There’s an argument to be made that Julien Smith, Founder and CEO of Practice, was born to be a career coach. But beyond that, the New York Times best-selling author has also done the hard work of founding his own companies and sharing his knowledge with other founders. Today, Faith talks with him about his journey, his body of work, and what makes someone a great leader.
(THE FRONTIER THEME PLAYS AND FADES OUT)
Hello. I even put on my fancy camera.
Ooh, it looks great. (Julien: Yeah.) I was totally shown up last week. Somebody joined with like, it looks like a NASA camera, (Julien: <Laugh>.) just like, the level of detail. (Julien: Yeah.) I was like, I’m rolling with like, the MacBook Air camera, so…
You don’t wanna see your own pores. I’m at that age (Faith: <Laugh>.) where I don’t wanna see my own pores, right?
You know, it keeps us humble, so…
Yeah, yeah, yeah. Well, but I have one of these <emphasis> guys, ‘cause I know you care a lot about the audio, which is great. And so we are joined by a preamp and a, I think a Sennheiser, or something.
Oh my gosh. (Julien: Yeah, yeah, yeah.) These are words…I don’t know. But they, it sounds like <inaudible>.
They are words. They’re words <laugh>.
<Laugh>. Julien, I’m so excited to meet you. This is gonna be really fun. Your bio is ridiculous, (Julien: Oh yeah? <Laugh>.) so I’m just gonna run down the gamut <laugh>.
It doesn’t feel ridiculous over here. So, yeah. Thank you for that.
Ridiculous, in a good way. (Julien: Yeah, yeah.) You know, there’s several uses in that term, and I just wanna clarify, it’s the positive way.
Well, sweet. Let’s get into it. We’ve got Julien Smith today, and Julien, today you are the CEO at Practice. You are also a New York Times bestselling author, which we’re gonna talk about today. And you’re based in Montreal?
That’s right. Yes, I am.
We’ve had several Canadian, like probably a higher than average ratio of Canadians to Americans on this podcast, so everyone will thank you for boosting those numbers. So Julien, you’ve helped to start many companies, including Breather, (Julien: Mm-hmm <affirmative>.) which you raised $150 million through a Series D before handing it over to a hired CEO. (Julien: Mm-hmm <affirmative>.) You’ve also coached other CEOs, (Julien: That’s right.) and so you’ve seen a lot on the ground, and I’m excited to get into some of those stories today. Those founders have been folks who have been funded by the world’s best venture firms, (Julien: Mm-hmm <affirmative>.) so again, I imagine those stories are very fun. But today, you’re at Practice and Practice is a client management software for professional coaching.
Yeah. I also manage like, all kinds of different like, solopreneurs. So like, you know, photographers, doulas, like, small business owners, businesses of one. (Faith: Yes.) We started with coaches. That’s true.
Your marketing site, I feel like is a masterclass in a marketing site homepage, so I’m gonna add that to your bio as well. What did I miss? Where do we need to fill in?
That’s good. I will say that the context comes from like, I didn’t, you know, I was watching like, a panel on outsider artists yesterday.
Hmm, what’s that?
Outsider means, over there, it means “didn’t get a master’s degree in fine arts”, probably. So that’s what that means to them. Here, “outsider” means, in tech…I think I consider all freelancers, and I really started in a freelancer type of world. In tech, what it means is like, “didn’t grow up in and go to Stanford”, “doesn’t have an engineering degree”. Like, lots of different kind of things like that. I’m definitely the outsider of outsiders, and so I started my…my father was a career coach, (Faith: Mmm <affirmative>.) and so I grew up in that space, and freelancing was how my father made a living, sort of, right? Like, on a contract-by-contract basis. And so I was very close to the coaching world very early. And that resulted in, I think, a great deal of empathy for kind of like, that person who’s getting started on their own.
And so Breather, which was a commercial real estate tech company that grew to 10 cities and hundreds and hundreds of buildings, and that allowed anyone to unlock a space with their phone and use it principally as a meeting room, is how it’s mostly used. (Faith: Cool.) My first customers were coaches, and people hosting pop-up shops, and all these different things. And it grew to 10 cities, hundreds of buildings where people could unlock the space with their phone. It was a very powerful kind of thing to be able to help so many people that are getting started and that didn’t have the infrastructure, right? And so Practice just tries to do that. We help businesses, mostly businesses of one, today, build the infrastructure so that they don’t have to think about it. So I’m a coach only to a few CEOs at any given time, a few founders at any given time, and I do it for a maximum of five clients. And so it kind of puts my freelancing business on autopilot, which is great, (Faith: Mmm <affirmative>.) right? And so if people don’t know how to do it, I’m really fascinated by the person who’s just getting started, who’s like, you know, starting like, a dog training business or who’s like mowing lawns for a living or something, (Faith: Mm-hmm <affirmative>.) and being able to serve them at the closest possible place to where they just had the idea. I love that.
And it’s such a, when you’re in that phase, you’re learning something new, you’re starting something new. And to also pick up a new software to help you manage that business is often a huge lift for folks who are in that space, and so I think that that speaks a lot to just the UX <laugh>, right?
Yeah. It takes a lot of work, you know, to make things simple, precisely for that reason. And I always think about, because we began with coaches, even though we’re past that today, coaches are often, it’s their second career as well, right? (Faith: Right.) So what that means is, is that they’re probably older, they’re middle-aged or older, and I will never forget, like, one of my first customers that was a total stranger, and they came in like, during like, a November or December where I was like, “Where is this random person coming from?” And his first name is David, and he was in New Zealand, and he’s still a customer today. And David was like, 75, I feel like, (Faith: <Laugh>.) and I was like, “Wow, this is amazing.” So it just, I’m so dedicated to this craft of like, trying to make things really simple for people (Faith: Yeah.) and making them really intuitive. And so, I guess, the two really connect to one another.
Right, and I hadn’t thought about how your work at Breather and your work at practice were really, the foundation was the same, right? (Julien: Yeah.) Which is just like, creating infrastructure for the same user group that often, frankly, is ignored in technical solutions, because they’re businesses of one. And so you’ve gotta be super committed to that user group.
That’s totally right.
So last year, I hired my first ever executive coach, and (Julien: Okay. Mm-hmm <affirmative>.) she totally changed the way that I thought about leading, and managing, and my own professional development. (Julien: Mm-hmm <affirmative>.) It was incredible, and now I recommend it to everybody that I talk to, but I think, especially for CEOs, there’s a lot of pressure to just already know.
I totally agree.
Right? To like, be born knowing how to CEO, which is ridiculous.
Yeah <laugh>. Yeah.
And so I’d love to hear your take. When is it time for a CEO to pursue an executive coach?
I had an executive coach before I was ever a CEO, and my executive coach helped me transition. I wrote a book, Flinch, in 2011, which remains popular today. I’m really fortunate to be able to say that, and actually, that I’m just seeing the first printed edition, ‘cause it was Kindle for a really long time. (Faith: Oh wow.) I’m seeing the first print edition today, so I’m very excited! (Faith: Oh my gosh! Congratulations!) I’m going there like, yeah, thank you. It’s gonna be great. And so I wrote that book, and I remember feeling like I had more in me that I could get out, (Faith: Mmm <affirmative>.) and at the time, I had met an executive coach in like, a Silicon Valley type of environment. I was like, “Oh,” and I knew what that was, and this was 2010, 2011, or something, (Faith: Mm-hmm <affirmative>.) and I was like, “I know what this is.”.
And that was, I must have been 30 or something at that time, and so I did this early, and I had the means to do it, ‘cause I’d had some successful tech businesses early. And I will say that, to have that mirror, even before I started the business, was helpful, (Faith: Mm-hmm <affirmative>.) because it helped me really crystallize what it is that I wanted to do, and it helped get that feedback. I think you’re totally right that a person is isolated when they are a CEO. They’re learning how to do the job. The people that I do it with are funded. They’re funded usually by a round of angel investment or more, going from, let’s say, as little as $2 or $3 million, when they started, all the way up to like $50 and more, (Faith: Mmm <affirmative>.) today. And it doesn’t really actually really matter what phase they’re in. (Faith: Right.)
They’re always isolated. They have to learn on the job, right? You have to be as <inaudible>, like, no one’s gonna teach you that. And maybe they try to teach you in an MBA, and they give you the fundamentals and tools, if you even do that, which most don’t. But even if you did it, it doesn’t teach you the real challenges, the “hard thing about hard things”, which is what Ben Horowitz would call it, (Faith: Mmm <affirmative>.) which is the psychology, like, “How do I remain motivated?” “Oh my god, I can’t sleep, because I didn’t, you know, this client turned out, and they’re not renewing, and that’s a huge deal for my business,” right? Or (Faith: Mm-hmm <affirmative>.) “The business is doing well, but someone is underperforming, but I kind of still believe in them. Like, what am I supposed to do?”
Like, that’s like a hundred different decisions at any given time that they’re making by themselves, and so it’s actually remarkable. There’s a few people that I know that have been CEOs and exec coaches, either at the same time or subsequent to one another. One is me and another one is Chad Dickerson, who was the first CTO at Etsy and then became CEO, and then made them public, and since then has become an executive coach. And he said that people really like that he was a CEO before. I think people like it that I was a CEO and am one, (Faith: Mm-hmm <affirmative>.) because it means that there’s a set of things that are tactical that I can confront, but it also means that I’m challenged by this idea of like, there’s a part of me that just wants to be like, “Well, here’s what you gotta do.” (Faith: <Laugh>.) I’m using my CEO voice. It’s “Here’s what you gotta do…” and actually, you should not do that, because you should base how you’re engaging with the person as they have all the tools they need to succeed, (Faith: Mmm <affirmative>.) and they have the intelligence to succeed, and they have the emotional intelligence to succeed, and you’re just sort of like, you’re like, like shoveling the snow so that the car can get out. You know?
Wow. That’s an interesting metaphor.
I just made it up, but it kind of works.
It’s good. I like the way your brain works. (Julien: <Laugh>.) Yeah, for me, it was really the first time in my career where I could talk through a problem with somebody (Julien: Mmm <affirmative>.) without worrying about how they were perceiving my ability.
Mmm <affirmative>, right. Ah.
Because when you’re in the context of a team, there’s always that dynamic, right, (Julien: Right.) whether you’re talking to somebody who manages you or someone who you manage, (Julien: Mm-hmm <affirmative>.) and even in the context of professional networks, right? Like, we maintain (Julien: I totally agree.) professional networks, because they’re supportive, but also it’s because that’s a pipeline, that’s a future pipeline (Julien: <Laugh>.) of employees or employers, you know? (Julien: Yeah. Mm-hmm <affirmative>.) And a coach was the first time that I was like, I don’t have to maintain any sort of posture with this person. I can just be kind of totally honest and lay it all out there and see, you know, get a mirror back. So it’s really magical. So…I don’t know. I think, when I think about timeline, like, when is it appropriate, I always say as soon as possible. (Julien: Mm-hmm <affirmative>.) Is there anybody in your book who’s not quite ready for it?
Certainly that’s the case. I think it’s more like, first of all, is it within the means of the business that you’re running or you, right? (Faith: Mmm <affirmative>.) And the second one is, is it the right person? Because one of the challenges that we face in coaching is that anyone can do it. You should, if you are getting a coach, maybe you care or you don’t, you know, some people who are CEOs know that I’ve been one, and they don’t care if I have any certification, or I’ve been through anything, right? (Faith: Mm-hmm <affirmative>.) But it would be nice if I had some principles behind what I was doing, beyond just shooting my mouth off as a CEO.
Right, right. Or “I read a book about it,” <laugh>.
Right? So I think it’s more like they will find, like, y’all will find one another. My coach is a guy called Ed Batista. He’s one of the oldest Silicon Valley coaches that there are. And I introduced Ed to someone recently in my network, and he was like, “Wow, what an incredible,” this guy is a surfer, “and he said, “Santa Cruz to Phoeno vibe,” which is like, laid back type of energy. And he was very excited to meet them, but he could have met my buddy, could have met like, 10, 15 other coaches and not felt that. (Faith: Mmm <affirmative>.) It has to feel good, and that’s actually maybe the job of the coach to make it feel good, (Faith: Right.) to be able to, we call it, you might call it like, “holding space” for the person. (Faith: Mmm <affirmative>.) But that lack of judgment is so important, because like, when are you, I don’t know about you, but like, you know, you hold a high standard for yourself. (Faith: Mm-hmm <affirmative>.) You’re out there in the world, as you said, your network could also be future clients or referrals. Like, you kind of want, you can’t help but kind of want them to think a certain way about you, and that purity of just holding space for someone, and they’re like, “I’m just here,” you know? (Faith: <Laugh>. Right.) Like, I just, I love that. There are times when I find myself doing a coaching call, and I’m cynical about it, and the reason I’m cynical about it is ’cause my father was a coach, (Faith: Yeah.) right? And I’m like, “This is bullshit.”
It’s like a part of me, but I also do the work, and I also kind of went through the cert, to a degree, and there’s other things, and there’s times where I’m on call, and I’m like, “Wow, this is really powerful,” and it’s not me. I’m just using like, a coaching tool that I learned, (Faith: Mmm <affirmative>.) right? And I love that I get to kind of like, be a witness to that. So I have this funny, nice experience where I get to work on something that is scalable, (Faith: Mm-hmm <affirmative>.) which is really exciting to be able to serve hundreds of people. Like, just today, 10, 20 customers came in. Isn’t that great? Right? (Faith: That’s awesome.) That’s really exciting. (Faith: Yeah.) And at the same time I get to serve someone in a really deep way. A hundred percent of my time, during that hour, is dedicated to them.
Like, like that’s a great combo. (Faith: Mmm <affirmative>). So it feels that the energy needs to be right between the two people, and if that’s the case, you know, go find someone. It can feel like you don’t know anybody who has a coach, maybe, and you feel like it’s weird or it’s woowoo, and it can be woowoo, (Faith: Mm-hmm <affirmative>.) you know, but it’s, I dunno. I’m happy that it’s growing, (Faith: Mm-hmm <affirmative>.) and when I had a coach in 2011, when I started, not many people did, and now there’s this explosion in Silicon Valley of tech coaches, it’s like a known thing. And so I like that, and I think that it should grow further.
Agreed. Cosign on that <laugh>. It’s kind of like therapy, where when you’re approaching your session, and you’re like, “Well, I don’t really have anything to talk about. Do I really need a coach?” (Julien: Yeah.) I always tell folks like, (Julien: Mm-hmm <affirmative>.) you will have something to talk about if it’s a good coach. (Julien: <Laugh>. Yeah. Mm-hmm <affirmative>.) Like, you’ll have something to talk about. Okay, Julien, your two other loves, (Julien: Mm-hmm <affirmative>.) building and leading companies and writing this book. Talk to me about the Venn diagram of those two things. Like, what’s similar when it comes to building a company and writing a book? What’s different? Like, talk to me about your experience.
So I wrote three books. I probably, at some point…
I didn’t realize you wrote three books.
Oh, okay. (Faith: Oh my god.) Yeah. I was like, more stating for the audience. Yeah, I’ve written a few, and I wrote some ebooks, as well. And it’s like I’ve been on the Internet for a long time, and what you have is, if you have the privilege of someone reading your work, which is nice. I actually just joined Substack, recently, ’cause I had an old blog from a very long time ago, and Substack has this weird network effect where yes, you’re just joining, and then all of a sudden, people follow you and you’re like, “Who the hell are you? And where did you come from?” But they just follow you. (Faith: Mm-hmm <affirmative>.) Isn’t that great? Okay. Awesome. Okay.
So there is this ability to influence people at a distance, and I believed at that time that my ability to influence people at a distance, like that’s what I liked, (Faith: Mmm <affirmative>.) and that I didn’t like the idea of influencing people directly. I felt that I was good on stage, because when you write people, when you write books and people read them, they invite you to do talks, right? So that was like, a part of what I did, but then I discovered I had the right idea, which was the idea for Breather that did take off and it really did take on a life of its own, and then I was forced to be directly influential, right? To be literally in front of a bunch of people that I employed and to be able to motivate them, which I hope I was able to be successful at sometimes. And so the idea forced me into a position to grow my capabilities that I didn’t think that I had.
I had certain boundaries, but I wanted, you know, back to this whole art thing that I was watching yesterday, the two artists were, ah <vocal exhale>, Woody di Othello, an artist from Oakland who does these really cool works, and another one was a Canadian artist called, these two, they’re like 25, Tau Mills, I wanna say, who’s another successful artist, and they were talking about how, being able to be at a place where they could engage and assistance, which is really hard for an artist to do, right? And I never really understood, you know, you look at successful artists, and you know that they have assistance, and you’re like, “What the hell? Like, how does that work?” (Faith: Yeah.) It doesn’t really make sense, and what I realized, and they portrayed it very clearly by saying it’s when your ideas, there are too many of them for the amount of work that you can personally do.
Aha! Okay. And so I discovered that to influence people directly and to be able to take an active relationship with them, to work with them, to be, they’re your customer or you work with them, and they’re part of your team, those things are actually way higher leverage, (Faith: Mmm <affirmative>.) so I discovered that I like both. I guess I was challenged by the type of, the book that I’m seeing later today in the print version is a book called Flinch, and the book is really short, and it went super viral. And the challenge of the book, it’s super short, is you have a set of things you wanna do, why don’t you do them? (Faith: Mmm <affirmative>.) Right? It’s like, kind of a powerful idea, and it hit a lot of people, and it was spread really widely. It was one of the only books on Amazon that was perpetually free, because a mentor of mine, Seth Godin, who edited it, I think talked to like, Jeff Bezos or something.
This was a long time ago. This was like 10, 12 years ago. (Faith: “Art is free,” is what Seth says.) Yeah. And, but, yeah. And the intent, the idea, was the art should be free, right? So I was challenged, and I was like, “Well, fuck. I just wrote a book about challenging myself and, I don’t know, really, how to run a business.” And I was scared, and I was, you know, someone at the time, I remember sending an email to my buddy, Greg Eisenberg, being like, “I don’t know how to raise $200K.” (Faith: <Laugh>.) “Like, I don’t know how to do that. Like, I don’t have any friends with money.” I always love this idea of this thing called a “friends and family realm”. Like, (Faith: Right.) friends and family realm that, like, where are these friends that people have?
My friends don’t even, they won’t bring a bottle of wine to dinner. They’re not gonna give me $100,000.
Yes they do. They could listen to this. Don’t say that. (Faith: <Laugh>.) They would <emphasis> bring wine to dinner. But it’s the idea that it would be easy to raise a friends and family realm. Like, first of all, this was in 2012 that I was feeling this. In 2023, they would call that privileged, (Faith: Mm-hmm <affirmative> <laugh>.) right? And so…
We had the words then <laugh>.
Right? Yeah. I remember feeling very threatened, but I had just written a book saying, why don’t you do things that you say you want to do? (Mmm <affirmative>.) So I was forced to confront it, because I had just written that book, and people would be like, “Wow, this helped me,” you know? (Faith: Mm-hmm <affirmative>.) I was like, “Well, I should help myself.” (Faith: <Laugh>.) You know, there was this need to call myself out and to turn into the person that I guess I became.
Mmm <affirmative>. It sounds, as you were kind of talking about that experience, it sounds like less of a Venn diagram. Like, here’s two very separate things, and more like those experiences are kind of inextricable from each other, because one led to another, and it’s almost like, cyclical, in a way, it sounds.
Matt Mochary, who’s a famous, sort of, Silicon Valley CEO coach, wrote a book called The Great CEO Within. It was like, a Google doc for a while that people spread around, and then eventually it became a book, and in that book, he calls the space is called like, the “zone of genius”. (Faith: Mmm <affirmative>.) And I challenge my clients, and I try to find when I’m like, you know, interviewing someone or something about like, what their “zone of genius” is. I think ultimately there’s just lots of different ways in which I’ve been able to take ideas that are maybe somewhat complicated and translate them into something that people believe. (Faith: Mmm <affirmative>.) Like, that’s like a skill, I guess, that I didn’t really realize that I had, but that I’ve done enough times, that I have been able to prove to myself that it’s not a fluke. (Faith: Mm-hmm <affirmative>.)
And so, if that’s the zone of genius, and if, not to say I’m a genius, but more like, where am I best? That’s the real question. Where am I best? And if that’s the case, then you should apply it in the highest leverage places where you can, (Faith: Mmm <affirmative.) right? Not like, limit yourself. And so I think that that was a part of it. Writing is very effective. You can leverage writing. And I was reading a book by Robert Chambers recently, came out in 1895, (Faith: <Laugh>.) of a funny situation where he published like, 50 sci-fi books, (Faith: Oh my gosh.) but he’s only remembered for one. And so like, he’s dead now, so he doesn’t care, right, (Faith: Yeah.) but like, thinking back on that career, and it’s just like, he wrote 50 sci-fi stories and only one of them is like, still in print, practically. That’s a crazy idea that you might do all this work and that only one thing might matter.
I think that’s kind of the challenge we all face. I mean, not to get too meta here, but it’s, you know, when we think about our careers, and what’s right, and where we should move next, it’s…inevitably, we think about what people will think when we’re gone, which is so silly, (Julien: Mm-hmm <affirmative>.) ‘cause what does it matter?
Yeah. How did you know that it was the right time for you to go the direction you went?
Right. It’s just, it’s intrinsic, I think. I look at decision making frameworks and, you know, everybody…scan medium, and it’s like, “Here’s how to make this major decision in your life,” (Julien: <Laugh>) and it’s like, well, it just comes down to your gut. (Julien: Mm-hmm <affirmative>.) Julien, building companies is very difficult, and it is not for everybody. I think often folks think if you’re an idea person, you’re just, you’re just waiting for the right idea to strike, and then anybody could build a company. But, while it’s true that anybody could, it’s not true that everybody delights in it. And I think if you do it more than once, you probably delight in it. So I’d love to hear your take on what are the best parts? What do you enjoy about that process?
Yeah, that’s a good question. Most of my friends who have been successful at raising a bunch of money, scaling a thing, a friend of mine that comes to mind at the moment is Michael Karn, who started Skillshare, right? Okay. (Faith: Mmm <affirmative>.) Skillshare, of YouTube fame. Why YouTube? Because they sponsor every YouTube video (Faith: <Laugh>.) And so he was like, “Why are you doing this again? Because you’re doing it, and it’s quite difficult, and it’s so much stress, and like, all these things. You would’ve been very easy to keep writing books, for example, versus like, figuring out how to raise money and hire people,” which I’d never really done, and all these other challenges. In my case, I was so compelled by the raw capabilities of the highest-value people that I worked with at Breather. (Faith: Mmm <affirmative>.) I was like, what happens when you hire…think at the height of it, there were like 250-something employees, like a fair good number.
It’s not like a, it’s not Netflix, but it’s like, it’s getting up there. So what happens is you’re like, oh my god. Like, some of these people are so unbelievably talented. I found that doing hard things was really challenging. It’s more challenging and more rewarding than writing a book, which often you feel like you’re writing kind of the same stuff again and again, (Faith: Mmm <affirmative>.) and that the level of complexity, it is challenging, by the way, to distill complex ideas into simple principles, and then write about them, and then write about them in a compelling way. Like, that’s a hard thing too. But there’s something about being able to, like, there are people that I have worked with that I would, I feel like today I would always work with. (Faith: Mmm <affirmative>.) I was just like, I’ve got to work with this person again in some capacity, because the talent is there. And what happens in venture, and what I mean is, is when people invest in companies, right? It’s like, it’s a place that Facebook and Airbnb came from, and Uber came from, and Google came from, (Faith: Mmm <affirmative>.) and Apple came from, actually, right? And so that way that people start companies creates a confluence of speed, and talent, (Faith: Mm-hmm <affirmative>.) and motivation.
And there’s not a lot of places, right? Like, if you were gonna take, if you turn it, if you look to nonprofits, you’re gonna get motivation, and you’re probably gonna get talent, but are you gonna get speed? No. (Faith: Mm-hmm <affirmative>.) So there’s not a lot of places where that happens, and tech happens so fast, (Faith: <Laugh>.) and so I don’t know. I just felt that it was one of the highest leverage places that I could be, (Faith: Mmm <affirmative>.) and that it’s back to this whole thing about like, you serve one person. If you’re gonna serve one person really deeply like, that’s super interesting, but also it is very compelling. Like, I think at the height of it, yeah, maybe like, millions of people have used Breather in big cities, and I find people that have had, that have been really meaningfully affected by it. It turned into like a brand, (Faith: Mm-hmm <affirmative>.) and it happened kind of under my nose, because I’m in Canada, I don’t really pay that much attention to it. (Faith: Mm-hmm <affirmative>.) But in New York, in San Francisco, and Los Angeles, and London, like, all these people in knew about it. So the power and the speed at which that happened is just like, oh, wow. You know? (Faith: Right.) So it’s hard to do something else after that.
It is. And I think once you identify the space that gives you the most energy, the kind of work that gives you the most energy, that is such a huge unlock in our professional lives. I think, I mean, jobs are wrought with a lot of conflict, and, you know, it’s hard for most people, I would say, professionally, to allow themselves to think about like, “Well, what do I actually want? And what brings me energy?” (Julien: Mm-hmm <affirmative>.) “What do I enjoy working on?” Just because of our relationship with work, I find it really inspiring that the reason you keep building is because that’s just the space where you feel the most energy, and it sounds like where you do your best work. So…
From all of the people that you’ve spoken to, on podcast and off, what is the theme of those that have made it work? Like, what was…for me, I would just say, mine, I would say like, work ethic is just like, so important, just sticking. But when you talk to so many people, like what do you get? What is the principle, what are the principles that you get out of them?
Hmm. I honestly think there’s just one very clear, through line among all founders or folks who build things, which is they’re there to build, they’re not there to accomplish. (Julien: Got it.) And you think about folks who throw in the towel, or who do it once and they’re like, “That was not for me,” it’s because they were surprised by this environment where you thought it was gonna be a series of win after win after win, and you’d be able to celebrate those wins. And of course, you expect losses too, but the reality of founding a company and building something is, you kind of barely notice the wins, because you’re always thinking about the next thing. (Julien: <Laugh>.) You’re just, you are on the treadmill. (Julien: Yeah.) You’re not going for a run from point A to point B. Right. And you have to like being on the treadmill, and if you don’t, you’re, you’re not gonna come back and do it again.
Yeah. I agree with that. It’s one of the reasons that I always advise people that starting a company has gotta be in a wheelhouse of something you really care about, (Faith: Mmm <affirmative>.) and there’s probably not a lot of those, right? There’s probably not a lot of things that, your word “through-line”, I think, is very strong, that the number of through-lines in your life, what are there, like, five maybe? Right? (Faith: Mmm. Yeah.) Like, I can think of only a few things that I was excited about at the age of 10 that I’m still excited about 25 years later, (Faith: <Laugh>.) right? There’s not that many. So people change, et cetera, et cetera, et cetera, but also people stay the same. (Faith: Mm-hmm <affirmative>.) And so you go out to find places where you do that. There are other people like, people that come outta Y Combinator, I always, the example I always use is Jack Altman, who started Lattice. He started a company, and it made performance review software, and so I was like, I think he talked about it pretty openly. He was like, “I did not start excited about performance review software,” (Faith: <Laugh>.) right? (Faith: Yeah.) But, you know, he ultimately became excited about it. So there are people like that. (Faith: Right.)
And I think lots of freelancers, lots of businesses of one, they’re just like, “Well, I don’t fit into this space, and here are the things that I can’t do, and I can’t, this is just like…because my first books were really like, directed at freelancers, (Faith: Mmm <affirmative>.) right? Trust Agents was directed at freelancers, where it was like, “Here’s how to build an audience online, and here’s why that’s good.” And it was a lot of people that were, just did not fit inside the box that they had been presented with. And they’re just like, “No, no, no,” and they resisted it, and they had to go out, and they had to make their way.
Yeah. You talked a little bit about one of the great joys of building a company is just being able to work with incredible talent that knocks your socks off, and you’ve had a front row seat to several other companies as they’ve been built, across different industries. (Julien: Mm-hmm <affirmative>.) And our thing here is hiring, building teams, how people think about that, so I’m curious, what are the challenges that you’ve seen that have been similar, regardless of industry?
I will say that there, that the top people always have a certain set of qualities, and that I’ve become very principled about hiring. (Faith: Mmm <affirmative>.) Like I, you know, it just, it happens over time. Like, you have to fire a certain number of people to get to like, 300 people that you’ve hired, or whatever the number is that I’ve hired. (Faith: Right.) It’s more than that, but it’s like, you have to get, there’s a certain amount that’s not gonna work out. And so I remember doing it on instinct. There are several mistakes that happened, and one of them was just like, asking rando questions, (Faith: <Laugh>.) which I think everybody goes through that phase of like, “I’m just gonna ask stupid shit.”
Right. I’ll just know when I know.
“I’ll know when I know.” No, you won’t! (Faith: Yeah <laugh>.) You will not, and so it’s a question of “I’m gonna ask random questions, and I’ll know when I know.” Do not do that, for a lot of reasons. Second, one of the biggest mistakes is people do not source enough people. (Faith: Mmm <affirmative>.) It’s so common. “Here are the people that I know. I know like, three people, I’m gonna get three candidates. I’m gonna hire among them.” No! <Laugh>. Talk to like…one of the best, I mean, most highest performing clients that I have, (Faith: Yeah.) is he was like, “I want to…” was it a CFO? No. Maybe a Head of Finance, maybe something like that, like a VP of Finance, and they interviewed, not even the process of interviewing for candidates, but what we would call “informational interviewing”. (Faith: Mm-hmm <affirmative>.)
Right? Going to discover, so you could learn about the industry and what a good person is like. They interviewed 25 VP of Finances, (Faith: Wow.) just talking to them, and this person is very high-performing, by the way. (Faith: Mm-hmm <affirmative>.) And what happens is, is they just go the distance. Like, for example, right now, like, we have a bunch of reviews on a website, G2. Okay? Lots of people know that it’s this website, they review software on it, it’s like you can try like, a little bit and get some reviews, but you’re gonna get like, five. But like, our objective, internally, is we’re gonna get to a hundred, which is a lot. And it’s very difficult to do, because people have to go through this very onerous like, process to be able to put a review in to authenticate themselves, ’cause they have to be real people and all these other things. (Faith: Mm-hmm <affirmative>.)
So like, are you gonna be the type of person who’s gonna get 5, or are you gonna be the person that’s gonna get 100? (Faith: Mm-hmm <affirmative>.) And really, to be a top 1% or top 10% entrepreneur or a CEO or whatever, you gotta be the person who’s gonna talk to the 25 VP of Finances, before you even interview anyone, (Faith: Right.) and that is really challenging. You don’t always just need to do that with legwork. Sometimes you can hire a recruiter, but I always, whenever I have an executive now, that’s one of the biggest things that I say people is like, “Never hire an executive on your own.” (Faith: Mm-hmm <affirmative>.) Always hire the best possible recruiter, and then talk to five recruiting firms before you do it, right, so that you can get a gigantic source of people. The leverage of hiring the right person, which comes with a lot of pre-work, tons of it ultimately results in much less post-work. (Faith: Mm-hmm <affirmative>.)
The post-work is, is how much you have to support that executive or maybe replace them if it doesn’t go the right way. So instead of doing that and just putting the work off, why don’t you do it upfront, and then you’ve hired a great recruiting firm, or you’ve talked to 25 people, or you know exactly what the candidate is gonna look like. You know, like, all those things, those are much more effective uses of your time. It really is, ’cause the CEO’s job is actually ultimately a human job, right? You’re not writing code, you’re not, maybe you’re building product, but ultimately that gets outsourced as well. You’re not selling, even though you begin selling ultimately later on, you do not. And so it is ultimately a human job about managing and creating high-performance and high-empathy culture, where people want to stick around, and they want to do something really great of their own volition. You can’t make them do it. (Faith: Mm-hmm <affirmative>.) They have to be, they have to want to do it, and so that’s how you really get where you need to go, I think.
Right. It sounds like the key mistake you’d caution folks to avoid is not having a clear archetype of what good looks like, before you go out and hire.
Yeah, that makes a lot of sense to me, and that has to come from lots of information gathering without something in your mind ahead of time, (Faith: Mmm <affirmative>.) ’cause they often, the amazing part of it, finding talent fundamentally is also about finding talent that’s mispriced, right? (Faith: Interesting.) Like, the same way you would find a stock, right? (Faith: Yeah.) And you’re like, “Oh, it’s actually, I’m confident that it’s gonna be at a $100 one day, but I’m buying in here at $10.” And so what you wanna do is, you wanna find talent that is mispriced, (Faith: Mm-hmm <affirmative>.) because all the talent that is not mispriced, they’re at Facebook or at Google, or they’re working at, they’re making $500K a year at Salesforce or whatever, you know what I mean? Like, they’re like, if they’re not mispriced, they have been found (Faith: Mm-hmm <affirmative>.) So your job is to find the unfound thing, right? The needle in the haystack, so to speak. So not only do you have to find people that are affordable, but you have to find one that should not be affordable, (Faith: Mmm <affirmative>.) is but should not be. And when you find them, who’s one particular person I will not name, but it’s like, I convinced them to move from the Philippines. (Faith: <Laugh>.) They were actually Canadian, but they had moved to the Philippines. They were like, in the process of moving and I was like, “Stop!” (Faith: <Laugh>.)
And I did convince them to not move to the Philippians, and they worked, and they became a really high performing person in my previous company, (Faith: Mmm <affirmative>.) and so finding that mispriced, that asset is so, so, so, so important. One of the biggest things is just, how much energy do they bring? Right? (Faith: Yeah.) There’s a very good book about this called Hiring With Your Head that is almost like, checklist kind of hiring. There’s another type of book called, which is very famous in sort of tech, which is called Why, W-H-Y. Why. Oh, excuse me, no, it’s called, that’s wrong. It’s called Who. It’s called Who. (Faith: <Laugh>.) Not Why.
It’s one letter off.
Yeah, yeah. I was almost there. And so this book is about processes of hiring and things like that, but Hire With Your Head is the one that I really draw from. It’s written by recruiters, and the thing they really talk about is, if you do not have energy, you have a dud. That’s it. If you don’t feel it, and it’s especially true when you run a remote company, which I do today, if you don’t feel the energy through the Zoom call, right? Like today, Faith, like, right this moment, maybe not in minute one, but by now you feel my energy through the call. (Faith: Right. Right? And if you do not feel the energy through the call, there is none.
What a good litmus test, right? Because I think <laugh>, you mentioned at one point during this call, you know, part of the challenge, one of the many challenges of leading people is like, you know, who is, who’s underperforming, but we still believe in them. How do we gauge that? And energy is such a critical line on that rubric (Julien: Mm-hmm <affirmative>.) that I think we often overlook, particularly in remote companies. So…
I mean, how can, you know? Right? (Faith: Right.) You have no idea, <laugh>. It’s like, I could have another laptop here. I’m like, I’m going to my other job on the side after this one, so it’s like remote hiring is crazy. (Faith: Yeah.) But I really like, the thing that I really do like about it is, I like the idea that I can hire someone from anywhere, finding quote/unquote underpriced talent, mispriced talent is really about finding undiscovered gems that haven’t been given a shot yet. (Faith: Mmm <affirmative>.) And back to this whole thing of this independent spirit, Breather serving freelancers, Practice serving businesses of one, right? Like, I feel the same way about my teammates. I like, I want to give them their shot. I want to give them their ability to do the best work of their lives. Right? I want to give them that space. And so I try really hard to find people like them.
It’s hard work, and (Julien: Mm-hmm <affirmative>.) and good on you for believing in recruiters for that role. I think it takes, it took me a long time to be like, you know, I can trust somebody else with this, especially when it’s something you care so much about, and you truly believe like, “No, I know better than anybody who’s best for my team.” Taking that leap to…
I think having a recruiter is really just about seeing more people. (Faith: Mmm <affirmative>.) First of all, it’s very clear to me now that like, you should never, ever, ever just have three people there in your interview. (Faith: <Laugh>.) But the first time that you’re a CEO, and you hire a person, right? Like, this artist that we’ve spoke about that just hired their first assistant, they maybe thought, “Oh, I can interview three people.” (Faith: Mmm <affirmative>.) But that’s actually like, if you are a CEO, and you’ve done it enough, you actually know that that’s just straight up wrong and bad. (Faith: Mm-hmm <affirmative>.) By definition, just the more conversations you have, the more you get an understanding of what good is, (Faith: Mm-hmm <affirmative>.) because when you talk to three people, you’re like, “That’s the best, verses…this is the top of the three.”
Right. It’s a false choice.
Right. And so what you really want is you want the top of the 10, and actually the 10 were sourced and handed to you, after you had three hours of conversation with people. In my case, of course at this stage, it is easier. It’s not easy when you don’t have a network, but it was like, I went to Andreessen Horowitz, which is, I was not able to have invest for last company, but I was this time. It’s like, considered one of the best Silicon Valley kind of venture investors that exist. And they’re like, they have a recruiting arm. (Faith: Mm-hmm <affirmative>.) Okay, so great. Like, I need to meet a recruiting firm. They’re like, “Great, here are the five that we think that you should talk to.” (Faith: Amazing.) Focused on A, B, C, D, E. And then I had my own that I had known, and I spoke to entrepreneurs, and like, eight recruiting firms or something..
Now it’s like, talk to each of them, and once again, you’re interviewing them. What matters? Lots of different things, but once again, energy, like we just said. (Faith: Right.) So the person that ultimately got the deal and that hired a great candidate that has been in the business, I wanna say for eight months, today, now. (Faith: Mmm <affirmative>.) That person calls me, they’re like, “Hi, I at like, my daughter’s wedding,” not like that, (Faith: <Laugh>.) but like, something like that, “But I just need to get on the phone with you right now. I just wanna let you know I want this. We’re gonna work hard.” Right? And they’re quite tightly connected and like, early roles and things like that. So now you’re like, “Okay, great,” and now they, with the high energy, are gonna go out and find other high energy people. (Faith: Mm-hmm <affirmative>. Yeah.) Right? So it multiplies, right? It’s like a force multiplier on itself, or it degrades, (Faith: Mm-hmm <affirmative>.) and you just have to ensure that you get the force multipliers and stuff.
And, you know, like, attracts like, and so if you can, if you continuously add to your network or team, folks who are, you know, the standard for what you want your team to ultimately look like, that’s like you said, a force multiplier. So Julien, this has been such a fun conversation. I feel like I learned so much, and there are so many one-liners. (Julien: <Laugh>.) I can see how your books took off, because so many one-liners that I’m like, we need to put that on a t-shirt.
Tiktok. Yeah, for sure. So if folks wanna get in touch with you, learn more about you, learn more about Practice, (Julien: Yeah.) where should we send them?
Yeah, you can go to Practice.do. We serve all kinds of solopreneurs. Check us out. We do cool stuff, and we work hard, actually, so says G2 and Capterra, and all the other sites. And we do, ‘cause we care a lot. I have been working on a lot of stuff on the Internet over a long period of time. (THE FRONTIER THEME FADES IN) The book, Flinch, which has been out for a long time, and people read a lot, is coming out in print edition, and you can look it up. I think it should be probably pre-orderable on Amazon for the first time ever in print form in the next like, week or couple weeks, which will be very exciting. (Faith: Awesome.) And yeah, just out there reach out Twitter, Substack, whatever. Let’s chat. It’ll be great.
I’m gonna follow, I’ll recommend your Substack on my Substack, (Julien: <Laugh>.) and we’ll get this (Julien: Thank you.) referral engine running.
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