The Tim Ferriss Show - #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life”

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Starting point is 00:01:36 This episode is brought to you by Shopify. Shopify is one of my favorite companies out there, one of my favorite platforms ever. And let's get into it. Shopify is a platform, as I mentioned, designed for anyone to sell anything anywhere, giving entrepreneurs the resources once reserved for big business. So what does that mean? That means in no time flat, you can have a great looking online store that brings your ideas, products, and so on to life. And you can have the tools to manage your day-to-day business and drive sales. This is all possible without any coding or design experience whatsoever. Shopify instantly lets you accept all major payment methods. Shopify has thousands of integrations and third-party apps, from on-demand printing to accounting to advanced chatbots,

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Starting point is 00:03:56 slash Tim. One more time, shopify.com slash Tim, all lowercase. Optimal minimum. At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? Now would have seemed an appropriate time. What if I did the opposite? I'm a cybernetic organism, living tissue over metal endoskeleton. The Tim Ferriss Show. Hello, boys and girls. The Tim Ferriss Show. very fun, very wide-ranging conversation. Derek Sivers. Derek Sivers, you can find him on Twitter at Sivers, S-I-V-E-R-S, is an author of philosophy and entrepreneurship, known for his surprising quotable insights and pithy, succinct writing style. He has revised his bio. I love this.

Starting point is 00:04:56 And this ties into what we talk about in the actual podcast. He is a former musician, programmer, TED speaker, and circus clown who sold his first company, CD Baby, for $22 million and gave all the money to charity. Derek's books, How to Live, Hell Yeah or No, Your Music and People, Anything You Want, I love Anything You Want, and newest projects are at his website, sive.rs. And you can also type in Sivers.org and it'll go to the same place but he likes the s-i-v-e.r-s and there are two urls that didn't exist when we recorded but he promised to create pages for them and he has so the first is a page for his newest book useful not true and that is at sivers so. So S-I-V-E dot R-S slash U. And the next is related to tech independence. So how do you get off of the cloud, create your own tech independence,

Starting point is 00:05:53 and you can find the details, the step-by-step at Sivers slash T-I. So again, that is S-I-V-E dot R-S slash t-i. And without further ado, please enjoy this very in-depth, very eclectic conversation with the one and only Derek Sivers. Should we kick this party off? What do you think? Ready. All right. So I thought we would start.

Starting point is 00:06:21 First of all, cheers. Cheers. Thanks to Matt. Yes. Matt Mullenweg, thank you for the scotch blend, which we shall enjoy here. So I'll take a sip first. Ooh. Mmm.

Starting point is 00:06:35 We have scotch. We have go-go gadget black tea. What is this called again? Go-go-goa. Go-go-goa. Yeah, go-go-goa. It's so good. So we have go-go-goa. Like Goa, goa. Go, go, goa. Yeah, go, go, goa. It's so good. Go, so we have go, go, goa.

Starting point is 00:06:45 Like goa India, you know, the region. Yes. So this is otherwise known. I do have a backup of Diet Coke in case. This is Podcaster Speedball. So I expect this is going to be a fantastic episode. And for those who are not watching or those who may not have video in front of them, we have two different sized scotch glasses.

Starting point is 00:07:06 And if you were to walk into Derek's kitchen, you would find a wide assortment of glasses, namely one other glass, which is yet larger. It's like a Russian nesting doll of three separate glasses. And those are the only glasses you have in the house. And I didn't buy any of them. They were just... So please explain more.

Starting point is 00:07:28 Oh, God. Because you walk the talk of certain types of minimalism. There are those out there who may not believe some of it. I'm just saying, or maybe skeptical. Have a healthy skepticism. I'm telling you guys, he's got three glasses in his kitchen. And this is my only pair of pants. And yeah, so these three glasses, I don't even think about it because I just think about having what's enough. Yeah. Right. So there's only me and my kid here. And so you come over and you say, okay, let's make some scotch. And you're like, do you have any? I was like, uh, no, that that's all I got. I just have these

Starting point is 00:07:59 glasses. And honestly, I don't even know where they came from, but they work. They work. And this is enough. And these little bamboo cups I got for my kids so that he wouldn't break them. So I have a feeling we will come back to this in a sense, because as a foreshadowing for people who are listening, if you have not read The Paradox of Choice, Barry Schwartz, he talks about maximizers and satisficers. So I think we'll probably come back to this in a bunch of different ways. But suffice to say, the embodiment of minimalism. You also have two very nice suits that act as your sort of outside-in-the-world attire,

Starting point is 00:08:36 which makes sense to me. And only two. Again, it's this idea of enough. It's like I wear junk, basically home pajamas. I think of one of those pajamas, the big baggy t-shirt that somebody handed you to conference. And you would never wear that outside the house. But Michael Brown with an E in London, when I lived in London, right before COVID hit, I thought, you know, I'm living here by Savile Row in London. I'm about to leave England forever. I'm going to get a custom-made suit.

Starting point is 00:09:06 So I looked at, what was his name? Sartorial Talks. It's an interesting YouTube channel about somebody diving deep into, like, the craft of fine clothing. Tailoring. Yeah, tailoring. And so he recommended this guy, Michael Brown, in London. So, you know, I went to Michael

Starting point is 00:09:25 Brown and he said, what would you like? I said, you're the expert, you know, just dress me. So he told me what to wear and I do. And because I have a little bit more context here, then he would ask, so what type of shoes are you going to wear? And you're like, what should I wear? Well, how are you thinking about X? And you'd be like, how should I be thinking about X? And this is something I've thought more and more about, which is it's not so much quantity versus quality because there's a whole spectrum, right? You can have things that are very good and you have half a dozen of them. I'm making this up, of course. You can have one thing that is the best subjectively or objectively and that's it. You have have one or you could have a ton of things and you're like hey i don't care about this thing so this is a disposable item or service

Starting point is 00:10:14 or fill in the blank in my mind so i think we'll probably talk more about this but what comes to mind for me also when i think about say your suits, your suits, they're great suits. You're happy with them. You look good in them. And I think about, in contrast, my accumulation of ill-fitting suits, in part because my body weight has fluctuated so much in my life, right? I've gone from 145 to 220, in both cases being pretty lean. So I have like kind of fat boy Tim jacket, and then I've got like really, really skinny emaciated Tim jacket, and then I've got things in between, but I don't need most of those. And yet I still have them or not from the perspective of fit, but Kevin Kelly in his new book, which is, I think it's simply called excellent life advice, something like that.

Starting point is 00:10:57 And one of the bits of advice was along the lines of, yeah, you know how you have that bad pen. He's like, throw out the bad pen. It's so liberating. how you have that bad pen? He's like, throw out the bad pen. It's so liberating. Don't have the bad pen. Yeah. It's about self-respect, isn't it? Yeah. Even something as simple as a pen, when I've done that, I went, I'm better than this. I'm not going to make this. This pen is not going to rule over me any longer.

Starting point is 00:11:19 Yeah, yeah, yeah. You're only as good as the worst pen in your house. So let's start with a story. And I have not heard this story because you began telling me, and I said, no, I don't want to hear it. I said, let's save it. Scuba diving. Scuba diving? Scuba diving. That'll be my cue.

Starting point is 00:11:35 And what it taught me about empathy and identity. Amazing. I'll listen to the TED Talk. I'm sold. There you go. I'll listen to the TED Talk. I'm sold. So I was in Iceland, and I never had any intention to go scuba diving. But I was at that place in Thingvellir Park, if you've ever been there, where the two continental plates meet. The American continental plate meets the Eurasian continental plate. And there's this deep fissure in the ground, but it's crystal clear water, so you can see all the way down.

Starting point is 00:12:04 I'm like, ooh, I it's crystal clear water. So you can see all the way down. I'm like, Ooh, I want to go in there. It just looks like avian spring water, you know, poured over rocks with nothing clouding the water. So I was in Iceland for a month. So I went to take scuba diving lessons and the instructor was great. So it's a dive.is at the time it was just him in his basement and it was me and one other guy learning scuba diving. So we did the practice in the swimming pool, and we did all the theoretical stuff. You learned scuba? Yeah. Okay. And so the swimming pool was great, and I love the fact that it's calm, that you don't

Starting point is 00:12:36 need to panic about holding your breath. It's just slow and meditative. But then the first time we went into the cold ocean, and to be clear, I had to wear one of those giant dry suits. You're like a spaceman with four layers of rubber and stuff over the rubber. So it's very claustrophobic. And then I get into the water and it gets down to about 20 meters. And I'm just like, Oh God, do I hate this? I hate, I want to like, I need to go. I need to, I just want to go back at home. I want to be on the internet. I want to be emailing my friend. I want to talk to my friend. I just want to, you know, I just, I got to get out of here. So I wrapped on his tank and I went up to the top.

Starting point is 00:13:07 You point it, you point it to go up. Yeah. And I was just like, I tore off my mask and I was just like, I said, I don't want to, I said, I'm just going to go, you guys go ahead. I'm going to wait on the side there. I'll just, you go ahead. I'll just wait. And he was so sweet. He was so cool. He looked at me and just stopped for a second. And he said, hold on a second. He said, it's a really nice day today. He said, look around, look at those mountains. And he goes, see, it's a nice day today. He said, yeah, look, look at what a, look at what a beautiful area we're in right now. See, um, and then he said, you know, if you were to leave now, he said, I know you're flying back in seven days. If you were to leave

Starting point is 00:13:44 now, you wouldn't be able to complete the training. And you wouldn't get your certification. I know you don't want that. He said, just relax for a second. It's all right. And so I just relaxed for a second. You know, you inflate your BCD, so you're just buoyant and you float. And I went, all right.

Starting point is 00:14:01 Yeah. What was I scared of? So I went, okay, I'm ready. And so we go back down and I completed it and it was great. It was no problem. And I love being underwater. It's wonderful. So that was the completion of my training. The next day was my first official dive. So we're there with a dozen other people that have flown to Iceland from around the world, including this couple from Germany that were bragging about how many dives they've done. We've done over 100 dives.

Starting point is 00:14:26 So they were acting like know-it-alls, but then they're like, oh, dry suit. We've never done dry suit before. And so they're getting into dry suit. Yeah, it's tough. It's different. It's different. And so I get underwater, but this time I'm elated. I'm underwater just where I wanted to be in that crystal clear

Starting point is 00:14:46 fissure there in thingville i was like wow and at 20 meters down which is for the yanks 60 feet or so yeah i just pretty deep i mean that's that's that's a deep dive bottom of where you're supposed to go as a beginner and at the bottom i see the german girl by herself. And her partner's not there. And I do the dive manners we're taught, where I gave her the okay symbol. Yeah. And she gave the not okay symbol. And I was like, oh, wait, did I remember? And I was like, okay?

Starting point is 00:15:16 And again, she goes, not okay. And I see her eyes are looking crazy. And I went, oh, shit, I've been trained for this. Oh, my God, I can do this. Okay. Held on to her BCD, held held onto mine, inflated hers a bit, asked if she needed my mouthpiece. And she said no and helped her get up to the surface. And she gets up to the surface and she rips her mask off just like I did. She said, I don't like this. I don't like, no, this is not good. I don't,

Starting point is 00:15:39 I hate this. I feel bad. I want to go. And I said, I just imitated the dive instructor. Exactly. I said, well, hold on a second. I said, look around. I said, it's a really nice day. I said, isn't this great? I said, do you see those mountains over there? I said, just relax a second. I said, I'm here with you. It's okay. And so she calmed down and I saw her go do the same thing I did and calm down. And then her boyfriend showed up. Where the hell was the boyfriend? I don't know. But he took her away. You're on your own, babe. I'm out of here.

Starting point is 00:16:16 I've accidentally missed one step in the storytelling of this that I should have included is the night in between those two days, I went home that night thinking, what the fuck? I think I just had a panic attack. I'm not one of those people. Like, I have no respect for people who have panic attacks. Because usually, panic attacks, to me, I think of, like, people who are just like, oh, no, like, my cake is late. I'm going to die. And they freak out over shallow little things. And it seems to me like they have no perspective on life.

Starting point is 00:16:44 So then I have no respect for that kind of silly panic. But I had just panicked. And it was involuntary. It's like that night, I had this moment of just like, wow, what does that mean? Am I a panic attack person now? Have I changed categories from a not panic attack person to a panic attack person? I just kind of fell asleep with no answers to that. So then yeah, then the next day, had this thing happen with a German couple. And I feel like that experience taught me two kinds of empathy. That we categorize people, like I just said, the type of person who has a panic attack.

Starting point is 00:17:19 And we think of a category of person that's, say, like, depressed, fat, homeless, divorced, bankrupt, and you think, I would never be those things. I'm not that kind of person. But I thought, wow, like a lot of these things are involuntary. It's not like somebody chooses to be depressed. And I realized I had been unfairly categorizing people the same way I had unfairly categorized panic attack people. Because now I am one, right? I've had that. Addiction.

Starting point is 00:17:51 Somebody who said they would never be an addict. Then they find themselves addicted to something that seemed harmless at first. And they have to admit, oh my God, I'm an addict. But then I realized that someday these categories might be me. Or anybody else, if you're categorizing people these categories might be me or anybody else. If you're categorizing people, this might be you. But then the thing that happened on the second day, where there's another category that we don't think we could be, which is like hero, rescuer, leader, athlete. Things with a positive connotation.

Starting point is 00:18:22 Millionaire. Some people in the past few years have become millionaires, which is something that they held in a different category. And thought, I'd never be that. And suddenly they're, you have to admit, I'm a multi-millionaire now. It's a category. So I realized that we can, even those categories can be involuntary. That you can suddenly be a rescuer, even if you never intended to be one,

Starting point is 00:18:43 just through the power of imitation. So you can deliberately step into these roles by imitating others. So how do you now think about labels that you apply to yourself? And I ask that in part because as you're speaking, I think of how it can not only be unfair to say, I'm this and not that, or that person is this and not that. But if you're applying it to yourself and you have very narrow categories, so you have very finely tuned labels, I think it makes you fragile. Because you are susceptible to the whim of chance in a way that I think is not particularly

Starting point is 00:19:31 resilient. If suddenly your circumstances change and you find yourself in a different category, it can be really upsetting. And how do you think about what you call or don't call yourself? We were talking a little bit about this at lunch before we recorded, right? There are people who are like, I have read Stoicism and now I am a Stoic. And there's this identity that's assumed and these labels that are applied. And as much as I love Stoicism, even though I invoked that name, I do think that you have to be careful with labels. So how do you think about that for yourself?

Starting point is 00:20:07 Well-timed for a sip of scotch. Well, young men. Sit down. You sit down. By the way, audience, the hardest thing about hitting record on this is that Tim and I have these like crazy all over the place conversations in the forest and whatnot, that it's hard to remember that we need to close

Starting point is 00:20:25 tangents today. Usually we open a tangent and close it two days later. We need to close tangents today. So do you want me to go on my anti-ism tangent? Well, let's see. Is there some unfinished business that we need to tidy up first? There's a tiny idea around the identity, which is to just admit that whatever you are is now and whatever your preference is now. So like when my kid says, I hate tomatoes, I say today. And he goes, oh, right. I hate tomatoes today because it's leaving open the possibility that you might change your mind tomorrow. And he did. I hate olives. I hate, hate, hate olives so badly. You, Derek. Okay. And he picked this up from me, right? So he's like, I hate olives too, but he was just imitating me.

Starting point is 00:21:11 And then we went to Subway one day. I was so proud of him. He walked up to the counter and he said, I would like olives. And they said, do you want anything else? He said, ham, just ham and olives. And they loaded this sandwich full of olives. And I looked at it like horrified. He ate it and loved it. And he goes, I like olives now. It's like, yes, I love that switching between identities. And so I used to call myself an entrepreneur

Starting point is 00:21:39 and other people would call me an entrepreneur. And then I did my first book that was about that. So I got categorized as an entrepreneur. Great book, by the way. Thank you. Thank you for the full word. Anything you want, right? Yeah.

Starting point is 00:21:50 Yeah. I recommend people check it out. I've read it multiple times. It's a great book. I love that you did the full word. Yeah. Thank you. Yeah, you're welcome.

Starting point is 00:21:58 For years, I kept calling myself an entrepreneur until one day I realized, like, wait a second. This has expired. Somebody who was an athlete in high school can't keep calling himself an athlete forever. Yeah, I've learned that one. You have to keep earning that title or it expires, right? Same thing with being a good friend. It's same thing with any labels that we call ourselves. You can't just keep using that forever. You have to keep it up or it expires. So if you realize that your previous identity is expiring, you have the choice then of either admitting, I was an entrepreneur, I was a musician, or if you don't want it to expire, well, then you need to do something

Starting point is 00:22:39 about it and then go actively be a good friend, not just keep calling yourself a good friend, or go actively be an entrepreneur if you want to keep calling yourself that. So I may be skipping ahead because I do like mixing tangents. Great. But that's the nature of conversation, especially when you have go-go gadget tea and scotch involved. We were talking about this the other night at dinner. Revising, say, we use language, we're creatures of language. I mean, part of the reason that we've become such a dominant pest on the planet is our ability to

Starting point is 00:23:12 use concepts and abstraction. And you'd mentioned at one point, thinking of yourself after entrepreneur as a writer. How did you make that switch? Looking to your heroes. I call it my people compass. If you're not sure which way to go, you can ask yourself, well, who do I admire? Who do I like? So for me, this was like, as I was not sure what direction I wanted to go, I am an entrepreneur and I'm a programmer and I'm an author. I actually thought about it in that order, maybe programmer first, entrepreneur, and then writing seemed to be something I was doing as just like a waste product. A metabolite of your other focus. It was like, and as I'm doing my thing, if I learn some lessons, there, I just put them into writing.

Starting point is 00:24:08 But then I noticed that all of my heroes were authors. These were the people I looked up to the most. And that helped me realize my values. Like, it helped reveal my values. So ultimately, like, we want to be our ideal selves. And I think that your heroes are your idealized self. It's kind of, that's why we idolize certain peoples. We want you to be like them. So that kind of reveals what your values are.

Starting point is 00:24:32 So in that moment, I went, oh my God, that's right. In my heart, I'm actually more of an author. And programming is fun. I love programming. I love what it empowers. And I think we're going to talk about that later. And I'm not an entrepreneur anymore. So in that moment, I was like, that's it. I'm really an author now, aren't I? Wow. That feels weird to me. I never thought of myself

Starting point is 00:24:52 as an author, but I think this is the reason I call it a people compass is it's related to when you're not sure what business to start. A lot of people are, they're looking at the many different options right now. The way I think about it is asking yourself, what kind of people do I like being around? Because these are the people you're going to be serving. You have to like them. You want to love your customers and love serving them because ultimately, even if it's the money, what you really, really want is the emotional fulfillment, right? Yeah, totally. So you might get lucky by strategically choosing an industry or a market that's on its way up. And you might get lucky by strategically choosing an industry or a market that's on its way up, and you might get really lucky and become a billionaire doing something.

Starting point is 00:25:30 But what if your customers are jerks? Would you be happy getting rich running an all-night vaping store? If you think of the kind of customers that would come into your all-night vaping store, are these the people you want to serve? And would you be happy even if you made a million dollars doing that i think you'd you'd feel pretty mixed about you i'm a little embarrassed to tell you about my new startup then right so it's asking yourself like what kind of people do you want to be around decentralized blockchain baby seal clubbing expeditions yeah yeah not not sure i want to hang out with the people who might go on that tour. Run by AI.

Starting point is 00:26:08 We may need a refill on the scotch at the rate we're going. I don't know how that's going to work. Pause. So, yeah, I think that if you set up your business to serve the people that you love being around, even if it makes less money, you're going to be much happier. So that's where

Starting point is 00:26:24 I'm at right now. Right now I'm not an entrepreneur, but I'm starting to get that itch. I'm starting to feel like doing something. And if I do, it'll just be to be around the people that I already love. Okay, so let's poke at that a little bit. Being around the people you love, there are many ways to do that. Why do you think you are maybe leaning towards the entrepreneur vehicle for doing that versus doing other things? Is it what you know? Is there more to it?

Starting point is 00:26:53 Because it's asking yourself, what would you do even if it didn't pay? Yeah. I'll just pick one example. And don't hold me to this world if I don't end up doing this idea. Do you know that like seven years ago, I happened to mention that that week we talked, I was enjoying learning the history of hip hop. And for six years, people keep telling me like, so history. I was like, it was just, it was that week. Come on.

Starting point is 00:27:14 So, all right, right now. And now I like olives. Stop lecturing me about my past self. So right now, an idea I'm having is 100 year hosting, legacy personal websites, so that setting up a trust so that your personal website will last on for 100 years or 50 years after you die. Yeah, sure. And this is the kind of thing I care about so deeply that I would do it even if it didn't pay.

Starting point is 00:27:36 I would do it as volunteer work. And I really like people that have personal websites. They're my kind of people that enjoy technology for its own sake, that took, what do you call that? Oomph, go power. Oomph, go power? No, no, no. Where somebody takes initiative. Is that English? Go ahead. I don't speak Esperanto yet. Somebody took a little and set up their own website. I like these people. I like people that have personal websites, that aren't doing it for money.

Starting point is 00:28:08 They're my kind of people. And so I would be proud to serve them. So that's all I meant by that. Okay. So many directions we can go here. I think you alluded to it, so why not hop to it? Programming, the empowerment that can provide. Let's talk about escaping the cloud, or broadly speaking, tech independence. And to set the stage for folks,

Starting point is 00:28:31 we were walking down the street here in Wellington, beautiful Wellington, New Zealand. Only central Wellington. New Zealand. Well, yeah, the central area is a little bit like Haight-Ashbury in some respects, but for the people who get the reference. But all in all, beautiful city. Lots of hiking trails, shockingly similar to Northern California. I mean, I felt like I was flying an SFO. You have Monterey Pine here.

Starting point is 00:28:54 You have Eucalyptus, which we both borrowed from Australia. You have nasturtiums. A lot of the vegetation here is similar. It's really nostalgic and kind of eerie in a way to be here because I feel like I'm back in Northern California. It's like being in a time machine. In any case, we were walking around, not on the nature side of things, but downtown. And I said, you know, I'd love to ask you about cybersecurity. And I said, let's say, and I'm not going to use anyone's name, but somebody who's very technical and hyper paranoid. I was like, let's say, and I'm not going to use anyone's name, but somebody who's very technical and hyper paranoid,

Starting point is 00:29:27 I was like, let's say there are 10. Let's say your mom is a one. Not to make assumptions about your mom, but I will. Where do you fall on the cybersecurity spectrum? And that opened up a, I think, fun discussion. We chatted. You also then wrote in your diary about it the next morning. Yeah, because I'm slow like that.

Starting point is 00:29:48 You'll ask me something like that. And in the moment, as we're walking down Courtney Place, I'll give some half-assed answer. And then later that night, I'm like, ooh, I got a better answer. I mean, I'll push back a little bit. Slow is relative. I mean, I think that you were very coherent and you thought about it before you launched off into some type of monologue, which you didn't.

Starting point is 00:30:12 It was a conversation, but you then refined it the next morning. Yeah. So let's talk about this because you gave a couple of, I wouldn't say recommendations. You described a few things you do personally that I found very interesting. One of which was, you don't use the cloud, which I think will get a lot of people's attention. Because in part, I think there are many people who feel, myself included, that there's something uncomfortable about it. But I assume since I'm non-technical, there really just is not an alternative, but there is part of me that's very privacy sensitive and is fundamentally

Starting point is 00:30:51 uncomfortable with having all this stuff, all this miscellanea, all these impulsive, ridiculous group chats and whatever backed up somewhere else for a lot of reasons. Your phone book, your calendar, all of that,

Starting point is 00:31:04 all of that. All of that. It's there. There's something deeply uncomfortable about it. And yet I use the off the shelf tools because everyone else does. And I just assume there are no alternatives that are feasible for a muggle like myself. Poor Tim. Poor Tim.

Starting point is 00:31:20 Poor incapable Tim. All right. So Dr. Dr. Sivers, please, hold court. So, audience, I prepared. I took notes because, although I love Tim's podcast, I love it most when people come and give us, like, an intense data dump. Yeah. Know this, know this.

Starting point is 00:31:44 So, guys, I prepared a couple hours, and here you go. So, I'm going to unapologetically read from my notes to give you the best bang per buck of your time listening. So, tech independence is all about the fact that I think the main sales pitch of the cloud is, now, don't worry your little head about that. Let us take care of it. We'll keep all of your data. See, isn't that easier now? There, we've got your data.

Starting point is 00:32:08 And it actually reminded me of something I think you said in For Our Body about yoga studios. That no, it's not the best thing for your health, but it's a better profitable pitch for them to sell you a yoga studio instead of deadlift free weights. Yeah, there's a lot of that in fitness overall, for sure. There's an incentive. This is the tech equivalent of that. I wish that history had gone such a way that we all had our own little private server at home. But instead, the cloud made a better sales pitch, saying, no, no, no, give us all your stuff. We'll take care of it forever.

Starting point is 00:32:39 So my idea is, if you spend a few hours to learn how to do it yourself, you'll just have tech independence. What that means is self-reliance. It gives you better security, better privacy, better freedom, better flexibility, and total control. And I think it's a great use of your time to spend a few hours learning to do this. Kind of like somebody learning to drive manual transmission, right? You don't need to do it, but this is a good life skill to have. Especially imagine if we were in a world that had more. It was 50 years ago.

Starting point is 00:33:08 Or now in a lot of countries, you still can't drive automatic. So I don't know if you've heard the same stories I have about how many people have lost their Google accounts. There was a guy I know who's a very savvy tech entrepreneur in Singapore who, because he was so tech savvy, he put all of his kids' photos in the cloud since the day his kid was born. He put everything onto Google Photos. For 10 years, his kid was 10 years old, the day that he started a new company and said, I'm going to do the Google Apps for Business. And it asked him a quick question, would you like to merge this with your existing Gmail account? He said, yes. He merged it. And the next day, his wife was like, honey, where are all the photos of

Starting point is 00:33:44 our kid? He went there in Google Photos. She said, no, they're not. And the next day his wife was like, honey, where are all the photos of our kid? He went there in Google Photos. She said, no, they're not. And he looked up. He's like, oh, my God. You mean they're gone? And he emailed customer service and they said, well, no, you chose to merge your accounts and we warned you that they're gone. He said, well, could you please recover them? They said, no, they're gone. This poor guy has no photos of his kid from age zero to 10 because he trusted the clown. I mean, sorry, cloud. He can't trust those clowns. So, sorry, that was some tech snarky. Escape the clowns and the cloud.

Starting point is 00:34:10 Escape the clown. Tech snark. Okay, so. Oh, you did that? Did you do that on purpose? I did. Oh, that was good. So, yeah, anytime when somebody talks about the cloud, you know, change it to an N.

Starting point is 00:34:23 Clown. Got it. Keep all my contacts in the clown. So everything I'm going to describe here takes just a few hours to set up. This isn't a major, major thing. It's not that hard. Listeners of yours are used to being suggested

Starting point is 00:34:40 to learn how to do something. And let me also preface this for a quick second. This is not a tangent by saying, I do not experience you. Maybe I to do something. And let me also preface this for a quick second. This is not a tangent by saying, I do not experience you. Maybe I'm missing something. Maybe you have spider holes dug in the backyard. I do not experience you to be a hyper paranoid person at all. So I just want to mention that because folks might think,

Starting point is 00:34:58 oh my God, this guy's got like 20 years worth of oatmeal and like, you know, gold bars and guns in the basement. And he's this guy. Maybe, right? I want to sort of set the proper reference point, which is I don't experience you to be a paranoid person. Not at all. Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by Wealthfront. There is a lot happening in the US and global economies right now. A lot. That's an understatement. Are we in a recession? Is it a

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Starting point is 00:36:10 There are already nearly half a million people using Wealthfront to save more, earn more, and build long-term wealth. So why wait? Visit wealthfront.com slash Tim to get started. That's wealthfront.com slash Tim. This was a paid endorsement by Wealthfront. So first, let me just say, the first thing you need is to get your own server, which is as simple as $5 a month. If you go to, there's a company I recommend called vulture.com, but it's spelled V-U-L-T-R.com. I could use some branding help, but yeah, okay. So they have something called Cloud Compute for $5 a month, where basically that's setting up a private slice that's just yours, but on a shared computer.

Starting point is 00:36:52 Okay, so it's like a virtual private server. A virtual private server, exactly. I was trying to not get technical. Yeah, yeah. And a server, for people who don't know, I know this is going to be old news for a lot of folks. What is a server? Sounds super complicated and technical. It's just a computer that's always online. That's it. Publicly accessible, always online.

Starting point is 00:37:10 Doesn't even necessarily need to be public. We'll get to that. Because I think for setting up your server, there are three options. Either the $5 a month, vulture.com, cloud compute. Number two, search the web for a cheap, dedicated server. So now a dedicated server is an actual piece of hardware that is only yours, not shared with anybody else.

Starting point is 00:37:27 So if you want more privacy, just spend a little extra money and get a dedicated server, which means, yeah, this physical hardware, you're the only person that has, they have physical access to it, but you have the only root password and it's going to be an encrypted hard drive. We'll get to that.

Starting point is 00:37:40 The third option is go to any used marketplace and find an old used lenovo thinkpad ideally from the t400 series you can get these for under 200 now and they're great and they run any old operating system and you would just set this up in your closet and keep the master version of your server in your closet and then the other things would be mirrors of that but we'll get to that in a second okay so. So here comes my, here's my quick how to, and I'm going to tell you a few things here that aren't complete instructions, but they're enough for you to search the web. So I'll tell you what to do. And you can search the web for exactly how the first thing you're going to need to do is to use the terminal. So the command line in the Mac, it's built in, you go into

Starting point is 00:38:23 utilities folder. it's called terminal on windows it's called powershell and anybody using linux you know what it is so the operating system i'm going to recommend the one i use is called open bsd and we touched on this on the street the other night the reason i use open bsd bondage sadomasochism so no no no sorry berkeley software distribution quick but i was born in Berkeley, California and kind of like more people named Dennis go into dentistry because there's an affiliation of names

Starting point is 00:38:52 Freakonomics pointed that out I always wonder if my affinity with the BSD operating systems is because I was born in Berkeley I'd be a stance for Berkeley, who knows Anyway, but the reason I got turned on to OpenBSD is because I used to have Linux server as a public server and it was hacked. And the guy at the data center said, oh yeah, that's been

Starting point is 00:39:11 happening a lot lately. He said, you might want to switch to BSD. It's a lot more secure. So OpenBSD is designed from the ground up by super security freaks. And part of why it's so secure is it's so simple. It's a very, very simple operating system that doesn't do everything under the sun. It does this that I'm describing, and it does it really well, and it's secure as hell. And it's got, as I understand it,

Starting point is 00:39:33 a few lines of code. Yes. Right? Which means, let's just say you're a writer. The more you write, the higher the frequency of typos. Yes, well put. And you don't want bugs in your code.

Starting point is 00:39:43 They can be exploited. The less code, the better. So install OpenBSD and follow the instructions to encrypt one of the disk partitions in there as you're installing it. Then you're going to use SSH, which stands for secure shell, to log into it. Then on your home computer, use that terminal to generate a private SSH key. You do SSH dash keygen. The type you want is is ed25519 and then that's going to generate two keys a private key and a public key you upload the public key to your server and then after you do that edit your ssh configuration file to disable password logins so now the only way to log into your server is with your private public key that you just generated, right? Very similar to the crypto public-private thing.

Starting point is 00:40:26 Then you go into your pf.conf settings, you edit your firewall to only allow port 22, which is the port that SSH uses to connect. Once you've done that, voila, now your server is super secure. Nobody can get in except you from your computer with the generated private key. Through SSH is the only way to connect to that server. Can you explain the generated private key? Yeah, it's really just a single command you type on the terminal. If you type ssh-keygen-t ed25519, it will ask you for an optional password,

Starting point is 00:40:58 and it just creates the private key and the public key. Same name, but one has the.pub at the end. And then you just use whatever tool you want to upload the dot pub to your remote server you put it into the correct place and authorized keys file and voila now it will instead of asking you for your password it just uses the private key and the public key matching to let you in got it so it's like marco polo okay yeah we're in as opposed to entering a password every time. Right. And that's why then you want to change the SSH server configuration files to disable passwords. So even if a billion script kitties were trying to hack your server to guess your password, passwords are just disabled.

Starting point is 00:41:39 Okay, this is keep track where you are. Yeah. Do you think this will become, and I'm non-technical folks, you've probably guessed, but this type of Marco Polo, I can't even remember the proper way, the private keys and so on, private-public keys or whatever the term is, will become more and more prevalent as, say,

Starting point is 00:41:56 quantum computing and so on allows the current level of encryption to be decrypted more and more effectively. I'm just wondering about, well, this is going to take us off on a major tangent. I think it's what our phones are already doing behind the scenes with WhatsApp encrypted chats or FaceTime, or even just our phones themselves. When you type in that code, when you first turn on your phone, I think our phones are

Starting point is 00:42:17 already behind the scenes using public private key. Yeah. So that's the way it should be. It's just, it is the best solution so far, I think. Yeah. Side note, if you have a four-digit password on your phone, you can change that to eight-digit. Simple upgrade in settings. Okay.

Starting point is 00:42:32 So next thing, you need a domain name. My recommended place to get a domain name is a wonderfully nerdy non-commercial site called bookmyname.com. B-O-O-K-M-Y-N-A-M-E.com. You don't get 10% affiliate cost, do you? Absolutely not. Wait till you see the site. It's like a wonderful old school nerdy.

Starting point is 00:42:47 GeoCities. There's no affiliate program there. As a backup, I use NetIM.com. Both of these are French companies. And there's a third one in Portland, Oregon that I like called PorkBun.com. PorkBun. Yeah, all three of these are really good reputable places to get a domain name. I recommend them.

Starting point is 00:43:03 No affiliate fees at all. I just like them. I use them. Okay. So now you've got a server and the best thing to start with, like you said, I'm not a guy that's got stockpiles of oatmeal and gold, but once you've got, I don't know why you picked oatmeal, but once you've got your own server, it puts everything else into perspective. So that's really where I'm coming from when I say I don't do things in the cloud. It's because when companies come out and say, we can take care of this for you, it's like you've already got your bread and peanut butter and jam in the kitchen, and somebody says, we can make a sandwich for you in your own home.

Starting point is 00:43:40 You think, I don't need your help. For those people who listen to what you just said, and they're like, I think I just heard a lot of Klingon. in your own home. You think, I don't need your help. For those people who listen to what you just said and they're like, I think I just heard a lot of Klingon. I'm not sure, but I can't parse what any of that means. It sounds overwhelming.

Starting point is 00:43:52 Right. What would you say to them? I care about this so much that I'm going to set up a really dead simple thing that's basically just do this. Copy paste this.

Starting point is 00:44:02 This is going to work. Look at that. So email me. God damn it. Email you. Write a blog post, Derek Simmers. I will. Blog post? What's that? You've only written 5 million blog posts since 1987.

Starting point is 00:44:15 You know what? I registered the domain name Cloudfree with the dot e for Estonia. So Cloudferp e. Cloudfree.com wasn't available? don't know i just thought it was clever okay cloud for e no but someday i'm going to write this up into a a very simple you don't need to understand this yet just do this eventually you'll understand it because that's how i learn where are my photos of derrick service that's all my photos right that's what i really wanted

Starting point is 00:44:42 i want your photos because that's how we all learned it first right it's often like just do this you'll understand it later yeah not just do it and i think that's a fine way to learn if you trust the source right trust me so it's not as hard as it sounds okay it's like someone describing how to hit a baseball you'd be like what the fuck that was like 15 pages of describing and that sounds too hard it It's like, actually, no, you just gotta try it a few times. Yeah, okay, so by the way, you know what's cute? My kid didn't know what baseball is. They played baseball

Starting point is 00:45:11 last week at school, and he said, Dad, what's this thing with the squares and set up in a... And he hit a home run on his first try. Oh, wow. It's all downhill from there. Tell him to stop. Yeah, exactly. Everybody was cheering for me, but I didn't know what I was supposed to do. They told me to run. Okay, so now let's talk about some applications.

Starting point is 00:45:27 Okay, so you have a server set up. Here's what you're going to do with it. First, do your contacts and calendar. So I don't like the fact that my phone automatically gives Google all of the contacts and all of my calendars or Apple or whatever. So you can set up, it's called Radical, R-A-D-I-C-A-L-E. The website is radical.org. It's absolutely free, open source. R-A-D-I-C-A-L-E. Yes. Okay..org. It's absolutely free, open source. It sets up what's known as a card dev and a Cal dev server. On your server, this will be the new server that you sync your contacts and calendars to.

Starting point is 00:46:06 So it's dead simple. Blew my mind. You install Radical on your server. You just basically type one command and it says, okay, it's running. You say, okay. And then you go into your phone and instead of telling Apple

Starting point is 00:46:16 to manage your calendar and contacts, you just set it to your domain name. And suddenly it says, okay, synchronized. And now every new contact you add and every calendar entry is synchronized with your server, not ours. Yeah, and actually, I have gone through this process before.

Starting point is 00:46:31 And I can tell people it's quite simple because things have probably changed. But quite a few years ago, if you wanted your, say, Cal on Mac and Google Cal to sync, huge pain in the ass. Right, you had to use a third. So you would have to use a third party,

Starting point is 00:46:48 and at least I ended up using CalDAV a long time ago. That's since changed. But yeah, so this is not very hard. Deadly. That's why I started with this, yeah. It's like the simplest thing to set up. And the most sensitive in a way, or some of the most sensitive, right?

Starting point is 00:47:02 Calendar and contacts. It's so important to know that my contacts aren't being sent to yeah other people and then you see it backed up yourself because there are some people that get locked out of their gmail account or whatever and then they're just screwed because all their contacts are in there but yeah you have them yourself okay so next thing is file storage where photos books ebooks movies documents everything else they're just files so the first thing you want to do is to export them out of the apps that are like the walled garden apps, like Kindle and Apple's photos app and save it as regular files. EPUB, JPEG, MP3, MP4, just open standards. So you export it out, you save it there. And now you've just got regular files. You don't need iCloud.

Starting point is 00:47:40 You don't need Dropbox. You don't need Google drive. You've got your own server. So every computer has this dead simple little program built into it called rsync. R-S-Y-N-C. Well, Macs have it built in. Windows, I think you might need to install it, or maybe it's there with the new PowerShell. And all it does is synchronize the difference. So if you have 10,000 files and you've changed three of them today, and your remote server has 10,000 files, but not the new three, you type rsync and it'll just send the newest three that you've changed. That's it. So rsync is built in, but you have to manually type rsync in the command and your server name and it'll go. So that's what I do. But if you're a fan of Dropbox, there's a free replacement for Dropbox called Syncthing.

Starting point is 00:48:21 S-Y-N-C-T-H-I-N-G dot net. So it's totally free, open source. I want to give you more scotch, just see what it does to your spelling. There's going to be a lot of spelling. So it's completely free and open source, and it does that more automatic style instead of manual

Starting point is 00:48:40 synchronization. Well, let me pause. So in your particular case, do you think automatic sync, do you think automatic sync? Do you like automatic sync? I like having the delay between my servers. Because if you fuck up. Yes. Right. If I accidentally delete a file, even if it's a week later, we'll get to actually, you know what, I'll talk about this right now. I have my servers cloned. So that's actually the next step I would recommend anyway. Once you've got this and it's working, for extra security, go back and repeat that first step and set up another server

Starting point is 00:49:08 with a different company in a different country and do it again. Do the SSH port thing. Then you can use rsync or sync thing, not just to clone between your computer and your server, but that server and the other server.

Starting point is 00:49:21 I have a great idea. Okay. You ready? Yeah. All right. So this next chapter of Dr. Severs, entrepreneur interacting with customers you like who own personal websites. You could create a service that helps people liberate themselves from the cloud

Starting point is 00:49:38 for those who own personal websites. I like it. Anyway. Just an idea. Because you seem to be philosophically aligned like it. Anyway. Just an idea. Because you seem to be philosophically aligned with this. Yeah. I'm passionate about it.

Starting point is 00:49:51 It upsets me when people are bound to the cloud or just kind of use everything in the company's hand. They're dependent on this. It's about being dependent. It's about the self-reliance. People who are dependent

Starting point is 00:50:02 on others. Like imagine if everybody in their own home was dependent on somebody else to make them on others. Like, imagine if everybody in their own home was, like, dependent on somebody else to make them food. They didn't know how to make their own food. You'd feel bad for them. Like, come on, it's not that hard. Here's a knife, here's some bread, some peanut butter. See, you could do it. You know, like, that's how I feel with these things. You only need three glasses. It's easy. I would also say that it's not just about being dependent, it's about being informed. So do you have complete understanding or near complete understanding of how you are storing sensitive information?

Starting point is 00:50:36 When's the last time anyone listening to this, or even I'll speak for myself, yours truly, read the complete terms and service? When something pops up and it's 27 pages and you're like, yeah, yeah, yeah, okay, click accept. There's a lot of stuff buried in there. There's a reason there are armies of lawyers that work on terms of service and that they're updated constantly. Which is nice to tune into people who care about that stuff deeply. And they can act as a nice natural filter to let you know if somebody's being good or being bad. That's how I found, you know, when I recommended bookmyname.com for domains, it was like some super nerd that recommended that. They're like, oh, these guys are old school

Starting point is 00:51:11 unix. You want to go with these guys? Like, you know, they're not these new salesmen trying to, you know, raise venture capital for their domain selling. These are just old school nerds doing it for the right reason. That's what I like to hear. These are my people. Okay. So I have three servers now set up in New Zealand, US, and Germany, and I like the delay between them. So I have one that I update every night, sometimes multiple times a day. Manually. Yeah, I just type rsync right before I shut down my computer. It backs up my today's work to my remote server. And then about once a week, I back it up to the second server. Then about once a month, I back it up to the third

Starting point is 00:51:44 server. And I really like that delay I back it up to the third server. And I really like that delay because there have been times that I've deleted something and like a whole week later, I went, oh, crap. Let me ask a dumb question, maybe. Why delete anything? Storage is so cheap. Oh, I know. No, I mean more like deleted lines of code.

Starting point is 00:52:00 Like I thought I was done with that. Right. There was a revision that you want to undo. Yeah. Yeah. And sometimes even using Git, but sometimes I'm not. And sometimes it's gone. It's rare, but every now and then.

Starting point is 00:52:09 Okay. So website is a no-brainer. The OpenBSD operating system comes with its own web server. So I highly recommend, no offense, to don't install WordPress. Ooh. We love you, Matt. I adore you, Matt. But I think everybody should learn how to do it

Starting point is 00:52:25 themselves. It's not that hard to do an H1 tag, H2, P tag, ULI, AHREF, image source. You can learn it in an hour. And voila, now you can make your own HTML website. And anybody, because I get this question about once a week by email, people saying, what do you recommend? I want to make my own site. Well, hold on. Not to push back, but just to stress test a little bit. WordPress is open source. Why not use it? You could.

Starting point is 00:52:53 But see, WordPress is, I think last time I counted, 38 billion lines of code. Yeah. And it does way more than what you need. So it's kind of like if you said, I need some scissors, and somebody hands you the contents of an entire hardware store. You're like, no, I really just need to cut this. So I think most people, what they want from a website is, I have some thoughts, I want to put them in writing for the world to read, or I have a couple photos. That's what most people want. But then, I love WordPress, and I used it for years, but it does everything.

Starting point is 00:53:26 And I think it intimidates people to the point of paralysis. Yeah. So that's why I say, well, no, no, no, no, hold on. My top recommendation is don't let people tell you that this is complicated. Because if you look at WordPress or similar services, and by the way, I'm just saying WordPress, I mean, it could be Ghost, it could be any of these things. You get the impression that making a website is hard. Yeah.

Starting point is 00:53:44 But it's not. It's just a plain text file that you change it from.txt to.html and you add in a couple bracket tags. Yeah. And that's it. Yeah. And then you upload it and it works and the world can see it. So I just constantly remind people how simple this can be.

Starting point is 00:53:57 And I say that even if you just do it this way for the first month, please, like, make your own static HTML web page even. I think it was a good exercise. Even if you end up later using something else. Exactly. Right. That's what I was getting to. Yeah. So start by doing it that way.

Starting point is 00:54:12 And then if you need something that another service offers, you'll recognize that you need it because you'll know. I agree with that. I mean, I edited the first 30 to 40 episodes in my podcast, which is a lot of work and I'm not a master at it. And there are far better people who work on it now for these later episodes. But I felt good doing it in the beginning. And I was like, all right, if I'm going to delegate anything,

Starting point is 00:54:39 to the extent that it's feasible, I'd love to learn how to do each thing. Otherwise, how am I going to assess anything? Yeah, exactly. Okay, I'll name one last one and then we're done with this subject. The last thing I'm going to recommend is email. So at very least, get off Gmail and use your own domain name. It's so important to switch your email to your own domain name. You can do that with G Suite though. I know, but we're talking about the liberation, the independence. It's knowing that you aren't dependent on these guys. So I think it's crucial to extract yourself from the we'll take care of it for you thing. So the three things I'm going to recommend, the three different options in order.

Starting point is 00:55:18 The simplest, cutest little one I've found is mailbox.org is in Germany. And for $1 a month, they do nothing but host your email. And I think maybe your calendars, but you know, we've already talked about that. But mailbox.org, you point your domain name at them. They do your mail. They're cute. They're great. Privacy focused. If you want the luxury full premium suite of like the best email client on earth, you go to fastmail.com. Fastmail.com is amazing. It's $5 a month. But again, it's they're taking care of it for you. So you know, the third option is coming. You can host your email yourself on your own server. It's dead easy to receive

Starting point is 00:55:57 email. It's a little harder to send email, you'd have to set up a few config files. But it's not that hard. I do it myself. It's a bit advanced, but it's possible. And I assume that that would come maybe as, you know, step eight after you've done other things. Right. That's like if you're starting on the bunny slopes, which were the first stages, this is like, okay,

Starting point is 00:56:15 now you're getting on some moguls. Yeah. Don't try this day one. Get familiar with the gear first. So I would be curious to know how you would reply to people who are listening and they're like, mailbox.org in Germany? Fast mail? I've never fucking heard of these things. Great. than I do in these companies, which I know nothing about. Ultimately, you can have a certain degree of liberation,

Starting point is 00:56:46 but if your infrastructure fails, or these people put up a closed-for-business sign, and suddenly the hardware upon which things are being stored is game over, I guess I'm wondering how you would address people with those types of concerns. Everything I've recommended here was recommended with that in mind. You should expect that you will outlive most businesses. Yeah. I think that, to me, is the biggest misconception

Starting point is 00:57:13 that people have about Facebook or Apple or Google, that it's likely you might outlive Google and Facebook. Yeah. Those of us who were around in the first dot-com boom. Yeah, if history repeats, it's certainly well within the realm of possibility. Yeah, it was unthinkable in whatever, 1999, that MySpace wouldn't be around. Or maybe, what was that, 2003? So how is mailbox.org better in that sense?

Starting point is 00:57:38 Because everything is done with your own domain name. So if mailbox.org ever sends, actually, if they just disappeared one day, you'd go, you just log into your domain name router and just route it to another service. Because everything's being sent to, you know, Tim at Tim.com. So you have your own domain name, you can just route it to a different mail server. Same thing with the servers I'm talking about. If one of these services in Germany or New Jersey suddenly went under, no big deal. You've got your clone, your remote clone, your remote server is a clone of your home thing.

Starting point is 00:58:06 So all of this is expecting everybody to fail. So the conclusion is, I think this is a great use of your time. It's liberating. It's empowering. And then when somebody tries to sell you a service, you'll know that you can do it yourself if you want to, and you might still choose

Starting point is 00:58:22 to have them do it. Question for you. So if somebody's listening and they say, there's no fucking way I'm going to do all that. However, I'd be interested in dipping my toe in the water and maybe doing the first thing just to learn some new technology, gain some confidence. I'm not going to do the whole kit and caboodle because it just sounds overwhelming, but like I want to do sort of a science project with some experimentation experimentation what might you recommend to them i'd say the first baby step is to get your own domain name definitely and then move your email off of gmail and just go to some third party provider of okay so you start with email i think

Starting point is 00:59:00 so it's the simplest it's the only one in there that's not truly setting up your own server. Although I mean, that would, you know, obviously that's the next step is just do that first thing and just have like a couple hours of something that feels uncomfortable and new to you. But voila, you have a server that's running anywhere in the world. And once you have a server, everything else is easier. But yeah, the baby steps is to just get your own domain name and switch your email to that and try to just move everything off of Gmail or just let your old Gmail be your junk account. Okay, question for you personally. If you had to choose between having your email off of the cloud or calendar and contacts, but you can only choose one.

Starting point is 00:59:44 So calendar and contacts come together. Email is another. Which would you choose? I don't know why there's a sense of happiness in having my calendars and contacts be on my own server. Yeah, I lean that way too, and I don't know if I could verbalize why that's the case.

Starting point is 01:00:00 Mail sending has become unfortunately difficult because a lot of things get marked as spam unless you do a bunch of more complicated things. That's right. I didn't think about that. I could see that being a huge problem. So the way I actually have my mail server set up right now, and I don't mean this to... Pretend to be Gmail.

Starting point is 01:00:15 Well, God, Nick, can you imagine? What could go wrong? All incoming email comes directly into my server. But for sending, I actually use a service called Mailgun that just handles the sending. So they take care of all the deliverability. Yeah. So it's not an ESP, but it's helping,

Starting point is 01:00:34 or maybe it is an ESP, like an email service provider. Oh, it is. Yeah. I guess there are going only. Yeah. I think,

Starting point is 01:00:40 I wonder, I think SendGrid does handle some of this as well. Yeah. They're one of the same. So you're really just using their SMPTE servers just to send the outgoing mail, but receiving it privately. So that's my balance right now.

Starting point is 01:00:50 SendGrid, those guys have done such a good job, at least last I checked. And I met them when they were just starting. I met them at Techstars a million years ago. And this is an example of where being non-technical hurt me because I just didn't know what I was looking at. The guys were super great, clearly very smart, but I was like, I don't understand this.

Starting point is 01:01:12 Wait, can we tell people the Shopify? Oh, man. I mean, my most expensive mistake ever? No, no, no. My little thing with Toby. Oh, yeah, yeah, yeah. It's cute. I'll leave.

Starting point is 01:01:26 I'll let that one float by. Sorry. No, that's okay. Stir up a... Yeah, selling Shopify earlier was my most expensive mistake ever as their first advisor and they had like 10 employees. So audience, there was this cute moment. So we're going to get to cute moment.

Starting point is 01:01:38 I just want to say that also, God, do I love the Shopify guys. I just thought they're so great. Toby, Harley, the whole gang, just great humans. It's really, it makes me so happy when the good guys and gals do well. It just makes me so happy. So, cute story. Sometimes people ask if I can introduce them to you. Yeah.

Starting point is 01:02:00 I'm like, no. I respect your time. Yeah, I appreciate that. By the way way i love your your email address oh yeah yeah yeah which basically says fuck off yeah it's essentially fuck off at timferris.com it's not yeah it's not that aggressive but it makes it clear like think twice before sharing don't you dare give this to anyone yeah at timferris.com that is his personal email.

Starting point is 01:02:25 Yeah, yeah. A little wordy, but you know. It's worth it. Give him a hurdle. So, oh, Toby. So I love the Ruby programming language. And so before there was Ruby on Rails, I learned Ruby in a cabin in Sweden

Starting point is 01:02:40 that I was offline for two weeks. So I brought a programming book with me. I was like, well, I'm going to be offline for two weeks. I might as well learn something new. So there was this really unknown little programming language called Ruby. I was like, that sounds fun. So I grabbed this Ruby book, installed Ruby on my laptop, and went off to this cabin in Sweden in the winter for two weeks.

Starting point is 01:02:58 I was offline and I learned Ruby for two weeks. I came back going, that was so much fun. I wish I could use this to make websites. And there was news that there was this guy named David in Denmark who was doing something with websites and Ruby. So I emailed him saying, hey, somebody said you're making like a web framework in Ruby. And he emailed back saying, not ready yet. That's all he said. So for those that don't know, that's DHH, David Hanmeyer Hansen. Yeah. And so then Rails came out about eight months later.

Starting point is 01:03:29 And at first look, I was just like, huh, this is a little confusing. I don't really get it. And so I posted to like the Ruby mailing list. Can anybody tell me? I'd be happy to pay somebody for an hour of their time to show me how this works. So some guy named Toby said, I'll show you Rails for $100. I'll spend an hour with you. So I paid Toby $100 to show me Rails for an hour. And he showed me over the phone. We never met face to face. It was all just over the phone. I was living in LA. And Toby was great. He showed me how Rails

Starting point is 01:03:55 works and like got me really into it. I was like, all right, I'm in. And so my old company, CD Baby, we started converting everything over to Rails. I was like, this is great. So a couple years later, I get this email from Toby saying, hey, not sure you remember me, the guy that taught you Rails? He said, could you introduce me to Tim Ferriss? Because I've got this little e-commerce thing I'm doing. I was like, e-commerce thing? No. I was like, sorry, dude, I don't do that. No, no, no. So I didn't introduce you guys. So I was thrilled later to find out that Toby's little e-commerce thing is Shopify. Or became Shopify. Became Shopify.

Starting point is 01:04:32 Became the Shopify. And then I was thrilled to find out like another year or two later that you were. We met at RailsConf of all places. Wow. I was a speaker at RailsConf, which I felt I was supremely underqualified. They love doing that. But I met him in the green room at RailsConf. Yeah.

Starting point is 01:04:51 That's how you met. I was going to ask you. Yeah, that's how we met. Wild. So wild. Toby and I have emailed since then about like joking about, yeah, sorry I didn't introduce you yet. Yeah.

Starting point is 01:04:59 Toby's. It all worked out. Toby's a spectacular human. Big, big fan. It's kind of funny that somebody listening to this thinks that we might be talking about tech and programming the whole time. But no, that was it. We're done.

Starting point is 01:05:11 We're not going to talk about Unix command line terminal stuff anymore. Well, we'll zig and zag. So let's zig a little bit. You know, there's so many options here for where to go next. I think one I'd actually like to talk about is the unoptimized life. If you'd be open to going there next, what do you think? Yeah. All right, let's do it. London. London. 2019. This is going to be good. On the train from Oxford to London. And it was one of those days that looked like it might rain, it might not.

Starting point is 01:05:47 So we made a plan on the train. I said, okay, if it's raining, we're going to go to the museum. And if it's not raining, we're going to the zoo. And he said, okay. So we got to a Marlborough station in central London. We walked out and he said, you know, dad, I don't want to go to the zoo or the museum. I said, what do you want to do? He said, let's just walk around.

Starting point is 01:06:06 Sure. Yeah. Okay. We just walked around. So at every intersection, he said, let's go this way. So, okay. And so he just led the way through London that day. We walked around for eight hours.

Starting point is 01:06:16 So at one point he was jumping around park benches and met these kids from Croatia where they got into a little tickling match. At another time in like a little alleyway, he saw this huge cardboard box that was like almost as big as he is. And he got into this cardboard box and wore it like a turtle shell. So he walked around London in a cardboard box for like an hour and everybody would do double takes looking at him and he felt so cool in the cardboard box. And then at some point we found ourselves right in front of the West End musical Wicked. And the show was about to begin in 10 minutes. And I said, do you have any tickets? What are the best tickets you have? They had eight throw center tickets. They had two left. So we're like, yeah, let's do it. Let's go see Wicked. So he left his cardboard

Starting point is 01:06:57 box there. We went in and saw Wicked. And at one point he whispered to me, he said, dad, I like the girl next to me. And I said, okay. And later I look over and he's holding her hand. He held her hand. They held hands. And so show was over. We go home and I tuck him into bed that night. And I said, did you have a good day? And he said, I had a great day. And I said, all right, so what was your favorite thing today? And he thinks for a bit. and then he said, the cardboard box. And I was just like, I marveled at that. I was just thinking later, like, if I would have planned and said,

Starting point is 01:07:34 no, we're going to the museum, come on, it's an important museum for you to know, then he wouldn't have had this unoptimized experience and stumbled into the cardboard box. And so, of course, you know, I think about life and I think about like that day as a metaphor for how we tend to make plans because plans seem to be the tool we use to make the most of our time. But that doesn't always make sense, does it? Because like, as you go through life, you keep getting new information moment to moment that helps you make the best decision for that moment, not what you thought would be the best decision earlier when you made the plan,

Starting point is 01:08:15 which was a prediction. I think about, for example, this stupid house I'm in right now. So this is my stupid house, everybody. I don't like this house but here i would never guess based on your assortment of matching plateware and how much energy i've clearly put into this house and making it perfect with all of its decor um there's nothing on the walls and no furniture yeah so um except for some mice legitimately yeah I have three pet mice we were going to bring them out

Starting point is 01:08:48 it would be distracting I thought about getting rid of this house and getting a house that was more suited for me and I actually put an offer on a place and it was a really nice place it was at the end of Clyde Key Wharf which is out there in the water and oh man it was nice

Starting point is 01:09:03 my offer was accepted and it was the night before I was going to put down the deposit. It was going to be mine. I fell asleep that night thinking, at first thought I was thinking, I'm going to be so happy tomorrow. And then I thought, wait, I'm already happy. What am I going to be more happy tomorrow? No, I'm already happy. It's like, well, then why am I doing this? Why am I spending a bunch of money if I'm already happy? So I yanked it. So I didn't buy it. And here I am in this stupid house because it has no obstacles. Like it's warm, it's quiet. It's not suited to me perfectly, but that's okay. Like it doesn't get in my way. And then from there, I think how many other things in our life are we okay to just not optimize? Depends where you draw the line, right?

Starting point is 01:09:49 Your romantic relationship, your job, your family. But nobody has the perfect family of their wishes. Our location, where you live, our diet. You have to kind of decide what's worth optimizing. That we don't need to optimize everything. It's okay to have some things be good enough. And so I'm so glad you brought up The Paradox of Choice by Barry Schwartz.

Starting point is 01:10:11 I really fucking internalized that book. It's a great book. The ending of that, where he says like, okay, I've been describing the problem. So what's a recommendation? And he says, satisficing. There's maximizing and there's satisficing. I had no idea you were going to bring this up. This is great. Yeah.

Starting point is 01:10:27 Yeah. Maximizers have been found to feel worse about the decisions they make. They look into every possible option. They try to make the best possible choice, but studies show that they feel worse about the choice they make.

Starting point is 01:10:44 Whereas satisficers may not make the absolute best possible choice, but they feel much better about the choices they make. Yeah, I think a lot of who I am is because of satisficing. And if I seem like I make weird decisions in life, for example, like not even continuing to pursue making money, it's because I'm satisficing. Like I really took that lesson to heart and have shaped my life around it. So just for definition terms, right?

Starting point is 01:11:09 Because people might think optimizing is trying to eke out the every last iota of improvement, right? But I think what we're really talking about is- Wait, sorry to interrupt. You know, like if you were to hear Paul McCartney go, hey Jude, you'd be like, whoa, just to hear him sing two notes. Yeah. To hearney go, Hey Jude, you'd be like, Whoa, just to hear him sing two notes to hear you go optimizing. That's classic. You know, if that is my legacy, so be it. Optimizing. I think what we're talking about is where to focus your finite energy on

Starting point is 01:11:47 improving versus leaving things as they are right in a sense right because i think optimizing when i think of optimizing optimizing is leading to optimal what does that even mean maybe it's open-ended so it just continues forever but it's helpful word. I'm just curious how you currently think about where to focus your energy on improving externally versus leaving things be. And this is a conversation that's near and dear to me. One of my most effective friends basically has said, I'm paraphrasing, but he's like, yeah, I optimize for like one or two things and everything else is good enough. Like I just have to get it to good enough. That's it. And he's incredibly effective in life. And he's also a very happy guy in general. Hard to know how much of that is out of the box versus

Starting point is 01:12:41 due to the decisions and the way he views the world, but seems to contribute. So how do you think about then where you might maximize versus where you satisfy? Because I know it's not good enough across the board. I find that hard to believe. What do I maximize? I'm not sure. Or maybe maximize is too polarizing a word. No, you know what I think it is? Yeah. If it's really fun.

Starting point is 01:13:08 Okay. If you think it's just actually really fun to like, maybe some people set up their, well, let's just say they get into bread making. And they're just like, I want to set up like the best bread making. They're just having fun with it. Then great. They can maximize, you know,

Starting point is 01:13:22 people who get really into high fidelity audio. Yeah. And they nerd out and they know it's stupid usually yeah and they're just like i don't care i want this thing with the gold plated cable connector right and i think if you have fun optimizing then it's worth it if maximizing that is if the process is fun to you i think that should be the parameter but i think that saying enough good enough is a superpower yeah i really do i really agree with that you know what is such a good lesson to learn is that nobody cares what you're not good at okay say more like publicly people only just known for a few things that you're good at yeah all those things that you're

Starting point is 01:14:03 not good at nobody cares that you're not good at them. So just let it go. Now, for the broader public, I think that's really useful. But you may have, say, a significant other who cares about some of the things that you're not particularly good at. There is that. I mean, not that I'm recently single. I'm thinking about this all the time. There is that. Not that I'm recently single and thinking about this all the time or anything. We have spent many hours talking about sex while walking in the forests of New Zealand.

Starting point is 01:14:36 Sex and relationships. Well, even before this podcast, Derek is setting up all these cameras and all this stuff. And then he's like, I just need to take a quick shower. And I was like, wait a second. Are we about to have sex? Derek, what's happening? I haven't had a shower since yesterday. It's feeling greasy.

Starting point is 01:14:53 It's distracting. But no, it's funny. I wasn't sure if you were going to say, so as you were saying yesterday in the forest about sex. Oh, no, no, no, no. We'll leave that aside for scotch outside of recording. The unoptimized life. What effect has that had on you paying more attention to that? Leaving good enough alone. Because this is something I would like to do more of. And I've

Starting point is 01:15:20 tried to focus, with some success, on making fast, especially reversible or trivial decisions. If it can be undone easily, this is also with money. Attention and money. I'm going to default to speed with a lot of things. If it's not that important or if it's pretty easy to reverse. I think that's been helpful. Off the top of my head, I think how important it is to be done with something so that you can move on.

Starting point is 01:15:54 Like I don't want... Open loops. Yeah. Unresolved decisions, sitting unresolved, sitting undecided for a long time. Yep. I feel the weight of those. Unfinished projects, because I'm trying to make it perfect. Yep.

Starting point is 01:16:10 I feel the weight of those. I've learned the importance of just getting things done and finishing. And to do that, you usually have to say good enough, you know, at some point. I love the fact that we say we, somebody releases an album, you release a book, because there's a wonderful double meaning in that word, right? Like, all right. I've never even thought about that. Released. Yeah, I like that. So I think about that with anything I post on my site, any of my books. It's like, all right, it's released. It's good enough.

Starting point is 01:16:36 All right, I'm going to combine this, maybe another Sivers-ism. It's not really a Sivers-ism, but in terms of how Professor Sivers operates in the world, useful, not true. We've been talking a bit about this. I wanted to save a lot of it for this conversation with the mics. Where should we start with this? All right. So, again, I'm addressing the audience for a second. So, you know, I figure I'm coming on the podcast. This isn't just one of our random conversations. This is for the audience for a second. So, you know, I figure I'm coming on the podcast. This isn't just one of our random conversations. This is for the audience. There's a reason we're hitting record. It's for them. We can talk freely without hitting record. So I had to think, what's the most useful thing I could share with your audience that I've learned like in the last seven years since we last

Starting point is 01:17:23 spoke? The thing that's made the biggest difference in my life, a superpower, a big huge change. So to me, it's been, in short, skepticism. So if you wonder why I'm so happy, why I'm thriving, why I seem to be doing well, to me, it's a lot of my happiness comes from this worldview that is radical doubt. It's skepticism. And so I'm going to give this the shorthand of calling it useful, not true. But the visual for it is that moment at the end of the Matrix movie when Neo realizes, like, those aren't bullets. This is just code. Remember all the bullets coming his way? He's like, oh, wait, right.

Starting point is 01:18:02 Like, none of these rules apply to me. That's deep skepticism. It's empowering. It's liberating. So what I'm going to do for a few minutes, including a little stories, is to play Morpheus to help emancipate the listeners. So yes, I call this useful, not true.

Starting point is 01:18:20 Preach. Yeah, there we go. Number one. So, okay, I'm going to tell you the four bits first, and we'll use that to kind of make sure that we come back to this. So, number one, almost nothing is objectively true. Number two, beliefs are placebos. So, you've got to believe whatever works for you now. Number three, rules and norms are arbitrary games that can be changed. I'm preaching with converted, that one. And number four, refuse ideology. You need to

Starting point is 01:18:45 accept ideas individually. There's the structure. So number one, so almost nothing is objectively true. So here's what's true. My hand is on the table. But what's not true is it's good to do everything in moderation. Here's what's not true. Family is everything. Here's what's not true. My mother abandoned me. Here's what's not true. AI is the future. So all of these things, people say them as if they're true. Or even when people make an excuse like, you know, I would be more successful if it weren't for my family, you know, or my location or whatever.

Starting point is 01:19:19 People say these things as if they're an indisputably true fact but to me the only thing that's true are the things that both a cat and an alien or let's say a cat and an octopus would agree on you've come up with so many children's books ideas in this conversation the cat the alien and the octopus because it makes you realize that everything else is just mental interpretation right like there we go this is on the table this is true but everything else including watch this one am i flipping you off right now like am i angry at you right now no just because he's giving me the middle finger yeah sorry this is i'm holding up my middle finger with the back of my palm towards tim even if people say things like, I hate you,

Starting point is 01:20:07 does it mean that they hate you? No, it just, they said three words. That's all that actually happened. Their mouth said these words. You can't, everything else is an interpretation or a projection. So we have to consider why people are saying these things. If you start to think why they said something, it helps to dispel it. You can say, oh, you know what, they're probably just believing whatever supports the emotions that they want to feel right now. So if somebody has a belief that family is everything, maybe it's because that was something they told their kids because they want their kids to take care of them when they're older.

Starting point is 01:20:42 So they want their kids to believe that family is everything. But they have a self-serving reason to believe that. Yeah, possibly subconscious, right? Right, right. Oh, so I'm so glad you said this. Have you heard about the split brain stories that people... Yes. Okay.

Starting point is 01:20:55 Why did you get up to have a glass of water? That type of stuff. Can I tell it? Yeah, please. Yeah. So this is so important to understand that... These are crazy. These are so bananas.

Starting point is 01:21:07 Actually, we'll start with the other one, since you know that one. Well, no, no, but the audience doesn't. No, no, no, but we'll do both. But during brain surgery, the patient needs to stay awake. And so there was a woman... And some, yeah. Or I guess they could, yeah. I don't know the details of this.

Starting point is 01:21:21 It was on the Econ Talk podcast. That during brain surgery, they were poking around in there and suddenly the woman started laughing. The patient started laughing and they asked, why are you laughing? And she said, oh, well, it's just, it's really funny the way that that curtain is hanging. And she really thought that the reason she was laughing is because that's the way the curtain was hanging. But it was actually because they were poking a little runner there. And so the split brain patients are some people whose left and right hemispheres of their brain are not connected. So they've done tests on these people to say into their right ear, please get up and open the window. And they'll get up and open the window. And then they'll ask their left ear, or maybe it's their eye, why did you open the window? And they'll say, oh, it was just a, it was a little cold in here. I hope you don't mind. And they really sincerely to the core thought that's the reason they opened the window. There are a couple more examples of this, you know, a message shown to one eye and they did

Starting point is 01:22:16 something. Then they asked the other eye, why did you do that? And every time that people make up a reason, they don't know they're making it up. They give a reason why they did that. And they feel completely confident that that is the reason why they did it. So to me, this is the most beautiful example, like we actually don't know. So talk about deep skepticism, radical doubt. You shouldn't even believe anything you tell yourself,

Starting point is 01:22:41 even in your private diary, when you're saying, I'm not happy in this location, or I can't do this because of that, or I'm mad at so-and-so. You need to ask yourself, okay, that might not be true. Just because I'm saying it, it might not be true. So, number two, beliefs are placebos. So, two people in the same boat, one can say, this sucks, and another one can can say this is great. But neither one is true. No beliefs are true. In fact, you know, the little story of Richard Branson, before there was Virgin Airlines, you've heard the tale that he was at an airport and a flight to somewhere was cancelled.

Starting point is 01:23:17 Right, it was delayed. Yeah. And everybody was grumbling, ah, this sucks. And so he kind of went to the 20 people that were angry and said, hey, if I charter a plane, will you guys split the cost? And I said, yeah. So everybody else was angry. He looked at the same situation and said, this is great. That was kind of the launch of Virgin Airlines.

Starting point is 01:23:34 No, not launch. You know what I mean? The Genesis story. Genesis. Nice word. So no beliefs are true. When we say, I believe, it's an indicator that what we're about to say next is not true. Or not evidence-based. Right?

Starting point is 01:23:50 Not true. Sorry, I'm just having fun. Have fun. Because, yeah, not evidence-based. Because we don't say, I believe in potatoes. Speak for yourself. Because there's a potato. We don't need to say it because there it is. It exists. So I think that whenever we say, I believe such and such,

Starting point is 01:24:13 it indicates that whatever we say next is not true. It's kind of like when science is at the end of a field's name. Generally, it's not science. Not always, but very often that's not the case. I can think of a few exceptions, neuroscience, computer science, but very often when science gets appended to something, it's like, ooh, thou doth protest too much. I like that. So, since no beliefs are true,

Starting point is 01:24:37 I think this is liberating to realize that you can just choose whatever belief works for you now that helps you be who you want to be. This is about personal empowerment. It's a little bit hacking yourself. If a certain belief will help you be who you want to be right now, you don't need to keep believing it tomorrow. You could believe it for three minutes or three days or the rest of your life. You're going to find what you look for. So if you choose to believe something, you'll find evidence to support your belief of anything. So the number three is that rules and norms are arbitrary games. So this is the one where I can't help but think of, you know, your introduction to the world in 4-Hour Workweek, giving so many wonderful examples of how you don't have to accept the world's norms.

Starting point is 01:25:22 Yep, for sure. But it's funny how many times the rules of the world are stated as if they're absolutely true. Like, all applicants must submit their application through the usual channels and wait to hear from us. Or to be an expert in your field, you should have an advanced degree from a university. But someone made up these rules, and most people follow those rules, but they're not true. They're just not absolutely true. So I think that realizing they're not true gives you an incredible advantage because you realize you can make up the rules.

Starting point is 01:25:54 So this is that matrix moment where the bullets are flying out, but it goes, wait a minute, this is just code. Yeah. Somebody made this up, but I don't need to run this program. But if you do that, people are going to be upset at you. So somebody's going to get mad at you, and you have to know that even when they say you're a bad person for doing this, you have to know that that's not true either. And I have a cute story about that.

Starting point is 01:26:20 This, I think, begs a number of questions living in a broader society about morally acceptable or reprehensible behavior. But that's, when I talk about being who you want to be, we can't really address people who want to be psychopaths or who want to be damaging. Because then anytime you taught anybody how to do anything, how to fly a plane, hey, don't fly it into the World Trade Centers, okay? How to drive a car, hey, don't drive it into a crowd of people, okay? You have to just understand that we're talking about a tool, not your psychosis that might lead you to be a bad person. All right, I'm going to table that for a minute. So I have a funny little story that felt almost too risque to tell. I love too risque. Let's do it.

Starting point is 01:27:05 I don't record these in front of a crowd. I can always edit. Oslo, Norway. My band was on tour, and we were there for three nights. And for the first two nights, there was this girl in the audience that was kind of making eyes at me on stage. And so the second night, I went to go talk to her, and we hit it off.

Starting point is 01:27:24 And we hung out all night long, and it was wonderful, but we didn't have sex. That's funny. I was like, can I say this on the air? We did not consummate our attraction. All right, I'm just going to say it. But we kind of regretted it. So then it was the third day and it was the day that I was leaving. And there's this big kind of central park in the middle of central Oslo.

Starting point is 01:27:46 And we're in the park and, you know, housekeeping came at 10 a.m. Like, time to check out, time to go. And she was asking them in Norwegian, like, please, one more hour. And they said, no, get out. She's like, oh. So we go out to this park and she's like, oh, God, I wish I could be with you. I wish. She's like, God, I just so want to be with you.

Starting point is 01:28:03 And I was like, damn, me you and i was like damn me too i was like i wish we could and then i looked around and this park is surrounded like you know sheraton hilton marriott and it was 11 o'clock and my ferry was leaving at four o'clock oh and there's one detail she was just in the process of breaking up with her fiance. A small detail. So this matters because I said, hey, what do you think about getting a hotel for a few hours? She was like, well, we could. I was like, yeah, it feels kind of naughty, doesn't it?

Starting point is 01:28:40 Like, yeah, but let's do it. Yeah, okay, you don't mind? She's like, but I can't be seen with you. She said, just on the chance that a friend of mine walks by, I can't be seen going into a hotel with some strange man. I said, okay, so here's what we'll do. I'll go into the hotel. I'll get a room and then I'll text you the room number and you come up a few minutes later. She said, okay, good. So I went into the hotel and whatever hotel it was, I'll just say Sheraton. And it was like, welcome to the Sheraton hotel. You know? And I said, Hey, I'm here for one night. I'd like a room and great. No problem. Okay. said, hey, I'm here for one night. I'd like a room.

Starting point is 01:29:05 And great, no problem. Okay, tomorrow breakfast will be served over here and such and such. And here's your room. And okay, he gives me my key. So I go up to the room and I text her the room number. And she comes up five minutes later. So then we have fun for a few hours. And it's great.

Starting point is 01:29:20 But now it's 2.30 and it's time for me to go get my ferry. So this time we reverse it. I go down alone first. And I go to the But now it's 2.30 and it's time for me to go get my ferry. So this time we reverse it. I go down alone first. And I go to the guy at the front desk. And I said, hey, I've decided to catch the four o'clock ferry. He's like, oh, is everything okay? Was there any problem? I said, no, no problem at all.

Starting point is 01:29:37 Everything's great. Just decided to catch an earlier ferry. So paying in full. Here it is. So he's charging my card. It's already done. He's doing the thing but then he sees her walk by and he goes wait a minute i don't like this one bit so he remembers

Starting point is 01:29:54 that he saw her come in five minutes after me now she's leaving five minutes after me and he goes this is not some two-bed establishment this is not this is a various reputable hotel. I do not like this. No, you must not do. And I don't like this one bit. He was getting really angry. Yeah. And I was so happy because not for the obvious,

Starting point is 01:30:15 but like it was so liberating realizing that I've done nothing wrong. Nobody was hurt. This is fully like consensual. They were paid for their room. And even though he's angry, he can't get me in trouble. I haven't broken the law. And I think that we so often, as kids, we spend so much of our life, the first half of our life, kind of deferring to authority and thinking that authority has power over us. And at a certain point, you realize that you're free, you're liberated from that. But as long as you don't break the law, even if people tell you you're a bad person, that it's not true. They're just saying that because of their rules or whatever. So this to

Starting point is 01:31:00 me was a major turn point in my life, realizing that I was liberated from authority and from judgment. So a couple of things. So the first is, I read a piece recently, I think the author's name is Ava, A-V-A, I don't know her full name, Book Bear on Substack, and the headline, the title of the piece, something like, On Not Disappointing Myself. And it's a discussion of disappointing others, how disappointing others but not disappointing yourself is important. I mean, that's the kind of upshot of it. Very well written. Introduced to me by a friend named Mike. Thank you, Mike. So I'd recommend people take a look at that because I think it relates. Since you made mention of the fiance though, I want to stand in for some of the audience who will say, well, wait a second. You said you didn't

Starting point is 01:31:53 do anything wrong, but we live in a society. We do follow rules. Otherwise we are with the animals. So what is good? What is bad is based on societal norms. I'm sure there are people listening who are like, well, wait a second. You had fun for a couple hours with someone who was still engaged. How would you respond to people who find that morally repugnant? They had broken up, but were still living together because she just hadn't left out yet. Okay. All right.

Starting point is 01:32:17 Okay. Fair enough. I wouldn't sleep with somebody's wife. Okay. Okay. Or fiance either. Okay. Got it.

Starting point is 01:32:21 But no, I know what you mean. But in those moments, you have to ask yourself, do I agree with this rule? Especially if you travel the world, what's polite in Japan can be rude in New Zealand and vice versa. These different ideas of what is the right and wrong thing to do are completely arbitrary, and they change with geography. And so you get to kind of pick or choose, and you can choose to fit into the local norms, or sometimes you choose not to because you disagree with them. Because it's the same with individuals and people. You're liberated from others' norms. You can choose your own. So there's a lot of this that I agree with. I also wonder how we avoid, maybe we don't, but sinking into a moral relativism

Starting point is 01:33:06 where everything is okay on some level because nothing is objectively good or bad, therefore general mutilation of 12-year-old girls or whatever it is is totally fine in that culture because the culture is different. Therefore, I'm not going to object to anything like that because

Starting point is 01:33:22 I'm not the arbiter of universal truth. Therefore, everything is okay in different cultures, different places, different households, because everything is relative. How do you think about that? I defer to Sam Harris. Okay.

Starting point is 01:33:40 Did he ever talk about the moral landscape on your show? I don't think we've discussed it explicitly. So why don't you, if you wouldn't mind elaborating. Probably the best elaboration is to tell people to go search for Sam Harris moral landscape. The best TED talk I've ever seen. That is the one. Sam Harris, the moral landscape, so beautifully summarizes this idea of judging something morally objectively based on individual well-being and so utilitarianism like greatest good for the greatest number of people

Starting point is 01:34:12 type stuff yeah uh he says it better than yeah i don't want to speak i don't want to speak for say yeah go find that talk this is a there's i think a tension sometimes in my mind between living a self-authored unorthodox life that does not conform to convention for the sake of conforming to convention while also trying to have some type of consistent moral compass. And that is why sometimes I'm actually very envious of people who are deeply religious. It's like, here are the rules, right? I mean, you want to talk about paradox of choice, like how much decision fatigue does that remove?

Starting point is 01:34:56 I'm actually very envious of that sometimes. So how do you think about, and I'm not saying you should think about it, I'm just curious, when, let's just say, outside of breaking the law, you can do anything, right? There is a, it's just like having 1,500 different types of toothpaste at the supermarket and having to choose one in a sense, right? There is a possible decision fatigue there.

Starting point is 01:35:14 Do you use, for yourself, you can define it yourself, but like good or bad or some type of moral framework for helping to narrow the choices that you make available to yourself. In secular societies, I wonder about this a lot. Yeah. I recently read a book I can recommend for anybody called What Everyone Should Know About Islam. And it was really good. And it finally understood about the different Sharia laws. And it's really congruent. I think more than anything, if I had to pick one word to give, it's amazing how congruent it is and what peace that can bring in a society where even the government laws are aligned with the religious laws, which are aligned, like everybody here agrees in this code.

Starting point is 01:35:58 It's not a gray area. But you asked me the other day about, I said that I'm very influenced by the greater good, doing things that even if it doesn't serve me personally or privately, if it seems like it's the right thing to do, I'll do what seems to be the right thing. Yeah. Yeah. And this is just for people who, this came up very organically in our conversation. I don't remember how, do you? Yes, I do remember. Because I think I was talking about how I do not identify as a philanthropist, even though I do a lot of nonprofit work, because I actually have a pretty Hobbesian view

Starting point is 01:36:38 of human nature in general, and think we've probably, we're certainly on a planetary level, cause more problems than we've solved. And therefore I don't fill, like philosophy, right? Like hydrophilic,

Starting point is 01:36:52 like philic is to love, fill, I mean, the etymology of that. And then the philanthropy is like the Anthropocene or anthropology. It's human. So like to love humans basically is philanthropy. And I don't feel like I align with that.

Starting point is 01:37:09 I'm actually a misanthrope a lot of the time. So I said, no, I don't think about that. And therefore I make decisions about A, B or C in the following way, when it relates to some of the nonprofit work and scientific research that gets funded through the SciSci Foundation,

Starting point is 01:37:24 my foundation. And that, I think, is what prompted you to say, I'm not sure if I think of myself as an altruist, but I seem to make decisions for the greater good, which I've observed in you. I think that is the, rewinding the tape, I think that is sort of the stream of conversation that led to that coming up. I was asking about how you consider constraining your choices with maybe right and feels wrong. Or sometimes you actually let your head rule that decision. Yeah. To say, you know what? I know that personally I might want such and such, but I know that ultimately that's, it's not that important. Or maybe the fact that I'm happy anyway affects a lot of my decisions. It's like, I don't need to have some million dollar thing to make me

Starting point is 01:38:26 happy. I'm already happy. Like I've hit the maximum. There is no such thing as happier. I'm already there. So therefore this million dollars should just go to people who can use it because that's for the greater good. Like that's how my brain honestly works. But this idea of isms, ideologies and subscribing. Yeah. You tapped into tapped into that thing that we, what did you call it? The decision fatigue. It really helps decision fatigue to say, I'm all in on this. But I think that people do it to a fault where they read a self-help book and go, oh yeah, this is it. This is the answer. I'm following this now. Stoicism. Everybody's suddenly declaring themselves to be a Stoic. Yeah, or religion, or CrossFit, or veganism, whatever.

Starting point is 01:39:08 Right, right. The biggest fault, I think, to... Crypto, for that matter. You want to talk about religion. Yeah. It's tribalism in that case. Not for everyone, just to be clear, but yeah. So something related to you happened to me on a plane years ago that I think is a good example of this. Long, long ago, I think it was 2008 or 2009, I was on a plane from Amsterdam to the US and I saw a guy reading 4-Hour Workweek. I said, hey, great book. And he goes, it's trash, man.

Starting point is 01:39:42 And I said, really? And he goes, this guy's full of himself this book is trash and and i think about that all the time because this is like was he german guy or i think i think yeah and i've heard a bit of this before yeah so it's like because he found one thing not just like the fine germans i should say outside of the the US, Germany and Korea are my besties. But he found one thing he didn't like about you, and therefore declared all 400 pages of this book to be trash. And I think that's the problem with isms, is that if you're trying to buy into a system... It's all or nothing. And so, if the leader of a movement says something you don't like on social media,

Starting point is 01:40:27 well, now the bubble's popped, you know. It's a fly in my dish. It's a hair in the meal. It's a poo in the pool. The whole thing is ruined. Drain the pool. I think that's page four to seven in your Dr. Seuss. Right.

Starting point is 01:40:40 Oh, yeah, we're back to that. The cat, the alien, and the octopus. But it's like the mindset that wants everything to be a religion. Yeah. You know, and I think that's deeply built into people. Yeah, the reductionism. I mean, it simplifies reality. Yeah.

Starting point is 01:40:54 Right? Simplifies reality. I like that. I mean, you do assume cognitive burden to take the harder path. So, on that note, back to my whole, like, useful, not true, my radical, what did I call it? Radical doubt, super skepticism. Yes. I think we should be skeptical of every ism.

Starting point is 01:41:11 I think we should avoid isms, avoid ideology, and take ideas piecemeal. Yeah. Which means, ideally, you should be open to somebody you don't like taking their good ideas from people you don't like, and the people you do like admitting that some of the things they say, you're not going to adopt that. And when somebody does that, to me, that shows a stronger thinker, a clearer thinker, somebody who's looking at ideas individually instead of just saying, I'm all in on this. I am a such and such-ist. I subscribed to this ism. That to me seems to be a jumping to a conclusion.

Starting point is 01:41:49 It's a punt. It's like just deferring to the ism. Yeah. This is very present for me in the US, and we don't need to go into politics, but with respect to politics, because I am asked frequently, are you a Democrat or Republican?

Starting point is 01:42:06 Oh, wait, I think you're a libertarian. I'm like, I refuse to play that game. If you want to talk to me about a specific issue. Yes. Let's talk about it.

Starting point is 01:42:14 And if you can not just make the case for your argument, but like, ideally, I mean, this is asking a lot, but like steel man, a counter argument just to prove to me, you're not in this to have a shouting match.

Starting point is 01:42:25 I'm like, okay, then let's have a conversation. But as soon as you apply, and I think I'm borrowing from Paul Graham on this of Y Combinator fame, but the more labels you apply to yourself, the stupider you get. I think that's true. It's just like the more you calcify your thinking and or just absolve yourself of thinking, which is a luxury. It's deferring. It's deferring, which is a luxury if you want to, I think, have a really, if you want to be an outlier in terms of the impact you have, the happiness you can achieve, that is a luxury you can't afford is absolving yourself of thinking. Maybe it's a Belker.

Starting point is 01:43:06 Who knows? Maybe like the people who completely don't think and the people who think the most of the happiest, who the hell knows? I think a lot of it's probably out of the box. How much of your, because there are, I'm sure people listening who are going to be like, wait a second, this guy can't be any happier. What kind of alien is this guy? How much of that do you think is out of the box?

Starting point is 01:43:24 Just your code versus a cultivated. happier? What kind of alien is this guy? How much of that do you think is out of the box? Just your code versus a cultivated... Do you know Sonia Lomberski? No. Okay. You know who she is? Nope. Oh, she wrote one of those books on happiness. After I read Stumbling on Happiness, I went, ooh, that was good. That was a good book. And I went to go find other books on the subject. So she wrote a couple books on happiness. She's been studying happiness for decades. Sonja Lombowski?

Starting point is 01:43:47 Lombowski, I think. Lombowski. I'll find it. Put it in the show notes. Show notes, yeah. She said in one of her books that her studies have shown that most people's happiness is 50% DNA and out of their control. And the other 50% is in their control. So the best we can do is just control that 50%.

Starting point is 01:44:02 And so, yeah, I think... Sounds like you're stoic closet oh yeah yeah minus the uh minus the ism yeah right but did i ever tell you about that that you even talked about stoicism a bit and i was like ancient crap and then finally in 2010 i read a guide to the good life yeah Yeah, William Irving, I think. I read it and was like, whoa! Oh my God, I thought this was just me. Like, this is the, everything he's talking about,

Starting point is 01:44:34 this is the way I've been thinking since I was a teenager. I don't know why I picked it up. Maybe I suspect I found out years later that the Dale Carnegie book called How to Stop Worrying and Start Living. You know, I, just as a side note, so I've read that book multiple times. I just went into my Kindle recently to look at my Kindle library, mostly to see whether it was 70 or 80% of the downloaded books that I hadn't read. And I came across that book and I thought, you know what? This would be a good time to revisit this. They're very overlapping.

Starting point is 01:45:02 I just read a couple years ago in Wikipedia or something that that book was basically spouting Stoic values. Makes perfect sense. It's a great book, by the way, folks. How to Stop Worrying and Start Living. By Dale Carnegie. And it was on my grandmother's bookshelf. And I read it when I was like 16. And so here I was thinking that up until two years ago, I would have said, or I did say, all the things that Stoicism says.

Starting point is 01:45:29 I've believed these things since I was a teenager. I thought I made these things up. I thought this was just me being weird. Wow. This was my weird approach to life. But then just two years ago, I saw that Wikipedia entry about... You got incepted by Dale Carnegie. Oh, wow.

Starting point is 01:45:41 Inception, yeah. Wow. But point is, I've been thinking that way since I was a teenager. And it wasn't until the age of 40 that I read an actual book on stoicism. Whoa! This is how I think. But that being said, it's healthier to watch out for whenever you find yourself wanting to jump all in to an ism, even if it's just a book that you just read. And if you find yourself blindly kind of saying, all this this is me this is how i'm going to

Starting point is 01:46:07 live now unless you have the let's call it self-awareness or meta awareness to say okay i'll try all this stuff on for size this is like me putting on a suit right. To see what happens, but not like this is the truth in all caps. This is who I am, identity. That's totally different. See, that's pluralism versus monism. Like the monim is to say, monism is this, it's mystical. The number one is somewhat like magical and mystical. You know, one love, one world, one answer, one way.

Starting point is 01:46:45 It's very appealing, this idea of one. And it's very upsetting to think that, no, no, no, there are many answers and they conflict. And you can believe conflicting things at the same time. Sorry, I accidentally skipped answering your question about, was it either, am I this happy or why am I this happy or why do I think I'm this happy? Yeah, so this researcher who wrote the book, stumbling on happiness said 50-50, and then I dragged us into Stoicism. So that's it. So no, I think I got the lucky roll of the dice, the DNA dice. But also there's another thing I've been doing since I was a teenager that I found out has another name too. So for my whole life, I very often open my diary and just put everything

Starting point is 01:47:28 into there. I write what happened today, but also like the things that I'm thinking. And whenever I come upon a belief that to me feels like a disempowering belief, something that I've said. Your own beliefs. Yeah, my own, something I've said, it sounds disempowering to me. Like, I hate it here. I can't do what I want here. I need to go somewhere else to do what I want. I'll just keep it general like that. Then I'll stop and ask myself, like, wait a minute, is that true? Like, that sounds like a disempowering belief. Let me push back on that. I think that belief might be holding me back. So I'm constantly doubting everything I write, doubting everything I think, doubting everything

Starting point is 01:48:02 I say. And you do this in writing? Yeah, I do this. My fingers just fly in my, you know. So later, I found out that this is similar to cognitive behavioral therapy. So I've been doing this for decades, and now I just found out what it's called. So I just recently read a book on cognitive behavioral therapy and went, oh, this sounds like what I've been doing. Also, in the all roads lead to Rome type of metaphor, CBT, as I understand it, largely based on many Stoic writings. Ah, right, right.

Starting point is 01:48:33 That makes sense. Yeah. So I recommend, and it's kind of the conclusion of the big arc I was on the whole like useful, not true, super skepticism thing, is you asked me last week, how do you change your beliefs like if you say this is the belief i'm holding this is the belief i'd like to be holding right you said like

Starting point is 01:48:52 how would you recommend somebody do that or how do you do it yeah how do you translate that into durable behavioral change right because it's one thing to intellectually recognize this is a disempowering belief it would be much better for me to hold this other belief it's one thing to intellectually recognize, this is a disempowering belief. It would be much better for me to hold this other belief. It's one thing to achieve that and quite a different thing to implement that latter belief in a way that changes your behavior. So I think you stack up evidence. So first, just writing in my diary about, I think I need to believe this. I think I need to believe that the place

Starting point is 01:49:25 I'm in right now is a good place to be, not a bad place to be. I think that would be a more empowering belief for me, that I can use where I am to do what I want, not need to escape where I am, for example. So then I need to just stack up evidence of this. So it's like, once you've decided on the belief that would be better for you to hold, you can always find evidence to support any belief, right? So you could just kind of stack up evidence. And then I find that, you know, we're social beings. So talking with friends about it and asking their thoughts on this or telling them like, I'm starting to think this. And then friends, if they care about you and they support you, will often give you other evidence to support the belief you want to have saying, you know,

Starting point is 01:50:01 that's a good point. My friend Tracy such and such a this, and she had this happen. So yeah, I think you're right on with this new idea of yours. So friends support it, and then you start to internalize it more. And maybe it takes a few days, and you take some baby steps to put it into action, or a big giant leap to put this into action. Like, you know, some crazy things I've done in my life to cut off some options in my life as a giant leap. We can talk about that if you want. But small actions or big actions, you can take the action before necessarily internalizing it. Totally.

Starting point is 01:50:34 You're going to fake it before you make it. Fake it before you make it, yes. Do it before you believe it. Act as if. I should sign up for college. And you're just like, yeah, I should. Oh my God, I just did. Even before you've convinced yourself, you can sign up for college and you're just like you're right i should oh my god i just did even before you've convinced yourself you can like sign up that little form and take that first step to

Starting point is 01:50:49 yeah take that so i think i've done a lot of things like that in my life where to support a new belief i will take an action first and then we all have the desire to be congruent with the actions we've taken so it's like oh look i'm this kind of person now this is my belief now for folks listening who may want, who would find it helpful to have a structured way to cross-examine their own beliefs and maybe take an opposing stance and then gather evidence, there's something called The Work by Byron Katie,

Starting point is 01:51:18 which is very much this. And I found personally very useful, super, super useful. You teased, didn't really tease, you weren't sure whether to open the door or not, giant leaps. So with the understanding that what you do is not necessarily what you recommend for all people, is there an example of a giant leap

Starting point is 01:51:36 that might make for a story? Is there? Yeah, I renounced my US.S. citizenship in 2011. That's a big one. As a way of, I deliberately burned the ships. Yeah. So I have to explain this metaphor because I found that most people haven't heard this tale. But we have all heard of burning the bridges.

Starting point is 01:51:59 So you burn the bridge when you destroy a friendship, a connection with somebody, the bridge between you and another person. But to burn the ships is a reference to some, I think, like a Spanish conquistador that had headed off with three ships to South America somewhere. And when he landed, there were thousands of Aztecs waiting to kill them, and they only had a few hundred men. Of course, I'm messing up the details here. But he turned to one of his men and said, we must not retreat. Burn the ships.

Starting point is 01:52:24 The men need to know that we cannot go back. We must go forward. So I wanted to challenge myself to go forward and not go back. And after 40 years in America, I felt like, all right, I spent the first 40 years of my life here. I want to spend the next 40 out. But what I found is whenever things got tough, I kept wanting to retreat back to my comfortable California. So I thought, I need to burn the ships. So I did.

Starting point is 01:52:53 Okay, I'm laughing because there's so many rabbit holes we could go down here. I'm going to use my creative license as the host of this podcast to avoid most of them. But are you glad you did that? For years, it was one of my biggest mistakes in life. Made it hard to visit family and friends in the US, right? Yeah. I highly recommend when everybody asks me about it. Some people have found out about this. No, no. Handful more will know. So when people would ask me about it, my advice was always do not do it. In fact,

Starting point is 01:53:28 it still is. Somebody just asked me last week. I was like, do not do it. Kevin Kelly had this wonderful saying, the best option is the option that gives you the most options. I love that. And under that wise advice, I think that no, you should not renounce your U.S. citizenship because it's cutting off options. A lot of people seem to want to do it for tax reasons. And even that has, you need to look through that thoroughly. I did not do it for tax reasons. In fact, my taxes went up after I renounced because most of my income is still U.S. sourced.

Starting point is 01:54:03 So now that all gets taxed at flat 30% rate instead of before it was like part of a bigger picture. So yeah, my taxes went up and it reduced the options. So there was something scary that happened. Just a few months after I renounced my citizenship, my ex, her dad was like on his deathbed and we needed to quickly get on a plane that night, but I didn't have visa. So I went to the US embassy to get a visa quickly and they rejected me. And I was devastated because they just hand you a slip saying, no, you've been denied for visa next. And the slip says, you may not reapply. This decision is final. And hey, useful, not true. I challenged that rule. I was like, all right, I think somebody just made that up. I'm going to go back and reapply anyway. So I went back with a mountain

Starting point is 01:54:44 of evidence and luckily they granted me a visa. Mountain of evidence for what? I was living in Singapore at the time, and it was actually my good friend from Bangladesh that said, Derek, this is your first time being refused? She's like, I've been refused like five times. Look, here's how to do it. You can't just go to the embassy and say, give me a visa, please. You have to show a mountain of evidence that your life is in Singapore, that you have,

Starting point is 01:55:04 tell them about your cat, that you have a job, that you have this, that you're on the board at this company, that you're speaking at, you know, National University of Singapore. Show them your two-year rental. You're not a flight risk. Right. Not a flight risk. So I went back with a mountain of evidence and a letter from the doctor from my ex's dad saying, you know, please, he only has a few days to live. Please allow them to come back. So I was granted the visa, but it was scary as hell. And so I think that people are often overconfident thinking like, hey, I'll just renounce my citizenship and it'll lower my taxes. I can go back anytime I want. But not true. Yeah. I always say like, no, no, no. Once you renounce,

Starting point is 01:55:39 you might never be allowed in that country ever again. That is not your country anymore. So I do not recommend it. Yeah, I would say in general, not to paint with too broad a brush, but the US frowns upon people who renounce citizenship. Yeah. I'm always aware that I might never be allowed back in ever again. Yeah. Okay. What is another example of a giant leap? Anything come to mind? And that's a huge one, for sure. Moving? Was it worth it for you? So you said, I wouldn't recommend this to most people. And I know we live looking forward and not behind. We can't change the past as far as we know.

Starting point is 01:56:18 Now, 13 years later, 12 years later since doing it, it did come in a little handy in COVID times where I will skip some family drama details, but there was a big, big pressure on me to move to America. And I was able to just kind of say, no, can't do it. Don't have to, can't. And so finally, after 12 years, it came in handy for that. But no, to me, that was, it was a huge thing. And the other giant leaps? Giant leaps. Selling my company came in like an instant moment of clarity of like, God, life is weird

Starting point is 01:57:04 when it's like you can hold multiple philosophies in your head at the same time. Like this is, sorry, this is the whole thing I was talking about with useful, not true is these no beliefs are true. So you can hold them all in your head and just kind of look at them like, well, here's one belief that says you should stick it out when the going gets tough, you need to stay in there and such and such and make that there's another belief that says the rewards to effort ratio is off that i'm spending so much effort and getting so little reward that you should stop another philosophy says and you can just hold these in your head and look at them as as paths you could go down as philosophies you could follow.

Starting point is 01:57:48 And then ultimately you just pick one or you craft one from a hodgepodge, a piecemeal from the other bits. And so in that moment, I was feeling really frustrated with my company. I'd been doing it for 10 years. I was feeling done, like somebody who's been painting a mural for many years or writing a novel for many years. You put the last brushstroke on, you write the last word and you go, yeah, I think I'm done. That's how I was feeling.

Starting point is 01:58:08 But somebody could have argued, like, okay, go take a vacation and come back and get back to work. But I played off some different ways of thinking about it. And in that moment, while driving down Pico Boulevard in L.A., while on the phone with a friend, I was like, that's it, dude. I think I'm done. I'm just going to sell the company. And I decided in that moment.

Starting point is 01:58:25 And it wasn't fully congruent yet. It was just one of many options. But that night I went and called three companies that had been asking to buy mine. And I told them yes. Was there a feeling or a meal or something your friend said that triggered that? He just asked me a bunch of questions.

Starting point is 01:58:43 Like he challenged the things I was saying. He basically did the cognitive behavioral therapy with me. He was pushing back on everything I was saying, challenging it. So for example, I said, I'm sick of having all this responsibility. I don't want to have to do this and have to do that. He said, you don't have to do anything. I said, yeah, I have to pay my taxes. He said, no, you don't. I said, yes, I do. You have to pay your taxes. He said, no, Derek, you need to understand this. You don't have to do anything. What's the dude on Power of Now that sat on a park bench? Do you remember?

Starting point is 01:59:12 Who wrote Power of Now? Eckhart Tolle. Eckhart Tolle. Yeah, I never read the book, but I've heard good things about it. I unfortunately tried to listen to it on a long drive, and don't do that. It's hazardous. It's got a very soothing voice. But he starts out the story saying that at one point, he just went to go lay on a park bench and basically just sat there for a couple of years doing nothing.

Starting point is 01:59:28 And it's a reminder that you don't have to do anything, that everything is a choice, that even paying your taxes, you don't have to. There will be consequences if you don't. But let's always be clear that you're choosing to do it. You're choosing to pay your taxes because you'd rather not have the consequences. You're choosing to pay your employees. You're choosing to go into work. None of these things are things you have to do it. You're choosing to pay your taxes because you'd rather not have the consequences. You're choosing to pay your employees. You're choosing to go into work. None of these things

Starting point is 01:59:47 are things you have to do. He pushed back on that a few times. And ultimately, my value system is such that I most value personal growth. And it felt to me like, I've been doing this thing for 10 years. The bigger learning growing opportunity for me right now is to do something else it wasn't a matter of up or down it was just different yeah so let's segue from personal growth to mentors because many people have had mentors many people seek mentors many people pine after mentors And if they could only get a hold of person X and have a cup of tea or a coffee, pick the brain. Pick the brain. Have a meal. Who would not want to have their brain picked? Yeah. So how would you suggest people ask mentors for help?

Starting point is 02:00:41 Here's what I do. I have three mentors. So anytime I hit a little dilemma in my life, I write a really good description of my dilemma before I reach out to them because I don't want to waste their time, right? My mentors are VIPs. I don't want to waste a minute of their time. So first I write a really good description of the problem and then I summarize it. I summarize the context, the problem, I summarize my options and I summarize my thoughts because I got to make this succinct. I don't want to send somebody a 20-page long email. So I have to make this as succinct as possible.

Starting point is 02:01:12 What does that in practice look like? A half-page page? Yeah, half-page. Like bullet points for everything instead of paragraphs, right? As succinct as I can. And then before I send it to them, I try to predict what this person would say. So each of those three.

Starting point is 02:01:26 Right, right. What anybody would say to this. But yeah, what this mentor would say, what that mentor would say. I know the way this guy thinks. I've read all his books. I know the way. We've talked a lot. I know what he would say.

Starting point is 02:01:37 So then I internalize that. And I address those points that I'm predicting they would say. I'm going to address those in advance, again, to not waste their time. And when you say address them, what do you mean by that? Kind of like how you asked, I said something five minutes ago, and you asked me a question like, can you give me an example of that? Or how do you know this? So it's like, okay, I knew you were going to ask that.

Starting point is 02:01:58 Here's my follow-up. So I'll address those in advance, again, so as not to waste their time. And then again, one last time, I try to predict, okay, well, now that I've addressed those. You have an answer ready for whatever they might come back with. But I include it in the initial summary of the situation. And then, after I've done that whole process, I don't need to bother them anymore, because the answer is now clear. Because I've just done the work of summarizing everything and imagining what they would say. So the truth is I haven't talked to my mentors in years and one of them doesn't even know

Starting point is 02:02:32 I exist. These are my mentors. And so this is how I think. It's kind of like, what's his name? Napoleon Hill talked about the mastermind or whatever. Like he was like, you know, imagine Abraham Lincoln is there. What would Abraham Lincoln say to you? Yeah, totally. So I think that you're right. I also get a lot of emails from people saying like, I need a mentor.

Starting point is 02:02:51 Will you mentor me? How do I find a mentor? And this is my answer. Like, it's all in your head. It's about the summarization of your situation, thinking of it from another person's point of view. You can predict what this person would say. If you're a fan of their books and their podcasts and their talks, you know what they would probably say. So do it

Starting point is 02:03:07 yourself. Who is, if you're willing to share, the person who doesn't know you exist? It was Tyler Cowen. I just emailed him two weeks ago to say thank you. Thanks for your years of service. For his continued inspiration. And he sent me back a tiny little thanks. Seth Godin is one. He knows I exist. We don't talk that often, but I very often think like, what would Seth Godin say? He walks the walk.

Starting point is 02:03:34 He's another example of someone who walks the walk. Very much so. Not as common as you would hope. Yeah. No, that's it. Who's the third? It's actually changing. I don't know right now.

Starting point is 02:03:43 Keith Richards. Bjork. What would Bjork third? It's actually changing. I don't know right now. Keith Richards. Bjork. What would Bjork do? Chuck E. Cheese. That would be great. You know, that's thoroughly useful. Nicodemus. If you have a fictional, a fictional person can be your mentor.

Starting point is 02:03:57 Yeah. You know, like what would, you know, what would Jesus do? Yeah. Like people still do that. Like, okay, I'm not sure what to do. What would Jesus do? That's a perfectly good mentor. Yeah. And I think a lot of people would agree with you. And for those people who might wonder,

Starting point is 02:04:13 I actually do something very similar. Okay. Can you tell? Yeah, absolutely. So I have, I try to spend time with people I admire and aspire to be more like in some capacity, right? Because I do think you become the people you spend the most time with. So to bring up a name that we've already brought up, I think actually a lot about Matt Mullenweck because he's very calm in almost all circumstances. Not all. I know a handful of things that bother him, but he's very, very calm and measured and good at

Starting point is 02:04:47 perspectival knowledge, taking alternative positions, taking the counter position on his own thoughts, his own opinions, his own goals. So I often think when I get dysregulated or upset about something, I'm getting wound up. I'm like, what would Matt do in this? What would Matt say to me? If Matt were in my shoes, what would Matt do? And I've also done that in writing exercises where I actually just sit down with my older self who has figured it out. So if I'm talking to a version of myself who's 10 years older, 20 years older, who has figured this out, what might that older, wiser version of me say? And I just write out the dialogue. And by the end, I'm like, huh, okay. but it is astonishing how often that will give you some type of clarity or maybe relief that helps you to cling less strongly to whatever the challenge or problem or question was that you

Starting point is 02:05:56 had in mind. It's really remarkable. I do something very similar, I guess is what I'm saying. Sometimes even just asking. I get emails about once a week where somebody asks me a big question by email. And then at the end, they say, actually, you don't even really have to answer this. Just honestly asking you the question helped me get some clarity. Thank you. Yeah, totally. Like just the act of opening their email client and starting with it and going, okay, I want to ask Derek Sivers this thing. Yeah. Even if I intend to reach out to a mentor about something,

Starting point is 02:06:32 I still go through the exercise of trying to crystallize my thinking so I don't waste their time. Even if it's a really close friend, like I don't, I, if I don't want to be lazy and I don't want to ask them something that could be resolved with five minutes of Googling or five minutes of introspection. It's like, whenever I go to anyone, I want to be able to say, basically, here's the situation. Here are some of my assumptions. Here's what I've already tried.

Starting point is 02:06:55 Like I've tried a, B, C, D, and E, and I'm not quite figuring it out. And then followed by a super specific question, but the asking the mentors around your imaginary table and doing that homework, I think it's something that I do and I recommend to everyone.

Starting point is 02:07:14 And there is some self-promotion here. I would like to have fewer than several thousand email that come in with like, how can I launch my book? Please tell me. And I'll admit, I actually got oddly shy two minutes ago when you asked me who the third one was, because actually it's been you. How can I launch my book? Please tell me. And I'll admit, I actually got oddly shy two minutes ago when you asked me who the third one was, because actually it's been you in the past. Oh, wow. Yeah, and I didn't want to bother you with things.

Starting point is 02:07:38 So I'm just like, I was tempted, you know, I've got your phone number. I could have just texted you. And I'm like, no, hold on. And I'll just do it for someone. Never mind. Well, hold on. And I'll just do it for someone. Never mind. Well, thank you. You know, I think about you. I think about you, Matt. It's funny you mentioned Seth, because Seth would be on a short list for me as well of people who really think, and more than think, it's question.

Starting point is 02:08:01 Yeah. The musts, the shoulds, the have-tos. I'm like, wait a fucking second. That's nonsense. I feel like you're very good at that, which is part of the reason I've read your first book so many times. No, I'm all shy. Should we?

Starting point is 02:08:18 I feel like we should do two things. Okay. I feel like we should get a slight refill on the scotch and then maybe talk about games the games we play all right getting good at games things of this type so little uh little bathroom and then scotch break we're back cool and for people wondering, we just came back from our bathroom slash break slash scotch refill. This is, I would say, very similar to a lot of our conversations. It's not that different from a lot of our conversations, but I do appreciate how much thought you give to deliverables for the audience. Makes a big fucking difference, honestly. The greater good thing, I think about making an interesting conversation for you, but then there's like how many people that listen.

Starting point is 02:09:13 So it's like, I try to- Yeah, you're good at holding both. Looking at you, but I'm thinking of them. No offense. Wow, we could unpack that for a while. All right, you and your euphemisms. right dark mirror here we come uh cheers man cheers so nice to see you oh thanks again matt i don't know why we think matt's there matt's got the matt's got the fuzzy hat on otherwise known as the boom mic so we're all playing games and i think it's a matter of knowing which games you're

Starting point is 02:09:46 playing outside of some basics. You got shelter, you got food, you cover some of the lower rungs of Maslow's hierarchy of needs. Beyond that, we're all playing different games. So knowing which games you're playing, then choosing the game you want to play. These are important. Why don't I just hand the mic over and let you talk about how you think about this kind of thing. Playing games. Maybe not the proper tee-up, but I'm going to go with it. So it's something that might seem strange about me. That sometimes people say that I seem weird because of the choices I make in life.

Starting point is 02:10:24 You are pretty weird, in fairness. It's a compliment. But I try to explain that it's just because for 10 years or 15 years, I was playing a certain game. I was trying to be successful. I wanted to be famous. I wanted to be a successful musician. I wanted to be rich in that way.

Starting point is 02:10:44 And I did it. And in my mind, by my own standards, I won the game. And when you win the game, say you're playing Settlers of Catan or Monopoly or poker, whatever, with friends. When you win the game, what do you usually do is you stop playing. You say, okay, let's go do something else. I won the game. Even with, say, addictive video games. So have you ever played Stardew Valley? No.

Starting point is 02:11:11 I probably shouldn't. It's adorably addictive. So my ex grew up on a farm, and Stardew Valley is one of those little farming games where you tend to your crops, and then you get animals, and you get money for selling your crops. I think the story behind this game is also very interesting. Made by one guy with a passion for many years. I believe there's a lot of additional context to that that we don't have to unpack now, but people can look into it. It's a fascinating backstory.

Starting point is 02:11:36 But yeah, don't play it because it's digital heroin. Yeah, I mean, it's so good. I mean, okay, let's say if you want to play a great game that is also non-greedy, I found it because it was recommended on a list of like no bullshit games that don't ask you for more money once you're in. You just pay your $9 or something like that up front and then you've got the game forever. Yeah, that's cool. Let's say actually, if you are looking for a new game, it is a great game. Stardew Valley is wonderful.

Starting point is 02:12:09 But it's so wonderful that my ex and I got really into it. She played it for something like 400 hours or something like that. The little clock shows you how long you've played. And at a certain point, she had done everything. She'd made every dish, planted every crop, caught every fish, done every favor for every village or whatever. She was done. But yet, there was this yearning to keep playing because she was so good at it. And I think that the temptation to keep playing, even though the rewards are done, isn't that the definition of addiction? And so, yeah, continuing a behavior, even though it's not rewarding you anymore. So to me, that's what making money is. It's a game that I've decided to stop playing because I got enough. But this could apply to anything. Somebody who wanted to be a successful musician. Oh, there's a great, uh, Gautier. I think that's how they pronounce it. You didn't have to cut me out.

Starting point is 02:13:01 Now you're just somebody that I used to know. Okay. One hit wonder, Gautier from Australia. That was his stage name. And he did a beautiful thing as he has retired that stage name. He's like, there, did it. I had a massive number one hit. I don't want to keep singing that song for the rest of my life. There is no more Gautier.

Starting point is 02:13:23 So now he's just back to his legal name. And he's the drummer and singer in a band called The Basics. And he retired Gautier. He stepped away. Jacinda Ardern, the most recent Prime Minister of New Zealand, after six years, felt that she had had enough. And she quit. Instead of going through the process of running for re-election, she quit kind of midterm and just said, that's enough. I'm feeling full. I'm feeling spent. Serena Williams, I think, you know, quit instead of going longer than she should have.

Starting point is 02:13:54 She quit after 27 years and like that was enough. She hit her point that was enough. Cameron Diaz. I suddenly, after watching There's Something About Mary with my kid, I said, I wonder what ever happened to her. And I looked up and saw that she was the fifth highest grossing actress in America, the highest paid Hollywood actress over 40, and then she'd had enough. And so she just quit to do other things. I should interview her. Yeah.

Starting point is 02:14:13 I love those stories. I mean, she would probably not say yes, but I mean, those stories are fascinating. Yeah. Yeah. Because? People are just like, yep, goodbye. Because I think there's something really admirable about the personal challenge of making yourself do something else. That most of us stay in the game for too long.

Starting point is 02:14:31 So I really admired that Jacinda Ardern did that when politicians are known for trying to hold on to power as long as they can, right? Until they're forcibly removed and kicking and screaming. I really admire that she did that. I was super, super influenced by Felix Dennis' book called How to Get Rich. Which, I just have to say, it's definitely

Starting point is 02:14:54 not suitable for family listening, but the audiobook is exceptional. I think it's Roy McMillan who's the narrator. And I know that because I looked it up because I was so impressed by the narrator. But just listen. Anyway, I just want to second. How's it not suitable? Well, I mean, look, you have a very particular, different orientation on these things, but most parents probably don't want

Starting point is 02:15:18 to listen to an audiobook that's like, yeah, and then I spent all the money on coke and horrors. Okay. That's what I thought you were thinking. Yeah, that is one specific thing. But that's so wonderful that he admitted that. It's funny for that reason, right? Because he's so candid in a way that you would not normally find in most books like this. And unapologetic on other things. The whole thing is refreshingly unusual. I enjoyed it.

Starting point is 02:15:42 I love that book. Okay, so I interrupted. No, it's great. And I read that at a key time. It was right about the time that we met, like 2008. I was just selling CD Baby. And I was suddenly, you know, coming into more money than I could ever spend in a lifetime. And just about that time, ready for our conversation here. He said, If I had my time again, knowing what I know today, I would dedicate myself to making just enough to live comfortably as quickly as I could by the time I was 35. I would then cash out and retire to write poetry and plant trees. So I read that at a key fork in the road moment for me, where I just sold CD Baby.

Starting point is 02:16:28 I had a ton of money. It's like, what to do now? And I read this book from this filthy rich old man being entirely honest. And I thought I should just learn from his experience. And so I took his lesson to heart. And I said, all right. Felix Dennis said if he could do it all again, he would just retire and write poetry and plant trees. And I haven't planted any trees yet, but it's kind of what I'm doing. So if what I'm doing seems weird, it's because I took his advice to heart and I've kind of quit the game. So I think the, here's how we can summarize it, is to say that most people,

Starting point is 02:16:59 I think, go by the inner compass that says, I'm really good at this game, so I should keep playing. But I think we should all entertain the idea. We could say, I'm really good at this game, so I should stop playing. I'm excited to dig into this, because there's so many facets that I want to hear your thoughts on. So first, I want to pick up on something that I did not know, although I guess looking at your history makes some strange sense, but wanting to be famous, you mentioned. You strike me as someone,

Starting point is 02:17:34 and I mean this in a very neutral way, and this is also why I asked you the other day at lunch, what makes you emotional? You strike me as a very thoughtful, but in some ways, unemotional person. Wow. Not in a bad way. You don't have volatile emotions. You don't have strong displays of emotion. And that could be a misread. I admire that about you, by the way.

Starting point is 02:18:00 Just the general, at least from the outside, maybe it's like the duck on the pond, right? Calm on the top and kicking like hell underneath. I don't know. But you have a thoughtful, almost serene contentedness almost all the time that I interact with you. That is my perception. That's true. And that's remarkable. And you seem to have a very, very, very low need for external validation. That's my perception. Yes, that's true. So that makes it odd, or for me, to hear you say, I want to be famous, because I'm like,

Starting point is 02:18:36 what do you get out of fame if that's your constitution? Formerly. Okay, so we won't let that go but check this out you and i have thought for hundreds or thousands of hours about the concept of success yeah what it means to be successful i'm 53 now i have spent almost 40 years or let's say like, you know, 35 years thinking about being successful. Just a few weeks ago, in a podcast interview, somebody asked me, what's your definition of success? And I said, to me, it's just achieving what you set out to do. That's your personal success for that thing. I think it's very individual. And he said,

Starting point is 02:19:24 nothing to do with what other people think of you. And I went, other people think? I was like, no, what? And he goes, yeah, I think for a lot of people, they would define their success through the eyes of others. I was like, why? Why would anybody? And he said, wait, you seriously have never considered that? And I was like, wow. He's barking up the wrong tree.

Starting point is 02:19:37 He's got the wrong guy. In 35 years, I had never, ever, ever for a single millisecond considered success as something that would be seen through someone else's eyes. To me, success has always been hyper-personal. Yeah. So how does fame fit into that? I think a little bit like the things that you talked about being competitive, like your personal tendency to be competitive. I think as a teenager, I was like, I want to get famous. Not like as famous as Prince.

Starting point is 02:20:09 Prince was like a musical role model for me. He was my musical role model. He was an incredible musician. Yeah. I didn't want to be that famous. But like, I don't know, Brian Eno? That's a good fame role model where it's not like he'd get hounded walking down the street. And that was driven by a competitive drive it was more just like let's see if i can do it okay you know just

Starting point is 02:20:31 with that spirit of like i think i can do that i want to try doing that and it was also feeling that what i was doing musically was valid and yeah worth hearing and so a way for people to hear it is to. Someone was asking me recently, because I was describing how excited I was to see you. We haven't hung out in so long. It's been so fun to hang out. 12 years.

Starting point is 02:20:56 God, it's crazy because we also interact virtually. So I was describing to someone that I was excited to see you. And they asked, what made you interesting. Or I don't think they said unusual. It's like, oh, what's he like? What's so interesting about him? And I said, well, part of what's interesting is I don't think I've met anyone who has the combination, outside of you, who has the combination of seemingly no need for external validation, yet being a good performer.

Starting point is 02:21:33 Right? Like, you are a ringleader in a circus. Right. Musician. You're really good at imitation, voices, etc. You enjoy, you seem to enjoy performing almost everyone. And I do mean almost everyone. And I'm only saying almost because it seems too absolutist to say

Starting point is 02:21:56 everyone, but it might be everyone who I know who is a really good performer. It could be comedy, it could be acting, it could be fill in the blank. Had that drive to become excellent doing that because they loved or needed or both external validation. I think it's a very uncommon combination, which is why I was asking you about it. Maybe it is because I just had that life shift where it's like I did it to a certain point. I didn't get as famous as I thought I could, but I was successful enough.

Starting point is 02:22:30 Like I bought my house in Woodstock with the money I made touring. You know, like by my own definition, I was a pretty successful musician. And then just at the time that that was getting boring, I accidentally started CD Baby and I just threw all my attention into serving musicians. So I think that flipped something in my head where it's like, I no longer need the attention from me. I don't need any more attention. I don't need any more validation. Now I don't even need any more money. I really don't need anything from anybody.

Starting point is 02:22:59 But yeah, you're right. I still am socially skilled. I know how to get on stage and talk. Yeah, you're good at it am socially skilled i know how to get on stage and talk yeah good at it really good at it you're a combination of elements that i don't usually see together it's very rare am i blushing you're blushing could be the scotch all right so the next question that comes to mind for me is whether you've always been a satisficer, to harken back to the paradox of choice terminology from Barry Schwartz, or if you've ever been a maximizer.

Starting point is 02:23:30 And the reason I ask is because framing games in the way you have, which is once you're good at a game and you win, it's only natural you'd stop playing that game, is to me the je ne sais quoi, the spirit, the essence of a satisficer. There are people, however, who let's just say they want to be a grandmaster in chess. It's like, this is my game. I win. That is a win on the road of additional wins and mastery to strive to become the best in the world.

Starting point is 02:24:03 Or there's another option, which is someone who has played a game for so long. Let's just say it's finances. They finally win in quotation marks. They no longer need to work to meet their needs, but they have played one game for so long, they don't know what other game to play. And that paradox of choice and anxiety leads them to continue playing the same game. I know so many examples of people who have won. They've won the Oscar. They've made a gajillion dollars, done whatever. They don't have the same love perhaps they once did for that game, but they continue to play it because subconsciously or consciously, they do not know what else to do.

Starting point is 02:24:48 So I know this is a hodgepodge of a question, but it leads back to, I guess, the first, which is, have you always been a satisficer? Oh, wow. Okay, the sub-questions, we are reversing back to that. Yeah, this is a whole series of things wrapped in one. In fact, if you don't mind, I think I might end up answering in whatever order they... So the third category of people that don't know what else they can do, that's the category that, by my values,

Starting point is 02:25:15 I want to physically pick them up and put them into a different scenario. I think it's just, objectively, you need to change now. You need to shake it up. In order to live a full life, you need to see the world from different perspectives. You've been doing the same thing for too long. That, to me, talk about beliefs. That's a belief of mine, which means it's not true.

Starting point is 02:25:36 But I believe that you should change. Just because it's not true doesn't mean it isn't valuable. Right. It's useful. Or, I should put it differently. Just because it can't be proven as true doesn't mean it isn't valuable. Right. It's useful. Or I should put a different one just because it can't be proven as true. Doesn't mean it isn't valuable. I know we're going to get into some semantic rat hole here.

Starting point is 02:25:50 So continue. Those people, I think absolutely should. Somebody needs to shake them out of their, kick them out of the nest, shake them out of their habits, go to something else. I feel the only celebrity death that upset me was Kurt Cobain. All the

Starting point is 02:26:08 others seemed to be like, okay, they've made their contribution to culture and I appreciate them, but I wasn't eagerly awaiting George Harrison's next album. But Kurt Cobain, fuck. It felt like he had so much more to give, but he was miserable. And something like that, maybe not to that extreme, but let's just use that as the farthest end spectrum on this kind of person, that says they're miserable doing this thing, but they feel like it's all they can do. Those people, I just want to physically restrain them and pick them up and put them into another environment to show them you can do something else. It's a bigger world. Or like you're good enough, go to an ashram for two years, you can always come back, you'll be fine.

Starting point is 02:26:50 But just imagine the joy of, God, sometimes even simple manual labor. What is it, the end of the movie The Last Emperor? This guy's been through this big giant arc, and at the very end of the movie he's just picking weeds in a garden because he used to be the emperor, but the Chinese Revolution would never assign him to just be a gardener now. And he kind of found his peace with it. And we all have different versions of that we could do. For the most part, for the last 12 years, I've just been a full-time dad here in New Zealand. You know, I know there are other

Starting point is 02:27:19 impressive things I could have done, but this meant the most to me. What really drove that home for me is I'm an enthusiastic student of history. And I read, for instance, I guess it's Genghis Khan, but who really knows? I don't speak whatever Mongolian or whatever the language would have been. Genghis Khan and the Making of the Modern World. Great book, yeah. Yeah, really good. Especially the first half or so is really exceptional. But I realized, because they mentioned Alexander and the Grey in that book,

Starting point is 02:27:52 and I realized, Alexander is kind of like Madonna. It's got one name. I don't know that dude's last name. Do you? And I've polled audiences. Not a single person has ever raised their hand. I'm like, okay, this is ostensibly the greatest. Well, certainly one of the greatest,

Starting point is 02:28:07 but let's just say the greatest conqueror the world has ever known, given the constraints and technology at the time. Can't even name his full name. So it's just like that impressive, I don't know, I've just become less and less kind of concerned with that. Okay, wait, there were some sub-questions

Starting point is 02:28:23 in that last one. I can rewind. Which, by the way, is totally developed skill. That's not something, this is after doing a lot of podcasts. I just noticed from our walking down the street or walking through a forest and talking, you would pick up on a few words that I said in passing. Two days later, you were like,

Starting point is 02:28:40 let me ask you some more questions about that. I was like, what, how the fuck did you remember that? Yeah, totally trained. Yeah, that's funny. Yeah, which is wild. So I was asking you, maximizer versus being satisficer. Have you ever been a maximizer? Yeah, so just like I think you can't preach minimalism to somebody who hasn't felt the

Starting point is 02:28:59 pain of having too much stuff. Yep. They need to feel the pain of having to look after too many things and having a cluttered house and they go, ugh, I need some minimalism. You can't just preach it to them. So I think it's the same thing with maximizing and satisficing. And I think satisficing is a lifestyle for me now or something that's deeply internalized, let's say, because I've felt the pain from trying to maximize decisions and spending hundreds of hours trying to find the best this or best that or, you know, make the best decision. I mean, God, I write in my journal so much, so many pages on something.

Starting point is 02:29:35 And in the end, I'm just like, I've felt the pain from doing this. Now I need to learn how to say good enough. And now that I put that into action, it was because of reading Paradox of Choice. I said, okay, I need to do this. He's right. Paradox of Choice I said okay I need to do this he's right dude's smarter than me I'm gonna do this so yeah I just internalized it and I did it when I catch myself in a moment see I think like shortly after reading the Paradox of Choice moved to Portland Oregon it's a pretty car focused city the city baby office was out in the far reaches and I needed to to get a car. And I had just recently read Paradox of Choice, and I said, I'm going to give myself two hours to choose a car, maximum.

Starting point is 02:30:09 And so, yeah, in two hours, I did quick research for 30 minutes, went out to some car lots, looked at a few options, went, this one, good enough. I loved that car. Was it the best possible choice? No. Who knows? Well, for you it was, right? Minimizing regret.

Starting point is 02:30:24 Yeah. Two hours. And kind of like the, I don't know who the hyper- Well, for you it was, right? Minimizing regret. Yeah. Two hours. And kind of like the, I don't know who the hyper effective person is you mentioned earlier, but choosing that there are just a couple things that you care enough about. Like, I am glad that Josh Waitzkin is not a satisficer. I am glad that he went all the way down the rabbit hole. I'll tell you, I don't think you'd mind. So I believe that it is Josh who actually said that to me. Where he's like, I basically focus on like one or two things. Oh, that makes sense, yeah. And then the rest.

Starting point is 02:30:52 Right, because he's so intense about those kind of things. Good enough. Yeah, I mean, you have to, right? He's another one who walks the walk in a big way. Right. Yeah. Have you met Josh? No.

Starting point is 02:31:02 He's a real world friend. You guys would hit it off. He's one of those invisible mentors. Not like, you know, officially, but I loved his book, The Art of Learning. Yeah. I've listened to his interviews and I really admire him. And so I have many times wondered, like when I've hit some kind of dilemma or situation, like what would Josh do in this situation?

Starting point is 02:31:20 Yeah. I mean, no social, doesn't read email. There are so many conventions that he bucks. It's really inspiring. Yeah. I mean, no social, doesn't read email. There are so many conventions that he box. It's really inspiring. Yeah. And so it's, I mean, that's kind of one of those, you know, nobody cares what you're bad at things. It's like, I'm sure there's a bunch of stuff that Josh Waitzkin is not good at and he just doesn't matter. Good enough. But have I always been like this? No, I think I had to feel the pain. What did you used to maximize at any point? I think 10 years ago, I overthought the where to live thing a lot.

Starting point is 02:31:52 I was feeling very free after I sold my company. What do you do if you can do anything, but you don't have to do anything? And where do you go when you don't have to be anywhere and you can be anywhere? It's like too much freedom. It's a complete blank slate with no restrictions at all. I wasn't even in a relationship. I was just completely unbound. And so I spent far too long in my diary thinking of every possible place on earth I might live and why I could, or I spent hours reading about places that I still haven't even visited, but I learned all about them. I even know what it takes to move there. And, you know, the naturalization law of becoming a citizen there and the steps to becoming a resident

Starting point is 02:32:34 there and the pros and cons of living there. And I've read books about it. Still haven't been there because I did that for many countries. So that's something that was like 10 years ago. I was still maximizing that. And now here we are in New Zealand, where the longest I've ever lived somewhere in my life. Right here. I used to always move around every two years. And I've been right here in Wellington. Parked up. 11 years now. That's wild. It's good enough.

Starting point is 02:32:55 Yeah. I mean, there's a lot to be said for it. I want to say for people listening also that you might think, good Lord, like this is pretty head in the clouds, 1% or stuff in the sense like that doesn't apply to me. That's crazy. But so I would just point out that, God, I got this from a documentary. It wasn't Helvetica, which is a great documentary about typefaces and fonts and so on. Really cool doc. There's another one about industrial design. And there's an expression in that that stuck with me to this day. I think it was from a company or one of the founders of Frog Design, but I could be getting that wrong. And it was the extremes inform the mean, but not vice versa. Something along those lines. It's like when they're designing, say, garden shears, they're not designing for the

Starting point is 02:33:41 average person. They're designing for the edge cases. So it's like the old paraplegic woman who needs to use it from her wheelchair. And then the, I'm making this up, but like the 350 pound bodybuilder who like can't brush his teeth because his arms are too big. Okay. And if you design for those edge cases at opposite ends of the spectrum, you cover everyone. But if you design for the average person, your error rate is going to be really high. And so I've thought about that in so many different domains. So in this case, I'm saying you're providing, from a socioeconomic perspective, an edge case, like broadly speaking. But there are principles in that exaggerated state that are easy to see, that are harder to see in some of the cases that are closer to, let's just call it the middle of the bell curve. So I would just say that we're exploring these

Starting point is 02:34:31 things and the experience of this over-optimizing and paradox of choice and burnt cycles on something like location, I think everyone listening can find somewhere. They can find some place where they're over-optimizing in that way. Thanks for framing it like that. Sometimes I feel guilty speaking candidly about something that's actually going on with me if I know that it doesn't apply to everybody. Whatever I do publicly, I try to make it for them. It's not so much my personal expression as it is me giving back. Like the world's given me a lot. This is what I do to give back.

Starting point is 02:35:12 But it's a nice reminder what you just, the way you just framed it. It's kind of like Felix Dennis writing his How to Get Rich book. Dude was worth 600 million or something when he wrote that. He didn't have to write that book and he wrote about his extreme case. But for me, as a small fry reading it, it was really useful to read what somebody in an extreme situation did and how he made his choices. You know what I've been meaning to ask you forever? I'm sorry, wait. I can hold on to that question. Maybe it's too late. I don't give a shit. Fire away. When people ask the question, what would you tell your younger self? What's the real question there? I unfortunately have taken that question literally too often. And you asked me seven years ago when I said, uh, women like sex. Forgot about that. moment, that's what I wanted to tell my younger self. I felt like culture sold us this story that

Starting point is 02:36:05 women don't like sex, that it's something men want and women reluctantly give. And so for like, most of my life, I was trying to be considerate. And so I was not entirely sexless, but mostly. And it wasn't until my late 40s that it was like, oh my God, women like sex. Nobody told me this. Oh my God, this changes everything. I had more sex in the last three years than the rest of my life combined because this newfound insight. And so what would I tell my former self? Well, fuck yeah, that's what I would tell my former self, but that's just me. I don't think that's the question. The question is what advice would you give me, right?

Starting point is 02:36:42 You. No, I'm saying when someone says, what advice would you give me right you no i'm saying when someone says what advice would you give your younger self right but they're really asking is what advice would you give someone who is not where you are but who wants to be where you are that's i think that is the translation what advice would you give someone who wants to be where you are yeah but it's not where you are like how to get how do i get where you are i think that's what people are generally asking, right? Because they don't give a shit what your younger self would do. They care about what they would do, rightly so.

Starting point is 02:37:12 But the answers are actually very different, if I'm being honest. The answers that I would give to some person whose specifics I don't understand are very different from the advice I would give to my younger self. Right. don't understand are very different from the advice i would give to my younger self right because in my case having a history of some very extreme depression and near suicide in college and so on like my advice would be related to self-preservation and recommending perhaps certain tools like meditation like consistent which i had on some level, but I didn't, I think I could have tripled down on consistent exercise, perhaps supervised psychedelic therapies, et cetera, which don't apply to everybody. They just don't. I mean,

Starting point is 02:37:58 I think some of those things might apply to some people, but if someone's really asking, like, how do I achieve X? How do I have the life that you have? Number one, I would say you don't actually know what life I have. You get the highlight reel and you get what I share in podcasts, but you don't have the full picture. So be careful what you ask for. Number two, I don't understand the assumptions embedded in them wanting X. Right? Because if their assumption is let's just say and you and I have seen this in ourselves

Starting point is 02:38:32 and our experience and the experience of many others like once I have X amount of money all my problems just disappear. Like the vapor of mist hit by the rising sun like all my problems just vanish and that is an incorrect assumption.

Starting point is 02:38:47 But if somebody's just asking that at a Q&A at South by Southwest or something, you don't have the time, you don't have the space to unpack all of that. So any answer you give is going to be hopefully helpful, but it could be really misdirecting in a way. It's funny, the nature that these questions come to us in is usually one question asked, one answer expected. But if you think of the physical metaphor, just imagine that you are somewhere on Earth right now. Say you're sitting somewhere in Argentina and a phone call comes in and says, how do I get there? How do I get to where you are?

Starting point is 02:39:25 I think, well, it depends where you are. Are you in Brazil? Are you in France? You know, are you in Finland? Where are you? But that would take a back and forth that we don't have. If somebody asks you one question, how do I get where you are? The only honest answer is, well, it depends. It's not a soundbite. So is the question you've clapped your hands. Is the question you wanted to ask what question I think people are asking when they ask. Yeah. You answered that. Thank you.

Starting point is 02:39:51 Because I've always wondered, it's like, how do I, how do I think of that question? I keep getting that question all the time on podcasts. Like, damn it. This question again,

Starting point is 02:40:00 like what I would tell my younger self. I think it came up again just two weeks ago. It's like, it comes up a good amount. Yeah. I need a good answer for that. Without the snarky saying, I don tell my younger self. I think it came up again just two weeks ago. It comes up a good amount. Yeah, I need a good answer for that. Without the snarky saying, I don't understand the question. Yeah, it's not a bad question. It's just so context specific that it's not just sometimes unhelpful,

Starting point is 02:40:18 but I think dangerous to give too broad a response, to use your sort of geographic metaphor. You just send somebody off in completely the wrong direction. Go east. Take two of these, call me in the morning. Oh shit, I'm in Antarctica. Sorry about that. Yeah, I thought you were in France. Can you go east from Antarctica?

Starting point is 02:40:40 How do they do directions in Antarctica? Yeah, I mean unless you're at the South Pole, you can give from Antarctica? How do they do directions in Antarctica? Yeah, I mean, unless you're at the South Pole, you could give those. I suppose it gets a little tricky, but the good news is there's pretty much nobody there, so you're not going to be giving too many directions to people. They're going to be at some type of base of some type. I've only been once to Antarctica. I actually recorded a podcast

Starting point is 02:41:07 in Antarctica in an outdoor tent with someone, a field biologist and photographer, which was super fun. You know what? I owe All Road Sleep to Matt Mullenweg. I owe him thanks yet again for getting me down there. It was one of my favorite episodes

Starting point is 02:41:24 of yours, that conversation with Matt in Antarctica. Oh, yeah. You know, actually, I recorded two. I did one with Matt, and I did one with, I want to say her name was Sue Flood, but I could be blanking on the name. This amazing photographer. Wow, two podcasts in Antarctica.

Starting point is 02:41:38 Yeah, that was fun. That's what I was asking. Yeah, yeah. That was also, if I know Matt at all, I know that there's probably some scotch involved with that as well. I like how my son spent time with you in Wellington and wanted to ask you questions about Antarctica, and instead he had a more pressing question, which is, what is it like to be 16? Yeah, what do 16-year-olds do? How do 16-year- olds walk and behave? Do you want to explain the context?

Starting point is 02:42:07 We took him to see John Wick 4. So we went to see John Wick 4. Turns out that in addition to biosecurity in New Zealand, the people at the movie theaters are really strict. Yeah, weirdly. That was off point for New Zealand. New Zealand is a wonderfully casual culture. Formalities are very uncommon here, but that was a weird moment of strictness where they wouldn't let my 11-year-old come in to see John Wick, but we were determined to get him in. Even though he's seen and memorized all the John Wick movies. Uh-huh. Yeah, he's seen all the previous ones. He's seen much worse. He's read the Saga comic

Starting point is 02:42:40 books. Highly recommended, by the way. Saga, best graphic novel. Anyway, so he's seen it all. So I went in to try to get the tickets while my son and Tim were out on the street. And he said, can you teach me how to, like I'm 16? How do 16-year-olds behave? We were fortunate. We had some sort of zoo animals in the form of three other 16-year-olds nearby. And so he was trying to mimic it. And I was like, okay, you're very smart. You're very verbally intelligent. He's a very clever kid. And I was like, but the body language and the energy is not at all matching a 16 year old. So we got to work on this a little bit. He had pulled the sleeves of his sweatshirt, his hoodie up. And I was like, I'm not sure that's

Starting point is 02:43:22 helping. It might be hurting. You look very conspicuous. And then he pulled down the sleeves to make his arms look longer. But the proportions were all wrong. So he looked kind of like E.T. And I'm like, I think you're drawing more attention than you want to draw. But the whole thing was very cute. He means so much to me that it's, I'm proud of myself that I didn't cry when I told the story about the cardboard box in London. I almost did. Yeah. And your answer, when I asked you what makes

Starting point is 02:43:49 you emotional, was anything related to parenting? Yeah. If you guys have ever seen or go see the song Papa Oute by the Belgian musician Stromae, it's basically this, it was a hit single in France and Belgium. There's a great music video for it of this guy who's basically being a bad dad. And when he and I watched that video together, I always cry. Hmm. Yeah, you're kind of tearing up right now. Yeah, yeah. Wow.

Starting point is 02:44:13 Yeah, it's serious. Which is new in my experience of Derek Severus. Like, seeing this. Why do you think that is? It's so important. The stakes are... Wow. Yeah. are... Wow. Yeah. Shit.

Starting point is 02:44:28 Wow. Yeah, new experience. Gotta collect myself for a second. The stakes are so high that it's like if you do this right, it passes on. Wow. What shit. We're not in any rush. Zero rush.

Starting point is 02:44:44 It's funny also collecting my thoughts on how to say this. I don't have to explain it much. Nobody's asked directly. It's like if you do this right, it passes on for many generations. A kid that's raised really well can pass that generosity of spirit. And then somebody that's raised ignored might pass on that scarcity of spirit, you know? Mm-hmm. Holy shit, I'm not doing this for the media.

Starting point is 02:45:09 This is not like trying to be a captured moment. Holy shit. Yeah, thank you for answering that. This is new, also, I'll say for folks. What a gift that you have something that you respond this way to, though. It's kind of the only thing I do. My ex after we broke up said like, wow, I've known you for so many years.

Starting point is 02:45:30 I've never seen you get mad. I've never seen you cry. I've never even really seen you get upset. I'm like, yeah, I just don't really. Like I'm a happy dude. Yeah, like this is the only thing, but it's like, it's not a, it's not a, obviously like not an upset cry.

Starting point is 02:45:42 It's like, holy shit, this is such a big deal. Derek, we've covered a lot.'m just saying i don't i don't feel like we need to cover anything more is there anything you'd like to to say any request to the audience anything at all before we wrap up you're gonna say this is crazy but still to this day, like my currency, the thing that matters to me more than money, the thing, obviously many things do. I still really like meeting people. Like I just recently went to India. I went to Chennai and Bangalore for 10 days. And I sat down and talked with 50 people in 10 days. I had one to two hour long conversations with 50 people. And a lot of these 50 people are people that I'd been emailing with for years. Like they just contacted me out of the blue because they read my article or they read my book or they heard a podcast and they

Starting point is 02:46:33 emailed to introduce themselves. And here it is 10 years later, now I'm in Bangalore and we finally meet. And it was so damn rewarding. And similar thing, it's like I went to Helsinki, Finland for the first time. And what do I do? I email, say like, who do I know in Helsinki? And there were a number of people that had emailed over the years to introduce themselves. And soon I'm like sitting naked in a sauna with some dude that emailed me because, you know, he read my book. This matters to me more than money. So it's like the reason I do a podcast like this, it's like I'm clearly not selling anything. I don't have a big ask,

Starting point is 02:47:09 but I really like it when people email to introduce themselves, especially if it's not coming with a loaded question like, what would you tell your younger self? You know, what should I be doing with my life? But when people just introduce themselves, it means the world to me. It's really cool to feel connected with people from around the world, to know that I have friends in India or I have friends in Nigeria or friends in Finland.

Starting point is 02:47:34 That's my favorite thing, is hearing from strangers. So honestly, like my website, which I made myself as a static HTML website, speaking of our earlier tangent, if you go to sive.rs, yeah, just send an email and introduce yourself. That's my surprising conclusion. Do other domains point to that? It used to be sivers.org. Yeah. You still have that, I assume. Yeah, I'm keeping that forever. But that's my minimalism thing. At one point I looked at that, I'm like, dot org. Where is rs? Serbia. Republic of Serbia. Okay. But one of my favorite tech sites is Lobsters. L-O-B-S-T-E dot R-S.

Starting point is 02:48:10 Okay. I was like, hey, Lobsters. Wait, what the hell is Lobsters about? Oh, it's just a random domain name they got. But it's programmers and sysadmins talking tech, and it's fun. It's like Hacker News minus the business. Oh, I hope I didn't send a bunch of traffic that way. Yeah, I looked at the.org. I used to have Sivers.org, and I looked at that.

Starting point is 02:48:27 I was like, I'm not really an organization, am I? Those four characters aren't really necessary, are they? I was like, I think I could reduce those. And so, yeah, S-I-V-E.R-S. All right, so Sivers with a dot between the E and the R. Yeah. Perfect. Yeah.

Starting point is 02:48:44 Thank you, Derek. So nice. It's so good to hang out and have some scotch and make me cry that was my first time in like three or four years I've never seen you cry wow exclusive to the Tim Ferriss podcast

Starting point is 02:48:58 I was just trying to help out my friend get him some more views yeah mold up the views it was so good to help out my friend, you know, get him some more views. Yeah, get him some more views. Mold up the views. It's so good to hang with. You too. Thanks.

Starting point is 02:49:10 Hey guys, this is Tim again. Just one more thing before you take off. And that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or

Starting point is 02:49:36 discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field and then I test them and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to Tim.blog slash Friday, type that into your browser, Tim.blog slash Friday, drop in your email and you'll get the very next one. Thanks for listening. This episode is brought to you by Shopify. Shopify

Starting point is 02:50:22 is one of my favorite companies out there, one of my favorite platforms ever. And let's get into it. Shopify is a platform, as I mentioned, designed for anyone to sell anything anywhere, giving entrepreneurs the resources once reserved for big business. So what does that mean? That means in no time flat, you can have a great looking online store that brings your ideas, products, and so on to life. And you can have the tools to manage your day-to-day business and drive sales. This is all possible without any coding or design experience whatsoever. Shopify instantly lets you accept all major payment methods. Shopify has thousands of integrations and third-party apps from on-demand printing to accounting to

Starting point is 02:51:01 advanced chatbots, anything you can imagine, they probably have a way to plug and play and make it happen. Shopify is what I wish I had had when I was venturing into e-commerce way back in the early 2000s. What they've done is pretty remarkable. I first met the founder, Toby, in 2008 when I became an advisor, and it's been spectacular. I've loved watching Shopify go from roughly 10 to 15 employees at the time to 7,000 plus today, serving customers in 175 countries with total sales on the platform

Starting point is 02:51:31 exceeding $400 billion. They power millions of entrepreneurs from their first sale all the way to full scale. And you would recognize a lot of large companies that also use them who started small. So get started by building and customizing your online store, again, with no coding or design experience required. Access powerful tools to help you find customers, drive sales, and manage your day-to-day. Gain knowledge and confidence with extensive resources to help you succeed. And I've actually been involved with some of that way back in the day, which was awesome. The build a business competition and other things. Plus, with 24-7 support, you're never alone. And let's face it, being an entrepreneur can be lonely, but you have support, you have resources, you don't need to feel alone in this case. More than a store, Shopify grows with you and they never stop innovating,

Starting point is 02:52:21 providing more and more tools to make your business better and your life easier. Go to shopify.com slash Tim to sign up for a $1 per month trial period. It is a great deal for a great service, so I encourage you to check it out. Take your business to the next level today and learn more by visiting shopify.com slash Tim. One more time, shopify.com slash Tim, all lowercase. This episode is brought to you by Allbirds. Incredibly comfortable shoes, sustainably made with design rooted in simplicity. I am speaking from experience here. I've been wearing Allbirds for the last several months, and I've been alternating between two pairs.

Starting point is 02:53:00 I'm traveling with them right now. I started with the Tree Runners in marine blue, in case you're curious. And now I'm wearing the Tree Dashers, and the Tree Dashers are my current daily driver. I wear them for everything. They're easy to slip on, easy to tie. Everything about them is just easy, easy, simple, simple. I stick with the Blue Hoos, and the Dashers in this case are in buoyant blue. The color pops, I've received a ton of compliments, but putting the color aside, the Tree Dasher is an everyday running and walking shoe that's also great for light workouts. It's super comfortable, and I've been testing it on long walks in Austin. I've also been testing it on the trails and pavement in places like New Zealand. And let's come back to the sustainability. I mentioned that earlier. In the Allbirds Innovation Lab, they research how to make

Starting point is 02:53:42 the most out of sustainable materials like leather made from plants, sugar cane, and tree fibers. In fact, the Tree Dasher is made with eucalyptus tree fiber, something also found in New Zealand, eucalyptus tree fiber to create a lighter and more responsive shoe. Allbirds is making shoes better than natural. They are super natural. Find your perfect pair at allbirds.com today and use code Tim, that's T-I-M, for free socks with a purchase of $48 or more. That's allbirds.com using code Tim, A-L-L-B-I-R-D-S.com. One more time, allbirds.com using code Tim.

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The Tim Ferriss Show - #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life”

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The Tim Ferriss Show - #668: Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life”

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