over top of them. Remember that like Peanuts character or whatever, where the rain would always come down on top of them?

Yeah.

And, but I do wanna say at the start of this conversation, if anybody who's watching, you know, feels like they are in imminent danger, the National Suicide Helpline, and the Crisis Text Line are two great resources. You can quickly Google them and get in touch with them. And, you know, it's not just for, you know, it's not just for poor, uneducated people. It's for, you know, all people who experience any kind of like extreme distress. Please look them up.

Yeah, please do. And, you know, to further that point, neither Gabe nor I are medical professionals, okay? So, you know, what we want to do today is, yes, if you are having any thoughts of hurting yourself or anything like that, please do get help, please. And towards the end of this webinar, we'll start opening up to people in the audience as well to see how they've gotten help. But really the goal here today is let's just share this stuff openly, okay? Because whether you are at that level or you're not, you know, it's sort of a slippery slope. And the more people can be open about sharing some of the challenges they have, whether it starts with their friends, their family, whomever, you know, the better off you're gonna be. And right now, I think as an industry, as you said, Gabe, it is sort of this cloud going over everybody's head and few people talk about it. And I think especially, You know, at least in my opinion, a lot of it just has to do with sort of this machismo, you know, killing it, Gary Vee type of, oh my God, yeah, that's Fuck Fridays, hashtag Fuck Fridays culture, which I, as a marketer, I find that very creative but also very damaging. But anyway, so why don't we start getting into some stuff here too? And let me just give a quick also note on Gabe because he's being sort of You know, he's being sort of respectful in this, but he's— if you've ever heard of a term called gamification, Gabe basically coined that term. And Gabe has been one of the leaders on gamification his entire career, and he's written a bunch of books as well. So check out gabezuckerman.com. He's done some, some really amazing stuff. And Adeo and I know him back from our New York online gaming days and have stayed in touch ever since because he's a super smart guy and amazing speaker, and you should check out some of the stuff that he's doing at gabezuckerman.com.

Thank you.

All right, so, um, so Gabe, you know, one of the— and I was, I was citing some of these statistics before, right? We're saying 72%, and, um, in that post you actually, uh, what you said was that every single founder that you've met without exception has a story of mental illness or some other major psychological problem that you've seen. That's a strong statement. I mean, how do you, you know, do you want to dive into that a little bit? I mean, you think every single entrepreneur you've met shows some sort of behavior?

You know, let me just tell you an apocryphal story that helps illustrate this. You know, 10 years ago, I'm hanging out with a bunch of entrepreneurs in New York City, And we're working on a bunch of stuff. New York is a very collaborative entrepreneurial ecosystem for those of you who don't live there. So people hang out a lot. We had a lot of meetups. We were doing lots of things. And I'm in the room with the guy who legitimately had sold a company for $150 million the year before. My biggest exit was closer to $40. So this is really somebody, super, super bright guy, like really, really quick. And we're just hanging out and we're talking about startup stuff. And he just casually is like, yeah, I don't think I'd be able to do this new startup without Provigil. And I was like, what is Provigil? I'd never heard of it before. What is Provigil? Oh, it's this drug developed by the Army to keep soldiers awake. So it basically short circuits your tiredness and keeps you awake for as long as the light is on. And I was like, how often are you using Provigil? And he was like, "Oh, every day. Like, how else would I get this done if I wasn't gonna do it?" And what was sort of surprising to me, what kind of triggered this kind of whole process for me, was watching both his casualness with it. And I'm not like, I'm not an anti-drug person. It's just, you know, this is like a real, you know, like a serious drug that should be under the guidance of a doctor, let's be honest. You know, like somebody telling you that they're injecting testosterone, right? It's not much different. How casual he was about it and how nobody else in the room seem to have a reaction to it. And then what I've seen kind of is the pattern over time, the more founders that I meet, you know, many of my closest friends are founders. Once you build trust, then you start hearing the real stories. Like, John, I had no idea you pulled your teeth out and had internal bleeding.

I never pulled them out myself, but yeah.

Yeah, yeah, yeah. But look, I never— you've never told me that. I've known you for some time.

I've never told really anybody that, at least not in those terms. I mean, I got a lot of missing teeth, but yeah, it's— and I think, yeah, the provisional stuff too. In spending a lot of time in Silicon Valley, I can tell you, it's not seen as a bad thing there. It's seen as biohacking. Yeah. There's even like a— Yeah. There's even a cool little term put on it. It's like, hey, no, I'm not abusing drugs. I'm just being uber productive because I'm killing it. Right.

Yeah.

Yeah. And so I know that you're speaking from experience here too, not just the people that you know, but personally, you did write in that article that you actually thought about killing yourself, right?

I did. Yeah. I think I've had two instances of— I never got to the point where I actually made a plan, where I said, like, this is what I'm going to do. Which, you know, most experts will tell you is a kind of scary trigger that you really need to react to. But, you know, I got to the point where I started thinking like, oh, this would be, it would be better if I was dead, where I feel, I feel like the world is being cruel to me because I exist and I should not exist. And they're to stop this kind of pain from happening. And for me, you know, the story which I think is easy to dismiss, but I have seen multiple times is that, you know, as you mentioned, I had this great success with gamification. I built these businesses, they worked really well. I was doing everything I wanted to in my life. Everything was great. And then I decided to do this startup to help people with their technology addictions. And it was a very like personal startup for me and very emotionally invested. And I raised a bunch of money from like great VCs who are friends of mine, like the whole thing. And then this business falls apart. And it's like, you know, the higher you climb, the higher, like the bigger the fall is and the more that that actually like, you know, ends up hurting you. And, you know, I remember like, I'm probably 2 days into a crying jag lying on my bed, not wanting to get up out of bed or do anything. And, you know, that's when I started having the thoughts. I'm like, this is just too much. And here's the crazy part. This was happening while we were still running the company. So this wasn't even after the company was fully closed. It was like, I could see that things were gonna fall apart. I could see it in front of me. And that's what triggered this extreme, this kind of extreme sadness and sort of depression. And it's important to note that there's two different kinds of depression, right? There's the kind of depression that is, let's call it based on legitimate facts that are happening in the world. Like if you lose a parent, it is normal to be depressed. If you end a relationship that you don't want to end, it is normal to be depressed. If your company fails, it's normal to be depressed. There's another kind, which is just this sort of baseline constant sadness that is divorced from events in the real world. but it, you know, the treatments may be different for those two different things, but the feelings are the same. So it is really, really profound and difficult. And, you know, and I still have these people who need me to come in and keep running the show. And, you know, I'm not sure that that's— I'm not sure if that helped or hurt, but it was something.

Something that I've always thought as well is that You know, just to give some of my personal perspective on this, there's a thinking in entrepreneurship that, you know, hey, it's great because you work for yourself, right?

Right.

But when you're building a team, and it's usually a small passionate team, and they've all bought into what you've, you know, to your vision, and they're probably not making as much and all this kind of stuff, right? Like, you're not really working for yourself. Like, you're always reporting. You're either reporting to your team that you've brought on, right? And it creates this enormous amount of guilt. right? Um, if things aren't going, uh, aren't going so great. Um, and for everybody in the, in the audience too, sorry, I should have said this before, but, um, definitely please, uh, if you have any questions or if you want to share any of your experiences, okay, because we want this to be an open, um, an open discussion. Number one, you can throw them into the chat. If it's something that you maybe are not comfortable putting your name behind, we looked into it. Unfortunately, in, um, in Zoom, a webinar attendee can't change their name, but you could also throw it into the Q&A. That way only our team will see it. And then also, if you do it in the chat, you can also select to only send it to the panelists. Okay, and I can, I can discuss it on screen and I'll leave the names out and all that kind of stuff. But please, you know, we want this to be an open discussion and we'll get to start getting to some questions shortly. So, so in addition to Well, first, I don't want to gloss over that dark part of your life too quickly. How did you sort of get out of that rut?

You know, honestly, psychotherapy. I mean, there's no substitute. When you, you know, from a lifetime of being dealing with mental health issues, I think, you know, this isn't unique to my startup experience. I've certainly been had periods of depression prior to ever becoming a startup founder. But it's like, I think psychotherapy plays a really incredibly important role in helping people be better. And there's various techniques that different therapists can sort of deploy. I think one of the challenges is finding a therapist who can appreciate the challenges of running a startup. This is a real it's really different from being a corporate employee, as many of you on this call understand, right? Like when you decide you're working some job at, you know, whatever it is, like Chase, you're working some job at Chase and you decide that you're not happy at your job, your boss is making you miserable, you know, you go to see a therapist, you say, I'm feeling miserable, they ask you about your mom, you finally get to the point where it's like you figured all that out, what's the advice you're gonna get? Quit your job. Okay, now if it's your own startup and you've thrown half a million dollars of your own money and your family's money into it, and you've gone out and become this like really public face for this idea, like this, you know, the anti-addiction startup Onward that I referenced earlier. I was on 60 Minutes in 2020, like with— I was on with Anderson Cooper, like pitching, you know, talking about my company. So it's a very public, very public, you know, project that I really put a lot of my personal credibility into. And I think it can be difficult for laypeople to really understand that. I think if you're not, if you don't personally perform at that level of exposure, if you're not constantly exposed to the world and exposed to failure, I think it can be hard to appreciate how serious it is. Yeah. And you know what? Everyone, I will also say this. I don't think that suicide, I think suicide is awful on the people who, you know, remain. But to give you some context, I don't have an anti-suicide bias, like a religious bias against suicide or anything like that. It's your body. You're free to do whatever with your body you want to do. It's just that like, when you take a moment afterwards and you take a step back from it and you go, was I really going to kill myself over this venture capitalist's money? Like, what am I— what? No, they're like the most sociopathic people in the world. Right? Like they take out insurance policies on you when they give you money. Like they're sociopaths. So it's like, you know, they don't care. You know, if I off myself, why do I care about their money? I don't know. It's kind of funny anyway.

Yeah. Well, I 100% see what you're saying. Like where A lot of times with an entrepreneur, you start with nothing, so you're selling yourself, right? Yeah. So your personal identity and your company become one. So yeah, it's not just like, oh yeah, that company, oh yeah, that didn't work out. Like, no, that actually is like, was you, right?

Right.

You didn't work out, right? Or at least that's the mentality that a lot of people have.

Well, most As you know, as we've talked about in FI a million times, like especially early stage investors, they're not really investing in your company because you don't have a company yet, right? They're doing it based on what they believe the market opportunity is and you. And so it's a very personal experience to raise that initial funding, very, very personal. And people are asking you lots of personal questions and you have to build a personal rapport And oftentimes founders are raising money from their family. Many of my friends, my family doesn't have a lot of money, so it's my own money that I put in. But you're raising money from family and friends. It gets exponentially harder when you have a weird fucked up relationship with your dad to go to him and be like, hey, can I borrow money? And then for my startup and he gives you the money and then your startup fails and then you're like 12 years old again. Oh, no. I crashed my bike. You know what I mean? Like, it's— there's a lot of stuff wrapped up in it. And so I think your point is really well taken, John. The startup and you merge in most startup settings, and that's what increases the psychological pain of anything bad that happens to the startup, for sure.

Yeah, it's really, it's really, really dangerous. And it's actually something like— so just using a Founder Institute perspective, we've had a really hard time building programs in Japan. Okay. And there's a reason, because culturally in Japan, your identity is so intermixed with your profession.

Yeah.

And it's a very similar thing. So obviously there, it's, it's for you to embark on building a startup in Japan and leaving a good corporate job, it literally could like bring shame upon your family, right? If you fail. And, but most companies do fail. Right. So, and that's where, like, Thomas here has an interesting question. Thank you, Thomas, for asking it. Like, why is it is so hard, or why do we think it's so hard for founders just to admit that they're human?

Oh my God. Well, OK. I'll just— here's like my 3-part answer to that, Thomas, because I have thought a lot about this. The first one is our industry. So I believe that being a startup founder is a profession in and of itself. Regardless of what your company does, startup founders, they end up being professionals. I wrote a piece called "I Am the Unemployable Entrepreneur." that I also posted if you're interested in it.

I like that one. I like that one.

That really lays out this idea that entrepreneurship is a profession. And I think that our profession is incredibly macho. I think you may have even used this word. It's a really macho profession and people like wear their, you know, they wear their toughness as a symbol of pride. So the first thing is your peers, the people that you look up to, they tell these outlandish stories of staying up for 150 hours or doing whatever it is that they needed to do in order to make it happen or divorcing their spouse or not having children, forgoing having children for 20 years, whatever the case may be, right? So you have this very macho peer group that is taking pride in how much pain they can evince. Then you have the, You have your investor class, and your investor class basically wants you to say, "I will do anything to get you a return." They wanna hear that one way or the other. They're trying to figure that out when they're looking at you, especially in early stage. Is this person willing to sacrifice everything to deliver a return on this startup? And I swear to God, they are watching that really closely. And then, you know, the third big external piece is, you know, the laypeople, the non-startup people who are around you. I'm sure for those of you who already, you know, been entrepreneurs, you know how high, in such high esteem people hold you. People will often introduce you and say, this is, you know, he starts companies. It's amazing. I could never do what you do. Right? So who are you supposed to go to? You can't go to your peers, right? You can't go to your investors who in theory could be your mentors. You know, your peers will judge you. The investors might throw you out of the company. You can't go to your friends and family because they just don't get it and they don't even understand. And you certainly can't go to your employees.

You don't want to freak them out.

Right, exactly. You're worried that they're going to go. So I think the tough part is that the classic, like, get help from your friends thing is very, very challenging for an entrepreneur who can feel boxed into a corner. And that's why just on a personal level, I will tell you, you know, I've tried to foster this vulnerability for a reason. The reason why I come out here and say I, you know, considered killing myself is because the only way to change the contours of this conversation is for people to start being truly honest without being macho about the challenges that they faced. It's not gonna change if we don't create a pathway, at least with our peers, for happiness.

For sure. And I see in the startup community as a whole, and so you were saying like, you know, just to put a little more light on this, people, if any of you follow like VC blogs and stuff, you'll hear it's a common thing is people are trying to find the next Travis, right? And that's—

Right.

Uber Travis. Travis was, at least in popular media, has been the personification of the entrepreneur that's going to run through walls no matter what. They're going to push this thing through, right? And created a pretty amazing company and made a lot of investors a ton of money. So, you know, you can't really fault him for that. But that is where, yeah, things can get— if that's the standard that they're holding people up to, it can cause some fairly personally destructive behavior.

And just think about— I think part of it is like, just think about if entrepreneurship was viewed as a profession. Okay. So if entrepreneurship was a profession like law or medicine or any other profession, being a train driver or whatever, you would expect there to— that your first gigs would build upon each other, right? Your first job, you're not a very good lawyer. Then you become a better lawyer by experience and repetition and over and over again. And there's a trajectory. And nobody expects you, a recent law grad right out of the gate, to argue a case in front of the Supreme Court. Nobody expects you to do that. But in entrepreneurship, we somehow expect you to go from a standing start and build Uber. And that's the standard that you're sort of held against. And it's important to remember that people like Travis, who I actually didn't know for a long time from New York startup scene. The funny thing is the victors write history, and people who have been very successful, when they tell their stories in the past, they tend to sugarcoat that. It's actually got a name in cognitive psychology, and it's self-enhancing transmission bias. or it's called the curatorial effect now in social media era. And so the idea is that you are selectively talking about your successes rather than your failures. You are whitewashing or you're success washing, as I sometimes call it, your failures and only talking about your successes. So what ends up happening is we look up to these people like Travis, but the story that Travis is willing to tell is a story of Travis being a superhuman founder. Who was able to overcome every obstacle in the world and was super brilliant and amazing. And when we compare ourselves against Travis, it starts to become difficult to do that, right? And to achieve that at our first go, kind of out of the gate. I think the central mistake is we need to stop trying to copy other people's successes and copy and learn from their failures instead. So that I think is an important distinction and we don't do that a lot in startup land.

No, 100%, because most of the time, yeah, you ask someone who built an amazing company, they'll go say like, oh, well, we just focused on the customer, right? Like, no, everybody focuses on the customer. That's not why you were successful, right? Yeah, like success washing, I like that. And I know that, you know, you've also, and Gabe also has done a couple projects around failure, a company called Failosophy, and I know that you've moderated a couple panels on this kind of stuff, and you'd mentioned that, you know, that there's this term called the rebound, right? This is something where you've seen a lot of entrepreneurs talk about how they built a successful company, and, you know, it's just— it's sort of the storyline that now I think has probably made its way into movies and all this kind of stuff around this myth of an entrepreneur. I'd love for you to share that, just because I think the audience will get a lot from it.

Oh, I don't know if this is a story that you're referencing, but for me it was very funny. I convened this panel of entrepreneurs who'd had a failed company. It was actually like a panel about learning from failure and embracing failure. And I had 5 panelists on the panel, and we organized it here in LA through StartOut, which is a great organization organization for LGBT entrepreneurs. And, you know, like 50 people came to this event and they paid money to come to this event. They signed up for an event about startup failure. And, you know, at the beginning, I laid out for all the panelists and everyone in the room, I said, hey, you know, we are not going to sugarcoat our failures. We're going to live in our failures for the purpose of this conversation and we're going to stay there. We're not going to say, and then that made me successful. I wanted to keep the conversation there. And man, oh man, like I could watch the audience. I was watching the audience, mostly aspiring entrepreneurs. I'm watching the audience as the moderator, and people were visibly uncomfortable, physically uncomfortable in their bodies with the discussion of failure. You could see the body and the people were really tense. They weren't like taking notes. They were like kind of moving around like they were being attacked. And then one of the panelists broke the fourth wall of our rules and actually pivoted the conversation to how she had turned her failures into a success, which is specifically what I did not want to talk about. And she decided that she wanted to talk about that. And the whole audience jumped on it. All the questions suddenly started going in her direction. The body language from people in the room changed. Everybody wanted to talk about how she had overcome her failures and not what it was like to go through the failure. What caused the failure? What did she learn from the failure? No, it was like she pulled herself up by her bootstraps and is a phoenix rising from the flame. And look, I get it. She, she, you know, we're under a lot of pressure. This entrepreneur is also, by the way, very successful entrepreneur, brilliant woman, person of color. Queer identified, that's a lot of stuff. That's a big burden to carry with you. And that might enhance your feeling of your need to control the narrative about your story. So I understand all that context, but I just think particularly as Americans, we are really, really, really uncomfortable with sitting in our failures. It's really, really hard for us culturally to sit in there and just like, you know, not try to find the bright side of it, not try to sugarcoat it and say, you know, it's fine that I lost everything in this terrible decision and I'm now destitute and eating ramen because honestly, that's what led me to start, you know, Rent the Runway, like whatever the story is, you know what I mean? And by the way, the story is never that. That is never true.

We really like a good story arc, right?

Yeah, it never goes like that.

All right, so we're getting a lot of great comments from the crowd, so thanks everybody. I'm going to start getting into some more of the questions here, and definitely, and this is understandably so, a lot of the questions are sort of like, okay, well, how can we start to deal with some of this stuff? Again, I'll just throw this out there again, we're not medical professionals, but let's just talk about this as entrepreneurs, like how we have dealt with it, how maybe some other people you might have dealt with it, and maybe that can help some people. One other question that I saw also as well, somewhere along the line was, if somebody was gonna go the route of getting a psychologist or getting medical help, you know, I would definitely imagine that it's— they're probably not going to feel comfortable in some cases asking their friends and stuff like that. So how would somebody, you know, just from zero there, like, start to look at that and find one that might be able to help them?

Oh, well, funnily enough, there are startups for that. So, uh, yeah, I mean, like Talkspace, for example, or BetterHelp. Those are two video-based psychotherapy chat platforms. You know, they're available both in subscription— they're available in subscription form, but like kind of low priced. You can get 30 minutes of help for probably something like $40. I don't know what the exact price is anymore. That is a great, very private way of getting help. Just go to BetterHelp or go to Talkspace, sign up for the basic plan, describe your issues. And I will, as somebody who's been in a lot of therapy, hashtag Jews. I will tell you that I think it's very important that you qualify your therapist according to the contours of your problem. And so one of the things that I would put in my, like, intake, because I always ask you like a little intake form, is I would put in my intake that I'm an entrepreneur and that, you know, I'm experiencing setbacks and challenges professionally, so that the therapist that's helping you has that as context, that they match you with somebody, um, you know, who has that experience. So, so it's like, um, you know, also I'm gay, so like when I find a new therapist, I prefer a gay male therapist because I feel like he will understand the experience that I came from. So I think you can learn a lesson from that as an entrepreneur and say, you know, want to find a, an entrepreneurial— or not a therapist who's an entrepreneur, but just one that understands that, yeah, I'm not simply going to be able to drop the mic and walk away.

One that has worked with other entrepreneurs and I think, and that is, you know, can see the world maybe the way that you see the world. And I would also even say there too, as you were saying, like entrepreneurship really is sort of a profession. So I would even separate that from like high pressure job. You know what I mean? I'm not trying to— Yeah, exactly the same. Yeah, it's just, there's just different components there that can, that can lead to some very different outcomes. So Ken was asking, do you have any recommendations on how to, you know, juggle all of the different things that an entrepreneur is expected to juggle at one time without melting down?

Okay, so we arrive at the billion-dollar question, which is— which is, I probably—

I probably should have led with that one, but no, no, it's a great—

it's, it's actually like a very meaty question. So I will tell you, if I had a simple answer for you on this particular problem, this webinar would have been exactly 60 seconds long. I would have led with that answer and we would have been done and there would be nothing else to talk about. It, from my perspective, it's so different that like, remember I, so I started these 6 companies. I did the first one when I was 16 years old. I'm now 46. It's been 30 years of working in this profession and My last corporate job was in 1999. So I haven't received a standard paycheck in over 20 years at this point. And, you know, even for me, each one of these startups, each one of these projects had slightly different contours, slightly different expectations, slightly different, you know, goals and objectives that I'd set for myself. And therefore, the solution for how to make them successful and deal with the stress actually evolved over time, both as I got older and learned more things about myself, but also the startup itself that, you know, that I was working on. So one thing I would be conscious of is there are as many different kinds of startups that you can start as there are different personality types. And not everybody is Travis, okay? So again, his story's not totally accurate, But not everybody is Travis. So if you are the kind of person for whom, you know, perhaps this is too stressful, I would encourage you very, very strongly, don't allow your startup to kill you. Find a different kind of startup that matches your energetic, your energy level appropriately. Like, you know, we often ask this question in startup land, What keeps you up at night? You've probably been asked this question. And just take a step back from this question for one second. It is such a symbol, an emblem of the disease of the thinking about entrepreneurship that we, with casually, without even questioning it, we're talking about how your company literally undermines the most important thing in your life for your health. Which is sleep, right? It's literally like, how are you sacrificing the most important thing for your longevity and health and mental well-being for your startup? And everyone just asks and answers this question like it's no big deal. And it's like, no, like, if you need 9 hours to be your most productive, you know, 9 hours of sleep to be super productive and intelligent and driven and motivated, then I want you to get the 9 hours of sleep because honestly, your startup isn't going to fucking go anywhere if you're getting 4 hours of sleep every night, but you need 9. You know what ends up happening after a while? You end up literally losing IQ points and making worse and worse and worse decisions. It's not like you can't push yourself past some of these appropriate contours of yourself and your own health. So I would say understand what the limitations are, understand your limitations, try to get those, and work your startup into what you are capable of doing. And by the way, small aside, especially for mental health, in this country, in the United States, nobody is gonna come and save you if you have a breakdown. Like nobody's gonna come and fix the hole that you've created by pursuing something that is, pursuing something in a way that's really negative for you. You must take care of yourself. I saw someone just post, like you gotta look out for number one. You must take care of yourself because nobody else is gonna take care of you. And I think that axiom is the one I would continuously return to, which is like, okay, well, whatever I gotta do for self-care here, I have to do it, whatever it is.

And on your point there too, about kind of building the kind of company that you think you can build, when you take venture capital, you're fuelling a rocket that's going to the moon, right? This isn't a, "Oh, this is gonna be great. I'm gonna have this great work-life balance." And again, nothing against taking venture capital. Incredibly, you need it to build a lot of companies, but just saying, as a personal choice, as the founder, when you take that money, you are signing up to build something of immense, immense value. Hyper, hyper growth, all that kind of stuff. So, you know, just something, just something that you should, you should keep in mind when you're doing that. Angel investment and things like that are a little bit different, but once you take the institutional VC money, it's, it's moon or bust, you know what I mean?

Yeah. And remember too that, like, um, you know, we, we often, um, look down upon, uh, we, we look down upon what are called lifestyle entrepreneurs.

Some of you, I'm sure, have received that as Yeah, it's like a derogatory term.

Yes, the derogatory term.

What's wrong with somebody hanging out by a pool making tons of money, you know, 6 hours a day or whatever?

I mean, right? Wasn't that the whole 4-hour workweek or whatever idea? But actually, in a meta level, like, zoom out for a second. You know, I've been very fortunate. I've gotten to travel to like 104 countries. I speak 5 languages. I have a very like global perspective. And sometimes this global perspective is essential for really understanding how to forge your own path in this complicated way. And one of the perspectives that I've been given from travel is that all around the world, people are hustling. Go to Lagos, go to Mexico City, okay? Go to São Paulo. People are on the street and they are hustling. They are walking. They bought 5 watches from some guy around the corner and he's walking around like all day long trying to sell 5 watches. That is a lifestyle entrepreneur. When you criticize lifestyle entrepreneurship, when you say, I found a balance, a stasis between the amount of effort that I can put in, my energy level, my mental health, the capital I have, and what I actually wanna do, which is basically what lifestyle entrepreneurship is, it's finding that balance, you're really missing out on the fact that all around the world, billions of us have been or are are lifestyle entrepreneurs in one way or another. So it's not like, you know, it's not like there's 3 different scenarios, right, of how this can go. You can either be Travis Kalanick, you can be the guy selling watches in Lagos, or you can be a corporate drone, you know, with no interest in being entrepreneurial. That's a false trichotomy. It's a continuum. And you have to find the place where you are, you know, you're happiest, where you feel the best.

Right, 100%. And we were talking about sleep here and Sarah had an interesting point. Sarah said she still views sleep as a weakness and she was sort of asking, you know, are there tips to help yourself go to sleep? I'll tell you right now, don't go down the Ambien route. That stuff is— Yeah. That stuff is the devil. So don't do that. But Sarah's asking like tips to help yourself go to sleep and to accept the importance of sleep. I mean, because she sees sleep as a weakness and for sure in entrepreneurial culture, if you're the person on Slack at 5:00 AM sending shit to the team, it's like, oh, it's so inspiring. Like this person, right? But it's not healthy. It's just, yeah. I mean, I don't know any tips there to accept the importance of it or just how to get to sleep.

So the first response that I would have is, are you a morning person or a night person? If you are inherently a night person, so you are somebody who does your best work late at night. Yeah, me too. I do my best writing starting at around midnight. So what I've learned over time is I need to adjust my schedule to fit the rhythm of my body. I am not a morning person. I don't want to take your meeting at 7:30 AM. And you know what? Like, honestly, it's complicated, especially if you've got a team coming into an office and you're the leader of that team and some people are morning people and you're a night person, you might feel like you have to be there in the morning. No, just say, I'm not a morning person, you guys. I'm going to take my first meeting at 10 o'clock. I'll be up really late. You know, this is what works for me. This is how I am. And I think maybe if there's one upside of COVID— I hesitate to say that— if there is one, it might be a little bit more appreciation for flexible working styles in the startup world. And so I think that's the first thing, know thyself and figure out whether or not this is actually something that is bad or good or something pathological in you. Then the second thing that I would say, and I love to sleep. So for me, it's never, I'm never like, I don't wanna sleep. I could go to sleep right now. Not that you guys aren't interesting 'cause you're very interesting. No, it's you need a dark room, it needs to be cool, it needs to be silent. If you can't get a dark room, cool, and silent, you're going to have trouble sleeping, number one. Number two, you need to not take stimulants in the afternoon or evening. It's very, very simple. Like, don't drink a cup of coffee at 7:30 PM to get you through, like, pushing through something and then expect to be able to lie down at midnight. That's not going to happen. And I think somebody mentioned Arianna Huffington earlier in the conversation. She, of course, would say shut off your devices, leave your devices out of the spot. I think that's also good advice that may or may not be right for you. I use my devices in bed until I'm ready to go to bed, and then I go to bed. And the last thing that I would say to you, which is a therapist told me once that I found very useful, is if you've laid down in bed and you're not able to fall asleep within, let's call it 10 or 15 minutes, you need to get up and get out of bed. You should not stay in bed and keep trying to get yourself to sleep, because you'll actually just make yourself more and more anxious about not being able to sleep and make it harder to sleep. So if you can't fall asleep within 10 or 15 minutes, just acknowledge that, get up, move to a different, space in your living space, read a book, an actual book, not a screen if you can. Read a book for a little while, you'll feel more tired, then go back to bed. That's a very easy solution for people who have trouble going to sleep. It's been very useful for me.

I'm going to try that tonight because that happens to me all the time. I usually put on a podcast or something, but yeah, even just moving.

Oh yeah, yeah, you could do guided meditation or whatever, you know, whatever might work for you there. But if you can't fall asleep after 10 or 15 minutes of trying, You got to get up out of bed. Cool. All right.

So we're going to, and we've sort of transitioned to this topic already, but you know, how to, again, like how to, how to cope, like, you know, the conventional wisdom obviously is to sort of share with friends, family, mentors, right? Um, somebody who's anonymous here asks like, how do, how do I communicate that I'm struggling to everybody? This is actually an FI graduate. So, uh, To whoever anonymous is, please write in to— you know, I'm not going to say the email here because I don't want to get spammed by a lot of people who aren't FI graduates, but you know the email to reach our team. Believe me, this is something that we see a lot, okay? And I was just talking about this on a webinar last week. We were talking about advisors and stuff. There's the shame involved, and a lot of times we won't hear from companies for months, even though we literally have like auto emailers checking in to make sure they're like, hey, can we help? Can you help? And then all of a sudden they'll contact us like, yeah, I'm dissolving. And we're like, shit, man. Like, why didn't you reach out to us? Right. So at least for Anand as an FI grad, reach out to us. Okay. Just email us and tell us. But, um, but what they're asking here is how do I communicate it? I'm experiencing burnout, but I don't know how to tell my team, my friends and family. I don't want to let people down and I don't want to make them think I'm using excuses?

You know, if I just was having a conversation the other day in, in chat with a former employee of mine, he was our data scientist and really, really brilliant guy. And he's gone on after Onward collapsed. He went on to this fantastic career. We really launched his career. It's one of the things I'm most proud of, you know, from, from that failure. Is what happened to him. And we were talking the other day, he did some really interesting work that— and we were arguing about it on Facebook. And, you know, we had a habit, he and I, of clashing. We would often kind of like, you know, come into conflict with each other. And all the things that were in that conflict were there. He, you know, he was my subordinate, and he grew up in a very hierarchical world. And so for him, you know, to question me was really hard. But I was also like, you know, you know, constantly not really fully understanding what he's doing, because he was doing something much more complicated than what I'm— what I'm— my pay grade, you know, like, I'm not a machine learning expert, you know. So, so we would butt heads all the time. And like, we have this realization on chat, and it's been, you know, a couple years. The other day, I just realized we were butting heads again. And I'm like, you know what, I said, you intimidated me. This is me talking to him. I'm like, you intimidated me. You're like one of the smartest people I've ever met. You made me, I felt stupid in your presence. And that made me combative and difficult. And I refused to listen to you because I was wrapped up in my own insecurity. And we had a good cry over text or whatever about it. And he was like, oh my God, I can't believe that. But the point is, Vulnerability, as hard as it is, and it's especially hard for entrepreneurs in the context of your team, vulnerability can only pay dividends. And I wish I would have been conscious of this with him while we were working together because I really fucked up, you guys. By not being able to access my own feelings and share them with him, I really missed out on taking full advantage of what he was able to bring to the table. I just simply wasn't present in the way that I needed to be present. And so I would say as hard as it is, you know, and you know, you might— people may not understand you. They may not get, you know, your vulnerability. They may find it disappointing or want to, you know, get away from you because you're being vulnerable. But you know what? Ultimately, the lesson that I've learned over and over again is that that pays dividends, full stop. I wish I could be more vulnerable. That's part of what I'm doing here. This is my practice. Yeah, you know, yeah.

And there was another question from anonymous too, which is very related. Um, how wise is it to be open about your mental health issues when you're the founder? You know, is this something that you, you don't really want to disclose until, you know, until you're established or something like that? I mean, I could certainly understand that, that sort of fear, right? What do you think there?

Yeah, let's be super clear, OK? There is no question that when you go out to people, whether you're an entrepreneur or not, like anybody in this culture, when you go out to people and say, hey, I'm not well, you know, I'm not feeling well, things are not going well, you get a wide range of reactions. You get avoidance, right? People don't like being around people who are not well. So then people tend to avoid— some people will avoid you. Other people may criticize you. Some people may dismiss you. You know, one of the things that I find very frustrating with conversations about mental health is that people will often say, like, they'll often say stuff like, reach out to people and, you know, get help, and that as like a solution to your problem. And it's like, well, you wouldn't tell somebody with cancer, like, call your friends up for a solution to your cancer. Good for support, but not necessarily an actual solution.

Right.

You know what I mean? So it's like we treat mental health as some kind of subordinate, less serious medical problem. Right. And, you know, if you had gallbladder cancer, which I hope you do not have, but if you had gallbladder cancer in the middle of your startup, you wouldn't be expected to keep that a secret from your team. Like, how irritated are we that it's obvious that the president has mental health issues and he's not disclosing them? Okay, that's really frustrating for us. Similarly, for your team, it would be very, very frustrating to know that that was going on. So I personally, I think you've got to be willing to take it on the chin. You know, that's part of being an entrepreneur. You've got to take the licks where they come. And in this particular case, I think you've just got to, you know, you've just got to go with your gut and try to be as honest and vulnerable as you can be. Sidebar, you know, you can also just keep it to yourself. That rarely ends well. So just FYI to you, it may seem like the right strategy in the moment, but the evidence suggests it is not.

And I've certainly been a victim to this where, you know, as a leader, you try to internalize the the stress, right, and sort of absorb it, shield it.

Yes, right.

From, from the rest of the team. And believe me, uh, this is for everybody, it's just been a stressful time, uh, the last, the last couple of months here for every— and it's affecting everybody in different ways, and certainly it's affected, it's affected me. Um, and definitely, yeah, when you're in that situation, what I found— and not, you know, I've probably made this mistake like 20 times, but you You just never really learn from it, I guess. But you absorb the stress, you think that you're doing a service to your team, but then really it ends up coming out in other non-pleasant ways to your team anyway. So you might as well bet you're better off just being vulnerable and being like, hey guys, I'm burnt, right? And I actually, I told my team this last week, I'm like, guys, I'm burnt. That's why I've missed a couple of meetings. I'm literally, I've just like, I've hit a wall, burnt, and I need a minute and I appreciate all your work. And that kind of stuff. So I do think—

Just consider this framing as well, which can be difficult for people who are single or don't have children. So let's say that all the negative energy inside of you, all the frustration, all the concern, all the fear, that you agree with John's assertion and my assertion that that is going to come out one way or the other, okay? That it doesn't simply get smashed down. Eventually it erupts out. Are you prepared to have the recipient of that be your children and your spouse? If you are not prepared for the people that you love in your life to be the ultimate place where this goes, and that in the worst possible case scenario, that you, you know, you kill yourself, that's like the most extreme pain that you can inflict on those people, right? So all that negative energy was blown in their direction. Would you be OK with that? And, you know, ask yourself that question seriously.

Yeah, because it's the exact thing that you're trying to avoid by using that tactic anyway, right?

Right, right.

You're just ensuring that it comes out in one fell swoop rather than maybe— Yeah. A couple other things here which are super related from Anonymous is, how do you break away, you know, this impostor syndrome, right? And this is sort of the nexus of a lot of the things we've been talking talking about, about these people that we deify sort of, and this behavior that an entrepreneur is supposed to feel so that they'll feel like they're an imposter when they feel how— in ways that they're not supposed to feel according to everything that they read and hear.

Right. Yes. I think imposter syndrome is often seen together. So imposter syndrome is the idea that you feel like you are unqualified to be at the level or in the position that you're in. And you keep that a secret, you believe that internally, and you say to yourself, if people only knew how badly I was doing this or how bad I was at this, you know, they would not love me or allow me to be in this position. That's imposter syndrome. And there's another phenomenon that goes along with this for a lot of high-performing people, which is what's called the internal critic. And the internal critic is a voice. It's often literally a voice. In your head. It is for me. That tells you you're stupid, you are terrible at what you're doing, you're lazy. So these are the things about the internal critic, whatever that self-critical kind of energy is. And just to put this into context, from the day that Onward started trending downward, for the next 18 months after that, I did not wake up a single day without the internal critic saying, you are a fucking loser. Like, it was right there. Often it would happen in the middle of the night. Like, if I got up to go to the bathroom, while I'm, you know, like, peeing, it would be like, you're a loser. So what you learn over time when you battle with your internal critic and you battle with imposter syndrome is you learn a couple of things over time. Number one, that voice is probably somebody from your childhood. It is the, amalgam of all the adults in your childhood giving you what they thought were constructive or helpful bits of feedback, but actually you may have internalized as negative. Like when I hear, "You're so lazy," I know exactly which adult in my childhood used to use that kind of language, you know, when they were talking to me. So it kind of gets fused in sort of early in childhood, and then it becomes a tactic, a technique that your brain uses to keep you safe and to protect you. It's got a valuable, you know, it's got a valuable role to play in your self-preservation. But what you need to do when you experience that imposter syndrome, when you experience that internal critic, the most important thing to do is not to try to fight it. Don't argue with it and say, well, I'm actually pretty good. I'm not an idiot. That doesn't work. The internal critic is an adult and it doesn't like to, you know, it doesn't bode well for you to argue with it. What you need to do is let it in. And you need to actually, when you start feeling that, you need to say, okay, so I'm feeling kind of down on myself. Why? Where's the cause of this? Where did this come from? Okay, no problem. And I know this is gonna sound very, very crunchy for many of you, but because I think a lot of these things happen when we're younger, this kind of drive and criticism and stuff happens when we're kids. One of the techniques that works really well is to talk about your childhood self and invite your adult self to protect your child self in those moments when you feel especially stressed out. So what I would say is like, you know, the critic says, Gabe, you're a loser and you don't know what you're doing. So then I say, okay, well, this is, you know, little Gabe. The childhood Gabe is hurt and he, you know, is being hurt by this. And I'm going to protect him as an adult and I'm going to accept his pain and challenges and be the protective adult for him that I can be. So I know that was super, super crunchy and sounded insane because I'm talking about like I was a little child and voices in my head or whatever. But if you can relate, if you can relate to any of those things, I think they're more common than people let on. And my core advice for you is don't try to fight these negative cognitive biases inside of your head with rational arguments. It doesn't end well.

Interesting. And just show yourself a little compassion, right?

Yes, exactly. That's a great—

because you're, you're you're comparing yourself to all of these narratives of how all these people— like, everybody makes it look easy, right? Yes. There's no such thing as an overnight success. I mean, you could throw all these kind of tired terms out there, but believe me, all the other people that have built successful companies, they went through the same doubts. They didn't just wake up one day and be awesome, right? And just come up with this brilliant idea.

Okay, with one with one qualifier, and we didn't actually talk about this, but I know we're running out of time, but just a small one. So some entrepreneurs are that way, the way that John just described. They're confident, they're, you know, they don't care. They're very able to do it. We call those people sociopaths. And some of the most famous entrepreneurs in history are clearly sociopaths. Mark Zuckerberg, sure, he's a lovely guy, clearly a sociopath. And when you come from that environment, what characterizes a sociopath is sociopaths do not care what impact their actions have on other people. They do not feel empathy towards others. So it's also important we have these, these guys in our midst who are very successful entrepreneurs. It's also important to contextualize that there's a bunch of mental illness there too. And you don't necessarily want, nor could you emulate that. Are reasonably healthy.

So now that's a really, that's a really good point. Yeah, there's an explanation for why.

Some, not all. Yeah, yeah, a bunch of them that are like that, and then the rest of us copy that person not fully understanding the demons that they're wrestling with every day. And I think, I think some like Zuck make it very clear, you know.

So we had mentioned, and we are going to wrap up in a minute here, you know, just, just before we wrap up, there were There were a couple of resources that you had mentioned earlier. What was it? Better Mind? That's with a Y, right?

BetterHelp. BetterHelp.

Oh, BetterHelp.

Yeah.

Okay. I had some other ones here too. So there's a crisistextline.org, a talkspace.com. None of these are FI companies or anything, guys. I know that a lot of people can— there's all the issues we talked about, shame or being shy or whatever. So these are all anonymous places that you can share some stuff. I found even just Googling last night a hashtag, #MyStartupStruggle, which I thought was kind of a cool thing where people are just, you know, some people have shared some videos and stuff about the struggles that they've had, and I think you can sort of scroll through and find some of those videos just to see that you're not alone, and vulnerability can definitely be an asset. And even just last night myself, you know, I shared some of this stuff on a Facebook Live, and it was sort of like a weight off my shoulders too, right? So it's, yeah, you should definitely share this stuff as much as you can, and don't be ashamed of it, okay? We're not all the Mark Zuckerbergs here or whoever. These, every startup journey is going to be a struggle. I think as soon as we started the webinar, what was your term? It was like each of my companies companies was a shit show to some level or other, right? Like, that's entrepreneurship now. It's all gonna be a shit show. It's all taped together with like super glue. You know what I mean?

Yes.

So even the successful ones are just a different kind of a shit show, but a shit show nonetheless. So, and for everybody else in the line, I just, I had a final question I wanted to give to you, Gabe, right? So again, like you've started 6 companies, many more than I have, and you've lived this entrepreneur's life. I think you said you haven't taken a real paycheck in almost 20 years or more than 20 years. Not a real paycheck, but a corporate fancy one. Yeah.

You know, when you're paying yourself, it's not a real paycheck.

Sure. You know, what's— if you could go back to 20 years ago, right, even if it was to your 16-year-old self or whoever, like, and now that, now that you know sort of some of the struggles that you've gone through professionally and emotionally and personally and all that, like, is there— what would you tell yourself?

I would say your, your optimism is your greatest asset. It's also a tremendous weakness. It's a tool that easily you use against yourself because when things don't turn out, you know, you, me, I blame myself. Like, I take all the responsibility for everything that happens, and I'm responsible. And so if I would go back, I would say, preserve that optimism, build a capacity for vulnerability, and remember that not everything is your fault.

Yeah. That's— yeah, I'm just agreeing. I wanted to add to it, but I think you summed it up there pretty nicely and concisely.

And to be clear, many things are your fault. So I'm not saying don't take any responsibility for anything. I'm just saying if you're the kind of like Type A high-achieving person that I am, you know, you are undoubtedly taking on more responsibility and more more credit and more credit for failure than you deserve.

Right. Some things will just fail. There's an amazing amount of luck involved.

No question about it.

In building a business. And you can sort of create your own luck by being in the right place and being in the right area.

Yeah. But there's luck involved.

Yeah. 100% luck involved. So a lot of it's out of your control. And I think just sort of enjoying the ride a little bit and knowing that, hey, It's not gonna be smooth. Definitely, even in just creating the agenda for this webinar, to me, one piece of advice I would give to people is don't try to be a perfectionist. I have found that to be a real struggle for me. I'm a perfectionist, and as an entrepreneur, that's not a good mix. Yeah, that's a good one. It is really not, and it creates a lot of anxiety no matter what you're building because it's it's not going to be perfect. And if you internalize guilt on that, it's going to keep you up at night, as you said.

All right.

So guys, Gabe, thank you. Thank you so much again. Check out Gabe's article on Gabe Zecher, Minnesotans Medium account. He writes a lot of interesting articles, but this was an article like— I don't— unfortunately, I hadn't reached out to Gabe in a while, but after I read this article, I reached out to him because I just, I thought it was important and it was something that inspired me to think about my journey, and I thought that it would be interesting for everybody else to hear that too. So Gabe, thank you so much.

Thank you.

Yeah, and thanks everyone for joining. We also will be doing a round 2 of this, not on this topic, but Gabe will also be joining another webinar next month on pitching in a Zoom environment. Maybe he can teach us how to get these badass backgrounds that he has, but you can check those out Check those out at fi.co/events. And thanks everyone for joining. I hope this, I hope this was helpful.

All right, thank you everybody.