BigDeal - #105 The Confidence Expert: How To Build UNSHAKEABLE Self Confidence | Mark Manson

Episode Date: December 4, 2025

Most people think confidence is about believing you'll succeed. Mark Manson knows better — it's about being comfortable with failure. After writing one of the best-selling nonfiction books of all time and spending nearly two decades studying human psychology, the author of The Subtle Art of Not Giving a F*ck has cracked the code on why Gen Z is struggling with relationships, why therapy culture might be making us worse, and why your emotions are a system that needs managing just like your business. In this raw conversation, Mark breaks down the alarming statistics behind today's confidence crisis, why dating apps are optimizing for all the wrong things, and how adopting labels as identity actually amplifies your problems. We dive deep into the hidden costs of success, why the happiest country in the world has low expectations, and the brutal truth about why 20-25% of Gen Z has cut off at least one parent. He reveals why AI therapy is both promising and dangerous, the single question that exposes red flags on first dates, and why marrying well is the highest leverage decision of your entire life. But this isn't just about what's broken — it's about what actually works. Mark explains why failure is the only currency that matters, how to stop being a people pleaser without being a dick, and why your bank account reflects the difficult conversations you're willing to have. If you've ever felt like you're chasing happiness instead of meaning, or if you want to build real confidence that comes from action instead of affirmation, this episode will change how you think about success, relationships, and the problems you're willing to have in your life. Thanks to GoDaddy for sponsoring this video! Head to ⁠https://godaddy.com/codiesanchez⁠ to get started with GoDaddy Airo® today I say it all the time: building real wealth doesn’t require a flashy startup — it just takes one boring, cash-flowing business. Join me at Main Street Millionaire Live to get my exact playbook for finding, buying, and scaling a business. Stop wondering how ownership could change your life, and come find out: https://contrarianthinking.biz/MSML26_BDYT ___________ 00:00:00 Introduction 00:01:16 The Paradox of Being Likable 00:05:19 The Dating App Crisis and Modern Relationships 00:07:45 What Real Success Actually Means 00:09:16 The Happiest Country: Low Expectations in Finland 00:11:28 Social Skills: The 80/20 of Happiness 00:13:21 Confidence is Comfort with Failure 00:15:14 Building Failure Muscle: From Small to Big 00:24:07 The Post-Exit Existential Crisis 00:27:33 Stop Labeling Yourself: Identity and Mental Health 00:45:07 Emotions as a System to Manage 00:48:37 The Why Game: Peeling Back the Onion 00:49:45 Therapy Culture and Cutting Off Family 00:53:48 ChatGPT as Therapist: The Malignant Narcissist Problem 00:56:27 Building Purpose: AI That Challenges You 01:02:40 AI Limitations: Brilliant Idiots 01:06:21 Choosing a Life Partner: More Than Romance 01:09:37 The Best First Date Question 01:11:18 Everything Comes with Bullshit 01:12:17 What Pain Do You Want? ___________ MORE FROM BIGDEAL 🎥 YouTube: https://www.youtube.com/@podcastbigdeal 📸 Instagram: https://www.instagram.com/bigdeal.podcast 📽️ TikTok: https://www.tiktok.com/@big.deal.pod MORE FROM CODIE SANCHEZ 🎥 YouTube: https://www.youtube.com/@codiesanchezct 📸 Instagram: https://www.instagram.com/codiesanchez 📽️ TikTok: https://www.tiktok.com/@realcodiesanchez OTHER THINGS WE DO 🌐 Our community: https://contrarianthinking.typeform.com/to/WBztXXID 📰 Free newsletter: https://contrarianthinking.biz/3XWLlZp 📚 Biz buying course: https://contrarianthinking.biz/3NhjGgN 🏠 Resibrands: https://resibrands.com/ 💰 CT Capital: https://contrarianthinking.biz/4eRyGOk 🏦 Main St Hold Co: https://contrarianthinking.biz/3YfGa8u Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode is brought to you by Tellus Online Security. Oh, tax season is the worst. You mean hack season? Sorry, what? Yeah, cybercriminals love tax forms. But I've got Tellus Online Security. It helps protect against identity theft and financial fraud so I can stress less during tax season, or any season.

Plans start at just $12 a month. Learn more at tellus.com slash online security. No one can prevent all cybercrime or identity theft. Conditions apply. Generally, people who feel like they give a fuck about way too many things. It's not an issue about the caring. It's the extent of how much they care. It's not about not giving what other people think.

It's about finding something that is more important than what other people think. If you don't have anything more important going on in your life, then what other people think about you is going to dictate everything else. Mark Manson, the best-selling author of The Subtle Art of Not Giving a B, is here today to break down how to stop faking competence and start earning it. You'll learn the psychology behind real self-belief, Why trying to feel good all the time is actually what's holding you back. If you've ever second guessed yourself or talked yourself out of taking a shot,

this episode is your playbook for unstoppable confidence built from action, not affirmation. The more you try to feel confident all the time, the more aware you become of all of the different areas that you're actually not confident. Stop trying to be confident all the time, that you actually feel comfortable in your pursuits, knowing that it might not work out, which is confidence. Confidence is really just the comfort with failure.

then how do you get more comfortable with failure? I will say this. I would say probably... I hate this answer. If you want to change your life right now, these are the habits that you need to start adopting. What are they? I think it's... I want to start with some of my favorite tweets of yours.

I just went down a deep rabbit hole. I haven't been in your tweets in a minute. I guess it's called X's. I don't even know what we're doing. I know. And so there were a bunch... You had one that you pinned that's like a new favorite of mine,

which is you said, paradoxically, the less you try to convince people to like you, the more likable you become. Is that true and why? I think when people try to make you like them, when they try to control your reaction to them, it is like inherently off-putting. I think we generally respect people who are, we generally respect people who respect our agency, right? So if I come in here and I just start saying all the things you want to hear and trying to impress you and like be like all what I, think you want to see, it actually puts a lot of pressure on you to make me feel happy and okay. And

paradoxically, that makes you feel bad. And do we not even realize that? Like, do you think people don't even realize the things they're doing to turn off other people? I think so. If you think about it, it's like a very childish kind of tactic. Like, I think when we're young, it's intuitive, it just feels intuitive of like, oh, I want people to like me. So let me just like agree with what everybody says. At some point that stops working and you kind of realize you're like, oh, I'd rather be disliked for who I am than liked for something I'm not, right? Because you just, you, you start feeling like even if you do get somebody to like you, it feels icky. And it's, it doesn't feel like like you're, you're being appreciated for who you authentically are. So, and I, and I think this,

this takes place on a lot of, I mean, obviously this is like a social phenomenon, but people do this in dating, you know, people do it with coworkers. They do it in business. It's like, you know, all the ass kissing, the yes men, like it backfires eventually. You know, it's interesting because we've had many a walk on whatever Venice Beach Boulevard or whatever that is, the boardwalk. And I think one of the reasons, you know, I like talking to you so much is you have this weird experience, which is that you've been on the internet for how many years now? I published my first blog post in 2007.

In 2007. And you've obsessed kind of this entire time in varying ways. it seems to me at least, about human psychology. And once through the lens of like men and dating, and you saw one whole era, which was like the, how do I get girls to like me era, right? And then you went through an era of like,

I don't care if anybody fucking likes me. Fuck all of you guys. And also how do I become confident with that and whatever? And so I've really appreciated your advice. So I'm excited that you're here because, man, we've both met a lot of people on the internet. Some of the advice is like sounds really good that it's terrible advice.

Oh, yeah. And you have like a very strong moral compass. Yes. You know, an ethical and moral lens, which you're like, no, I will not give that advice anymore because it's not real. Or, oh, hey, I did mess up on that. Sorry about that. Which is also really rare on the internet.

So I want to go through like a bunch of questions that I think about and then a bunch of questions from people who are listening. And I want you to take it through like a couple different eras. Like even the era of like, you know, now we're almost back again to how, do I get women to like me? Because it's been weird, honestly. Like, it's funny because I self-published a men's dating book back in 2011. And I just thought that era of my life was closed.

And it's funny because, like, Gen Z men are showing back up. And that book's starting to sell really well again. No way. So it's like, what was that one called? It's called Models Attract Women Through Honesty. And, and I wrote it, I really wrote it to kind of be the antidote to all the pickup artist stuff back in the day. You know, like, dude, you don't know. need to wear a fuzzy hat and like do magic tricks in a bar like you can just be a good human

being yeah and it's interesting because it's kind of catching a second life with the next generation yeah because they're they're having less sex they're it's a mess yeah dating's a mess right now yeah what what what is out there in dating right now what are you hearing from your millions of followers on all different platforms from what i can tell it's so i have a couple theories but like i i would say the primary one is, I personally think that the apps are negative ROI for people's dating outcomes. And it's primarily because they're optimizing for the wrong things. If you think about it, like I don't know how long you've been with your husband, but like if you think back to when, back when you were single, you probably had the experience of you would often meet somebody and it wouldn't

immediately occur to you. Like you wouldn't immediately be attracted to them. Like maybe you would talk to them for a little bit, get to know them, and then they'd win you over. Like, you'd have to like kind of warm up to them a little, a little bit. And the reason that happens is just that, like, we were poor judges of who's going to make us happy in a relationship. Like, we often don't understand the traits in a person that is compatible with us. And so when you get on an app, the app asks you for all these superficial traits that you want. It's like, oh, I want somebody who's six foot five in finance and like all this stuff. And it's like, it's all the resume shit that doesn't actually generate any sort of chemistry

or connection with somebody. Whereas all the things that actually do matter, you know, the personality traits and the background and the personal values and how the person experiences intimacy, the sense of humor, like all those things, they're hidden. So you can't match for those things. You have to meet the person first to understand. if you actually have those things, if you're compatible with the person in that way.

So I just think the dating apps have sorted for the wrong thing. And it's a classic case of people also not, because people don't know what they want, the dating apps are supplying a demand that is actually not solving the people's problems. Oh, man. So, I mean, I think in a lot of ways, everything you're talking about is about this.

Like, people want to find love because they're chasing happiness, You know, people want to find relationships because they don't want to be alone. Like, it's all sort of about what do we want as a human. It's like part of this human experience. And I'm wondering, like, I don't know, I think I read somewhere that you had written between books and blog posts. It was something while. You're like 17,542 blog posts. I don't remember the number, but it's a lot.

And one of the lines you said is that real success isn't actually about making money or being happy. What do you mean by that? Both money and happiness are, they're like oxygen. When you don't have any, they solve everything. But when you have some, it solves nothing, right? So yeah, if you're broke, go get some money. Like, that's definitely going to solve your problems. And if you're really miserable or depressed, then like, yeah, obviously get some happiness.

But if you're already kind of at a steady baseline, like you're in a stable position, chasing more. It's inefficient in a lot of ways. Like, it's not actually going to satisfy you in any meaningful way. I personally think that, like, on the long term, like, if you look at the, if you zoom out and look at your entire lifespan from beginning to end, the best way to define success is simply to feel as though you spent your time well. It's the old deathbed question, right? It's like if you, when you're 80 and laying on your deathbed, are you going to look back and say, like, I'm glad I did that? are you going to say like, wow, I wish I didn't do so much of that. And to me, that boils down to meaning and purpose, right? If you have meaning and purpose, if you were finding something

meaningful and purposeful in your life to pursue and to chase after, whether that's building something or, you know, starting a family or giving yourself to a cause, generally speaking, like, that's the sort of stuff that decades later we look back on and we're like, I'm really glad I spent time doing that. And do you think this is like a global phenomenon? Like you went to and spent time in the happiest country in the world, right? What did you find? Like, what do the happiest people in the world have? Or was it something totally else you found there?

Well, the funny thing, so the happiest country in the world is Finland. And the, if you talk to the Finnish, they're like, what? Really? And the conclusion I came to is that I think Finnish culture has this, this, they have this ethos of kind of low expectations, which is very opposite of how Americans are. But there's this sense of just being satisfied very easily. Like it's kind of a good thing to be satisfied. And I think that there's some wisdom in that, right? Like it's, this isn't to say that you shouldn't chase things or you shouldn't have goals or dreams or whatever, but it's also like have those goals and dreams, but also while

understanding that they're not going to solve anything. Like it's a fun game you're playing. Chase after that 10 year goal. Hopefully you achieve it. That's great. But just understand that like once you get on the other side of achieving it, you're still going to be the same stressed, anxious person who has problems and gets in fights with his mother. And like it's like it's all the you're going to be the same person with the same shit going on. So you need to like ultimately, find something that's worth the struggle. That feels like it makes the struggle worth it. When you're talking to, I think, predominantly a lot of young men on the internet,

and I love your YouTube videos, by the way. Thank you. Yeah. But you have quite a few where you talk about the habits that lead to, like, successful or happy lives. I know there's no hacks to any of this. And at the end of our three-step process, their life will probably be totally fixed. But if you had to give somebody, man, if you want to change your life right now, if you want to be more successful in life, these are the habits that you need to start adopting. What are they?

If I had a 16-year-old in front of me and my job was to optimize them to have the most healthy and successful life possible, I would actually start with social skills. because it's on the psychological side, like pretty much all of the research around happiness essentially boils down to the quality of your relationships. Do you have people in your life, A, and then do you have trusting intimate relationships with those people? Like, do you have people in your life that you feel like have your back, that you can trust, that you can go to with a problem,

who aren't going to judge you for making a mistake? And on the psychological side, that's like the 80-20. And then on the professional side, as you know, like relationships are also everything. Like it's nobody ever did anything great by themselves. Like there's no incredible successful business story that they did it alone. It's like you either built an amazing team or you had an amazing team of people backing you and helping you and supporting you. Yeah, I was reading a study the other day about how there's something like a 20 to 30 people. percent increase in salary just from thinking about increasing your EQ and really ignoring IQ,

that IQ almost has no correlation between monetary success. Do you find also in personal relationships, like I think a lot of people these days, you know, some of our top videos on YouTube, lately, I was talking to the team about them. They're all about confidence. And I thought that was really interesting because I feel like confidence usually goes away when you, like, or a lack of confidence goes away when you work a lot. Like the more you work, the more confidence I have. I rarely am like, we're not going to be able to do it. I'm like, we probably haven't prepped.

We haven't done sufficient things in order to have this outcome. And so I'm not confident we're going to hit it. But it does seem like we have like a confidence crisis. Do you see that with a lot of people saying, I do not feel confident in myself. I'm not going to be able to do it. I don't believe in myself. I have imposter syndrome. Yeah.

I feel like people definitely feel more scrutinized. and judged these days. And I think a lot of that is just how online and permanent everything is. You know, I think when you and I were young, if you kind of made a fool out of yourself, people would forget about it within a week or two. Now it lives forever on the internet. And people can like, you know, it's just everybody has a phone in their pocket. So it's anything dumb you do or say can potentially last forever. So I just think people have become much more risk-averse and they haven't built that muscle of taking risk. But the other thing, too, is I think, you know, I've always said that confidence isn't about believing you're going to achieve success. It's a comfort with failure. It's knowing that you're going to be okay if it doesn't turn out okay. Like that's actually what makes you confident in a situation. It's like, I'm going to take a stab at this. And if it doesn't go all right, that's fine. I'm going to learn from it. Right. And I just think a lot of people have that backwards. So they focus on like the guaranteeing of success. And so,

They become a perfectionist and they try to control everything, which then just makes them more anxious and more stressed out. And they get into kind of a downward spiral. That's a good point. I was really struggling to like nail what confidence is exactly the other day. We were literally just talking about it. And whether that's inherent or not. But if it is, if confidence is really just the comfort with failure,

then how do you get more comfortable with failure? Again, I hate this answer. I hate this for me. I hate this for everybody listening. Is this the only... Sorry, everybody. Is there not a three-step framework? God damn it, Mark.

Sorry. But really. Like, okay, so let's get granular then. Like, big failures, little failures, any failures, daily failures? All the above. And I will say this. I would say probably little failures first. I think it's...

Because big failures, if you're not used to failing, and if you're not used to failing, like it can overwhelm you and kind of wipe you out. But yeah, definitely you want to get lots of little failures in, lots of little embarrassments, lots of, you know, coming back to the dating coaching thing, one of the first things I used to tell people, I would say like how much have you gotten rejected lately? And, you know, most people would say not at all because they didn't ask anybody out. I'm like, well, that's your first problem. Like, go get rejected five times and then we can talk about what went wrong, you know? And people just don't think about it in those terms.

terms. They just think about it in terms of give me the thing to say that is going to guarantee that this person likes me. And the world doesn't work that way. It really doesn't. And it's almost like that in everything. It is. Like it's every answer is actually just, do you want to go get somebody to date you that you like? Go eat shit at least 100 times to find one. And it's like, and if you want to get rich, go talk to 100 customers that tell you no to get one. And if you want to buy a business, go look at 100 deals to find one. Every answer is basically quantity and more. And if you don't pile on more pain and failure, you're never going to have the thing that you want. Which is crazy. And you know, it's kind of interesting about you, too, like, you've done these

experiments with people. So as opposed to a lot of people who talk about things online, you're like, all right, I have a theory. And we're going to go test this theory live and see if the theory actually works and whether it breaks down. And you've done it as far as I can see with people who have lost weight in one way or another. People who were scared of failure. Like, maybe you could talk about one of the times that you walked in a chicken costume down Venice Boulevard, which I remember, and why? Because you put yourself through the experiment first, right? Yeah, yeah. One of the things I've always believed very strongly. Like, I've never, never wanted to be the guy on stage, like, telling this is what you should do. These are the five things that are going to change your life. I've always

like the idea of, like, I'm in the trend. I'm in the shit in the muck with everybody else. You know, I go through this stuff too. So in the videos, I do the same. I basically took fans with various anxieties or personal issues and kind of ran them through a gauntlet of different challenges or having them face their fears and whatnot. But I made myself do it too. And it was a good exercise, right? It's like, one, it's just I should be able to walk the walk of what I say.

But it's also, I think it comes back to like build. that you can call it scar tissue or you can call it the muscle but it's basically it's like that accumulation of failures embarrassments etc and it's funny because doing that series of videos by the time we got towards the end like I honestly reached a point where I'm like I don't think there's anything at this point that could embarrass me like or scare me careful if you put it out there you know I know it was funny actually so we just shot one a few weeks ago and it was funny

I basically hosted a dinner for a bunch of people in my audience and went through worked on a bunch of stuff with them and then took them outside and we were on the beach in Malibu and took them outside and then had everybody walk on

on hot coals and which is like a classic Tony Robbins thing and it was really funny because the attendees looked at me and they're like oh well you do this all the time right and I'm like no I've never done this before you're like it might work you might die And they are all looking at me.

They're like, what the fuck is wrong with you? And I was like, I don't know. I don't know what's going to happen, but we'll find out. Are you okay? Yeah, yeah, it was fun. But I like that. I was supposed to go to Tony's show the other week. Oh, yeah?

Yeah, I've never done it. Actually, that would, that gives me anxiety. Like, I've like, we've got. The fire stuff? No. Or being at a Tony Robinson. Like, hugging random people jumping up and down, smiling. Like, I don't know.

I've an opt out. And I say that with a lot of love to Tony who's going to come on the podcast. And he was like, come. And you know what his selling point was? Be in the front row. I was like, Tony, not a selling point. I want to be in the back. I'm unsure about this, you know?

But I couldn't end up doing it because I had some health stuff. But I do think that it would have probably been good for me because I hate that. I hate the idea of hugging strangers and jumping up and down. Maybe. You know, it's funny. Like a huge part of those seminars is that kind of like synthetic fun. And it's easy. I think it's one of those things where it's like easy for you and me.

Because I have the same feeling. Like I look at it and I'm like, really? Like we're going to dance again? Like what? Come on, man. Public dancing. Yeah. It's like, no, I don't want to give another back rub.

Like it's just. Oh God. You have to do backrups? Yeah. I'm like, I'm good, man. Like I don't. But it's funny because I think it's ultimately we're not the target market. Like, it's, if you think about somebody who's extremely depressed, extremely lonely, like, hasn't gotten out much, has kind of lost touch with most of people in their lives.

An experience like that can be very powerful. But yeah, if you do have, like, a bunch of, you know, a bunch of good relationships in your life, you're pretty happy. Like, it is kind of just, it's synthetic fun. Interesting. So you almost have had to stair, step your way up the embarrassment ladder, too. Oh, yeah. You're like, you know, now chicken costume is like, that's a Tuesday. Oh, yeah.

I could put one on right now. I was like, no problem. But it's, I mean, it's like anything, though, right? Like, I mean, it's, it's, you've, you climb that ladder with money, too, right? Like, it's like the first time you have a five-figure deal, you're sweating bullets. You know, now it's like you probably don't even get out of bed for a five-figure deal. So it's like anything in life is like that. You just, you get that progress.

progressive desensitization that happens over time. Yeah, that's probably actually bad in a lot of ways and why really rich people go crazy. It can be. You know, they can't find the new adrenaline rush. Yeah. Because, you know, you have a line actually that I like, which is like happiness comes from progress, therefore happiness requires struggle, which I think lends itself to this. Yes.

Because what if you can't find something to struggle on anymore? What does that quote mean to you? Well, it's paradoxical because the more successful you, you're, you're, you're not successful you become the harder it is to know what progress is or what progress is worth having. So, and this is why you see, so in my second book I talk about this, that there's, there's, I believe it's called the Easternland paradox in psychology, which is essentially that you find that the poor, the country or the poor, the neighborhood, the lower the suicide rate.

And the more affluent the country and the more affluent the neighborhood, the higher the suicide rate. And I think it comes from the fact that when you don't have anything in life, like when you're struggling on a day-to-day basis, meaning is very simple. It's like get to tomorrow, get the rent paid, get some food on the table. Like it's, there's no ambiguity of what you should be doing to be improving your life. If you're like kicking it in a Bel Air mansion, you know, with like some crazy nine figure exit or something and you're 32 and you have nothing to do all day. Like that is an existential crisis. Like nobody's going to shed a tear for you, but it's not obvious what progress is. It's not obvious what you should do next. In fact,

the fact that you can do potentially an infinite number of things actually makes it even harder to figure out what progress looks like or what you should. should be doing next. And so you often see, so it's funny, like I, there's a, I don't know if it's a national network or if it's just like a California thing, but there's, there's a network, it's called the post-exit founders group or network or whatever. And it's, and I've got some friends who are in it. And it's, I've talked to them before and they're like, yeah, dude, it's like when we do our events and everybody gets behind closed doors, it's like half the people there are like in an existential crisis because they just had this massive check hit their bank account.

they're not working anymore. And sure, you can like splurge on a boat and go to Greece or something, but like that gets old after a month or two. And then you're just sitting around being like, oh, shit. Yeah. What next? Especially if my entrepreneurship is a trauma response, which I think it is half the time. I'm like, what sane person would do this? That's not normal. And so if that's true, and so like half the reason you keep going is because you're kind of self-masochistic and you like the, you know, struggle and figuring out what to do next, if I only had the opportunity, of sipping mites all day and you got to look at yourself in the eye and nobody else, ooh, that could become problematic.

For sure. It's funny, like the one of the most depressed I've ever been is after my first book blew up. And it was because basically everything I'd been working for towards the previous 10 years all happened and got accomplished at the same time. And so then I just kind of sat around being like, well, I guess I'll play some more video games because I don't know what else to do. And it was like a very bleak six months. It was very strange, which is weird because everybody's patting you on the back and saying, oh my God, you must be living your dream. And you're like, yeah, this is my dream. But I'm the same

dude with the same problems and the same anxieties and the same bad habits. And except now I, now I have nothing to look forward to. I have like no definition of progress in my life. Buying a business or launching your own venture can feel impossible if you're stuck figuring out the website, logo, email, marketing, all it wants. But here's the good news. GoDaddy Arrow is here to help. So just a few prompts, it builds a professional website, a logo, an email, even social content, all tailored to your business. It's like having a whole launch team in your laptop. Instead of months of grinding, you can go from idea to launch ready business in minutes. No more waiting, no more guessing, just a real online presence that you can grow with day one.

Suddenly, the thing that was just a tiny idea in a notebook is online polished and ready to scale. So if you're ready to take your idea to life, head to godaddy.com backslash Cody Sanchez and try GoDaddy Arrow today. That book was so big, the subtle art of not giving a fuck. Obviously, we talked about it in the beginning of this in the intro, but it was so big. It is so big. I mean, one of the most sold nonfiction copies are books of all time. 20 something million copies at this point. Which is insane.

Also an incredible documentary on Netflix. I remember when that came out. Great thumbnail, too. Was that you? Weren't you at a floaty at a pool? Yeah, they put me in a pool. There's this like crazy, surreal opening sequence that involves me sitting in a pool drinking out of a pineapple.

Well, like people die and emergencies happen around me. It's like this very dramatic sequence. It was shot, it was like 45 degrees in New Zealand when they shot. So I was freezing my ass off the entire time. but, you know, I got to have my little Hollywood moment. It did not look like that. It looked lovely and happy. So cold. There was like a, there were a bunch of PAs with like mountains of towels on the side. So as soon as I got out of the pool, they just like draped all these towels over me.

So it's so cold. But you know, what's cool about that book that I think is really resurfacing for people. Boundaries are really big with the kids these days. You know, not giving a fuck, having confidence. That book, again, is like, I feel like even having another resurgence moment. I'm sure there are many people out there right now thinking about what other people think more than those other people are ever actually thinking about them.

Oh, like all of us. Right. Like you're talking about me. So the question is... It's called being human. The book's not that long, which I also love about it, but if you had to distill

for somebody who hasn't read it yet, what do you do when you give too many folks? So the paradoxical thing, and this is laid out in chapter one is is the whole idea of not giving a fuck it's a bit of a misnomer like this idea that things are just going to roll off your back and nothing's going to phase you like it that there's a word for that in psychology it's called a psychopath so it's we don't want that you do want to care about things obviously you do want people in your life that you you do care about

their opinion right like it should upset me if i don't know my my parents are mad at me um so the question is, how much should we care? So generally people who feel like they give a fuck about way too many things or what way too many people think, it's not an issue about the caring. It's the extent of how much they care. So the point I make in the book is that it's not about not giving a fuck what other people think. It's about finding something that is more important than what other people think. Because if you don't have anything more important going on in your life than what other people think about you, then what other people think about you is going to dictate everything else. And that's just like a shitty place to be. It's nothing good is going to

happen. But if you have, this comes back to the meaning and purpose thing, if you have something very meaningful, something you're giving yourself to, something you're willing to sacrifice for, something you care very, very deeply about, then suddenly it's okay if some people don't like you. It's okay if some people don't get it, if some people judge you or disapprove of you. So what would you say to somebody that's like, I just want to stop being such a, people pleaser. Find the hills that you're willing to die on. Like, find, like, ask yourself, what are you willing to be disliked for?

And for a people pleaser, that's going to be a very hard question to answer. They, like, they might not actually have anything that they can answer. And to, which at that point, your job becomes to find something. Find something you're willing to be disliked for. And then go do it. Because that, that's your thing. That's the piece of meaning and purpose that's going to be more important than other people's opinions. And as long as you're driving towards that, then everything else will kind of fall into place.

What is sort of the right way to respond when somebody else is like coming at you in a boundary way or when somebody else is trying to make you work outside of something that you feel comfortable with? How do you keep boundaries but not look like a dick? I think it's, I think tactically speaking, it's, it's always great to frame things like rules. So, you know, for instance, if I, if I was like, like, let's say your producer e-bell me and it was like, you know, come in at whatever a clock. And I was like, no, that's preposterous. I like, I refuse. Like, then it creates this ugly situation, right? Whereas if I'm just like, hey, man, I have this rule. I don't do interviews. after 3 p.m. Sorry, maybe we can find another time. Like when you, when you frame things as a rule, it's like, hey, this is just a rule I have in my life. I just don't do this thing. It's just to take

care of my own health and my own sanity or whatever. People respect it. And then if they don't, it actually, it makes it very easy to be like, oh, well, well, then fuck them. Like, they're not respecting my rule, so this is just not going to work out. So I always encourage people like, frame whatever boundaries you want to have, frame it as a rule. It's like, hey, I don't, you know, I don't talk about this subject with people who aren't part of my family. Nothing personal, you know? And then it's like, then things become very clear. It's so good because it's shifting the no to you to like, oh, no, it's not about you.

It's about this thing other here that already exists. It's like you get to use a shadow influence without even having one. Yeah. And then you get to deflect in a respectful way, whatever somebody else is. trying to push on you. That's so good. Yeah. And it's, what's interesting too is that it also clarifies for you the caliber of the relationship you have, right? Like, it's, if the person doesn't respect your rule, then by extension, they're not respecting you. So it makes it very clear of like, okay, this is, I have somebody in my life who is not respect, who doesn't respect me.

What am I going to do about that? Whereas if you're kind of in this people pleasing mode and you're like, well, I don't want to upset them. So I'm going to like, hint. and like maybe like be a little passive aggressive, drag my feet, pretend like I forgot, then you just end up in this like murky gray area where it's like nobody's really happy with how the friendship's going or the relationship's going. But like you're kind of going through the motions and like it just, yeah, it doesn't end well. Do you think that we are like over labeling ourselves such as like these days I was like

watching something online. It's like, I'm an avoidant. I'm a this. I'm a, you know, I'm with a passive aggressive person. He's definitely a narcissist. Like what is going on with all these labels? We're placing on ourselves. Are these real? Are they that black or white? Yeah. They are real. They're not necessarily black and white. And I have mixed feelings about it. Like, I think it's a sword that cuts both ways. So I do, and I do think there is a bit of an over labeling that that has been happening. So I'll make the bull case first for all this labeling. And I guess we could call this just kind of like therapy culture in general, you know? So it's like the all of the language that permeates TikTok and Instagram and YouTube these days and people

talking, you know, about being neurodivergent and avoidant and attachment types and dealing with narcissists and all this stuff. Like there's all this like kind of clinical therapy language that is entered into the mainstream. So on the one hand, it represents just an awareness of, like, a lot of these dynamics and issues, right? Which I don't think that's a bad thing. Like, if you go back a couple generations, like, people just buried shit for decades,

and it only come out after, you know, shove it down. Just keep shoving it down. Yeah, don't deal with that. And hope it doesn't come out after. nine or ten drinks. So I do think it's good that these things are being talked about. The problem is that there's a very fine line between labeling a problem and adopting a label

as an identity. So as soon as you adopt a label as an identity, like the way our minds work is whatever I've defined myself as part of my identity, I'm going to defend it and I'm going to become emotionally attached to it. So if I decide that, you know, let's say I'm ADHD, which I am diagnosed as ADHD, but if I decide to make that a core part of my identity, like it defines who I am and my relationships and how I like see the world and interact with the world, then I'm going to start imposing that on all of my experiences and my relationships.

And then you get this kind of self-fulfilling prophecy, which is that because I'm approaching every experience in my life is like, well, as an ADHD person, I can't really handle this. And as an ADHD person, you need to talk to me this way and not that way. You actually amplify how serious the condition is. Whereas if you just said like, okay, this is a thing I have and I'm just going to manage it and I'm not going to make it part of my identity, you can use that awareness to diminish how much it affects your life. So the problem I see is that a adopting these labels as an identity is being rewarded online. And so the more it's rewarded, the more people like cling to them, which the worst they feel for having them.

Great point. I've also been a diagnosis ADHD from an online test I did once. Very clinical. Yes, but the best part about the test was at the end, I didn't believe it when somebody sent it to me. but at the end, there was a literal link to talk to I guess it would have been a psychiatrist because they could prescribe and consider some sort of option, which I believe was some variant of Adderall that I hadn't heard of before. So like, you may need to get on a person with this one. And some of your treatment options,

so it was like kind of an ad. And I thought, for the love of all that's wholly, in a 15 question interview online, you're going to diagnose me as X thing and give me a pill, seems flawed. Yes. You know? There's a whole overdiagnosis issue. I mean, and that's just across the board, you know, anxiety disorders, depression, PTSD. Like there's probably all of those are being overdiagnosed to a certain extent.

I mean, the problem is just without getting down too much of a tangent. There's always been kind of the pharmaceutical incentive, right? to diagnose people. And I think for many, many decades, the population was underdiagnosed. So like that incentive was aligned with the public good. But I think probably in the last 10 years, 15 years, we're getting to a place where there's an overdiagnosis and now that incentive is an issue. And then on top of that, you have kind of the social incentives of, well, if I start making TikToks talking about my ADHD, then I'm going to get a following and all these other ADHD people are going to follow me. Or if I talk about my anxiety disorder or my panic attacks,

like all these other people are going to follow me. And then that becomes just a core part of who I am, which psychologically promotes, subtly it promotes a greater propensity for anxiety attacks and panic attacks, right? So like self-definition, I probably should have said this earlier, like self-definition has a huge impact on our mental well-being, right? Like, it, there's so much research about this on both good and bad labels. So, like, for instance, um, if you, like, if you set out and start a new challenge, you know, say it's a business challenge or it could be anything, it could be running a mile or whatever, simply deciding, like simply believing that you are.

capable of doing it, that you will be successful at it, like increases your odds of success substantially. It's the self-fulfilling prophecy aspect of life, right? Like if I tell myself that my new business venture is going to fail, it makes it more likely it's going to fail because it's going to prime my brain to start looking for all the ways it could screw up. And then when it does screw up, I'm going to be like, see, I always knew it was going to screw up. So it's like, this is why you often see like founders and entrepreneurs are delusional optimistic and overestimate themselves consistently because it's actually very useful in a certain context. You see this with the athletes. You generally see this with like a wide

range of highly successful people. The opposite of that is true as well. So if you, if you believe I can't do this because I'm an anxious person, I can't do this because it's going to be too stressful, I'm going to have panic attacks. You make it more likely that you are going to succumb to stress and panic attacks. That's not to say that it's the only thing causing your stress and people do legitimately have anxiety disorders and panic disorders and all sorts of things. But the language you use with yourself can move the needle in terms of the likelihood of it holding you back or not. And so the other concerning part of therapy culture, is that it is, I think it is subtly reinforcing people to place limitations on themselves.

To say, you know, instead of saying, I have ADHD and, well, actually, there's a bunch of contexts in situations that ADHD can actually be an asset. It's encouraging people to say, I have ADHD, so I'm just never going to be like a normal person. And there's all these things I can't do. And so, and there's a bunch of things I'm probably going to fail at. And then it, it becomes the self-fulfilling prophecy. If you're listening, like, how do you integrate this into your life? Like, what should you do instead of labeling yourself as negative things? How do you change and prime your brain so that you can label yourself a winner?

It's a great question. I also think there's potentially issues with labeling yourself a winner. So I'm of the Buddhist school of like, don't label yourself anything. You don't know who the fuck you are. because when you don't have a label, then your potential is infinite, right? Like you could potentially become anything or anybody you want.

So I just, I recommend people shy away from labels as much as possible. And if you do adopt one, like be very conscious of why you're adopting it and like what the, what the consequences of adopting that label are. I'll use kind of,

a superficial example, or it's not really superficial. It might sound superficial, but it was actually very profound for me. So I started, as we talked about earlier, I started blogging 2007. My first business was dating relationship coaching. And that actually did pretty well. And I was like happy and like everything was going great. And I decided to write a book to kind of promote my online coaching business. That book eventually became subtle art. Settle art went on and sold a bazillion copies. And sure enough, next thing I know, all these big book deals are showing up. All these publishers want to work with me. All, you know, all these like incredible opportunities are knocking on my door. I got to do a book with Will Smith. And it was super exciting. For the next five years,

I was working just as hard as I had always worked, but it was feeling like, I guess I would say like it started to feel like a grind. It started to feel like, obviously it wasn't a day job, but like the feeling that people get when you're just doing something for a paycheck, like it started to feel like that towards the end. And it really started to like grind me down. And I got pretty burnt out. And I took a sabbatical in 2022. And my big realization on the sabbatical was like, I thought I was an author. Like all of this shit, all the burnout and the stress and, and, like long, miserable hours.

The problem was I thought I was an author. I'm an entrepreneur. This is like I was creating a media and coaching business. I lost track of that because people showed up

and started offering me like more money than I'd ever seen in my life to play as an author. And so I told myself, I'm an author. I do author things now. And I started living

an author life. And it was like, I don't know, it was like walking around and clothes that are the wrong. size. Like, it's just very uncomfortable and eventually, like, starts to wear you down. And so in my sabbatical, I was like, I completely forgot. Like, I, the way I got here is because I'm an

entrepreneur, I should go back to being an entrepreneur and building online media and coaching businesses. And that's what I did. And I'm like, happy as a pig and shit. So I've written a book in five years. So it's a simple shift in definition. And I think, I guess my story, like the lesson from that is that it's very easy to unconsciously change how you see yourself based on the financial opportunities that show up. It's very tempting to do that. And I did that and it like I ended up paying the consequences. So, so yeah, I'm back to being an entrepreneur. I'm very happy. Comma, author. Yes. Sometimes author. Well, you know, you are really good at, which is I think one of the reasons why so many people follow you online, but why I like talking to you, you're really self-reflective.

Like, almost every time we've talked, you've been like, I'm thinking about this, I tried this, I didn't like it. Like, it didn't sit well with me. And so I thought about it and I changed it. And I think a lot of us in life, we just keep going. We're like, you know, don't pay attention, keep going. And that's why burnout comes. There's no self-reflection. There's no review. But like, you're quite good, I think, taking a step back and going, okay, let me think about this. And even a reframe, like I did there, you would have been very tempting for you to go like, oh, well, here's how you should label yourself. Yes. Like you accept somebody else's frame.

That's actually, it's really hard to not do, especially in an interview. Yeah. To go instead, you said, dumb question, this is what you should do instead, right? So for somebody listening, what is the way that you should self-reflect to even figure out, oh, I'm unhappy because I've labeled myself improperly. Yeah. Okay, when I sell my business, I want the best tax and investment advice. I want to help my kids, and I want to give back to the community. Ooh, then it's the vacation of a lifetime.

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Learn what's driving Canada's productivity decline and discover actionable solutions to reverse it. So a drum that I will bang on until my death, I, I always, I keep pushing this message into the kind of the productivity space and I feel like nobody wants to hear it. But I think it's extremely important. So for people who care right now are in a phase of their life that they care very deeply about success, productivity, achievement, all those things. You have to view your emotions as another system to be managed. Most people just, like you said, push the emotion that they compartmentalize they're like we're not going to think about that now i've got meetings to go to and it you can do that for a while you can do that for a year maybe a couple years but like at some point it's going to come back and it's really going to bite you in the ass and i i think that the thing that doesn't get talked about enough is that your emotions are another system to be managed to and as soon as you feel yourself getting off track emotionally of like not enjoying what you're doing, not being excited about the people you're working with,

not getting along with your team. These are all signals of like something's off. And sure, maybe it's not showing up on the balance sheet and it's not showing up in the P&L, but like, it matters because if you're miserable, like, that's fucking terrible ROI long term. Like you don't want to be stuck in a business. You don't want to build your own prison, essentially. So it's, it's, the first thing I would say for people who like, you know, really care about that stuff is, like, to just acknowledge that this matters, that it, like, it does affect everything. And the second thing, I think once you, once you realize that it is an important facet of, of everything that you're doing, it is another system to be managed, then you can start

looking at it and thinking about it like you look at and think about other systems in your business or your career of like, okay, where's the bottleneck? You know, where, where, where's like the, where's the, where's the place or the person that I'm putting tons of energy into and I feel like I'm getting very little out? Like, it's the exact same principles that you're applying in all these other areas of your life. You can, you can look at your emotional life in the exact same way. in terms of tactically, I, you know, I think I think journaling is like by far probably the easiest lift, like the highest leverage activity for people who haven't thought about this stuff a whole lot. Like just, you know, get yourself like an empty notebook and start asking yourself a lot of these questions. And really starting with like the basics. Like what do I feel about this? How am I feeling in this moment? How am I feeling today? How am I feeling about what I'm working on? How am I feeling about the people around me. And then once you've identified those feelings, like, ask, then ask yourself, why? Why do I feel this way? Why does, why does it feel so draining when I'm working on this

part of my business or on this part of my career? What is it about it? And then really, like, explore that, you know, give yourself the freedom to, to write pretty liberally until you, you find something. That's really good. So no screaming manifestations. in the mirror and journal just kind of briefly about the things that we feel and ask why. That seems reasonable for like, you know, internet people. It's funny too. Like, it's such a basic thing. I used to call this the Y game. And it's, you know, so you just take something, take something you're struggling with and say, like, how do you feel about that? Or like, why are you struggling with it? Take that reason. And then you take that reason. You say, okay, why is that reason a problem? And then you

get another reason. And you say, okay, why is that reason or problem? And it's just like layers of an onion. And you just keep going, going and going and going. And usually you'll get to a point where it gets circular. And, like, that circularity is usually like, okay, that's actually the real problem. That's the thing that you actually have to focus on, not this surface layer shit that, you know, you've been thinking about. That's so good. What, you know, on the same vein, you were talking originally about, hey, like, I think people get this wrong and they're not listening to this, but I'll scream it from the rooftops. What else do you think that young people today just have so wrong? Yeah. Well, we've definitely hit two of them, like the failure piece is that feels very

particular to Gen Z, I think. It's just the, I'm alarmed by the amount of risk aversion. I think the other thing that people, you know, we talked about boundaries a little bit earlier, I do feel like there's there's maybe an overcorrection that's happening there is again, it's great that people are becoming aware of boundaries and speaking up for themselves and being willing to say no. But I think, again, coming back, like there's so much shitty advice on social media that it's just like, if they don't respect you, then they can get the fuck out of your life. And it's like, well, no, actually, some people you don't want to do that with. Right? Like some people, some people you maybe want to stick it out and, and try to work with them or put some time into it. I do, there's some alarming. We did a, we did a podcast last year on kind of some alarming statistics on people, people cutting family members out of their lives. What's happening? It's, I forget the exact numbers because it's been a while, but it was an episode we did.

like probably like early 25 and it's yeah it's it's shocking it's way more people than you think it's something like 20 25% of gen z is like willingly chosen not to speak to at least one parent um a lot of siblings being cut off you know a lot of stuff and again i think it's it's like well-intentioned therapy culture type stuff of like you know well my mom is toxic or my brother never respects my boundaries or whatever. And I get where it's coming from, but I also think that there are, I feel like cutting family members out of your life is, is a move of last resort. Like, there's a lot of intermediary steps you can go. You can, you can, you can manage, you can manage exposure to people. You can manage, like, you know, set boundaries around which topics you, you'll talk with, how long you'll

spend with them, you know, what conversations you'll indulge which ones you will. won't. Yeah, there's just a lot of managing that you can do in between. That's so true. I mean, I always go back to the quote, it's like an African proverb about you can either pave the world in leather or you can wear leather shoes. And I think there is, I totally agree with you. Sometimes that person that's problematic is there to teach you something. And if you just avoid everybody that you don't like or everybody that is even toxic or everybody that is pushing boundaries, then that means you don't get better at holding them.

You don't get better at keeping things out of your perimeter that are toxic because you're so hard to push through. You know, if you don't allow these people in to teach you lessons in some way, you never get better. Yeah. Because you expect the whole world to be paved as opposed to wearing the shoes. And so I think, you know, it's cool because what you're building right now that I want to talk about is a pushback to a thing that scares the hell out of me,

which is I have like multiple girls. friends who have turned chat GPT and named it into their therapist. Okay. And the problem, as my friend Arthur Brooks said, better than I did, and I'm not going to say it as eloquent, is that he says, the problem with chat GPT is it is a malignant narcissist in that it is just trained to read back to you the things that it thinks that you want to hear. Yes.

And to agree with you by and large. And so, and it has no emotion. Yes. It is psychopathic and its tendencies. And so what concerns with some of my friends is these are like amazing people who will tell me that they'll have an argument with a man that they're dating and then go feed their side into chat GPT and chat GPT will confirm every single thing that they're doing. Of course.

And I love you friends, but some of you guys are fucking psychos too. Like, you know, we're all, we can get crazy relationships, me included. Of course. And I'm wrong all the time. And so if I only feed my side in and then chat GPT is always telling me I'm right, that seems bad. Yes. And I don't know, you're the expert in this. Like, what is happening?

Is that bad? Should people be using chat GPT as a therapist? What is your thought? And then I want to talk to you about your counterpoint to it. Deeply concerned as well. You know, I started noticing in my life, same thing. A bunch of friends, family members, started using chat GPT as a therapist. I went, this is maybe a year, year and a half ago.

I went and started experimenting with it, you know, kind of running some life problems through it, seeing how it responded. And I'll say this. It's like, it's very uneven. Like, you get, there's some things that it's much better at than, say, your average therapist. And then some things that's much worse at. So the thing you pointed out is what it's much worse at. It just validates.

It doesn't think critically. It doesn't challenge you. It doesn't. It just, it wants you to feel happy. It kisses your ass way too much. The thing that it's good at is it is, it is. In its data set is the entire wealth of knowledge, the entire field of psychology, essentially. Every research paper is in there.

Every finding is in there. Every branch of the topic is in there. I think there's over 3,000 hours worth of therapy transcripts in the foundational model. So if you get it away from, if you approach it with any problem that's not about validating your feelings, like if you actually ask it for some sort of tangible feedback or advice on a more specific problem, it will actually be extremely well informed on the research in that area and it will generally give you some good direction and good advice. The problem is that your

average layperson has no idea what the difference between those two things is. And so, yeah, that becomes very problematic, for sure. Yeah. And isn't, I mean, I was reading the other day that like 60% of LLMs are off of Reddit, which is I think where dreams go to die. So that like those people being my therapist is my personal nightmare, that would be horrific. Yes. But like I guess my point here is you're building something that's a counterpoint to this. Yes. Which is don't just go to, like if you actually want to change your life or fix your life, you don't

just want to be told you're right. And that's like my husband and I always say that to each other. We say, do you want to win or do you want to be right? Right. And often winning doesn't mean me personally when it might mean our relationship. Yes. You know, do I want our relationship to be good? Or do I want to say, you are wrong, I am right.

Tell me, tell it back to me. Yes. You know? And if that's what you want, then I guess go to chat, GPT. But if not, there's not a lot of other places to go to where somebody will kind of give you a little tough love. Yeah. And so you came up with something that I think's really clever. Yeah.

So I felt very strongly. So again, I felt this tension. And I'm like, it's definitely not meant for this purpose, but the potential is there. Like, it is, it is trained on so much wealth of psychological knowledge and data. And coincidentally, it was funny, I was actually at a poker game, I sat next to a guy and started talking to him. And his name was Raj. And he founded an AI business. Have you ever checked in a hotel and you get like a text message and it's like an AI concierge?

Yeah. said like, oh, I want towels or whatever. So he created that. He's probably doing okay. Yeah, yeah. He had like a very big exit and took a year off and had just, just finished his sabbatical, like when he went to that poker game. So I started talking to him. He's like, yeah, I'm just wrapping up a sabbatical.

I'm trying to figure out what's next. I was like, oh, cool. Like, what are you thinking about? And he said, well, I really want to do something in AI mental health. And I was like, no shit. Been thinking about this too. And turns out he had identified the exact same problem. He's like, there's so much potential here, but there's no LLM that has been optimized for it.

There's nothing that has been trained for it. There's nothing that's like been specifically created for this purpose. So he and I became co-founders. And he's, we've been working together since February. And as of this week, we were in full V1 launch of our app called Purpose. And the goal of it is to essentially be that. counterpoint the chat GPT instead of just trying to make you feel better all the time the goal is to actually make you better right tell you the things the hard things that you need to

hear you know point out your blind spots to you challenge you on your bullshit say like are you really sure about that or like maybe like your shit stinks too um and it's been great like it's it's because here's the funny thing that we've actually noticed with a lot of our early users as well is that like people are way more honest with an AI than they are with a therapist piss. Like if you, I don't know about you, but like my experience in therapy, like, it often takes like four or five, six sessions just to get to the point where I'm like, okay, I'll actually say this thing to her, right? And you want them to like you more than your partner? That's like the natural inclination. You're like, he's the, you know, the thing is. It's all about your

perspective. Right. A hundred percent. But it's, um, you know, when it's an AI, it's just like, well, fuck it, whatever. I'll just, this is what I'm thinking. This is, this is what I, yeah, I'm kind of screwed up. But like, you. But like, you know, you. here it is. You know, like it never judges you. It's like you never have to worry about it. You know,

it's going to like hold something against you or it's like secretly thinking something about you. So generally speaking, we see people are much more forthcoming with it. And, and you actually get to that clarity extremely quickly. Like sometimes in a matter of minutes. It's like pretty crazy.

Is there like a Mark Manson button? Or Mark Manson? Is there a, is there a button where we can get your voice to talk back to? us? Not yet. Maybe. Maybe. That might be coming. Or is it really nice still? It is nice. Does it cuss? No. I have a lot of user feedback. I feel like, I feel like this is a miss. I wanted to be able to talk shit to me from the author of The Subtle Art of Giving a Fuck, back. We actually talked about this. And one of the things, you know, one of the things I told my co-founder is I was like, look, like, I'm under no.

illusions that I'm the right person for everybody, right? So it's, I actually think if we put my personality on it, we would be limiting it. It would help fewer people. So it is, it is not limited to me, but you know, maybe we will get a mark and a button. Just a little button. Yeah, just one. Yeah, exactly. Pull your head out. Also, talk about viral feedback loops. Yes. You know, can you imagine those screenshots. Yeah, it'd be fun. Yeah. Come on. All right, let me on the cap table. I've got feedback. But I really like the idea and I really commend my husband's the smarty on AI. It's not me.

But, you know, I go, just this weekend. I was with, yeah, last weekend, whatever, whatever A. A.C.L. was. And I was with all these guys who, like, the guy who started Apptronic, you know, the robot company and, well, I won't say the, anyway, like, just a bunch of really big names in robotics and AI. And I had the funniest conversation. It wasn't from the CEO of that.

But, um, and the conversation kind of went like this. I was like, don't you think we should worry, like a little bit about what we're building with AI? Because seems like happiness, gone down. Sex, gone down. Marriage, gone down. Like social media has like, like, by and large, us gluing our faces to the phones, by and large, incredible for productivity and like GDP growth. Yeah. Not so great for just being happy, like as humans, it seems like, or even procreating. Like, the dad is kind of hard to refute, I think, on that. So if that's true, I'm like, maybe, you know, if they, like, neurochip adds into our brains, it would be not great. And so anyway, like, that seems, like, reasonable to me. And as I was talking to this guy, who's a really nice guy that I like,

he was like, well, I'm a tech optimist. And I thought, yeah, like, I'm an optimist, too, but you could be cautiously optimistic, which also seems rational. And he's like, no, we'll just, like, figure it out. I go, well, we haven't exactly figured it out. So shouldn't we, like, put, like, how have these conversations and say, what are we building it? Is this a really a good idea? And, and, you know, how could we try to take all the knowledge we have of human psychology for millennia and realize that if this is an extension of human psychology, it's probably good to put some guardrails on it, if at all humanly possible? For sure. So, like, I commend that you're doing it. Because his response was hysterical. It was like, maximum mansplain. He goes, listen,

come on Monday, I'll explain AI to you. I was like, get the fuck out. I was like, that's what I I was like, I was like, I want to have my big dick energy. I'm like, I'm going to open my legs wider than you, you know? But I know, isn't that funny? I mean, and I'm not pretending I know very much about AI, but we've invested in a slew of companies and even the best founders are concerned. Oh, we spend like a ridiculous amount of time. The two big things we spend most of our development time on is privacy and guardrails.

Because it is such early days and we are still learning so much about what is an appropriate. use of this technology and what's not. And, and yeah, it's hard. It's, it, it, it's, it's, it's, it's constantly testing it like, it's, it's very, very high on our priority list. The one thing I will say to what you just said is, and this actually like relieved me. It's going to sound a little bit funny when I explain. When I went in, when I started this company, you know, I was very, like basically, we, you know, Raj is the engineer, the builder, you know, it built this. team built all the development team and everything. And then I was kind of the product guy. So I had a rough idea of like how this thing should talk, what it should sound like, what good,

tough love advice is and what is just kissing your ass. And so I spent a lot of time working with the LLM directly like on the Evel system, the training data, all the system prompts, like trying to squeeze out of it, like what should come out of it. And I, I will say after working very, very closely directly with an LLM for over a year now, I've actually, my estimation of what they're capable of has dropped considerably. Like they are, they're like brilliant idiots. Like they will, they will do multivariate calculus while doing a backflip and like spinning two plates on their fingers.

But then, you know, like their shoes will be on wrong. Like it's, there's like so many situations. like that, that, you know, there been so many times where I've just been trying to get a, get it to do, like, such a basic thing. And it'll take an entire afternoon. And I'm like, okay, there's no way this thing's taking over the world. Like, it just, like, the fact that it can't even give me this, like, one text response when I specifically ask for it, you know, it's like, okay, we're probably going to be okay for a while. So I do think there's a lot of, there's a little bit of moral panic going on around it. I don't think they're quite as capable.

as most of it. I mean, I don't know how much you guys have been using AI in your business, but it's, it's like, a year ago, I was like so on the train of like, everybody on my team, you've got to get good at AI right now. This is going to be part of every workflow. And six months later, we're like, oh, half of it is just trash. I do think garbage and garbage out. Yeah. And it's actually very, very hard to, you have to be extremely skilled to get it to do what you want extremely well. And oftentimes the amount of effort it takes to get it to do something you want extremely well, you might as well just do it yourself. Yeah, I'm still there sometimes too. But I do have, we hired a whole AI specialist team. So it's actually so fun to work with them because they're just, they're also smarter than me at prompting. And with AI too, you have to know, I mean, to go to your part about beautiful idiots or brilliant idiots, you know, there's like, there is the plate spinner that is the best plate spinner of all time. Yes. But that you have to match with the backflipper sometimes.

And you're like, oh, okay, the two of you together do some magic, but independently, Jesus. Yeah. You know, there's like one other place I want to go with you today. Totally unrelated to AI, hard pivot. But you did start in dating. And I've always, like, respected the conversations we've had about you and your wife. Yeah.

And how you choose partners. So I want to read you a couple quotes and get your feedback. You said, choosing a romantic partner isn't just about romance. you're also choosing a confidant, counselor, career advisor, therapist, investor, teacher, travel buddy, roommate, and business partner. Choose wisely. And the question I think is, does that still hold true for you? That was from quite a few years ago. And how exactly does one find this type of partner? It's funny because when I posted that, I got a bunch of blowback of people like, oh, you shouldn't hold people to such high expectations. And I think like what gets missed is that it's not that you should go looking for all those things. it's it's when you choose to marry somebody that's what you're getting whether you want it or not that person your your spouse becomes that all of those things for you so you you have to vet them beyond just how is the romance or how spicy is the the sex like it you have to think through

like a lot of different personality traits um and i i think it's absolutely true i i personally think Marrying well is like the single highest leveraged decision of your entire life. And also not marrying well is also a very high leverage decision. Like it is just the force multiplier on all of your outcomes across life. And it's not just your career outcomes. It's your happiness outcomes. It's your health outcomes. It's all sorts of things.

Your social life. A good spouse makes everything better. And a bad spouse will make everything worse. It's so true. I totally agree, and I get shit about it on the internet, too. And you know what else is scary? I'm always scared to give advice because I'm like, I don't know, check back in 40 years. See what we're doing?

Like, I should, this is like, I'm kind of new with this. It's only been 10 years, you know? Like, let's chill, but we're doing good right now. Yeah. What advice do you have for a young person that is looking for what you have, which is somebody that is all of those things? I think the biggest thing that look for is character. it's

it's again, yes, you want the romance, you want the sparks to fly, you want to have be swept off your feet and all, like we all want that. It's great.

Don't get me wrong. But you have to look a level deeper. You have to look at their character, their integrity. How good of a decision maker are they, are they dependable? Are they trustworthy? Do they share your values?

how's their relationship with their family? Like all these things matter. And obviously nobody's perfect. Like nobody's going to check every single box. But you, ideally you want to find somebody who checks most of them. And the ones they don't check, like you can work with it.

You know? Do you have like a couple questions you ask? Like if you, I know we're both like a little, we're a little baked now. Yeah. But, you know, but basically, Shut up, Mark.

But like, if you were given young you advice, the team actually asked me this the other day. I was like, oh, I was having an existential crisis trying to answer it. But like, what, if I only had three or five questions to sort of start sussing out, is this potentially my person or not? What are those? Well, I will tell you, my favorite first date question that I recommend everybody ask is ask the person you're on a date with. what did you learn from your last relationship? And the red flag is if the person starts going off about how horrible their ex was and how shitty they were and oh my God, I can't believe I dated them for so long.

Like that person run far away. Get as far away as you can. What you're looking for is somebody who says, you know, it was a complicated relationship. It was good for a while. Then things went bad. Here's why they went bad. here's here was my part in it this was their part in it somebody who has perspective and an understanding of like what went wrong and and who also has clearly like done some work since

then to make sure that it doesn't go wrong again i also love the question too because it if you ask it and the person kind of freaks out and gets really uncomfortable that's also a signal right it's a signal that this is not a person who is comfortable opening up relatively quickly who like doesn't want to go there. You know what's crazy is that's the same thing for interviewing too. I always say if like the person you were going to hire if you ask them like tell me what happened in your last job. Like why did you leave? Why did you choose to move on? If they start going negative, the company was terrible, the boss was awful, everything was ever. I have never once hired one of those people and had it work out. Not once. Every single time I wished I didn't

hire them. Because I think the way that you treat the last person, the highest indication will be that you will be treated the same, right? Yeah, absolutely. Oh, that's such a good one. Okay, last one for you. You've also tweeted, the person you marry is the person you fight with, the house you buy is the house you repair.

The dream job you take is the job you stress over. Everything comes with an inherent sacrifice. Whatever makes us feel good will also inevitably make us feel bad. What do you mean? You can't escape the bullshit. You can't escape it. It's no matter where you. you go, there's going to be some bullshit. So you just need to make sure that it's the bullshit

you like having. It's the problems you are grateful that you have in your life. Again, I think people they think about the benefits and the successes that they want. That's actually a very easy and uninteresting question. Everybody generally wants, like everybody wants money. Everybody wants a great partner. Everybody wants to be liked and popular. And, you know, know, all these things. The question is, is like, what pain do you want? Like, what are you willing to give up? What struggles are you actually kind of okay having?

Like, what challenges do you seem to do better with than most people? Like, those are, that's actually where you get into who somebody is. And, like, what makes you unique as an individual and what is ultimately going to serve you best as you move through life? That's so good. I always say with goals, like, don't tell me what you want. Tell me what you're willing to sacrifice to get them. But I've never actually asked. I've like proselytized on the internet about that.

But I don't ever think I've actually asked somebody. Like, have you asked your wife or your friends or people you meet with those questions? Like, what are you willing to give up? Yeah. Like, what is the pain that you want? Like, what would be the way that you would even ask those questions to something? Because it's kind of hot. I want to, like, I need to go around.

I need to go around. You know, you can take that question multiple ways. But like, I like it. Yeah. It's when I give talks, I always say, I say like everybody is secretly a masochist about something. The question is just like, what do you want to spank you and call you daddy? By the way, this goes over great at like corporate conferences. Do you say that on stage?

You can imagine I get invited back all the time. Google's like, pull them. You and I probably have the most polar opposite corporate speaking. experience. No, I tell all their employees to leave. And then you tell them who wants to spank them. You know what? I'll start bringing you along. Let's do a road show. Yeah, we'd just

be the anti-corporate speaker. Yeah, exactly. Yeah, it's I like to frame it in those terms. It is a, it's a hard question. Like, nobody I think nobody asked themselves, nobody's asked it very often. It's like, what do you, what do you

actually kind of secretly like? Like, what problem do you secretly like having. It's like a very interesting question that most of us don't think about. And, but yeah, I think I think the answer is extremely important. What do you like? The problem I secretly enjoy having, I mean, I'm a workaholic. Like, I like the grind. I like climbing the ladder. Like, it's just fun. It's like, I told my dad one. You know, so when I came back and I started scaling content and doing video and stuff online and launching a podcast and everything, my dad kind of pulled me aside and he's like, you know, why are you doing this? He's like, financially, you're pretty set. And, uh, and I told him I was like, dad, it's like I found the best video game and there's always another level. Like you can, you never beat it. And, uh, and he, he got it. He was like, okay, that's cool. That's a good reason. to do it. That's such a good place to end. Mark, this was incredible. Thank you so much for being on the

podcast. Thanks for having me.