#16: Julien Smith, Practice

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 16, and I'm so excited to welcome Julian Smith to the podcast. Julian is really eclectic. He's a New York Times bestselling author and the co-founder and CEO of Breather, which was an on-demand flexible office company. He is currently the co-founder and CEO of Practice, which is a platform and one-stop shop for coaches to get the resources and tools to build their businesses. We had an incredible conversation and we covered so many topics, including what it was like for Julian to step away from being the CEO of Breather and what he learned from watching another CEO operate.. We discuss the importance of co-founder relationships and the specific tools that he uses with both his co-founder and his fiancée. You're not gonna wanna miss this, so please enjoy my conversation with Julian Smith. Julian, welcome to the show. I'm so excited to have you here.

Thank you so much for having me.

So, you know, Julian, we can start in so many different places. You're super multifaceted. We can go in so many different directions, but I saw on your website something I wanna ask you about, a short course on being awesome. Tell us all about that. All about the key to being awesome?

You know, it's interesting, uh, for a long time I ran a super popular blog, which is where that comes from. And that particular thing, I think, ended up in Cosmopolitan or whatever rando magazine. And, uh, and I— but, but my answer, I think, today would be different than it, than it was when I wrote that. I, I would say that, that one of the biggest things, what you realize as you get older, is, is that life is really short. And, and so if you can First figure out who you are and be authentic to that. That's probably the most valuable thing. And I think what I think is what I say in that post is like, awesome to whom? Like, you— that, that can't possibly apply to everybody. You're always going to have haters, you're always going to have people who love you. Hopefully, hopefully people that love you. Uh, and, uh, and so, and it's about finding your tribe, your tribe of people that you really care about, right? Those are the things I think probably critical to it.

I love that. I love that, the notion of awesome to who. Really, I would say, Julian, honestly, self first, right? Awesome to yourself first.

Yes. Yeah. Put on the oxygen mask. Absolutely. Yes.

Yes. I love that. As I was exploring your website, the other things, or Googling you before this interview, you also have a tweet explainer on your YouTube. I love that. He's going through all his tweets and explaining them like the comedians sometimes do. Specifically, you reference your tweet, "So easy to dunk, so hard to build." Yeah. Yeah. Tell us what that means to you.

I guess I've been on the internet a really long time building things. And so because I have, and because I've had small projects, like as small as a blog post, and bigger projects as big as a pretty meaningful, you know, what we would call a scale-up maybe. That you're just aware of a set of categories of people. And by the way, not everyone is like a person who naturally builds. Like, that's okay, like, if you're not that person. But then— and that's perfectly— like, be that person if you want, but, but don't be the type of person who is not building and then instead you just dunk on people on the internet. Like, just— that's, that's— there are many acceptable categories. To me, that just doesn't feel like one of them. And so I I think what happens as you build things or as you write things or write books like I did in the past, that's why I say things about focusing on your tribe because so much of it is about being able to reach people for whom your voice is meaningful. It's meaningful to them. When I say, "So easy to dunk, so hard to build," this is on Justin Kahn's podcast that you're just referring now. It's, it's because, uh, it is, it is so incredibly easy to see. It's, it's all we do all day is like we see like a thing on the internet and we judge it. And it's like, that's what you're doing. Like even if, even if you're building, 99% of it is like you see it and you judge it. And then after that it's like, well, I'm gonna post. And so, uh, building is such a long-term commitment. My, uh, my fiancée is a ceramic artist, right? And so she'll work for 20 hours or something on one project and it'll crack at the end, and she'll have just spent 20 hours on something and it's, and it's trash, and, and she can't do anything about that. That's just like an act of God, right?

And also kind of like a, like a, just a, um, something that happens when you do ceramics, right? It's like an occupational hazard.

That's it. It's normal, right? Yeah, you can't control it. It was like an air bubble and boom, it explodes. And so it's the same with Anything when you build, building is— it takes, takes a long time, takes a lot of effort, takes a lot of hearts, takes a lot of will. Dunking takes none of those things. And so I, I prefer one over the other mostly, you know.

You know, I can already tell in this discussion that you're a very sort of intuitive and I think feelings person. Something that you said was that feelings are a valid form of information and that founders get this feeling, this instinct. You know, I know a number of founders who even would sometimes feel like they're a like they can really, they have a knack for understanding what's going on. Could you talk about the notion that the founders feel it first and then the numbers show it?

Yeah. Uh, you know, it's, uh, when you build, when you build things, it's foundationally, it's based on instinct, right? And, and it's, that's what happens. It just like it happens in ceramics and you build something out of nothing and you don't know what it's gonna look like. Uh, I was watching like a Michelangelo documentary on YouTube. The other week, and it was all about being able to see the sculpture inside of the marble and being able to expose it, not creating it, but rather exposing it. And so I think when someone is an artist or a creator or a founder, what they see is they see an unvarnished set of tiny little signals. They just see little things. They're like, ah, like this interesting anecdote. Um, Michelangelo's Statue of David was actually made from a very old and, and actually used piece of marble, uh, and it was exceptionally narrow as a piece of marble. So it wasn't like a big block. So you would imagine it being a big rectangle, right? But it wasn't. It was actually exceptionally narrow. So it forced Michelangelo— what it does is the constraint forces you to think about what it— something is going to become. And so as, as a founder, what happens is, is you talk to users and you talk to them like really intensely, and you look at a market and you have to examine it from many different perspectives. I'm not— no, I'm not saying founders are all Michelangelo, nor that I am, but like, but the point is, is, is you have a set of pattern matching that you are able to apply to things. And so none of that applies because the numbers are not meaningful to, like, an investor or to someone who's not in the space. And so they want to see a graph that's up and to the right, and you try and deliver a graph that's up into the right. But it doesn't begin that way. It begins with, man, I had this conversation and someone says something interesting, and that sticks with you. And maybe you write it down, and maybe it's not the right time for that, but 3 months later you come back to that phrase and you're like, yeah, that was really weird when they said that. At Breather, I remember the prior company that I started, Gary Vaynerchuk was one of my first investors. And he called me and he said, hey, Julian, listen, I've got this team of people. And we had already had like maybe 10 spaces in New York or something. It was very small by that point. And he said, could we just, like, we just need an extra, like, a certain amount of square feet. Like, could we just take this space for like a month? It was right before my Series A. I'd raised $1.5 million. I was on my way to raising $6 after that, but I didn't know that. Uh, but I was aiming to do something like that. And, and, uh, at the time I thought, oh yeah, like, I guess so. That's not really our model because our spaces were, were, you know, really for chunks of 2 hours or for 3 hours or something. And he was like, I want it for just a whole month. What I only realized many years later— in fact, that the majority of the market was going to be like that and was going to be in giant chunks of 1 month or in 2 weeks or 6 months sometimes. And we would have million-dollar customers down the line many years later, Spotify being a good example, where they were just like— they were just taking up like 20 of our spaces for like months at a time. But that initial signal is something that you don't catch in data at first. You're just looking at it as an instinct and you think Oh, that's interesting. And then later on down the line, it becomes data. And to most people, that's when it's interesting. That's when you invest, when there's data and all these things. But there's a set of people for whom the feelings are really important, and founders have to be that type of person.

That's really interesting, especially in the case of Gary Vee saying that to you, and you're saying, well, yeah, sure, okay. But then did it— when did it become like a tingle in your spidey sense? Like, wait, this is actually going to be a thing?

Well, you know, the interesting thing is, is that when you're— when you actually Uh, when you're a founder, you have a choice as to what to follow. And so in actuality, uh, it took a number of years before we were like, oh yeah, sure, yeah, I guess this could be the thing. And as soon as that happened, like, like the, like the business was growing like really fast. It grew really fast for a number of years, but only later down the line where we're like, oh yeah, for months at a time, like That makes a lot of sense. And as soon as you pointed at that, you could then say, oh, of course, like, in hindsight it's obvious. And I heard about that for the first time in 2013, but it was only like 2017 or something that we really started taking it seriously. But it began early.

Yeah, it began early. You kind of had— it began to sort of almost nest inside of your head early, I think.

Yeah, like an earworm. Well, if it was a song, it would be an earworm, right? It just sits there in in the back of your mind, right?

Absolutely. Well, I love that you have all these sayings, and another of the sayings you have is, the bigger chip you have, the bigger chips you get. And basically you said that founders have complexes. The more you doubt yourself, the more you go out there and you kill it. So I wanna remind you, you said that. And then I'm curious, what's your chip, Julian?

There's a few things. Like I wasn't, well, I think a lot of founders, a lot of people that are, have, have built up something for themselves, like online or building companies or whatever. A lot, I think a lot of them come from that kind of like standard, uh, you know, Stanford, Stanford, YC, kind of like dropped out of Harvard thing. Like, I, I don't have any of that. And so I like, I just, I have instinct about things and, and, and, uh, and I like to follow it. And actually, the more people tell me no, the more I'm like, oh yeah, I feel that I have always been able— I'm not always successful, but I always catch on to things like really early, sometimes too early, definitely. And, uh, but the result of that is when you catch on to things early and you tell people about them early, they're like, whatever, that's stupid. And so I, I think I've been told like, whatever, that's stupid, like, like fucking a million times. And so that is certainly like one of the major ones. I will say there's a really funny anecdote about like, uh, Jeff Bezos as he's, as he's coming out with like the Kindle Fire phone or some shit online on, on, uh, on stage. And you— so he does, he does this little bit, and, and what he does on, uh, during his presentation is he goes like, okay, so in 2010 they told us we couldn't do this and we did it. And in 2012, they then told us we did this, we couldn't do this, and turns out we did that again. But, but in his eyes, like, you could see that he's like really mad, right?

It's not just like stagecraft.

He's like, he's like, he's like, those fuckers, you know? That's what he's thinking. Uh, and so, uh, you know, it's interesting because, uh, there was this whole conversation about like by a Founders Fund dude this week on Twitter about how, uh, if, if you, if you have like a media, like, like kind of a medium-sized outcome when you're too young, it could be really destructive to the potential as a creator down the line because you had this comfort that occurred to you all of a sudden. All of a sudden you went from whatever, $0 to, I don't know, $5 million or something in the bank, right? And then now you're like, but why? Like, why should I do anything? And so, and so it's, uh, I noted between my, my two companies that I had built, I had, I'd kind of like looked at a bunch of, uh, entrepreneurs like that are, that were well known. And you would, I would look at Jack Dorsey and I look at Steve Jobs and a bunch of others, and I would note that there was always under 18 months in between the times that they had spent building their first or leaving their first one and then starting their second one. And I don't know if this is like a real number. Like, I— this is just an anecdote that I myself noticed. But I think that what happens is you wait too long and you had some kind of outcome, uh, then you're just like, you're just gonna like go like whatever, surf on the coast of California, which is— I, I do, but I, I do less, less time than most people.

Right, right. So it's like the fat, dumb, and happy.

So you got to keep that, you got to keep that hunger, and you also gotta let yourself get into something. It's really bad. I know founders that have, um, that have started something and then they left their business or their business got sold or something, and then they started something within 3 months, and I'm like, oh God, no, right? So there's a, there's a sweet spot. If you wait too long to be able to do it, then you're not going to get— you're— that hunger is going to leave you a little bit, right? Ultimately, from a chip perspective, for me, it's really a little bit about, like, turns out I really actually really like building. Like, I'm in my 10th or 11th year of being a CEO, and I really like it, especially with good teams. Uh, but in addition to that, certainly I'm, I'm all about, like, like, finally, like, feeling like someone acknowledged that I'm decent at this, you know? And, but it's just gonna kind of per— it's probably gonna drive me like perpetually.

Yeah, I hear you. It's like, right. It's sort of this, this, that's your chip in terms of the driving and also the validation and the proving. And I love that. And especially you talk about, you just talked about being the CEO for about 13 years. So let's talk about Breather where you were the CEO obviously, and you co-founded it with Caterina Rizzi in 2012. And I think it's sort of very clear that you were seeing this trend pre to early-ish for sure. And you started Breather, which was this, uh, a company which allowed people to your point to rent spaces, to be able to reserve spaces for 2 hours, 3 hours, maybe a day to be able to use a conference room or a room as necessary for an offsite or a business meeting or something. Breather was a great service. It was fantastic. And then you stepped down as a CEO in 2019. And you brought in the experienced executive Brian Murphy. Tell us what your decision process was like for stepping down.

Yeah, it's, it's actually, it's a fascinating sort of, uh, a, a lesson in starting, uh, companies and then what, what that turns out to look like down the line. So it's more like 2013 ultimately when we really begin. I, but I begin it trying to really falling in love with a product, a product that doesn't exist but that I can conceive of as existing. Really different than practice here, uh, where now I've almost like— it's almost like fallen in love with a mission or a consumer, right? Different. It's almost like a different orientation. And so I'm like, oh, we could get these spaces and we can put electronic locks on them, and then if you unlock— I mean, you, you're in New York, right? And so you've been in Manhattan. Manhattan had at the height of it, like something like, I feel like 200 breather spaces or some crazy number. And the business was growing and growing and growing. And so I was like, it would be super interesting just to be able to get away, especially in a dense city like Manhattan. I was like, that'd be super powerful as a thing. And it turns out it was. And so what continued to happen is that I was like, yeah, this is really cool. A lot of people thought it was really interesting. They used it, the revenue grew, and all these other things. We raised more money. We ended up raising $150 million at the end of it, uh, under me anyway. And then I was like, oh, I'm in the real estate industry. And then that's when— was one of my reasons that my perception changed, is— and it's something that actually a coach, an executive coach in Silicon Valley, not mine, but an executive coach in Silicon Valley, did tell me at one point. Is that you have to love the customer in order to be able to do what you do. This is something I didn't really understand. I had built a product that I really liked, but all of a sudden I was at real estate conferences and, and I was like, I was like, could I do another 5 or 10 years in, in, in the real estate industry? And I, I wasn't confident that I could, but I knew that this could still happen The process was voluntary and it was based on— okay, after 6 or 7 years of basically learning to be a CEO on the job, and I think more succeeding than failing, I was like, another 5 years like this would be crazy. I was completely overwhelmed. I would definitely say that I was also under-mentored in a lot of cases. But I learned an incredible amount. And so, uh, in short, it, it really drives a lesson of you actually only have a few shots at really changing something. And remarkably, we were in a— keep in mind, this is like the height of WeWork and like a bunch of other things like that. And real estate really had an opportunity to be transformed. Now it has been transformed, right, as a result of COVID Basically, which is also like Breather, like, was like swallowed by COVID, and WeWork was swallowed by COVID, and lots of these other companies were swallowed by COVID. And, uh, but it wasn't— it was, it was on the cusp of becoming transformed. But it turns out in your life as a person who builds companies or who starts products, you actually only have a couple of shots at really making life-transforming industry-transforming things. But that's not because you might only have 2 or 3 ideas. It's because it takes 10 years to actually change something meaningfully, right? Like, I think Stripe is 10 years in, 11 years in, and, and, and Amazon is like, what, like, like 30, 33 years in or some crazy number, and it's still like e-commerce is only a small percentage of all transactions that occur. In, right? So it's like, it's got to be long. And so ultimately, I just discovered that this, this was not my fight to continue to do. But I'm actually very pleased that I was able to continue to build things and to renew my excitement in building things. And more importantly, and back to the chip on the shoulder, to discover that what— that my success was not a fluke. And I think that's one of the things that really motivates repeat founders is like, "But was I just lucky though?" And to discover that's not the case is very empowering.

Yes. Oh my gosh, so much in what you just said. I want to really double-click a little bit on what you said about being overwhelmed and under-mentored. Tell us about feeling overwhelmed.

Yeah.

And tell us about— I mean, it's sort of like under-mentored kind of speaks for itself, but I'm curious to unpack that. Yeah. So overwhelmed first.

Well, I will say that like something happens when you're out. Like, often people talk about like being an outsider, but like, so I like, I really come from nothing. Like, I'm very proud of where I come from because like I said, my father is a, was an exec coach and career coach for 40 years. That not only caused me to, uh, to build this business that I'm building now that's actually going quite well, but it also caused me to be able to choose what I did versus like someone telling me you have to be a doctor. When you have a career coach as a father, he really says— it really causes you to then be like, wow, I could really do all any of these things. So that's super compelling. Uh, but at the same time, I had a huge amount of outsiderism. I talked to you earlier about how Gary Vee was, um, one of my first investors at Breather, but there were very few like people that I knew that were like, you know what, yes, I'm some meaningful, like, huge VC, like, here, and then all of a sudden everyone believes in me. That phase of always believe— some— everyone believing me actually never happened while I was at Breather at all. I just gradually fought my way into the mainstream until— until millions of people had used the Cervass And then finally we're like, wow, okay, I always thought that this thing was too crazy to sort of, to, to like exist, but it exists. And it's remarkable now to be able to, um, uh, talk, to talk to people. I had a conversation with a founder, uh, when we were raising our last round, Andreessen Horowitz round that was just led. And, uh, he was like, you started Breather? I was like, yeah. He was like, I will put, I will put in $2 million. It was just like that.

Wow.

Never met.

Wow, the worm has turned, right?

But keep in mind, like, and it does take a big team of, uh, of people to succeed, and it's not— but I'm saying a lot of that was just an enormous amount of personal will. And so, so I would say under mentored, what I meant, what I really mean is, is people that had done it before and that could show me the path. And actually, since, as you know, you're since you coach people, you know that the path of just being able to light the path for other people is incredibly clarifying. I was speaking to Chad Dickerson last week or two weeks ago, who was the CEO of Etsy while it went public. He's now an executive coach. And so since— I mean, obviously he's been a bigger, higher-profile CEO than me by a lot, but to the clients that we both— we don't share clients, but they each individually have— to be able to just say, no, no, no, no, I've hired this type of person before that you're thinking about hiring right now. That's a huge mistake. Don't do that. Here's why. To have that set of people around you that you can do that with is incredibly clarifying. And it's just, it's, it's, it's a little weird. It's, it's weird to say that it should be accessible on demand. I don't know if it should be accessible on demand, but holy hell, do I wish that it was more accessible.

Yeah, absolutely. It's so very helpful for people. You know, I haven't been a founder myself, but having been a coach for 20 years, I've seen that movie myself over and over again. And so when you see the pattern over and over, you can give that kind of advice. And we'll talk a little bit, in a little bit, about practice and also about coaching because it's an interesting, you know, sort of the purist coaches who just wanna ask questions, right? And don't, you know, sort of share their expertise. And I just think like for founders in particular in the startup world, sharing your expertise is so powerful. And for you, you know, you talked about being under-mentored and overwhelmed. The overwhelm sounds like it was also— you had to really pull yourself up by your bootstraps emotionally and mentally, and then do all the things yourself without anyone helping you light the way or helping you figure it out.

I, I will say, uh, I would never start a business—

we—

I, I had a co-founder at Breather, and I have a co-founder at Practice. At Practice, Ben Neville, my co-founder, is— is— was the CTO at Breather for, I feel like, 5 years, at least 5 years. So we've worked together for a huge number of years. And I will say that being able to really to take the emotional burden, which is actually much more, uh, difficult in a startup than the work— like, the work is like kind of like— I don't want to say it's easy, but like when you're working on product-market fit, like it's an iterative process. You're listening to people, you know. You might be stuck in a corner for a while, and then you get out of the corner because, like, you heard something and you followed the feeling and you went for it and you got there, right? And so once you get there, then, uh, it's less the work and much more the emotional burden of the next thing. Okay, now I'm responsible for 15 jobs. And, and, uh, and, and so the, the emotional labor being shared is so valuable that I, like, every time that I would start a business, I would practically want to start it with, like, more co-founders. Like, again, like, next time 3 people, next time 4, you know. And just, like, to, to have the emotional burden be shared among a set of people, it is incredibly valuable to do that. So, so there are, there are founders that I coach. Again, I only coach first-time CEOs that are venture-backed, right? That's it. And so for those people, in a lot of cases, even with an exec coach, even sometimes with a co-founder, even any number of different people around them, they're still isolated, right? And so it's almost like, uh, well, I think— I don't know that this is that much— it's almost a cliché maybe, but like the emotional labor of starting a business is just as difficult as the everyday work of finding the first customer, the sale, hiring a person. That's why Paul Graham in his like YC articles, he's got like 13 things to about startups. One of them is like, don't give up, don't get demoralized. That's it. If you do those two things, you'll find your way through. I think that's true.

It's so true. It's so true. And, um, that emotional labor is what does make people feel demoralized and then also kind of exhausted. So I can totally understand that. And so, but also, you know, just getting back to Breather, clearly you just felt like this is not the thing that I want to keep doing. And then sadly, Breather filed for bankruptcy. I don't quite know the status of Breather exactly right now, but obviously there was a comedown. And I just want to ask you candidly, like, what was that like for you? You know, you had already transitioned away, but what was that like for you?

I will say this, I will say, uh, um, to have a, a person who is, uh, another CEO than you, to, to first of all to watch them operate, because I was on the board the entire time that Breather existed, is actually incredible, like an incredible learning experience and taught me how to be a better CEO, which might be a controversial thing to say.

Oh, I'd love to hear more about that. What do they teach you?

So I mean, you just learn how to operate like properly with less emotion, because as a founder you have a lot of emotion surrounding your thing and a lot of attachment. And as a, as a non-founder, you don't have that same feeling. So that's like maybe one of the core things. But I will say, it is, you know, it sounds like a funny thing to say, but to have COVID cause the prime— be the primary like damager in your business is actually kind of emotionally Fine, because it's not like people that weren't operating properly. They were actually operating at a really high level. And so like, to, to have a white, uh, what do they call it, a black swan affect your business in such a big way. But I will say, uh, it, it is, it's almost like, well, that's a very clear, like, you, it's just like not the blame is not really in the same, can't really sit in the same places, right? But I will say that, um, that I'm incredibly— I, I dodged a bullet due to the timing because it meant that I never ran a business through COVID, which I guess in a way, like, I would be more battle-hardened, right? And probably, like, I'd have more PTSD if I did. But because I literally— I was building product for Praxis starting when COVID started, basically. And so I was never in a phase where I had to, like, hardcore operate through, like, be— and be a wartime CEO the way a lot of other people did. And so that is— that I would— I— it's actually— it's funny because it's almost like the question is like, did it— was it hard? I'd be like, well, considering how hard it could have been, it was actually relatively easy, right? And I'd say like a bl— let's, you know, you say count your blessings. It's definitely a blessing for sure.

Yeah. Wow, I never thought of it that way. That's a really good point. It is true that, um, It has been quite traumatic. I mean, I think that a lot of the CEOs obviously bounced back quickly that I work with anyway. And also it was super traumatic and there's still a lot of fallout from that. So I really get that. You know, I do wanna talk about practice and I wanna definitely get into that, but I just really wanna go back to think about what else— as you observed Brian operating and also you were sitting on the board and so you had some also some distance from the experience. I'm curious, what are your other observations and what else did you learn about being a CEO? And also maybe even a leadership style, right, that we can then talk about as it relates to practice?

Well, I wasn't inside the business, so from a leadership style perspective, I can't, I can't really speak to that. But what I can say is it really showed me the difference between people that learn on the job and people that just know how to do it, right?

Yeah.

And so I, I, I am the same person The same qualities that I expressed to you earlier are the same qualities that I sought out. I think I'm a very quick study, quote unquote. I think I'm a very fast learner. But in addition to being a fast learner, I'm also like, okay, I could figure it out. And so my attitude a lot of the time with people that I worked with was, oh, they'll figure it out. And actually, I have mitigated that feeling today. And so my attitude to hiring has actually become— I was talking to CEO, to a CEO about this that I was coaching, and he was like, I almost feel like I'm cynical about people. He'd be like, well, there is a distinction between, like, you could be more cynical about people perhaps in general and their capacity, but you have to at the same time balance that with an optimism towards the individual. And so it is possible, and I think that that's a good balance to have, is don't assume that people are going to be different than they have been. Like, if someone is— in other words, another way of saying it is, uh, if someone is telling you who they are, believe them, right? But at the same time, when someone is— is— when you are interviewing someone, or when you're, you're learning if someone is possible, like, you can have optimism about the person while having a realism about people in general. The two are possible, and I try to hold both of those things in my mind at once. In short, it really affected how I think about hiring and how I think about the people around me, and it really raised the bar for, uh, for, for how— the type of people I want to have in my business. And that's because I realized that it is very hard to— and by the way, I was successful, right? Like, by and large successful throughout my tenure at running and operating and scaling a thing despite the mistakes that I made. And so, but even so, I was like, but we can get better people than this. And so that's when, you know, it's, it's really remarkable to have an investor today like Andrew Sonora and Tony Robbins, who's also an investor in my company today. It's just like, uh, the type— the caliber of people that it opens the door for. And when you're a repeat operator, same thing. Like, you've ran businesses and people are like— they know about them. They're like— and so like, you, you get, you get a lot of credibility. So perhaps now I've moved past the outsider status. Maybe. I still feel like an outsider.

Yeah, hard to be an outsider with Andreessen Horowitz on your on your cap table, but, but I hear you, you still have the drive. So tell us about Practice. I'm, you know, as a coach myself, when I discovered that you're running this, um, new, new company, tell us all about it. What was the founding idea for you?

Yeah. Well, it's, it's back to this thing about, uh, who, who were you gonna, who are you gonna love and who do you love to serve? And for me, because I grew up in coaching, And, and because I love serving kind of like underserved individuals, my, you know, my first book Trust Agents, which was like the big best first big, that was the first big like success I ever had like out there as a real person, right? It was like, oh my God, this big, like, and I was a 20, I think I was 29, my book was a New York Times bestseller, and I was like, oh my God, like I'm like, I have some level of credibility, like this is nice. And, and so, but that was intended towards solo people trying to build their profile online and how to do it. And that's one of the reasons it became successful, because it turns out a lot of people want to do that and should. Uh, and then my second book, The Flinch, was actually— it was the same. It was all— it was about, uh, empowering or giving someone, helping someone develop the courage to do the thing they want to do. And so I think my whole career has been around empowering individuals. And even at Breather, the first customers were therapists, coaches that use the space mostly themselves, right? And so I think that I've been following, uh, my friend Tamsen McMahon calls that, it's the red thread of your path, right, that goes throughout all the different things that, that you have done. And so I just realized that there, if I was going to start a venture-backed business, which I was very attracted by because it coalesces obviously capital, talent, because you can get, get close and work with people that are incredibly talented and hardworking and cool, whatever. Uh, and, and you can do that around something that matters to you, but you better pick something that matters to you. And so I thought, this is, this is interesting. We can serve people that are what we call businesses of one. And businesses of one are always by themselves, always underserved, sometimes just, just starting out, and they don't know what the hell to do. I was like, if I can educate these people— like, what I say by educated, I mean inform— if I can inform them to make better businesses, if I can give them the tools— like, we just put out a contract builder, and it was like this giant explosion of attention because, because it's so fundamental and nobody knows how to do it. Right? And, and so it— I just realized that if you're going to spend 10 years working on something and you'd like to bring around people that you, that you want to work with and all these other things, uh, you should do it around something that you, that you really value. And we're at the end of 10 years or whatever, you're like, holy hell, I really affected a lot of people that I really care about. Which is different than, for me, than enterprise SaaS, which I don't know, like, probably I could operate a business like that. But it wouldn't be my instinct. My instinct is to serve people.

Yeah. Oh, I love that. So much about that. As a coach myself and also as somebody who thankfully has achieved some success in my career, part of my mission is to constantly be empowering coaches, to your point about contracts, to understand the contracting process, to understand how to charge people. I co-wrote an article for Harvard Business Review about how to price your services because there's so much opaqueness. And as a solo as an entrepreneur, you don't have anybody. You don't even build a team around you. You just, you're just sort of a person of one finding resources around you. So I, I really applaud you for kind of finding this, this, uh, well, I watched my father do this, right?

Yeah. And so, and by the way, like, it, you know, it's, it's so much more empowering today, practice regardless of that business, but like, it's so much more empowering today to get information, do all these things. My father was a coach in the '70s, you know, and so to be, uh, to put up your shingle, so to speak, and do all these things. Like, and so I think about that sometimes. It's just like people that just, they just need to be true. Like, they, they all wish they had like basically an executive assistant or administrative assistant, and they, they don't, and they're not going to have one, right? Because it's, it's prohibitively expensive. So instead we just give them like a front office, a back office, an ability to manage their stuff. Like, we just launched coupons, like maybe today, you know. So it's like various different things that are just going to help them do their work. And I, I just found that super empowering because then when we onboard someone, which we do daily, uh, it— you could see that it makes a difference for people. And that's just like, that's the reason to be able to do something and work so hard, is because you're— at the end of the day, you're going to help a lot of people. You're either going to help one person a lot, or you're going to help a lot of people just a little bit. This case, it's a lot of people, a little bit. And we believe that we can eventually— like, there's, there's so many solopreneurs out there. We believe we could serve like a lot of them.

Yeah, I love it. It's so great. It's very, and it's very empowering. I could totally see that. So if I think about you sitting there one day with Katarina thinking about building, uh, Breather as now compared to you sitting there with your— I remember his name, the former— who's your co-founder now?

Ben Neville.

Ben, Ben. You're sitting there with Ben and you think about building Practice. What's different? Like, what I mean by that is, you know, I had, I had Chris Shu, um, on the podcast who had been a big company guy for a long time, and he literally said in his first few months, he's like, what am I supposed to do? Like, how do I even get paid? How do I get paid around here? Like, he didn't know the basics of the mechanics. What do you know now in starting practice that you didn't know in starting Breather?

Well, the first— I will say the first thing that I really know with confidence is that I know how to be a CEO and a founder today, whereas then I definitely did not. And it's one of the— one of the points of leverage that you have if you're either pretty networked with other founders, which I was not at the time, but I definitely am now, I— it's just like, you're like, oh, like, how do you do this? Uh, it's a reason that investors can take rando shots on goal, because there's like a process. Like, it, it isn't— it's not painting a painting. It's not like pure, like, raw color and creativity, right? It's— there is— you're doing something and you're doing it in a, in, in a way that where you understand what you're going to do. And I would say there's a few factors that are really meaningful here, which are pretty standard. I was like, one is you want a market that you care about and that you work on for a long time and it's growing. And so it, it, coaching, you wouldn't think so. And maybe, maybe you know this, right? Because you've been doing it for a long time. Your coaching is actually a, it's a very fast growing industry. It's not really known well by a lot of people, but it's, it's growing really fast. And you especially see that in Silicon Valley, where like suddenly everybody else has an exec coach, but 10 years ago they definitely did not.

I can confirm, I can confirm that's true.

Yeah. Yes. Next to what you just said. It used to be a dirty word even, right? It'd be like, oh my God, someone is helping you? Ugh, that's disgusting. Now it's, it's sort of an understood thing. So, uh, and then another one is the quality of the team. And so there's, there's something about culture, and I, I got it abstractly then, but I will say that, that, that culture is so, so, so, so, so valuable in the business because fundamentally you're never going to be in all the conversations. And so even if you were a perfect decision maker, which Lord knows I'm not, I'm not, nobody is, Even then, you would not be in every conversation, and so you could not solve every problem. So, A, the people had better be good enough and hardworking and to care, but also they'd better be self-directed enough and sort of told, so to speak, how we behave here, what we do here. Just like everybody else, I'm reading the No Rules Rules Netflix book, right? And the thing that's fascinating about it is, is, uh, is how rude people are with their feedback at Netflix according to these stories. But inside of Netflix, it's considered very positive and really helpful because it's helping people succeed at the thing that they want to succeed at, and there's like basically helping them course correct, etc.

Et cetera.

But that's not what happens in most places. What happens in most places is people are quietly watching someone else fail. Oh my God, he's bombing. Oh my God. So, so culture drives so much more than, uh, than I— and it's so much more powerful. An example, uh, we, we hire at Practice, we hire internationally deliberately on purpose to create and increase diversity. It's one of the reasons one of our sort of things that we really care about. In 18 people, there are 7, I think, or 8 different native languages. And so we have people that are primarily Portuguese speakers, probably people are primarily Spanish speakers, people are primarily, uh, fucking German speakers, I believe. And so it just goes on and on and on like this, right? And so, uh, so Culture ideally brings people together with common purpose and means that people will make decisions correctly in the absence of someone who has a great deal of understanding of nuance, right?

Yes. Yeah.

And so it's, it, I, I will say, uh, people are, if you're getting, gonna get to product market fit, then once you, you are there, then quality of people is the most valuable thing, and the culture is alongside it the most valuable thing. Yeah. And, and you cannot, you cannot overestimate them because if they're broken, holy shit, are they broken? And there's nothing you can do.

So true. I love it. It's so true. So I'm gonna double-click, I'm gonna ask you to double-click a, a little bit and actually a lot on culture, cuz I feel like I found an important vein here from somebody who really knows. When you say culture, maybe be more clear what you mean. And can you clarify specifically the culture you're trying to build at Practice?

So we're actually building this document like right now. And so one of the main things that we allow people to do is we give people tremendous autonomy, which comes from the fact that we're a remote company. And so by definition, we're working in all kinds of different time zones, et cetera. We're meeting for the first time in June in person, and it's gonna be like, whoa, this is weird. But we have been building stuff together for, in some case, like single-digit years. And we have a super kind of— the expression I'm looking for, I think— my first language is French, so I think the word I'm looking for is collegial. What I mean is informal. Atmosphere, despite the fact that we've never had a beer together or what have you. Like, we're super, like, jokey and, like, and, like, kind of make fun of one another and all these other things, right? What culture is really doing is it's trying to stand for something. And what it does, in addition to kind of additionally guiding, is it alienates some people, probably, and it, it also makes other people that, that counter of those more loyal. And so it is intended to repel and to attract. And if it does those things correctly and it's guiding people in certain directions, then culture is succeeding. And so back to what we do and what we care about, we have a, we have a value that is called Be Self-Driving. And the objective— and culture is not like sacred, things change over time But the way we think about that is a car that self-orients, right? And that finds its way to the end on its own. It's not because we don't work in teams, we do, but we want to give someone the— empower them to be able to completely just be like, yeah, I'm going to figure it out on my own. I don't need to ask for permission. And so that would be certainly isolating to someone who had never done that before, was uncomfortable. It's a lot of people would be uncomfortable with that. But at the same time, it would take someone who does care about that and be like, fuck yeah. So it's an example of how culture can help people feel like, I really belong here, right? Another thing we do is every person we onboard, we bring an engineer into the onboarding. And so there's no one in my business that does not talk to customers on a daily or weekly basis, like literally nobody. And so, there's things like that that we really like. That might isolate some people and be like, "It's not for me." But for us, it means that every engineer understands who our customers are.

So, how do those things sort of self-drive? What I heard you say in totality is self-driving, kind of customer, super customer-focused, maybe customer-obsessed, customer-loving, I would even say. And then also, obviously, you're voting with your feet, diversity is important. In this way. So how does that accrue value to the business specifically, and how do you think it allows people to make decisions when you or your co-founder are not in the room?

Uh, well, fundamentally, when we talk about something like autonomy, it on its own is fundamentally about us being able— not being in the room and decisions getting made, right? Another thing that we try and do is we can try to give people lanes of work So it's just like, this is your project from start to end. It increases the accountability really meaningfully, right? Like, one of the things that I deliberately try to do at my company is I don't give people multiple KPIs. I give them one. And so that way it's exceptionally clear that this is what they have to do, right? And for me, I feel the same way about the work that I do. But at the same time, how they achieve it, so long as they achieve it ethically, is really not up to me. Like, like, you're smart, like, figure it out. And that's what smart people want to do. Smart people absolutely do not want to be told what to do. In fact, they actively resent it. And I would say even probably I resent it, and probably my co-founder resents that, and so do other people in my business. And so we all work kind of autonomously together as independent agents almost, right?

Yeah. I love it. I think that, you know, it also goes back to what you said earlier about hiring people. So, like, actually, many and maybe most people can't figure it out, don't want to figure it out. So, you have to— you're forced to hire people who can and want to and choose to figure it out. So, that's where you have the attract and repel, like, distinction in your culture.

Yeah, that's it. It should definitely— when you show people what you are about with the— I think I, I, again, this is practically like startup religion sort of at this point. It's just like, if it does not actively repel some people, it doesn't really stand for anything, right? And so like, obviously, because we're super remote, like, I have— like, I am super happy to be on Zoom calls X number of hours per day I do it all the time. Uh, and with that said, if someone says to me, you have to be in a— by the way, I, I was a CEO in an in-person office company for 6 or whatever years, right? I, I would, I would never do it again. And so, and, and so we— when I'll interview people, it'd be like, so, office? And if they're like, yeah, I was thinking, like, you know, throughout COVID you would do this, I would be interviewing interviewing people randomly. It'd be like, yeah, I think I might want to go back to an office. Be like, peace, see you later, right? You just want to build a company that you yourself want to be at. I, I definitely, because I was a first-time founder building a thing that was scaling like crazy, and it was like, like, where it's deeply, um, over my head for sure, and learning as I was going, um, was I, I made many, many more sacrifices than I probably should have. And I was like, oh, but I'll do it because I have to. What, what someone should do, again, when you— once you've gone past product-market fit, is find the zone where you're excellent. And if like you're miserable doing like this thing, like just don't do it and find a way to hire around it, or find a way to turn it into software or something, right?

Well, that's part of the emotional overwhelm, right? That it sounds like you, you did a whole bunch of stuff that just wasn't your highest and best use and then didn't, didn't do what you had to do to delegate it away or automate it or whatever. And that can be very taxing. And it sounds like you've learned that you're determined to not do it that way at practice.

Yeah, I'm just very clear about the type of, uh, the time I want to spend on this earth and how I want to spend it. In fact, I made a boundaries document for myself. And I, I put it into a file. And when I started this company, Practice, that I run today, I wrote a— I was like, here are my boundaries. And at the time, COVID did not— was not a thing. And I wrote, but I was like, I have to be remote at least a big portion of the time. Here are the things. No, no, no, no, no.

Well, wait, what are they? What are they?

Uh, off the top of my head, a lot of it was like If you don't like the people that you work with, like, just don't do this. Like, it's not worthwhile. And so a very clear— that's it, their boundaries document. There's a boundaries doc that specifically was like— I think it even is written in it, it's like, life is too short for this bullshit. And so ideally, culture is bringing a set of people like that together that feel that way. Ostensibly, someone smart, let's say, that could be convinced of an argument, they're like, "I feel ambivalent about it." You bring them into your company, they could definitely be like, "You know what? I learned to like this. It wasn't what I thought it would be, but..." But you can't find people that are the opposite and try to convince them. The job, we're going full circle on the thing that we're talking about, is really to find the tribe of people that you want to spend time with. Because everyone's going in all kinds of directions, you're not going to be able to have a really big impact. I think that's what a lot of people are really looking for. They're looking to— ideally, they're going to earn a good living, they're going to be able to support their families and all these other things, but they're also going to be able to have a really big impact on people that they care about.

Definitely. Absolutely. So you mentioned, uh, something about Netflix, and it's true that you talked about the that some of what they say to each other can certainly show up as rude. But they have a high feedback culture. That's for sure. So I'm curious about you. How do you make sure that you are getting feedback and that you're getting it from the right people? And what's an example of feedback that you got in your career as CEO at Breather or now recently that you didn't like, but then you digested and then realized it was helpful?

I will say that one of the ways that I do it now is I will start my one-on-ones, be like, hey, have any feedback for me? Like, I've just started with someone that began 2 months ago. We've done it, and I have conversations with them. And, uh, because you're not going to get that kind of high feedback culture unless you are able to receive it yourself, right? And, uh, between me and my co-founder, we have a lot of And I will say it's one of the great qualities of the co-founder relationship that I really have and I treasure. And I've told Ben many times, I— and he's told me as well, gratefully. And so it's mutual. It was like I told him, but he said nothing.

He's been silent on that.

Strange. We're very, very good. It'd be like, you need to hear this. And if you can't develop that in a co-founder relationship, then it's definitely not going to happen in the business.

But how do you get feedback from folks who are not your co-founder? Because that is a very difficult thing. CEOs and leaders have trouble with that anyway. Founder CEOs particularly have a lot of trouble having people tell 'em the truth. And I'm curious how you really kind of get that out of people and if there was something that you heard in your past that was kind of upsetting to you, but you realized it was actually helpful.

I can't think of a specific thing I was told, but I will tell you of a quality that I've absolutely had to mitigate. And it's just that I used to be direct and probably just like straight up rude to people, probably. And it's— in fact, I don't think that a ton of people from other places I've worked at would think that, but certainly some would. They'd be like, yo. And in fact, I will say that I practically accepted that quality because I wanted to be told direct rude things, right? And be like, come on, like, give it to me. But in fact, to be able to do it with an attitude of improving one another and improving each other's work is— the Netflix book gets it right— it— with positive intent is the language that they use, uh, is super, super, super important. I was interviewing Mark McLeod, who's a CEO coach as well, And he was the first CFO or practically CFO at Shopify back in the day. And from Tobi, who is the CEO and co-founder at Shopify, he was told, if you are the CEO of a business that is fast growing, you have to grow faster than the business. If you are growing slower than the business, you will get fired or you will burn out or whatever. Right? And so I— the faster we're growing the business, the harder that becomes. And probably the only way to do it is to get super transparent feedback. So I keep working on it. Like, I should probably have a framework every week where I was like, any feedback for me? Any feedback for me? But I will say that we do really have it in my co-founder relationship. And we're like— it's funny, kind of a funny thing to say about yourself because I I'll say I definitely didn't start that way, but, uh, but there's a— there's an emotional maturity that, uh, that we have, which is like, okay, like, you need to hear this. Be like, I can see that you're resisting this. Why are you resisting it? And, and so an ability to almost like have meta conversations on top of what's going on and be like, when you said this thing in this meeting that detracted from your objective. Instead, may I suggest you do this and this thing? And to be very clear about those things as much as possible.

Yeah. Well, by the way, those are good also, what you're talking about is coaching conversations, like meta, like the meta discussions are like, aha. So my observation is you seem to be resistant to what we're talking about, and I'm curious about that, right?

That's true.

Did you— so many questions about this, but like, did you have that same relationship with your, with your first co-founder at Breather? Katerina.

I developed it as a result of that. And so Katerina and I had been friends since childhood. Yeah, but we didn't have that type of relationship, and I didn't have the maturity to know that that was even something that I needed. In fact, the reason that I started the business with Ben versus someone else is because it's a relationship that I had with Ben, and that I don't— and actually, I, I had a choice. Like, I definitely could have started a business by myself, I definitely could have raised venture by myself, and I definitely could have even probably built a decent team and so on. But for the emotional labor reason that I had mentioned earlier, and also because of that emotionally mature relationship that I really had with Ben that I developed— and I don't think I could have developed it with just any random person. I think it required that we both be of this similar state of mind. And now we— I seek to do that with others. And one of the things that we— one of the pieces of language that we use for this is, uh, It's not like, "Can I give you some feedback?" but, "Is now a good time to give you some feedback?" The feedback is coming, but you can choose when you want to receive it. Is now a good time? And to be able to, if the person is like, "Really, no. Like, really, it's really not a good time. In fact, no." Sometimes it'd be like, "Just give it to me. Like, what do you got? Like, you know, just tell me." I, to, to, to, you know, it's interesting because in my relationship we do this thing where we talk about, we do a weekly, uh, State of the Union. It comes from John Gottman. Yeah, with my fiancé.

Okay.

Yeah, yeah. I, and so we do a John Gottman exercise which is called the State of the Union meeting, and we do it every week. I've told, I've told some people this and they're like, that sounds really intense. It is not a light exercise. But to every week, spend under an hour. The way that it works is one person does it one week, the other person does it the other week. And it'd be like, so here's this thing that you did that bothered me, or here's this thing that I want, or here's this thing that matters to me, blah blah blah. And the one person's job is to be able to be, uh, considerate while saying something the other person isn't going to like. The listener's job is to listen and to be empathetic and to be non-defensive. And non-defensiveness is really the core of what you're really trying to do here. And I think I— did I do it with— hmm, I'm not sure if I did it first with Helen or whether I did it first with Ben. But they definitely seem— I think they've happened in sequence with one another, like within the same, let's say, year that I started doing— having these relationships with people. That kind of clarity is incredibly, uh, important. I suggest it to people. I don't think anyone I suggested to does this because it seems like such a labor, you know, to be able to have a weekly conversation with someone about the relationship. So here's what I wanted you to like. I'll tell you what it does do is it allows you to vent and it really gets you to be able to practice having conversations without flooding emotionally. And that is incredibly valuable.

So valuable. And also what I really love is that you do this with your romantic partner and with your business partner. You know, yeah, well, I, I'm with you. You know, in my book From Startup to Grownup, I have a whole chapter on co-founder relationships. And I started off by saying, when you have a co-founder, you have a marriage. And that is it. And I actually have a tool I call the co-founder prenup, which has you really think about a lot of things in advance, like what are our values? How do we handle conflict? What are we gonna do when disagree? What are our, what's our vision for this company? And it sounds like you and Ben probably are able to have those conversations, but also importantly, you know each other. So you've already built up a sense of what are your values? What are we trying to get and how do we disagree?

Yeah, I deliberately was like, I was like, I, I was like, I think I want to start another thing. I was like, I really would like to start it with you, right? And then we sat in front of a whiteboard, or a few whiteboards, and, uh, we were like, here's what I hate to do. Are you— can you do this? Because I really don't like doing this and I don't want to do it. Okay, well, I'm good at this part. I don't want you to be involved in this part. So the discussion was had, you know. And like an agreement, so to speak. It's not a contract, like it's just, you know, there. But I think it's valuable. Like, it's true, co-founders are in relationships for many, many, many years. So, and it's a legally binding agreement, so they had better have settled some things ahead of time.

Uh, Julian, just a few more questions. Um, what do you wish you had known earlier on your journey?

Well, I didn't— keep in mind I wrote books before I started companies, and I was, I was a good, like, author, right? But I, I, I guess I wish I knew that I— that it is possible to just, like, work hard and be really good at something, and you don't have to be destined for one thing. It's the same reason I kind of don't believe in, like, a soulmate, right? It's just like you you go and you work really hard at something, and then that's how, you know, all these things built out together. It's not like random. So similarly, I, you know, even though I grew up in the language of, um, The Artist's Way by Julia Cameron, a sort of famous book that's been out there for a while, it's, it's like you discover your interests and you go after your interests, and that can change over time. And it is possible to be a CEO in one decade and then a an author in another decade, and to be excellent at each one of those things. And so I think I would've been more deliberate versus, oh, I'm gonna find like what my destiny is. Like, I really wanna believe in destiny, but actually it's just like, you can go out there and with effort I create something. I think it's much more about creation.

Creation than destiny. Yeah, that's great. And what advice do you have for other founders as they embark on their own journey to grow into leaders?

Yeah, make sure that you really love the thing you're going after. I— there is a really hard lesson about whether you should give up on something or whether you should stick. I don't have an answer for that. I've made that decision wrong before, right? Uh, but at the same time one of the nice things about kind of like the internet a little bit is there's always going to be another shot, right? And I, I think that if you're a repeat founder, like, you kind of know this. You're like— I, and I, I did at Breather, I really believed, like, my God, I came up with this really good idea and it was working and that's amazing. And it worked. I was like, it's still working. I was like, holy shit. And I acknowledge that it was rare that you have a first-time venture-backed business and it gets to that size. But at my mind— in my mind, again, I thought, oh, this is the one time I'm ever going to get this. I'm never going to be able to get this level. It's actually not the case. So one of the, one of the founders I— one of the things founders I need to hear is, uh, there's going to be another one. Like, don't worry, there's going to be another one, and you're going to be better like them, which maybe would give people more comfort to give up on something that needs to be given up on.

Yes, there's always another one. I love it. So good. Julian, what can I tell you? You're so full of life and wisdom and passion. I loved our conversation.

It was so nice. Thank you. I appreciate that.

Thank you. Thank you for joining me today. And I just want you to know that the people will get a lot of value out of this. So thank you very much. For your time today.

It was my pleasure. I had a great time.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.