#336: Scott Belsky — How to Conquer the Messy Middle

Scott Belsky (@scottbelsky https://twitter.com/scottbelsky) is an entrepreneur, author, investor, Chief Product Officer of Adobe, and venture partner with venture capital firm Benchmark. Scott co-founded Behance in 2006 and served as CEO until Adobe acquired the company in 2012. Millions of people use Behance to display their portfolios, as well as track and find top talent across the creative industries. Scott is an early investor and advisor in Pinterest, Uber, and Periscope among many other fast-growing startups, and his new book, The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture http://www.amazon.com/exec/obidos/ASIN/0735218072/offsitoftimfe-20, hits the shelves October 2nd. I urge you to check it out, but until then, please enjoy this interview in the meantime! This podcast is brought to you by FreshBooks https://www.freshbooks.com/pages/tim?ref=11864&utm_source=tim-ferriss&utm_medium=podcast&utm_campaign=2016&utm_content=email. 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• 0:01Speaker 00

  At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

• 0:08Speaker 01

  Now would be an appropriate time.

• 0:12Speaker 00

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 0:24Tim Ferriss?

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• 1:09Tim Ferriss?

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• 1:52Tim Ferriss?

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• 2:13Tim Ferriss?

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• 2:57Tim Ferriss?

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• 3:41Tim Ferriss?

  Hello, boys and girls. This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where it is my job to interview and deconstruct world-class performers of all different types, from business, sports, military, chess, you name it, science. We bounce all over the place. And this episode is going to be wide-ranging, not only focused on business or investing, although we do have an all-star in both of those arenas. The guest is Scott Belsky. He is one of the people I call most for advice on a wide range of topics. Who's Scott? At Twitter, at Scott Belsky, B E L S K Y, scottbelsky.com. Scott is an entrepreneur, author, investor, and currently Chief Product Officer of Adobe. Big, big company, you might have heard of it.

• 4:25Tim Ferriss?

  He is also a venture partner at Benchmark, one of the most famous venture capital firms anywhere but this one, based in San Francisco. Scott co-founded Behance in 2006 and served as CEO until Adobe acquired Behance in 2012. Millions of people use Behance to display their portfolios as well as track and find top talent across creative industries. He is also an incredibly successful early-stage investor and advisor who has been involved with companies like Pinterest, Uber, Periscope, among many, many other fast-growing startups. And his latest project is a compendium of insights and tactics for what Scott calls "the messy middle." We all know we have that initial euphoric start to big projects or companies, and then

• 5:10Tim Ferriss?

  you enter what you might have heard of in perhaps incubator parlance. In this case, Y Combinator, I believe, refers to it as the trough of sorrow. So you have this initial burst of adrenaline, and then there is a long middle period with any type of creative endeavor that can get really messy, and that is where a lot of people give up or get destroyed in one fashion or another. And then there are people who make it to the last mile and ultimately complete many of these projects or have some type of acquisition or exit with a startup. So this episode covers a lot of ground. We talk about a lot of these tactics. And if, for whatever reason, you're thinking, "You know what? I want to listen to this.

• 5:54Tim Ferriss?

  Scott sounds interesting, but I don't want to focus exclusively on business stuff or business building." Don't worry, there's a lot in here that transcends that. And specifically, we shift

• 6:08Tim Ferriss?

  Locations a number of times in this episode, we end up in the sauna at one point. And if you want a real life example of how I ask my friends for help, because I was getting all wound up about a very, very top of mind situation when Scott showed up in my house, jump about 55 minutes ahead from where we begin the interview. So the easiest way to do that, if you want to, that's when we are in the sauna and I ask him for help, is as soon as we start, you can kind of hop an hour into the audio or so, and then jump back like five minutes, and it should be around there. But there's a ton of stuff that you can mine out of this interview. Scott is a great guy, and I had a blast hanging with him.

• 6:51Tim Ferriss?

  And with that, I will let you also, through your ears, hang with none other than Scott Belsky.

• 7:02Tim Ferriss?

  Scott, welcome to the show.

• 7:04Speaker 00

  Thanks, Tim.

• 7:05Tim Ferriss?

  Here we are at the kitchen table. I didn't think we would have a chapter two today. We met earlier for some oysters and beverages. And caught up, and I was picking your brain on a number of different things, and we were trading stories, and I realized that you have, and you're gonna know what I'm referring to, how many Evernote notes?

• 7:29Speaker 00

  Well, a lot of Evernote notes.

• 7:30Tim Ferriss?

  But specific to what we're probably talking about?

• 7:32Speaker 00

  Yeah, I think it was, this, it started at maybe 830 or so, a couple of years ago, when I started trimming it down.

• 7:40Tim Ferriss?

  And you've been capturing lessons learned, maxims, mantras for yourself in the process of developing this career, and I hope this doesn't come off the wrong way, but you've worn so many hats, it isn't a single career. It seems like you've lived many different lives, and people have already heard the bio that I read in the intro, but perhaps you could indicate the roles that you've had in the companies that you've been a part of, because they are so varied, and I just want to underscore how eclectic it is.

• 8:17Speaker 00

  Yeah, eclectic for better or for worse. But I was an entrepreneur back in 2005, starting a very small, almost a lifestyle business at that point to help organize the creative world, a company called Behance. Five years of bootstrapping as a small team, valuing resourcefulness over the resources we didn't have, a few near-death experiences in that process, then became a venture-backed company, which is a little bit more of a traditional Silicon Valley-like story, being venture-backed for a few years, growing really fast, went through an acquisition, then started, found myself working in a very big company as a vice president, given what I came in with, as well as a few other projects, and

• 9:01Speaker 00

  a few new muscles there, navigating a big, big corporate experience. Then I decided, you know what, I've been a seed investor for a while, I like this, people are telling me I should be an investor, jumped in and became a general partner at a venture capital firm. Total context switch, learned a lot of things, some the hard way, then realized I miss building, wanted to get back to it. Now, I'm an executive at a big public company, Adobe, the same company that acquired us, but totally new position. And I would say that whenever I think about best practices, if there's ever such a thing, or I actually realize that they all conflict based on whatever context you're in. And the things that I

• 9:43Speaker 00

  thought were super important as a startup, and were the rules of the road, if you will, actually may be the exact wrong playbook to play at a later-stage company, or then at a public company, or an eventual capital firm. And it, in some ways, makes you kind of throw everything you accept as conventional wisdom out the door, because you realize that everything kind of conflicts, and it's really based on the context. But in some ways, there are also some patterns and some lessons learned from the clashes of wisdom.

• 10:13Tim Ferriss?

  And the, the different positions that you've had, the different roles you have played, are also of interest to me because you've ended up filling the seats on both sides of the table, in different relationships and different transactions, right? Entrepreneur, investor, startup founder, and potential acquirer, right? I mean, you're in a position yourself now. Where your younger self could have been in some capacity, talking to you.

• 10:46Speaker 00

  Yes.

• 10:47Tim Ferriss?

  And you've collected these notes over time. So I thought, what the hell? And we talked about this, maybe or maybe not, after a few glasses of wine. But earlier today, we should just record a podcast. So here we are, late night at Shea Ferris.

• 11:07Tim Ferriss?

  And we're going to record this episode, half of which may occur inside a very, very hot truth barrel, i.e. barrel sauna TBD. But we're just going to wing it. So let's, let's start exploring some of these, these max, some of these notes. And you can tell us the story behind it.

• 11:25Speaker 00

  Yeah.

• 11:26Tim Ferriss?

  And we're just gonna, gonna riff. So let's do it.

• 11:28Speaker 00

  Sure. Well, I have to say, when I started to, it was actually on a plane a couple of years ago. I was going through this file of about 800 and something notes. And I realized that, first of all, if this plane goes down, they're all gone. And, and second of all, this is really disorganized. Should I start to kind of organize them based on some theme? And ultimately, it came down to three things. One was endurance. How do you navigate the endless self doubt, uncertainty, ambiguity, extraordinary volatility in, in whether it's a new venture or a turnaround of something or a bold creative project? I feel like there, a lot of them, that was the theme. Like, how do you just stick with it? With it long enough to figure it out? How do you have the persistence and the patience?

• 12:12Speaker 00

  And, and everything related to endurance? The second theme that came out, which is a pretty broad theme, I would say, and maybe I was cheating a little bit, is optimization. Now, how do you make the product better? How do you make the team better? And also, how are you constantly, in some ways, A B testing the way you work and making yourself better? And, you know, obviously, I'm sure books could be written on that, but that was my second theme. The third theme, which is a bit more narrow, I call the final mile. I found that whether it was entrepreneurs I've worked with over the years that that involved me in their acquisition process, or writers that I know right before their book comes out, people in the final mile of something being done, or almost being

• 12:53Speaker 00

  done, there's a lot of interesting stuff that happens, some self sabotage, new doubts, you think you you know what you're doing because you got that far and then you realize, oh shit, I don't know what I'm doing. So those were the three themes. And I was like, okay, for starters, let me just start to break them into themes. And that's where it all began.

• 13:13Tim Ferriss?

  So you got the buckets. Let's let's dig into some examples.

• 13:18Speaker 00

  Sure. No. So I think that, you know, if we go in that order, and you think about endurance, one of the one of the there were a number of different observations around, and especially from my own experience, building a startup and boot shopping for five years and keeping people when we actually weren't really making any money. We didn't really have customers, no one really cared about or knew about what we were doing.

• 13:43Tim Ferriss?

  And you said organizing the creative world, I think may have been the wording you use. What does what does that mean in practice? Like, what were you trying to sell?

• 13:51Speaker 00

  Yeah, for Behance, we the insight was that the creative world, meaning any sort of design photographer, architect, illustrator, any in the world of of creative production. These are some of the most interesting people in the world. They make our lives interesting. It's also the most disorganized community on the planet. There's very little attribution about who did what. These folks oftentimes feel like their careers at the mercy of circumstance. And the idea behind Behance, which was my startup back in the day, was to help organize these people, in some ways, build a LinkedIn for the creative world, you could describe it that way. And some of the products to help them get organized. And but we didn't really know what we were doing. It was a bit of a team of misfits in the sense that

• 14:33Speaker 00

  all of us had roles we weren't necessarily qualified for when we were building this team in the early days. And what I learned very quickly was that the the idea that we wanted to come together for that thing that motivated us to In some ways, in some cases, quit our jobs or take huge risk or start incurring more debt in our lives. That was enough to get us to get started. That wasn't enough to keep us engaged on a daily basis for years. And I think that's one of those myths that if the vision for what you want to achieve in the long term is great enough, you can just keep persisting and keep at it. In fact, you need to short circuit your reward system in some ways.

• 15:15Speaker 00

  And I remember there was a conference we had a number of years ago for Behance where Fred Wilson, venture capitalist in New York spoke, and he talked about two great addictions in life, heroin and a weekly salary. And his point was, when you unplug from either one, it's very difficult. And if you think about, from birth, we're almost oriented towards short-term rewards, checks on the tests, grades in the courses, salary, bonus, and whatever. And when you embark on something very long-term and you unplug from that, maybe you have to supplement it with something else. That is a creative endeavor when you're leading a team. I mean, for us, there were a few fun things we did. I mean, for starters, we had a name for our company called Behance, which didn't mean

• 16:00Speaker 00

  anything, didn't exist. And so, every time you typed it in Google, it said, "Do you mean enhance? Do you mean enhance?" And so, short-term reward, number one, was maybe we won't be a mistake someday. Let's get enough people to put portfolios up there. Let's get enough blog posts and link backs and whatever else. And we would always search Behance and see if we actually showed up. It felt like a more achievable way to keep us oriented. And soon enough, we actually did suddenly show up as a legitimate result. And I kid you not, like, six months later, Beyonce became super popular. We lost that for a little bit, but then we got back. There were all kinds of fun things like that. We made bets all the time about things that people would have to do if we got to a certain

• 16:42Speaker 00

  milestone, and those became this new reward system that governed and actually kept us together. And we remarkably didn't really lose many people, at least voluntarily, for a number of years.

• 16:57Tim Ferriss?

  What else do you attribute that to? And for people who are listening, and they might have a small team, and they're in that position of realizing perhaps that the initial irrational exuberance of the big vision and the grand unveiling of this

• 17:14Tim Ferriss?

  World-changing company is actually going to take quite a few years and that people are starting to, I'm not going to say founder, but realize the gravity of that reality is beginning to hit them. And the CEO, maybe sole founder, maybe co-founder is thinking, oh shit, I need to whip up some shorter-term incentives or motivating goals or anything to keep this team together. So there isn't some form of mutiny or people just start dropping off. Do you have any recommendations for that person?

• 17:46Speaker 00

  A few different things. You know, in some ways, I use the analogy of driving your team in a car with the windows blacked out. So no one knows where they are and how far they are in the journey. And that is sort of what a startup experience is like, by the way. You don't know where those milestones actually are. You don't necessarily even know where you're going and how far along you are. The only thing that makes that more comforting or tolerable is a great narrative during the journey. Okay, you know, we just crossed the state line. Oh, you know, there is this on the right. There's this on the left. Even if it's not necessarily answering the question of, well, how far are we and where exactly are we going? There's something about being talked through it. And I think

• 18:29Speaker 00

  that's one of the jobs of someone at the helm is to build that narrative. And part of that is a creative endeavor, right? Because you don't necessarily know what to say, but you have to say something. And I think that's one of those maybe less discussed muscles of a leader of a startup is to, is to build that narrative and keep kind of walking people through. I mean, one of the things that I would oftentimes do is play out best and worst-case scenarios with different dimensions. So.

• 18:57Tim Ferriss?

  You mean play out for yourself or in front of employees?

• 19:01Speaker 00

  In front of the team.

• 19:02Tim Ferriss?

  What would be an example of that?

• 19:04Speaker 00

  Yeah. So, I mean, a few things. One is, we had. A few different products we were kind of pursuing, or a few different angles, rather. And I would oftentimes play out, hey, if this doesn't work, maybe we can reuse the technology for this. Or if this business model doesn't work, we'll try that. And you know what? If this doesn't work, look at what we will have learned over the next three years. I mean, we are going to be so marketable. This is going to be one of the best experiential educations any of us has ever had. And we're going to be able to get salaries at X instead of Y. You know, and that was also part of the huh. You know, I would remember like people feeling like a little more comfortable. When in fact, the reality is we were working in, again, complete ambiguity and uncertainty and a little lost.

• 19:46Tim Ferriss?

  Well, this, this is, I think, having observed some excellent, great, good, mediocre, passable and not so good CEOs over the last, whatever it is, 20 years now. Jesus, I'm getting fucking old. Anyway.

• 20:07Tim Ferriss?

  This is, I think, one of the most under discussed and valued sales functions of the CEO, right? They think of selling investors, they think of selling employees, but for the hiring of those employees.

• 20:20Speaker 00

  Yep.

• 20:21Tim Ferriss?

  But to retain a team and in the early days, this is so, so important.

• 20:28Speaker 00

  It's merchandising. I mean, think about the, the amount of capital that is spent on billboards and advertising that compels us to take action and do things every day. It's obviously powerful, yet why don't we use those same mechanisms to get our team to do things, to get ourselves to do things? I think it's an important muscle. You're also trying to, you're trying to help your team accept the burden of uncertainty. Right? And it's just so much easier when this stuff is around you.

• 20:56Tim Ferriss?

  So you also use.

• 21:00Tim Ferriss?

  Dare I say, I do dare. Strange incentives for yourself. And I was thumbing through some things that you've sent to me in the past in terms of answers to questions and so on. I don't know if you still do this, but you have your like Scooby snacks and deep, deep work rewards. Do you still do that?

• 21:20Speaker 00

  I still do.

• 21:21Tim Ferriss?

  Could you tell people just briefly what that is? Because I'm sure a lot of people are listening who are perhaps solo entrepreneurs or freelancers who might be for a lot of the day by themselves. So they have to talk to themselves the way that you were talking to employees.

• 21:35Speaker 00

  Yeah.

• 21:36Tim Ferriss?

  So what is this? What is, if you could just describe this for people?

• 21:40Speaker 00

  The, well, I mean, it's, I guess it's short circuiting my own reward system. I find the process of writing, for example, pretty painful. I have a writing playlist that I only allow myself to listen to if I'm writing and

• 21:53Tim Ferriss?

  Can you listen to it from the get go or do you have to?

• 21:55Speaker 00

  To be in the zone. And when I find myself going to social media or checking email or whatever, I make myself stop it and I'm not allowed to start it again until I'm back in the writing zone.

• 22:05Tim Ferriss?

  What are some of those, those tracks? Do you, do you remember some of the artists?

• 22:09Speaker 00

  Yeah, there's, um, there's a couple of like great sort of melodies that I kind of love. I mean, one is this piano melody by a woman named Carly Commando that I discovered once. There are, gosh, I mean, there are just a few other things that I love that I think I can work with that I don't want, I didn't want to burn out. But I also, you just wanted it to be like that reward. Like when I'm back in the writing zone, I'm feeling it.

• 22:34Tim Ferriss?

  And is, do you?

• 22:36Speaker 00

  And they're snacks.

• 22:37Tim Ferriss?

  And the snacks. So what are the, what are the snacks? And when are you allowed to have the snacks?

• 22:41Speaker 00

  Oh man, you know, those, these like really nice kind of flaky buttery things that are dipped in chocolate that they sell in those, I don't even know what you call them.

• 22:48Tim Ferriss?

  Yeah.

• 22:49Speaker 00

  Those.

• 22:50Tim Ferriss?

  Delicious snacks.

• 22:51Speaker 00

  The, uh, the chocolate flake bars that I get from London whenever I'm there. Only, only something I can have when I'm in the zone writing in this case.

• 23:00Tim Ferriss?

  So in the zone now, as a, as a little piglet myself, I might be inclined to be like, oh man, just nailed my first paragraph. Let me have some chocolate.

• 23:09Speaker 00

  Right, right, right.

• 23:10Tim Ferriss?

  So, so what's the bar for in the zone?

• 23:12Speaker 00

  Yeah, no, it's, it's when I, when I get a material chunk done, when I feel like I, I mean, as I, as I talk about this, this sounds ridiculous, but it's not, right? Like how?

• 23:24Speaker 00

  Why don't we take active, more active roles in governing ourselves and merchandising and playing, you know, sales tactics with ourselves, with our teams?

• 23:30Tim Ferriss?

  Yeah.

• 23:31Speaker 00

  Just like we do with customers in the rest of the world. And yes, it works for me. Chocolate, good music. It will, uh, sometimes that's enough to get me doing what I'm supposed to be doing.

• 23:43Tim Ferriss?

  Okay. So we've talked about reward systems.

• 23:48Tim Ferriss?

  Are there any other guidelines that you, or suggestions you would make to a founder who finds himself in that very kind of embryonic stage when they're realizing, wow, okay, I thought I, in my mind, had the, the excitement of a sprint, but this is not a sprint. This is going to take some time. Any other recommendations for keeping a team motivated or examples?

• 24:10Speaker 00

  There's a lot of like tough moments in that middle. There are a lot of meetings that don't have answers at the end. There's a lot of, um, there's a lot of periods, again, of that ambiguity where you're kind of going in circles. There's rework. You, you launch and you realize that it was built on the wrong tech stack or that it was, you know, totally toward the wrong type of customer and you have to redo it again. And, and, um, leaving your team constantly with energy, even after those very difficult bouts. Uh, I remember, you know, one guy I worked with, uh, a guy named David Wadwani, who's now the CEO of AppDynamics, uh, a company out in Silicon Valley. But, uh, he, um, I remember every time I was in a meeting with him and they could be like just the most depressing meetings.

• 24:53Speaker 00

  He would always kind of end with a recap that would again, like spin it around towards, we got this. We've got the right people. These are the open questions. This is the plan to solve them. And everyone would kind of end on an up, right? And it's another one of those tactics, right? To keep people engaged, enduring.

• 25:13Tim Ferriss?

  Well, one that we talked about, which isn't necessarily a reward system, but it reminds people why they're doing what they're doing and why they've made this gear shift into entrepreneurship. You gave me an example earlier, uh, when we were hanging out, uh, that was related to your, I guess, suppressed memories during the five years of, of bootstrapping. Uh, when you went back to, to look at photos from that period, to see what was going on, like, wow, I really can't remember much from that period. What did you find? And this is something that comes up when I talk to people like Derek Sivers or others, when they want to allow people working on the products to see what?

• 25:58Speaker 00

  Well, you, and it goes back to that reward thing, I think, as well. I went back in my phone to that five years because I was actually surprised by how much I had forgotten.

• 26:09Tim Ferriss?

  Yeah.

• 26:09Speaker 00

  And I was wondering, did I forget it because I wanted to?

• 26:12Tim Ferriss?

  Yeah.

• 26:12Speaker 00

  Was there just nothing that is worth remembering? And, and so, yeah, you know, I flicked back really quickly in my phone back to those years. And, and what did I find? I found tons of screenshots. I found a few, you know, I, I remember how many late nights I was always trying to find like the flaws of our product and send them to our team, like this kind of never feeling done sense. I also found a lot of random screenshots of people saying nice things about the product. And then I remembered, gosh, I used, I used to always try in a regular rhythm to send those around. We didn't have Slack at the time, but you know, you would post them on Slack now, I guess.

• 26:52Speaker 00

  Those are again, like those little, you know, jolts of reward that are keeping the team feeling it's, you know, that this is, it's the narrative, but it's, it's, it doesn't, it doesn't happen naturally. Right? And you have to, you have to look for it, you have to merchandise it. But yeah, I was surprised by how much of that five years was just kind of this, gosh, like, late nights, because you can also see like the, the timestamps of screenshots. It's like, gosh, I was lying in bed at 2am looking at typos and stuff and sending around. But, but that was, that is, that is a big part of it.

• 27:26Tim Ferriss?

  And once again, you can use this for yourself. I mean, I, anybody who has listened to this podcast long enough or read any number of the last few books that I've written knows that I've had bouts with depression, runs in the family. And I seem to have, and I'm working on it, but a selective lens for looking, for searching for what is wrong. Right? And I think that at some point I had it stuck in my head. This was taught, this was definitely nurture, not nature, not by my parents, by, by other, I think, teachers and coaches, that the good stuff takes care of itself. Let me tell you what you need to get better at. Right? And so I just developed this habit of always looking for what is wrong. And when you do that,

• 28:09Tim Ferriss?

  It can, it can put you, or it can put me at least into perhaps a productive space, but a funk that follows that productivity at times. And so I will take screenshots of occasionally of really meaningful, say, letters or comments from fans and I will favorite it on my, on my phone so that I have a few things. This is actually something I picked up from comedian Whitney Cummings. Sort of the, the screen of Zen, so I'll have like photographs of my dog, photographs of some of my best friends and my family. And then I'll have like a handful of these to remember like, oh yeah, that's why I like slog through the fucking neighborhood of the internet where half the people are throwing

• 28:49Tim Ferriss?

  like potted plants at your head out of the windows and deal with all of the sacrifices is ultimately for, for this, like where what we do touches somebody else. And it's, it's so easy even now for me to get kind of mired in various details that are an important piece of the whole, but to kind of forget when the whole is put out into the world, what it can do, doesn't always do it, but what it can do.

• 29:19Speaker 00

  And that's like the positive part that, um, that helps you keep going.

• 29:23Tim Ferriss?

  Yeah.

• 29:23Speaker 00

  I think there's also though, a, um, the other discipline, um, belief that first of all, you just have to sometimes just do your fucking job.

• 29:34Tim Ferriss?

  Right. I think that was your answer in travel mentors to, uh, what do you do when you feel, what was it scattered or overwhelmed? I whisper to myself, Scott, do your fucking job.

• 29:45Speaker 00

  You know, I do. And, uh, especially in moments where I've had to make a difficult move, fire somebody, um, make a difficult call, have a difficult meeting. There is that sometimes whisper of, uh, hey, yes, I could try to, you know, find other ways to make me feel good about this, or I'm just gonna tell myself that this is what it takes.

• 30:07Tim Ferriss?

  What I've never asked someone because, uh, Well, in many cases, these are people I've never spoken to before that I'm interviewing, but we've spent a lot of time together. Is there an emotion that you returned to a lot that was disabling in the five years when you were bootstrapping or afterwards? Like, some people have a default emotion that crops up in certain periods of stress. Mine was for a long time. I think I'm a lot better now, anger. Some people, it's like guilt, or depression, or sadness, or a feeling of being hurt. It could be any number of things.

• 30:46Speaker 00

  You know, for me, it's probably two things. I think that it is the realization that I'm not my best self when things are going the best, or when things are going really badly. When things are going really, really well, I'm not my best self because my ego can get in the way. And when things are going really badly, I'm not my best self because my fear is getting in the way. And so, when it comes to that question around self-awareness, I think that was actually a big breakthrough, or at least personally for me, was like, gosh, it's when things are going really well that you start to say, hey, you know, we don't have to pay attention to competition anymore, taking our eye off the ball, hey, we must have, we must have actually, you know, there's a false attribution problem, we must have done everything right, so we're going to keep doing that stuff.

• 31:31Speaker 00

  And then, again-

• 31:32Tim Ferriss?

  Right, rewarding good outcome without looking at process.

• 31:35Speaker 00

  That hurts. And that, you know, that can be a fatal flaw. And when things are not going well, and it's suddenly fear driving you, then you can start paying too much attention to competition and start looking like them.

• 31:47Tim Ferriss?

  So is that, that's something you did at the time?

• 31:49Speaker 00

  Oh, yeah. I mean, I think throughout, throughout my journey-

• 31:52Tim Ferriss?

  Did you, did you notice that because you were taking notes on your own responses to things, or was it just a realization one day that those were patterns?

• 32:02Speaker 00

  Well, I think it's probably a little bit of both. I mean, on the fear, for example, there was a, um, there were the early days of Behance. There was another, um, product out there called Dribbble. That was doing a little 400 pixel snapshots of people's work. And by the way, that always looks better than the full project because you can pick which little 400 pixel by 400 snapshot you take and get a nice little beautiful drop shadow and that will always look great. And we were just sort of bewildered by this. It's like, wow, like it's taking off so fast. It's obviously like, um, a, a real differentiation from our product. And the fear of that made us suddenly shift our shift. I can hear the tea.

• 32:42Tim Ferriss?

  I'm sure people can too. Fortunately, these mics are very directional, so we should be okay. That is, that is water boiling, folks.

• 32:49Speaker 00

  If you hear it, that is water, not my stomach. Um, but, uh, and you know what? We made a mistake. We took our eye off the ball. We spent a few major cycles of our business trying to make our own version of this small little snapshot thing. And then we realized it actually distracted from the core part of the product that made Behance good. And it was again, like bad judgment out of fear. And I didn't have that self-awareness at the time to realize that I was skewing our entire product roadmap and convictions that the team had out of my, you know, being at a low point in that, in that, in that example. So I think that's one of those examples where it was more in retrospect. Um, I think at the time though, I just tried to find, I tried to ask myself why I react to things in certain ways.

• 33:34Speaker 00

  Why did that meeting make me feel unsettled? What was it? Like, is this something that someone said? Is it, um, and, and if it was, if I can trace it back, you know, why does that either make me afraid or make me feel like, uh, I think you have to be kind of prompting those questions and

• 33:51Tim Ferriss?

  What do you do with it once you have identified a reason? Or in the, what, you can answer either of these, but say you, you realize that you overreacted to competition in the case of Dribbble and ended up misspending a lot of resources as a result.

• 34:12Tim Ferriss?

  How do you ensure that doesn't happen again? Or how did you? Or you could, you could talk, because I think they're so interrelated. You come out of a meeting, you're like, why'd that unsettle me? Okay, well, is it fear? Is it something else? Is something else like, it's fear. What is it fear of? It's fear of this.

• 34:26Speaker 00

  Right.

• 34:26Tim Ferriss?

  What do you then do with that? Because, uh, I mean, I think the, the hardest advice to take is often the advice you have given yourself or already

• 34:35Speaker 00

  Yeah.

• 34:36Tim Ferriss?

  realize that you need to do. Right? I mean, uh, not to encant the, the Mr. Derek Sivers again, although we've been talking about him. So all good things, Derek. Uh, but I think he is the one who said in one of our conversations that if, if more information were the answer, we'd all be billionaires with six pack abs. Right? Like, we all have a very good idea of a lot of things that need fixing or improving. But so what, what then? Like you figure it out. And I'm asking selfishly because I've got tons of stuff to work on. What do you do?

• 35:08Speaker 00

  Well, uh, I'm still figuring out as well. But, but, uh, I would say this is where the team comes in. Um, I, I have, and I've always had people on my team that were really different.

• 35:19Tim Ferriss?

  Well, let's, I started to interject. This is, this is where the yerba mate can be my scapegoat. But let's take the meeting example.

• 35:25Speaker 00

  Yeah.

• 35:26Tim Ferriss?

  Uh, you don't have to identify any people, but let's get super granular. Like, is, is there something, doesn't have to be a meeting, that unsettled you? Like, walk us through what hypothetical or real kind of an example? And then what you would do after that? Like, how that would inform future behavior?

• 35:43Speaker 00

  Hmm. Well, I think, let's see, I'm thinking of a few recent examples. And, um, one is when, there's a meeting I was in recently where I came in with a number of priorities that I'm focused on. And, which ultimately means I want them resourced. I want to invest in these. Um, these are things I want to put my chips on. And, uh, and I felt pretty, you know, committed and, um, and felt like I did a lot of diligence. And then the, uh, the, kind of the question was, how could you say that all of these should be resourced? How could you not come in and, you know, really just talk about one?

• 36:23Tim Ferriss?

  Okay, so that was the response from the other side.

• 36:25Speaker 00

  That was the response from the other side, and it threw me off. I was like, one. You know, like, I've got lots of products and lots of things going on and, and, and every business is dynamic. How could you not have one thing? I mean, that sounds crazy. And it really threw me off. And, and then I, and then I started to think, gosh, like, maybe I am, maybe I'm doing what I always tell people not to, you know, maybe I'm spreading myself too thin. I am not, you know, having enough conviction on the one thing that matters. Am I a good manager? Am I a good leader? Am I being informed properly? Do I have enough data? Am I, you know, you, you start having all those kind of self doubts arise.

• 37:05Speaker 00

  And, and then I think, I mean, in this particular situation, I, I did a few things. I mean, one is I started to play out some scenarios in my head. I don't know, is there one thing that's disproportionately likely to make an impact more than everything else? And actually, like, I felt like out of the list of 10 or so things, like, there were probably a couple that I would say, yeah, like, if I, if I had to pick one or two, I think that those have an outsized proportion of, or likely to making an impact. So why wouldn't I just go all in? And, and then I started to realize, well, it's because I have some doubts on those and I want to hedge myself.

• 37:44Tim Ferriss?

  Are you doing this in your head in your office as a postmortem? Are you doing it on paper, typing it out?

• 37:51Speaker 00

  Usually I'm doing it on planes. I, I, I benefit from the disconnected period where you're just kind of letting things churn. It definitely does not happen in a meeting because in a meeting, you're defensive. You feel like you have to have a, a view, you have to have an opinion, you have to have an answer, especially if you're a leader. But it's really outside, right? When you're just disconnected and you're kind of letting it run through your head. And if you have, but what you have to be doing is, is starting from the belief that you're wrong.

• 38:20Tim Ferriss?

  Yep.

• 38:20Speaker 00

  If you start from the belief that you're right and everyone else is like, what do they mean? You know, these are my 10 things and I've already, you know, I know that these are all important. It's not going to get you anywhere.

• 38:30Tim Ferriss?

  Right. And it well, it sounds like you don't have to necessarily believe that you're wrong, but you have to as an exercise, a suit like what if?

• 38:37Speaker 00

  You do. And it's provocative because I mean, and you have to be provocative in your thinking, right? So, you know, I actually, when you, when I, when I, when I caught myself in the fact that it was actually sort of about hedging, then it's like, well, what are my doubts about those one or two things? And maybe I should just spend a cycle of my time on just those. And, and that actually, in this case, impacted a number of meetings I set up and conversations I had and some data that I requested and whatever. And I remember after that whole process being like, okay, like that was, that was like a good cycle of leadership right there.

• 39:11Tim Ferriss?

  This is a great example. I appreciate you playing along. So on the plane, when the announcement comes over the intercom and they say, we're so sorry, we're sorry you misspent another $12. The wifi is not working. Everyone else is cursing and you're like, sweet, I'm going to get so much self-development done. Are you doing this in your head? Same question, on paper, on a, on a computer, offline? How, how are you running through this, these, these what-if scenarios?

• 39:40Speaker 00

  I usually start in my head. And then I start getting a little anxious because I'm like, oh, you know, I'm actually, this is something I need to be, this is going to cause a chain of actions that I have to take. In which case I will then, I have also in Evernote, an action tracking list, where it's like the things that, if there's one thing I want to look at every day, that I'm sort of tracking that requires some action or thinking through or whatever, deep churning. And I immediately like kind of added it to the list. And then I think that, that's when it starts to become more of a process and less of a provocative inner, inner, inner monologue.

• 40:18Tim Ferriss?

  Awesome. That was great. Let's, let's dig back in, speaking of Evernote.

• 40:24Speaker 00

  Well, I think that one of those little notes that, that made it to the finish line for me was, was this question around suspending kind of disbeliefs.

• 40:35Speaker 00

  As another like tactic towards endurance. I remember my father as an orthopedic surgeon, but when he was a resident, he was working in one of those crazy New York City hospitals where people would come in with like overdoses and shooting wounds and stuff like that. And he was telling me that the most often kind of prescribed, especially on the cycle, on the psychiatric stuff that came in was, it was like, you know, 100 cc's or whatever of Obacalp, which is of course placebo spelt backwards. And, and how like, you know, as soon as, you know, someone would be like, Obacalp stat, you know, 100 cc's, that would suddenly, you know, that would switch something, you know, in a lot of these patients' minds in terms of like where they felt they were in their hope. Right? Yeah.

• 41:18Speaker 00

  And, you know, that always stuck with me. And I was always kind of wondering like, kind of, how do I prescribe that, you know, to myself? And I think there are many different tactics there. I mean, one that I've heard from a number of folks who have worked at Google over the years and have been in certain meetings with Larry Page where he'll say, "Great, you know, good plan. How do you do 100x that?" And that jolt to the system suddenly throws the, the current project plan out the door. Like all the kind of near-term doubts you had don't matter anymore. It's like 100 times that, like, we have to be doing something completely different. Right? And in some ways, it's sort of the same effect.

• 41:58Speaker 00

  Because first of all, the disbeliefs you had in your, in your more reserved plan are suddenly out the door because that sounds easy suddenly. Because this new thing, like, I don't even know where I'd start. And, and I, I think that there's some, there, there are ways we can make sure that we just have exponentially more like belief in ourselves at times. Now, part of it also is, is a, is also

• 42:28Speaker 00

  Taking pride in how naive you are in certain areas. I remember talking to the Airbnb guys and a few other teams that talked about how they didn't even know the terminology of the industry they were trying to compete in. And how that actually was a very empowering thing because had they known that, they would have realized that some of their numbers didn't match up early on and they would have certainly abandoned, you know, the project before it actually became a business. So I think that there's sometimes, you know, hiring people that think differently or don't have, don't have the traditional expertise that you think you're needing to hire.

• 43:04Speaker 00

  I think you sometimes have to have to recognize the benefits in not, in not knowing too much.

• 43:14Tim Ferriss?

  Right. The, the constraints of an industry which may already have been, you know, obsolesced or expired in some way, who knows, like any number of, it's like, I really want to know the story of why we had to wait until whatever it was 20 years ago to have wheels on luggage, right? Like what? What was it? What was the inertia or lack of movement that made it take so long? It's incredible. I don't know the answer, but.

• 43:43Speaker 00

  I don't either.

• 43:44Tim Ferriss?

  What, what other tools do you use when you are talking to someone else? Because they then could be telling themselves perhaps something similar later as self-talk. When you meet a founder who's just getting crushed under the weight of their own self-doubt. And maybe they just had to lay off half the company. But there, let's just assume for the time being that there is product market fit, right? Like it is solving a problem, but they're just like, I'm not a good CEO. I'm not a good fill in the blank. I don't know if I can do it. They're down. What do you say to people like that? When they're in those circumstances.

• 44:23Speaker 00

  Well, I usually start by reminding founders that one of the greatest competitive advantages is simply sticking together long enough to figure it out and how they shouldn't necessarily beat themselves up about the daily volatility because it's basically just a series of ups and downs in which you hope you have a positive slope at the end of the day and you hope that every, you know, next low is a little higher than the one before it, right? And if you can just have a team stick together long enough and if you have continued conviction in the end state, then it's really a matter, it's a fight against time.

• 45:08Speaker 00

  And I really believe that. I mean, some people might say, oh, no, no, no, you can keep at it forever. A labor of love has a way of paying off, just not how you'd expect. And what, of course, you do have to, and when founders feel really low and sometimes they'll say, well, but how do I know whether I should quit or not?

• 45:26Tim Ferriss?

  Well, that's one of the most common questions that surfaces through the ether from listeners of this podcast and readers of mine is how do I know when to persist? Because you always hear, like you even said yourself, we had multiple near death experiences.

• 45:42Speaker 00

  Right.

• 45:43Tim Ferriss?

  Right? And if you're bootstrapping, my God, you know, you, you, there's a, oftentimes a survivorship bias in say, media coverage where it's like, oh, so and so took out like a 14th mortgage and sold his left kidney and now he runs Alibaba, you know, whatever. I mean, that's not a real story, guys, I'm making that up. But you, you hear these remarkable tales of throwing caution to the wind, but you, you don't get to see the bodies littered on, on the side of the street. So the question that I get from people who are trying to do the responsible thing is how do I know when to cut my losses and stop a project or just put rip on a headstone for my company and move on versus persist through these very difficult times?

• 46:27Speaker 00

  Well, I think, I mean, to me, the answer is pretty simple. First of all, you recognize the fact that everyone's kind of messy middle journey is, is, is, is at times hopeless and, and, and that self doubt is a real thing. And, and so you're not alone.

• 46:48Speaker 00

  However. If you start to lose conviction in what initially set you off on this journey, I mean, that's a serious thing. And however, if you have as much, if not more conviction for the problem you're trying to solve, then you have to stick with it. And that's actually what I typically will ask teams when they, when they're making, having that question.

• 47:10Tim Ferriss?

  How do you assess conviction?

• 47:12Speaker 00

  To me, conviction is, is really about knowing that the world is going to be a certain way based on all of the work and, and research and experiences that you're having. And I don't care what the company is, what the product or service is that you're trying to make. As you go about it day by day, you learn more and, and you start to realize where you were right and where you were wrong. And, and you're always wrong a little bit. I mean, that's the whole point about pursuing a product market fit. However, a lot of teams will, will realize, wait, like people actually don't need to do blah, blah, blah, blah. You know, they don't, they don't want to have, you know, laundry done within a three hour thing. And that's not a real opportunity.

• 47:57Speaker 00

  But since we raised $2 million and we've got a team working, like, we're just going to stick with it. Like, I actually think they should quit. However, if the answer is, oh my God, like this is even more inevitable than we ever thought. You know, this is more important. This problem is actually going to be bigger than we realized. And, you know, we just have so much more conviction, even though shit's hitting the fan right now. And gosh, our product is completely wrong. Right? And we, we have to start all over again. That team, I would say, you guys have to stick with it. Like, you're just, you're in that classic kind of mode of whoever sticks with it long enough is going to figure this out. So that, to me, is really where the decision point comes down to.

• 48:37Tim Ferriss?

  Have you, you know, rather than I was going to, I was going to throw out a tough case, but which you see sometimes, let's say, like Odeo way back in the day, although ultimately it transmogrified in some fashion into Twitter.

• 48:50Speaker 00

  Yep.

• 48:51Tim Ferriss?

  But they're pursuing what one could argue has become the now ubiquitous podcasting and things of that sort. But they paddled for the wave really early.

• 48:59Speaker 00

  Right.

• 49:00Tim Ferriss?

  Right? So it's, I guess, I guess sometimes it's a case where the, not to throw some investing. Quotes in here, but I will, since I'm well caffeinated. I don't know the attribution. I really wish I did. It might be Templeton, but the markets can remain irrational longer than you can remain solvent.

• 49:19Speaker 00

  Right.

• 49:19Tim Ferriss?

  Something like that.

• 49:20Speaker 00

  Well, timing is, uh, timing's a bitch, first of all. And, you know, investing is really less about, uh, is really less about the future and it's more about the present.

• 49:31Tim Ferriss?

  In what way?

• 49:32Speaker 00

  In the sense that you can have the greatest idea for 10 years from now, but, um, you know, it's again, like time is the enemy of every bold endeavor. Uh, it's just like super hard to keep people engaged long enough and keep, of course, capital and everything else you need to stay away, stay alive long enough until the planets align and the timing is right. Um, and I think that, um, and so that's why I would say that so much of, of investing is really about just knowing, like really what's right around the corner or already there. And, um, and then, and, and making your like product and team bets based on that knowledge.

• 50:10Tim Ferriss?

  Rather than 10 years in the future?

• 50:12Speaker 00

  Yeah.

• 50:12Tim Ferriss?

  Something like that.

• 50:12Speaker 00

  A lot of investors get stuck because it's easy to be a visionary and know that someday, yes, we will have flying cars. It does not mean that we need to be making flying parking lots at this moment.

• 50:26Tim Ferriss?

  What else do you have?

• 50:27Speaker 00

  I mean, one last thing on that front I would say is, um, something I, I've seen from a number of founders. I know Ben Silberman, uh, CEO founder of Pinterest, uh, is, is one, one person who really like thinks this way. Um, we were talking about that kind of long, you know, long journey, multi-years and, and, um, and the, and the merchandising and whatever. And this idea of breaking it down into chapters. Um, he, uh, when he talks about Pinterest, he'll talk about the fact that, you know, you're, uh, After product market fit, then there was the year of internationalization. And everything in the company was geared around, let's, let's, let's go global, let's stop these clones. And then there was a year around monetization.

• 51:11Speaker 00

  Let's figure out, how are we going to have a business here? You know, and, and each year has had, has been like a chapter. And that's how he frames prioritization and, and, and maybe, I guess, kind of goes back to that, you know, drive with, with, with no sight out the windows, like, how do you keep the team engaged? But it's, um, I think it's, I think it's a crucial point and it's part of, part of the endurance question.

• 51:37Tim Ferriss?

  You need, you use the, the metaphor of the, the kidnap car with the blacked out windows. One that I've also heard, not applied to startups, but to novels, actually, writing novels that I like quite a lot. And I do not remember the attribution on this either, but it definitely wasn't me, which is, uh, writing a novel is a bit like driving across the country with your headlights on.

• 52:03Speaker 00

  Oh, yeah, and Lamont, I think.

• 52:05Tim Ferriss?

  It very well could have been Anne Lamont because Bird by Bird is one of my absolute favorite books and I gift it to everybody, which I should probably also give to startup founders, quite frankly.

• 52:14Speaker 00

  Yeah.

• 52:15Tim Ferriss?

  I mean, a lot of the lessons are the same, but you can get to your destination, even though you can only see 20 feet in front of you. Right?

• 52:20Speaker 00

  I think that's part of it, you know, and the other part of it about it is, is how you kind of build patience into the way your team is built. I mean, if you look at a company like Amazon, um, I think there's a, there's, they kind of like have a cultural setup for patience. This notion of being willing to be misunderstood for a very long period of time. It's very embedded in the culture and, and you hear lots of ways that that's perpetuated. And then you take a company like Google, where I think actually they've tried to also, um, build patience in, but not as much cultural, more structural. So this notion of Alphabet and all these little companies that are able to kind of exist on their own,

• 53:02Speaker 00

  as if they were in a VC portfolio versus subject to the quarterly cadence of a large public company. So I think it's breaking those down into chapters, yes, it's the.

• 53:11Tim Ferriss?

  What did Amazon, sorry to interrupt, but, uh, the being misunderstood for a long period of time, is that as a company or as a person within the company?

• 53:18Speaker 00

  Well, it's, it's, it's. I think it's both. I mean, obviously.

• 53:22Tim Ferriss?

  And they do have their, whatever it is, not 10 commandments, but like the 10 tenets of Amazon or something up on Amazon somewhere. I don't, I don't recall exactly what they're referred to as.

• 53:31Speaker 00

  They also their, their original shareholder letter that they attached to every, you know, new shareholder letter and is sort of a bible within the company that also is all about that. It's basically saying, we're going to do what's right for the customer at the expense of a lot of other near-term opportunities to generate profit, right? And, and that is, that becomes a cultural tenant that obviously impacts the decisions that leaders make across their businesses. And I think that's why something like AWS became such a large part of their business.

• 54:02Tim Ferriss?

  Amazon Web Services.

• 54:03Speaker 00

  Yes. And, and you, you know, you see other parts of their business become huge businesses on their own because they're just willing to invest that way. You have to have a way though, because I think the, the realization here is that we are all impatient. I mean, part of my belief is that it's, it's just a biological, right? I don't know what our life expectancy was hundreds and hundreds, if not thousands of years ago, but it was a hell of a lot shorter than it is today. And so the notion of committing 10 years of your life to something was just insane and very unwise.

• 54:35Tim Ferriss?

  Right.

• 54:36Speaker 00

  And so when we do that, we are.

• 54:37Tim Ferriss?

  Get out there and procreate now.

• 54:39Speaker 00

  We're getting, we're going against our biological tendencies. And so you have to have hacks, you have to have those short-term reward system hacks. You have to have, you know, things like the cultural mechanisms or the structural mechanisms that push pages, the chapters, the merchandising.

• 54:54Tim Ferriss?

  Since I'm going with stream of consciousness for a minute and certainly going off script, you mentioned Amazon, I'm fascinated by Amazon. Strategery, this blog, has some fantastic, fantastic articles on Amazon and, and one recently, or not so recently, a few months ago on the acquisition of Whole Foods that I thought was really astute. I was introduced to it by Naval Ravikant. Thank you, Naval.

• 55:21Tim Ferriss?

  What do you read when it comes to investing, entrepreneurship, or other? Like, are there any newsletters, main Twitter accounts, anything that you can mention that you find really thought provoking?

• 55:37Speaker 00

  Well, Ben Thompson, who you just mentioned, is certainly, you know, one of the greatest thinkers, I think, on what's happening every day and always has a unique spin and has a lot of actual helpful self-references because he'll pull up things he wrote three years ago, not only to take a victory lap, but also actually it's a very helpful reference because it helps you kind of understand how some of these things could have been predicted and what the strategy is behind a lot of these moves. I think there are a lot of different investors that I follow or subscribe to newsletters for because I want to hear their view. And I'm trying to think of others.

• 56:18Tim Ferriss?

  Yeah, anyone who comes to mind, recognizing this is not an exhaustive or a complete list, but folks who you...

• 56:26Speaker 00

  Like Trent Griffin, a guy who has been at Microsoft for a long time, you know, close to Bill Gates and has sort of observed the software industry evolve and has a lot of insights around what's going on with all the mayhem these days with valuations and certain companies that are exploding without concrete business models. And he kind of always kind of boils it down to things like cost of customer acquisition, lifetime value of a customer. But it's just, again, like, I like people who come from a vantage point with an extreme bias, in his case, towards those fundamentals, trying to make sense of everything else that's crazy in the world. That's helpful.

• 57:10Tim Ferriss?

  Trent Griffin?

• 57:11Speaker 00

  His name is Trent Griffin, right. Josh Wolfe, who's a great investor in New York of a firm called Lux Capital. He's actually been an extreme skeptic of Tesla for a very long time, you know, calling out from his vantage point around some of the fundamentals. And also, I think he's used to... Entrepreneurs that have very kind of wild personalities for future narratives. And he pokes holes for a living in that. And so he has some perspective on on what he thinks, you know, may be happening on the Tesla front, which is always interesting. So he's another example of someone who just kind of, you know, grounds what you're reading on the headlines with some some different perspective.

• 57:52Tim Ferriss?

  Thematically, if you look at the non-investment reading that you do.

• 57:58Tim Ferriss?

  If you look at the pie chart, is there is there anything in particular that you're consuming a good amount of these days or over the last, say, year or two?

• 58:06Speaker 00

  You know, I think that there's some some biographies, the Doris Kearns Goodwin, you know, type stuff. The a few like the Walter Ixistin, like classic biographies. I think there's recently read Shackleton's Endurance, you know, story.

• 58:22Tim Ferriss?

  Appropriate.

• 58:23Speaker 00

  Yes. Which, you know, obviously relates to my thinking these days, which is just a phenomenal story. And there's so many interesting leadership lessons of counterintuitive things that he did that help you understand, you know, difficult decisions that have to be made.

• 58:38Tim Ferriss?

  And does anything come to mind?

• 58:39Speaker 00

  Oh, gosh.

• 58:40Tim Ferriss?

  I'm asking, I'm asking a lot, I know.

• 58:41Speaker 00

  Yeah, I know, but like, well, one actually thing that stuck with me was was, I forget like the exact scenario, but the crew had a choice of going back and getting all this food from the ship that was sinking. And everyone was like, we have to, of course, we have to get it, of course, you know, and we might be out here for years. We need as many supplies as possible. And but he didn't let them. And it was like, how, what do you mean? You're the leader. How could you put your team at risk? But he realized that by by allowing that to happen, he would be sending a message to his team that, yes, we will, in fact, maybe be stuck out here for years. And he knew that that would be almost like a death sentence to morale and to everything else.

• 59:22Speaker 00

  And so he just kind of artificially constrained their lifeline to some extent to make sure that the team knew that we just had to win. We had to survive. We had to move faster. Like, that's an example. It's like, wow, that's what are the what are the constraints that you should inflict on your team to make sure that performance is at a certain level?

• 59:43Tim Ferriss?

  Wow. You have to be thinking quite, quite quickly to play play through the different scenarios in your head and make that judgment call.

• 59:51Speaker 00

  And be willing to be unpopular.

• 59:53Tim Ferriss?

  Yes.

• 59:54Speaker 00

  And, you know, and take a risk. I mean, that's that's a risk, right?

• 59:58Tim Ferriss?

  So I think we can maybe look at one of the other legs of the stool, right? We have sort of three buckets. What would be one example? And I'm thinking, actually, this would be a good place to pause, put on our most fashionable swimwear, and move into the truth barrel, if you're open to that. I'm ready. Okay. Pause.

• 1:00:28Tim Ferriss?

  So here we are in my whiny sauna with a submarine light. You guys can look it up. Very old timey, looks like perhaps even a torture device in Rambo, attached to the coils of a mattress of some type. But we are sitting in a barrel sauna, the specs of which were given to me by Rick Rubin. Thank you, Rick. This is the second time out of whatever it is, 360-plus episodes, that I have attempted to do a podcast in a sauna. So thanks for being part of this experiment. Proud to be the second. And the acoustics might be a little weird, so bear with me, dear listeners.

• 1:01:11Tim Ferriss?

  And I thought I would segue by selfishly focusing on myself and a problem, a challenge that I ran into a mere 30 minutes before you got to my house. Because we were talking in the endure section about, at one point, the importance of postmortems and asking yourself why you responded the way you did to certain things, and how you do that work on planes. And it has led to insights and behavioral change. You seem to be, and this will foreshadow maybe the emotion that I suffered from and still suffer from right now as we sit here, having this conversation.

• 1:01:54Tim Ferriss?

  You strike me as a very even-keeled guy. I don't think I've ever seen you angry. Not that I've done anything to anger you, I don't think, but... My default in many situations, for reasons now known, some I'm sure unknown, has been anger. And it's been a very valuable tool. It's been a very useful fuel in some instances, for endurance even, to get things done. But I think that in many, many circumstances, it is misplaced and outlived its usefulness, and it's just corrosive for me. So here's what

• 1:02:32Tim Ferriss?

  happened. For the last few months, I have been interacting with this nonprofit to do volunteer work for them. And both to serve and to help, but also to learn a lot on the job, so to speak, volunteering for them. Turns out volunteering for them is pretty popular. Quite a few people want to volunteer. So it's not perhaps as straightforward as you might think. And I invested a lot of time in emailing back and forth with these folks for what I would consider an extended period of time. And I sort of in the back of my mind, well, we'll get to that. But I think about opportunity cost quite a lot as it relates to time.

• 1:03:15Speaker 00

  Time.

• 1:03:16Tim Ferriss?

  In particular, this nonrenewable resource that we have. So I put a ton of time in, which I hoped would end up in some type of solution for both sides that would allow me to get a bunch of valuable experience. So we agreed to a certain format, like, let's just call it four sessions, three or four sessions of volunteering in a very particular capacity, and set in motion all these plans. I said, are we confirmed? Because I'm going to be expending a lot of money and planning and logistics, like 20 grand, something like that, to actually get to you to do this properly. And they're like, yes, absolutely, no problem.

• 1:03:57Tim Ferriss?

  All right. So I received finally, after tons of, tons of back and forth, the schedule for my volunteering. On none of the days we discussed, for capacities that I do not match up with what we had planned, and I've already

• 1:04:16Tim Ferriss?

  Sort of irrevocably spent this money. Yep. And I'm just like, what the fuck? All right. And, and so I was just trying to kind of talk myself into some level of something resembling calm before you got here. I was like, you know what? I can't let this ruin my whole night. That's ridiculous. Right. And infantile. So let me throw on some music. Let me have some tea. Let me play with the dog. Let me do A, B, and C, which worked. Like I'm enjoying hanging out and it's not possessing me like a demon, but I do fear, because this is my pattern, that as soon as you leave now for the weekend, right? It's gonna fester. I'm gonna be thinking about this, which will not have any resolution. Yep. If it's, if it's going to have any resolution, which it might not, it's not gonna happen

• 1:05:01Tim Ferriss?

  until next week, Monday onward, right? So what would you do in this, in this circumstance? Or if you were in my shoes? As my even keel self. As your even keeled self. Right, right. Or, or what would you, how would you think about this in my shoes? Yeah, well, listen. Or work on it like that. This, and, and just for people listening, I wanted to take us in this direction, just for the, the first portion of this part deux in the sauna, because this is in fact, the type of thing I would ask you about. Yeah. You're a friend, and I get asked all the time, like if, if, okay, we've heard that

• 1:05:44Tim Ferriss?

  you're the average of the five people you associate with most. Who do you associate with most and why? And, and you would be an example I would give. I'd be like, I aspire to develop these characteristics, which I think are exemplified in Scott that I've not yet developed. And so you are even keeled. I think by normal standards, I'm pretty even keeled, but like I can turn into the Hulk also. And that is something that I would come to you. Yeah. With and say, Scott, you seem to know something I don't know, or have developed something I have developed. What would you do?

• 1:06:24Speaker 00

  If you were to have given me the story you just gave me in a sauna late one evening, and I was trying to give you advice.

• 1:06:31Tim Ferriss?

  Yes.

• 1:06:31Speaker 00

  What'd I say? I mean, I think that, I mean, first of all, I always ask myself when I'm angry about something, which I do get on occasion, is this in my influence or out of my influence? Like, is this something that I can directly end or shift? Or is this just like, the universe is against me at this moment and I'm just gonna have to like roll with it? And how much of my energy am I gonna give to it if I have no influence over it? And because then it kind of boils down to math for me. It's like, alright, like, this sucks, but

• 1:07:06Speaker 00

  the sunk cost thing kind of is oftentimes, you know, the wildcard in this notion of righteousness that a lot of us have, I think.

• 1:07:18Tim Ferriss?

  Yeah, and if it helps at all, I would say that when something is obviously outside of my control.

• 1:07:26Speaker 00

  Yep.

• 1:07:27Tim Ferriss?

  A crisis situation.

• 1:07:28Speaker 00

  Yep.

• 1:07:29Tim Ferriss?

  A death in the family, a car accident, something like that, I don't get upset. Or I can grieve in the case of a death, but I can, I can handle it very, very well.

• 1:07:40Speaker 00

  Yep.

• 1:07:41Tim Ferriss?

  Sunk cost fallacy as it relates to money.

• 1:07:43Speaker 00

  Yeah.

• 1:07:44Tim Ferriss?

  Doesn't really apply, for me at least. Like, if I make a bad bet, I'm not gonna follow up good money after bad if it's not working out. But with time.

• 1:07:54Speaker 00

  Yes.

• 1:07:54Tim Ferriss?

  Yeah, different story.

• 1:07:56Speaker 00

  I think the other factor.

• 1:07:57Tim Ferriss?

  I do get that righteous indignation, which I recognize almost always.

• 1:08:04Speaker 00

  Yeah.

• 1:08:04Tim Ferriss?

  Is a huge misexpenditure of additional energy and time.

• 1:08:09Speaker 00

  Listen, I mean, I'm with you and I think I feel this a lot oftentimes when I am stuck in a phone tree, you know? You know, it's just like, this is so expensive for, for me in the sense of how I value my time, like, gosh, you know, it's frustrating and I, I mean, the other question is. That I oftentimes ask myself when I have anger towards someone or something is, is how much can I expect people to be changed?

• 1:08:34Tim Ferriss?

  That's a good, that's a great one.

• 1:08:36Speaker 00

  Particular people, in particular industries, companies, nonprofits, at a certain stage, with a certain caliber of talent, with whatever else, like what can I expect? And what's reasonable and what's not? Because, listen, I think there's a part of us that believes that everyone can and should change. And so if there's an in-law or a parent or whatever, and they just are always aggravating us, it's like shame on them, they should change, and that can actually be where the anger comes out. And that whole kind of notion of teaching old dogs new tricks. I do say that to myself quite often. I'm like, hey, like, is this person really going to change? As a leader of a team too, there's only so much you can develop people into.

• 1:09:21Speaker 00

  And at some point, there's just certain limitations that I think people have. And I feel like I'm getting too pragmatic here. And of course, I believe in the potential of people and I believe in change. But when it comes to managing anger, I think it's also like, hey, you know, what is in my influence, what is out? How much can I expect this person, org, industry, whatever, to change? And, and, you know, and then, and then you, and then you have to become like a fierce protector of like extraneous energy.

• 1:09:48Tim Ferriss?

  How do you then, in a case like this, where I do actually want to volunteer, ideally in the original capacity that we, at least in my view, agreed to?

• 1:10:02Tim Ferriss?

  How, how would you then explore resolution or next steps in your own head?

• 1:10:08Speaker 00

  Well, the hack that I would use

• 1:10:09Tim Ferriss?

  Yeah.

• 1:10:09Speaker 00

  is that what I'm enduring in this case and putting up with, what I'm tolerating, is part of my contribution. So when I, when I go to nonprofit board meetings and that sort of thing, that I find, generally speaking, much less productive than a, than other organizations I'm involved in, or certainly startups, where it's all about, you know, what, what needs to get done? Let's get out of here, let's, everything's a scrum and it's a standing meeting. It's obviously very different. I do sometimes tell myself like this is, this is part of the condition that I committed myself to work under. I'm reminded of a great piece of advice that John Maeda, one of my mentors, once gave me. I think I may have shared a view.

• 1:10:54Tim Ferriss?

  Maybe. Could you, just for people who don't know him, who is, who is that?

• 1:10:58Speaker 00

  John is, is, is just a brilliant designer and thinker. He was the president of Rhode Island School of Design. Before that, he was head of MIT Media Lab. He spans both technology design. He also wrote a book about simplicity. But in my life, he's like my personal Yoda. The stuff that he tells me has to kind of roll around in my head a little bit to reveal its truth, but then it always kind of hits me. And in this case, I was at my first ever board meeting for the Cooper Hewitt National Design Museum, a Smithsonian institution with, you know, people with famous names on the board and, and, and a very kind of old institution, right? And it just moves slowly in some ways because that's how it has sustained for so long. Of course, it hasn't gone through radical change. That's what makes it in some ways

• 1:11:43Speaker 00

  sustainable. And, and I walked out of this meeting and I said to John, at the time, he was still president at Rhode Island School of Design. I said, gosh, like, how do you, how do you kind of manage such an unproductive meeting? Like, I think we heard a lot of people speak. We celebrated certain people for doing things. I don't think we got anything really done. I don't know what is actionable. And he looks at me, kind of shaking his head, being like, oh, you know, young Skywalker. He sort of looked at me and said, you know, Scott, all these cool startups and things that you're so excited about doing and building and founding, they won't be around in a hundred years. But this will, and it has been. And sometimes in life, you find something where all you can do is add a brick. And, and that

• 1:12:28Speaker 00

  is an incredible impact to something that will be around forever. And what I heard him saying in that is that adding a brick in a startup is pathetic. That's nothing. That won't get you anywhere. So in some ways, you have to change your expectations and have a greater tolerance for a, you know, a different level of, in some ways, performance or impact. And I think what you're describing is like this extra debt you didn't, or extra cost, rather, you didn't think you were signing up for. That is one way, at least for me, that I would excuse and be able to manage it.

• 1:13:00Tim Ferriss?

  Okay, so that, that gives me a cooler head.

• 1:13:05Speaker 00

  Even in this hot sauna?

• 1:13:07Tim Ferriss?

  For even in the hot sauna without my wool hat, Banya professional Russian style. We'll cover that another episode. Especially important for bald heads, by the way, but another time. So now I have a cooler head.

• 1:13:23Speaker 00

  Yep.

• 1:13:24Tim Ferriss?

  For the email or phone call. How do you think about that?

• 1:13:31Speaker 00

  Is the question, how do you now keep a cooler head?

• 1:13:34Tim Ferriss?

  Well, I mean, the options to me, I'm sure are many, but the ones that come to mind are I can accept what they've suggested, which is in no way representative of what I.

• 1:13:46Speaker 00

  That wouldn't be you, from the person I know.

• 1:13:48Tim Ferriss?

  Yeah, would not be me, agreed to or particularly want to do.

• 1:13:52Speaker 00

  Yep.

• 1:13:53Tim Ferriss?

  And it actually has some conflicts. So it's, it's not really an option to accept this.

• 1:13:58Speaker 00

  It's practical.

• 1:13:58Tim Ferriss?

  Yeah. Number two is to ask for something completely different, which is in fact, what we agreed to at the beginning, but they've already slotted all the other volunteers. So it may or may not be possible.

• 1:14:07Speaker 00

  Yep.

• 1:14:07Tim Ferriss?

  Or something in the middle, or, or I don't do it at all.

• 1:14:10Speaker 00

  The, the tim that I would know by default, in my opinion, knowing, you know, having known you for years is, uh, you'd say, I'm out. Like you guys, this is not what we agreed on. Time above all else. I want to be with high performers, work with things that are on point. This is just going south.

• 1:14:26Tim Ferriss?

  Yep. That, that is my instinct.

• 1:14:27Speaker 00

  Yeah.

• 1:14:28Tim Ferriss?

  But I really, there's the other part of me that's like, maybe you just needed to wait for your testosterone to decrease over time.

• 1:14:35Speaker 00

  It's a good exercise.

• 1:14:36Tim Ferriss?

  And you should try a different approach because there are times when I have cut off my nose to spite my face.

• 1:14:43Speaker 00

  Yes.

• 1:14:44Tim Ferriss?

  You know, out of principle would be the justification. And in retrospect, it's just like, what the fuck? Really? I mean.

• 1:14:50Speaker 00

  I mean, I'm all for principles, but principles tend to ignore nuances and other practicalities. And again, like the limitations of some people and organizations and constructs and industries and situations. Maybe the exercise is to go back and say, Hey, like this is not what we agreed on and you know, and you know, this, this is what will work for me, you know, can we, can we still make this work for me and give them like one more, you know, chance slash olive branch and see where it goes. But I also, on the counterpoint, believe that this sort of thing tends to be a repeatable pattern. And you probably know what you're in for.

• 1:15:32Tim Ferriss?

  Yeah, we'll see. I mean, maybe, you know, this surprised me. So maybe their response to the next one will equally surprise me.

• 1:15:37Speaker 00

  But hey, this postmortem, like this process, I mean, this is what develops muscle memory. This is what develops our, you know, our judgment.

• 1:15:45Tim Ferriss?

  And honestly, I, even though there's no clear resolution, I feel better about it just having walked through the kind of practical tactical

• 1:15:57Speaker 00

  Yeah.

• 1:15:57Tim Ferriss?

  next steps. So I don't have to hopefully pace around kind of shaking my fist at the sky for the weekend, which would be absolutely wasteful, right? Because even if I have the time this weekend, if I have no attention because I'm fixated on this and perseverating, that's a waste.

• 1:16:15Speaker 00

  And listen, I mean, I think it's a holy grail type of thing that this notion of can we compartmentalize our uncertainty, our fear, our anger in situations and somehow be able to allow the other 90% of our brain to opt to operate as if it weren't there. I mean, that's the gold standard. And I remember being on my honeymoon, two years into the start of my startup and thinking, gosh, like, how irresponsible am I? Like, I'm here in Thailand and my team is back grudging through it and we're this many months out of not making payroll and whatever else. And, you know, and yes, there was this part of me that was like, but this is your fricking honeymoon. And like, you get this once, hopefully. And, and you gotta like, at least be present for part of it. And I remember that was like, the beginning

• 1:16:58Speaker 00

  of my education on trying to compartmentalize that stuff. It's fucking hard.

• 1:17:04Tim Ferriss?

  Do you think that is a, is, do you think that is a, in retrospect, having had all your experiences since then? Has it worked well for you? I mean, would you recommend it? And it, yeah, and what does that really mean on a

• 1:17:17Speaker 00

  You know, I think it's, I think it's

• 1:17:18Tim Ferriss?

  On a cognitive level, or not necessarily mech, you know, mechanistically, but for someone who says, wow, Belsky sounds like a super chill at peace guy. There's this compartmentalizing thing that he first saw the light on, on his honeymoon. I should try that. What do they try?

• 1:17:33Speaker 00

  Sure. Yeah, I think it's, well, my attitude is that I actually admire people on both ends of the spectrum here. And I have less admiration for those in the middle, probably myself. On one side of the spectrum, you have those true pros that are able to just have all this going on. I mean, remember that story about Barack Obama, right as they were capturing or killing, you know, Osama bin Laden? And he was like at an event that night, you know, cracking jokes and whatever, knowing this was going on in the back. And you look at that, you're like, that guy must be a pro.

• 1:18:01Tim Ferriss?

  Yeah.

• 1:18:02Speaker 00

  How do you do that? And then, and then the other end of the spectrum, I admire people that are just like truly with their emotions and authentic. And they're like, these weren't the dates we agreed on. Sorry, deal off, like, don't call me again. Like, there's actually something about that that I admire from like a truth and emotionally connected governed way of living. It's in the middle where you're kind of, and I'm actually wondering now if it's sort of like the blackjack rule. You either always hit on 16 or you always stay on 16, but like, don't do it based on your emotions. Right. Don't be inconsistent. I mean, I definitely aspire to be more on the pro side, and that's kind of goes back to the do your fucking job thing I tell myself in my head sometimes. When I am feeling like I am going to sleep with this compartmentalized uncertainty or fear or anger or whatever.

• 1:18:45Speaker 00

  And it's just, okay, if you're a pro, like, you should be able to do this. And yeah, that's kind of what I tell myself.

• 1:18:53Tim Ferriss?

  Yeah. Well, it's, it also

• 1:18:57Tim Ferriss?

  Reminds me, and by that, I mean, your, your comments related to this is part of your contribution is like, suffering through might be too melodramatic, but tolerating

• 1:19:12Tim Ferriss?

  things that move more slowly, things that are a little more disorganized. That's part of your contribution with group X or person Y. And it, it makes me think of something that I haven't thought of in a while. That Robert Rodriguez, the filmmaker, said. When I was chatting with him on the podcast, and that was, he has film, like, I'm paraphrasing here, of course, and Robert, forgive me if I get it somewhat off, but filmmakers come up to me all the time and they're like, yeah, I was working on my film and I was doing this, but you know, this went wrong and like the lights blew out. And then we hadn't rented XYZ for the right period of time, even though I told them that we were supposed to do it, and then this, and this, and this, and they, they list off this litany of complaints. And, and Robert just says,

• 1:19:55Tim Ferriss?

  or he said to me, you know, they don't realize like, that is the job. Like, if you sign up to be a filmmaker, your job is that nothing is going to go right.

• 1:20:02Speaker 00

  And that is what you do. Right. And, and it's, it's almost like when you build a, not to bring everything back to product management, but when you build a plan, you either add one point, you multiply it by 1.1, 1.2, 1.3, based on what the team is, how part of the project is, how many unknowns there are, and that is your timeline. And I would argue that when you work with certain types of organizations, or you undertake certain commitments, you have to multiply it by a 1.2. Like, you're going to have a few misunderstandings and back and forth and one date change. And if you actually went into this knowing that that was the status quo, you wouldn't have been as upset.

• 1:20:37Tim Ferriss?

  Yeah, absolutely. Absolutely right. All right. So let's talk about the, the second bucket, optimize.

• 1:20:46Speaker 00

  Now that we made it through the first, and I have to say, like, endurance is not sexy, but it's just, we have to know we're not alone. These are important things to think about.

• 1:20:52Tim Ferriss?

  Definitely. So now that we're half naked and sitting in a sauna sweating together, let's get sexy.

• 1:21:00Tim Ferriss?

  Yeah. Where would you like to start?

• 1:21:02Speaker 00

  Where would I like to start? I mean, for me, All these, you know, these insights that I kind of cataloged into the optimization side, you know, fell in these camps of team self-product and, and I would just start, you know, on some of the team stuff. And this could be like whether you're just getting a few people to work with you, you're starting something as a solo entrepreneur, or you're actually leading a team. You know, I think one, you know, I would just start with the fact that, that we all know, you know, how important it is to be resourceful and not just rely on more and more resources to solve problems. I think it's pretty common knowledge that if you're constrained, it's a source form of creativity and there's a

• 1:21:41Speaker 00

  million stories about that. I like to think about, especially in the startup world, resources are like carbs. Resourcefulness is like muscle. It just, when you develop it, it actually stays with you and impacts like everything you do going forward. I think when you're bootstrapped for a period of time and forced to develop that muscle, that serves you forever. And of course, the stories of people raising way too much out of the gate and never developing that muscle typically actually don't end quite well. So when it comes to, you know, thinking about that, you know, a couple of thoughts. And, you know, one story is when I first hired our first kind of operations leader, a guy named Will Allen, from actually, he worked at TED conferences prior to that. And he came on board to, to kind of kick

• 1:22:26Speaker 00

  some operational prowess into how we were working as a company. And I remember every time teams would go to him saying, hey, we're growing, we gotta, you know, we need a bigger budget for web storage space, we need more people for this, for that function, whatever. Will would always say, you know, this had this mantra, refactor, refactor, then hire. And it was, and he just believed fundamentally that every team can go through one or two refactoring cycles. What do you mean by that? And what that means is, first of all, if it's a human head's perspective, it's like, well, like each person oversees one part of the product, could they oversee two instead? Are there any benefits to that? Should we cut some of the cruff? Like, are there people that we should shift around? Should we actually pick the feature that

• 1:23:10Speaker 00

  people are using the least and just kill it and take those resources and put it on this new thing? I mean, those conversations. Inherently don't happen when you have resources at your disposal. When you don't, they have to happen. And when they are, but when you have to choose between the two, it has to be forced, I guess, is my point. And, and that has become like a real actual principle for me as a manager and as a board member and as an advisor is constantly challenging teams to like find creative ways they can refactor and also making the case, even if they have the resources. That's why that benefits them.

• 1:23:44Tim Ferriss?

  You know, I was, I was just going to say that

• 1:23:48Tim Ferriss?

  one of the most valuable things that I've done in the last few years, which I should have started a lot earlier.

• 1:23:55Tim Ferriss?

  That I'm, I think I'm, I'm better at than perhaps the avoidance of emotional reactivities relates to anger certainly is journaling on hypothetical questions that constrain your resources, even if you have them.

• 1:24:08Speaker 00

  Interesting.

• 1:24:08Tim Ferriss?

  So if you have a year for say, a given project, a book, a competition, a campaign. All right, we have it scheduled for whatever it might be, right? A year, three months. What if we had to accomplish? What if we had to finish this? And it might mean that the metrics change in one week.

• 1:24:27Speaker 00

  Yes.

• 1:24:27Tim Ferriss?

  Right? What if we had to finish this? And we couldn't personally as a team, touch it. You had to outsource all of it. Hey, would that simplify the specs? Would that simplify what you submit? All right. And then does that end up being usable by the team? And I apply it to time, any currency I can think of, right? Headcount. If one person had to do this, how would the description of the project need to change? If we had to do it with X amount of dollars, which is one tenth what we're budgeting. Absolutely had to. And write down how that would change the implementation. Without fail has made every project I've applied that to dramatically better.

• 1:25:05Speaker 00

  By the way, I mean, it's true on the individual level, on a small team level. There's also a company, a company called Skybox that was started by four Stanford students. They, they decided that their goal was to build a satellite with off the shelf parts. At a time when satellites cost hundreds of millions of dollars. And they were like, they were like off the shelf parts. That is the ultimate. And that was the fuel of innovation. They ended up building satellites between two to five million, which is a fraction, right, of what satellites were being built for. And at this and then like a year or two later, Google acquired them because of their innovation in the space of economically and resourcefully building something that was otherwise out of touch.

• 1:25:49Tim Ferriss?

  Yeah, that's a great story. For people who want to want to hear or read a great story of resourcefulness, this just reminded me, and somebody else is gonna have to look this up, but there was a robotics competition. You might have have heard of this or seen it. A feature film was made out of the story and I will put it in the show notes, guys. But a feature film was made depicting this, telling the story of these low income, at risk youth who were encouraged to join a robotics team. I want to say it was in Los Angeles by this incredible professor. And they, I don't want to spoil the story, but

• 1:26:31Tim Ferriss?

  the the narrative and the journey is really the payoff, not the the end, which is easy enough to figure out.

• 1:26:38Speaker 00

  Yep.

• 1:26:39Tim Ferriss?

  But they were competing against these very well healed, upper class, perfectly educated teams, and they had to scrap by with essentially no budget.

• 1:26:51Speaker 00

  Yeah.

• 1:26:51Tim Ferriss?

  To learn and build robotics to compete underwater. And it's just such an amazing story. And I also remember Jack Ma of Alibaba at one point, and I might get the order slightly wrong, but he said, we had a number of advantages when we began. We had no strategy, no money, no experience.

• 1:27:11Speaker 00

  Right.

• 1:27:13Tim Ferriss?

  And

• 1:27:14Speaker 00

  It's a common story.

• 1:27:16Tim Ferriss?

  Yeah.

• 1:27:16Speaker 00

  And it's it is counterintuitive. And even if you benefit from that, you actually still start to operate differently when you start having the resources at your disposal. The same thing, by the way, goes for hiring. You know, another thing that, you know, I've observed in many instances is Initiative being more important than experience.

• 1:27:35Tim Ferriss?

  Yeah.

• 1:27:36Speaker 00

  And you're hiring people and you could be, when you have the resources, you tend to become a resume snob. And you're like, oh, I'm gonna have a VP of this Google or whatever. But when you don't have the resources, you actually have to hire for something else because you can't afford to hire those people. And so you start to measure people based on, well, are they the type of person that takes initiative on anything they're working on? Like, what's their history of doing that? And will they continue to do that here?

• 1:27:57Tim Ferriss?

  What does initiative mean in this case? I have an image in my mind because that's something I look for.

• 1:28:03Speaker 00

  To me, initiative, it's, it's really, it's when you're genuinely interested in something. Do you take relentless, persistent and continuous action? Is it something that you, you, you hold your eyes up at night to do more of? Versus are you, are you confining yourself to the job description?

• 1:28:19Tim Ferriss?

  Yeah.

• 1:28:19Speaker 00

  So in some of it, some of, I always like to say, like, I feel like so much of the future is, is done by people doing work they didn't have to do.

• 1:28:26Tim Ferriss?

  Yeah.

• 1:28:26Speaker 00

  And if that's true, it's really about people who take initiative over like what they believe their job is, which basically comes from having a lot of experience. You start to become a little bit more confined because hey, you've been down this road before, you've seen it 10 times, like, let me do my thing.

• 1:28:40Tim Ferriss?

  And by the way, I had three assistants at Google, so which three assistants are you gonna hire for me?

• 1:28:44Speaker 00

  I haven't written code in a while, but hey.

• 1:28:46Tim Ferriss?

  Yeah, but the, you know, what jumps out to me, and I, I've hired far fewer people than you have, but looking for

• 1:28:56Tim Ferriss?

  deep examination of the tasks they're given has proven really valuable. So if I find, if I, which displays a lot of qualities at once. So if I give them something really quickly, because I'm in a rush.

• 1:29:09Speaker 00

  Yeah.

• 1:29:10Tim Ferriss?

  But it's important and I say, all right,

• 1:29:13Tim Ferriss?

  off the cuff, I imagine we're gonna do A, B, and C. And then as, as the final step, you're gonna have to choose between one, two, three.

• 1:29:19Speaker 00

  Yep.

• 1:29:20Tim Ferriss?

  And if someone comes back and says, I looked into all of that, but I think the better option is number four, and I actually tested this out.

• 1:29:26Speaker 00

  Yes.

• 1:29:27Tim Ferriss?

  And although you didn't ask me to do this, you know, on my own time, I did this. It's like, okay, that's

• 1:29:32Speaker 00

  Initiative.

• 1:29:33Tim Ferriss?

  That displays initiative.

• 1:29:34Speaker 00

  Yes.

• 1:29:34Tim Ferriss?

  It also displays an understanding for the circumstances I was.

• 1:29:39Tim Ferriss?

  Experiencing buried under suffering from when I gave the order.

• 1:29:43Speaker 00

  Yes.

• 1:29:43Tim Ferriss?

  They're always asking, is this, what is the outcome? And is this actually the best route to that outcome? Uh, and by observing that in other people, I've become better at it myself.

• 1:29:56Speaker 00

  Yes.

• 1:29:57Tim Ferriss?

  Which is, uh, which has been a huge key learning for me. And, uh, this is, this is meandering quite a bit, but that is, that is my way.

• 1:30:05Speaker 00

  It makes sense.

• 1:30:05Tim Ferriss?

  That also, I mean, you, you, by, by observing other people, you can improve those qualities in yourself. If you really pay attention and also reviewing what they've done.

• 1:30:16Tim Ferriss?

  And vice versa, right? You have to lead by example. So hopefully you're doing the same thing. And, uh, you know, similarly, when we're talking about anger and these other emotions, I've realized that when I'm having difficulty with a particular emotion myself, if I can step out of my inward focus, the me, me, me focus, and try to help someone else with a challenging emotion, ideally a similar emotion. It gives me the observer status, the objectivity to help them. And then I'm like, huh, never would have come up with that.

• 1:30:48Speaker 00

  Yes.

• 1:30:48Tim Ferriss?

  If I were thinking about my own problem because I'd be too wrapped up.

• 1:30:50Speaker 00

  What's the Carl Jung quote, uh, you know, that understanding the darkness in others is, or understanding the darkness in you and others is like transferable, right? Like all of these insights we get. Yeah. And, and I think the other piece here is just that don't measure initiative based on like stuff within the field you're hiring the person for. Like recognize that initiative is transferable, that past initiative is the best indicator of future initiative. And be a little liberal with like, you know, how, how directly applied it is. I mean, a couple of the things on the, on the, on the assembling the crew front, um, that I, it was kind of struck by that kind of made it to the cut at the end of these insights, you know, one of them is hiring people who've endured some form of adversity.

• 1:31:31Speaker 00

  And another one is hiring people with whom every conversation you have with them is a step function more interesting than the one before it. On the adversity front, you know, super quickly, um, uh, Tristan Walker, who's an entrepreneur, you know, started Walker Brands and, and has, has built a real business. Um, yeah, he talks about how, um, he, uh, he grew up, he had a tough upbringing and he feels like one of the things that he really carried from his upbringing was courage. And he feels like he wanted to make that a true value of their company. And I asked him, like, why is that? It sounds nice, but why does that really mean? And he said, only with courage can you practice the same values consistently.

• 1:32:09Tim Ferriss?

  So true.

• 1:32:09Speaker 00

  Yes.

• 1:32:10Tim Ferriss?

  Yeah, it's like the meta prereq.

• 1:32:11Speaker 00

  Sure, because otherwise you're always making exceptions, you're always deviating. But if you have courage, you will take on and be consistent. And so I was like, well, then how do you hire for that? And he was like, hey, I look for people who went through shit like I did. And, um, and it was interesting, you know, that, that lends into why adversity actually is important when it comes to building like a great culture and actually a product and brand and everything that's consistent. The other, the other, you know, one brings me back to the story of working with the Periscope team. So this is a team that was building a live streaming application, um, back in the day when, uh, actually there were Snapchat and other products that were more about facials and whatever, but, uh, yeah, not facials.

• 1:32:51Tim Ferriss?

  That's a different. Photographs.

• 1:32:54Speaker 00

  We're in the sun. Yes, so, um.

• 1:32:57Tim Ferriss?

  Selfies.

• 1:32:58Speaker 00

  Selfies. Yes, it's the heat, I'm telling you.

• 1:33:00Tim Ferriss?

  It's hot, it's hot in here.

• 1:33:01Speaker 00

  So.

• 1:33:01Tim Ferriss?

  It's so hot.

• 1:33:02Speaker 00

  We'll have to take a quick break in a second.

• 1:33:03Tim Ferriss?

  My thermometer has been broken for the last.

• 1:33:04Speaker 00

  And this mic, I can barely handle anymore, but anyways. But, you know, it's, uh, so when I met with that team and, um, they were doing some things kind of different. They were saying, hey, even though every real time video thing is more about selfies and showing what you're doing to others, like, we believe it's actually about seeing the world through someone else's eyes. They had a lot of things like that. But what really drew me to them was every kind of, I had a conversation with Kavon and his co-founder Joe, it was always like a step function more interesting than the one before it. And I remember juxtaposing that with most conversations I have that are sort of replays.

• 1:33:36Tim Ferriss?

  By step functioning, you mean dramatic improvement in this case?

• 1:33:38Speaker 00

  Dramatic improvement, difference, and every conversation being like, whoa, new level, new plane, new plane, new plane. And, um, and then now, having gone through that investment from the whole period of seed through product, product fit through acquisition by Twitter, I think one of my, one of my beliefs is that it was that, um, chemistry with them that actually kept me engaged and also kept their team engaged with them. Like, it was just one of those traits, again, that I actually tried to look for. So I actually tried to meet candidates for senior roles twice. And I tried to do a delta comparison between the first conversation and the second. And oftentimes it's the same. And people are like, why am I here again?

• 1:34:16Tim Ferriss?

  I answered these already.

• 1:34:17Speaker 00

  Yes.

• 1:34:17Tim Ferriss?

  And I haven't done any additional digging.

• 1:34:19Speaker 00

  But sometimes it just goes in a completely new direction. And you're like, you know what? Everyone who works with this person is going to want to keep working with them, and so will I.

• 1:34:27Tim Ferriss?

  So in the interest of keeping you working with me as a friend, I think we will take a cool off break, and we will be back.

• 1:34:34Speaker 00

  Tout à l'heure.

• 1:34:38Tim Ferriss?

  And here we are back in the whining cylinder in the truth barrel. And I thought we might chat about, now that we've lowered our core temperature just a wee bit.

• 1:34:50Speaker 00

  A wee bit.

• 1:34:50Tim Ferriss?

  A wee bit. Since we've been, I think, incorporating a discussion of self in the discussion of team quite a bit, that we maybe segue into some self-specific points, meaning a point or two. And then what a lot of people would love to hear about, because you're so known for it, I think, is product. And then we can move from there, see where the wind takes us.

• 1:35:17Speaker 00

  Yeah. Yeah, I mean, on the, on the, um, yes, you have to optimize how your team works. And there's, you know, process improvements and blah, blah, blah, blah. There's also, though, the harder challenge in a bold, you know, venture or journey of optimizing the way you work and think and react and everything else, which we've talked about a little bit, I think. You know, one, and one, um, you know, one of the, you know, little, little insights that I thought quite a bit about was the fact that your, um, your true blind spot is, is how you appear to others. And I think that, you know, part of that is, is, um, is understanding, you know, that

• 1:35:56Speaker 00

  we, you know, we react, obviously, for all different sorts of reasons to things. You know, we react based on our, uh, the confidence we have from the financial security we may or may not have. We react based on all sorts of other factors, um, when it comes to just an altercation at work or a decision that we make or whatever else. And knowing that, then of course, everyone else, you know, interprets us as re, as, as sometimes irrational to their context of where they're reacting from and what their background is and whatever else. And this is about surfacing, uh, what some of those, um, what, what, what are the things that we're doing that we don't even realize that other people see and, and scratch their heads kind of thinking about?

• 1:36:38Speaker 00

  I remember this, uh, this, um, experience I had in high school where I lived on a farm in Vermont for six months. It was one of those programs you apply to and it was 45 kids on a farm, self-sustaining. And it was a real like, it was more about community than the farm, frankly, learning how to coexist within a small group and govern yourselves and that sort of thing. Kind of like Lord of the Flies.

• 1:36:58Tim Ferriss?

  How old were you?

• 1:36:59Speaker 00

  Uh, junior year of high school.

• 1:37:01Tim Ferriss?

  Were you piggy?

• 1:37:03Speaker 00

  Potentially. Um, and, uh, super thin, but yes. Um, but I, uh, but, you know, one of the, one of the intense, most intense exercises that we did towards the end that I will never forget is this thing called the mirror exercise where you paired up with somebody and they would tell you what they saw. Of course, from their experience, having lived with you 24/7 in a farm in Vermont. And, um, you know, and it wasn't a physical thing. It was like, what, I see you afraid, or I see you're supposed to use verbs. You know, I see you, uh, sometimes wondering, you know, if you, if you are in the right place, or if you have the right to speak, or, you know, there were just all these different. And I remember it hit me

• 1:37:45Speaker 00

  like a ton of bricks. I actually wish I remembered exactly what the feedback was that I got. What I would think it was, was that I had a lot of insecurity.

• 1:37:53Tim Ferriss?

  And to pause, just so I understand the format. Did you have one person who would give you five examples? Was it a line and you had one person or each person give you one item? What did it look like?

• 1:38:05Speaker 00

  Yeah. So it was, um, you paired up with a few different people. I think you had 10 minutes and, um, you were doing it for each other. And the challenge was to not, it's, it wasn't out of judgment. It was more like you were supposed to see what you were just kind of, you were supposed to share what you were seeing without really imposing so much judgment around it, which is hard. I mean, because some things sound judgy, but, um, but it was, uh, it was, you know, I think it was a, it was a heartfelt exercise. And, um, what it, what it did is it, what I do remember taking out of it was, gosh, people see things that I don't, I didn't realize I either showed or knew, or didn't even know about myself. And, um, And so, you know, from that, I started to, in my professional experiences and in my

• 1:38:49Speaker 00

  personal experiences, I would often ask the question of people I'm with, like, if, if, you know, if you were me, what would you do? You know, I would try to kind of get someone else's take on a situation from a different set of, again, those things that are the context of our decisions, the background, the struggles, the issues with your parents, all the other stuff, like, assuming everyone has a different thing. If you ask that question to other people and you see a delta between your reaction or your thought and theirs, then you actually at least know there's something to explore there. It's almost like a canary in, in the fact that, okay, hey, there's some projection going on here, there's, there's some blind spot that I am not fully aware of that is interesting.

• 1:39:31Tim Ferriss?

  Right. Yeah, you're looking in the mirror, but like you said, I mean, the blind spot, very literally like a car where there's just this empty pocket that you cannot see.

• 1:39:40Speaker 00

  And then the question is like, how do you fish it out? Like, it's super hard because it's literally not in your mirror. So.

• 1:39:45Tim Ferriss?

  Have, well, a few questions related to that. First, to the exercise, is there anything, and it's a long time ago, I realize, that the counselors or leaders of the group said to everyone so that they would receive

• 1:40:01Speaker 00

  Yes.

• 1:40:01Tim Ferriss?

  without becoming defensive?

• 1:40:04Speaker 00

  Actually.

• 1:40:04Tim Ferriss?

  Which would be the natural response for a lot of people, myself included, probably.

• 1:40:08Speaker 00

  Yeah, it's a good question. And I think that it reminds me of like one part of it that I admitted, which was that we were also instructed to really only, at the end of the day, think about the ones we heard more than once.

• 1:40:18Tim Ferriss?

  Hmm.

• 1:40:18Speaker 00

  So.

• 1:40:19Tim Ferriss?

  Could you pass me your water now that I've extinguished mine?

• 1:40:21Speaker 00

  Yes.

• 1:40:22Tim Ferriss?

  And I will selfishly put my self preservation ahead of yours. Please continue.

• 1:40:25Speaker 00

  Niagua, suagua, in your casa. But, you know, I think that, um, that was, it was somewhat, um, because, you know, you know what that direction did? First of all, it made people realize that if I tell someone this because I'm judging them and they don't hear it from others, like, I'm gonna look like an idiot. So it had a preventative measure in that sense. It also helped the recipients discount anything that they heard once. Maybe it's psychologically still hard to do it.

• 1:40:50Tim Ferriss?

  Very helpful.

• 1:40:51Speaker 00

  It was a very interesting trick.

• 1:40:53Tim Ferriss?

  Have you ever done a, experienced a 360 interview? Okay, so for Reviews, you mean, right? Yes, 360 review, sorry. 360 review, now it's my turn to Yep. Turn my brain into scrambled eggs. And for those people who don't know, this is something a number of my friends have experienced, which I didn't realize until I did it myself and felt like a broken human being and was hit so hard that I wanted to confess that to close friends. And they're like, oh, my God, yeah, man, you're telling me. And I don't want to mention names. I mean, people that are very people you would view as

• 1:41:32Tim Ferriss?

  maybe not immune to criticism, but certainly these like stalwarts of strength, these like monolithic pillars of resilience. And what a 360 review entails for people wondering, it's something I would recommend to everyone, actually, and there are ways that you can do it outside of a business context. But what it generally entails is someone wants to figure out these blind spots. Yep. Figure out how they're being viewed, figure out what their better behaviors are, what their lesser behaviors are, et cetera. And you will select with the person who will be doing the interviews, it's not you, say peers, people you report to, people who report to you.

• 1:42:17Tim Ferriss?

  Yep. And so on and so forth, maybe suppliers, distributors, who knows? People you interact with a fair amount. And it's, it can be a very sophisticated process. You can do this, I actually did a very early version of this, it was really truncated in high school, because I wrote a book called Mental Toughness Training for Sports by Jim Leher, L O E H R, who's in the last two years become a friend, which is crazy and awesome, really fantastic guy. Works with a lot of athletes, but it has an inventory that you're supposed to give to coaches, peers, teammates, people who know you really well. And it made a huge difference in my success as a wrestler.

• 1:42:57Tim Ferriss?

  It was really remarkable just to see from like the day of receiving answers, which I received myself. Yep. To the next day, it was really astonishing how much things changed. And with the 360 interview, though. Yep. Just to come back to this.

• 1:43:13Tim Ferriss?

  Only pay attention if it comes up more than once. It's a very hard exercise, even if you prepare yourself, at least in my experience and the experience of some of my friends, to take because you're seeing these ugly truths, especially the ones that come up more than once. You're like, alright. Yeah. And the answers are anonymized, which gives people another layer of permission to be particularly direct. And one thing that came up for me, and it's actually the only thing that I remember because I literally could not read this document. I mean, I went through it once and I was like, I can't actually psychologically digest all this right now. But I did pay attention to a few things and one that came up a lot, and then I want to, I want to come straight back to you.

• 1:43:57Tim Ferriss?

  But this, this may be helpful for other people if they choose to implement something like this, even with their friends and they know that they're doing. Just look up 360 review and you'll find all sorts of resources. I've never seen Tim fully celebrate anything. And it relates back to what I mentioned earlier, that's always looking for what's wrong. The good stuff takes care of itself. We're only doing our jobs. I'm only doing my job. Why would I pat myself on the back for doing something that I signed up to do? Yes. It would be a disappointment not to do it. I don't get extra credit for completing something. And that became so severe and maybe it relates to a lot of other stuff that I'll talk about another time, but feeling damaged or in some way flawed

• 1:44:37Tim Ferriss?

  or undeserving of that. But I, in retrospect, very painful pill to swallow, but they were absolutely right. I mean, it's crazy to think, but at, at a certain point, and I don't expect anyone to cry me a river on this stuff, but it does belie some type of real psychological issue that I had to address. But I remember the last two times I've had a book do very well on the bestseller lists. I mean, when, like the first time it happened, like game changing, collapse against the wall, fall on the floor. I can't believe it. Dazed for the rest of the day, maybe the rest of the week on cloud nine. And at this point, I feel like it's the expectation that my books will do that. Certainly it's the expectation of the publishers. Yep. And it's, it's just relief that I didn't fail.

• 1:45:22Tim Ferriss?

  And maybe I'll have one drink and then it's like, alright, on to whatever you should be doing next. That's awful. So.

• 1:45:30Speaker 00

  It may be good, I mean, obviously, from a, you know, most great product people are perpetually dissatisfied with their product. But it is, I mean, first of all, you know, yeah, it's not good for your own psyche. But for people around you, you know, they can start to see that as also, you know, a form of arrogance. Or, you know, in some ways, you're getting a gratification that most people will never be able to get. And then they're seeing you not acknowledge it. It's interesting. Again, like back to that mirror exercise, unexpected things you might see.

• 1:45:58Tim Ferriss?

  Yeah.

• 1:45:58Speaker 00

  That people see.

• 1:45:59Tim Ferriss?

  Yeah, for sure. And also, I mean, at least in my own reflection,

• 1:46:07Tim Ferriss?

  the voice in my head that has been in my head that we assume to be us is very often for me, not my voice at all. It's the, it's the maybe hypercritical voice of other people I was around.

• 1:46:19Speaker 00

  Yes.

• 1:46:19Tim Ferriss?

  And have adopted, but I'm playing their soundtrack.

• 1:46:22Speaker 00

  Yes.

• 1:46:23Tim Ferriss?

  I did not decide to have that voice. And

• 1:46:29Tim Ferriss?

  also realizing that how I talk to myself, even silently, is very often how, even indirectly, I end up communicating with other people, even if it's just through body language or implied. And, you know, you can help other people to help yourself, or you can help yourself to help other people. But, uh, super, super valuable. So I'm glad you brought up the exercise. And I'm gonna, I'm going to publicly, on the podcast verse,

• 1:46:57Tim Ferriss?

  I'm going to suggest that we tap out and go sit outside where it's cooler.

• 1:47:01Speaker 00

  Thank God, man. I was gonna, thanks.

• 1:47:04Tim Ferriss?

  So we are going to segue.

• 1:47:05Speaker 00

  I don't have the physique of Tim, for those who can't see.

• 1:47:07Tim Ferriss?

  Doesn't seem to help with my, my heat talks. So we're gonna, we're gonna keep recording and just walk out.

• 1:47:14Tim Ferriss?

  Would be helpful to have a temperature gauge of some sort, which we do not have. And now we're outside, so you'll get to listen to the wildlife in the middle of the night in the countryside, which is nice.

• 1:47:25Speaker 00

  Stars.

• 1:47:26Tim Ferriss?

  Stars, fire pits, so we can.

• 1:47:28Speaker 00

  This will be the third setting.

• 1:47:29Tim Ferriss?

  This will be the third setting. We're doing a lot of, a lot of costume changes and a lot of scenery shifts.

• 1:47:36Speaker 00

  This is good. This is good.

• 1:47:39Tim Ferriss?

  You know, I think that crickets, insects and birds at night is a perfect setting for product talk.

• 1:47:47Speaker 00

  My favorite topic.

• 1:47:48Tim Ferriss?

  Where shall we begin?

• 1:47:50Speaker 00

  You know, I think that product, and when I use product, I mean, any kind of customer experience you're crafting, whether it's a service, an in-store experience, if you're a retail store owner, or a digital product, right? And I think that there's some big, counterintuitive and strange ironies in how we craft products and experiences for people. First of all, we have way too much faith in people unearthing the value of what we're building. And what I always like to remind myself and teams that I work with is that in the first

• 1:48:29Speaker 00

  30 seconds of any experience of a new product, service, experience, whatever, every customer is lazy, vain, and selfish. They're lazy in the sense that they don't want to read anything, they don't want to watch videos, they don't want to try to figure out how something works. They're vain in the sense that, you know, let's all admit, we all have ego, we all want to feel good about ourselves, and something that makes us look better to ourselves and to others feeds that, and I don't think any of us are immune from feeling that to some degree. And selfish in the sense that, hey, I have so little capacity and I want to look, I want to achieve a lot very quickly.

• 1:49:10Speaker 00

  An example on the selfish side is products like Stripe, or Twilio, or others that kind of appeal to developers with, hey, two lines of code as a way of them adopting that technology, because it was just like, hey, selfish, like, I'm going to get this done quickly. I don't even care if it's as good as like the homegrown solution. And vanity comes across in every consumer product you see with those ego analytics, those hearts, those things that tell you that, oh, wow, like, it's working, I want to do this more. And of course laziness, you see with every onboarding of every product we go through. And so with that-

• 1:49:47Tim Ferriss?

  Onboarding, meaning the signup process.

• 1:49:48Speaker 00

  Exactly, like the signup process, or walking into the store, knowing, when you go into any product experience, why are you there? Where do you go next? What's possible?

• 1:50:01Speaker 00

  Now, the pushback I get from a lot of great companies and teams or whatever is, "Hey, I have more faith in people. They're going to figure out why this product is great. I can appeal to them with this long-term value of what they have to contribute." I mean, you look at a product like Pinterest again, which was really ultimately a network of discovery, but their appeal in the early stages of their business was just make a quick collection that's visual as opposed to delicious, which was just links. So they appealed to that immediate need of, "I want a collection for myself," before recognizing the value of other people's content. And there's so many examples of teams. Another product thing I think a lot about is back to that onboarding first-time user experience.

• 1:50:46Speaker 00

  Should you make a video of how to use your product? Should you walk people through and tell them, make them read something? Or should you just do it for them? And a lot of products that really do succeed quickly actually give you a template. They just actually do it for you. They make you seem so much better than you are with stock content or whatever it is. So those are just a few examples around the edges. But to me, it's a product principle that makes the case that we have to spend a ton of time on crafting that first-mile experience for our customers.

• 1:51:17Tim Ferriss?

  How do you stress-test, say, a first design after you've, assuming the team has accepted those commandments or those realities, and they think they've designed for it? How do you stress-test it?

• 1:51:32Speaker 00

  Well, there's a few. First of all, the classic metrics of are people getting their way through? What's catching them up? I remember in the Behance days, we had a terminology for the creative field that you're in called realms, and we realized people didn't understand what that meant. And so that was an insight in the first-mile experience that drastically improved conversion, little things like that. But I think that, but it really comes down to empathy with the newest user.

• 1:52:02Tim Ferriss?

  Are you bringing people in and watching them on a computer? Or are you using a...?

• 1:52:10Tim Ferriss?

  Contracted service, some type of online service to record Craigslist. What are you doing?

• 1:52:15Speaker 00

  All of the above. I think great teams, first of all, don't outsource this completely. They recognize that only being shoulder to shoulder with their newest customers, and I'll get to the newest customer, why I keep saying that in a second, is crucial because you're kind of feeling the anxiety and the pain where a report or some graph will never really tell you.

• 1:52:39Speaker 00

  And yeah, I think that there's a lot of mechanisms to measure the effectiveness of a first mile. The thing is, though, it's actually not as simple as just solving it. Like, once you have a new product in the world, and call it Twitter, right? You launch Twitter and you appeal to a group of users that are actually willing to build their timeline, follow all the accounts, and over a period of time have a great experience. That is a cohort of new users. Then, word gets out, people start to use Twitter who kind of come for the news as an alternative to CNN, and they're hit over the head with this idea of building your timeline, following accounts. And they're like, "What? I don't have the tolerance for that."

• 1:53:21Speaker 00

  And in this instance, think about it, like, they could have nailed their first mile and had tremendous growth, and then suddenly, the newest cohort of new users isn't even willing to go through it, and they have to completely kind of reinvent the first mile experience of their product. Which is why teams have to continually reinvent that first mile. It's not like you get it right and then it's like move on, which actually, most teams do.

• 1:53:46Tim Ferriss?

  And so that then relates to the newest customer, paying attention to the latest cohort? Is that, that's the reference?

• 1:53:54Speaker 00

  Yeah, it's consistently committing period of time to understanding who the newest customers are. I mean, think about it, the newest ones are, the first ones you ever have when you launch a product are super forgiving. They're early adopters. The next round, you know, they're actually like a little bit more about this better be professional, this better be reliable, but they're willing to go along with some bugs and whatever. Eventually, you get to those kind of pragmatists, right? Later in the curve. And you... Now, the other problem that a lot of teams have is that when they're launching their product, let's just talk about the newest of the new users when you first launch a product. Oftentimes, ironically, the last mile of their experience building the product is spent on the first mile of the customer's experience of the product.

• 1:54:38Speaker 00

  So it's sort of like you're done with building a product after two years or whatever. And it's like, oh shit, we gotta make a tour. And oh, what should the default be when customers come in? Our friend Dave Marin, who's another great product thinker, always likes to say the devil's in the default. Whatever customers see first, they're just gonna stick with forever. That kind of decision can't be made like right before launch. In fact, that's the most important decision you're gonna make.

• 1:55:03Tim Ferriss?

  Yeah, yeah, definitely. What advice do you give to entrepreneurs when they have, say, two or three products that they feel torn between and they don't know which direction to go in? And they say, I really feel like we would be equally happy

• 1:55:19Speaker 00

  Yes.

• 1:55:20Tim Ferriss?

  doing A or B, but once we commit, we know we're going to be on this path for a good chunk of time and it's gonna chew up a lot of resources.

• 1:55:29Speaker 00

  Yeah.

• 1:55:29Tim Ferriss?

  How do I choose?

• 1:55:32Speaker 00

  Well, I think that there's two answers to that. You know, one is you print out comps for both, like designs, and you put them in front of customers and you're sort of getting a sense of

• 1:55:41Tim Ferriss?

  Comps meaning mockups?

• 1:55:42Speaker 00

  Yeah, mockups, sorry. And you test and you build some of the marketing copy, like welcoming. You just give like a design and experience, a fake experience, and you test that and you gauge what sort of approach to this problem resonates with people. You know, I think that a common mistake at this phase is that teams decide to focus on the thing they're most passionate about solving or the solution that they're most passionate about, rather than seeking more and more empathy with the person suffering the problem. And so you'll be like, oh my God, this is the best solution. Like, I'm so passionate, let's do it. Which is why I always actually say that empathy is more important than passion when it comes to like figuring out what product you should actually do.

• 1:56:25Speaker 00

  Also, on the question of how you determine which product to build when your team comes together and you're trying to solve a problem. Listen, there's a lot of talk about the notion of a lean startup and getting an MVP or a minimum viable product out there and testing. I mean, that's another answer to your question, right? Not only do you make up mockups and show people and test out the marketing copy and the value proposition of what you're building, yes, put out a product and see how it performs. But the problem with that, that teams, I think, run into is that whatever you ship ends up having more sticking power for your own team's approach and becomes a bit of a local maxima of what you're able to do after. So this notion of,

• 1:57:09Speaker 00

  hey, we'll ship a minimum viable version and then we'll just iterate to a great place.

• 1:57:15Tim Ferriss?

  So what was the word you used?

• 1:57:18Speaker 00

  Local. Local maxima.

• 1:57:19Tim Ferriss?

  Basically, you're anchored.

• 1:57:21Speaker 00

  You're anchored, right.

• 1:57:22Tim Ferriss?

  To that version of the product in some way.

• 1:57:24Speaker 00

  And whatever iterations you say you're going to be able to do to actually get to that elusive product market fit where suddenly customers are getting the value out of it enough to tell their friends, it actually may get harder to get there when you're not willing to do very bold strokes. And so I think in an ideal world, you do some testing before you start building of just the idea, showing the mockups, the stuff we discussed earlier. But then you build something that you truly believe has a shot at adding that or delivering that value to customers and take the extra time to perfect the few differentiating factors that are like most special about it. Yes, you can cut corners around all the

• 1:58:06Speaker 00

  other edges, but you don't want to ship the minimum viable version of the thing that you're going to be known for because that's not going to test whether or not the conviction you have is the right one.

• 1:58:18Tim Ferriss?

  And the minimal viable product also is, at least in my mind, and I'm sure I'm missing plenty, predicated on a number of different things. It is much more appropriate for software than many other types of products that you might ship because it can be, at least at this point in time, not always the case, but iterated and updated remotely. Second, even within software, it applies most, I would say, to products that are

• 1:58:50Tim Ferriss?

  A unique solution to a pressing problem. People will put up with a lot of bullshit and a lot of bugs and a lot of heavy lifting. If you are the only option.

• 1:59:03Speaker 00

  Yes.

• 1:59:04Tim Ferriss?

  But if, on the other hand, you are, say, a newsletter of a certain type. Or you have, in fact, a very attractive market, but also very competent competition.

• 1:59:18Speaker 00

  Yep.

• 1:59:21Tim Ferriss?

  That approach may not always be.

• 1:59:24Speaker 00

  Yeah.

• 1:59:24Tim Ferriss?

  The best approach.

• 1:59:25Speaker 00

  The minimum viable experience of a restaurant may not go so well. And, you know, but at the end of the day, you also don't need to get everything right to launch.

• 1:59:36Tim Ferriss?

  Right.

• 1:59:36Speaker 00

  Or to open your doors. What you do need to get right is the thing you're going to be known for. The last thing I would say on the product side.

• 1:59:43Tim Ferriss?

  Yeah.

• 1:59:44Speaker 00

  Is, is actually, let's talk about, you know, another mutual friend of ours, Garrett Camp, who is a co-founder of a number of different companies. And, and, and actually now.

• 1:59:56Tim Ferriss?

  Including some big ones.

• 1:59:57Speaker 00

  Including some big ones, like Uber. And he, you know, and one of the things that, that I have learned from him over the years, and I've seen in some other, you know, serial successful founders, is this notion of building the narrative before the product. So, and we were just talking about which product do you choose? Sometimes it actually helps to say, hey, what is, what, what should the splash page be and what should the brand be before we even get the team together? I mean, yet alone start building something or coding something in a digital sense. We talk about the notion of product market fit, right? When, when customers are getting the value, we talk about the notion of product founder fit, when you find the right team to build something.

• 2:00:41Speaker 00

  But what about product brand fit? What about making sure that you have like something that's piercing? I remember when Garrett was thinking about Uber originally, when he was still just CEO of his company, Stumble Upon, and he was kind of drafting out the concept of Uber. And, and I remember him obsessing over the icon.

• 2:01:03Speaker 00

  Yeah, like the logo before there was even a team or a CEO on this project. I also remember him agonizing over this notion of, hey, is it, is it an aspirational brand, like everyone's private driver? Or is it an accessible brand like taxis on demand? Right? And I mean, and if you think about that, it's like, wow, like, these are questions that he was asking before this was, this technology was even coming together or even validated, right?

• 2:01:33Tim Ferriss?

  Yeah, Carrot is a, is a very exceptional human and founder who, who really telescopes out very, very far in the earliest stages. And I remember getting one of the very, very early mockups. This was, this was before the app was deployed, even with one car. The screenshots, you know, these, these comps, as you mentioned, the, the, the looks like model in a number of graphics that he sent to me and the streets were in the Netherlands. And I was like, wait, what? In the Netherlands?

• 2:02:16Speaker 00

  He was thinking global already.

• 2:02:19Tim Ferriss?

  He was thinking global.

• 2:02:20Speaker 00

  But it's also, it's also though, I've, I've had conversations with him about brands for other companies that he's, you know, been working on and, and he'll say, he's really all about buying great domain names, as you know, and coming up with a great, pithy, hopefully four-letter brands. And, and I asked him about that in the process of putting the book for The Messy Middle together. And he was saying that it's also about what kind of email address the team that you put together will actually want to have. I was like, email address? Like, why does that matter? He was like, would you rather have a, you know, [email protected]? Or would you rather have [email protected]? You know, and, and so he was also thinking about from like the product brand fit perspective,

• 2:03:04Speaker 00

  is this something that people can grow into, that people would want to work out at and say like, I, you know, this is my email address? So I just, I've always been. Fascinated by the fact that he develops this narrative and like that brand development piece even before the product and in some cases the team itself. And again, back to that question you originally asked of which product do I build? Where do I start? Which I get from founders all the time. I actually like to say, and I even do this internally in my day job at Adobe now with new products that are being developed around the company. Put together the splash page. And it's like, well, I don't even know what it's going to be called yet. I don't know what the brand will be. I don't know what the slogan will be. I don't know what the and it's like, yes.

• 2:03:45Tim Ferriss?

  That's the point.

• 2:03:46Speaker 00

  That's the point. Like, put that together as a starting place because it, you know, it helps get alignment very quickly, which is a magical part of product development is when you have alignment versus not two different, two different ballgames.

• 2:04:00Tim Ferriss?

  So you look at that chapter one and then flash forward. We're not yet to epilogue, but if we're looking at the end game.

• 2:04:11Tim Ferriss?

  I mean, to use chess, chess parlance in the chess sense, not in the objective sense. So I guess they're kind of the same in some respects. What is, what is one lesson slash story slash?

• 2:04:27Tim Ferriss?

  Maxim that you could share?

• 2:04:31Speaker 00

  Right, well, you've, you've endured a very volatile journey. You've optimized everything that works along the way with your product, with your team, with yourself. And then it's like, wow, I seen an insight. It could be, listen, things end in great ways or bad ways, whether it's a shutdown of something, whether it's a launch of something, whether it's an acquisition, whether it's going public. And there's also of course, like many finishes along the way, right? In any major, in any journey, but I really, I think that this notion of the final mile of something is very interesting to me because it's an entirely different sport. The stuff that you were so good at to get to this point of hopefully success is a completely different playbook than what you need to do to manage the decisions at the end.

• 2:05:15Tim Ferriss?

  And in this context, the end, are we talking primarily about acquisition or IPO?

• 2:05:20Speaker 00

  Let's talk about that first, although I think that some of this is relevant across other sorts of finishes as well. But a few things happen. I mean, first of all, you, with the confidence that you've built throughout the journey of getting there, you start to make decisions that you actually don't have the expertise nor experience to make. I remember getting a call from a founder, maybe like four or five months ago, who was telling me that, that he was really excited that one of these big kind of Google, Facebook like companies was doing their diligence on his, on his, on his company. I was like, oh, wow, that's really exciting. Where are you in the process? He was like, well, you know, they've come in and met the team. I'm like, oh, they've met the team.

• 2:06:03Speaker 00

  So you must have an offer on the table. Like, what, you know, what's the value? How is this going to work? And he said, oh, no, no, we haven't gotten there yet. And I was like, wait, so you had them come in and meet your team? And you don't even know, is this a talent acquisition? Is this, is this something you would do or not do? Like, how could you suddenly expose so much of who the people are and what you're doing and everything? And as the conversation unraveled, you know, he realized he had no idea what he was doing.

• 2:06:31Tim Ferriss?

  Yeah.

• 2:06:32Speaker 00

  And, you know, for him, it was like business as usual. And, you know, that's one example where that final mile, you know, is, is an entirely different sport. But I think the, I think that the, the other thing that happens that's really interesting is that people psychologically start to wonder, you know, whether they deserve what their, the success they're about to get. I remember a story in my, in my own experience with Behance. There was a member, senior member of my team who, right towards the acquisition, was starting to behave somewhat erratically, like was doing things at team meetings that were kind of offensive to people and that were kind of on the line of,

• 2:07:17Speaker 00

  and just starting to act out a lot. And I remember Confronting him a couple of times and he would kind of blow it off like, oh yeah, whatever. But it kept happening and I was just fascinated by this. And I remember going home to my wife one evening, who's a psychologist and talking to her about it. And she's like, oh, like he's, you know, this is self sabotage. I'm like, what? Like, he's been working his whole life for something like this. We're about to have this big payday and this big celebration. Like, why would he? And, and, and she kind of helped me understand when you don't feel like you deserve something, or when there's other sorts of parts of you that are not comfortable with like, what's happening, you can subconsciously sabotage yourself. So I came in to work the next day and towards the end of the day, when people

• 2:08:01Speaker 00

  were going out of the office, it was getting late, I pulled him into the corner of a conference room where it was kind of not visible. And I sat down with him and I kind of leaned over and I was just like, you deserve this. He's like, what? Like, what are you talking about? Like, this is okay. You deserve this. This is going to work out. And in that conversation, he kind of started tearing. It was one of those moments where I think, I think he was at first like, what the hell is he talking about? And then kind of, there was this connection we had where, where he sort of looked at his behavior as maybe something else. And, and I think that happens a lot. I think that there is this, you know, things do break down in the final mile. A lot of stuff changes psychologically. Artists, right? How much churn

• 2:08:43Speaker 00

  happens right before they ship? You've published multiple books, like how many times right before it's done, you're like, wait, wait, wait, maybe I should have done something else. Maybe I should have cut this piece, whatever. And that's like, by the way, classic behavior in every product release. There's always this period that we call kind of last minute churn, where it's like, wait a second, not ready to ship yet. So this is classic. And you have to be prepared for it.

• 2:09:04Tim Ferriss?

  Yeah. I mean, overriding typically comes in. I mean, there's a point where you lose, as a writer at least, so much perspective on the writing you've put down because it's been through 17 drafts or 374 drafts. You no longer have a tether to objectivity.

• 2:09:24Speaker 00

  Yes.

• 2:09:25Tim Ferriss?

  And yet, you know that there are probably things that could be improved. Still, you start to fuss.

• 2:09:31Speaker 00

  Yep.

• 2:09:31Tim Ferriss?

  With, in many cases, no particular direction or means of assessing your changes, but you know there are things to be fixed or improved upon.

• 2:09:42Tim Ferriss?

  Yeah, I would imagine it happens in a whole lot of contexts.

• 2:09:45Speaker 00

  I think it does.

• 2:09:46Tim Ferriss?

  And I mean, last minute jitters before a wedding. I mean, who knows? I mean, some of which might be well founded, not saying that's, you know, you should ignore your spider sense, but common.

• 2:09:55Speaker 00

  And I think that, so then the question is, so how do you make sure you have a successful final mile? And I think, I think part of it is starting to be alert of a lot of these tendencies that creep up right before shipping, right before being done, right before being acquired or whatever it is. And part of it is recognizing that the tactics that you employed all along suddenly may either be wrong or even detrimental. It's, it's really, this is a new game and you have to kind of take a step back. You have to get new, different types of mentors and help and help. I mean, literally, I mean, when I was going through my acquisition, there's a guy named Chris Dixon, who's a great investor, who is an angel in my, in my company. And he was the guy that was up with me at, what is it now, one in the morning?

• 2:10:40Speaker 00

  I mean, I remember those nights where he was helping me go through the cap table of our team and making sure that I was thinking about it properly. And, and, and I realized in that process, I had no idea what I was doing. I needed different types of help for different types of questions. And then there's the other kind of more existential thing that happens at the end of a project, which is suddenly, especially if it's successful, you, it becomes part of your identity. You become kind of known for something and you start to, you have to decide like, is that, is that going to be me? Or am I going to start to reject that and put it behind me? And you'll, you'll talk about, you'll, you'll hear some creatives and especially artists say that they just like to kill their old work. You know, it's, they like to do something completely different. Otherwise they feel like they're attached.

• 2:11:25Speaker 00

  I know authors who won't speak about their past books because it's just like, they got to move past that in a frame of mind.

• 2:11:33Speaker 00

  But that realization that, you know, you are not your work, being able to disconnect and disassociate when it's appropriate is another challenge in that final mile.

• 2:11:42Tim Ferriss?

  Yeah, super challenging. I mean, that's, it makes me think of my first and second book. I mean, I could have done the three and a half hour work week.

• 2:11:48Speaker 00

  Right.

• 2:11:49Tim Ferriss?

  Or milked the four hour work week. Plus, I could have milked that thing, but I was, I was really afraid of having to give the same talk on email auto responders until my dying day. As much as we would all like email to die, I don't think it's gonna happen anytime soon. And say, I made the, it was not an easy decision for me, but I had no evidence that I would be able to write about a different topic.

• 2:12:19Speaker 00

  Yeah.

• 2:12:20Tim Ferriss?

  It was my first book and, but ultimately made the decision that I could always go back to the well. If I ended up deserving it, meaning if the four hour work week was, was not going to disappear after a year. If I deserved it and it was still here in two years, three years, four years, I could go back to it. But that I had to do something different so that I didn't develop a defensiveness around protecting that as my identity and then correspondingly develop a risk intolerance to trying something different.

• 2:12:53Tim Ferriss?

  But that was hard.

• 2:12:55Speaker 00

  It is, and it's, and it's also, if you look at it from a business perspective, there's every reason to make a sequel and to, you know, squeeze the value out of anything that works. When you look at it from an art perspective, that's the opposite. And I think that that's, actually, I think the greatest founders out there, you know, recognize that while the, you know, the, the science of business is scaling everything that you can and automating and whatever. The art of business is the things that don't scale. And, and it's, you know, and, and they see their, their career in that way as well. It's like, I'm not just gonna be the enterprise SaaS guy, I'm not gonna be the this, I'm not gonna be the that. I'm gonna actually kind of find another edge, find something different, keep it fresh.

• 2:13:38Speaker 00

  And, you know, that's, that's admirable because it's, you know, it's, it's not the, it's not the path of least resistance.

• 2:13:46Tim Ferriss?

  Well, I think that life, business, art, you pick it, is very often not the path of least resistance. There are arguments to be made for both, but you will regardless end up having to deal with circumstances outside of your control, problems that couldn't have been predicted, new circumstances that require you to adapt, and maybe to grope around like a person in the dark for a period of time with great discomfort. And we've been talking about some of your lessons learned, some of the stories based on experiences

• 2:14:24Tim Ferriss?

  you've had, that you've had imparted to you from mentors. You've taken all of these notes, those that made the final cut. What is it, 120?

• 2:14:39Speaker 00

  Just about.

• 2:14:40Tim Ferriss?

  And I'm looking at this compendium in front of me, kind of a choose your own adventure guide within the buckets that we spoke about. So what is this that I'm looking at? It appears to be a book. I think you alluded to it, maybe mentioned it once. This is the messy middle subtitle. This is the final subtitle?

• 2:15:02Speaker 00

  This is the final subtitle.

• 2:15:03Tim Ferriss?

  No, no, no, that's fine. Before I read it, I wanted to make sure. Finding your way through the hardest and most crucial part of any bold venture. And I have, well, I was gonna say I've had a chance to read it. I've had a chance to kind of live through you, hearing many of these stories. I'm thrilled that you are sharing them. Where can people learn more about the book?

• 2:15:27Speaker 00

  Yeah.

• 2:15:28Tim Ferriss?

  I think the need is clear.

• 2:15:29Speaker 00

  I'm excited about it. It's, you know, it's, as you said, it really was that process of the 800 and something notes down to the, down to the 300, down to the 200, down to the 120, organizing these kind of three kind of themes we've talked about tonight, endurance, optimization, the final mile. The messy middle really is this passionate side project I've had for the last five or so years. I'm excited to get it out there, coming out, hits shelves October 2nd, 2018. And

• 2:15:56Speaker 00

  And then I'm trying to also, though, like, continue these as conversations. You know, on Twitter, I'm just @scottbelsky. And frankly, a lot of the stuff we talked tonight are things that I've also shared over the years and tested and gotten feedback on and incorporated into ultimately, you know, what this book has become. So I think that we're all in our own messy middles. And I just hope that this, you know, this helps people know that they're not alone as they're in the enduring phase and managing the volatility. I hope it helps them mine it a little bit more productively. I hope it helps people build better products that all of us can benefit from and optimize anything else that's working within their team. And when it comes down to that final mile, let's not screw it up. Let's ship.

• 2:16:43Tim Ferriss?

  Here, here. Well, Scott, thanks for the endurance of this marathon across multiple types of scenery, within certain types of scenery.

• 2:16:55Speaker 00

  Not gonna lie, it was intense.

• 2:16:56Tim Ferriss?

  At different temperatures, maybe in some ways like the messy middle.

• 2:17:01Speaker 00

  There you go.

• 2:17:01Tim Ferriss?

  And to everybody listening, thanks for being a fly on the wall and also accepting this experimental format. And you can find links to anything we might have talked about, some of the people we mentioned, the founders and their products and companies and so on, in the show notes, as per usual, at tim.blog/podcast. And until next time, as always, thank you so very much for listening. I love doing this and you guys make it possible. So, through the internet to all of you. Until next time.

• 2:17:41Tim Ferriss?

  Hey, guys. This is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? And would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums. ...that I've discovered, it could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short.

• 2:18:23Tim Ferriss?

  It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out, just go to fourhourworkweek.com. That's fourhourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by LegalZoom, which more than 2 million Americans have used to help start their businesses. Past guests even, such as WordPress lead developer, CEO of Automattic, Matt Mullenweg, now valued at more than $1 billion, have used LegalZoom to help with their business needs, specifically in his case, to form his company. But LegalZoom isn't just for launching your business. Their services include everything from helping you to manage changing tax laws, reviewing

• 2:19:08Tim Ferriss?

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• 2:19:50Tim Ferriss?

  I don't know what the special savings is, folks, but it's titillating. If you want special savings, enter promo code TIM, T-I-M, at checkout. Capital T, lowercase i-m. Again, take a peek, LegalZoom.com and enter promo code TIM.

• 2:20:07Tim Ferriss?

  This episode is brought to you by FreshBooks. FreshBooks has become the go-to cloud accounting software for literally millions of small business owners who found a faster, more efficient, and much less stressful way to deal with their numbers. Ultimately, this helps you to focus on what you are best at. It is used by many of the fastest-growing startups I've invested in or advise, and it's equally used by many of the best freelancers I work with on a daily or weekly basis. It is one of the easiest ways to send invoices, get paid, track your time, and track your clients. If your self-employed and managing business sometimes means wrestling with spreadsheets, crumpled receipts, and other scattered pieces, FreshBooks can really help. FreshBooks allows you to do many, many different things very easily. Preparing and sending a polished, branded invoice takes about 30 seconds.

• 2:20:52Tim Ferriss?

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• 2:21:35Tim Ferriss?

  Go to freshbooks.com/tim and enter Tim Ferriss in the "How Did You Hear About Us?" section. And that is funky spell, T-I-M-F-E-R-R-I-S-S. So again, go to freshbooks.com/tim and enter Tim Ferriss in the "How Did You Hear About Us?" section. Check it out.