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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Optimal, minimal. At this altitude, I can run flat out for a half mile before my hands start shaking.

Can I ask you a personal question? No, I would have seen it in a perfect time.

I'm a cyber-nerdy organism, living this year over a metal endoskeleton.

Hello, boys and girls. This is Tim Ferris, and welcome to another episode of the Tim Ferris

Show, where it is my job to deconstruct world-class performers of all different types.

My guest today is a dear friend, and this turned into a 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, 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, S-I-V-E-Dot-R-S, and you can also type in Sivers

dot org, and it'll go to the same place, but he likes the S-I-V-E dot 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 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, 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.

First of all, cheers. Cheers. Nice to meet you, Matt. Yes, Matt Malawake. Thank you for the

Scotch Blend, which we shall enjoy here. So I'll take a sip first.

We have Scotch. We have Go-Go Gadget Black Tea. What is this called again? Go-Go-Goa.

Go-Go-Goa. Yeah, Go-Go-Go. It's so good. Go-Go-Go-Go. Go-India, you know, the region. Yes.

Yeah. So this is otherwise known. I do have a backup of Diet Coke and Case. This is

Podcaster's 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. 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. 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, no, that's all I got. I just have these 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 from my kid so that he wouldn't break them. So I have a feeling

we will come back to this, in a sense, because there's 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 you are sort of outside in the world attire, 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 a 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. 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 tailoring. Yeah, tailoring. And so he recommended this guy, Michael Brown in London.

So, you know, I went to Michael 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, and 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 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 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 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,

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. And one of the bits of advice was

along the lines of, yeah, you know how you have that bad pen? It's like, throughout the bad pen.

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.

Yeah. Yeah. You're only as good as the worst pen in your house.

So let's start with a story now. And I have not heard this story because you began telling me,

and I said, no, I don't hear it. I said, let's save it scuba diving. That'll be my scuba diving.

Scuba diving. That'll be my cue. And what it taught me about empathy and identity.

Amazing. I'll listen to the TED talk.

I was in Iceland, and I never had any intention to go scuba diving, but I was at that place

in a Thingvillier 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. I was like,

I want to go in there. It just looks like avium spring water 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 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 to scuba? Yeah. Okay. And so the swimming

pool was great, and I love the fact that it's calm, that you don't 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 that you like. 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, no, I just, I got to get out of here. So I wrapped on his tank,

and I went up to the top. 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. 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. Then 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 we're to leave 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 the way into new flow. And I went,

All right. Yeah. What was I scared of? So I'm 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. 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 again.

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 fissure there in Thingvillier. I was like, wow. And at 20 meters down, I just

for the Yanks 60 feet or so. Yeah. I just pretty deep. I mean, that's a deep dive. The 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 is not there. And I do the dive manners were taught where I gave her the okay

symbol. And she gave the not okay symbol. And I was like, wait, did I remember it? And I was like,

okay. 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 onto her BCD held onto mine,

inflated hers a bit, asked if she needed my mouthpiece. And she said, Oh, 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 I hate this.

I feel bad that 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, 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 calmed down. And then her boyfriend showed up. Where the hell is the boyfriend? I don't know.

You're on your own baby matter here. 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. So then I have no respect for that kind of silly panic. But I had just panicked.

And it was involuntary. And it's like that night, I had this moment of just like, well,

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. 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? Addiction, 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 these categories might be me, or anybody else, if you're, you know, 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, millionaire. So people in the past few years have become millionaires,

which is something that they held in a different category. And I'd never be that. And suddenly

they're, you have to admit, I'm a multimillionaire 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, 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 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 in these labels that are applied.

And as much as I love Stoicism, even though I invoke that name, I do think that you have to be

careful with labels. So how do you think about that for yourself? Well, time for a supposition.

Well, young men, 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 a forest and whatnot, that it's hard to remember

that we need to close tangents today. Usually we open a tangent and close it two days later.

Yep, that's very true. 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. And he picked this up from me, right? So he's like,

I hate olives too, but he was just imitating me. 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. 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 fourth. Anything you want, right? Yeah. Yeah, I recommend, I recommend people check

it out. I've read it multiple times. It's a great book. Thank you. I love that you did the

forward. Yeah. Thank you. Yeah, you're welcome. For years, I kept calling myself an entrepreneur

until one day I realized like, wait a second, this is expired. Somebody who is 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.

The 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 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, 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, dinner.

Revising, say, we use language, we're creatures of language. I mean, part of the reason that we

become such a dominant pest on the planet is our ability to 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 is just like a waste

product. A metabolite of your other focus. It was like, it was like, and as I'm doing my thing,

if I learn some lessons, there, I just put them into writing. 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 people as we want to be like them. So that kind

of reveals what your values are. 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 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 really lucky and become a billionaire doing something. 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 feel pretty mixed about it. I'm a little embarrassed to tell

you about my new startup then. Right. So it's asking yourself, what kind of people do you want

to be around? Decentralized blockchain, baby seal clubbing, expeditions. Not sure I want to

hang out with the people who might go on that tour. Run by AI. We may need a refill. Gosh,

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 I'm at right now. Like 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? 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. 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. 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. Somebody took the 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. 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 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, we were walking down the street here in Wellington,

beautiful Wellington, New Zealand. Well, yeah, the central area is a little bit like

Haydnashbury in some respects, but for the people to 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 in SFO. You have Monterey Pine here. 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're 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 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. You'll ask me something like that. And in the moment,

as we're walking down Courtney Place, I'll give some half ass answer. And then later that night,

I'm like, Ooh, I mean, I'll push back a little bit. Yeah, 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 as 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 uncomfortable with having all this stuff, all this miscellaneous,

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. 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. It's poor Tim. It's very incapable. 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. 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. And it actually

reminded me of something I think you said in four hour 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. Yeah, freeway. Yeah, there's a lot of that in fitness overall for sure. So

there's an incentive. This is the tech equivalent of that 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 made a

better sales pitch saying, no, no, no, give us all your stuff. We'll take care of it forever.

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. 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 under 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

our kid? He went there in Google photos. She said, no, they're not. And he looked up. He's like,

oh my God, I 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 only said, well, could you please

recover them? And 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.

Sorry, that was some snarky. Escape the clowns and the cloud. Escape the clown. Tech snark.

Okay, so. Oh, you do that on purpose? I did. Oh, that was good. Sorry. So yeah, anytime when

somebody talks about the cloud, you know, change it to a clown. 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 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'm missing something. Maybe you have spider holes dug in

the backyard. I do not experience you to be a hyperparanod person at all. So I just want to

mention that because folks might think, 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? If I just would,

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.

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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. It's just yours, but on a shared computer.

Okay, so it's like a virtual private server. A virtual private server, exactly. I was trying

to not get technical. 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 asexible, always online.

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. 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.

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 here comes 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 your 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 OpenBSD.

And we touched on this on the street the other night. The reason I use OpenBSD is because-

Is it Bodger's Sadomaschism? So, no, no, sorry.

Berkeley Software Distribution. Actually, I was born in Berkeley, California, and kind of like

more people named Dennis go into dentistry because there's an affiliation of names,

Freakonomics pointed that out. I always wonder if my affinity with the BSD operating systems

is because I was born in Berkeley. I used to answer 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 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, 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.

And you don't want bugs in your code. That 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-keygen. The type you want 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. 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,

space-t, ed25519, it will ask you for an optional password 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 .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. 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 a quantum computing and so on allows

the current level of encryption to be decrypted more and more effectively. I'm just

just wondering about, well, this is going to take us off on a major tangent. I think it's already,

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 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 and settings. Okay. 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.

You don't get 10% affiliate custody. Absolutely not. Wait till you see the site. It's like

a wonderful, old school nerdy, 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. 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 stock

piles 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 like, 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

in your bread and peanut butter and jam in the kitchen and somebody says,

we can make a sandwich for you in your own home. You think I don't need your help.

For those people who listen to what you just said, they're like, I think I just heard a lot

of cling on. I'm not sure, but I can't parse what any of that means. It sounds overwhelming.

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. This is going to work.

Look at that. So email me. God damn it. Email you. Write a blog post, Derek Sanders.

I will. No, I will. I will. Blog post. What's that?

Yeah, you've only written 5 million blog posts since like 1987.

You know what? I registered the domain name Cloudfree with the .ee for Estonia.

Yeah. So Cloudfree.com wasn't available. I don't know. I just thought it was clever.

No, but someday I'm going to write this up into 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 Derek's service? That's all my photos. That's what I really wanted. 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. You'll 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's like, actually, now you just got to 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 last week at

school and he said, dad, what's this thing with the squares and set up and he hit a home run on his

first try. Oh, wow. It's all downhill from there. Tell him to stop. Exactly. He's 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. 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

CardDAV and a CalDAV server. On your server, this will be the new server that you sync your contacts

and calendars to. 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 to manage your calendar and contacts, you just set it to your

domain name. And suddenly it says, okay, it's 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 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 and at least I ended up using CalDAV a long time ago.

That's since changed. But yeah. So this is not very hard to implement. 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 calendar and contacts. So it feels so important to know that my contacts

aren't being sent to 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. 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 R-sync, 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 a 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 R-sync and it'll just send the newest

three that you've changed. That's it. So R-sync is built in, but you have to manually type R-sync

and 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, 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.

So it's completely free and open source and it does that more like automatic style

instead of manual synchronization. Well, let me pause. So in your particular case,

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,

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 with a different company

in a different country and do it again, do the SSH port thing. Then you can use R-sync or

Syncthing, not just to clone between your computer and your server, but that server and the other

server. I have a great idea. Okay. You ready? Yeah. All right. So this next chapter of Dr.

Searers. Entrepreneur interacting with customers you like who own personal websites, you could create

a service that helps people liberate themselves from the cloud for those who own personal websites.

Anyway, I can, you know, it's just an idea because you seem to be

philosophically aligned with this. Yeah. I'm passionate about it. It upsets me when people

are bound to the cloud or just going to use everything in the company's hand. They were

the dependent on the server. It's about being dependent. It's about the self-reliance. People

who were dependent on others. Like imagine if everybody in their own home was 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.

You can do it. 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? 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 felt when I

recommended BookMyName.com for domains. It was like some super nerd that recommended that. They're

these guys are old school Unix. You want to go with these guys. They're not these new salesmen

trying to 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 R-Sync

right before I shut down my computer, packs 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 server. And I really like that delay because there have been times that

I've deleted something like a whole week later. 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 like I thought I was done with that. Oh, I see. 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. 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.

We love you, Matt. I adore you, Matt. But I think everybody should learn how to do it themselves.

It's not that hard to do an H1 tag, H2, P tag, UL, ULI, AHRF, image source. You can learn it in an

hour. Yeah. 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. Listen, not to push back, but just to stress test a little bit.

WordPress is open source. Why not use it? You could, 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 handed you to the contents of an entire

hardware store. You're like, no, I really just need to cut this. Right. 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. 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. 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. And that's

it. 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. And I say that even if you just do it this way for the first month,

please make your own static HTML web page even. I think it's 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. And then if you need something that another service offers, you'll recognize that you

need it. Yeah, totally. 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 they're 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 to the extent that it's feasible,

I'd love to learn how to do each thing. Yeah. 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 will take care of it for you thing.

So the three things I'm going to recommend, the three different options in order,

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 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. Well, privacy focused.

If you want the luxury full premium suite of 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 the third option is coming. You can host your email yourself

on your own server. It's dead easy to receive a mail. 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, now you're getting on some moguls. Don't try this day one.

Get familiar with the gear first. So I would be curious to know how you'd reply to people

who are listening and they're like mailbox.org in Germany, fastmail. I've never fucking heard

of these things. No, wait, wait, hold on, hold on, which is not to say they're not robust and

amazing and cute as you put it, but they'll say, I have more confidence in Google being around

in five years than I do in these companies, which I know nothing about. Ultimately,

you can have a certain degree of liberation, 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 that people

have about Facebook or Apple or Google that it's likely you might outlive Google and Facebook.

Those of us who are around in the first.com room. Yeah, history repeats. It's certainly

well within the realm of possibility. Yeah. It was unthinkable in whatever 1999 that my

space wouldn't be around or maybe what was that 2003. So how is mailbox.org better in that sense?

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 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, remote servers. Right. So all of this is expecting everybody to fail.

Yeah. Yeah. 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 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

kick and caboodle because it just sounds overwhelming, but like I want to do sort of

a science project with some 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 email. Okay. So you'd start with email.

I think 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. 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. So calendar and contacts

come together, emails 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. Mail sending has become unfortunately

difficult because a lot of things get marked as spam unless you do a bunch of complicated things.

That's right. I didn't even 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, unlike,

It tends to be Gmail. 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, or maybe it is an ESP, like an email

service provider. Oh, it is. Yeah, they guess there are going only. Yeah, I think I wonder,

I think Sendgrid does handle some of this as well. Yeah, they're one of them. So you're really just

using their SIMTi servers just to send the outgoing mail or receiving it privately. So that's my

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. 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. I'll let that one float by. Sorry, didn't mean to

stir up the thing. Yeah, selling Shopify early 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 a cute moment. I just want to say that also, God, 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. I respect your time.

Yeah, I appreciate that.

By the way, I love your email address. Oh, yeah, yeah, yeah. It's basically says fuck off.

Yeah, it's essentially fuck off at Tim Ferriss dot com.

It's not, yeah, it's not that aggressive, but it makes it clear like thing twice before sharing

that email. Don't you dare give this to anyone at Tim Ferriss dot com. That is his personally

email. 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 that I was offline for two weeks. So I brought a

programming book with me. I was like, well, I'm gonna 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. 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 and Ruby and he emailed back saying not ready yet. That's all he said. And so for those

who don't know, that's DHH. David had a Meyer Hansen. And so then Rails came out about eight

months later. 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 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.

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. Became these 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.

But I met him in the green room at RailsConf. Oh, sweet. That's how you met. That's gonna be

cute. Yeah, that's how we met. Wow. So yeah, Toby and I have emailed since and about like joking

about, yeah, sorry I didn't introduce you yet. 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. We're not gonna 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 gonna 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. So we made a plan on the train. I said, okay, if it's raining, we're gonna 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

Marlebin 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. You 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. So

at one point, he was jumping around park benches and met these kids from Croatia,

where they got into a little tickling match. And 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 a 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 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. He's the held hands. And so show was over. We go home. And I took 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? 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, 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, which was a prediction. I think about like, 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 am.

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.

There's nothing on the wall. I didn't know furniture.

Yeah. Except for some mice. Yeah, legitimately. Yeah, I have three pet mice. We were going to

bring them out. 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 like in the water and oh man,

it was nice. And so it was like the night before my offer was accepted. And it was a 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? 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. 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, satisfying. There's maximizing and there's

satisfying. I have no idea you're going to bring this up. This is great. Yeah. Yeah.

That 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. 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 satisfying. 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

satisfying. Like I really took that lesson to heart and have shaped my life around it.

So just for definition terms, right, 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, it's already interrupt. You know what? Like if you were to hear Paul McCartney go,

hey, Jude, you'd be like, whoa, just to hear him sing two notes, to hear you go, optimizing.

That's like, whoa. That's classic. It's classic. You know,

you know, if that is my legacy, so be it. Optimizing. Optimizing. I think what we're talking about is

where to focus your finite energy on 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 a 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. And one of my most effective friends basically has said, I'm paraphrasing,

but he's like, yeah, I optimized for like one or two things and everything else is good enough.

Like I just, I just have to get it to good enough. Nice. 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 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? Or is it 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 maximizes to polarizing a word.

No, you know what I think it is? Yeah. If it's really fun. Okay. If you think it's just actually

really fun to like, maybe some people set up their, 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 it. You know, people who get really into high fidelity

audio 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. 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, same word. Like publicly,

people will be just known for a few things that you're good at. Yeah. All those things that you're

not good at. Nobody cares that you're not good at them. So just let it go. Like, you know,

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.

Yeah, 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.

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, we're about to have sex. Derek, what's happening?

I hadn't had a shower since yesterday. I was feeling greasy, 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 Scott 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 tried to

focus with some success on making fast, especially reversible or trivial decisions.

Right. If it can be undone easily, this is also with money, right? 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. And 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. Like I don't want open loops.

Yeah. Unresolved decisions, sitting unresolved, sitting undecided for a long time.

I feel the weight of those unfinished projects because I'm trying to make it perfect. 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. It's some point. I love the fact that we

say somebody releases an album. You release a book because there's a wonderful double meaning

in that word, 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. All right. I'm going to combine this with maybe another

Siversism. It's not really a Siversism, 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 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 in the last seven years since we last spoke? A thing that's made

a 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 come this way. It's like, oh,

wait, right. 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,

but preach. Here 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 placebo's. So you 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. And number four, refuse ideology. You need to 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. 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 and the alien. 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 what was this one,

am I flipping you off right now? Like, am I angry at you right now? No, just give 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, 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 that 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 they're, that was something they told their kids, because they want their

kids to take care of them when they're older. So they want their kids to believe that family's

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. Why did you get up to have a glass of water and that type of stuff? Can I tell it?

Yeah, please. Yeah. So this is so important to understand that. These are crazy. They're so

bananas. Actually, we'll start with the other one since you know that one. Well, no, no,

but the audience doesn't come out. No, no, no, but we'll do both. But during brain surgery,

the patient needs to stay awake. And so there was a woman. Insomnia. Or I guess they could, yeah.

I don't know the details of this. 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 rather 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.

Yeah. There are a couple more examples of this, you know, a message shown to one eye

and they did something, then they asked the other eye, why did you do that? And every time

the 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, 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 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 in a flight to somewhere was canceled. 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, 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? Not true. Sorry, I'm just, I'm just, yeah, having fun.

Have fun. Because, yeah, not evidence based. Because we don't say I believe in potatoes.

Because 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 as such, 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,

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 like, 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, you know, 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 four hour work week, giving so many

wonderful examples of how you don't have to accept the world's norms. 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. So this is that matrix moment where the bullets are flying

out and he 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.

This, I think begs a number of questions living in a broader society about morally acceptable

or reprehensible behavior. Right. But 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 Center. You have to drive a car, don't drive it into a

crowd of people. You have to just understand that we're talking about a tool not your psychosis

that might lead you to be that 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, I love too risque. Let's do it. 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. It 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 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 attractions. 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 and we're in the park

and 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. And she was 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. And I was like, damn, me too. I was like, I wish we could.

And then I looked around and this park is surrounded. Well, like, you know,

Sheraton, Hilton, Marriott. And it was 11 o'clock and my fairy was leaving it for a clock. Oh,

and there's one detail. She was just in the process of breaking up with her fiancee.

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? 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 he's 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, tomorrow breakfast will be served over here and such and such. And

here's your room and okay, he gives me my keys. 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.

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.

Everything's great. Just decided to catch an earlier ferry. So paying in full. Here it is.

He's 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 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 bit establishment. This is not this is a various reputable hotel. I do not like this. No,

you must not do it. I don't like this one bit. He was getting really angry. Yeah. And I was so happy

because not for the obvious. But like, it was so liberating, realizing that I've done nothing wrong.

Nobody was hurt. This is fully like consensual. He's, you know, they're paid for their room.

And even though he's angry, he can't get me in trouble. Like 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. 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 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 Ava. I don't know her full name.

Bookbear 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 fiancee, though, I want to stand in for some of the audience who will say, well, wait a second.

You said you didn't 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. We're like, well, wait a second. I think you had fun for a

couple hours with someone who is still engaged. How would you respond to people who find that

morally repugnant? They had broken up, but we're still living together because she just hadn't

got yet. Okay. All right. Okay. Fair enough. I wouldn't sleep with somebody's wife.

Okay. Okay. Fiancee. Okay. Got it. 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 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 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 I am 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. 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 utilitarianism, like greatest good for the greatest number of people type stuff.

Yeah, I don't want to speak for Sam. 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.

You're the rules, right? I mean, you want to talk about paradox of choice, like how much

decision fatigue does that remove? 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 1500 different types of toothpaste at the supermarket and having to

choose one in a sense, right? There is a possible decision fatigue there. 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 think about, 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

understand 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

piece 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. 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 non-profit work,

because I actually have a pretty Hobbesian view of human nature in general and think we've probably

was certainly on a planetary level caused more problems than we've solved. And therefore, I

don't feel like philosophy, like hydrophilic, like philic is to love phil is some of 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. I'm actually

in the sand like 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 non-profit

work and scientific research that gets funded through the SciSci Foundation, 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 a lens of morality. And

so you were going to say, well, yeah, for me personally, I guess I just, we have this gut

feeling of what feels right and feels wrong, or sometimes you actually let your head rule that

decision 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. But it's like, I don't need to have some million dollar thing

to make me 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 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 or religion or CrossFit or veganism, whatever. Right. The biggest fault, I think, to

crypto for that matter. You want to have a religion. Yeah. It's a tribalism in that

case. Yeah. 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, that

long, long ago, I think it was 2008 or nine. I was on a plane from Amsterdam to the US and

I saw a guy reading Four Hour Workweek. I said, hey, great book. And he goes, it's trash, man.

And I said, really? And he goes, this guy's full of himself. This book is trash. And

I think about that all the time because this was like, was he German guy? Or like, I think,

I think again, I've heard a bit of this before. Yeah. So it's like, because he found one thing.

Not to slight the fine Germans. I should say outside of 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. Right. And I think that's the problem with isms. Is it if you're trying to buy into

a system, yeah, it's all or nothing. And so if the leader of a movement says something you don't

like on social media, well, now the bubbles 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 and your doctor sees. Right. Oh, yeah, we're back to that. Got the alien and the octopus.

But it's, it's like the mindset that wants everything to be a religion. Yeah. You know,

and I think that's deeply built into people. This reductionism, I mean, it simplifies reality.

Yeah, simplifies reality. 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. I think we should avoid

isms, avoid ideology and take ideas piecemeal, 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 suchist. I subscribed to

this ism. That to me seems to be a jumping to a conclusion. It's a punt. It's like just deferring

to the ism. Yeah. 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, right? Like, are you a Democrat or

Republican? 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. And if you can not just make the

case for your argument, but like, ideally, I mean, this is asking a lot, like steel man,

a counter argument, just to prove to me, you're not in this to have a shouting match. 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 that 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 belcher. 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 gonna 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? Just your code versus a cultivated...

Do you know Sonia Lomborsky? No. Okay, you know who she is? No. Oh, she wrote one of those books

on happiness. Okay. 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. Sonia Lomborsky? Lomborsky, I think.

Lomborsky. I'll find it. Put 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 the control,

and the other 50% is in their control. So the best we can do is just control that 50%.

And so yeah, I think... Sounds like you're stoic. Closet stoic. Oh, I am. 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, pfft, ancient crap. And then finally, in 2010, I read A Guide to the Good Life.

Yeah, I read William Irving, I think. I read it when I was like, whoa, oh my God,

I thought this was just me. Like, this is everything he's talking about. 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 like whether it was 70

or 80% of the download 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. 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. 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, 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. This was my weird approach to life.

But then just two years ago, I saw that Wikipedia entry about...

You got accepted by Dale Carnegie. Inception, yeah.

So the point is, I've been thinking that way since I was a teenager. And it wasn't till 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 of this, this is me, this is how I'm going to 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, 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 monom 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. 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 after something unhappiness said 50-50,

and then I dragged us into stoicism.

So that's that. 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 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 that 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 I say.

And you do this in writing?

Yeah, I do this. My fingers just fly in my head, 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.

Oh, right, that makes sense. 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, you said, like, how would you recommend somebody do

that, or how do you do it?

Yeah, how do you translate that into durable behavioral change? 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 achieve that, and quite a different thing, to implement that

latter belief in a way that changes your behavior.

So I think the stack up evidence, so first, you know, just writing in my diary about, I

think I need to believe this. I think I need to believe that the place 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, 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,

that's a good point. My friend Tracy, such and such, and 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, 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 are big actions. You can take the action before necessarily internalizing it.

Totally. Gonna fake it before you make it. Fake it before you make it. Yes. Even if you decide

like do it before you believe it. Act as if I should sign up for college. And you're just like,

you're at a should. Oh my god, I just did. Like even before you've convinced yourself,

you can like sign up that little form and take that first step to take the action. 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, which is very much this. And I found personally

very useful, super, super useful. You tease, 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 that might make for a story?

Is there? Yeah, I, um, I renounced my US citizenship in 2011 as a way of,

I deliberately burned the ships. 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. 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. 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. Okay, I'm laughing because there's so

many rabbit holes we can go down here. I'm going to use my creative licenses as a 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 moral, no.

So when people would ask me about it, my advice was always do not do it. In fact,

it still is. Somebody just asked me last week, I was like, do not do it. Kevin and 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 US 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 US source. 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 on his death bed 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 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, 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, once you renounce, 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 pay with too broad a brush, but US frowns upon people who renounce citizenship.

Yeah, I'm always aware that I might not 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.

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 let him. Don't have to. Can't. And so finally, after 12 years, it came in handy for that.

But no, to me, that 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 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 in 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 paths you could go down as philosophies you could follow. 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 and just 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. 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 LA, 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 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 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 power of now that went sat on a

park bench? Who wrote power of now? 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. He'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. 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, 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 and none of these things 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 ahold 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? Here's what I do. I have three mentors. So anytime I had 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. 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?

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. 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. 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 tried 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 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 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. He was like,

you know, imagine Abraham Lincoln is there. What would Abraham Lincoln say? So I think that,

you're right, I also get a lot of emails from people saying like, I need a mentor. Will you

mentor me? How do I find a mentor? And this is my answer. 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 yourself. Who is, if you're willing to share,

the person who doesn't know you exist? It was Tyler Cowan. I just emailed him

two weeks ago to say thank you. Thanks for your user 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. He's another example of someone who walks the

walk. Very much so. Not as common as he would hope. Yeah. That's it. Who's the third?

Actually changing. I don't know right now. Keith Richards.

Bjork.

Chuck E. Cheese.

You know, that's really useful if you have a fictional, a fictional person can be your mentor.

Yeah. You know, like what would Jesus do? 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,

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

Mullin, like he's very calm in almost all circumstances. Not all. I know what the handful

of things that bother him, but he's very, very calm and measured and good at

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, doesn't always give you some magic solution, 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 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, 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, 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.

I think 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. And there is some selfish motive here. I would like to have

fewer than several thousand emails 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 in the past.

No, well. Yeah. And I didn't want to bother you with things. 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, thank you for, you know, 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. Yeah. The musts, the shoulds, the have tos. I'm

like, wait a fucking second, that's nonsense. You know, I feel like you're very good at that,

which is part of the reason I've read your first books many times. No, I'm all shy.

Should we? 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 a little, a 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.

Yeah. Like 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 it interesting conversation for you,

but then there's like how many people that listen. 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, we could unpack that for a while.

All right. You and your euphemisms. All right.

Dark mirror. Here we come. Cheers, man.

Cheers. So nice to see you.

Thank you for, 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 playing

outside of some basics. You got shelter, you got food, you know, 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 tea up, but I'm going to go with it.

No, that's fine. So it's, 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.

You are pretty weird. Thanks for this 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. 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, 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

selling your crops. I think the story behind this game is also very interesting.

Maybe 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. But yeah, don't play it because it's digital heroin. Yeah, I mean, it's so good.

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 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.

So let's say actually, if you are looking for a new game, it is a great game. Stardew Valley is

wonderful, 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, it's 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 Gotier. Gotier. I think that's how they pronounce it.

You didn't have to cut me out. Now you're just somebody that I used to know.

One hit wonder, Gotier 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 Gotier.

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 Gotier. 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 reelection. She quit kind of midterm and just said, that's

enough. I'm feeling full. I'm feeling spent. Serena Williams, I think, quit instead of

going longer than she should have. 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. I love those stories. I mean, she would probably not say yes,

but I mean, those stories are fascinating to me. 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.

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 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 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

went to second. How is it not suitable? Well, I mean, look, you have a very particular

different orientation on these things, but most parents probably don't want to listen to an audiobook

that's like, yeah, and then I spent all the money on coke and horrors. Okay, that's one specific

thing. 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. I love that book. Okay,

so I interrupted. No, it was 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 coming into more money

than I could ever spend in a lifetime. And just about that time, I read Felix Dennis' book,

How to Get Rich. And in it, he had this quote that I got ready for 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 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 is 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 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 and I mean this in a very neutral way.

And this is also why I asked you the other day at lunch. I was like, 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, just the general,

at least from the outside, maybe it's like the duck on the pond, right? Come on the on the top

and like 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,

what do you get out of fame if that's your constitution? Like it's formally.

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, 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,

nothing to do with what other people think of you. And I went, other people think I was like,

no, what, 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? I would anybody and he said, wait, you seriously

have never considered that? And I was like, wow, he's barking up the wrong tree. He's got the wrong

guy. 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. Prince was like a musical role

model for me. He was my musical incredible musician. Yeah. I didn't want to be that famous, but like,

I don't know, Brian, you know, 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 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 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 it. We haven't

hung out in so long. It's been so fun to 12 years. 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,

right? Like you are, you're a ringleader in a circus,

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 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 film 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. 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 for me. I don't need any more attention. I don't need any more

validation. And now I don't even need any more money. I don't really don't need anything from

anybody. But yeah, you're right. I still 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. It 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. 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 naturally 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

Grand Master in chess, like this is my game. I win that as a win on the road of additional wins

and mastery to strive to become the best in the world. Or it'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 gazillion 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. 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 the... Yeah, this is a whole... Okay, so the... Series, phase wrapped in one.

In fact, if you don't mind, I think I might end up... Let's do it in reverse. ...answer 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, 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 and... Yeah. That's a belief of mine, which means it's

not true. 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 a different one. Just because it can't be proven is

true. It doesn't mean it isn't valuable. I know we're going to get into some semantic

rat hole here, so I'll continue. Oh, let that go. 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 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 that to show them, you can do something else. It's a bigger world.

Or you're good enough, go to an Ostrom for two years, you can always come back, it'll be fine.

But just imagine the joy of sometimes even a simple manual labor. What was at 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 whenever assigned him to just be a gardener now, and he found his piece with it.

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. I know there are other

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 in the grade in that book,

and I realized Alexander, it's kind of like Madonna. It's got one name. I don't know that

dude's last name. Do you? And I've pulled 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,

but let's just say the greatest conqueror of 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 in that last one.

I can rewind, which by the way has 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 force and talking, you would pick up on a few words that I said in passing. Two days later,

you were like, let me ask you some more questions about that. I was like, how the

fuck did you remember that? Yeah, totally trained. 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 pain of having too

much stuff. 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 satisfying. And I think satisfying 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 make

the best decision. I mean, God, I write in my journal so much, so many pages on something. 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. Dude's smarter than me. I'm going to do this.

So yeah, I just internalized it and I did it. And 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 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. 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.

Yeah. Two hours. And kind of like the, I don't know who the hyper effective person is you mentioned

earlier, but choosing that they're just a couple of things that you care enough about. Like, I am

glad that Josh Waitskin is not a satisficer. I am glad that he went all the way down the rabbit hole.

So I'll tell you, I don't think you in 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. Yeah. And then the rest.

Right. Because he's so intense about those good enough. Yeah. I mean, you have to, right? It's a,

he's another one who walks the walk in a big way. Right. Yeah. So I met Josh. No,

he's a mortal. 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 Waitskin do in this? 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 Waitskin 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 use to maximize at any point? I think 10 years ago,

I overthought the where to live thing a lot. I was feeling very free after I sold my company. It's

like, 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 too much. 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 the naturalization law of becoming a citizen there and the steps to becoming a resident

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 it's 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 out 11 years now. That's wild. It's good enough. 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. It'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 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

like the 350 pound bodybuilder who like can't brush his teeth because his arms are too big.

Okay, 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, right? 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 things and the experience of this

over optimizing and paradox of choice and burnt cycles and 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. But it's a nice reminder

what you just, the way you just framed 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'll give it far 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, women like sex.

Forgot about that. Because to me at that moment, that's what I wanted to tell my younger self.

I felt like culture sold us this story that 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 new found 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? You know, I'm saying what 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, 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, but you really what younger self would do. They care about

what they would do, rightly so. But the answers are actually very different, if I'm being honest.

The answer is that I would give to some person who's specifics I 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 and 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, etc, which don't apply

to everybody. They just don't. I mean, 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

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. 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 and 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 in somewhere

in Argentina and a phone call comes in and says, how do I get there? How do we get to where you are?

People depends where you are. Are you in Brazil? Are you in France? 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 it depends. It's not a sound bite.

So is the question, you 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.

Because I've always wondered, how do I think of that question? I keep getting that question

all the time on podcasts. I'm like, damn it, this question again. What I would tell my younger

cell, 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, but I think

dangerous to give too broad a response to use your sort of geographic metaphor, right? You just

send somebody off in completely the wrong direction. Take two of these, come in the morning. Oh,

shit, I'm in Antarctica. Sorry about that. Yeah, I thought you were in France.

Yes. Can you go east from Antarctica? How do they do directions in Antarctica?

Yeah, 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. 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 in Antarctica at an outdoor tent with someone

and a field biologist and photographer, which is super fun. You know what? I owe all road

sleep to Matt Mulligan. I owe him thanks yet again for getting me down there. It was one of my

favorite episodes of yours, that conversation with Matt in Antarctica. Oh, yeah. Actually,

I recorded two. I did one with Matt and I did one with, I want to say her name is Sue Flood,

but I could be blanking on the name. This amazing photographer. Wow, two podcasts in Antarctica.

Yeah, that was fun. That's what I was asking. 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 is 16-year-old to do? How do 16-year-olds walk and behave? Do you want to explain the

context? We took him to see John Wick 4. So he went to John Wick 4. It 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. Even though he's seen and memorized

all the John Wick movies. Yeah, he's seen all the previous ones. He's seen much worse.

He's read the Saga comic 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? I was like, I'm 16. 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 and his hoodie up. And I was like, I'm not sure

that's 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 ET. 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 you emotional was anything related to parenting.

Yeah. Yeah. If you guys have ever seen or go see the song Papa Ute by the Belgian musician

Stromai, 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. Yeah, you're kind of tearing up right now. Wow. Yeah, it's serious.

Which is, which is new in my experience of Derek Severs. It's like seeing this. Why do you think

that is? It's so important. The stakes are. Wow. Yeah. Shit. Wow. Yeah, new experience.

I gotta collect myself for a second. It's the stakes are so high. It's like, if you do this right,

it passes on. Wow. Well shit.

Hmm. Well on any rush, zero rush.

Hmm. 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 and like past that

generosity of spirit and then somebody that's raised like ignored and might pass on that,

like scarcity of spirit, you know? Hmm. Well, I'm not doing this for the media.

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. I've never seen you get mad. I've never seen you cry. I've never even really seen

you get upset. I mean, 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. It's like,

holy shit, this is such a big deal. Derek, we've covered a lot. I'm just saying, I don't, I don't

feel like we need to cover anything more. Is there anything you'd like to say? Any request to the

audience? Anything at all before we wrap up? You're going to 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 and went to

Chennai in 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. They 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

things like going 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.

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 have friends in Nigeria or friends in Finland. 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 see. Yeah, I'm gonna keep in that forever.

But that's my minimalism thing. At one point I looked at that, I'm like, .org.

Where is RS? Serbia. I thought that was the public of Serbia.

But one of my favorite text sites is lobsters, l-o-b-s-t-e.rs. I'm like, hey, lobsters.

Wait, what the hell is lobsters about? Oh, it's just a random domain name they got.

It's programmers and sysadmins talking tech, and it's fine. It's like hacker news minus the

business. Oh, I hope I didn't send a bunch of traffic the way. Yeah, I looked at the .org,

and I used to have sivers.org, and I looked at that. I was like, I'm not really an organization,

am I? Those four characters aren't really necessary, are they? I think I could reduce

those. And so yeah, sive.rs. All right, so sivers with a dot between the E and the R.

Yeah. Perfect. Yeah. Thank you, Derek. So nice. It's so good to hang out and have some scotch and

make me cry whole shit. Talked life, yeah. That was my first time in like three or four years.

I've never seen you cry. Yeah. Wow. Exclusive to the Tim Ferriss podcast first.

Just trying to help out my friend, you know, get him some more views.

Yeah, she's more views. I'm all about the views. It's so good to hang out. You too. Thanks.

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 subscribed 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

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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

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just go to tim.blog.friday. Type that into your browser, tim.blog.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 is one of my favorite companies out there, one of my favorite platforms ever.

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Machine-generated transcript that may contain inaccuracies.