Julien Smith | How to Identify Opportunities for Innovation and Transformation

Srini: Julian, welcome to the unmistakable Creative. Thanks so much for taking the time to join us.

Srini: Well, it's funny you say that. 'Cause like my parents definitely they'd deny that they pushed us in any way. My dad's like, oh, we told you to do whatever you want to do. I was like, yeah, you told us we could be any kind of doctor, lawyer, or engineer we wanted to. But I will say this, like, you know, my, my old roommate, Matt, was like, oh, did you get straight As in high school? I was like, of course, I got straight As in high school. And I'm like, at my house, that was like a non-negotiable; you got straight As. But it's funny because what I realized now was that even though I thought that was ridiculous and a pain in the ass in high school if my parents implicitly taught us the value of intrinsic motivation, they didn't pay us for getting good grades. Like that's just what you do. And you know, that expectation of high achievement while it comes with certain pressures and can be pushed to a point of diminishing returns, I think to your point, there are definitely benefits.

Julien Smith: Yeah, I, you know, I just, you know, you always look back like, it's funny. Cause we have the deck of cards now that my fiancee got us for Christmas and it just has question cards. And we ask them over dinner and it's like, what would you tell your present, your, your version of yourself from 10 years ago that you've learned? And, so it's a lot of really reflective type of questions to me. I, I felt that I was given very much free rein, which allowed me to be an entrepreneur and allowed me to kind of try out a bunch of things. But I do wish there were several years when I was younger when I, I feel like looking back on it, I kind of wasted them. And I like it again, it turned out fine. But when I have peers of mine who are very successful, a buddy of mine, the founder of Code Academy, his name is Zach Sims. We chat all the time and he just sold his company for about 500 million bucks. And he's like 31. And I'm always like, wow, like, how does that even happen? And then you, if you look

Srini: I had another guy here. I think I remember his name. He wrote a book called 'Messy' and I can't remember his last name. His first name was Tim Hudd, but we were talking about D&D and he was a big D&D player.

And, you know, I'd asked him about misperceptions of people who play D&D. You know, I would not have connected amazing oratorical skills to somebody who played a lot of D&D because I think typically the stereotype is, oh, these are just geeks who sit around, you know, on their computers. So explain to me how that happens.

Like, what misperceptions do we have and how do you develop the skill of oratorical and great storytelling?

Julien Smith: From something like D&D? So what happens? So I'm 10 years old and I pick up, like, for some people that know the red box, the red box is like the first kind of really slick published Dungeons and Dragons box. And I mean, it's having a resurgence now hugely, right? Like all, I look at all these podcasts, both on Spotify and YouTube. And it's like, this thing is it PA is sponsored by D&D Beyond. I was like, man, look how far we've come. Do you know? So, so this is not a popular hobby when I'm [around] and I'm looking at it and I'm like, oh my God, this is so cool.

And I find friends that I'm actually friends that I still play with today. And, and you wouldn't, you know, it's so interesting. It's like, you might be thinking of certain things that your kid does. And you think of them as being let's say, wasted time. So I think that my parents probably saw it as wasted time I think about it now, but it taught me an enormous amount about improvisation because you bring a group of your peers

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Hey, it's Srini. So one of the things that makes it possible for us to make this show is by selling sponsorships to advertisers. And one thing that would be really helpful in terms of helping us get more sponsors that are relevant to you is if you tell us a little bit about yourself. You

Julien Smith: That's not surprising. Yeah, it, it and as I think about Ryan, if I remember correctly, he's constantly reading, constantly trying to absorb information. He's actually very naturally interested in history. And in, in examples of leadership or examples of stoicism or not. And so like, there's a kind of, I don't know, I I've come back to this view that I was in before the previous company that I ran, which I ran for quite some time, raised a whole bunch of money for and ran to about 150 or something employees called Breather, which I think probably some people that will listen to us have heard about--there's a fractional real estate technology startup that I started when I was about 33 or something.

Yeah. But when I was looking and saying, okay, well, what am I going to do now that I've finished working on this company, we'd hired an outside CEO, blah, blah, blah. I was like, I was like, well, it turns out you have to work on things and it takes a really long time to have an impact. You, when you were young, you really believe it was going to take two years or three years to

Srini: Let's go back to the beginning. I found out about you and connected with you initially because you were a writer and a blogger who had a wildly popular blog on the internet. I remember you wrote two books, three actually if I remember correctly. And then the last thing you did was "Flinch" with Seth Godin. I want to bring back a clip from our previous conversation and then talk to you about how you think when you're done with something. Take a listen.

Julien Smith: I followed trends in technology, and then I used those trends to create something interesting and new. And, or be a part of something interesting and

Srini: Now, and

Julien Smith: That usually ends up taking my career to a level it's never been at before. You're looking at this thing and going, "What is this going to really enable?" Like, what's different? You could never have predicted Uber by looking at the mobile phone, but GPS plus screens, plus all these other issues create this system, which was previously impossible. The way we at Breather think about that is we think about the same kind of platform, the same kind of tool that becomes available for physical space, which is basically created through electronic locks. So electronic locks are this thing that allows you to open up sort of a network of rooms with your phone, which is, to us, an incredibly exciting and revolutionary concept.

Srini: So, yeah, I've probably quoted that a thousand times, used it in presentations, used it to inform, you know, decisions, but, you know, so I want to talk about first when you decide that you're done with something and then let's get into that whole idea of looking at trends.

Julien Smith: Yeah. I mean, first of all, it's super interesting to listen to myself again from that viewpoint. And I think it's amazing that you're bringing it here so that. I, I view me, I don't know like I was very informed by this comic, what is called like Saturday Morning Breakfast Cereal maybe is what it's called and in, you know, how comics like randomly they'll have like funny things and I'm talking about a wiggle web. And they have funny things, but then every little while they'll come up with something very true. And, and I actually, I grew up on comics like Calvin and Hobbes and Bloom County and like a bunch of other comics from back in the day when you used to open your newspaper and, and there would be a whole page maybe there still is. I don't know. And, this one was that you can have, you tend to have a career every seven years. And I thought about this many times and this idea of you can. So first of all, that gives you like this, this really good perspective on your life, which is that you actually have a shot at doing many, many different things. It follows

Srini: Well, it's funny you say that because you know, I went through the whole book writing thing. I got my book deal largely because of the habit that you've taught me to develop and funny enough, you know, two, two books later, I mean, I wasn't, you know, Mark Manson, who was the person who basically capitalized on your idea. And I think after that, the entire publishing industry lost their minds and thought putting a fucking title on every book was the key to, you know, billion-dollar books, but we'll come back to that. But one thing that I thought about after reading two books, I thought, okay, well, we raised a round of venture funding. Where's the payoff going to be bigger? And where's the contribution? And I'm like, all right, if I, you know, get another six-figure book contract, that'll give me a windfall that lasts me two years. If we grow in the stackable, sell it, you know, provide a return to our investors that will set me up for life. So it's, you know, that thing 50 Cent and Robert Green talk about, long-term payoff versus immediate payoff. And really looking

Julien Smith: Yeah, I agree. And, and you're not, and most people in the book space aren't completely separate from the marketing space. They aren't distinct to a degree, but definitely, people in that world are not complacent by nature. They're more than. They're like, oh, I'll go here and there. And like, they have a lot of unfinished things that they do, but once you figure out, you're like, okay, I got to write this book. You're never going to hit a deadline, but regardless, like, I'm going to write this book, I'm going to publish it and it's going to go out. It's like I did something and it's on the shelf, you know? And so there's something about that even today. Like, I mean, I'm sure I know it happens to you. It's different than a company. I'm happy that my company had, you know, millions of people use Breather and I had a hopefully positive experience, mostly did. And I know a lot of people read the books that I wrote. I'm very proud of that, but it's like the book is on the shelf and there's something about that being on

Srini: Hmm. Well, I think to me, I think the way I think about it is I never want to be defined by any one thing for the rest of my life. Hmm.

Julien Smith: Yeah. I don't think I do either, but I suspect that probably. One thing that I end up doing will dwarf everything else. And actually, you know, to tell you the truth, even though hundreds of thousands of people have read that book, Flinch, that we were talking about a second ago. Even Trust Agents was a New York Times bestseller, et cetera, et cetera. By far, Breather was more successful just from that. I mean, obviously, from a revenue standpoint, that's true, but it was much more successful from a cultural impact standpoint. Then any of my books were, which is like, again, like, it's a funny thing to talk to you about, that we have a longer context. We have almost 15 years of context between one another. And the fact that you and I can talk about that arc, not a lot of people can do it. And, the only reason that I was able to switch from being a writer to being a CEO or a tech entrepreneur, in, a strict sense, is that you're venture-backed, and all those things are because I'm really good at coming up with ideas, but

Srini: From someone that's obviously a job you want either. It's like the most thankless job in the world - up until it's not, you know. One thing that is interesting, you talked about a "breather wharf" you know, everything else.

And there's a, I don't know if you remember Robby Con's podcast "How to Get Rich with Kevin Blocky", which is literally probably the podcast where he talked about Sam Altman, who said, you know, basically he wants whatever he does next to make whatever he did previously look like a footnote in his career.

And that always stayed with me. And to your point, like I know for a fact I'm a far better interviewer than I am a writer. And I know this based on the numbers - far more people listen to our podcasts than read my writing.

Julien Smith: So, I'm not sure if this is the right place to ask, but does anyone know how to fix typos?

Srini: One other thing that you said you were talking about coming up with ideas—there's something you said in our previous conversation that I pulled out, and I thought was really interesting—and I wanted to do a deeper dive into it.

Julien Smith: Technology is a series of Jenga blocks that build on top of each other. And each Jenga block is necessary for the next Jenga block to exist, but we can't predict what will happen ahead of time, but we always have to be saying, "Oh, here's this new tool. What does this new tool allow me to do over and over and over again?"

Srini: That has always stayed with me because I think ever since that conversation, every time I see a new app, or new tool, my default question is not, how do I use this to grow my audience? It's always, how can I make something that I couldn't before using this? And it was largely to do, like, I look at every new piece of technology. I'm like, yeah, that's my default question, okay, what can I make using this? But speaking of Jenga blocks, I, this was the example I used in a talk I gave to business school based on this conversation, you know, and I, of course, cited Breather as an example of how you have like these intersections of different technologies and how, you know, basically in the early nineties you had the combination of the intersection of the commercial web browser, the ability to process credit cards, which was a contribution of the porn industry - if, for people who don't know that - and then, you know, e-commerce as we know it is borne by the intersection of those two technologies. Then, you fast forward to like web 2.0, and then you get to, you know, mobile devices, like you

Julien Smith: Alright, so it's very challenging. This is a super long subject, but it's a subject that I'm super fascinated with because I've started a number of companies and, because I was first in the forefront of a number of technologies, podcasting is one of them, as you know, 'cause you were there too. Right. And so, what happens is that I think about it and I'm sort of riffing a bit in terms of the way that I talk about it is that there are meaningful changes in value as a result of often important cultural changes, an important technological change, or vice versa. And actually, Ray Dalio has a book, Principles, of what's the recent...

Srini: One that we're just changing the world. Yeah

Julien Smith: Yeah. Literally had the principal on my desk. Yeah, yeah. Yeah. I didn't know my audiobooks, so I same. Yeah. So that book will give you some sort of global ways that major changes could occur. But if you think back on things that could happen and what happens in these spaces, is that actually there's a number of companies that could be started and transformations that occur in every industry. And so we were talking a moment ago about electronic locks.

And actually, before that, you used the quote about Uber and so I'm really fascinated right now by the reduction in cost per square foot of commercial real estate, because of the fact that office spaces, to a degree, have been obliterated by COVID. Right. And, and how some portion of that is being taken up by cloud kitchens, which, in case you don't know, is basically like a shadow kitchen that's sitting inside of a shitty office space. And that people use effectively only for takeout for things like DoorDash, new breeds, and what you may or may not know, depending on how close you are to teach, is that Travis Kalanick, so let's call him that from now on, who was one of the founders of

Srini: All right, so let's, we'll, we'll go back to that in a bit more detail. I mean, speaking of Oculus and, and things that have made possible, you know, you and I were talking about the fact that we shopped around the idea for a TV show. I wanted to do a David Letterman-style Netflix-type thing. And I realized when I got inside the Oculus, I was like, wait a minute. I can host a guest like you and if you had an Oculus, could be having this conversation in VR and I can invite every single person listening to this who has an Oculus. So we literally could create a live show and make people feel like they're there. That wasn't possible before. Yup. So suddenly, even something like putting on a conference, which used to be astronomically expensive, which I've tried to do before and especially trying to get the people at my desk. So I'd get paid to speak, but be like, Hey, what'd you come and do this thing for free? Even, I wouldn't do that now. But suddenly it's like, Hey, I'll feed you. You don't have to leave your home.

Julien Smith: Yeah, it has to be super good. And the production value has to increase over time. There was a period in time and I think you and I have seen many of those things Substack is probably, I, I'm, I'm very close to all those people because they, a lot of those companies tend to be funded by Andreessen Horowitz. And so my current company, and so. Just Substack. There was a phase where anyone could become one without an existing audience beforehand, and it could become very big on Substack. And some of my buddies like Lenny, Richard Ski, and a few others, or I have very meaningful substance packing, McCormack have very meaningful substance in those newsletters.

And then you have a set another phase, and this was true in podcasting where you had randos, who became hugely successful. And it was true on YouTube, same thing, right? When there was no production value, all that it took is just to be able to create something and have the impetus to do it. Now over time, it is definitely true that winner takes all or the winner takes most, but it is also true that the pie is getting bigger over time. And the amount of consumption that is occurring

Srini: Meant, when I started the podcast, I think that was in 2009, 2010 people said podcasts were dead. I was just very fortunate to be 10 years ahead of a massive cultural trend.

Srini: No. Well, I mean, even, you know, we were talking earlier about long-term perspective. I mean, Sam opened in his wife's nomination for the Startup School podcast. He actually said, you know, a lot of founders come in, they think, "Hey, I'm going to do this thing for three years, get rich quick," like Ashley and B. She said you defined a long-term perspective as 10 years.

Julien Smith: He's just completely right. I've actually seen it in court many times now. Like, Breather was created in 2012, 13. Its tenure arc was sold during COVID. Seven years in maybe. Right. I know that my arc with practice is going to be around 10 years. What I will say is that I do have a good feeling about it, once you have seen many tenure arcs, you're like, oh yeah, yeah. You go away from this feeling of, this is my baby. Oh my God. The stress goes away because a few of your 10 or seven to 10-year arcs have occurred. And you're like, this is my current. I really care about it, but like, I'm not going to throw myself off a bridge if my timing was off. Right. For example.

Julien Smith: And I will say you're one of the few that kept going. There were so many people. And by the way, you deserve enormous credit for this. Because most people started podcasting, as I started in 2004 when it was literally invented, but what does that matter? Because over all of that time, it's the people with the staying power or the people with gigantic audiences from elsewhere who were really able to keep growing and build a business off of it and succeed. I will say that that was definitely one of the weaknesses of my game, so to speak, back then is that I did create a lot of media and it was very, I participated in a lot of different things, but a lot of people were smarter than me because they had businesses behind it. And I, at that time, did not have a lot of business behind what I was doing because I was very like I was reticent about it. I actually, I would say like my, it was, I had a view a little bit then that business was dirty. My, obviously that's, that's completely changed around, turned around now, but it's the people that have the staying power to be able to stay in the space

Srini: Well, I mean, I think that makes a perfect segue to revisiting something else that you said in our last conversation. Take a listen.

Julien Smith:  The way that I generally make decisions is: What is the least competitive thing to do? What is the newest thing to do, where only a few people can follow me? And based on those things, you can probably create a career or a couple of years of your life where you're going to have a cool, successful thing for a while, and then maybe a new trend will emerge and then you'll go on it and do that thing. You have to almost have a sense for yourself. I have nothing to lose, so if I have nothing to lose, I'm just going to go all the way and create the most ballsy thing that I can possibly create. That's a really difficult thing to do, but it gets better with practice. And hopefully, as you get older, you don't become risk-averse, which I'm concerned about. Well, let's talk about...

Srini: A couple of things here in terms of both, you know, risk aversion, managing psychology, you know, sticktoitiveness, I mean, you've seen multiple tenures arts. I mean, I think I realized throughout this for definitely been times when I'm like, what the hell am I doing? Why am I not where I want to be? You know, I'm in year 11 now. And I'm like, okay, I'm nowhere near a $500 million exit. And sometimes like, I think. You know, my parents are questioning my sanity. I still have days when I'm just like, okay, how am I going to make ends meet at times? You know, I mean, it's not what it was six, seven years ago, but it's still stressful of course, far from.

Perfect. So I wonder what you think about it. I mean, I think that's like a perfect thing to talk about in the context of a coaching company. You know, risk managing psychology and, and also. You know, having the audacity to stick with it. I mean, to me, my, my reason for sticking with it was like, I don't have an alternative, anybody

Julien Smith: A job. Yeah. But there's some comfort in that. Right? There's some comfort in saying it's never going to be someone else. So it's gotta be me, which results in you having to make something work. And so I, that really, that risk tolerance that I'm talking about in that clip. And by the way, this is an amazing format to do something that had never occurred to me.

But it's actually amazing that you've done it. Is that risk tolerance a way of talking about asymmetric upside versus downside? Like, like in venture often people will say, well, I can only lose one-time money. Like if I put a hundred thousand dollars into something for example, it'd be like, I can only lose a hundred thousand dollars, but if I've done my job well, I can make five, 10, a hundred, or whatever times my money, if I am really smart about it. So risk tolerance is a way of understanding asymmetrical upside versus downside.

One thing that is definitely true is when you are younger, you have less and less and less and less to lose. Your son has nothing to lose, which is actually incredible

Srini: Totally. I always say you want to start trends and I'll follow. Let's wrap this up. I've got two final questions for you. I mean, you've had, you know, by most people's, you know, the measure, quite a degree of success. How has your personal definition of success evolved with each iteration of your career?

Julien Smith: I will say it's much more now about a happy life. It's true that there is still a part of me that measures myself by my public perception. Like, how people think of me, but I've done enough successful-ish things that I feel like I've had a good run in my past. And the fact that I've had that now I'm much more like I'm going to build something that I really care about and that's gonna help a lot of people, but it's much less driven by public perception. And it also, people are going to know. Now I'm like, I just want it to be cool for the people that find it, that for whom it helps them. And I want to work with cool, smart people. Like it's the company that I just recently started about two years ago and finished a $10 million round these past couple of months. That company was started literally because I had some people from Breather. We were all like, we all really liked and respected one another and we said, let's do something else together. And it was based on the people and the quality of the people. And it still is based, even though we're probably 15 to 20 people

Srini: Well, I have one last question for you, which is how do we finish all of our interviews? What do you think it is that makes somebody or something unmistakable?

Julien Smith: I think you have to be authentically yourself. Probably. It has, it has to be some natural version. Right. The same way that people light up when you ask them if they're like guitar dudes and you, and, and, and you ask them about that and they just light up completely that's when they that's when you see the real them, that's when they recognize themselves. So, so if they can be that person, like the majority of their time, then that's unmistakable. Right. And then. It's probably about just being willing to express that as much as you can, like having the courage and having the willingness to really put it out there.

Srini: Amazing. Well, I can't thank you enough for taking the time to join us and share your story, wisdom, and insights.

Julien Smith: With our listeners, I was

Srini: I'm really thrilled to be able to have this conversation and reconnect after such a long time. Where can people find out more about you, your work, and everything you're up to today?

Julien Smith: Yeah. It's, it's pretty easy to find me a lot of places. So Twitter would be @Julien spelled the French way because that's where I come from. My company is at practice. co and I mean, I'm all over the place. Blogs, and podcasts, I'm always accessible to be able to help others and to try and make a difference.

Srini: Amazing. And for everybody listening, we will wrap up the show with a question. Thank you for listening to this episode of the Unmistakable Creative Podcast. While you were listening, were there any moments you found fascinating, inspiring, instructive, or even heartwarming? Can you think of anyone, a friend, or a family member who might benefit from this episode?

Julien Smith: Would you appreciate this moment? If so, take a second and share it today.

Srini: Episode with that one person because good ideas and

Julien Smith: Messages are meant to be shared.