Revamped Founder with Jason Fried
host: Advik Kapoor
independence versus business responsibilities, happiness, challenges of creativity, finding purpose, nostalgia
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Transcript:
Advik
Let’s start with small intros. So the people who might not know you. I feel like I should introduce myself here, but we’ll go alphabetically. Usually I go alphabetically. So. Derek then Jason. Derek, kick us off with an intro.
Derek Sivers
Oh, sure. Oh, boy intro. I was a musician really, first I was just a musician. I never wanted to start a business. I was just trying to be a great musician. But then I started selling my CD on my band’s website back at a time when nobody was doing that. And so my friends in New York, my musician friends said, “Dude, can you sell my CD too?” So as a favor to friends, I started selling their CD. And then that grew and grew and grew into a company called CD Baby by accident. I ran for ten years until I couldn’t stand it anymore, and I sold the company, and since then I have been writing books about philosophy. That’s me.
Jason
Nice. You know, I didn’t set out to start a business either. And in fact, I don’t really like business. Even though I’ve been in business for 25 years now, at least in this business, 25 years we’ve been going on 37 signals. But I never started it for that. To me, a business is just-- it’s an envelope in which you can do things, and it sort of is the sustaining vehicle to build things within. And that’s how I’ve always thought about it ever since, like when I first started screwing around online and, you know, when I was 15 or something, making software on the side and, you know, downloading stuff and had a BBS. Like, it’s just one continuous envelope to exist within. And so that’s what I’ve sort of been doing for a long time. We’re known for Basecamp and Hey, our email service and now some other stuff we’ve been doing. But I’ve long admired Derek and and how he approaches the world. And the books he’s written. And also, I was going to say, you know, we talked about once briefly before we started recording this, this new pay one software thing. It’s kind of partially inspired, frankly, by your I guess, desire to be completely independent. I think this is the thing that we have in common, which is independence. And you more than me, actually, in a way, because I have a company and employees. So in some ways, even though we run our company fully independently, I have employees. I depend on a lot of other people. People depend on me. It seems like you’re in a really independent spot, which is solo, doing it your own way, which I really admire and respect quite a bit. So, it’s good to finally be here again with you.
Derek Sivers
Thanks. The downside is I miss having a sandbox. That was the feeling I had after I sold CD Baby. Like, literally like a month later, I went off to a Hot Springs spa in the south tip of Japan somewhere like ultimate relaxation, right? Which is a thing I don’t usually do, but it’s like, I should do this. You know, I’ve been head down on my company for ten years. I just sold the company. I should go relax somewhere. So I go to this Hot Springs Inn, and I bring a Charlie Munger book with me, and I’m going “Ah.” And then I read this Charlie Munger book and I think, “Oh, that’s an exciting idea. I want to try that.” And I go, “Ah, I don’t have a company anymore. I can’t try that idea, man.” I miss having a company because it can be a laboratory where you get to try your ideas. Right?
Jason
That is true. It is true. I mean, I couldn’t do more than half the things. Call it 90% of the things we do without other people around to help me do these things so I can see that. Yeah, I do respect the deep purity of your independence. It’s like, just fully, thoroughly honest independence. It’s hard to achieve, actually. And I think it’s very cool that you’ve pulled that off, even if there’s trade offs. I mean, everything has a trade off. You know, you probably want more people around sometimes. Other times I wish I had less people around. You know, but we’re both very, I think very, very happy and satisfied with our position. So it’s, you know, actually I wouldn’t speak for you. Maybe you’re not.
Derek Sivers
No. No. Yes. Yeah, I’m very, very, very, very, very happy. God, even dude last night I was reading my diary from two years ago when I was living with somebody in a bad relationship, and I remembered that I was not happy, but I didn’t remember that I was that unhappy. And reading these diaries from two years ago going, “Oh, God, that’s just sounds awful. I can’t believe I was that unhappy.” But it was my daily diary where just every single day I just put my honest thoughts from my eyes only in a diary. And it’s wonderful to get past that effect we have of rose colored glasses or just not remembering the past correctly, right? Whether you remember it as better or worse than it was, or you just forget to have a daily diary that was written that day that’s honest, is such an amazing tool to look back accurately at the past, which then helps you make better decisions in the future. You know, I seem to remember that when I was in this place, I was happy. And you go back and you look and go, “Oh, I wasn’t that happy there.” Or vice versa. See, I’ve actually just this morning been pondering on how happy I am in the last 20 months, just since breaking up with that relationship.
Jason
That’s awesome. Let me ask you a question about that, actually. Do you--? Because I’ve sort of changed my tune on this. Do you think you can actually learn from the past? I don’t think you can. I used to think you could. I’m not so sure anymore. I think that every moment is pretty unique, actually. And I assume there are patterns sort of. But I don’t know, I don’t know. What’s your thoughts on that?
Derek Sivers
Well, I’ll tell you mine, but you got to tell me yours. Why you think that you don’t. So I think that I do because you just called it patterns. Some things are consistent. So I go through different phases in life, whether it’s moving to a new place, doing a new thing, turning my attention to a different thing for years at a time. But I look back through the long history, like 20 or 30 years of writing private diaries, and I see some consistency. That I’ve always, you know, no matter what changes in life, I’ve always felt this way, I’ve always wanted that, I’m always happiest when, say, for example, monotasking all day long. This is another benefit of having dear friends that you’ve had for a long time is, say, the other day I had one of those wonderful days where I just woke up at 5:30 in the morning, worked on one thing all day long until I fell asleep at midnight. Just mono focused on this one thing, and it just made me so happy. And I talked to a friend right before I went to bed and she said, “You know, I’ve known you for 20 years. Over and over and over again the times you’re the happiest are these days when you just do one thing all day long.” I think, “God, that’s true, isn’t it? Yeah. Thanks for reminding me.” And that’s been really consistent for 20 years. And so knowing that about my past helps me shape my future life that direction.
Jason
I can see that. But let me challenge you on this for a second. Do you think in those previous 20 years, you kept looking back at the previous patterns and saying, “I would be happier if I was like this?” Or were you just like that? And so did you need the previous 20 years of pattern matching to make those choices on a day to day basis, to make yourself happy? Or now are you looking back and going, you know, over 20 years, I feel like I made independent decisions over a long period of time. And it turns out in those cases I seem to be happier. So I kind of wonder, like, were you referring to the past before or are you referring to it now? Yet you’d achieved all that happiness without referring to the past previously?
Derek Sivers
Yeah, I think I over and over again independently. In this case, I’ll just use this one example I have many times where I think I need to do a bit of that, a bit of this, a bit of that, you know, learn some language, get some exercise a little time with friends, a little time--. But then over and over again, the days that I do end up spending doing one thing all day long, I’m at my happiest. I’m my most thriving, my most flourishing. Not by looking at the past, but just experientially. And then luckily, I do log that in my journal. Or I tell a friend or both and yeah. Does that make sense?
Jason
That’s your proof? It’s sort of like--.
Derek Sivers
Yeah, it’s my proof.
Jason
I feel it, but actually it is that, it’s not just a mirage in a sense. Yeah. That’s cool.
Derek Sivers
Because I do forget the past. I don’t look back that often. And that’s why it was a big wow to look at my diary from two years ago going, “God, yeah, I knew it wasn’t the best relationship, but damn, I forgot I was that unhappy. That sucked. Walking on eggshells in your own home, scared to say anything. You know, just around somebody who’s just upset all the time. And God, that sucks.” Yeah.
Jason
Yeah, we’ve all been there. Yeah. That’s tough. That’s tough, that’s tough. Yeah, that’s a good revelation. I think that it’s good to know yourself. Really, it’s really good to know yourself and what works for you and what doesn’t. And then you can’t always be working that way. But that is like your frequency. Like when you when you tune into that, everything seems to sort of resonate better.
Derek Sivers
Yeah, yeah. And based on evidence, not the fog of nostalgia or looking back at the distant past going, “You know, I think I was happiest when so and so.” But to see that daily evidence untainted. I like that a lot.
Jason
I’m too lazy to journal on a daily basis. So maybe that’s why I’m advocating for “I don’t know about that.”
Derek Sivers
Because I’m advocating for not so that I don’t have to. Yeah,
Jason
Exactly. Yeah, perhaps that is it. I don’t know, but yeah, I’ve just come to find like, there’s this sort of place where there’s like a range where you’re just kind of, again, it’s like this resonance, this frequency kind of thing, not like woo woo, but like there’s this place where you feel like you’re most comfortable. And for me, similarly, probably to some degree, although it’s not necessarily single tasking, it’s more just the idea that whatever I’m doing, it needs to feel independent. I don’t want to be doing it because I have to do it, or I don’t want to be doing it because this, that and the other thing happened first, in order to allow me to do this. There’s this real sense of peace for me when I can just do what feels like I should be doing independent of what I’m supposed to be doing, what a path or pattern tells me to do, but actually, like, “Oh, this is what I should be doing.” So that I really enjoy. The single tasking thing. I’m kind of with you on that too. Although, you know, sometimes it can be quite hard for me to do that, given that I have other responsibilities. Like at work there’s a lot of people who require some of my time, so it’s harder for me. That’s one of the things I really admire about, like your true pure independence is you can probably really do just one thing in a day. It’s wonderful. So anyway.
Derek Sivers
So go back one minute. The thing that you just said about doing things for their own sake, not for-- you used to talk more about not having investors. Is it related to that? That when you’ve got investors, you’ve got to please them?
Jason
We don’t have investors. So still, I think that’s partially what ends up happening to a lot of people who are entrepreneurs or they are sort of attached to their own imaginations of an outcome they want. So they have to hit a target because they set it. Like all these things are so made up. There’s a number and it always happens to be a round number and always a larger number than the one you have right now. Like there’s all these things you just make up, you throw a dart and you make it up, maybe you have to hit something because someone else is requiring you to hit that. But most of these things, most of these targets feel very artificial to me. And I personally, we don’t set any targets at 37 signals. We don’t have revenue targets, growth targets, customer targets, any of those things. We just want to like, do the best we can and let the chips fall where they may, basically. And you know, we want to take good care of people. We want to make good stuff. We want to work with good people. But these aren’t like numbers that we want to hit. There’s no KPIs, OKRs or any of these things. We just do the best we can. And it’s in those flows of just trying to do the best you can, because it’s a self-respect thing almost, that I think we as a company and certainly me, feel the best about the work that we’re doing. But yeah investors would almost I think prevent that from happening. Yeah or growth targets or like a desire to exit in two years, like something that’s in the future, which is driving now, which when you get there, you don’t even know if that’s what you would have wanted anyway. I don’t like that. I’m very much more in the moment.
Derek Sivers
Yeah. Yeah. There was a time when some people were suggesting I should go public with my old company, and I’m sure you must have had that long ago. People don’t talk so much about that these days, but felt like it was more of a thing long ago. But wouldn’t that suck? Like, it’s so funny that some people think that’s a good idea. But to me it’s like, oh, it sounds like the worst thing ever. What a way to condemn me to hell. You know, have a public company. Er, brutal.
Jason
Especially if you were the CEO of the public company. I wouldn’t trade with anybody. I would not want that job ever.
Derek Sivers
Yeah,
Jason
It’d be horrifying to me. But anyway, that’s why you and I are who we are and not someone else. I don’t know. There’s plenty of great, amazing public companies, and I’m glad they’re public. And you know, I couldn’t. Although in the past, we tried to convince ourselves here and there that like, maybe we should go public. I don’t know, part of it was like, well, if we went public, it could be kind of amazing because we’re profitable. So there’s this feeling I’ll actually like a couple of years ago we were thinking about this for a minute.
Derek Sivers
Okay.
Jason
Again, you know, this would be 23 years in business a few years ago. We’re like, “You know what, I don’t know. Wouldn’t it be amazing if a tech company that went public actually was profitable? Because you don’t ever see that. So could we be a small company with fewer than 100 employees. We have 60 right now, fewer than 100 employees. It’s been profitable for 25 years. And we hit this profit number that would make it viable to go public. Like, wouldn’t that be an amazing story?” But then we realized, like, we’re doing that for someone else, not for us.
Derek Sivers
Good for you for making a good story.
Jason
Yeah, it’d be a great story, but, like, I’d be miserable the day after. Like, what’s the point of that? You know. So we stopped off that path and we stepped away. And like, now let’s just get back to where we were and who we are. But yeah, it’s fun to indulge for a moment, but it’s good to know to your point. Like, you should know what makes you happy, what makes things worthwhile for you.
Derek Sivers
It’s good to keep considering, because some day the answer might be yes, that there might be a time ten years from now or something when you guys ask yourself that same question and say, “Actually, you know what? For what we both want in life right now, it would make sense. It would be a good way to let this thing carry on with its DNA, set these boundaries or set these rules, and we’ll start to step back. And it can be kind of owned by the world now.” I could see a mindset where that could work. So it’s good to keep asking yourself.
Jason
It is although to bring it all the way back. I agree, by the way. It is really important. I think the hardest thing is when you to get back to the point about the past. We’ve said no so many times in the past that you would imagine that we’ve set a pattern of saying no to that. And if we were to be guided by the past, as we sort of talked about, then it’s very hard to, like, reconsider. Right. So that’s why I kind of like to detach a bit from the past. It opens up the opportunity, perhaps to reconsider more frequently. That said, deep down inside, I think you do track everything that you’ve done and you do know the no’s you’ve said. But I do think it’s easier to say yes to something later if you’re not so driven by your previous decisions. But then again, we’re driven by all the things and a million things we don’t know and a million influences we have no control over. So who really knows in the end why we make these calls, you know?
Derek Sivers
Right. Have you heard of the split? Wait, wait. Okay, wait. Two things. First, I want to add a little story to that. And I’m so glad you brought that up, because ever since I started CD Baby. You know, I started CD Baby at the very beginning of the.com boom, right before like 1997, 98. So right before the.com boom. So of course, just 1 or 2 years into it, people were asking me to sell the company all the damn time, and customer service would forward those emails or calls to me. And after a while I just said, “Just tell them no, just don’t even send them to me. Anybody that asks about selling the company, the answer is just no.” And so over and over and over again, you know, a hundred times a year we were having to say, “No, we’re not selling the company. No.” And then there was just this point, after ten years where it was Christmas, sorry, the first week of January 2008. And I got three requests that came to me directly because they were a friend of a friend and people I knew three requests to sell the company. I said, “No, I’m not selling, I’m never selling. Stop asking.” And then that weekend I went, “Actually, hold on a second. Yeah, I think I’m ready to quit. I’m feeling done.” It was almost like I had been painting a mural for ten years, and I had put the last brushstroke on. I said, “I think I’m done. That’s it. I got nothing more to add.” So I called back those three people. I said, “Yeah, actually, yes.”
Jason
I love that.
Derek Sivers
Sometimes the answer changes.
Jason
Yeah, it’s true. You know this is a-- sorry Advik. We’re kind of taking over here for a second.
Advik
It’s good.
Derek Sivers
Don’t you love that? You saw me laughing a couple minutes ago. I was laughing, Advik said, “Maybe you could do a short introduction of yourselves.” Here we are.
Advik
I’m enjoying it.
Jason
I have something to share about that and maybe we can end this topic for a second. But I’ve always wondered why this is more of an art project, frankly. But like tech companies, successful ones, or like CD Baby or like us, they don’t just shut down, they have to be sold or acquired or IPO or whatever. There’s this amazing Japanese restaurant, it always comes back to Japan, I guess. But in Chicago that I used to frequent called Katsu, he’d been around for 25 years. Extraordinary small restaurant. This guy ran it himself and his daughter was a sous chef. It was an amazing little family run thing. He decided that he had run its course like he was done. You know, he was in his late 70s and he decided not to hand it off to his daughter, but just to close it. He said, “Someone gave me skills. No one gave me a restaurant. I gave you skills. No one’s going to give you a restaurant.” So he wanted his daughter to go off and start her own thing. But it was this thing that I felt this actually pinging of jealousy for a second, that you could actually just say, I’m done and, like, close the door and walk away with no obligations.
Jason
The problem with, like, what you did and what we are doing business wise, is that we had customers that like rely on us to provide case distribution. In our case, we provide services so you can’t just close the door. But it’s interesting that there’s not really another option. In a traditional business sense you can close a door, go out to fishing. I’m done. I’m retired. And these kinds of businesses, you can’t, but I often like--. It’s a weird fantasy. It’s not really anything I would ever do. It wouldn’t make sense in a sense, but that you can just say we’re done. It’s just interesting that that outcome is not really allowed. It’s also irresponsible, but that you can’t just do it. It’s always been strange to me. I don’t know, it’s one of the few businesses where I feel like you can’t just do that.
Derek Sivers
I’d actually love to talk about this for a minute. Okay. By chance, do you ever watch Rick and Morty?
Jason
Sure. Yeah.
Derek Sivers
Okay. Do you remember the episode, by the way? Anybody, I feel like giving a disclaimer. I’m usually not a TV person, but my kid one day said, “You know, people are talking about Rick and Morty.” So we ended up watching every episode together. There’s an episode where the devil sets up a shop in, like, Main Street in the town where they live, where he sells cursed items with the, you know, the deal with the devil, where you can buy this thing and hey, it’s free. But then it will curse you and you’ll never-- you know. And so Rick, being the scientist, figures out what these little special gun. He’s like, “Oh, I see the curse here.” And he sets up a shop across the street that removes curses. So it’s like, yeah, go to the devil shop across the street and then come to me and I’ll remove the curse for, you know, whatever. So he’s loving it and he’s got this like, “Ah, fuck you devil. Look what I did, you know and I made the shop.” And he’s loving it. And then suddenly, like, he’s thriving, he’s happy. And then somebody comes in going, “I need a return on this item.” And then somebody comes in going, “How are we going to do the payable reports? We’ve got to manage the insurance.” And at first he goes, “Yeah, yeah, I’ll take care of that.” And you just see his excitement. He just drops and he goes, “Yeah, you know what? I’m over it.” He pours some gasoline. He tosses a match, he’s like, “Everybody out. I’m done. Business closed.” And that moment, more than anything else in six seasons of Rick and Morty, made me go, “Yes! That’s it.” That’s what it was like when I felt done with my business. It’s like, I’m not doing this for investors. I’m not doing this for-- like, this was really just my little passion project. So when I’m feeling done, “All right. Everybody out.”
Jason
Yeah, it turned into that, I know. Here we are, of course. Look, we’re fortunate that you’re in a position to even decide to sell a business, right? So many people might be listening or thinking about starting something. And here’s two old guys talking about how we can’t wait to be done, which of course, that’s not really what we’re saying. But anyway, it’s an interesting topic. I think you don’t really hear much about it. It’s always like there’s this asset that you’ve built and it must be assumed by someone else, and the true value must be had by someone or it must blossom or bloom into the true value. It’s like I don’t care about the value of the business I care about like what we do, The value is just something that is a byproduct, and it’s odd that you have to service that in the end, that you have to deal with that in the end, which sounds like what a luxury to deal with something valuable. But still, it’s just kind of a thing. That’s odd to me that I never thought about when I first started the business.
Derek Sivers
But I see what you’re doing and I mean, like you personally, or let’s say you and David the leadership doing, are managing your boundaries to help your sustainability. Help sustain your interest and energy into doing this so it doesn’t get enshittified. ☺
Jason
That’s right.
Derek Sivers
Even in your own, so that you don’t get resentful of your business. You seem to manage your boundaries very well to keep it going.
Jason
We try really hard to do that, and that all comes back to feeling like we have a moral obligation to exercise our independence and do things that nobody would give us permission to do or allow us to do. And as long as we’re doing those kinds of things, I think we’re really still quite happy. I think if we fell in line or something, it wouldn’t feel right. So anyway, shall we change topics just so we get some more in here? I love that we can talk about this for hours, but--.
Derek Sivers
Well, that’s our brief introduction.
Jason
Yeah.
Derek Sivers
What’s the next question? Yeah.
Jason
See you next week. Episode two.
Advik
Jason, like I’m going to be on the business side. I’ll just throw the schedule out of the way. Are you really, truly independent then, or captivated by 37 signals?
Jason
Well, I mean, I have a business partner, so David’s my business partner. We have one other person who owns-- actually technically two now. So Jeff Bezos bought a small piece of our company in 2006. That money went to David and I, it didn’t go into the business. So nothing’s ever gone into the business. But then Jeff had a high profile divorce, so that got split a little bit. So we have another shareholder who’s you know formally related to Jeff. But yeah, we’re fully independent in that we don’t have to answer to anybody. No one has any right over us. We don’t owe anyone any money. We don’t owe anyone any outcomes except our customers and we take care of our customers and do the best we can for ourselves. That’s it. Now, are you truly independent? I mean, no, you’re not truly independent. We have to be there for our customers. You can like to be there for your customers, but you’re also not fully independent. You’re beholden to them as well, and to the market and to other things that happen and to things you can’t control, like the economy and conditions and competitors and all those things. So you don’t really get to move through this world fully independent when you’re engaged in it, you know. But I think we’re as independent as we could possibly be as a business like ours. That’s my general take on it.
Derek Sivers
Jason, there’s an idea you might like, and I’d be surprised if you hadn’t thought of yourself. Which is a Purpose Trust.
Jason
Oh, I know you’ve done this. Yes.
Derek Sivers
Oh, okay. You heard me talk about this before.
Jason
Yeah, but not that much.
Derek Sivers
So, do you know what a Purpose Trust is?
Jason
I don’t.
Derek Sivers
Okay.
Jason
I’m learning, so yeah go ahead.
Derek Sivers
So when I was selling. I nerded out on this subject. I’m sure there’s Wikipedia pages about it or whatever, but the idea is that sometimes you create a trust with a beneficiary. You say, “I’m going to put this chunk of money into this trust, and it’s to be left to my grandson when he turns 18. But in the meantime, the trustee is going to look after it. So it’s no longer mine. It’s not part of my estate.” You know, that’s a beneficiary trust. A Purpose Trust is when somebody takes a chunk of money and says, “I’m going to create a legal structure with a legally defined purpose, which is, say, to keep this park beautiful. I love this park next to my house. I want it to stay beautiful. I’m going to put a chunk of money into a purpose trust that’s going to have a trustee that is legally obligated to try to execute the purpose of the trust, which is to keep the park beautiful. So it’ll be invested in ETFs or whatever. And every year, 10% of its value will be taken out and put towards keeping the park beautiful.” And maybe micromanage what that means or maybe you don’t. So it’d be interesting when you guys someday are ready to stop doing what you’re doing to have a Purpose Trust that could say, “We’ve clearly outlined our leadership values and methodology and thought process. We could create a Purpose Trust that will now own the company and legally obligated to execute according to these principles, so it can keep running the way it is and stay alive. Everything that’s currently running can keep running without us under a trust.” It’s an idea.
Jason
That’s cool. Yeah, I mean, there’s so many interesting things. That’s an interesting thing. I mean, I’ve done something similar to that for a piece of land that I own in Wisconsin where like, it’s more of a conservation easement. Similar concept though, that like this can’t be developed, it can’t be turned into, you know, a monoculture, corn rows or soybeans. Like there’s ideas behind it. And there’s some money set aside to do that. So I had never thought about that in terms of like a commercial endeavor. That’s like definitely more of a passion thing, but that’s interesting. Yeah. So you’ve done this?
Derek Sivers
No, I haven’t done it yet, but I’ve been thinking about it for people’s personal websites. So of course, first I thought about mine. Like what happens when I die? I want the domain name to keep renewing, and I want the server to be continued hosting because it’s not a business. But I put a lot of my life into this thing. So yeah, I thought it would be cool if now, while I’m alive, I transfer the ownership of my domain and maybe even somehow the hosting or whatever into a trust that would continue on for 100 years after I die. Like put a chunk of money into it now, almost like paying web hosting and domain renewal 100 years in advance so that if suddenly I die tomorrow, the site can stay there for 100 years. Then I thought, a lot of people have put a lot of energy into their personal website, and I should make a trust that could do this for everybody. And we could kind of collectively pool say, you know, this idea of pay for 100 years of hosting and domain renewal in advance. The trust would be kind of open source-ish. You know, you could see the open finances, see that the trust was not taking money away, but just holding it is just like a non-profit thing to keep people’s personal websites around for 100 years.
Jason
That is interesting. It’s almost like a living library. Well, not living, I guess. It’s a library, sort of but of the web versus--.
Derek Sivers
Yeah. And people say, but what about archive.org? And I’m like, yeah, I know that you can go find an old site, but I mean, really like an inspiration was, I think his name was Sheldon Brown, that had a bicycle website. He was a bicycle aficionado, both for cycling and the bicycle itself. And he had an incredibly helpful personal website where he shared all of his tips about bicycle repair, bicycle maintenance, bicycle upgrading. And then he died. And luckily, you can still go to that exact same URL. The Sheldon Brown or whatever it is, and see everything he ever wrote, even though he’s not alive anymore. Somebody is paying to keep the website up. And so I think there should be more.
Jason
Which is totally different from archive.org to your point. Like you don’t want to go to archive.org and then search, like you want to go to the website that exists.
Derek Sivers
Yeah, you want the link to still work. If somebody in 2002 said, “The best source I’ve ever found is, you know, click this link.” You want that link to still be there on somebody’s personal site, even if they died.
Jason
The thing is, you’d probably need to--. I mean, this would be such a fun rabbit hole because you’d also need to fund in perpetuity hosting companies, because the biggest risk there is probably not that the domain gets reregistered for 100 years, but like the hosting company goes out of business seven years from now and all that stuff’s wiped. So there’d be this like, all these tendrils of-- it’d be interesting to think through, like, what would you actually have to do? It’s kind of like, what, the 10,000 year clock thing. Right? That Bezos, The Long Now Foundation did where they’re like, I remember talking to them about this. The hardest thing apparently with that clock was not the mechanical stuff. So they used the sun to, I guess to keep it on track to some degree. But the hardest part is it’s buried deep into a mountain, so they have to have a window of some sort to see the light, to see the sun, to see the sky. And the hardest problem they had was how do we keep dust off this window?
Derek Sivers
Forever.
Jason
Forever. It’s like not the mechanics, not the seismic bracing. It’s like the dust on a window. And I don’t actually know how they solve that, but it may not actually be solved. But I love that. It’s like, that’s the problem. That’s actually the problem. It’s not all the other stuff that seems like it’d be the problem.
Derek Sivers
That’s where you need to make a religion that says, “Thou must keep dust off windows, or thou shall be smited.” And then you just pass that down for, you know, thousands of years and nobody knows the original reason. But we know that we must dust the window.
Jason
Sponsored by Windex or something like that.
Derek Sivers
Sponsored by Windex. So I think about you know, static websites, Even if somebody built it with a WordPress or a dynamic site generator, but after they die, it will be static. So this idea that maybe you keep a constant static cache of their website, and when somebody notifies you that this person has died, you flip over the domain. So it points to the static cache now so you can stop paying the $40 a month for hosting and just have it be hosted for pennies a month, you know?
Jason
Good point. Yeah, just like static HTML doesn’t require anything. Yeah. Interesting. I like it.
Derek Sivers
I love this stuff, you know. I like anything that keeps the focus on the non-commercialized web.
Derek Sivers
This this initial thing, I forget. How old are you?
Jason
Yes.
Jason
50.
Derek Sivers
All right. I’m 54. So that early non-commercial internet.
Jason
I remember it.
Derek Sivers
When it was just the people making websites because they were that passionate about something, that they just had to express their love for watches.
Jason
Totally.
Derek Sivers
As you know well.
Jason
I do. Yeah. Yeah. I love those days. Those are great days. Yeah.
Derek Sivers
People still actually seem surprised when they go to my website, for example, and they say, “Whoa, what is this? There’s nothing commercial about it. There’s no tracking even. Whoa.” And I go, “Yeah, that’s the way the internet used to be.” I’m not trying to be retro. I just have been doing this since 1995 and just never really got on board.
Jason
The first example with commercially is actually Berkshire Hathaway’s site. Have you seen that recently?
Derek Sivers
No, no.
Jason
Go look at it real quick while we’re on, if you can, Berkshire Hathaway, you will love this. This will give you 1995 vibes.
Derek Sivers
I love it. Yes, it’s it works.
Jason
So, yeah, it’s like you actually cannot make this site better. Like, literally. So the two columns of bullet points, like a message from Warren Buffett annual reports. If you click on Warren Buffett’s letter, it’s like just full width text. I mean, you could probably format that better, but why? It’s just the purest representation of we need to have a website. The information needs to be up here. This is not important, but it needs to exist. We’re going to spend zero time on it. Some webmaster wrote it and whatever. I even love, “If you have any comments about our web page.” Web is in all caps, “Write at the address shown above.” Like there’s not even an email link. It’s just the best.
Derek Sivers
Wow.
Jason
I love it anyway. So it’s like a great example. And also like one of the most successful companies of all time, holding companies. And this is the website they have. And people are like, you need a fancy. No you don’t actually.
Derek Sivers
It’s proof that you don’t.
Jason
Proof that you don’t.
Derek Sivers
Okay. I remember your early, early days of redesigning fedex.com And. And do you remember how much of that was about making things look good on the screen? We all had, which was a 1024 by 768 screen.
Jason
Right.
Derek Sivers
And now, funny enough that that old plain text full width thing actually works better on phones than all those sites that were beautifully designed for a 1024 by 768 screen. Now, the things that were never designed, like Berkshire Hathaway, end up looking better on a phone because it’s just the text with all the formatting.
Jason
Automatically. Another one is like the Drudge Report is another one of those sites. It’s like black and white. One guy maintains it. It’s like a mega, mega news business, whatever it is. But like, it just happens to wrap because it just wraps like in the columns and it works on the phone. I love that kind of stuff where like the simpler it is, the more flexible it is, the more places it works automatically with no additional thought required versus like media queries and like in this viewport, change the thing and scale the thing. So how about just like make it work always or just make it work. So yeah. Okay. What else are we talking about? This is good. I love this.
Derek Sivers
I’m sorry. I’m just cracking up at the the nature of this that I think it’s two. It’s like 3:00 in the morning in India, and he’s like, up in the middle of the night to make this call happen. And he’s just sitting back and he asks one tiny question and we just riff.
Jason
I admire the the effort, I love it. All right. Is it 3 a.m. in India?
Advik
Yeah.
Derek Sivers
Yeah.
Jason
Oh my gosh. Wow. Thank you.
Advik
Yea I have no problem with that. I’m up all night. Usually, I’m weird. It’s like when I was like learning to code. When I was 11, the Berkshire Hathaway site was the one that I used as an inspiration.
Derek Sivers
Really? That’s so cool.
Jason
Really?
Jason
How about that? Amazing. Yeah. You can view the source, and it’s like it’s so old school and it still works. That’s the other thing I love about-- sorry. But anyway, the thing I love about simple shit that just works is it seems to always work. It’s like analog things. A pocket watch from 100 years ago still works today. And yet the more complicated things are the shorter their shelf life. And you invest so much into making this complicated thing, and then it lasts for very little amount of time. But the simpler it is, the longer it lasts. And I think there’s something about simplicity that also gives you durability. Not always, but more often than not, even by accident. You don’t like mean to do that, but it seems to do that. And then it’s easier to repair and fix. And if Berkshire Hathaway lost their webmaster, I’m sure they could hire anyone in the world.
Derek Sivers
Yes.
Jason
Just fix it like versus like some of these sites. It’s like, well, you need to know this framework and that framework and are you up to speed on this and that? And it’s like you look at it’s like code soup and all these includes and it’s like what is going on like this is complicated. So yeah.
Derek Sivers
All right. So Jason, I know that a lot of people that tune into this might be fellow techies. And since Advik just mentioned this site, I got to say, I’ve been a 100% Ruby guy for 24 years now. In fact, I’ve told this story a couple times and I just feel like telling it again now. I got into Ruby in 2002 because I wanted to learn object oriented programming, and I heard that there’s a little language that’s 100% object oriented. So I thought, “Well, what better way to learn than that?” So I got the pickaxe pragmatic programmer’s book on Ruby, learned it over the course of a month, and I was like, “This is really cool, I love it. I wish I could use this to make websites.” And somebody said, there’s some dude in Denmark making a web framework and Ruby. I said, “No way.” And they gave me his email address and I emailed. I said, “Hey, somebody told me you’re writing a web framework in Ruby.” And he sent me a one sentence reply saying, “It’s not ready yet.” And that’s it. And so I’ve been using Ruby for everything since then, for 25 years. I don’t even use Rails. I use Sinatra because my needs are that simple.
Jason
Yeah.
Derek Sivers
So it’s just Sinatra, a PostgreSQL connection, and that’s it. But the Ruby server I was using Thin for the longest time, and I guess everybody else switched to Puma, but I didn’t care because Thin works until rack 3.0. Suddenly the Thin web server doesn’t work and it has to switch to Puma. But then Puma was giving me errors and I went aha! Complexity.
Jason
Like a puma. Yes
Derek Sivers
Like I need two gems, damn it! And even with that little amount of complexity, it got me philosophical about how many things we tie ourselves to.
Derek Sivers
Like this Berkshire Hathaway website example. You’re talking about that when people say, “Well, in order to launch this site, you need to launch a virtual machine to get this.” No no, no, no, you don’t have to. I know that you want to. I don’t want to. And I know it’s not necessary. And I feel like it’s this constant process of saying but that’s not necessary. I’m stripping away everything that doesn’t absolutely, positively have to be there. Even when I was running a company and suddenly I had, you know, 50 employees and somebody would come by and say, “Well, what you need to have now is a privacy policy.” And I’d say, “Do I have to?” And they say, “Well, you really should.” I say, “Will I be put into jail behind bars if I do not?” “Well, no, but it’s a good idea.” I’d say, “Okay. We’re done. Goodbye.” I’m not going to do anything I don’t have to do. And then there was one day where somebody from the state of Oregon came by and said, “Well, you know, after you have 40 employees, you are legally required to have some sign posted in the workplace.” And I said, “Really, legally, like, I’ll be arrested?” And they said, “Well, you will be constantly fined if you don’t.” Went, “All right.” So yeah, I said, “Does it say where it has to be”. They said, “It has to be somewhere accessible by all in the workplace.” And we didn’t have a men and women’s bathroom. We just had one bathroom. So I stapled it to the ceiling in the bathroom. I said,
Jason
There it is, inspector. Come on in.
Derek Sivers
Yes, exactly.
Jason
Yeah. Love it.
Derek Sivers
But so when it comes to tech, I’ve been thinking about even the minor dependencies of Ruby and Sinatra. That now, like, if I say gem, install Sinatra like six other things come with it. Like I’ve got six gems in there. I’m getting a little cranky with this. And I started looking at Go, which is ugly but objectively simpler that just the Go standard library can do everything I was doing with like 6 or 7 gems in Ruby, I’d say, “Well, it’s more verbose.” But if I’m thinking in terms of many decades, it’s more self-sufficient. It’s less dependence on these six other libraries that I’m not going to look after. So I’ve actually been thinking about switching, sorry what?
Jason
It’s more durable essentially.
Derek Sivers
Yeah. Durable. Good word. Yeah. Like you’re talking about the watches. Your watch still works after. What did you say like a 60 year old watch that you tend to wear
Jason
A hundred year old. It could be 300 year old watch. Like anyone today living who knows how to work on watches. A watchmaker can repair a watch from 300 years ago.
Derek Sivers
Yeah.
Jason
That’s incredible. It’s the same technology that’s just very durable, very simple. Yeah. That’s interesting. I think you should follow that urge. Like, that’s your thing, man. Like, what is the least I need? And do it and go for it.
Derek Sivers
Yeah. Even if it’s more verbose, it’s like we all know the beauty of Ruby. And I do love the beauty of Ruby, but I’m still thinking there might be other solutions, like, maybe I could go through the Sinatra code, just take the bits I need, put it into my own library that’s no longer dependent on a remote gem. That’s another solution. But on the other hand, learning Go might be more of a learning growing experience for me.
Jason
You should check with David about this because I think David’s definitely on this tip, which is like we’ve been redoing all of our websites, so there’s basically no build websites, there’s no compiling. It’s just like straight HTML, CSS, there’s no, you know. And it’s incredible. It’s like so much faster. We’re trying to get to the point where you’ll remember this. Like you want to make a change. You used to just like upload a new file via FTP. And it’s like, there it is. Like. But instead of, like--.
Derek Sivers
What do you mean?You’ll remember this? That’s what I do still dude. I’m still doing that.
Jason
You still do that? You’re the only person.
Derek Sivers
I just have an OpenBSD server and I use SFTP to upload the new HTML file I changed. That’s what I still do.
Jason
Well, you’re everyone’s hero there. So most people don’t do that. But we’re trying to get like back to that because it’s better. It’s actually frankly better. It’s better. Now if you have 7000 employees it’s not better. But like we’re not. And this is the other thing that always bugs me is like small companies they follow the work practices of huge companies and it makes it so much harder on them. I’ve been thinking like I always think in terms of slogans. For some reason, I don’t know where I got this from, but it’s like, “Easy shouldn’t be hard.” Is what I’m just constantly telling myself. Easy shouldn’t be hard. And people make things so much harder on themselves, especially for like what they’re actually trying to do with the actual outcome is. The thing you’re trying to do is not that complicated, but you make it so complicated that it becomes so convoluted and so dependent on all these other things. So I think you should follow your instincts there. If you found something that’s like simpler, better, and also like there’s enough happiness attached to it, go for it. Yeah.
Derek Sivers
You’ve seen Rich Hickey’s talk called “Simple versus easy”.
Jason
Gosh, I feel I’m almost certain I have, but not recently.
Derek Sivers
Oh, yeah. Okay, dude, then you clearly haven’t seen it recently because of what you’re saying. The, “Easy shouldn’t be hard.” You need to go watch this again. He actually gave the same talk twice. Once at Strange Loop, and then once, the Ruby guys invited him to speak at Ruby Conf or maybe it was even RailsConf. So find the Ruby Rails version. It’s actually a little bit better. He condenses it a little further. And my favorite line in there, is when he says. Okay, well, actually, here, I’ll give you a couple of the quick highlights, but you have to watch the whole 40 minute thing because it’s a masterpiece. I think it’s my single favorite talk anybody’s ever given ever, that I’ve ever seen in my life is this talk. I think about it all the damn time because he goes into the origin of the word complex, which he said, it’s a version of the verb complect. To complect is to braid things together. So complex means that something has been complected, braided together. It’s dependent on other things. Simplex is the antonym of that, which means unconnected, unbraided. So simple is an objective measure that means it’s not tied together with other things.
Jason
Yeah.
Derek Sivers
Easy means close at hand, whereas hard means, you know, something that you that requires a lot of effort.
Jason
And that’s interesting.
Derek Sivers
So he said that, “It can be very easy to do something very complex.” He said, “It’s very easy to type gem install hairball.” And he said, “Great, look how easy that was. Now you’ve just installed hundreds of thousands of dependencies, but it was easy.” And he said, “It can be very hard to make something simple. It can be extra effort you might have to learn a skill you don’t already have and work harder to make something that’s simple.” I think about that all the damn time. Even with life, even not just programming, but like to make my life simpler might be harder, but ultimately simpler.
Jason
Yeah. Well, it’s a time scale thing. Like in the moment it’s harder. But you’re not alive just for that moment, hopefully be alive for a million more moments. At some point, the time scale becomes like, yeah, this would be simpler, more of the time with my remaining time, if I do it this harder way at the moment. Yeah.
Derek Sivers
That’s a nice way to put it. Wait. Hold on. Can you say that again?
Jason
I just came up with it. So let me see if I can remember. Basically, the point is, you’ve got many, many, many moments left, hopefully. Right. So if you can think about having a million moments left and it takes three complex moments to get this thing done right now, which you feel because they’re right now, but you’ll have all these extra moments down the road that are much simpler because you spent the three complex moments now, basically, that’s not what I said, but that’s kind of--.
Derek Sivers
Three hard moments now. Yeah.
Jason
Yes, yes. Like, yeah, you do the hard thing now. So you have the easy things in perpetuity essentially as long as you can
Derek Sivers
I like that. Yeah. Harder now. Simpler future, which means easier future. Even if it was a harder present to make that simpler future. Oh yeah, that’s getting almost sloganish for you.
Jason
Yeah. There’s a slogan there.
Derek Sivers
Harder now to make. Yeah. Harder now to make a simpler future easier.
Jason
Yeah. There’s that one saying, like, “Hard decisions, easy life. Easy decisions, hard life.” It’s kind of like that, sort of. But I think timescale is a really important thing to think about with any of these things, which is like, what’s so hard? Well, okay. Like how much is left? Well, seven years we’re going to have this thing. Well, if you want it to be hard for seven years, or do you want it to be hard for three days and then, you know, six and change easy. So I think it’s really important. And the problem I think, is that when you don’t have a long term point of view, everyone tends to sort of take the shortcuts and the short term because that’s all they can see. Now nothing’s guaranteed. All we have is now anyway, really, basically. But like hopefully you assume you have more than that or many of these in a row. And I think a lot of companies, especially in tech, given the fact that everything’s a short time horizon, people are building things to scale or sell or whatever or IPO or whatever it. Yeah, sold off and merged or something, is that they don’t they don’t think about what’s right or what’s easier over long periods of time. So they take easy over short periods of time and they leave. The opposite of that is typically not always, but typically a very complex trail behind them, a really messy wake. And I think that’s sort of the thing we try to always avoid, because we’re going to probably end up wanting to live with our consequences in our business.
Derek Sivers
Dude. Yeah, that was really wonderfully put. Thank you. That’s such a--.
Jason
I can’t say it again. So hopefully someone recorded that because these are stream of consciousness things. I don’t know, I don’t know where they go. But good, I’m glad that landed somewhere.
Derek Sivers
Do you know this is the reason I enjoy doing podcasts. Is for one it sparks conversations that are almost required to be interesting to do your job well as a podcast guest you’re supposed to be interesting. But then I love that they’re being recorded so that when a little moment like that happens and you say something off the cuff and I say, “Oh, ooh, can you say that again?” You’re like, “Oh, I don’t know. Let’s find out.” I love that it was recorded and captured, and then I end up taking the transcriptions from these things and saving the transcript for myself. Like, what was that thing I said two years ago?
Jason
You don’t have your own podcast, do you?
Derek Sivers
No, because I do this, I am a guest on others. I counted this is number 153 for me. I’ve been a guest on 153 podcasts now.
Jason
You’re organized.
Derek Sivers
And you know, keep them all in my PostgreSQL database and when I’m talking with friends, I’m usually the guy asking questions more. And I like that standing here in my recording booth, trying to be a good guest means I have to come up with new insights that I haven’t said before. It’s a good challenge.
Jason
It is. I agree. Advik how about you? What do you think?
Advik
I always have to ask the questions. And I think like on the same point of the hard things, how have you guys developed the intuition that the hard things that you solve right now are not the hardest you will ever solve?
Derek Sivers
How do you mean? The hard things you’ve seen now are not the hardest we’ve ever seen. How do you mean?
Advik
It’s like the three hard things for example, if I go on the same line as Jason. The three hard things that you are trying to solve in the moment, how do you know that those are not the hardest that you ever faced, or the hardest you will ever face, like on a scale of hardness?
Jason
Like are you saying like, how do you know there won’t be harder things beyond that? Like, how do you know it’s worth doing the hard things right now?
Advik
Yep, yep.
Jason
My answer is, you don’t know. I think that most answers are you don’t know. Actually you don’t know. There’s sort of this quest for certainty out there, and I think it’s a false search in most cases. Like everything’s a guess and a bet and a vibe and a feel, and you’re kind of like, just, I don’t know. It seems like I think this is going to be a good idea. And if it’s not, you move on and do something else. I’m not a big fan of like reflecting on was that the right decision or not? It was the decision that was made in the moment. And here’s another moment right ahead of you. So make a new one if you have to. So I don’t worry too much about like how do you know more broadly when someone asks like, how do you know I don’t know. I don’t know.
Derek Sivers
My old music teacher from Columbia College in Chicago said.
Jason
Oh my God, you went to Columbia in Chicago?
Derek Sivers
No, no, no. But I lived in Hinsdale and I drove in to meet with him. It was right before I went off to Boston, to Berklee College of Music, met this great music teacher that taught at Columbia. But I would drive into.
Jason
You’re not from Chicago area are you?
Derek Sivers
Yeah, I am. You didn’t know this?
Derek Sivers
I didn’t know this. Yeah, I grew up okay from 1976, I moved from California to Chicago to Hinsdale, Illinois. I lived in Hinsdale from 1976 until 1987, when I went off to Berklee School of Music. So I grew up in Hinsdale from age 5 to 17. Wow.
Jason
Yeah, I’m from Deerfield, if you know where that is.
Derek Sivers
All right, yes, I do.
Jason
Yeah. Okay. Anyway
Derek Sivers
So did you ever have the, you know, the more the wide open Chicago accent. Did you ever have that?
Jason
I probably did. I mean, I don’t know. I didn’t grow up in the city, so I grew up in the suburbs. Not quite as wide open, but people have said, “You have a Chicago accent.”
Jason
Those who know people from Chicago, but I don’t feel it.
Derek Sivers
Oh, I don’t think so.
Derek Sivers
Okay. What were we talking about?
Jason
Your music teacher in Hinsdale.
Derek Sivers
Oh, okay. Sorry. Yes. Yeah. So he’s living in West Virginia now. And he said that raising his daughter in Chicago did not turn out the way he had hoped. And I said, “Oh, so it was a bad decision?” And he said, “No, no, no, no, no.” He said, “Let’s not confuse those things.” He said, “My wife and I made the best decision we could at the time. We were thoughtful. We considered all the knowledge we had at the time. We made a decision.” He said, “I didn’t like the outcome.” He said, “But those are two different things. You can make a good decision even though it has a bad outcome. You can’t say it was a bad decision. But on the other hand, sometimes you can make a bad decision that’s whimsical, emotional, uneducated. That turns out good, but you can’t say it was a good decision, you were being stupid and you got lucky.” Even if you were being smart, it doesn’t always turn out the way you want. But sometimes when you were being stupid, it can turn out well. So it’s good to distinguish between a good decision and a good outcome.
Jason
I like that, I like that you can also kind of laugh at that. In a sense, it’s like it could be either or. And that’s to me how you know it’s good is it’s a little bit funny. It’s a little silly.
Derek Sivers
On that note, dude, last time I saw you in person, sitting next to me was a woman I had just married, even though I’d only known her a few months, which was me being stupid. And it really was objectively a bad decision because I was deliberately trying to scramble shit in my life. I was trying to do the opposite of whatever I used to do. And so whenever my instinct would say, turn left, I would turn right. If my instinct would say go, then I would stop. And so I met this woman in New York City. We were dating for a bit, hardly knew each other. And then she said that her family would insist that we were married in order for her to travel with me. And so everything in my instinct said, “Oh hell no, I’m not going to get married. I don’t know you.” So I went, “All right, yes, I will.” So I married her and it was a stupid decision and it also did not have a good outcome. But the last time I saw you. Yeah.
Jason
But here you are, you’re smiling right now.
Derek Sivers
Exactly. It’s laughable. It was stupid and it was fun. But, you know, in a way, I’d actually recommend if somebody wants to scramble up their life, I recommend this process. Just go against your instincts at every turn.
Jason
This is the time scale thing. So I bet you that was pretty horrific in the process.
Derek Sivers
Ten years ago. Yeah, yeah.
Jason
You seem like you’re doing pretty well. Things seem to be good for you. So, you know, it’s all time scale. Yeah, it could have gone south. It would have been south had you stayed in that relationship probably. That would have been second bad decision perhaps.
Derek Sivers
Yeah. You’d be seeing me, like, miserable with bags under my eyes, just looking like a sad sack. I’m going to totally change the subject. I’ve got a question for you. How much of what you do is fueled by anger or rebellion at the way things are?
Jason
Who are you asking?
Derek Sivers
You, Jason.
Jason
Okay. All right. I think a lot of it, actually. But I’m not angry. Like, I’m not angry, but I’m irritated at something. For example, we’re currently working on two new products right now. We’ve never done this before, working on two products simultaneously. And we’re going to try to launch them on the same day, which is going to be kind of a fun challenge. But this is born from-- I’m not going to talk about this products. But it’s born from-- I’m on an HOA so I live in a neighborhood. We have an HOA, homeowners association and I’m on the board now. I was drafted on the board here, and I was reviewing like some stuff that we have going on at the HOA. And there’s this piece of software that we use that’s terrible, that you use when you like, check in a guest so they can do a parking pass so they can park on the street, basically. And I knew the software was bad because I use it. But now that I’m on the board, I got to see like our budget and we’re spending $10,000 a year on this piece of software.
Derek Sivers
God.
Jason
And it just pissed me off so much. But I’m not angry. It’s more like it’s humorous. It’s like, are you kidding me? And what it really did to me actually, was it made me think two things. One was, there are so many small groups that are abused by the software industry. Like this HOA they didn’t know any better. How would they? They’re not going to go shop for this software. Some sales person came by and sold them this thing and they’re like, “Yeah, sure.” How would they know? And that feels like a form of abuse to me that really bugs me. The second thing is, more fundamentally, I don’t believe software should be expensive, period. There’s no reason for software to be expensive. Now, it’s expensive at the enterprise level because it can be, but not because it should be. It’s software, you write at once. I mean, you improve it, the whole thing. But, like, come on. So anyway, these two things about small groups being abused by the software industry, essentially, and software being too expensive. These two things fueled like a deep humorous anger, irritation in me to do something about it. And so these two things were not building those products. But these are products for smaller groups that will be affordable, will be really really good. And basically throw up their middle finger to like these other things that are so expensive and not really good. And so I love that edge. I need to be a bit angry about something, I think, to do a good job with it. But it’s interesting because I’m not an angry person. I’m not angry about it. I’m not screaming and yelling about it. It’s more like, this is an injustice, actually, is more what it feels like to me. And you kind of want to write that. So that’s what it is for me. I think we’ve always done that kind of in, you know, what about you? Are you that way at all or are you doing it out of the love of humanity?
Derek Sivers
I want to keep this on you a bit.
Jason
Okay.
Derek Sivers
It sounds like maybe you’ve got some negative associations around the idea of angry, and I didn’t mean it like because you can tell you’re not like a bitter person full of bile, but even when I think all the way back to the first time I was ever aware of you. Was that redesign of fedex.com, which must have been in 2000 or something, or 2002.
Jason
Probably. Yeah. Yeah.
Derek Sivers
And which I got the sense that you looked at this and was like, “No, no, this could be so much better. Why is this so hard?” And then I did see your blog post about the parking guest software, and you put a little screenshot of it and Jason looks at that and he goes, “No, no, God, this could be so much better.” And then the price. Yeah. So you were kind of double fueled, not just visually but price wise, that I think it seems to me from the outside that a lot of your motivation comes from looking at the way things are done wrong and that inspiring you to do them right.
Jason
Yeah, I wouldn’t even necessarily call it wrong. It’s just like looking at the way things are done and thinking that they could be done better. So I don’t actually even think it’s wrong. Some of it is, like the pricing is wrong and there’s some abuse. Some of the language I’m using perhaps does sound like it’s wrong, but it’s more like this is what it is. This is like this is the industry that we’re in and this is sort of how it runs. And I do think it’s wrong, I guess fundamentally, but it’s not about righting the wrong, even though that’s what the injustice thing is. It’s more about like presenting an alternative that’s just flat out better and surprisingly better and more affordable. I almost feel like just an obligation to let me--. Actually another fantasy I’ve had which is related to this, is it’d be neat to-- I guess this is what open source in some ways is kind of supposed to be, but it’s not quite this. Which is like it’d be cool to get to a place and we kind of are maybe beginning to do this a little bit where, you know, you’ve built a successful business, gotten a lot of money coming in, things are good. You’re taking care of whatever, you have enough the whole thing to, like, spend the last five years of your career just spinning out really good, simple, free things. So we just we just launched this thing called Writebook, which is part of the once thing, which is a free piece of software, totally free. You get the code. It’s like as free as free can be to publish your own books online. You get to host the thing. But it’s very simple. And it felt so good to put something out there that was so complicated and hard to do prior. Like to publish you-- I don’t know if you’ve you haven’t really published your books in this way necessarily. But if you write a digital book and you want to like put it online, like you got to like get WordPress and like make a custom thing or like you’ve got blogging software that’s not quite really for a book and you’ve got like different blog posts, but you got to have some navigation thing you got to futz with to try to make it like a book thing like this is just way too hard.
Jason
It’s so hard to just put a book, a collection of texts out there that’s self-contained. It’s one thing. And so we built this, we gave it away. And I would love to solve all these really vexing, long term, ignored problems with really simple solutions, with no obligations to either improve on them or anything because they’re free. But just like send them out into the world and be like, let’s just seed the world with just some really, really good, well considered free stuff that you’re on your own with. Now, that is kind of what in some ways open source is, but not really fundamentally. It’s not really about simplifying and improving stuff that’s complicated. It’s more about open source and contributions from other people and being able to see the source and making it your own way. The root thing about like presenting something that should be way easier, simpler, better is not part of that ethos necessarily. And so that’s what’s appealing to me. Again, I don’t know if we’d have the motivation ultimately to do that, but I think it’d be a neat thing to do. Anyway.
Derek Sivers
I love it. I think it comes from first feeling like you’ve satisfied your own needs, right? Your life is fulfilling. You’ve got enough money. You’re good. And now, because the Maslow’s pyramid of self-actualization, or pyramid of needs has been met, you can turn your attention to do things just because they should exist.
Derek Sivers
And, yeah, that’s always been the spirit that I tried to operate in. Even if I was, say, going through a hard time in my life and not feeling like all of my pyramid of needs were being met, sometimes even acting as if they are, gets me back into a place of feeling that they are. So always choosing to be deliberately generous with business, or with my time or with my work keeps reminding me that I have plenty, and it’s good to keep my attention focused on sharing and giving.
Jason
Yes.
Jason
That’s awesome. I know you’ve lived that because I’ve had some friends who have emailed you for your advice, because I think you basically say, email me and I’ll get back to you. And I know Derek, but I’m not going to connect you. You do your own thing. And they did. And you got back to them and they, they were very appreciative of that. So--
Derek Sivers
That’s a good example. It’s when people say, “Why do you have an open inbox?” Honestly, it’s one of my favorite hours of the day. I take about an hour, sometimes two hours, sometimes no hours. But let’s say an average of an hour a day averaged out over a week or a month, to my inbox. And it’s 99% positive. I’m not running a company, so people aren’t emailing me to complain, you know. It’s mostly just positive. Somebody that read my book and liked it, or heard an interview like this and emailed to say hello, and damn, I meet really interesting people. And then when I travel, I go meet them in person. So I just got back from this trip in South America, where I went and met up with 50 people, one on one that I had been emailing with for years and met them for the first time. And well, yeah when I go to Delhi someday, Advik and I will meet. We were just talking about that that I still haven’t been to Delhi really. But when I do, we will definitely meet up. And that’s what I love about the open inbox, is keeping the humanity very connected to it. It would make me really sad to just do what I do without any connection to the people that are affected by it, you know.
Jason
It’s great. It’s great that you’ve kept that up too.
Derek Sivers
But how do you do that? You’ve you’ve got way more customers than I do. How do you keep in touch with them or how do you keep your finger on the pulse?
Jason
One of the fortunate things about selling or putting software out there that people pay for is that they tell you what they think.
Derek Sivers
Okay,
Jason
So I think when you put something out there that’s free, it’s actually harder to get--. I find it to be harder to get feedback actually in a sense. But when you when you charge for things, people really tell you what they think. And so I get dozens of emails that hit my inbox a week from customers. And I get back to all of them. The hardest thing, though, is the longer the email, the harder it is to get back to someone, because I feel this deep obligation to sort of be commensurate with my time. And sometimes I don’t know how to write a long email like.
Derek Sivers
Yeah.
Jason
So those tend to sit actually, even though this person put a lot of time into it. So I always feel weird about the balance there about like they put a lot of time and now I’m taking too much time and we’re going to get back is not going to seem like it was worth the wait. So I do struggle with that. But you know, someone takes the time to write you, you should take the time to write them back. I mean, as much as you possibly can. Of course, if you can’t, you can’t. But I try, I definitely try. I mean, my email address is everywhere too. I don’t hide it. And I think it is important, although it is a struggle for me sometimes. I’m not quite--. I don’t know, I don’t know if I should call you extroverted or not. I don’t know you well enough, but I think you you’re probably both. I don’t know, you seem both to me.
Derek Sivers
Solitary socialite.
Jason
Yeah.
Derek Sivers
Sitting on an island in the Pacific. Sitting here in remote New Zealand. Social online. So it’s like my my physical life is antisocial. Or I just spend all my free time with my kid, and then my online life is social.
Jason
Amazing. That’s amazing. Yeah. So I don’t know. I do struggle with the balance there. But I do know that if I was to like stop doing that, something would feel like it was missing for sure. I’d feel very disconnected very quickly. And that’s not a good place to be as a business owner or a human in general. There’s enough people around that I know and keep in touch with personally, physically. But yeah, when you run a business, you gotta--. I’m always shocked by people say, like, “How do you find the time?” It’s like, how don’t you find the time? Isn’t that what you’re supposed to be doing?
Derek Sivers
Yeah. I think it’s just in the self-identity. So I’m not going to name names right now, but I know a few public people that have just made a decision early on like, “No, you can’t reach me. I don’t want anybody to reach me. Contact my manager, my agent, my assistant. Don’t contact me. Do not.” And that’s just who they want to be in the world. You know, it’s a little bit aloof. And that’s what they’re happy being. Yeah.
Jason
And also, you know maybe you know, this person you’re talking about or people. But like, they also might be if they’re extremely popular, they might get 10,000 letters a week. You know, it’s like there could be a place where literally isn’t possible, you know.
Derek Sivers
Yeah. True.
Jason
So who knows? But yeah. Hey, everyone should be themselves. And I get it. I get all of it. Get all of it. Yeah.
Derek Sivers
What was the thing you used to do, was it called Highrise? Where it’s just like you kind of manage all the people, you know. Yeah. Was that high rise?
Jason
Yeah, Highrise. And that’s a CRM. It’s like a more of a business thing, but yes. Like, who do you talk to when you need to follow up next. And what did they say and what did you say. Basically that was like the primary.
Derek Sivers
Right. So Highrise is gone now, right?
Jason
It still exists. So one of the things we do is we never turn off products. I shouldn’t say never. We’ve done it like once. If you’ve used our products in the past, you can use them forever. We don’t sell Highrise to new customers, but we still have thousands of people who use Highrise. We have thousands of people who use Todolist, which is like this thing we built in 2005, a simple to do list. Like that’s online too. We keep everything online. Unless we absolutely can’t. So it still exists. But not not for sale.
Derek Sivers
For what it’s worth, I don’t know if I should only be telling you this offline, but oh, well, here we are. I think that the Highrise should be considered as like your Writebook, something that’s just like, “Right the world needs this. Here you go.” Although I guess it’s tougher because you have management costs, but if it could be turned into something that-- it’s my number one request I get about, I’d say about five people a week independently asking, “What can I use to manage the people I know and track the conversations?” And I used to send everybody to Highrise, and now I say, “Well, there’s a couple other shitty solutions. I don’t know, maybe I’ll try to make my own someday.” But it’s the number one most requested thing I get.
Jason
It’s funny. It is the number one request we’ve had so far for a once style product. Because people don’t want to pay for that in perpetuity, right?
Jason
But they might pay for it once. And I’m kind of shocked, to be honest, because it feels like there’s like, contact books and basic stuff, but apparently there’s something that’s missing from that, that people like really crave. And I haven’t really put my finger on it because it’s elusively simple. It’s like there must be something barely better than what exists. And that would be everything to them, you know, versus like, gosh, how would you make this? One of the problems with like CRM tools is that what you’re talking about and what I have in my mind, it’s not CRM. I don’t need to manage pipelines, deals and sales. It’s not that. It’s not that. Right. There’s that but that’s not what we’re talking about. It’s like, who do I know? What have I said? What have I followed up like, gosh, I haven’t talked to this person for eight months. I should maybe check in with them or whatever. Right. That kind of real, real simple, basic thing. I think we’d have to probably do that and give it away for free, maybe. I don’t know, it doesn’t seem like, I don’t feel like-- I hate this word consumers. I’m going to use it, though, because I don’t know what else to use would pay for. But God, I hate that word.
Derek Sivers
Yeah.
Derek Sivers
I know what you mean, though. Yeah, it does feel like if somebody created it. Okay, so there is something right now called Monica. Monica is pretty damn good.
Jason
Don’t know it. Okay.
Derek Sivers
I believe it’s completely open source. You could self-host or pay him a dollar or something to host it for you.
Jason
Yeah.
Derek Sivers
So that’s what I’ve been sending people to. It skews a little much on the, like, separate data fields for the name of this person’s children and the birth dates and all of that kind of stuff. It does that more than I would like.
Jason
Yeah.
Derek Sivers
But it’s free and open. But then the other tools are a much more like, “Hey, pay us $20 a month to manage your contacts.” And it feels much more like businessy. And but yeah, it does feel like something quite simple should exist and everybody would be thankful for that.
Jason
I think so, so okay. We’ll see.
Derek Sivers
I can’t believe I just told you that publicly. Sorry. I didn’t mean to.
Jason
No. That’s great. Yeah. No, not at all.
Jason
All right.
Advik
What is the greatest email you guys have received?
Jason
Ever sent?
Derek Sivers
Received.
Jason
Oh, received.
Advik
Or recieved, both.
Jason
I had an email once where we had a customer early on. We used to make this thing called Backpack, which is like a kind of a super early version of, like, what people might think of as Notion today. Like a single page document organizing kind of thing. And this guy called us thieves and snakes, and I forget what it was because we raised the price by a dollar. And he just went off. We had to get a restraining order against this guy at some point, but the email was so vicious for a $1, like, send me a vicious email if like I really did something terrible. Please, I want to hear from you. But like, we raised the price by a dollar and it just was like--. And so that was like a classic, amazing, amazing email. The other one I’ll I’ll share, which actually drove me, inspired me for many, many, many, many years when I was first getting into web design. Derek, you might remember this. There’s this guy named David Siegel. He ran this award site.
Derek Sivers
Of course.
Jason
Yeah, I forget what it’s called. The award site was called but.
Derek Sivers
It’s not cool site of the day or was it something like that?
Jason
Something like that.
Derek Sivers
I remember David Siegel. Yes. And I heard him speak too. Yeah.
Jason
So I submitted a design to him because I was like an eager young web designer trying to, like, you know, get an award because everyone’s bio is like, “Award winning award winning.” Like, I guess I should have one of those. I’m not going to lie. So let me try to get one. And he wrote back, he’s like, “You suck. Your design sucks. You should get a new day job, basically.”
Derek Sivers
Wow.
Jason
And I loved it. I loved it, absolutely loved it. In the same way that I loved the first review we ever got for Rework. Our book Rework was a horrible negative review from like, Management Weekly or something. Like some traditional management magazine.
Derek Sivers
Nice.
Jason
And it panned the book. Just hardcore. I love that stuff. I love that put a chip on my shoulder, please. I love that kind of stuff.
Derek Sivers
I love that. Put a chip on my shoulder, please, I love that.
Jason
Yeah, I love that kind of stuff. So those are the emails. Those are the selection of styles of emails that I’ve received that really--. I just get a big grin on my face. I love it. I guess it stems from the fact, like I’m 5’7, I’m kind of a short guy and I could jump. So I used to play basketball pretty well and, like, would surprise people. Like, I could, like, dunk a tennis ball, like, in my prime. Not a whole ball, but a tennis ball. And so, like, I love this. Like, you can’t do that. I love this. Like, I’m not going to take you seriously. I love showing people up in that way. There’s something about me, must be some insecurity deep, deep inside. But it’s really fun for me to to get that kind of feedback. It fills me up. So anyway.
Derek Sivers
Nice. I wrote a book a few years ago called “How to Live”. It was deliberate.
Jason
Oh love that book.
Derek Sivers
Thank you. Deliberately set out. The whole point of the book was that every chapter is going to disagree with every chapter. That one chapter is going to say, “Here’s how to live. It’s all about you live for the future. Everything you do today is in service of the future.” And it’s supposed to be persuasive. And while you’re reading that chapter, you’re supposed to be persuaded that this is the way to live. And then the very next chapter says, “Here’s how to live. Be entirely present. There is no future. There is no past. All you have is now.” So every chapter is supposed to contradict. And it says right there in the title “How to Live. 27 conflicting answers and one weird conclusion.” That’s the title of the book. The top review on Amazon was one star saying, “This is bullshit. The first two chapters are already disagreeing with each other. I’m stopping reading this now. This is the worst book I’ve ever read. He’s already disagreeing with himself by chapter two.” And that for some reason, that review stayed wonderfully voted high. And I just got this wonderfully smug. It just makes me so happy to see that review. I don’t know why. Maybe it’s like the hipster, like, “Yeah, you don’t get it. Look how cool I am.” Maybe it’s that you know, it’s art if some people don’t understand it, right? If everybody understood it, it would no longer be art. Maybe that’s it, I don’t know.
Jason
So can I ask you something about that book? I thought that book, I thought the concept first of all, the writing is great, obviously, but the concept was so good. Are you ever disappointed that more people don’t know about that book or that idea? It feels like such a-- how do you feel about that kind of stuff?
Derek Sivers
I make that trade off kind of like we talked about earlier with not being a public company. My very first book was on Penguin and they were nice. My main contact there was really nice and she said, “Hey, anything you publish in the future, we want it. We just we love working with you. We’re happy to work with you. Whatever you got, give it to us. We’ll be happy to publish it.” And I said, “Thanks, but no, I really just like self-publishing better.” I like not answering to anybody else. I like owning my copyrights fully so that if somebody in Albania wants to translate the book into Albanian, I can say, “Sure.” I don’t have to say sorry, you got to go ask Penguin. So I knew that it was a trade off. I knew that I would sell thousands instead of millions, and that’s fine with me because I write these books really, just more for my existing fans. I’m not trying to be, you know, the next Mark Manson or something, even though he’s a friend and I admire him. I don’t want that level of fame. I’m really happy with this little level here. So, and then “How to Live” in particular if nobody on Earth bought that book, if everybody on Earth hated that book and nobody got it, nobody understood it, I still would have been equally pleased. That book, to me feels like the best book ever written. And if I did nothing else with my life than make that book, I’d feel like that was a life well lived. Like, I’m so fucking happy I made that book. I don’t care if anybody else likes it or not.
Jason
That’s a great attitude, obviously. I mean that that’s wonderful and you should feel really proud of that. It’s a great idea and well executed. And ultimately that is what you have to be, is proud of your own work. That has to be it.
Derek Sivers
I can maybe imagine what you’re going to say, but since you and I have been online. An interesting thing has-- the pendulum has swung two ways. Think of the music business. Oh wait, by the way, I’m sorry. I’m going to come right back to this point. I have a cute answer to the best email I ever received. Nobody’s ever asked me that. You made me think about it for a second. 1997, “Hi, my name is Sarah, a happy girl from Sweden. You sound really interesting. Please tell me more about yourself.” And I looked at this email and I thought, “Is this is this spam?” Like, I don’t it sounds like, you know and click here for hot sex. I was like, “I don’t know if this is spam or not.” So I was like, “Who are you and why do you think I’m interesting?” Send. And the next day she replied back like, “Oh well, I was just browsing the web and I found your site. You just sound like a cool person.” And I replied back, like going, “What were you searching for that you found my site?” And she replied back. This ended up going on for six months that we would trade one email a day until we met. Fell in love. Years later, got married. Stayed together for six and a half years. Because of that little initial email.
Jason
Wow.
Derek Sivers
I think that’s the best email I have ever received. She was great. Even though we broke up, it was a great relationship. Not every great relationship needs to last forever. It was a good one anyway.
Derek Sivers
I started to say you and I have been online since mid 90s.
Advik
Yeah. Yeah.
Derek Sivers
The music industry before MP3’s was like you had to sell your soul to please the man at the record label. Only if you pleased the man could you be allowed through the gates to reach the public. And then, like 1999, 2000, there was this indie music revolution with MP3’s where it’s like, “Hey, we don’t need the man anymore. We can go directly to the fans.” And it just fueled this revolution in the music industry. That’s no need to sign your rights away. No need to sign your life away. You can go directly to the public. But then I feel like the pendulum has swung back where every author is trying to kiss Amazon’s ass, and every creator of anything is trying to kiss the algorithm’s ass. Trying to make the man happy, trying to post at the at the pace that the man wants me to post at. Well, they say that I have to have a thumbnail on YouTube with my mouth open. And if I do that, I’ll get more clicks because that’s what the man wants me to do. Got to keep the man happy. I feel like like something’s gone really wrong in this. I feel like they forgot the revolution. They forgot what we were rebelling against and are now choosing it even though they don’t have to. Whereas before we had to please the man.
Jason
Super interesting. It’s almost like YouTube, for example, is a record label that doesn’t have to sign anybody, but everyone’s working for them.
Derek Sivers
Yes.
Jason
Yeah, yeah. It is interesting how that has happened. And it seems like there’s no stopping that at the moment. I wonder how that will stop. Like, will people throw up their arms and go, “I’m not doing this anymore.” I just have a hard time with it because now these things have become business. I think the other part actually, is that when you and I started, it was more of a hobby. The web was a hobbyist thing. It’s like, what the hell is this thing? No one knew. Now it’s a business, now it’s an asset. Now it’s it’s about money. And that’s typically what happens. And there’s nothing wrong with that inherently, really. It’s just that’s what it’s become. And there’s not the hobbyist alternative anymore really. And I just don’t find that to be the case anymore. Yeah, I don’t know.
Derek Sivers
Okay.
Jason
I don’t know. It just feels like the-- I’m probably thinking. I mean, this is probably common, though, in all sorts of all sorts of mediums where it’s an insider thing, a small underground thing becomes a mainstream thing, then becomes a business thing. And it’s just like, of course, it’s not like it used to be, you know?
Derek Sivers
Right.
Jason
Like farming is probably the same thing, right? Like, I don’t know, all these things probably are very similar to that. I think it’s just probably, it’s the pattern. It’s like evolution doesn’t really go backwards.
Derek Sivers
Right.
Jason
As far as I know. I don’t know, maybe it has.
Derek Sivers
But things do get reset sometimes. Like even what I was talking about in the late 90s, I’m sure that there might have been a 1960s version of that. And then things like kind of grew and grew and grew in the 70s and 80s and 90s and then MP3’s brought it tumbling down.
Jason
Yeah.
Derek Sivers
And then it grew again.
Jason
I think you’re right. But is it usually a new medium/platform where that rebirth happens? Also, nostalgia is not durable. So like we could be nostalgic for the 90s, but that’s not going to make the 90s come back or stick around. The ethos of that is just that was stuck. That was in the 90s. That happened then, kind of like, you know, full circle about what we’re talking about earlier. Like some things happened in the past and that’s where they are. They don’t get to come back. I had this remarkable-- this is a weird tangent, but I’ve done, like, high doses of mushrooms a few times in my life. And I had a really profound experience last few months when I did this. Where I’d wanted to re-live an experience I had the first time I’d done mushrooms. And I was, like, trying to re-live this experience. And I asked the guide who I was doing this with to play the same song that played the first time. That really gave me this incredible experience. I had just this profound, deep experience from the song. Which was in the time of Cholera, I believe, is the name of the song from the movie, I think. But it was the song. Anyway, and so I’m like, “Can you play that again? Like, at some point in this journey, if you feel like, you know, play it again.”
Jason
She played it again and it was absolutely dead to me. And I had this beautiful insight in the moment, which is like, you know what? You don’t get to have the same experience again. You don’t get to even decide what experiences you’re going to have. And it was so light and liberating, actually, even though I wanted this thing so bad, I wanted to re-live that one moment so bad. When it didn’t happen and it was like the emptiest moment of all the moments I had. I had wonderful moments in this experience, but that one was just at the bottom. Not like in a bad way, just in an empty way. Nothing happened. It was such a revelation for me. Like, you just don’t get to have the same experience again. And so that that stuck with me. I mean, it’s only been a few months, but it really stuck with me in a variety of other ways, and I’m going to bring it here and serve it up here in a sense that, like, we don’t get to have that again, those those 90s moments when we were hobbyists and this was happening or early 2000s. We don’t get to do that again. That was that, the next thing will have to be a different thing. It cannot be the same thing again. So anyway, that’s my little---.
Derek Sivers
Nice. I like that it’s I wonder, did that song by Chance feel surprising when you heard it the first time?
Jason
I’d never heard it before.
Derek Sivers
Oh, okay.
Jason
I’d never heard the song before the first time. And then I heard it. I didn’t know what it was. I had this really deep, profound experience while listening to it. And I remember at the end crying, just saying thank you for that. I didn’t know what I meant, and I said, “What was that?” And she wrote it down for me. And then this third journey I was on, I was waiting for her to play it because I asked her to play it and, like, “Play it if you think it’s the right thing.” But I kept like, every time a new song, “Is it gonna be that one?” Now, of course, at some point I was gone and I couldn’t think about what was coming next. But every once in a while I’d come to, in a sense, and like, wonder if that was going to be the next song and then when it finally was huge letdown, but not in a negative way. It was like this--.
Derek Sivers
Right, you had this epiphany.
Jason
The profundity of the experience was better because it was a letdown. It was like a realization that you could only have by being let down that, “Oh, you know what? I don’t get to have that again. I don’t get to choose that.” So anyway, I’m just going to leave that there because whenever I come back and I do come back, there’s nostalgia. And you want to remember when. And yeah, you don’t get to do that again. That was that. Which is beautiful because you get to really-- to me, it helps me pay more attention to the present. It’s like this experience I’m having right now, like I’m having with my kids. My kids are nine and five. I’m like, I can already see my nine year old and my nine year old’s like almost ten. It’s like ten is different than five. His sister’s five. Like I’m only going to have a few more years of this like sort of tender young child thing. I don’t get to have that again. Now I could have another kid. I’m not going to do that. We’re not going to do that. But like, this is it. So it’s sort of this really wonderful moment to really enjoy that and pay more attention to the present actually than think that this could ever happen again.
Derek Sivers
I like that.
Jason
Yeah.
Derek Sivers
You know, what’s funny, our kids will ask like, “Hey, I like that thing. Can we go do that thing again?” And sometimes the answer might be, “Actually, you know what? No what you liked about it was that you had never done it before,.” There are some things that deserve to be turned into a ritual, but you might need to share this with them too.
Derek Sivers
I took my boy to Japan once. He liked it so much that the next year he said, “Can we please go back to Japan again?” I said, “Oh, come on, there’s a big world out there.” He’s like, “Please, please, please, please, please that was amazing. I still want to go to Japan.” And you can guess where this is going. We went back to Japan to the same places that he loved last time, and the charm had worn off. Because what was exciting was that it was the first time. And actually, it turns out the other thing that was exciting was the time we went. Last time we went was literally the day that Japan opened after a few years of being closed for Covid, they announced on October 11th, “Okay, we’re allowing tourists to come now.” And we booked a flight that night and went there on the 12th. And so everywhere we went, there were no tourists at all. So we went back one year later to those same places and it was all filled with tourists. It was like, “Oh, I liked it last year.”
Jason
Of course.
Derek Sivers
But stand up comedy. The point of a good joke is it’s a surprise. The comedian takes it to a place you weren’t expecting, and that’s why you burst out laughing, “He said what? He said what?” And if you try to listen to it again, it’s a little funny, but not as funny.
Jason
That’s a great insight, actually. Like jokes are never quite as funny the second time around. Same words, same delivery, perhaps even. But you know
Advik
Doesn’t it like, die down slowly. It’s not like from one extreme to the other extreme. It’s like it slowly loses--.
Jason
Right.
Jason
It’s not not funny instantly. It’s still funny, but like, you can’t reach that high again. It’s probably like addiction. Like you can’t get there anymore. So people chase that.
Derek Sivers
Right.
Derek Sivers
Beacause it was a surprise.
Jason
Yeah. The surprise.
Derek Sivers
That’s why I asked if the song the first time you heard it was surprising. It made me think about that. Like what was so magical in that first moment was like, “Whoa, what is this?” And it was that moment of being hit with it for the first time. And there was a music piece by Debussy called Sonata for viola, flute and harp. And a friend in Boston took me to a concert randomly. She said, “I’ve got tickets to this thing. Come with me.” Okay, I went with her. This piece starts and there’s a point where the flute plays a note, you know, like woo. And then the violin comes in and the violin takes it over while the flute fades out. And the very first time I ever heard it, I didn’t notice that transition happen. And so suddenly, the violin was playing what the flute was playing.
Derek Sivers
I was like, “Whoa, whoa whoa whoa. What? When did that happen? Oh my God, that’s amazing.” So I went and found that piece. And although I still love this piece of music. That moment will never again be a surprise to me. I always know now that the violin is going to come in and take over that flute part, so I will never have that magic of that first time.
Jason
You know? So okay, I’m going to bring this back to business. Even though I’m ruining it by doing this, I’m completely ruining it.
Jason
But I’m sure. Derek, you’ve been asked this a million times. Like, “Well, if you knew what you knew now, what would you tell yourself when you were 20?” And it’s like nothing.
Derek Sivers
Yep.
Jason
I don’t want to know what I know now when I’m 20. I want to experience those things because knowing it, first of all, you’re not ready for it. Second of all, like you can’t. And third of all, like I need to go through that. That’s the beauty is like the first time experience is the naivete is wonderful. It’s so valuable to be ignorant about what’s going to happen and how things are going to be and what’s going to hit you in the face and what’s going to kick you in the ass and what’s going to boost you up and who knows. But to feel like you’d be better off if you knew everything ahead of time. You’d be worse off every time, probably. Unless there’s, like, a disaster. Like, don’t do that because you will die because the thing is going to whatever. Like different story. Right? But if it’s not that. You’ll be worse off by knowing ahead of time. And people seem to crave this, I want to know ahead of time really there’s a comfort to that. But it really robs you of that surprise, which is really a beautiful thing. Yeah.
Derek Sivers
Don’t worry. You enhanced it. You didn’t wreck it. And that wasn’t just business. That was life. What should I know about making a great relationship? Well, you’re going to have to go through that the two of you together. You could apply that to a lot of things. Yeah.
Jason
So Advik you’re what, are you, 17 or something? How old are you again?
Advik
I like to turn 16 on the 9th?
Jason
You’re 16. So like, dude. Incredible, right?
Derek Sivers
I didn’t know that. Yeah, dude well,
Jason
So don’t listen to anything we’re saying because we’re ruining all these things for you.
Derek Sivers
Poor Advik. It’s ruined now, he knows too much.
Jason
Yeah. Anyway.
Derek Sivers
You know the scene in the matrix of just like, “Whoa, I know Kung Fu now. You know anything that can be learned is, like, attached to your brain. Yeah.
Advik
So how do you give advice? Go ahead. Go ahead. Go ahead.
Derek Sivers
How funny would it be if-- because we’ve set up such a funny. I’m sorry if it seems like I just won’t stop laughing about this, but we’ve set up such a funny social situation here where, like, Advik worked so hard for so many years to make this phone call happen. And then he’s just kind of like, sitting back and observing. And at one point I like, had to look down at the screen. I was like, “Wait, let me make sure he’s awake because it’s like, I know now it’s like 3:30 or 4 in the morning.” How funny would that be if he, like, at some point fell asleep.
Jason
Yeah.
Advik
It’s not that boring.
Jason
Well, so, you know, I have about 13 minutes left. I would love to go for hours truly. But I have 13 minutes left. I have something else I have to do.
Derek Sivers
All right. Advik what’s the last point you want to hit?
Advik
One question that I like to end with always. I mean, like, into all these things, like thinking about stuff and coding and into startups and all these things at like 11. What do you think is one fact that will blow 11 year old me mind?
Jason
What’s one fact that 11 year old-- I missed the end of that.
Advik
One fact that will blow 11 year old me’s mind.
Jason
11 year old you. Fun fact.
Derek Sivers
Maybe it’s just like, I guess. What’s the most surprising, counterintuitive thing we learned in life doing what we’re doing. Do you think, is that another version of the same question?
Advik
Anything, I have received a lot of tangential answers to this, like blueberries and fruit or something like that and all kinds of things.
Jason
Puberty. When you’re 11, you don’t know. I’m thinking about you don’t know what’s coming.
Derek Sivers
Aha.
Jason
Is that right? You said 11, right? 11 was the number.
Advik
Yep. Yep.
Jason
Your life’s about to change, man. Like 11 is sort of-- I can imagine 11 through 13 must be or 10 through 13 must be very interesting. I mean, it’s been so long since I’ve been there, but like, gosh to see that.
Derek Sivers
You’re in the middle of it right now. I mean, you’ve got an 11 year old. I’ve got a 12 year old.
Jason
Yeah, I’ve got a ten year old. So a couple more years.
Derek Sivers
Oh, ten. Okay. Yeah.
Jason
You’re right, you’re right there then. Almost.
Derek Sivers
God, I don’t, you know, with YouTube and the exposure to all the thoughts of the world. Sorry I’m saying YouTube in particular, because I’m thinking what an 11 year old would find more interesting than say, you know, books in a library right now. I guess YouTube has a lot of what books have. So I don’t know if there’s as many surprises as there used to be. All right. Jason went for puberty. I’ll go for a variation. Jason, I sometimes think about how we are a product of our culture without realizing it. Earlier when we were talking about the kissing the algorithm’s ass, I was thinking about how you and I grew up in a time when it was normal to talk about not being a sellout. Do you remember when to be a sellout was a common insult. And there was even that popular movie, Reality Bites, where it’s like three of them. And then there was this one guy that was a sellout, and they were all just like, “Dude, no respect at all. You can’t even be seen with us. You’re a sellout.” And then slowly the culture shifted, and I wonder how much hip hop had to do with that. The popularity of hip hop made it cool to be a sellout, and like, strongly emphasized how cool it is. Let me brag about what a sellout I am, but not using that word. Let me let me brag about how I’m doing everything for the money, make every decision for the big money.
Derek Sivers
And then slowly I feel the culture stopped thinking in terms of sellout. So that’s, you know, another thought around that. This is all circling back. I grew up at a time when the popular comedies, the main hit movie comedies, were often abou boys that wanted sex and girls that didn’t. And it was always like the horny teenager boy always wants sex, and the girls are just like, “Oh God, those boys, they talk about nothing but sex.” And so I watched these movies at a formative time that for decades, and I’m talking all the way from like, age, I don’t know, 12 until fucking 42. I thought that women didn’t like sex, that sex was only something that boys wanted, and that’s that. And I was 42 years old when I started dating someone. That changed my mind on that. And I was like, “Oh my God, I can’t believe what an idiot I’ve been for like 30 something years.” Thinking that, like sex is something that women don’t want and I think was one of the biggest, oh my God, mind blowers in my life. Like, that’s one of the few-- like, I wish I could go back and tell my 14 year old self, that’s maybe one of the only things that I think would have made my life a lot better to have somehow known that, you know, disregard these movies. They’re just being funny. It isn’t true. My life would have been a lot different. I had like almost like no sex from 13 to 42.
Jason
There were like John Hughes movies probably to, like Chicago area movies probably.
Derek Sivers
Yeah. Yeah exactly. John Hughes were definitely our hood right. Yeah.
Jason
It’s funny that reflect on those movies. Yeah.
Derek Sivers
And it’s funny how they invisibly influence the whole way you see the world. You know, like that’s where I just slowly started realizing this concept about the sellout going, “Oh God, that’s just not a thing anymore, isn’t it? Or is it like the nobody gets criticized for being a sellout. Now it’s cool to be a sellout, huh?” That’s interesting that slowly happened. Which then makes me realize I was just a product of a certain time in history.
Jason
Yeah.
Derek Sivers
If we were going on much longer. Jason, I’d want to ask you about, like being Jewish. Like, even if you’re not religious. But like being in, like, a Jewish family and the cultural values that are handed down invisibly like that, too. I had a weird experience where in Argentina, just a few weeks ago, I met a dude that I just extraordinarily clicked with. Like, we just had so much to talk about and like, instantly felt like he was an old best friend. And after two hours of talking, as we were saying goodbye, he said something about being Jewish. I went, “Wait, wait, what? You’re Jewish.” And he said, “Yeah.” I went, “Oh wow, no wonder we clicked so well.” Like, for most of my life, all my best friends have been Jewish. I don’t know why I’m not, but all my best friends are. And I wonder what is that, that makes me click with my Jewish friends so well. I get too analytical, wondering why, but yeah different subject.
Jason
Well, take that up on another another call at some point.
Derek Sivers
When we’re camping someday.
Jason
Yeah, I like that. Yeah.
Advik
Anyway, thank you so much for taking the time out for this.
Derek Sivers
Hope we could help you sleep.
Advik
Thank you guys.
Derek Sivers
We could entertain your insomnia, Advik was up all night. Glad we could, you know, make that a little worse.
Advik
For sure. Anything else you’d like you guys like to end with?
Jason
I mean, I think we’ve we’ve said it all and nothing at the same time. It’s been wonderful.
Derek Sivers
I’ll end with dude, thank you so much for all of the patience and the emails to so much scheduling to finally make this thing happen. It was a really, really fun conversation. So thank you.
Advik
I’m glad.
Jason
Yeah, I’ll echo that. Thanks.