The Tim Ferriss Show - #336: Scott Belsky — How to Conquer the Messy Middle

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Starting point is 00:04:01 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 is 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. He's 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

Starting point is 00:04:53 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 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

Starting point is 00:05:43 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. 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 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 asked my friends for help, because I was getting all wound up about a very, very top of mind situation when Scott showed up at my house, jump about 55 minutes ahead from where we begin the interview. So the easiest way to do that, if you want to,

Starting point is 00:06:32 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. And with that, I will let you also, through your ears, hang with none other than Scott Belsky. Scott, welcome to the show. Thanks, Tim. Here we are at the kitchen table.

Starting point is 00:07:07 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 going to know what I'm referring to, how many Evernote notes? Well, a lot of Evernote notes. But specific to what we'll be talking about?

Starting point is 00:07:32 Yeah, I think it was, it started at maybe 830 or so a couple years ago when I started trimming it down. 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.

Starting point is 00:08:00 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. 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,

Starting point is 00:08:59 and a few new muscles there, navigating a 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.

Starting point is 00:09:20 Then realized I missed 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 realized that they all conflict based on whatever context you're in. And the things that I 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.

Starting point is 00:09:56 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. And 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 in some capacity talking to you yes uh and you've collected these notes over time so i thought what the hell and we talked about this maybe or maybe

Starting point is 00:10:55 not after a few glasses of wine a bit earlier today we should just record a podcast. So here we are, late night, at Shea Farris. 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 start exploring some of these maxims, some of these notes, and you can tell us the story behind it. And we're just going to riff.

Starting point is 00:11:28 So let's do it. Sure. Well, I have to say, when I started to... It was actually on a plane a couple 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 second of all, this is really disorganized.

Starting point is 00:11:44 Should I start to organize them based on some theme? And ultimately, 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 whether it's a new venture or a turnaround of something or a bold, creative project? I feel like a lot of them, that was the theme. How do you just stick with it long enough to figure it out? How do you have the persistence and the patience 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,

Starting point is 00:12:19 is optimization. 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 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 called the final mile. I found that whether it was entrepreneurs I've worked with over the years 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 done. There's a lot of interesting stuff that happens, some self-sabotage, new doubts. You think you know what you're doing because you got that far and

Starting point is 00:13:03 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. So you got the buckets. Let's dig into some examples. Sure. No. So I think that if we go in that order and you think about endurance, you know, one of the, one, one of the, there were a number of different observations around, and especially from my own experience, building a startup and bootstrapping 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. And you said organizing the creative world, I think, may have been the wording you used.

Starting point is 00:13:48 What does that mean in practice? What were you trying to sell? Yeah, for Behance, the insight was that the creative world, meaning any sort of design, photographer, architect, illustrator, in the world 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 career is at the mercy of circumstance. And the idea behind Behance, which was my startup back in the day,

Starting point is 00:14:19 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, uh, uh, we, but we didn't really know what we were doing. It was a bit of a team of misfits in the sense that all of us had roles we weren't necessarily qualified for when we were building this team in the early days. And, um, what I learned very quickly was that the idea that we wanted to come together for that thing that motivated us to, 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. And I remember there was a

Starting point is 00:15:16 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 for starters we had a name for our company called behance which didn't mean anything didn't exist and so in every type

Starting point is 00:16:02 every every time you typed it in google it said 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, 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 milestone. And those became this new reward system that governed and actually kept us together.

Starting point is 00:16:49 And we remarkably didn't really lose many people, at least voluntarily, for a number of years. 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 world-changing company is actually going to take quite a few years and that people are starting to not going to say founder, but realize the gravity of that reality is beginning to hit them. And the CEO, maybe sole founder,

Starting point is 00:17:29 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.

Starting point is 00:17:44 Do you have any recommendations for that person? A few different things. 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 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, we just crossed the state line.

Starting point is 00:18:17 Oh, there's 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 that's one of the jobs of someone at the helm is to build that narrative. And part of that is a creative endeavor 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 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.

Starting point is 00:18:57 You mean play out for yourself or in front of employees? In front of the team. What would be an example of that? 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 market marketable this is going to be one of the best experiential

Starting point is 00:19:28 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 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. Well, 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, this is, I think, one of the most under-discussed and valued sales functions of the CEO. They think of selling investors.

Starting point is 00:20:17 They think of selling employees, but for the hiring of those employees. But to retain a team in the early days, this is so, so important. It's merchandising. I mean, think about 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 help your team accept the burden of uncertainty, right? And it's just so much easier when this stuff is around you. So you also use, 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

Starting point is 00:21:14 you still do this, but you have your like Scooby snacks and deep, deep work rewards. Do you still do that? I still do that. Can you tell people just briefly what that is? Because I'm sure a lot of people are listening who are perhaps solopreneurs 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. Yeah. So what is this? What is, if you could just describe this for people. The, well, I mean, it's, I guess it's short circuiting my own reward system.

Starting point is 00:21:46 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 can you listen to it from the get go or do you have 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. What are some of those, those tracks? Do you, do you remember? Yeah, there's, um, there's, uh, a couple of great sort of melodies that I kind of love. I mean, one is, uh, this piano melody by a woman named Carly Commando that I discovered once. Um, there are, uh, gosh, I mean, there are just a few other things that I love that I think I can work with that I didn't want to burn out. But I also just wanted it to be like that reward,

Starting point is 00:22:32 like when I'm back in the writing zone, I'm feeling it. And there's snacks. And the snacks. So what are the snacks? And when are you allowed to have the snacks? 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. Yeah. Those delicious snacks, the, 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. So in the zone now as a, as a little piglet myself, I might be inclined to be like, oh man, just now my first paragraph, let me have some chocolate. So what's the bar for in the zone?

Starting point is 00:23:12 Yeah, no, it's when I get a material chunk done. When I feel like I, I mean, as I talk about this, it sounds ridiculous, but it's not right like how 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 yeah just like we do with customers and 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. Okay. So we've talked about reward systems. 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

Starting point is 00:23:57 when they're realizing, wow, okay, I thought I, in my mind, had 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? There's a lot of tough moments in that middle. There are a lot of meetings that don't have answers at the end. There's a lot of periods, again, of that ambiguity where you're kind of going in circles. There's rework. You launch something, you realize that it was built on the wrong tech stack or that it was totally for the wrong type of customer

Starting point is 00:24:29 and you have to redo it again. And leaving your team constantly with energy, even after those very difficult bouts. I remember one guy I worked with, a guy named David Woodwani, who's now the CEO of AppDynamics, a company out in Silicon Valley. But I remember every time I was in a meeting with him, and they could be just the most depressing meetings, he would always kind of end with a recap that would, again, spin it around towards, we got this. We 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,

Starting point is 00:25:10 right? To keep people engaged, enduring. 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 when we were hanging out that was related to your, I guess, suppressed memories during the five years of bootstrapping when you went back 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?

Starting point is 00:25:58 Well, and it goes back to that reward thing, I, as well. I went back in my phone to that five years because I was actually surprised by how much I had forgotten. And I was wondering, did I forget it because I wanted to? Was there just nothing that is worth remembering? And so, yeah, I flicked back really quickly in my phone back to those years. And what did I find? I found tons of screenshots um i found a few you know i i really i remembered 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

Starting point is 00:26:39 random screenshots of people saying nice things about the product. And then I remembered, gosh, I used to always try in a regular rhythm to send those around. We didn't have Slack at the time, but you would post them on Slack now, I guess. Those are, again, like those little jolts of reward that are keeping the team feeling that this is the narrative. But it doesn't happen naturally, right? And you have to look for it, you have to merchandise it. But yeah, I was surprised by how much of that five years was

Starting point is 00:27:11 just kind of this, gosh, like, you know, late nights, because you can also see like the time stands of screenshots. It's like, gosh, I was lying in bed at 2am looking at typos and stuff and sitting around. But that is a big part of it. And once again, you can use this for yourself. I mean, 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 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

Starting point is 00:28:00 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, it can, it can put you, or it can put me at least into perhaps a productive space, but a, 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 screenshots of occasionally of really meaningful, say, letters or comments from fans, and I will favorite it on my phone so that I have a few things. This is actually something I picked up from comedian Whitney Cummings, sort of 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

Starting point is 00:28:41 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 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, 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. It doesn't always do it, but what it can do. And that's like the positive part that helps you keep going. I think there's also, um, that helps you keep going. Yeah. 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

Starting point is 00:29:30 fucking job. Right. I think that was your answer in trauma mentors to, uh, what do you do when you feel, what was it scattered or overwhelmed? I whispered to myself, Scott, do your fucking job. You know, I do. And especially in moments where I've had to make a difficult move, fire somebody, make a difficult call, have a difficult meeting. There is that sometimes whisper of, hey, yes, I could try to, you know, find other ways to make me feel good about this, or I'm just going to tell myself that this is what it takes. What I've never asked someone because, 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're bootstrapping or afterwards,

Starting point is 00:30:27 right? 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. 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 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, at least personally for me, was like, gosh,

Starting point is 00:31:15 it's when things are going really well that you start to say, hey, 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. And then again, rewarding good outcome without looking at process that hurts. And that, you know, that can be a fatal flaw. And, um, 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. So is that, that's something you did at the time? Oh yeah. And then I think throughout, throughout my journey, 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

Starting point is 00:32:01 those were patterns? 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 dribble that was doing a little 400 pixel snapshots of people's work. And by the way, that always looks better than the full project. Cause 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, uh, a real differentiation from our product. And the fear of that made us suddenly shift our shift. I can hear the tea. I'm sure people can do. Fortunately, these mics are very directional, so we should be okay.

Starting point is 00:32:47 That is water boiling, folks. If you hear it, that is water, not my stomach. 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

Starting point is 00:33:15 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 example. So I think that's one of those examples where it was more in retrospect. I think at the time, though, I just try to find, I try to ask myself why I react to things in certain ways. Why did that meeting make me feel unsettled? What was it? Like, is it something that someone said? Is it, 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, uh, 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

Starting point is 00:34:08 misspending a lot of resources as a result. How do you ensure that doesn't happen again? Or how did you? Or 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? It's fear. What is it fear of? It's fear of this. Right. What do you then do with that? Because,

Starting point is 00:34:28 uh, I mean, I think the, the hardest advice to take is often the advice you have given yourself or already realize that you need to do. Right. I mean, uh,

Starting point is 00:34:39 not to incant 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

Starting point is 00:35:03 it out and And I'm asking selfishly because I've got tons of stuff to work on. What do you do? Well, I'm still figuring out it as well. But I would say this is where the team comes in. I have and I've always had people on my team that were really different. Well, let's start to interject. This is where the yerba mate can be my scapegoat. But let's take the meeting example. 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? Hmm. Well, I think, let's see, I'm thinking of a

Starting point is 00:35:47 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. Okay. So that was the response from the other side. That was the response from the other side. And it threw me off. I was like one,

Starting point is 00:36:29 you know, like I've got lots of products and lots of things going on and, and, um, and you know, every business is dynamic. How could you not have one thing? I mean, that sounds crazy. And it really threw me off. Um, and, uh, and then I, and then I started to think, gosh, maybe I'm doing what I always tell people not to. Maybe I'm spreading myself too thin. I'm not having enough conviction on the one thing that matters. Am I a good manager? Am I a good leader? Am I being formed properly? Do I have enough data? You start having all those kind of self-doubts arise. And then I think, I mean, in this particular situation, 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

Starting point is 00:37:20 more than everything else? And actually, 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 had to pick one or two, I think that those have an outsized proportion of are 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. Are you doing this in your head, in your office as a postmortem? Are you doing it on paper, typing it out? Usually I'm doing it on planes. 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 view. You have to have an opinion. You have to have an answer, especially if you're a leader,

Starting point is 00:38:07 but it's really outside, right? When you're just disconnected and you're kind of letting it run through your head. Um, and if you have, but what you have to be doing is, is starting from the belief that you're wrong. Yeah. 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. Right. And you, 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 you do, and it's, it's provocative because that, I mean, and you have to be provocative in your thinking. Right. So, um, you know, I actually, when you, right? So I actually, when I caught myself

Starting point is 00:38:47 on 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 that actually, in this case, impacted a number of meetings I set up and conversations I had

Starting point is 00:39:03 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. 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 Wi-Fi 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 computer, offline.

Starting point is 00:39:35 How are you running through these what-if scenarios? I usually start in my head and then I start getting a little anxious because I'm like, oh, 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...

Starting point is 00:40:00 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, deepurning. Um, 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, uh, provocative inner, inner, inner monologue. Awesome. That was great. Uh, let's, let's dig back in speaking of, well, I think that one of those little notes that made it to the finish line for me was this question around suspending kind of disbeliefs as another tactic towards endurance. I remember my father as an orthopedic surgeon, but when he was a resident, he was working in of those crazy New York city hospitals where people would come in with like overdoses and shooting wounds and stuff like that. And, um, he was telling me that the most often kind of prescribed, especially on a cycle on the psychiatric stuff that came in was, uh, it was like, you know, a hundred CCS or

Starting point is 00:41:00 whatever of Oba kelp, which is of course, placebo spelt backwards. And, um, and how like, you know, as soon as, you know, someone would be like Obacalp stat, you know, a hundred CCS, uh, 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. And, uh, you know, that always stuck with me. Um, and I was always kind of wondering, how do I prescribe that 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, good plan. How do you do 100x that? And that jolt to the system suddenly throws the current project plan out the door.

Starting point is 00:41:47 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. Because first of all, the disbeliefs you had in your more reserved plan are suddenly out the door because that sounds easy suddenly. Because this new thing, I don't even know where I'd start. And I think that there are ways we can make sure that we just have exponentially more belief in ourselves at times. Um, um, now part of it also is, is a, uh, is, is also taking, taking pride in how naive you are in certain areas. Um, I mean, I remember talking to,

Starting point is 00:42:34 uh, 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 um i think that there's sometimes you know hiring people that think differently or don't have don't don't have the traditional um expertise that you think you're needing to hire. I think you sometimes have to recognize the benefits in not knowing too much. Right. The constraints of an industry which may already have been, you know,

Starting point is 00:43:20 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. Uh, yeah, I don't know. I don't know the answer, but I don't either. Uh, 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, maybe they just had to lay off half the company,

Starting point is 00:44:04 but 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

Starting point is 00:44:20 when they're in those circumstances? 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 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.

Starting point is 00:45:08 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 I'll say, well, but how do I know whether I should quit or not? 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, right? We had multiple near-death experiences. Right. Right. And if you're bootstrapping, my God, you know, you, you, you, there's a, oftentimes a survivorship

Starting point is 00:45:50 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 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

Starting point is 00:46:20 headstone for my company and move on versus persist through these very difficult times? Well, I think, um, I mean, to me, the answer is pretty simple. Uh, first of all, you recognize the fact that everyone's kind of messy middle journey is, is, um, is, is, is at times hopeless and, um, and, and that self-doubt is a real thing. And, um, and so you're not alone. Um, however, if you start to lose conviction in what initially set you off on this journey, I mean, that's a serious thing. And, uh, 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,

Starting point is 00:47:08 when they're making, having that question, how do you assess conviction? Um, to me, conviction is, um, is really about, um,

Starting point is 00:47:18 knowing that the world is going to be a certain way based on all of the work and, and, and research and experiences that you're having. And I don't care what the company is, what the product or services that you're trying to make as you go about it day by day, you learn more and, um, and you start to realize where you were right and where you were wrong. And, um, 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

Starting point is 00:47:49 blah, blah, blah, blah. You know, they don't, they don't want to have a laundry done within a three hour thing. And that's not a real opportunity. But since we raised $2 million and we've got a teamwork and like, we're just going to stick with it. I actually think they should quit. However, if the answer is, oh, my God, this is even more inevitable than we ever thought. This is more important. This problem is actually going to be bigger than we realized. And we just have so much more conviction, even though shit's hitting the fan right now. And gosh, our product is completely wrong.

Starting point is 00:48:24 And 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. Have you, you know, rather than, I was going to throw out a tough case,

Starting point is 00:48:43 but which you see sometimes, let's say like Odeo, way back in the day, although ultimately it transmogrified in some fashion into Twitter, but they were pursuing what one could argue has become the now ubiquitous podcasting and things of that sort, but they paddled for the wave really early.

Starting point is 00:48:59 Right. So 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

Starting point is 00:49:16 longer than you can remain solvent. Something like that. Well, timing is a bitch, first of all. And investing is really less about the future and it's more about the present. In what way? In the sense that you can have the greatest idea for 10 years from now,

Starting point is 00:49:37 but again, time is the enemy of every bold endeavor. It's just 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. And I think that, 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

Starting point is 00:50:01 corner. We're already there. And, and then, and, and making your like product and team bets based on that knowledge, um, rather than 10 years in the future. Yeah. Something like that. A lot of investors get stuck because it's easy to be a visionary

Starting point is 00:50:15 and know that someday, yes, we will have flying cars. That does not mean that we need to be making flying parking lots at this moment. Uh, what else do you have? I mean, one last thing on that front, I would say is, um, something I I've seen for a number of founders. I know Ben Silverman, 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 journey, multi-years and the merchandising and whatever and this idea of breaking it down into chapters he

Starting point is 00:50:52 when he talks about Pinterest he'll talk about the fact that year after product market fit then there was the year of internationalization and everything in the company was geared around let's go global let's stop these clones Um, then there was the year of internationalization and everything in the company was geared around. Let's, let's, let's go global.

Starting point is 00:51:07 Let's stop these clones. And then there was a year around monetization. Let's figure out how are we going to have a business here? You know, and, and, and each year has had, it has been like a chapter and that's how he, I like frames prioritization and, and, and, and maybe I guess kind of goes back to that, you know, drive with a, 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. You need, you use the, the metaphor of the, the,

Starting point is 00:51:42 the like kidnap car with the blacked out windows uh one that I've also heard not applied to startups but to novels actually writing novels that I like

Starting point is 00:51:53 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

Starting point is 00:52:00 is a bit like driving across the country with your headlights on oh yeah Anne Lamott I think it very well could have been Anne Lamott, I think. It very well could have been Anne Lamott, because Bird by Bird is one of my absolute favorite books,

Starting point is 00:52:09 and I gift it to everybody, which I should probably also give to startup founders, quite frankly. Yeah. 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? I think that's part of it. And the other part about it is how you build patients into the way your team is built. If you look at a company like Amazon, I think they have a cultural setup for

Starting point is 00:52:36 patients, this notion of being willing to be misunderstood for a very long period of time. It's very embedded in the culture. 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 build patients 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 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... What did Amazon, sorry to interrupt, but the being misunderstood for a long period of time, is that as a company or as a person within the company? Well, I think it's both. I mean, obviously... And they do have their, whatever it is, not 10 commandments,

Starting point is 00:53:25 but like the 10 tenets of Amazon or something up on Amazon somewhere. I don't recall exactly what they're referred to as. They also have their original shareholder letter that they attach to every new shareholder letter and is sort of a Bible within the company that also is all about that. It's basically saying,

Starting point is 00:53:42 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. And 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. Amazon Web Services. Yes. And you see other parts of their business become huge businesses on their own because they're just willing to invest that way.

Starting point is 00:54:11 You have to have a way though, because I think the realization here is that we are all impatient. I mean, part of my belief is that it's just biological, right? I don't know what our life expectancy was hundreds and hundreds, if not thousands of years ago, but it was hell of a lot shorter than it is today.

Starting point is 00:54:28 And so the notion of committing 10 years of your life to something was just insane and very unwise. And so when we do that, we are going- Get out there and procreate now. 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 those short-term reward system hacks. You have to have things like the cultural mechanisms or the structural mechanisms that push patients, the chapters, the merchandising.

Starting point is 00:54:54 Since I'm going with stream of consciousness for a minute and certainly going off script, you mentioned Amazon. I'm fascinated by Amazon. Stratechery's blog has some fantastic, fantastic articles on Amazon 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. what do you read when it comes to investing entrepreneurship or other, like, are there any newsletters, main Twitter accounts,

Starting point is 00:55:32 anything that you can mention that you find really thought provoking? Well, Ben Thompson, who you just mentioned, is certainly, you know, one of the, one of the greatest thinkers I think on what's happening every day and always

Starting point is 00:55:45 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. Uh, I think there, you know, there are a lot of different investors that I, um, that I follow or subscribe the newsletters for, because I want to hear, um, you know, their view. Uh, and, um, I'm trying to think of others who, yeah. And anyone who comes to mind, recognizing this is not an exhaustive or complete list, but folks who you... Like Trent Griffin, a guy who has been at Microsoft for a long time, close to Bill Gates and has observed the software industry evolve and has a lot of insights around what's going

Starting point is 00:56:41 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, it's, 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. Tren Griffin? His name is Tren Griffin, right. Josh Wolf, who's a great investor in New York of a firm

Starting point is 00:57:17 called Lux Capital. He's actually been an extreme skeptic of Tesla for a very long time, calling out from his vantage point around some of the fundamentals. And also, I think he's used to entrepreneurs that have very wild personalities for future narratives. And he pokes holes for a living in that. And so he has some perspective on what he thinks 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, uh, some different perspective. Thematically, if you look at the non-investment reading that you do, uh, if you look at the pie chart, is there, is there anything in particular that you're consuming a good amount of these days

Starting point is 00:58:04 or over the last say say, year or two? You know, I think that there's some biographies, the Doris Kearns Goodwin type stuff, the Walter Agasson classic biographies. I think there's recently read Shackleton's Endurance story. Appropriate. Yes. Which obviously relates to my thinking these days, which is just a phenomenal story. Appropriate. Yes. Which 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 difficult decisions that have to be

Starting point is 00:58:38 made. And does anything come to mind? Oh, gosh. I'm asking a lot. I know. Yeah, I know. But like, well, one actually thing that stuck with me was, um, 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, um, 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, what do you mean?

Starting point is 00:59:07 You're the leader. How could you put your team at risk? But he realized that 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. 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.

Starting point is 00:59:31 We had to survive. We had to move faster. Like that's an example. 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? Wow.

Starting point is 00:59:44 You have to be thinking quite, quite quickly to play, play through the different scenarios in your head and make that judgment call and be willing to be unpopular. Yes. Um, and, and, you know, and, and take a risk. I mean, that's, that's a risk, right? So I think we, 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,

Starting point is 01:00:18 and move into the truth barrel, if you're up into that. I'm ready. Okay. Pause. 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 a, uh,

Starting point is 01:00:39 the coils of a, uh, 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,

Starting point is 01:00:57 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 uh the acoustics might be a little weird so bear with me dear listeners and i thought i would i would segue by selfishly focusing on myself and a problem 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.

Starting point is 01:01:37 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. 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. Uh, but I think that in many,

Starting point is 01:02:26 many circumstances it is misplaced and outlived its usefulness and it's just corrosive for me. So here's what happened. Uh, for the last, uh, few months I have been interacting with this nonprofit to, uh,

Starting point is 01:02:42 do volunteer work for them, uh, 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 costs quite a lot as it relates to time.

Starting point is 01:03:15 Time. In particular, this non-renewable 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 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. So I received finally, after tons of back and forth,

Starting point is 01:04:01 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 sort of irrevocably spent this money yep and i'm just like what the fuck and right and uh 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 i'll be faster yeah i'm going to be thinking about this which will not have any resolution

Starting point is 01:04:56 yep if it's if it's going to have any resolution which it might not it's not going to happen until next week monday onward right so what would you do in this in this circumstance or or if you were in my shoes as my even keeled 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 uh in this direction just for the the first portion of this part due 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 you're the average of the five people you associate with most who do you associate with most and why and you would be an example i would give it'd be like i aspire to develop these characteristics which i

Starting point is 01:05:58 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 haven't developed what would you do 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, what would 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,

Starting point is 01:06:46 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 going to have to like roll with it. And how much of my energy am I going to give to it if I have no influence over it? And cause then it kind of boils down to math for me. It's like, all right,

Starting point is 01:07:04 like this sucks. But, um, the, the sunk cost thing, um, kind of fly is, is oftentimes, you know, the, the, the, the wild card in this notion of righteousness that a lot of us have, I think. Yeah. And if it helps at all, uh, I would say that when something is obviously outside of my control yeah a crisis situation yeah uh 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 yeah i can i can handle it very very well yeah uh sunk cost fallacy as it relates to money yeah doesn. Doesn't really apply for me at least.

Starting point is 01:07:46 Like if I, if I make a bad bet, I'm not going to follow up, uh, good money after bad if it's not working out. But with time. Yes. Yeah. Different story. I think the other factor. I do get that righteous indignation, which I recognize almost always is a huge mis-expediture of additional energy and time.

Starting point is 01:08:09 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 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? That's a good, that's a great one. 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.

Starting point is 01:09:02 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. And at some point there's just certain limitations that I think people have. And then 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,

Starting point is 01:09:38 org industry, whatever to change. And, um, and, uh, you know, and then, and, and then you, and then you have to become like a fierce protector of like extraneous energy 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 uh how how would you then explore resolution or next steps in your own head? Well, the hack that I would use is that what I'm enduring in this case and putting up with and what I'm tolerating is part of my contribution. So when I go to nonprofit board meetings and that sort of thing that I find, generally speaking, much less productive than other organizations I'm involved in, or certainly startups where it's all about what needs to get done, let's get out of here, everything's scrum and it's a standing meeting, it's obviously very different. I do sometimes tell myself, this is part of the condition that I committed myself

Starting point is 01:10:45 to work under. I'm reminded of a great piece of advice that John Maeda, one of my mentors once gave me. Um, I think I may have shared a view. Uh, maybe could you just for people who don't know him, who is, who is that? John is, um, 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 people with famous names on the board and a very kind of old institution. And it just moves slowly in some ways because that's how it has sustained for so long.

Starting point is 01:11:40 Of course, it hasn't gone through radical change. That's what makes it in some ways sustainable. 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, how do you manage such an unproductive meeting? 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 100 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 that 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.

Starting point is 01:12:38 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. Okay. manage it okay so that that gives me a cooler head even in this hot 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

Starting point is 01:13:23 yep for the email or phone call. How do you think about that? Is the question, how do you now keep a cooler head? Well, I mean, the options to me, I'm sure are many,

Starting point is 01:13:37 but the ones that come to mind are I can accept what they've suggested, which is in no way representative of what I, that wouldn't be you, the person I know. Yeah. It would not be me agreed to or particularly want to do. Yep. And it actually has some conflicts.

Starting point is 01:13:54 Uh, so it's, it's not really an option to accept this. It's practical. Yeah. Number two is to ask for something completely different, which is in fact what we agreed to in the beginning, but they've already slotted all the other volunteers. So it may or may not be possible

Starting point is 01:14:07 or something in the middle, or, or I don't do it at all. Right. So the Tim that I would know by default, in my opinion, knowing, you know, having known you for years is, uh, you would say I'm out right. You guys didn't know 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 yeah that that is my instinct yeah but i really there's the other part of me that's like maybe you just need to wait for your testosterone to decrease over time it's a good exercise and you should try a different approach because there are times when i have cut off my nose to to spite my face yes know, out of principle would be the justification. And in retrospect, it's just like, what the fuck?

Starting point is 01:14:49 Really? I mean, 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, uh, you know, and, um, 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

Starting point is 01:15:26 thing tends to be a repeatable pattern. And you probably know what you're in for. Yeah, we'll see. I mean, maybe, you know, this surprised me. So maybe their response to the next one will equally surprise me. But hey, this postmortem, like this process, I mean, this is what develops muscle memory. This is what develops our judgment. And honestly, even though there's no clear resolution, I feel better about it just having walked through the practical, tactical 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.

Starting point is 01:16:15 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 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 yes there was this part of me that was like but this is your freaking honeymoon and like you get this once hopefully and uh and you got to like at least be present for part of it and I remember that was like the beginning of my education I was

Starting point is 01:16:59 trying to compartmentalize that stuff it's fucking hard 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 yeah and what does that really mean on uh you know i think it's i think it's on a cognitive level or not necessarily you know mechanistically but for someone who says wow uh belky 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? 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

Starting point is 01:17:39 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. How do you do that?

Starting point is 01:18:03 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.

Starting point is 01:18:31 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. And it's just like, Hey, um, if you're a pro, like you should be able to do this. And yeah, that's kind of what I tell myself. Yeah. Well, it's a, it also reminds me.

Starting point is 01:18:58 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, uh, 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,

Starting point is 01:19:19 it makes me think of something that I haven't thought of in a while, uh, that Robert Rodriguez, the filmmaker said, uh, when I was chatting with him on the podcast and that was, he has film milk. I'm paraphrasing here, of course, and Robert, forgive me if I get it somewhat off, but filmmakers come up to him 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.

Starting point is 01:19:46 And then this and this and this. And they, they list off this litany of complaints. And, uh, and Robert just says, 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. And that is what you do. Right. Your job is that nothing is going to go right. And that is what you do. 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,

Starting point is 01:20:18 based on what the team is, how part of the product 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 1.2. 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. Yeah, absolutely. Absolutely right. All right.

Starting point is 01:20:39 So let's talk about the, the second bucket optimize. And 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. Definitely. So now that we're half naked and sitting in a sauna sweating together, let's get sexy.

Starting point is 01:21:00 Yeah. Where would you like to start? 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 fell in these camps of team self-product. And I would just start 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 point is 01:21:18 starting something as a solo entrepreneur, or you're actually leading a team. I think one, I would just start with the fact that we all 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 form of creativity and there's a 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

Starting point is 01:22:06 and never developing that muscle typically actually don't end quite well. So when it comes to thinking about that, a couple thoughts. One story is when I first hired our first kind of operations leader, a guy named Will Allen. Actually, he worked at TED conferences prior to that. And he came on board to kind of kick 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 need a bigger budget for web storage space,

Starting point is 01:22:39 we need more people for this, for that function, whatever. Will would always say, he had this mantra, refactor, refactor, then hire. 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, each person oversees one part of the product. Could they oversee two instead? Are there any benefits to that?

Starting point is 01:23:05 Should we cut some of the cruft? Like, are there people that we should shift around? Should we actually pick the feature that 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. But when you have to choose between the two, it has to be forced, I guess is my point.

Starting point is 01:23:29 And that has become a real, actual principle for me as a manager and as a board member and as an advisor is constantly challenging teams to find creative ways they can refactor and also making the case, even if they have the resources, as to why that benefits them. You know, I was just going to say that, uh, one of the most valuable things that I've done in the last few years, which I should have started a lot earlier, uh, that I'm, uh, I think I'm, I'm better at than perhaps the avoidance of emotional reactivity as it

Starting point is 01:24:01 relates to anger certainly is journaling on hypothetical questions that constrain your resources even if you have them interesting 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 yes right what if we had to accomplish, what if we had to finish this, and it might mean that the metrics change, in one week? Yes. Right? What if we had to finish this and we couldn't personally as a team touch it?

Starting point is 01:24:31 You had to outsource all of it. Hey. Would that simplify the specs? Would that simplify what you submit? Right? And then does that end up being usable by the team, right? And I apply it to time. Any currency I can think of, right?

Starting point is 01:24:42 Yep. Head count. 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. By the way, I mean, it's true on the individual level, on a small team level.

Starting point is 01:25:09 There's also a company, a company called Skybox, that was started by four Stanford students. 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, off-the-shelf parts. That was the ultimate constraint. And that was the fuel of innovation. They ended up building satellites between two to five million, which is a fraction of

Starting point is 01:25:34 what satellites were being built for. And then 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. Yeah, that's a great story. For people who want to hear or read a great story of resourcefulness, this just reminded me, and somebody else is going to have to look this up, but there was a robotics competition. You might have heard of this or seen it. A feature film was made out of the story.

Starting point is 01:26:07 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 the the narrative and the journey is really the payoff not the the end which is easy enough to figure out yep but they were competing against these very well-heeled uh upper-class, perfectly educated teams, and they had to scrap by with essentially no budget to learn and build robotics to compete underwater. And it's just such an amazing story.

Starting point is 01:26:58 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. It's a common story. It is counterintuitive. Even if you benefit from that, you actually still

Starting point is 01:27:22 start to operate differently when you start having the resources at your disposal. The same thing, by the way, goes for hiring. Another thing that I've observed in many instances is initiative being more important than experience. And you're hiring people. And when you have the resources, you tend to become a resume snob. And you're like, oh, I'm going to have a VP of this from 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?

Starting point is 01:27:55 What's their history of doing that? And will they continue to do that here? What does initiative mean in this case? I have an image in my mind because that's something I look for. To me, initiative, it's when you's really, um, it's when you're genuinely interested in something, do you take relentless, persistent and continuous action? Um, is it something that you, you, you hold your eyes up at night to do more of, um, versus are you, are you confining yourself to the job description? Yeah. So in some of it, some of, I always like to say, like, I feel like so much of the future

Starting point is 01:28:23 is, is done by people doing work they didn't have to do. And if that's true, it's really about people who take initiative over 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. Let me do my thing. And by the way, I had three assistants at Google. Which three assistants are you going to hire for me?

Starting point is 01:28:44 I haven't written in code in a while, but yeah. Yeah. But the, you know, it jumps out to me and I I've hired far fewer people than you have, but looking for a 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 yeah but it's important and i say all right off the cuff i imagine we're going to do a b and c and then as as the final step you're going to have to choose between one two three yep and if someone comes back and says i looked into all that but i think the better option is number four, and I actually tested this out.

Starting point is 01:29:26 And although you didn't ask me to do this on my own time, I did this. It's like, okay, that displays initiative. It also displays an understanding for the circumstances I was experiencing, buried under, suffering from when I gave the order. Yes. 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,

Starting point is 01:29:54 I've become better at it myself. Yes. Which is, uh, which has been a huge key learning for me. And, uh, this is,

Starting point is 01:30:01 this is meandering quite a bit, but that is, that is my way. Uh, that also, I mean, you, you, by, by observing other people, this is meandering quite a bit, but that is my way. It makes sense. That also, I mean, by observing other people, you can improve those qualities in yourself if you really pay attention and also reviewing what they've done. And vice versa, right?

Starting point is 01:30:16 You have to lead by example, so hopefully you're doing the same thing. And similarly, when we're talking about anger and these other emotions, I 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 if I were thinking about my own problem, because I'd be too wrapped up. What's the Carl Jung quote? That understanding the darkness in others is, or understanding the darkness in you and others, it's like transferable, right? Like all of these insights we get.

Starting point is 01:31:00 And I think the other piece here is just that don't measure initiative based on stuff within the field you're hiring the person for. Recognize that initiative is transferable, that past initiative is the best indicator of future initiative, and be a little liberal with how directly applied it is. I mean, a couple of the things on the assembling the crew front that I 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. 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, Tristan Walker, who's an entrepreneur, you know, started Walker Brands and has built a real business. He talks about how he grew up, he had a tough upbringing, and he feels like one of the things

Starting point is 01:31:53 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, it sounds nice, but why does that really mean? And he said, only with courage can you practice the same values consistently. So true. Yes. Yeah, it's like the meta prereq. Sure, because otherwise you're always making exceptions, you're always deviating. But if you

Starting point is 01:32:14 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 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, 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 back back in the day when uh actually there were snapchat and other products that were more about facials and whatever but or uh yeah not facials that's a difference yes yeah photographs we were in the sauna um yes so uh um selfies selfies yes it's the heat i'm telling you it's hot it's hot so uh it's so hot we'll have to take a

Starting point is 01:33:02 break and my thermometer has been broken for the last year. And this mic I can barely handle anymore. But anyways, so when I met with that team, and 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, 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 time I had a conversation with Kayvon and his co-founder, Joe, it was always like a step function more interesting than the one before it.

Starting point is 01:33:32 And I remember juxtaposing that with most conversations I have that are sort of replays. By step function, you mean dramatic improvement in this case? Dramatic improvement, difference, and every conversation being like, whoa, new level, new plane, new plane, new plane. And then now having gone through that investment from the whole period of seed through product market fit through acquisition by Twitter, I think one of my beliefs is that it was that chemistry with them that actually kept me engaged and also kept their team engaged with them. It was just one of those traits, again, that I actually try to look for. So I actually try to meet candidates

Starting point is 01:34:06 for senior roles twice. And I try to do a delta comparison between the first conversation and the second. And oftentimes it's the same. People are like, why am I here again? I answered these already. Yes. And I haven't done any additional digging.

Starting point is 01:34:19 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. 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. And here we are back in the whining cylinder in the truth barrel.

Starting point is 01:34:44 And I thought we might chat about now that we've lowered our core temperature, just a wee bit, a wee bit, a wee bit, uh, 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,

Starting point is 01:35:06 meaning a point or two. And then, uh, what a lot of people would love to hear about because you're so known for it, I think is, is product. And then we can move, uh,

Starting point is 01:35:15 from there, see where the wind takes us. Yeah. Yeah. I mean, on the, on the, um,

Starting point is 01:35:21 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 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 one of the little insights that I thought quite a bit about was the fact that your true blind spot is how you appear to others. And I think that part of that is understanding that

Starting point is 01:35:54 we react, obviously, for all different sorts of reasons to things. We react based on the confidence we have from the financial security we may or may not have. We react based on the confidence we have from the financial security we may or may not have. We react based on all sorts of other factors 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 interprets us 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 what some of those, what are the things that we're doing that we don't even realize that other people see and scratch their heads kind of thinking about. I remember this experience I had in high school

Starting point is 01:36:43 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. How old were you? Junior year of high school.

Starting point is 01:37:01 Were you piggy? Potentially. And super thin, but yes. But one of the most intense exercises that we did towards the end that I will never forget is this thing called the mirror exercise, where you pair it up with somebody, and they would tell you what they saw. Of course, from their experience having lived with with you 24 seven in a farm in Vermont. And, um, you know, that wasn't a physical thing. It was like, what I see you afraid,

Starting point is 01:37:31 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 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. 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? 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

Starting point is 01:38:14 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, cause something 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 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,

Starting point is 01:38:58 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, 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 the fact that, okay, hey 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 right yeah you're looking in the mirror but like you said i'm in the blind spot very literally like a car

Starting point is 01:39:37 where there's just this empty pocket that you cannot see 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 have well a few questions related to that uh first to the exercise is there anything and it's a long time ago i realized that the counselors or leaders of the group said to everyone so that they would receive yes without becoming defensive actually which would be the natural response for a lot of people, myself included, probably. Yeah. It's a good question.

Starting point is 01:40:09 And I think that it reminds me of like one part of it that I omitted, 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. So could you pass me your water now that I've extinguished mine? Yes. And I will selfishly put my self preservation ahead of yours. Please continue. Thank you. In your Casa. But, you know, I think that that was, it was somewhat, because you know what that direction did? First of all, it made people

Starting point is 01:40:35 realize that if I tell someone this because I'm judging them and they don't hear it from others, I'm going to look like an idiot. So it had a preventative measure in that sense. It also helped, um, the recipients discount anything that they heard once. Maybe it's psychologically still hard to do it. Very helpful. It was a very interesting trick. Uh, have you ever done a, uh, experienced a three 60 interview? Uh, okay. So for reviews, you mean, right? Yes. Three 60. Yes. Sorry. Three 60 review. Now it's my turn to 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.

Starting point is 01:41:23 Yeah, man, you're telling me. And I don't want to mention names. The very people you would view as maybe not immune to criticism, but certainly these stalwarts of strength, these 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.

Starting point is 01:41:55 But what it generally entails is someone wants to figure out these blind spots, 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 and so on and so forth. Maybe suppliers, distributors, who knows people you interact with a fair amount. And, uh, it's, it can be very sophisticated process. You can do this. I actually did a very early version of this.

Starting point is 01:42:30 It was really truncated in high school because I read a book called mental toughness training for sports by Jim layer, L O E H R. Who's in the last two years become 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 would it made a huge difference in my success as a wrestler it was really remarkable just to see from like the day of receiving answers which i received myself yep to next day, it was really astonishing how much things changed.

Starting point is 01:43:08 And with the three 60 interview though, just to come back to this, uh, only pay attention if it comes up more than once. Uh, 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,

Starting point is 01:43:25 because you're seeing these ugly truths, especially the ones that come up more than once. You're like, all right. Yeah. And the answers are anonymized, which gives people another layer of permission to be particularly direct. And,

Starting point is 01:43:38 uh, 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. Uh, 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, 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 three 60 review and you'll find all sorts of resources.

Starting point is 01:44:07 I've never seen Tim fully celebrate anything. And it relates back to what I mentioned earlier. It's always looking for what's wrong. 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.

Starting point is 01:44:24 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 or undeserving of that but in retrospect very painful pill to swallow but they were absolutely right i mean it's crazy to think but at a certain point and i don't expect anyone to cry me a river on this stuff but it does be lie some type of real psychological issue that i had to address but i remember the last two times i've had a book uh do very well on the bestseller lists i I mean, like the first time it happened, like game-changing, collapse against the wall,

Starting point is 01:45:07 fall on the floor, I can't believe it, dazed for the rest of the day, maybe the rest of the week on Cloud9. And at this point, I feel like it's the expectation that my books will do that. And certainly it's the expectation of the publishers. And it's just relief that I didn't fail. And maybe I'll have one drink,

Starting point is 01:45:23 and then it's like, all right, on to whatever you should be doing next. That's awful. Uh, so 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 a form of arrogance. Or 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.

Starting point is 01:45:55 Again, back to that mirror exercise, unexpected things you might see that people see. Yeah, for sure. And also, I mean, at least in my own reflection, 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 and have adopted, but I'm playing their soundtrack. Yes. I did not decide to have that voice. And 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 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 i'm gonna suggest that we tap

Starting point is 01:46:58 out and go sit outside where it's cooler thank god yeah i was gonna thanks so so we were going to say i don't have the physique of tim for those of you can't see it doesn't seem to help with my my heat talks so we're gonna we're gonna keep recording and just walk out uh it 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. Stars. Stars, fire pits. This will be the third setting.

Starting point is 01:47:29 This will be the third setting. We're doing a lot of costume changes and a lot of scenery shifts. This is good. This is good. You know, I think that crickets, insects, and birds at night is a perfect setting for product talk. My favorite topic. Where shall we begin? 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

Starting point is 01:48:06 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 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

Starting point is 01:48:41 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 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 achieve a lot very quickly.

Starting point is 01:49:10 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 adopting that technology because it was just like, hey, it's selfish. I'm going to get this done quickly. I don't even care if it's as good as the homegrown solution. And vanity comes across in every consumer product you see

Starting point is 01:49:33 with those ego analytics, those hearts, those things that tell you that, oh, wow, 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— Onboarding meaning the sign- process exactly like the signup process or walking into the store knowing um when you when you go into any product experience why are you there where do you go next what's possible um now the pushback i get from a lot of great you know companies and teams and whatever hey, I have more faith in people.

Starting point is 01:50:08 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. You know, so they appeal to that like immediate need of I want a collection for myself before recognizing the value of other people's content. And there's just, there's so many examples of teams. You know, another product thing I think a lot about is back to that kind of onboarding first time user experience is, um,

Starting point is 01:50:46 you know, 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, a lot of products that really do succeed quickly actually give you like a template. They just like actually do it for you. They make you seem so much better than you are with stock content or whatever it is. Um, so those are just like 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. How do you stress test, say, a first design after you've assuming the team has accepted those commandments or those realities and they they think they've designed for it how do you stress test it well there's a few um there

Starting point is 01:51:34 there's there's first of all the classic metrics of our people getting their way through what's catch what's catching them up you know i remember 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, you know, little things like that. But I think that, but it really comes down to like empathy with the newest user. Are you bringing people in and watching them on a computer or are you using a contracted service some type of online service to record craigslist what are you doing 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,

Starting point is 01:52:25 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. And yeah, I mean, I think that there's a lot of mechanisms to measure the effectiveness of First Mile. The thing is, though, it's actually not as simple as just solving it. 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.

Starting point is 01:53:06 That is a cohort of new users. Then word gets out, people start to use Twitter who, you know, 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, you know, I don't have the tolerance for that. 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 like kind of reinvent that first mile. It's not like you get it right. And then it's like, move on, which actually most teams do. And so that then relates to the newest customer

Starting point is 01:53:50 paying attention to the latest cohort. That's the reference. Yeah. It's consistently committing a 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, you know, they're willing to go along with some bugs and whatever. You know, 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.

Starting point is 01:54:29 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. 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 got to 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,

Starting point is 01:54:54 they're just going to 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 going to make. 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,

Starting point is 01:55:15 I really feel like we would be equally happy 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 going to show up a lot of resources yeah how do i choose well i think that there's there's two answers to that you know one is um 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 meaning mock up mock ups sorry and um and you uh you you test and you build some of the marketing copy, like welcoming, and you just give like a design and experience,

Starting point is 01:55:52 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.

Starting point is 01:56:15 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. 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?

Starting point is 01:56:43 Not only do you make up mock-ups and show people and test how the marketing company 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, hey, we'll ship a minimum viable version and then we'll just iterate to a great place. So what was the word you used?

Starting point is 01:57:17 Local. Local maxima. In the sense that you're anchored. You're anchored, right. To that version of the product in some way. 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

Starting point is 01:57:33 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 mock-ups, the stuff we discussed earlier. But then you build something that you truly believe

Starting point is 01:57:55 has a shot at delivering that value to customers and take the extra time to perfect the few differentiating factors that are most special about it. Yes, you can cut corners around all the 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

Starting point is 01:58:14 whether or not the conviction you have is the right one. 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 uh 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 a second even within software software, it applies most, I would say, to products that are a unique solution to a pressing problem.

Starting point is 01:58:57 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. Yes. 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, that approach may not always be the best approach.

Starting point is 01:59:25 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 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, right, is, actually, let's talk 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, including some big ones, including

Starting point is 01:59:57 some big ones like Uber. And he, you know, one of the things that, that I've learned from him over the years, and I've seen in some other, successful founders, is this notion of building the narrative before the product. We were just talking about which product do you choose. Sometimes it actually helps to say, hey, what should the splash page be and what should the brand be before we even get the team together? I mean, let alone start building something or coding something in a digital sense. We talk about the notion of product market fit, right? When customers are getting the value. We talk about the notion of product founder fit when you find the right team to build something.

Starting point is 02:00:40 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 a CEO of his company stumble upon, he was kind of drafting out the concept of Uber. And, and I remember him obsessing over the icon, 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 an aspirational brand, like everyone's private driver? Or is it an accessible brand, like taxis on demand? And if you think about that it's like wow like these

Starting point is 02:01:26 are questions that he was asking before this was this technology was even coming together or even validated right yeah carrot uh is a is very exceptional human and founder, uh, who, who really telescopes out very, very far in the earliest stages. And I remember getting one of the very, very early mock-ups. Uh, this was, this was before the app was deployed, even with one car, the screenshots, you know, these, these comps, as you mentioned, 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? He was thinking global already. He was thinking global. He has a very good playbook. It's also though, I've had conversations with him about brands for other companies that he's been working on. 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.

Starting point is 02:02:37 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, Scott at spot.com or would you rather have Scott at discover spot.com? You know? And, and so he was also thinking about from like the product brand fit perspective, is this something that people can grow into that people would want to work out at and say, like, I work, you know, this is my email address.

Starting point is 02:03:11 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

Starting point is 02:03:33 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, exactly. That's the point. Like put that together as a starting place. Cause it, you know, it helps get alignment very quickly,

Starting point is 02:03:52 which is a magical part of product development is when you have alignment versus not, uh, two different, two different ball games. 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, uh, 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, uh, Maxim that you could share? Right.

Starting point is 02:04:31 Well, 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've 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, in any major, in any journey. But I really, I think that this notion of the final mile of

Starting point is 02:05:00 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. And in this context, the end, are we talking primarily about acquisition or IPO? 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, 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,

Starting point is 02:05:45 um, that he, uh, was really excited that, um, one of these big kind of Google Facebook like companies was doing their diligence on his, uh, on his, on his company. I was like, Oh wow, that's really exciting. Um, 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. So you must have a, an offer on the table. Like what, you know, what's the value met the team i'm like oh they've met the team so you must have a 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 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 a 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?

Starting point is 02:06:26 And as the conversation unraveled, he realized he had no idea what he was doing. And for him, it was like business as usual. And that's one example where that people psychologically start to wonder whether they deserve the success they're about to get. I remember a story in my own experience with Behance, there was a 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 and just starting to act out a lot. And I remember confronting him a couple 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.

Starting point is 02:07:32 And she's like, oh, this is self-sabotage. I'm like, what? 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 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

Starting point is 02:08:08 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 there was this connection we had where he sort of looked at his behavior as maybe something else. And I think that happens a lot. I think that there is this, things do break down in the final mile. A lot of stuff changes psychologically. Artists, right? How much churn happens right before they ship?

Starting point is 02:08:47 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,

Starting point is 02:08:58 where it's like, wait a second, not ready to ship yet. So this is classic. And you have to be prepared for it. Yeah, I mean, overwriting 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 yes and yet you know that there are probably things that could be improved still you start to fuss yeah with in in many cases no particular direction or means of assessing your changes but you know there are things to be fixed or improved upon

Starting point is 02:09:40 uh yeah i would imagine it happens in a whole lot of contexts. I think it does. And, and, um, 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. 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. Um, and, uh, part of it is recognizing that the tactics that you employed all along suddenly may either be wrong or even detrimental. Um, it's, it's really, this is a new game and you

Starting point is 02:10:22 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, um, uh, 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. 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 I realized in that process I had no idea what I was doing.

Starting point is 02:10:51 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, it becomes part of your identity. You become kind of known for something and you have to decide, is that going to be me or am I going to start to reject that and put it behind me? And you'll hear some creatives and especially artists say that they just like to kill their old work. They like to do something completely different. Otherwise, they feel like they're attached. 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.

Starting point is 02:11:32 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. Yeah, super challenging. I mean, that makes me think of my first and second book. I mean, I could have done the three-and-a-half-hour final mile. Yeah. Super challenging. I mean, that's, it makes me think of my first and second book, right? I mean, I could have done the three and a half hour work week or a milked the four hour work week plus the four. I could have milked that thing, but I, I was, I was really afraid of having to give the same talk on email autoresponders until my dying day. As much as we would all like email to die,

Starting point is 02:12:07 I don't think it's going to happen anytime soon. And I'll say I made the, it was not an easy decision for me, but because I had no evidence that I would be able to write about a different topic. It was my first book. 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 not going to disappear after a year, if I deserved it and it was still here in that as my identity and then correspondingly develop a risk intolerance to trying something different. Uh, but that was hard. It is.

Starting point is 02:12:55 And it's, and it's also, if you look at it from a business perspective, um, 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, you, that'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,

Starting point is 02:13:14 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, um, and it's, you know, and, scale. And they see their career in that way as well. It's like, I'm not just going to be the enterprise SaaS guy. I'm not going to be the this. I'm not going to be the that. I'm going to actually kind of find another edge, find something different, keep it fresh.

Starting point is 02:13:39 And that's admirable because it's not the path of least resistance. 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,

Starting point is 02:14:21 some of the stories based on experiences you've had and that you've had imparted to you from mentors. Uh, you've taken all of these notes, those that made the final cut. What is it? 120? Just about. 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?

Starting point is 02:15:02 This is the final subtitle. No, no, no, that's fine i just 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? I think the need is clear. I'm excited about it. As you said, it really was that process of the 800 and something notes 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.

Starting point is 02:15:49 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 then I'm trying to also, though, like continue these as conversations. You know, on Twitter, I'm just at Scott Pelsky. 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 what this book has become. So I think that we're all in our own messy middles. And I just hope that this helps people know that they're not alone as they're in the enduring phase and managing

Starting point is 02:16:26 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 here here well scott thanks for the uh endurance of this marathon across multiple types of scenery uh within certain types of scenery i'm not gonna lie as intense at different temperatures uh maybe in some ways like the messy middle here There you go. 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,

Starting point is 02:17:17 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 forward slash 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. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is

Starting point is 02:17:46 Five Bullet Friday. Do you want to get a short email from me? 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. It's just a little tiny bite of goodness

Starting point is 02:18:26 before you head off for the weekend. So if you want to receive that, check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.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, well, WordPress lead developer, CEO of Automatic, Matt Mullenweg, now valued at more than a billion dollars, have used LegalZoom to help with their business needs, specifically in his case, to form his company.

Starting point is 02:19:01 But LegalZoom isn't just for launching your business. Their services include everything from helping you to manage changing tax laws, reviewing contracts, creating NDAs, non-disclosure agreements, important stuff, handling lease agreements, and assisting with really any other legal challenge, hurdle, inconvenience that typically takes time and effort away from running your business. The best part is that you won't get charged by the hour because LegalZoom isn't a law firm. So they won't be running the clock up and spinning circles just to raise your bill. Instead, they just ask you to pay one low upfront price for whatever it is that you're looking to get a la carte style. So visit LegalZoom.com and

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Starting point is 02:20:25 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 you're 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. You can set yourself up to receive online payments from your clients in about two clicks, which on average will get you paid twice as fast. Their new proposals feature means you can include a project summary and timeline as

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The Tim Ferriss Show - #336: Scott Belsky — How to Conquer the Messy Middle

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The Tim Ferriss Show - #336: Scott Belsky — How to Conquer the Messy Middle

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.