The Startup Ideas Podcast - How To Create Your Own Luck With Julien Smith

Episode Date: June 30, 2022

Are you or your business stuck between a rock and a hard place? In today’s episode, we explore why suffering actually makes you stronger, divulge the secret to getting your business started, and share how you can make your own luck. Hosts Sahil Bloom and Greg Isenberg are joined by guest Julien Smith, a NYT bestselling author turned founder (Practice.do | Breather), who raised more than $250M for his first venture. Julien shares his personal underdog story, how entrepreneurship is never as perfect as it seems, and offers insights into what allowed him to find happiness in both his life and career.►► Want more community? Learn more here: http://trwih.comSPECIAL THANKS TO OUR SPONSORS►► This episode is brought to you by Lemon.io. Did you know that one of the top reasons startups fail is bad hiring decisions? People can be unpredictable. And developers can be unpredicted, as well. Let Lemon.io take care of hiring your software engineers. They have a hand-picked roster of engineers from Europe, and we recommend them to companies we work with.Sign up at https://lemon.io/room for 15% off for the first 4 weeks.►► This episode is brought to you by Fundrise. Fundrise is on a mission to use technology to build a better financial system for the individual. With over $2.4B AUM and 250k active investors, it’s the largest direct-to-investor real estate investor platform in America.Their platform is so easy to use and they make it so easy to diversify your portfolio. For a limited time if you sign-up, you can get $10 bonus. Just go to www.fundrise.com/roomTHIS EPISODEJulien Smith: https://twitter.com/julienSahil Bloom: https://twitter.com/SahilBloomGreg Isenberg: https://twitter.com/gregisenbergProduction & Marketing Team: https://penname.co/FIND US ON SOCIALTwitter: https://twitter.com/_trwihInstagram: https://www.instagram.com/_trwihTikTok: https://www.tiktok.com/@_trwihWeb: https://trwih.comSpotify: https://open.spotify.com/show/6aB0v6amo3a8hgTCjlTlvhApple: https://podcasts.apple.com/us/podcast/where-it-happens/id1593424985

No matter what happens to you, you stay in the arena. You're not always going to win, but you're always going to try. And so long as you get smarter, you will have good things that happen to you, even as other good things pass you by. And it's kind of like a mindset that you have to have if you're going to be, not even just in tech, just in entrepreneurship, probably. All right, Greg, to start this episode, I'm going to need a story on this hat. If you're not watching on YouTube, Greg has a very interesting hat selection for today's show.

On my 30th birthday, I went to Joshua Tree with some of my closest friends. And they made me a hat called What Would Greg Do, WWGD? And I just remember wearing this hat, blowing out the candles, 30 candles on my birthday, and just feeling like I've made it. Because if you have a hat that says WW. Oh, Julian's putting on a hat.

Is that a WWJD? Green hat. What did Julian do? Also a green hat. I don't know if I have a green hat line around that is. That's another hat that you can wear that you sort of made it. If you're wearing a spreadsheet hat. But Greg's hat, your hat has an avatar of you on there.

And that avatar always cracks me up. because it's your old Twitter picture. And I remember, like, because of your avatar, most people that were following you thought you were like a 55-year-old man. And when we launched this podcast in, what was that, like November of 2021, and we filmed our first episode and put it up, like half of the replies we got to the first episode were literally commenting on the fact that they thought Greg was 55 and it turned out he was actually a younger guy.

People thought I was like a, you know, mid-60s Wall Street Journal, journalist. So I really confuse people. You kind of give off those vibes. Well, look, we're Julian so, so excited to have you on today, man. This has been a long time coming. Julian Smith, we're going to get into a lot of who you are, so I don't want to, like, fail to do you justice by trying to define you with, like,

a one-sentence blurb at the beginning. So I'm going to actually just refrain from doing that. but you are a personal friend to both of us, you know, someone we both admire a lot as an entrepreneur and as a thinker more broadly. And so super excited to have this discussion with you and get to share it with everyone so that we can spend a little time getting inside your head and just having a having a little bit of a jam session here. Yeah, thanks for having me. Did you know that one of the top reasons startups fail is bad hiring decisions? People can be unpredictable and developers can be unpredictable as well. Let lemon.io take care of hiring your software engineers. Why lemon.io?

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So I was trying to think about like where to start on this conversation. Greg and I were chatting yesterday as we had done our research and we're thinking about like, what's the right way to frame this up with Julian? Because you are, as I said, many, many things. And I think probably a lot of people know you for your entrepreneurial pursuits, arguably more interesting than your entrepreneurial pursuits is your path and kind of how you formed your map of reality to get there. And Greg was the one that alerted me to this, that you, and kind of sent me your website and some of your old blogs and the books you had written. So can you just walk us through a little bit to kind of set the stage on like, who is Julian Smith? Like, you know, you were born, now you're

here, what happened in between? Yeah, I had to figure, so regarding the map of reality, I it's important to state that I was brought up super working class. My father was a coach, like an exact coach, but really before that he was a teacher in a one room school

in Saskatchewan, Canada. My mother was a secretary. And so I think a lot of people in tech they were like quite well connected maybe at the very beginning or they went to some cool school or some other thing like that. foundation foundationally in my in my life i i'm an underdog which is which is someone that believes

that no one is going to pay attention that no that i don't like i'm never going to get a break that no one's ever going to offer me a job which is still really true actually even now and that i'm going to have to really really work hard for all of the things that i have to do now that said at the same time i'm also a person who has got to and super lucky very early on in my life. Greg and I share like a few things. I don't know how much. Like I've been some there's a number of episodes of this I've listened to. I don't know if Greg has ever shared like for example things about affiliate marketing, which I also share early on in my history, which is like these weird breaks where like you know, previous to our generation,

you couldn't have like some 20 year old kid that's like yeah, I made a couple million dollars online kind of doing nothing. And then I went on and did some other thing. But I was one of those people. And so just for people that don't understand that, what is that? What is affiliate marketing? Like, it's new to me, relatively new as a concept. So, like, what were you and Greg doing in those early days? You know, the little Montreal mafia of like a 16-year-old that were somehow making bank on the internet while I was, like, dicking around doing God knows what at age 16. I'm just fascinated.

You caught up, so it's okay. It's, it's, what Greg and I mean, he'd speak to his experience. We didn't know each other then. But in my background, where it came from is I was one of the first podcasters in the world. I don't know. It's really a thing you should be that proud of. It's interesting. But because of that, there was no way to monetize podcasts back then except for coupon codes.

And as a result of coupon codes, because you could say a coupon code on a podcast, right, the result of that, which I've heard you do, is an ability to attribute a sale to a podcast. And so I got really, really, really good at hustling coupon codes back in 2004 when I was 25 or 26 or 27 or something. And that is how I switched from having like a real shitty job. Going back to the history, like no college degree dropped out like five, six times working a customer service job to recording a podcast and all of a sudden I had an online income out of nowhere. And so back to the map of reality. is like, it's kind of like, I'm going to have to keep working hard. But if I keep working hard, I don't know where the breaks are going to come from, but I'm going to get some.

Right. It's kind of like how I think about what I do. Yeah, it's like the, it's like this whole idea of like creating luck, which I've written about and talked about a lot. It's, you know, one form of that is, and I think Noval has written about this in the past, but you just like move around enough and create enough motion in your ecosystem that you're just bound to get lucky because you're like you're literally if you're like an atom entering an ecosystem and you're just like shooting around banging into things like shooting or you know crashing into stuff

somehow some way there's going to be some lucky thing that happens to you as a result of all that motion you're creating it's i always love that as like a generalized mental model around these things especially for young people because i think it's like it's something that anyone can do um you know you don't have to be an expert at something yet you can just create a lot of emotion and figure out expertise as you go. That's true. The other side of that is it means that you're going to miss some. You're going to go out and it's like one of the things is like you used to take really take those things really personally.

It's just be like, oh, I came up with this thing. And then like, but a good early example is being very early in podcasting so early that I was obviously too early. Right. And so it's like we used to talk about, oh, it's going to kill radio. and it was my first job. I got hired. My podcast ended up on serious satellite radio in 2000, I feel like six or something like that. Oh, my gosh.

That's a big break. But it's such a big break in such a small ecosystem back then. It turns out that doesn't fucking matter. And being early is the same thing as being wrong. Right. Yeah, exactly. And so you're going to get some lucky breaks, presuming the hamster wheel keeps going and you keep staying on it.

But at the same time, you're going to miss some. and when you miss some, you have to just like take the hell and move on. Yeah, the question is how painful those misses are. And like if they damage you or if they compound in the long run, I've always thought, you know, there's like something I've thought about recently is like, you know, if you're using like a fighter example, if you're kind of a fighter and you take like a glancing blow, you know, someone like almost knocks you out, but it like kind of slips off. There's like two types of people.

There's the person that is like, oh, few, I'm good. Don't worry about it. Like he missed me. And then there's the person that's like, what did I do that exposed me to that? Like, what did I learn from that situation right there? Why did I take that glancing ball? And how do I avoid that in the future? And the second person is obviously able to like compound on the positive experience from taking the glancing blow where the first person is just as likely to take a knockout blow on the next punch because they didn't learn from that first one.

So it's an interesting thing. I think like what you're talking about is you as you learn as you create that motion. what are you doing to learn from those Ls and actually build upon them rather than just have them be, you know, some L on your scorecard? It's difficult because when you do this, when you take them, you also all of a sudden realize your own vulnerability. Like, like I remember the first time, I went out surfing way too far, way too early. And as a result of doing that, like I almost round at least once, right? And so that's when you're out there. And I remember this happens.

It's like a critical moment in my life. I'll never forget it. saved. Well, I mean, there were a lot of surfers around me. So I probably wasn't going to drown, but holy shit, did I ever feel like I was going to drown? And so what it does is it creates this kind of vague PTSD or maybe acute PTSD from something that traumatized you. It could be a business failure or it could be very visceral like what I'm describing right now. And the hardest part as you get older and you have more like experience under your belt doing these things is to retain that kind of fearlessness, right? And that's why Peter Thiel, who by the way, like all of these

people who we used to like just quote without any repercussions, now we quote them and we're afraid to do so because they've gone off the rails in some cases. I don't agree with everything he says. But he would be like, no, no, you don't want failure. People in startups talk about failure and really embrace it to a degree that's true. But at the same time, the fearlessness isn't so incredibly valuable. Like Breeder, I would never have started such an ambitious company as a second time company because it takes so much balls to be able to do that, to do this crazy, radical off-the-wall thing that nobody had really even conceived of existing. As a third startup, that's really hard. Right. I was going to ask you guys this as like both of you, you know,

are builders and you've tried, tested, failed, succeeded with a variety of things over your careers and lives. Do you think that there is a common thread of like having that almost like irrational optimism or like degree of arrogance, like the willingness to go out way deeper than you should have surfing and the version of that that is in work? You know, you mentioned it with breather. Like Greg, have you experienced that as a builder? Consumer Social is like the ultimate example of that I think anyone that goes into consumer social to build has to have that type of like boundless irrational optimism to some extent or like masochism to be honest. I want to clarify the you know, sort of where we came from and how that impacts who we are.

And I think this is relevant to anyone not from New York and not from San Francisco. You know, a lot of our friends that we grew up with and clarify, if I'm wrong, Julian, but they're not doing big things at all. A lot of them don't even work. And it's not like they're not working because they're on the beach. They're just like barely working, part-time jobs, you know, consulting one day a week, chilling out. And this is like, I know, I'm going to offend a lot of people. I'm breaking the code.

You're breaking the code. You're breaking the code. You know. You are a Montreal code of silence. That exists and where we came from is high. And there's a cost associated with that as well. And because of that, I think people like, Julian and I kind of like, you know, our role models were people in books and people that we

watched on TV. Like there's a reason why Julian was reading like a book a week or something like that and ended up writing, you know, New York Times bestselling book. And there was reasons why, you know, I was, you know, traveling a lot and sort of spent a lot of time there. The point is the other thing is the cost of like us failing was, you know, for. felt, I don't know, it felt smaller. You know, when I could have gotten an apartment for $500 a month instead of $4,000 a month

in San Francisco, or when all my friends, you know, when I started a company, thought I was crazy. I don't know. I felt like being from a place where there's less success stories, you just feel a bit more fearless because... What do you think, Julian? sensible. It's like Adam Greg,

we have a lawyer that we collectively have shared in the past. I would just say his first name. Adam is the name of the lawyer. And he, I brought breather to him. By the way, like literally nobody thought that this was a good idea. Like, and I mean it, like literally no one. Maybe Greg, like, I was like, here, you should like, what should do this? And maybe he was the closest thing to maybe accepting that this could be a company, right?

And so I bring the lawyer to breakfast in Westmount. Some of you care about this. Most of you will not. And the lawyer brings a sort of real estate, like management firm dude. And both of them are like, you should not. Like you have a successful thing going. Like you've got a New York Times bestselling book. Like you're doing speaking gigs.

Like, don't do this was the general attitude of like, don't fuck up your life, right? And so it's, it, we, and that's one of the hardworking ones. In general, it's like, you know, I always think about this, this Paul Graham thing about like a city is telling you something. The city itself is not telling you something, but the ethos of that city is saying things to you. And where we come from, the city is just like, yeah, hang out. Like, everything's cool. You're going to be all right. You don't need to work that hard. And, and so, It makes it, it makes the cost of failure low because nobody cares anyway, versus let's say in New York where everyone is richer and cooler than you or whatever the hell else.

But the other downside of it is that you have no support. And when you have no support, you become incredibly like galvanized against other people saying things that like they don't agree. And like literally nobody like, you know, I remember being in the first 10,000 users in 20,000. Twitter in 2006. Like, as you know, you just went through your, my history of things and, and you discover that I've been around for a long time. And so I have. And just, I would, I would come back to like, people around me and be like, hey, here's

this thing. Meanwhile, it was on Oprah or whatever, whatever was happening with Twitter back now. And everyone, everyone around me was like, this is dumb. You are dumb. If I go back to high school, it's just like there was a lot of that back then as well. And this is when it really, I started becoming galvanized against ultimately rejection. it's just like I had no choice

but to kind of like rise out of the ashes of this fucking like way of being was just like okay wait nobody agrees with me either I'm dumb but I don't think I am I feel like I got something maybe these people just don't understand me

and you just get stronger and stronger and stronger as you do this right and so like that's like the thing about growing up in a different type of ecosystem that values different things it seems like there's also a common thread in what you guys are saying of just like realizing that the worst case isn't that bad um i've always like gregg i've talked to you about this recently like i've had these deep-seated fears of certain things um one of my deep-seated fears is like people calling me an idiot like people

people realizing that i'm an idiot you know like an imposter syndrome thing of like oh my god they're gonna figure out that i'm an idiot and that I don't belong here. And like for the longest time, I've just been like, oh, my God, really careful about everything that I say everywhere because I was just worried about that. And then I kind of got dragged on the internet for something that I said, which, you know, was probably like not really well thought through and probably naive, fair. But like a lot of people called me an idiot all at once. And I texted Greg and I was like, you know, there's sort of this funny feeling of like,

once it's happened, you realize like, oh, I'm still here. Like I got punched in the face a whole. whole lot there over and over and over again by like my biggest fear like something I really deeply, viscerally did not want to ever happen to me. And I'm still standing here. And we're still having this conversation. I still have friends. Like people still care about me. It's okay. And I think that there's like a common thread there as well of just like that realization with entrepreneurs that the worst case, you know, you fail. Like the thing you thought was going to work is not. And you kind of pick your, pick yourself up. And like American law has great bankruptcy laws.

and you can make your way and reset the clock and figure out how to go do your next thing and take another shot at it. And there's plenty of case studies of people who've had that happen and then had their amazing success on turn three, four, or five. That's very true. And at the same time, you are always thinking, because you're watching the media, not the media with capital M, but you're watching various forms of like info that is being pushed back at you.

And the media is driving this. narrative of you're young, probably your parents are rich, probably you have a reality show, probably you're thin and successful in like all of these other things, and you're like, you look at yourself in the mirror, whoever you are, it doesn't really matter. And you're like, but I'm ugly and stupid. And so, and it doesn't matter how many successes you have on your belt. there's still a part of you that still try to fight that. I was listening to your Josh Wolf thing the other day.

And it was incredible the transparency of someone who's obviously done really well and who's well respected, but who at the same time it allowed him to be even more clear about what his weaknesses are. And I really respect that because it takes even, you know, it takes, a lot. It especially takes a lot as an entrepreneur. As an entrepreneur, it is especially like this, the culture of we're doing well, I'm doing well, is so consistent and pervasive. But as a second time entrepreneur, I will tell you something that I really learned. In my first company, venture back company, I really was like, we're doing well. Everything's going great. I really,

I did this. I trumpeted this attitude of positivity. Now what I do is, is I say, here's the things that are going well, here's the things we need to work on. And I think that that understanding that there's still something to work on, first of all, it gives an impression to me that of me that people are like, oh, he actually knows what he's doing. He's not just like relentlessly trumpeting optimism all the time. And then the second one is I get to them like normalize the fuck ups, which is like, yeah, we don't know this yet. And we don't understand. this yet and we don't understand yet this yet versus saying one thing and believing another and having that that difference between the outside world and the inside world cause you to

like fucking have anxiety attacks or whatever it is. You talked about a lot of this in one of your blog posts like when I was going through and reading some of your old blogs to get a better understanding of you prior to the episode. You know one of your like best blog posts is is called the complete guide to not giving a fuck. Okay. It's so good. Like, highly recommend people go and read it because it's amazing. And I just super, super thoughtful.

Can you talk a little bit about that piece? I mean, like, people know this concept because of a book that came out, although I'm checking the date stamps on it. Your piece came out April 2011. That book came out in 2016. So I'm going to ask you about that as well. And it's ironic that I was an author of book them, like at that time when that piece was written at the same time, right? I hadn't started a company. So I don't really talk about this

because it's one of the things that I sort of move past, but I'll talk about it here with all y'all because we know each other and so on and it's like whatever. But I definitely, I don't want to be one of those people that is like, but look at this thing before it. Because you know what happens in tech as all these people are like, but I invented Twitter before, five years before. And then you're like, no, you fucking did it. You fucking invented a stupid thing. And so here is the story. The story is in 2011, I guess I published this blog post, which you can look up. And the reason it was so successful is because from an SEO standpoint, my website was excellent.

And my affiliate marketing business was based in SEO. And so when I wrote this piece, all of a sudden, I ranked number one for years for how to not give a fuck for years. And so 10,000 visits today or some shit would go to my website for this idea of not giving a fuck, right? If you think about it as an incredible, like a thing that lots of people want. And so I did write a book then, which actually is, which was extremely well read at that time.

And even today that it's still like I get message about called flinch, which is this about this idea of making sure not to to shirk away from things that you're afraid of. And then I wrote another book, which is Portfolio Penguin, which is called The Impact Equation. After those three books, I went and I started Breeder. But alongside that happening, probably what happened is that, and this is the part that I kind of try not to talk about because I don't want it to seem like sour grapes. Well, I asked about it. Yeah, I understand.

Yeah. Typically, I would not bring this off. is this thing continued to rank number one for complete night guide to not giving a buck for literally forever. And then along the line, some kind of thing happened. And then it became a book and then I started seeing in bookstores. And I'm not saying because I haven't read this book. And by the way, I have no intention of reading it ever. But lots of people have read it.

I went to Italy one time and I saw somebody reading it on that next to the pool. And I was like, man, this is really weird. And I and but I, this. is one of those things about staying in the arena. No matter what happens to you, you stay in the arena. You're not always going to win, but you're always going to try. And so long as you get smarter, you will have good things that happen to you, even as other good things pass you by. And it's kind of like a mindset that you have to have if you're going to be in, not even just in tech, just in entrepreneurship, probably. So I appreciate you sharing that.

because I know that it's not something you've you've shared publicly before. I have read the book. I thought your blog post is better just for what it's worth. Don't tell the author of the book. But no, I mean, look, it is, it's another example of like one of those, you know, one of those moments in your career that, you know, at the time feels damaging and you wrestle with. And, you know, you're like, everyone talks about, this is something I just think about a lot. we all talk about like, oh, failure leads to growth or like dark times, you know, darkest before the dawn. Like there's all these cliches and adages. And I'm just as, you know, responsible because I spout them on Twitter all the time.

But the reality is that like dark times, failures, whatever, they just fucking suck. And like no matter how much, excuse my language, like no matter how much, you know, you like read those things and say them to yourself, whatever, when you're in it, it's just dark. And sometimes it just stays dark. And you're just like down. and you don't know when it's going to come out. You don't see a path to it being good or green. And you're just like, it just sucks. And there's no way around that. You just have to kind of be in it and go through it. And this seems like one of those moments.

But on the other side of it, obviously, was a lot of, you know, really interesting experiences. You get better at suffering, which is a crazy thing to think about. But it's like the first time that you suffer, you're just like, wow, this is terrible. But so long as you persevere. And by the way, we're talking about entrepreneurship. We're not talking about torture, right? And we're not talking about war. Yeah, true suffering.

We're not talking about real shit. Starvation. What we're talking about is you have a thing. You're trying to make something of yourself. You're some random person in a corner. You're trying to build the world to a degree in your image more than it was before, which was zero. And so, and so, like, just stay on the treadmill. and just keep going regardless of what happens.

And then as those bad things happen, you actually become much better at handling them. This is why I don't have to say, actually my company is doing quite well. Thank you, by the way, you've both been a part of the last financing. And that's awesome. And thank you for that. Even though my company is doing well,

I don't like overshoot it and assume, oh, and then we're going to make, and then the next financing is going to be like this, and then we're going to have this much in revenue. And I'm just like, I work on today. I work on today, regardless of what happens, whether that day is good or bad. And it's actually incredibly clarifying to do that. And it's like if you are working on projects like this, whether it, what it does is a little bit as it whether you are succeeding or failing kind of becomes beside the point.

And I will say like in entrepreneurship, like because I coach CEOs, right, because practice, the company that we're talking about here is a software platform for coaches to run their businesses. And so as a result of that, I coach first time CEOs. And when you see the inside of their business, it's like it's not fucking easy out there, ma'am. And so like to anyone that's listening to this is like, these guys seem maybe they seem to have it figured out or something. we truly do not. Like we're just really doing our best one day at a time and maybe we have a lot of suffering behind us. So we've made a lot of us.

I love the we suffer less because I think that's so true. I remember 2011, 2012 coming from Montreal to San Francisco, put all my money into this video discovery startup I was running called Phi Bai Bai. And I was literally like reaching out to anyone who would talk to me. And I went for a hike with. this entrepreneur and I was telling him what I was doing and he was like oh dude like that sounds exactly like insert famous consumer social app person uh is doing it sounds and I showed him the mockups he's like dude it's literally like pixel for pixel the same and I was

like could you put me in touch with him and like you know that feeling like your heart sinks that's how I felt yes put it put it put in you know we get in touch the next day we're having coffee. He shows me the platform. And it's like a, it's like not only is a pixel for pixel better or pixel for pixel the same, it's like 10x better and everything is just more thought out. And he looks me in the eye and this is the craziest thing that, you know,

it's such a crazy thing to say. And he was like, I wouldn't even sell my company for a billion dollars to Google because he had sold his last company to Google. and I basically left that coffee meeting just like, you know, crying, like, honestly. Like, I was just like, this is done. Like, this is over before it's even begun. And you're totally right.

Like, ever since then, like every, you know, big suffering event has been like less and less and less. But if you're going to sign up to entrepreneurship, you are going to suffer. period. If you're anything like me, your portfolio is a mix of the usual suspects, stocks, bonds, and mutual funds. Maybe you've even dabbled in some alternative assets like crypto. But those investments can be incredibly unpredictable. You know what typically isn't unpredictable? Apartment buildings, rental homes, industrial facilities, places we go every day to work, eat, and live. That's all private real estate. And thanks to its historical stability, as well as its reputation as a reliable income stream,

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combination for developers and clients. So hire high quality, verified, vetted engineers from Europe with lemon.io and be stronger than 90% of startups on the market. Go to lemon.io slash room and get 15% off for the first four weeks. Get there before your competitors will. Check out lemon. com. You guys are both entrepreneurs. You've both been in the arena in that very real way. I want to talk a little bit about like that first kind of that first action like you know for Julian for your first company like when you made the jump from you know being an author speaking tour all you know to your point the lawyers told you like you have a great thing going why are you making this change what was it like what was the insight and what was your first action step when you were going to jump into it I think a lot of people would benefit from hearing that because there's a lot of people who have the ideas and then don't take it. I think a lot of people would benefit from hearing that because there's a lot of people who have the ideas and then don't take it. take the action. And it's like, how do you combine the two? What was your kind of moment and how did you make that jump? You know, it's interesting. I haven't thought about this in a long time, but I was a big habit proponent back in the day. And what I did was I was using a habit app

and I wrote in it as one of my things, work on secret project. And it's, and it's like remarkably simple, right? Like I knew, I really cared about this thing. I didn't know what it was at the time and actually it was like a shitty version of the idea probably back then but i i made an effort to work on it every single day yeah and and i mean that's how it started and it it sort of grew in seriousness it grew in what did that mean to you like work on a project every single day like what does that i just wanted i just wanted to put i just want to push the ball forward in any way that i could i did not care what it was so long as i could check it off and i hadn't like you know i had a kind of intellectual honesty towards myself, like I'm not going to bullshit of myself about it.

And I said, so long as I advanced this, I can see whether or not it was something. And there came a stage where I just got an unbelievable crazy optimism. And my, like, my crazy optimism was like nothing I'd ever had about anything. And I was like, I'm pretty sure, not only did I believe that it was fundamentally going to happen. By the way, I knew nothing about it. I used to send Greg emails about, about, like I have no idea how to raise money. I'm so, like, I have no idea what I'm doing.

These people seem so smart. I'm so stupid. I looked at these emails a few months ago. It's ironic, like how it went since then, right? But, like, I really believed that I knew nothing and that I had no path to doing it because I didn't know anybody like that, like back to the network. I had nobody in my world. I don't even think I really even knew what entrepreneurship was, but I had a sense that if I

could advance it just a little bit at a time every day it would become more real and then ultimately it did and that's how I learned to become a CEO and that's how I learned to raise all this money and build a business and all of these cities and all these things as a result of just taking and just for the listeners like this is he was when he when Julian's talking about raising all this money he's not talking about you know 500k or a million dollars you know he's just being a humble Canadian here we're talking in the in the hundreds of millions of dollars lots of money in a short amount of time. Yeah.

Yeah. About $200 million. And this is a guy who literally didn't know anything about startups. Like I, like, it's, he literally did not. And then, like, he was emailing me and I was like 22 at the time or something. So, and we were kind of like going back and forth when we were in the arena together and just like, sort of, you know, doing our best and seeing what Julian did from, I want to say, what, like 2000, when did you start breather?

13. Yeah. So it's pretty inspirational because in a matter of a few years going from not knowing much about venture back startups to zero to one, you know, hundreds of employees, hundreds of millions of dollars raised, coming from a place that's, you know, he didn't graduate. from Harvard or whatever, wasn't living in New York or San Francisco, had no existing network. Like, he bootstrapped it. And he did it because he treated it like a job. I'm looking at the emails right now. And I'm looking at them. And it's literally me like

kind of vaguely not like it's like an egalitarian relationship. It's two people speaking equals. But literally me going, I have no idea what I'm doing. Do you know how to raise money? because I don't and I don't know anybody that does. And he sent me these shitty like decks from 2012 or whatever it is. And I don't even know how I got over the hump to tell you the truth. But I will say that we were lucky. Like I was lucky because I would be able to, for example, I called Gary Vaynerchalk on the phone.

It's like a story I'll never forget on my life. Because I have some of the history that probably many people don't know is I have epilepsy. I don't have a lot of seizures. But I worry about seizures a lot. And sleep really meaningfully affects whether I have them or not. And so I'm sitting in the back of an Uber back when they were just limos. And I'm taking this call with Gary Vaynerchuk because I happen like we know each other from the book world. Right.

So I am kind of more networked at this point because I've written a couple books, blah, blah, blah. And so I'm lying down like fearful of whether I'm going to have a seizure or not, which I don't, obviously. And I'm like, hey, and I say to the dude, like, do you mind if I lie down in your thing in the backseat? And I'll never forget what you said of me. He says, sir, while you're in my car, you are a king. I was like, wow. I take the call from Gary. And he goes something like, I don't have time to advise because I was just like, I was like, well, he did he even like, does he really know me that well?

And he's like, yeah, Julian has been around a super long time. Yeah, I'll definitely invest. No problem. and he just gives me my, basically my first money right there. So it's like we do have those advantages. But at the same time, like, it required some happenstance for people to just give you a shot. And that's the thing that I really never forget. And I remember talking to somebody about this recently.

It's like, I will never forget people that give me a shot. Greg, to a degree as a person that gave me a shot, being willing to kind of like help me out and learning how to do this. And as much as possible, whenever I find smart people, I'm just like I want to give them a shot. Yeah, it's like, you know, the people that, there's kind of two people that you never forget, people that gave you a shot and people that were there for you in your darkest times. I like, I always think about that. Like, you can count on two hands the people in those categories for you.

And they are so, so impactful and you never forget them. Like the person that is there for you, I call them darkest hour friends, but like the person that is there for you when shit is really bad. because it's just not convenient. It's not cool. It's not positive for them. Like everyone wants to be there when you raise a bunch of money and there's like the celebration of the round. And everyone's going to be there for you, Julian.

We're going to be like, yo, this is sick. Let's go party. We go to Vegas. You know, you just raised $100 million. Awesome. But like how many of those people are there when the shit goes belly up and it's not working and you're having to fire sale it? Like whatever it is.

Like how many of those people are still there? And it's very few, unfortunately. But those people that are the people that are the people. people that then come up over and over and over again in your life and that you want to be there with in the trenches with. Yeah. And it's interesting because like I have to say, I have these old friends of mine again from like back in the day that I stay friends with and I've been friends with them in high school or college. But increasingly it's like your friends kind of have to be entrepreneurs. It's not like universally true. But they just like get you in a way that other people

do not. And there is this mutual understanding. And again, like I'm making these words analogies. It's like two people went to war. We do not go to war. Not really. But we have a set of unique experiences that really cannot be shared with other people that have never started companies before and have never like basically smashed their face up against the wall over and over and over again until like a brick fell out. And then they were able to like squeeze their whole body through the brick somehow and

make a company out of that. Like those people that have done that. Yeah. I'm, I want to talk. about this because and we haven't talked about this you know privately at all so I'm just curious your perspective I've actually over the last since COVID basically have been spending way more my time with the people I grew up with who are not entrepreneurs and increasingly spending more and more my time with those people and less and less

time with entrepreneurs and and people like that and I've been I've been finding it to be really fulfilling because like these are the people these are your day ones and there's just something that's like wholesome and pure about it and I've really really and I've been enjoying that experience that I've been having I felt mostly like who you went to like elementary school with like I know you like in my mind I don't know if you want to talk about it, but like you have this group of people that you, you know, share an experience with on a regular basis. I don't know. We can cut this out if you don't want to talk about, like, do you know, no, no, but what he's saying, what he's saying is he, he, he knows that I've

been playing Dungeons and Dragons with the same people since I was about 10 to 15 years old. That's what he's saying. Go ahead. That's like a stranger thing stuff. I love that. Stranger Things is the cool version. This was way before that. Well, I mean, I actually, that's like what I respect about you. One of the things I really respect about you, Julian, is that you have both worlds. Like, I feel like you spend time with people who are entrepreneurs who are building incredible things, investors, that sort of thing. But you also, even when you had raised all this money and you built this huge company or you're starting a new company practice and it's starting to scale, you're still, you're still making.

making time for those day ones and that's really like I respect that and you know that about me like too like I really like I don't I wouldn't want to lose that that wholesomeness and purity I'm just curious your perspective on it yeah so I mean I agree with you I know that you have always been I don't have to write phrase maybe it is family orientation actually I would say you're more family oriented than me, but I have recently become more family oriented. It just happened to be my father passed away, like right before COVID, thank God. And I was suddenly left with mostly my mother's side of the family, and I found that I could bond with them in a new way, which I've now begun to do when all of a sudden I feel like I'm part of the family, almost like a clan in a way

that I didn't think before. But I was, I distinguished that from these early longstanding friends of mine that I've had a really long time and that probably are the people that keep me grounded. Because otherwise my identity would have been too attached to I run a startup. Oh my God. I'm, you know, like I'm the second coming. And then when if the company is tanking, then I'm tanking and I'm worthless. But I had this kind of like separate ability to identify. Like I had a separate ego where I felt, you know, it's because of the fact that they never cared.

And even now, I'd be like, oh, yeah, I raised like $25 million and seems to be going pretty well. And I met Warren Buffett or whatever random thing. They're just like, I don't care. I don't care. It's incredibly comforting, right? Because clearly they got to love you for you around you. Yeah. It's good to have people around you that just don't care at all about the thing that, you know, other people would be, like, wowed by.

It's just like, it's grounding and humbling at all times. You're totally right. but but I think that to a degree people like us you kind of admitted it and I'm admitting it here is like like we're trying to prove something to other people like maybe our own self-worth maybe we're trying to prove it to ourselves and so when someone doesn't acknowledge that that you're just like okay you like me for me like that's weird why I don't get it depends on who on I guess it depends on who it is in your life like there are very few people that I think most people are willing to be 100% authentically themselves around.

And you can say that you are that way around your partner, spouse, etc. I would argue that most people actually still aren't. They're still presenting a better version of themselves because it's very difficult to be like truly open yourself up in every way. I think maybe with like your parents, you are that way or with your, probably not with your children, but maybe with your parents you're willing to be that way. but it's like a scary thing right like I remember the big moments of my life like big turning points of like going to you know going to school and going from being like big fish in a small pond to going you know I went out to Stanford to play baseball and I was like really bad at baseball relative to most of the players on the team and not very smart compared to most of the students in my classes and that imposter syndrome that I felt and that insecurity that I felt was like highly motivating but also like quite disturbing at times I mean just like dark. dark feelings of constantly being stressed. And like, you know, it's like the duck syndrome of

everything looks fine on the surface. And you look and you're like, oh, everything's great with this person. I think we constantly do that, by the way, with entrepreneurs. You know, we look at these people that have made a billion dollars or made $100 million. And we say, like, their life must be awesome, man. That like, so cool. They must be happy all the time. They must be great. And the reality is that a lot of these people could best be described as tortured. I think I heard like Patrick O'Sagnesi maybe say that or tweet that about amazing people he had talked to, a lot of these people, like there's real downsides to, you know, having this unbelievable ambition and drive to go achieve more and more and more.

There's a darkness on the other end of it that comes as part of that kit, quote-unquote, that is very, very real. Yeah, you, I often refer back to this whole story about John Rockefeller, Sr. who was the richest man in the world at that time, and who was an incredibly incredible family man, but also super stingy, even inside of his own family, like totally terrorized people like John Rockefeller Jr., we know as the person who built Rockefeller Center,

and who was a cutthroat monopolist, but at the same time, was able, due to his monopoly of oil, to stabilize the price of oil, oil and as such enable stuff to be built on top of it, which could not be done when you add all of these oil fields that some of which were being built and some of which were going bankrupt and all these other things. Instead, he silently bought them all underneath, right? And so you've got, and by the way, later on, like, was able to revolutionize medicine

as a result of all of the funding that he was able to give it and turn it into a real science, many people say. So you've got these people. that like we just have to give up on them being normal like the idea that they we should just be able to carte blanche think of them as being successful and they're just great and if you meet them it's going to go well like it's not like we are close to these people you know it's interesting i was once having a conversation with um because i was funded by one of peter teal's venture funds called valar that focus on investments outside the united states at the time and And I was having conversations, and I would be like, yeah, I kind of, I don't even know, I should

be saying this, but it's like, I was like, Peter Thiel money. I was like, we were very candid with one another. It was actually a pretty solid relationship. And I was like, I don't know. It's not like the cleanest money in the world. Like, it's kind of a weird dude. And because I would just say anything. And he was, the two guys that run this fund were like, you should see what's out there,

man. It's not clean out there either. He's like, this is pretty good. And so I think if we like we separate completely, and I know it's very difficult to do that, we separate the acts of success and the things that they have built completely from the person. That way we can be like, that's super cool that you built PayPal and then this and then this and then this and this. And maybe you do drink people's blood.

Like it is possible at this point. You know, I don't know. So if we do that, I think that we'll be able to know. normalize this idea that people are, that they're special. Instead, we're able to say they're actually not special. They just work exceptionally hard. And it doesn't mean that they're like paragons of virtue. And it doesn't mean we should worship them.

We've built statues about them and all these things. They did a really good thing. They did a really good thing. It doesn't really say anything about who they are at all. And I think that would be very psychologically healthy for a lot of people. So before we get to the end of our time, I do want to just get into the weeds a little bit on Julian, on what you're building now and sort of like the indirect and direct ties to what you had worked on before. So breather, you know, for people that aren't familiar, was like, you know, unique spaces like you could, you know, book spaces to get a breather, which like, by the way, it might have been early for its time and maybe there were flaws in it, which you can talk about separately. But it's like a great concept, right?

Like everyone wants a breather. The idea of it makes a ton of sense. And candidly, like, if you're in a city and you can find a space to actually just catch your breath and like meditate for a few minutes or do a call or just get away, totally makes sense. You worked on that. You mentioned earlier that, you know, there were things as a first time entrepreneur that you really learned and that you're applying and approaching differently with practice,

which is what you're building today. can you talk about that transition from being kind of a first time entrepreneur to a second time and how it's informed your building process for what you're doing today? So I will say this. What I'll do is I'll maybe compare it to the book business, right? And so when you're in the book business, what happens is you have hits and misses. And hits and misses, it's just like, well, that book did really well. And in that book that I wrote, thought it would do well.

and so I'm just going to kind of keep writing them and it's kind of a crapshoot and there's much more of that kind of like Picasso effect. I don't know if you've ever read this book. It's called Young Geniuses and Old Masters. And the book is about the two paradigms for how to become better. One of them is you have a game-changing thing that you do early in your life like Picasso.

The second type is the type like Matisse and Matisse who's just endlessly doing landscapes up until he's 95. and he's doing the same landscapes, and he's trying to make them better and better and better and better. And so even though I have had these moments in my like, kind of like earlier years where I was able to do these kind of vaguely kind of young genius moments, I have settled into a state in which I am just consistent,

just working on the process to improve. And so one of the big changes for me is I learned how to become a CEO in a, in a much more of a pressure pressure cooker way than most people. Most people start a company and it kind of got to go somewhere, like sort of, and I don't and I know. I learned to be a CEO by raising $150 million, scaling a team from zero to 250 plus people in under like three, four years maybe, and building a category or let's say a category entrant out of scratch,

from scratch and literally having kind of like not that much mentorship around me. And so I had this crazy ride, but now I actually know, it's this weird thing that I've kind of come to grips with recently. I actually know how to be a CEO and run companies, and I actually like am good at it. So it's a different thing. I've like found my place. People ask me often, will you write another book again? I wish you'd blogged. Like, I loved your podcast, like all these different things. I considered those projects in a lot of cases that I would do for two or three years. years or some other thing like that, then I would maybe get burned out on them and I didn't want to do them anymore. Whereas being a CEO, I actually am good at and I can keep doing for a really long time. And this is this kind of like weird chrysalis, like awakening moment when I emerge from the lotus blossom or whatever.

And I'm like, oh, wow, like I actually am really good at this. And this means that I can impact a lot of people. You ask me a little bit about the thread. I call it a red thread. It's an expression I got from Tansan McMahon, who is another author. And it's this sort of through line through your life. And this idea of this through line through your life is like, that's been sort of the thing that you have valued all throughout it.

And for me, going back to the sort of the beginning and feeling like an underdog, I always want to give people individuals more empowerment than they have them than they've had. And so I did that a breather, and all my books are about that. and practice is really intended to serve solopreneurs. So it's kind of the same thread all throughout. And I realize, one of the things you realize when you start a company is you kind of only have a shot, a couple shots if it's going to work well. And if it is going to work well, like you've had, for example, Alexis O'Hanning on this show,

it's like you don't have like 50 shots. You've got like probably five to really make a difference at something. And I thought, well, what is it that I really care? and I went back throughout my life. And I said, what are the things that I cared about today at my age, but that when I was 20, I still cared about. So those are the through lines. And I went through them.

And there's not a lot of them. And I said, those are the things, probably the only things that I can start businesses doing, because it's the only thing I'll still care about in thin years. And one of those was this idea of individual empowerment and being able to help individuals and allowing them to, like, become better and to get higher leverage and be more successful with little. And so that's why I started this business. And that's for me, probably that that deep care that I have and that my team has today is probably one of the reasons we're successful.

Do you still enjoy it? Like, do you feel a lot of energy around it when you, when you wake up? Yeah. But I had to set boundaries for myself. A lot of people like out there are like, why would you start another venture back company? It's horrible. Right. Like, because we, we talk like a bunch of us that have raised money.

before are like, are you talking about me? I don't, I'm not talking about you. In this case, I just think about somebody else, but there's a lot of people who believe that. And I actually like, I know that I'm entering into a contract in which I get extremely high leverage as a result of some weird like category risk, which you wouldn't get if you weren't taking venture back, venture, venture financing. And I'm conscious of that risk and I really embrace it as a result of being able to accelerate. Because what happens in venture back company is anyone who's here who started one, Greg knows,

I definitely know, is you get this density of talent that's just unbelievable. And you meet people. You're just like, holy fuck. And by the way, one of the people is someone that you referred to me, dude, is that literally we were looking for an onboarding specialist. We hired somebody. and they were someone who listened to maybe that followed y'all's Twitter feeds and listened to this show. And his name is Rahul.

And he's been on our team for three months. And just now right before this, we were talking about him. We were like, I can't believe this rando just showed up and is so excellent at this stuff. You just find these people, right? Other people, maybe people will be jealous on my team because I'm talking about one guy. We have a great team of people, but this is one that kind of came out of nowhere. And I love finding undiscovered people. I love making them more excellent when I can.

And I love being able to build something with small teams of people really feeling like a tribe. I love that. So I actually like it way more than last time, but I needed to set boundaries in order to allow them to happen. There's so much that I'm taking away from this conversation, like personally and professionally. I mean, one of the things that's been a big takeaway for me is like this idea of the red thread that you just raised, you know, and like the through line through your life. And being really thoughtful and introspective about that through line, you know, you just mentioned it. Like, your ability to reflect on each stage, what you picked up, what the just like painful losses

were that really did nothing and compounded in no way. But use everything in kind of every little lesson and learning along the way to, you know, hopefully ultimately lead you to a place where you're deriving a ton of energy from the things you're working on and doing. I mean, I'm coming away, feeling quite inspired around all of that. Greg, I don't know. My big takeaway is be like, be like Matisse. Like I had never heard that before. And although a lot of people, including myself, might be envious of being a Picasso.

It's just way more consistent to become a Matisse. I think anyone could become a Matisse if they just put in the work and sort of focus. And, yeah, I mean, also, what would Julian do? WWJD. I should swap my hat. I should swap my hat. Yeah, buy that domain name.

And my last takeaway for everybody that I had written down as we went through was that secret project, that idea you've had, find a small, small way to work on it a little bit every single day. And I love that when you said that because it was like, it takes the intimidation factor completely out of it. If you just think of it as like, I'm going to do 15 minutes on this thing a day. I have this like 30 for 30 idea where you just spend 30 minutes a day for 30 days. And at the end of that, you know, you have 900 minutes of accumulated effort on something. It's bound to make forward progress during that period. And that can be anything, cardio, you know, workouts, whatever it is, writing, et cetera. But like a secret project,

If you just find one small way to push the ball forward every single day, it's pretty amazing what you can accomplish in a short period of time. So that was my one final takeaway to leave people with. This was awesome, Julian. Where can people find you and practice? Practice is at practice.d.do. I'm at Twitter.com slash Julian. And, yeah, I mean, you can just Google me. I'm all over the place. But thanks very much for having it. This is true. This is true.

And if you are a solopreneur, you know, Greg and I are both biased, as Julian said, as proud investors in Julian and what he's building. But they're building an amazing operating system and platform for solopreneurs to effectively do their work and scale and grow and empower them. So really proud to be investors, proud to be your friend and excited for everyone to get to listen to this and hopefully take things away from it. Thanks, man. Thanks so much for having me. Thanks so much for listening to today's episode. If you have any questions that you want featured in a future episode, email us at high at t-R-W-I-H.com. Leave us a review at Apple or Spotify to help us grow the reach of this podcast.

Until next time, we will see you soon.