David Senra: I want to start with what you told me last night, that you feel the best way to make a product or the best way to make a product for you is by you are the actual customer. You are making the products that you want to use.

Jason Fried: Yeah, I don't know how to do it any other way. Like, this is how I've always done it. So back when I was 15, 16, I started in software, making stuff, actually something called FileMaker Pro, which is way back when, where you can make these databases for yourself. And I made this database to keep track of my music collection because I was loaning out tapes and CDs to friends and never getting them back. So I'm like, I need a way to keep track of this stuff, because I keep losing these things. So, I made this product, which I eventually called AudioFile, but I made it for myself. It was just this database, right?

Jason Fried: And I made a nice interface, because I liked art, I liked making stuff, and so I made this thing, and I eventually just decided that I'll put a little text file in this archive of the software that said, "If you like this, send me 20 bucks." And I put it up on AOL, so this is pre-internet, right? Put it up on AOL, and I got this envelope, actually an airmail envelope, one of those with the red and blue check marks, old-school envelope, and it's from Germany.

Jason Fried: And I open it up, and somebody printed out this piece of paper, which was the thing I included with the software, and gave me a 20-dollar crisp US bill, right? And that was the moment I think it all clicked for me, which is make stuff for yourself. There's probably other people out there like you who want what you want and make it available to sell. So you are the customer, you are the audience. It's you, you, you, and then there'll be other people just like you.

Jason Fried: We're not all that unique. There's plenty of people who like what we like, plenty of people who don't, and there's plenty of products for them, too. But there's enough that like what you like, and so that's where I got started.

David Senra: Yeah, you have this interesting idea where if you're just making what you want, right? Doesn't matter. You just have to go and collect more people that like the things that you like and kind of ignore the people that don't.

Jason Fried: Yes, and this is all tied into keeping your costs low. So, if you have a lot of costs, high costs, big company, you have to find a lot of people like you. But if you keep your costs low, keep your company small, at the time, it was just me when I was doing the software thing. And I was making, I don't know, 20 grand a year selling software as a solo person when I was 16 years old or something like that, or 17, then I went into college a little bit as well.

Jason Fried: And it's like, that's an amazing little small side business, a huge side business when you're that age, right? Because I had no expenses. And so, it's easy. I only had to find a few thousand people to pay me that money, 20 bucks to get that eventually. But if I had a big business and had a lot of people, a lot of overhead, I'd have to find a lot of people like me, and that's harder. So, the whole game for me is to make things as simple as possible, as easy for me as possible.

Jason Fried: So, keep your costs low, keep your company as small as you possibly can, and make great stuff. And then you don't have to find as many people just like you, but the ones you find really love what you do. And that's like, that's enough. That is enough. You can stop there, keep doing stuff, but you can kind of stop there conceptually and go, I'm going to make stuff for me, people like me. I don't need the whole world to like what I like. I need enough of a small world to like what I like, and we're golden.

David Senra: You put it in a very interesting way. You said your real competition is your costs.

Jason Fried: Yeah.

David Senra: Is that the line that you have?

Jason Fried: Yeah. It's your only competition.

David Senra: Explain that.

Jason Fried: Well, a business is very simple. You've got to make more than you spend. That's a business, basically. I mean, you can keep borrowing money, and then you can borrow more than you spend, and eventually, you got to make more than you spend. So if you're making more than you spend, then your competition is your cost. And that's what you're really in business against, is how much it costs you to stay in business. It's not all the other alternatives that are on the market. Of course they exist, and they're real, but you can't do anything about them. They're going to do what they're going to do. You're going to do what you're going to do.

Jason Fried: You can't control what they're going to put out there, what they're going to price it at, all the things they're going to do. They're going to do what they're going to do. What I can control is how much it costs me to run my business, how much I sell my product for, and as long as I make more than I spend, I get to stay in business. And isn't that what this is all about, staying in business? Like, that's what it's all about, because I like this. We like this. I want to keep doing this. I can't keep doing it if I don't stay in business. I can't keep doing it if I make less than it costs me to make the things that I make.

Jason Fried: So, I'm always thinking about the only competition I really have on an annual basis, is to make sure that we make more as a company than it costs us to run the company. That's my real competition.

David Senra: And this is something I talk about over and over again with my other podcast founders, where it's just like, it is kind of weird how every single one of history's greatest entrepreneurs, they were obsessed about watching their costs, from Sam Walton to even Steve Jobs when he first started Apple.

Jason Fried: Yeah.

David Senra: Andrew Carnegie, Rockefeller. Like, this theme reappears over and over and over again. It's one of the reasons why my main partner is Ramp, because they want to help companies control their costs.

Jason Fried: For sure.

David Senra: It's like the perfect alignment for the audience and what these history's greatest entrepreneurs are saying. But we were talking the other day, where it seems very fascinating how you can have a software company that has insane margins and still lose money.

Jason Fried: Yeah.

David Senra: And when I talk to these young founders, I'm like, "Just go study the early days of Microsoft."

Jason Fried: Yeah.

David Senra: It's like Bill Gates. One of the most interesting stories was that the first 30, it's probably the most successful, arguably the most successful software company of all time, the first software company to get to a billion dollars in sales of just pure software in a year.

Jason Fried: Mm-hmm.

Jason Fried: Yep.

David Senra: But the first 30 employees of Microsoft were Bill Gates, his secretary, and 28 programmers.

Jason Fried: Yeah, amazing. And there is no fat.

David Senra: There was no fat at all.

Jason Fried: No fat.

David Senra: Yeah.

Jason Fried: All product.

David Senra: That's something you talk about a lot.

Jason Fried: Yeah. Yeah.

David Senra: Can you talk about the importance of keeping costs low, small teams, and then you want essentially no fat anywhere?

Jason Fried: We had 62 people at 37signals, and we've gotten as high as, I think, 80 at some point, and then we're about 63 or 62 right now, which feels really good. But we also built a lot of things when we were much smaller. We had 12 people way back in the day, or 4 people way back in the way, way, way days when we started out. So I've always been comfortable with small teams. I think that small teams work better, are better.

Jason Fried: There's less room for miscommunication, because I don't think companies really have communication problems. They have miscommunication problems. Like, when you have too many people and too many layers, and someone misses this, and someone has to repeat something that happened... I want to avoid all of that and get rid of all the things that get in the way of making good stuff.

Jason Fried: And I actually think too many people get in the way oftentimes, and you actually end up making worse stuff the more people who are involved. So, we just try to keep the team small. Any team we have making something is usually two people, like two people are working on a feature, one programmer, one designer. That's pretty much it.

Jason Fried: Sometimes someone else will come in here and there, but for the most part, it's two people. And it also keeps us honest. It prevents us from making things that we can't make with two people. So it just keeps everything tight and simple and clear. And you just keep parlaying that, keep adding that stuff up, and you end up with a very tight product with a small surface area. You can see the whole thing, you can hold the whole thing, you know how it all works. Your customers can see the whole thing and hold the whole thing and know how it works, and that's all people want. People don't want complicated stuff.

Jason Fried: They don't want software that's full of things they don't use. People will sometimes buy things like that because they're sold things like that, but when it really comes down to it, that's not what they actually want. And people who buy our software are the people who use the product. A lot of enterprise companies sell software to a buyer who then makes other people use the product, and everyone hates those products. But people who use our products buy our products, and it's the same person, so they're looking for stuff that just works really well. And I've just found there's no better way to do that than to keep the company small and tight.

Jason Fried: And that goes everywhere. Like, we don't have any middle management. We tried a little bit. That's why we had 83 people at one point. We hired a few more people to build out a little bit of a team and then pulled back from that and go, "That wasn't helpful."

David Senra: What did you not like about that?

Jason Fried: But there's two people on the executive team, me and David, my business partner. That's it. We've had a COO for a while. They were fine. They were good people. There was enough work for them, frankly, to do the work, so they just doing things that they didn't need to really do. And then when you do stuff you don't really need to do, you feel bad for them in a sense, because they're wasting their professional life doing things they don't really want to do, that doesn't need to get done. So that doesn't feel good.

Jason Fried: We've had engineering managers, and we found out again that there was too many levels in between David, who's the CTO, and the people doing the work. He had to talk to someone else, who talked to someone else, and it's like a game of telephone. Things are lost in translation along the way. We tried those things. We had some thoughts that maybe this would be a better thing for us to do, and it turned out not to be a better thing to do.

David Senra: How long does it take you to realize?

Jason Fried: A year.

David Senra: Okay.

Jason Fried: Basically. COO roles were longer. They were three years. We tried it twice. For the most part, we give everybody about a year to prove themselves at 37signals. And so we hire somebody, and they have about a year until we decide if we're going to hire them again. That's how I think of the second year. It's a rehire. It's not like a performance review, where we look at numbers. It's like one simple question. If I can, I always try to boil everything down to a question that answers all the other questions.

Jason Fried: So the question we ask after the first year with any new employee is, knowing what I know now, would I hire them again? And that answers pretty much every question. Answers every question about performance, about attitude, culture fit, all the stuff. If I know what I know now, would I hire them again?

Jason Fried: And so, it turned out with the management stuff, we're like, it wasn't even about the people. It was more like, now that we know what we know now, would we create this position again? And the answer was no. So we eliminated those positions and never rehired for them. So that's how we kind of got back a little bit to a smaller size.

David Senra: Does that work with products too, or features of products?

Jason Fried: It can. It's harder.

David Senra: You've rolled back people.

Jason Fried: Yes.

David Senra: You've rolled back entire products.

Jason Fried: Yes.

David Senra: Do you ever roll back features?

Jason Fried: We have done that in some ways. Typically, so every five, six years, we kind of reinvent Basecamp, which is our main product, our biggest product.

David Senra: Do you write it from scratch?

Jason Fried: We have in the past. So, from Basecamp 1 to Basecamp 2 was a total rewrite. From 2 to 3 was a total rewrite. From 3 to 4 was not, and 4 to 5, which we're working on now, is not. But it's a chance to revisit a lot of fundamental assumptions about what the product does and how it works. I'm trying to buck the trend, right? The human nature is about expansion, typically. Like, things tend to expand. But in the physical world, there's also limits that push back on those expansions.

Jason Fried: Like, if this mug was burning hot, we would know that's a bad design. If this handle, if there's no handle here, and I had to hold it this way, maybe not a good mug. Like, there's physics here. You look at this. If this thing was made of a really, really fragile material or something that would melt if it got wet, you'd be like, "That's a bad design." There's some things that are telling you this is a bad design. In software, you don't get that.

Jason Fried: Software can be anything. It's infinitely malleable. And what ends up happening is because there's nothing pushing back, it just expands forever and gets worse. Software slides downhill. It gets better for a while, then slides downhill. So, I'm conscious of that, and I'm always trying to make sure that every new version we make of something is a little bit simpler in the fundamental ways than the previous version. It might have more features, but the experience hopefully is simpler.

Jason Fried: That's the big challenge, and actually, frankly, the most fun part of building products over the long term is, can we buck the trend of having them slide downhill and instead maintain or make them even better over time?

David Senra: Why is that fun?

Jason Fried: It's hard, and that's fun. It's a bit of a puzzle. It's a bit of pushing back against the forces of nature, typically, which again, would be to expand. It's forcing us to come up with clever solutions to problems, more creative solutions to problems. It forces me to understand what something really is and not what it could be or what I think other people think of it as, but like, what is this really trying to do? And it's fun to have these insights.

Jason Fried: So my favorite thing in life, frankly, is to have an insight. And I don't get to decide when I have them, right? No one does. You just have one, right? Maybe it's in the shower, maybe it's whatever. You just have an insight. And it's cool to work on a problem in software and then have an insight about how to make it simpler. And I find that, for me, for whatever reason, I bounce into those insights very frequently, making software, more so than pretty much anything else I do.

Jason Fried: So, it's fun to make something new because I get to have more insights into how to make it simpler and better. And that's just like, for whatever reason, that's where they come from, the shower and the software.

David Senra: A lot of the conversations that Jason and I have are about craft, about the importance of putting your soul into your work and making the best possible product that you can. Our conversations remind me a lot of the conversations I have with my friend Karim, who's the co-founder and CTO of Ramp. Ramp is the presenting sponsor of this podcast, and Karim is one of the greatest technical minds working in finance today. Karim is obsessed with crafting a high-quality product and using the latest technology to constantly create better experiences for his customers.

David Senra: Ramp has one of the most talented technical teams in finance, and they use rapid, relentless iteration to make their product better every day. In the last year, Ramp has shipped over 300 new features. Ramp is completely committed to using AI to make a better experience for their customers and automate as much of your business's finances as possible.

David Senra: In fact, Karim just wrote this: "AI is all I think about these days. It is our duty to be first movers and push limits so we can make the greatest possible product experience for our customers." Many of the fastest-growing and most innovative companies in the world are running their business on Ramp. Make sure you go to ramp.com to learn how they can help your business save time and money. Let AI chase your receipts and close your books so you can use your time and energy building great things for your customers. Get started today by going to ramp.com.

David Senra: We were talking a lot about this conversation I just had with Tobi Lütke. I know both you and I admire him.

Jason Fried: Oh, yeah.

David Senra: And what I love about Tobi, that you have in you as well, is when you talk to him, the next response out of his mouth is not predictable.

Jason Fried: Yeah.

David Senra: And some of his views are not correlated with one another, which also makes it really interesting.

Jason Fried: Yeah.

David Senra: So, for example, you've been running your company. You started your company when you were 25.

Jason Fried: Yeah.

David Senra: You've been running it for 27 years.

Jason Fried: Yeah.

David Senra: You guys have been profitable every single year.

Jason Fried: Yep.

David Senra: You have millions of customers over the lifetime of the business. You've made hundreds of millions of dollars. And yet you told me that if you ever sell the company, you don't want to look at a computer again.

Jason Fried: Yeah, I don't. First of all, I don't like being consistent. I'm not that interested in being consistent, first of all. So your point about saying something that kind of conflicts with something else, you said, to me, it's just like, it's all about context. It's not about consistency. I don't find consistency interesting in any way, shape, or form. To me, it's all about the context, which is why I don't like to plan. I don't have long-term plans. I like to make things up as I go. So that's all tied into that.

Jason Fried: But yeah, I don't particularly like business. I like running my business. I figured out how to run my business, but the idea of me running another business, I don't want to do that. I don't want to do that. Maybe I could create another one that's mine, and I would like it, but I don't think I could, actually. And I think that we're a product of timing, and teams, and the right people at the right time, and the right ideas at the right time, and all that stuff. That's what made this thing and continues this thing.

Jason Fried: But to start over again, to run a business? No, thank you. And frankly, the other thing is, I would never trade my business for anyone else's business. I don't want anyone else's business. I don't want to put myself in someone else's shoes. I know how to do my thing, and that's enough for me. I don't need to stroke the ego and go, "I could do this again somewhere else. I could turn something..." I don't think I could do this ever again, but I don't need to, and that's okay.

Jason Fried: This sense of just being comfortable with what you've built and what you're working on now, being enough is, for me, a very peaceful place to be. And I think that that's unfortunately not something that's talked enough about in my industry, which is tech. Which is grow, grow, grow, get as big as you can, sell valuations, do it again, serial entrepreneurship. Like, it's boring to me. All that's boring.

David Senra: Okay, there's a million things I want to unpack.

Jason Fried: Let's go. Let's do it.

David Senra: I want to unpack there because you said a bunch of things.

Jason Fried: Yeah.

David Senra: The serial entrepreneurship I want to hit on, because you and I were talking about the conversation I had with John Mackey.

Jason Fried: Yeah.

Jason Fried: Yes.

David Senra: Where he was referencing some of his friends just love to start. And you're like, "Oh, I actually have this metaphor that I want to start talking about," and it is envelopes and letters.

Jason Fried: Envelopes and letters.

David Senra: Yeah, okay.

Jason Fried: Yeah.

David Senra: And then we'll go back to the fact that you don't like business, and that you only like...

Jason Fried: Yeah.

David Senra: And you're not... Really important, too, don't let me forget is, you have no sense of envy. I've known you well enough now to other people's businesses.

Jason Fried: I try not to. Well, yes.

Jason Fried: Yes.

David Senra: I don't think that is an act.

Jason Fried: No.

David Senra: Yeah.

Jason Fried: I would not trade my business for anyone's business, so I don't envy anyone's business. In fact, it'd be a downgrade. Anyone's. You could pick anyone, right?

David Senra: Oh, you've got to explain that.

Jason Fried: You've got to decide. If you've got to decide, you're like, "Jason, would you trade this business?" No. Any business, I wouldn't take. I'd take mine over anyone else's business. So I don't have...

David Senra: What is the underlying thought there? It's just like...

Jason Fried: I built the company I want to work at. I built the business I want to be in. Like, no one else has that. I have that. That's my thing. Now, they have their thing. I have my thing. I love what I've built. It's great. I'm very happy with it, and it's a good fit for me. I don't want to wear someone else's clothes. I don't want to do someone else's stuff. I don't want to live up to someone else's expectations. We have ours, we do our thing, we do our thing our way, and that's it.

Jason Fried: And if I had to do my thing someone else's way, it'd be a game of charades. And there's a lot of people, I think, playing entrepreneur. I don't want to play entrepreneur.

David Senra: What does playing entrepreneur mean to you?

Jason Fried: It means a lot of things to me, but I think there's a lot of people who... Let's get into the envelope thing, because this is kind of part of that.

David Senra: Okay.

Jason Fried: And I remember when I was getting started being an envelope guy. So the envelope, to me, there's this two sides of business, basically. There's the envelope, and there's the letter. The envelope is the outside, the shell, the business, the vehicle that holds the letter, and the letter is the product or products. I'm a product guy. I love product. That's all I care about. The business side just has to exist to hold the product, right? That's the vehicle in which the product travels in. But I don't care about the envelope so much, but there's lots of people...

Jason Fried: I remember this early on, when I first started my business, I was thinking about the brand, and the business, and how big it could be, and how do I describe it, and what do I call it? That's all envelope work. That's all on the outside. And I think there's a number of people, and by the way, it's fine. All this is fine. What I'm getting at is, you've got to know who you are and what you want out of yourself and what you want to do. And if you're an envelope person, that's fine. If you're a product letter person, that's fine, but you've got to know who you are. I know I'm not an envelope person.

Jason Fried: I don't just want to build shells that gets filled, and then I sell it and build another shell. It gets filled, and I sell it and build another shell. It gets filled, and I sell it. I want to just work on the letter, and the envelope is just the thinnest little thing that needs to be there to hold the letter. I think playing entrepreneur is like spinning up businesses all the time, making all sorts of stuff, and giving it a name, and giving it a logo, and trying to raise money, and coming up with valuations, and talking about all this stuff, and there's nothing there of substance inside that yet.

Jason Fried: Maybe there will be, but in a lot of cases, there's nothing. There's just losses. And then it's like a mad rush to get out at a certain valuation for other people who put money in. That's like turning a business into an asset, a financial instrument. It's just not interesting to me. I want to make things. I want to build products, and that's what I do. Again, that's what we do, and just the idea of a business being a financial instrument is just like, it's anathema to me. It's repellent, actually.

David Senra: You just used the word thin shell to describe the envelope. Why do you want a thin shell?

Jason Fried: I want it to be a thin shell.

David Senra: Oh! What does that mean?

Jason Fried: Well, I would say this, the more massive an object, the more energy it takes to change its direction, right? This is just like, this is getting back to basic physics. When I think of this stuff, and sometimes these metaphors don't perfectly line up, but in my head, I think of a thick business.

Jason Fried: It's hard to change, it's heavy, it's massive. There's too much distance between it and the customers and it and the product. There's space, right? If you just imagine something very thick, this is the thing that matters, and you've got to go through all this and compress all this down to get to the thing that matters. Like, I don't like that. I think the thing that matters should be big, and the rest of it should be as thin as possible, and so that's what we've tried to build at 37signals.

Jason Fried: It's a very thin business with a thick set of products that are good and solid and real and generate real profits and are real businesses, and then the rest of it is just enough to hold it all together. That's my vision for business. It's not the only vision. Plenty of people, way more successful than me don't see it this way. I don't care. Like, this is just how I see it and how I'm sharing it.

Jason Fried: And it's mainly just to show people that you don't have to go big. It doesn't have to be a big, thick, heavy, busy company. It can be very thin and then focus on the product and get to a place where you can find out people like you, get to this place where enough is enough, and then maintain. Another way to think about this for me, I always go back to these sort of weird metaphors, is, there's the hockey stick, chart, right? That is unappealing to me.

Jason Fried: I like more of a metaphor where it's more like a rocket into orbit. You've got to get off the ground, and you've got to break free of gravity. But then there's a point where you actually just want to sit in orbit and sort of maintain. You want to be within a certain range and fluctuate a little bit up, a little bit down, but be in this comfortable place where you're just orbiting. You're not breaking a force anymore. You're not pushing super hard.

Jason Fried: You're maintaining and maintaining a level of quality, maintaining a level of enjoyment, and just orbiting now. And I think that that's a really wonderful place for businesses to be. But I wouldn't encourage you to trying to get to orbit in year two.

Jason Fried: You've got to be on the ride up to break free of all the forces that are holding you back. But then you should also find a place where you can settle in an orbit, versus people who I think are just busy constantly trying to grow, grow, grow, and get as big as they possibly can, and I always say, "Why?" I'm like, so what if you're massive and you're twice as massive? So what? Why? Why? What's that all about? And they may have an answer for you. I don't know what the answer would be, other than just growing for growth's sake. But I'm a big fan of getting somewhere and then holding.

David Senra: When I think of you, I think one of your maxims that you repeat the most, is that idea. I hear you say, "So what?" all the time.

Jason Fried: Yeah, so what?

David Senra: With all those questions?

Jason Fried: Yeah.

David Senra: Explain more about that.

Jason Fried: Well, you'd have to ask a question, and I would be like, "So what? I don't know."

David Senra: It's like...

Jason Fried: Like, why grow? I mean, or maybe that's not a good one, but... For example, we're definitely leaving money on the table. I'm sure of it. We don't optimize our pricing. I'm not testing pricing, not constantly. We're not A/B testing constantly. I'm certain there's some formula that we're not following that could lead to more growth, more revenue, more whatever, more whatever, and my answer is "So what?"

Jason Fried: I'm very comfortable with where we are. We've got a great business, high margins, very predictable. We make new stuff all the time. We enjoy ourselves. We have a great time. Like, I don't want to f*** that up.

Jason Fried: I think people f*** it up all the time. You get to the right size, and for whatever reason, you can't be content there. And you push a little bit too much, too hard, and you lost what was great about what you were doing. And so, this whole thing about there's money on the table, and maybe there is, and maybe there isn't, maybe there's a way to optimize, maybe there isn't. It doesn't interest me, so it's "so what" to that. I don't really care.

David Senra: Tell me if this observation that I have about you is correct.

Jason Fried: Yeah.

David Senra: You seem to have this inherent natural revulsion against optimization.

Jason Fried: Yeah, I don't like optimization.

David Senra: Okay.

Jason Fried: Actually, okay, here's the consistency thing. It's all about context. I don't like optimization around numbers. We can make 5 million on this. Well, it'd be amazing if we could make 5.1 if we did XYZ. I don't care about the XYZ to make 5.1, but I am interested in optimizing a product to make it better.

Jason Fried: That, to me, is a worthwhile optimization. It's better for me because I use it. It's better for our customers because they use it. That's fun, but squeezing out an extra 100 grand off 5 million or something is just not fun. It's boring. Not fun, boring. Actually, beyond not fun boring. I don't even know what would be beyond that, but I'm not interested in that at all. I'd rather spend the money making the thing I make better.

Jason Fried: That is the thing I'm here for, not to squeeze an extra 100 grand out of something or an extra million out of something. I don't care. It doesn't matter. There's a point where you're doing well enough where it shouldn't matter anymore. Now, that might make me a bad CEO. Maybe someone else would come into my business and double the business overnight. That might be totally true, and I'm willing to accept that that's the case. My answer would be, so what? I don't care.

David Senra: I don't even think you think of yourself as a CE... And there goes the "so what" again.

Jason Fried: You asked for it.

David Senra: No, I don't think you can help yourself. I don't think you think of yourself as a CEO.

Jason Fried: I don't. I don't actually even like the term, frankly.

David Senra: Okay.

Jason Fried: Like, executive officer? What? Of what? I make products. I run the company with David. David and I run it together. I don't need the CEO.

David Senra: How do you say-

Jason Fried: Chief... Chief Executive Officer. Of what, again? Like, of what? We make decisions. That's what we do. We make decisions. We make products. We hire great people that we like. We find people with zero drama. We put together a team. We set out to make things. We take really good care of people, really good care of our customers. We make good products that we really like. Great products, hopefully, right?  I've got to leave a little bit of room there for some humility. We can always make better products, so I'm not going to call our products fantastic.

Jason Fried: They are good, great. There's always room for making those better. But as far as being a CEO and whatever that's supposed to mean, I don't know what the hell that means. Yesterday, I answered 200 emails from my customers. Some people would say that's irresponsible for a CEO to spend their time emailing customers. I think it's the best thing you can do.

David Senra: Yeah.

Jason Fried: But I don't think of myself as a CEO.

David Senra: I would say, whoever says that's not a good use of your time-

Jason Fried: A lot of people say it, dude.

David Senra: Yeah, but they need to listen to founders because they're all like this.

Jason Fried: Yes.

David Senra: The best entrepreneurs and founders in history, and I think that what me and you bond over is exactly that.

Jason Fried: Yes.

Jason Fried: Yeah.

David Senra: All I care about is products. I don't care about anything else.

Jason Fried: Yes.

David Senra: I think the way you think of yourself is a designer.

Jason Fried: Yeah.

David Senra: Is that correct?

Jason Fried: Yes. Sure.

David Senra: Okay.

Jason Fried: Little presumptuous. I think of it... Yes, fine.

David Senra: You're not a presumptuous person. I didn't mean it that way.

Jason Fried: I know you didn't.

David Senra: Yeah, but when I talk to you, it's like you've just designed everything in your life.

Jason Fried: I like to make things.

David Senra: Yeah.

Jason Fried: I'll just say that.

David Senra: You're a very thoughtful guy, and you see how much thought you put into the design of everything in your life. It just happens you've also put a lot of thought into designing products in the business. Again, to fit exactly who you are as a person.

Jason Fried: Yeah, as best I can. I mean, I have a family, and I have kids, and you don't always get things the way you want them to be, right?

David Senra: Yeah.

Jason Fried: But you do your best, and you live within a system that you're proud of and happy with, and that's, I think, a big part of it.

David Senra: The best founders, I see this over and over again, they're always... You said something about the thickness of the envelope and all this stuff that's between the person running the company and the customer.

Jason Fried: Yeah.

David Senra: You have to make that as small or almost non-existent as possible.

Jason Fried: Yeah.

David Senra: One of my favorite examples is this. This example from over a hundred years ago, Jim Casey, the founder of UPS.

Jason Fried: Uh-huh.

David Senra: What he realized is he had all these executives. He paid attention to incentives. He realized they would, over time, just tell him what he wants to hear. And so, therefore, he was getting his ass kissed all the time, not getting useful information.

Jason Fried: Of course.

David Senra: So he's like, forget this. I don't want to talk to them.

Jason Fried: Yeah.

David Senra: He had a driver, and they would drive on the streets, and he just says, "Every time you see a brown truck, brown UPS truck, you pull over," and he would just talk directly to the drivers.

Jason Fried: Awesome.

David Senra: He spent all his time talking to the person that's actually doing the work for the customer.

Jason Fried: Awesome.

Jason Fried: Yeah.

David Senra: I don't think anybody is saying, "Jeff Bezos."

Jason Fried: They know the most.

David Senra: I know he's a partner of yours.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: He owns a percentage of your company. He railed about this forever.

Jason Fried: Right.

David Senra: And he made every single executive, you'd have to spend a day or a week or a month on customer support.

Jason Fried: On support or whatever.

Jason Fried: Yeah. We do the same thing. We haven't done that for a bit, but we used to do that, and we should do it again, actually. We used to have this thing called Everyone on Support, where people would do it for a day, rotate through the company. Mostly so I would do it, and so David would do it, and now I do it anyway. But it's very important. When I lived in Chicago, there was a grocery store down the street called Olivia's. There still is.

Jason Fried: And  I've got to know the owner. And I appreciated the fact that he got to know his customers personally, because they'd walk in the store, and he would say hello, right? That's how  I got to know him. I don't, unfortunately, have that opportunity. We have hundreds of thousands of people who use our products, and it actually frustrates me that I don't know all of our customers. On the street, I could walk past 75 of our customers on a given day, and I wouldn't know that. He would know because he would know who they are, and he knew their family, the whole thing.

Jason Fried: So I've always tried as best I can to get as close to... I can't get as close to our customers. We have too many of them in that sense. But whenever you sign up for Basecamp, the first thing you see is a letter from me with my email address, with my signature and my email address, and I want my customers to email me. I don't want to hide from anybody. There's no AI. There's no assistant. There's no levels between at all. Just write me, and people do all the time. And we have in our books as well, we have our email address in our books.

Jason Fried: I want to get as close as possible to the people who use the things that we make, not just to make them happy, because I want to make myself happy, too. We are the first customer of our products. But to understand what they're doing with them, to understand the language they use, how they describe them, who they are, I want to know these things. Because somehow it permeates me, and I get to feel what it's like to be them, and get to understand what it's like for them to use the lever that we've made for them to move something.

Jason Fried: And there's no other way to do that for me than to just share my email address, because I don't get to meet people in person, like this guy who runs a grocery store. But I love businesses like that, people who... I love the dry cleaner who's been there for forty years. I love the local grocery store. I just love businesses. Those to me are so much more interesting than the billion-dollar whatever.

David Senra: Why?

Jason Fried: That's a great question. I feel like they're more real. I like real things for whatever that means. Define it however you'd like, but a billion-dollar business or a 10 billion dollar business, it doesn't feel like a real thing to me. It feels like a concept. Meanwhile, the dry cleaner down the street, I can drop off my shirt, I get it cleaned, I bring it up, I pick it up from the person who owns the place. This is her living. This is what they do.

Jason Fried: There's something for me that I connect with, something that's real that I feel like I can hold in my head, I can understand. I keep coming back to this... Well, not keep, but I have already in this interview once. This idea of surface area and a business as an object. I want to be able to see the whole thing and understand the whole thing. A massive entity with tens of thousands of people and billions of dollars and whatever. I don't understand it, and that's maybe my own shortcoming or whatever. I don't really care. Again, I don't need to understand that. It's not my thing.

Jason Fried: But I just prefer smaller businesses. Our customers are small business owners, and I don't care about enterprise customers. I don't want them. I like small, medium-sized businesses. They're more like me. I understand who they are. I understand what they do. I like that kind of stuff.

David Senra: So a business that can't be beyond a single person's comprehension, like you can understand. Dry cleaner's very... You gave this great story, I don't remember if it was in one of your books or not. There was like this... You have a love of craftsmanship that I get from your writing.

Jason Fried: Sure.

David Senra: And, yeah, there's a pizza place where it's like he will only sell, is it the fresh dough?

Jason Fried: Oh, yeah. Yeah.

David Senra: And he has no...

Jason Fried: It's a sandwich place.

David Senra: Okay, sandwich. Can you tell this?

Jason Fried: When they ran out of bread... I don't know if they're in business anymore. They're in Chicago.

David Senra: Okay.

Jason Fried: Vinnie's, I think, was the name of the place on Chicago Avenue, if anyone wants to look it up. Sandwich place, subs, Italian joint, whatever. You go in, and they're open as long as they have bread. And they just sell out, and they're closed. That's it. They're done.

David Senra: They're not making...

Jason Fried: They could sell more.

David Senra: That's anti-optimization.

Jason Fried: Yeah. They could, I'm sure, get more sacks of bread from the... It actually comes in a sack. Like the big baguettes or whatever. And they just run out, they're done, and maybe usually it's 2:30 or something. There's no hours on the door. They close when they close, when they're done for the day. There's something to me very poetic and beautiful about that, and again, enough. It comes back to this idea of there's enough in that. They're done for the day. It's enough. They sold enough.

David Senra: But he does that because-

Jason Fried: They could sell more, but then where do you stop? But this is the thing-

David Senra: But it's the quality, though, right? Because then-

Jason Fried: I mean, you're right. It is the quality, too, but they could get more quality bread also. Okay, so where do you stop? Like, where does this end? Well, we could stay open till 6:30. I mean, 7:00, probably. We could do 7:30. Someone's still at the door, we could do 8:00. You could see how this doesn't end, and a business like that could consume everything, and then you begin to not like it, because there's nothing else in your life but that. Then you're so attached to it. You can see how this could expand to that degree.

Jason Fried: I just think this idea of like, well, you're done at 2:30 is healthy. I think the business lasts longer because of that. I think if you think about... Like, you don't probably get bored of a business like that. There's something about that versus this idea of a business that you have to maximize and fully fill all your time, all your energy, everything, all the...

Jason Fried: I can understand the appeal there for a while, but I also think there's something very just simply beautiful about enough. Now, I don't own that business. They might wish they had a lot more revenue and sold a lot more sandwiches. So, I also want to recognize the fact that I'm looking at this from the outside. I'm an objective observer.

Jason Fried: I don't know the realities of that business, but I'm just observing what I think is a beautiful thing. Which is a business that's been around for a long time, family-owned, does enough business for them to support themselves and their employees, make great food for their customers. Isn't that what this is about?

David Senra: Are you proud of how long that you've been able to stay in business?

Jason Fried: I'm not proud of it. I didn't mean that in a negative way. It's like pride is not a...

David Senra: Is it important?

Jason Fried: I feel fortunate.

David Senra: Is the time important to you? If I could tell you, "Okay, you can make the same exact amount of money that you made in 27 years, but you made it in 15, and you're done," you'd take the 27?

Jason Fried: Right. I would take the 27.

David Senra: Because...

Jason Fried: The money is a side effect of all of this.

David Senra: I know.

Jason Fried: So, all the money does, like Patrick, who you interviewed, O'Shaughnessy, right?

David Senra: Yeah.

Jason Fried: I love what he said about work. It's I think something like, "I work so I could work more," or something like that, right?

David Senra: "The reward for good work is more work."

Jason Fried: There you go.

David Senra: It's to keep going.

Jason Fried: Great way to phrase it. And so, that's why 27 years is more interesting than 15. I like this stuff. The beauty about this, for me, is that somehow we've managed to build this system, this thing, this company, these products that sustain over a long period of time, that allow us to enjoy our craft and our work over a long period of time, and we are in control of that as much as we can be. The market can change. Anything can happen at any time.

Jason Fried: But I can control my costs, I can control my quality, I can control my messaging as best I can, and we can make the best thing we can over time and keep making that thing. That's what I want to do. This is my whole point. I don't want to trade my position with anybody for anything. I can love what other people do, too. I do. There's great products all over the place, and I'm like, "Wow, that's an amazing thing that someone made."

Jason Fried: For example, one of my favorite products is the Concept2 Rower. Are you familiar with this?

David Senra: Yes.

Jason Fried: I don't know anything about the company, but I can reverse engineer that I bet it's a badass, killer company, too, because that's how I look at things, by the way. I look at the products, not the companies. I look at the products and go, "Oh, that's a great product. I bet that's a great company." Or, "This product is, nah, I don't like this product. I bet the company's kind of..."

David Senra: I do this for people. If you can make a great product, you're probably an interesting person to talk to.

Jason Fried: Yeah, I could see that reverse thing as well. I mean, again, look to the inside to figure out what forms on the outside. So, Concept2 is probably one of my favorite products of all time, the Concept2 Rower. Their bikes are good, too, and they make a ski machine, too, but the rower is my favorite machine. And I love it because it is so well-built. First of all, it's under a thousand bucks, and it's been under a thousand bucks, I think, forever, and it's been around forever. There's been different variations of it, but they're always improving on a theme.

Jason Fried: It's roughly the same thing every iteration, but slightly better. It comes in a big box, very easy to assemble. It's a big machine, but it's very easy to assemble. The display is black and white LCD, not even LED, LCD, with five rubberized buttons, and then I think there's two other ones. It runs on C or D batteries. No electricity, no plugging in, no recharge. Oh, shit, it's done, get some new batteries. It just works.

Jason Fried: The buttons you press, there's no touch screens. The thing is reliable. It always works. It's incredibly durable. It does exactly what it's supposed to do with nothing else. And I look at that, and I go, "That is a perfect product." One of the few perfect products I've ever seen. A paper clip and a Concept2 Rower, hard to improve on both of those things. I have deep admiration for that kind of thing. I still wouldn't want to trade my company for theirs, because I don't know anything about what they do. I know what I do.

Jason Fried: But I can still respect and admire all sorts of things and all sorts of companies, but I still wouldn't want to be them. I like what we do, and I like that I can do it for a long period of time. And hopefully, I'll do it for as long as I feel like I want to do it, and then, at some point, we'll decide that we're not going to do it anymore, and I don't know when that'll be. I'm always a year-to-year guy. I'm a day-to-day guy when it comes to planning. Like I talked about a little bit earlier, I don't believe in long-term planning.

Jason Fried: I believe in being around for the long term, but I think the best way to do that is day by day, not quarter by quarter or year by year. Just figure out today and figure out tomorrow and figure out tomorrow. I've always been mystified by people who think they can figure out the next three years today, but they're afraid of figuring out tomorrow, tomorrow. I need to plan the next three years, so I can do that.

Jason Fried: I can plan, what, 900 or 1000 days in advance, but tomorrow, I can't figure things out if I don't have a plan. You can figure things out tomorrow if you can figure things out for the next 1000 days.

David Senra: Explain how you plan day by day.

Jason Fried: There is no plan. I mean, like, we have a direction. So, the way I think about this, and this is, again, another weird metaphor perhaps, but I think of our business and maybe me even like I'm a squirrel.

David Senra: Yeah.

David Senra: Okay.

Jason Fried: Probably weren't expecting this. So, you watch a squirrel run across a field. What does it do? It knows where it wants to go, roughly, and it runs, and it scurries, and it stops, and it looks around, and then it scurries some more, and it stops, and it looks around, and it scurries some more.

Jason Fried: It doesn't need to get exactly where it wants to go. It knows roughly where it wants to go, and it clearly doesn't know how exactly it's going to get there, but it knows where it's headed, and then it course-corrects. That's how I do it. So, at our company, we typically think about six weeks in advance, and that's about it. There's some occasional projects, maybe a few over the 27 years that we've done, that we needed to think further ahead. Like we just recently left the cloud, left AWS, and we're running our own stuff now in data centers.

Jason Fried: That was a much bigger project, okay? But most projects, 99% of them at our company, take six weeks or less, and most of them take just much less than that. But six weeks is the most we're willing to think ahead, and then day to day, the six weeks is like where the squirrel is headed, so it's not super clearly defined. It's generally defined, and then we figure it out as we go. We just figure it out as we go on a day-to-day basis. The teams figure it out as they go.

Jason Fried: I kind of set, or David or someone sets the target generally, not financial targets, but generally, we're headed in this direction with this idea, figure out how to get there on your own. We'll check in when we need to. You ask if you want some help, we're happy to come in. I'll review stuff as we go, but it's a bunch of course correction to get us there.

Jason Fried: And I find that that is the most honest, real way to get somewhere good, because in general, you know more about things the closer they are to you. So, I don't know what's going to happen five Mondays from now, but well, today's Thursday, so let's just take Friday.

Jason Fried: Five Fridays from now or tomorrow, I probably have a better idea of what might happen tomorrow than I do five Fridays from now. So, I'll worry about those when I get there. Let me worry about tomorrow. Let me nail tomorrow. Let me get tomorrow right. Let's do the right stuff tomorrow. Let's make the right decisions tomorrow, and then we'll make some more on Monday, and make some more on Tuesday, and make some more on Wednesday.

Jason Fried: Just make small decisions all the time, and don't put yourself in a place where you're making huge ones you're afraid of, and you can sort of get wherever you want to go for 27 plus years.

David Senra: There's a question that I keep getting asked by different people, so it must be a popular question, and I'm always perplexed by it.

Jason Fried: Yeah.

David Senra: They're like, "You seem to have something good going right now. What does success look like five years from now?"

Jason Fried: Oh.

David Senra: So, you hate the question I'm going to ask you.

Jason Fried: Yeah.

David Senra: I'm going to ask what your answer is, and I'm going to tell you what my answer to that question is.

Jason Fried: I don't know is the answer. I don't care.

David Senra: So what?

Jason Fried: So what? I don't even know five years from now. What's the difference? It's an interesting question because it's a directional question, but I don't care. I don't have an answer.

David Senra: My answer is boring. Just more of this.

Jason Fried: Yeah, sure. Well, exactly.

David Senra: I think there's...

Jason Fried: And that's essentially what it is.

Jason Fried: So, here's the thing about those questions. People answer those questions today for who they think they're going to be then. You don't know who you're going to be then. So, it's kind of a silly thing to answer or even to ponder. So, yeah, I'm with you, which is like this.

David Senra: I feel...

Jason Fried: This is the answer, basically.

David Senra: I've read all your books. I've listened to almost all your episodes. We've shared a bunch of meals together.

Jason Fried: Yeah.

David Senra: And I never even knew that you just did the day thing, too, because I was like I try to make a good 24 hours, and then I'm, "Oh, I like this day, so I'll do it again tomorrow."

Jason Fried: Yeah

Jason Fried: Yeah.

David Senra: And I had this line that I just said by accident. I was like, "Well, all a great life is is just a string of great days."

Jason Fried: Thank you. Of course

David Senra: So, all I need to focus on is just let me make a great day. And I told you last night, the way I think about, very similar to what you're doing or what I'm doing, is I'm just laying bricks.

Jason Fried: That's it.

David Senra: And today, I'm making a podcast, and tomorrow, I'll make another one, and a few days later, I'll make another one, and then I'll let the score take care of itself because I just like doing this, and I do it the way I want to do it, and I want to make a great product.

Jason Fried: Yes

Jason Fried: Yes.

David Senra: And so my answer to that question is just like this.

Jason Fried: This.

David Senra: Like, five years from now, I just want to be making more podcasts. I know I'm going to be reading books forever.

Jason Fried: Yes.

Jason Fried: Yeah.

David Senra: That's the only unbroken habit I've ever had in my entire life, over 30-something years. I can't stop reading, so I'm going to be reading books. So, that's what my other podcast is about, and I like talking to smart, interesting people that do great shit.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: And I don't think I'm ever going to stop doing that, so that's what this is.

Jason Fried: Yeah, great answer. And if one day you decide you don't want to do this anymore, then you just change.

David Senra: That's where me and you start to separate a little bit.

Jason Fried: I don't know, I said, "if." There might be a time.

David Senra: And I'll jump off a cliff.

David Senra: I'd be very disappointed.

Jason Fried: Maybe that would be the thing you start doing is jumping off cliffs. I don't know. Well, with parachutes, hopefully. But, I mean...

David Senra: I'd be very disappointed in myself.

Jason Fried: You might find another interest in your life. Something Jeff Bezos told me, which I've always kept close at heart because I've examined the things I've come into enjoying doing. He says, "You don't find your passions, they find you," and I've always believed that. And I didn't know that, but I've always believed it, but I didn't really know that I believed it. When he said it, I'm like, "Yeah, I have always felt that way," because I'm into things now that I wasn't into 10 years ago, that I didn't know about 10 years ago.

Jason Fried: And so, I'm hopeful for you, that there's other things, too, even though you can do this, too. But who knows? I think there's another beauty in just being empty and open to the world and how it presents itself to you, and you might find that you love this, and you love something else, and there might come a time where you don't like this anymore, and that's okay. It's okay. I can tell you don't believe me.

David Senra: No, it's not that I don't believe you.

Jason Fried: Maybe we do this until 80, right?

David Senra: Hopefully.

Jason Fried: And I hope you do, too, because you're damn good at it, right? But who knows? And it's okay. It's okay. This is why the whole idea of a five-year plan, it's kind of a ridiculous thing. How about just get tomorrow right? Get tomorrow right, and by the way, if tomorrow wasn't right, this is the thing, I think this gets back to, in some ways, tying it back to the thinness, and you want to find tiny units, find small units. So, a day is a good small unit, right?

Jason Fried: A simple decision is a good small unit. And the good thing about that is, if you screw up, it's not a big deal. If tomorrow sucks because whatever happened, okay, it's behind you in 24 hours. It's over. Versus big, huge decisions, where you take eight months to think about it and pull in all these people and set up all these contingencies, and you make the big decision, and it goes sour, it goes south, whatever. Maybe it works out, but maybe it doesn't. And then it's so hard to make those calls.

Jason Fried: It's so hard to deal with the ramifications of those things if they don't work out. Like, make things small, tiny little units that you can throw them away if it doesn't matter. What you basically want then is enough good things, enough good units in a year, right? Not one great year, one great plan, but enough good little things, because you know you're going to miss a few things, so who cares? Throw them away, it doesn't matter.

Jason Fried: Small units, bricks, build that way, and I think that you become more anti-fragile, basically, in that way. When you're just like little things, and they can't throw you off too much if you get something wrong and it's small. Now, someone could say, "Well, you're going to miss big opportunities," and, yes, maybe so. So what? So what? If I can stay alive doing the thing I'm doing and running the business I want to run, I don't need the other big opportunities.

Jason Fried: Stop worrying about all the other things you can maybe do, and just focus on the thing that you're doing, and make that work over, and over, and over, and over, as long as you want to do it.

David Senra: Brad Jacobs has started eight separate billion-dollar companies. He said, "I've come to know a lot of extremely successful people in my life, and they all have one thing in common: they think differently than most people. All of them, to a person, have rearranged their brains to prevail at achieving big goals in turbulent environments where conventional thinking often fails."

David Senra: What Brad noticed is that great business leaders are pattern spotters, but you can't spot patterns if you can't see all of your data. Most businesses only use 20% of their data. Why? Because 80% of customer intelligence is invisible. It's hidden in emails, transcripts, and conversations.

David Senra: That's where HubSpot comes in. With HubSpot, all of your data comes together so you can see the patterns that matter. This is important because when you know more, you grow more, and that is a pattern that never fails. Visit hubspot.com today. That is hubspot.com.

David Senra: Do you feel you have a narrow aperture with the world? I feel like you're like...

Jason Fried: No.

Jason Fried: I don't.

David Senra: Okay. Because I feel like...

Jason Fried: Well, actually, what do you mean by that, first of all? Because I'm guessing.

David Senra: Like what you just said. Why are you worried about all these other opportunities out there in the world? You just seem to be focused on, like, "I'm building the business the way I want. It's a perfect business for myself." You're kind of not oblivious, I don't mean this, obviously, in a disrespectful way by any means. You don't really care what other people in your industry are doing. You have a narrow focus on...

Jason Fried: Yeah, I don't know if it's narrow or wide, it just is. I'm doing what I'm doing, and it doesn't matter what they're doing.

David Senra: How often are you paying attention to how other people are making their products?

Jason Fried: Very rarely. I don't actually want to pay attention to it.

David Senra: Why?

Jason Fried: I think what ends up happening is, and you see this in my world, you see it everywhere: everyone follows everybody else. Because when you're paying so much attention to what everyone else is doing, that's the way you think it has to be done or can be done. You're not open to alternatives because you don't see them anywhere. And people then build out of fear. Like, "Gosh, they're doing this, they're launching this. I have to meet them. There has to be parity between my product and theirs." Then you end up following everybody. I don't like that.

Jason Fried: I'd like to take inspiration, if I'm going to take inspiration from anything, product-wise, it's the Concept2 Rower. It's not another piece of software. I'm not inspired by other software. I like buildings, I like furniture, I like Concept2, I like watches. I like other things outside of my world that I can sort of admire and understand, and sort of get fired up about. And I don't know if those things come back. I don't think they need to come back.

Jason Fried: Everyone's always like, "How does that come back and help you build your business?" I don't know. I don't care. Why does it have to? Why does everything have to come back to business? Why does everything have to influence your decisions? These are all things that just happen, they exist in your world, they happen to you and they form you, and you're not even aware of most of it. And I think if you admire a variety of different things and pay attention to different things, and enjoy a walk in the woods...

Jason Fried: A few days ago, it was like 4:45, you know, California, here, the light is just beautiful at the end of the day. I'm just sitting outside, looking at the way the sun is raking over the hills. I'd rather look at that than this piece of software. I'm learning more from that. I'm getting more from that than I am a competitor's product. I don't want to look at that. I want to look at the sun, I want to look at the ocean, I want to go for a walk, I want to look at nature, I want to look at great furniture, I want to be in great architecture.

Jason Fried: That fills me up in a way. I'm getting enough of the software world by being in it. I don't want to soak in it. I want to soak outside of it, and then my only soaking in the software world is my own stuff. That's enough. It's enough for me to focus on.

David Senra: Tell me about your idea of Galapagos Island product design.

Jason Fried: There's something really cool about islands that have evolved on their own. I don't know, I've never been to the Galapagos. My wife's been. She asked me if I wanted to go. I didn't want to go, because it's too far. But I should have gone, probably. Actually, I didn't want to go, frankly, because part of that was it was too far. I also felt like, "Can we let it be?" She loved it, and I'm so glad she went, and the pictures are incredible, and it seems like an amazing experience.

Jason Fried: But there's something very cool about things that have just evolved on their own, that are not influenced by other things, and I try to think of us as the Galapagos. I don't think of us this way, really, but conceptually, I don't use the word the Galapagos Island of the software industry. I don't use that. But I do think of us as actually an insular group focused on solving a problem our own way, without paying too much attention to what everyone else is doing.

Jason Fried: I'm aware of it because I live in it, but I'm not seeking out ideas from other companies in our field. I think that that's actually a slippery slope. It is because we see so much copying in our industry. Someone has a successful product, and then all future products for the next three years look just like theirs. That says to me that there's danger here. Don't fall into that trap. Our stuff looks different than everybody else's stuff. Our stuff works differently than everybody else's stuff.

Jason Fried: Nothing works like Basecamp, HEY, Fizzy, it's all different. And some people hate the way our stuff looks and works. Fine. Don't care. We have enough people who love what we do, and it's an expanding pie of people who are into what we do, and we love what we do, and again, that's enough for us.

David Senra: Even your landing pages look different. They're essentially a letter from you, describing what the product is and why it exists.

Jason Fried: Yeah

Jason Fried: Yeah, I always try to build things that I would want to see. I build the company I want to work at, I hire the people I want to work with, I try to write. I do all of our writing. I don't do the design, I work with our designer to do a lot of that, but he's sort of the visual person there. But I do all the writing, and I want every word to land with meaning. This is, again, like thin, thick.

Jason Fried: I don't like thick stuff. Thin, how can I just get to the right point but not be sterile? It's a problem sometimes with getting to the point, you can be sterile. So, there should be a little bit of bounce, a little bit of rhythm in the writing. It should feel nice. You should be carried through it. There should be some momentum in there, and I just love doing it. That's my favorite thing to do, actually, at the company is write. But we just do stuff that we like. I like that style. If you look at my product demos, I always do the demo for the product, like the launch. They're long, and they're unedited, and I screw up a bunch, and I don't care.

Jason Fried: If I was sitting with you, what I want to try to get to with this kind of stuff is, if I'm showing you something, our product, literally, you're behind me or sitting next to me, and we're looking at this thing together, if I screw up two minutes in, I'm not going to go, "Let's start over." I'm just going to keep going, and so that's how I want these to feel. I want to connect with people in a real way. This is a real person showing off a real product. This is a real person writing a real thing. My name's on it, my signature's on it, my email is on it.

Jason Fried: We are who we are. We represent ourselves as we are. We are not a corporate entity hiding behind a structure. We're not a CEO or a CTO hiding from our customers. We don't have a board. We don't have any of these things. It's just us running the show, and the show is open for anyone to see. And we open source most of our work. We're very open about sharing everything we know as best we possibly can. I just feel like there's no reason not to.

Jason Fried: I just want to be direct and clear with people, and hopefully, they like that, and some people don't. Some people are like, "Oh, you guys are too small. I can't trust you." I'm not out to convince anybody of anything. That's the other thing. I don't want to convince anyone. I don't like marketing language. I don't like tricks. Here we are. Here's what we do. Here's what our product does. That's the best we can do, and that's the best I want to do, and I think it's the honest way to be. And take it or leave it. Some people don't like it. That's totally fine. I get it.

David Senra: I love the idea of doubling down on authenticity and leaving the mistakes in. I remember reading one of your essays a long time ago. I can't remember the culture, but they would do...

Jason Fried: Navajo rugs.

David Senra: Okay.

Jason Fried: I'll tell you the story.

David Senra: Yeah.

Jason Fried: I was in Wisconsin, in this little town called Mineral Point, Wisconsin, small, little town, about 50 miles west of Madison, and I was wandering through this gallery. Strange. It was this weird building, and it looked like a junkyard inside. You peered in, it's like, "What is going on in here?" And I saw some old man in the back. Like, "There's going to be something cool here." So, I knock on his door, I walk in. There's some rugs hanging, but there's also junk everywhere. Anyway, he comes out, and you're like, "Okay, this guy's a character."

Jason Fried: I love characters. I love old people. There's something going on there, right? I'm like, "Who is this guy?" So, he's a Navajo... He's dead now, but he collects Navajo rugs. So, anyone can't go there today, is what I'm saying, but he collects Navajo rugs, and I find them very beautiful. They're very simply patterned, and the colors are very vibrant, and they're very interesting, and I don't know what it was, they spoke to me, right? And I don't want to analyze why either because I find that that's a great way to ruin any experience, is to try to figure out why.

Jason Fried: Just does it or does it not? It does. I love these things for whatever reason. So, I go in, talking to the guy, and I notice that they have a lot of errors on them. There's what I thought was an error, there's geometric shapes. So, their rugs are very geometric. They're stripes, they're squares, they're triangles, they're all sorts of different shapes. And a lot of them weren't quite right. You can look at a shape and go, "It's not..." They're trying to make a perfect triangle, but it's not quite right, and I asked him about that.

Jason Fried: Or there's a stitch that's off, very clearly off. I'm like, "They could have just taken that out and redone it."  And again, I don't know if this is true, but this is what he told me, which is the Navajo, they don't see those as mistakes. They're just a moment in time, and he relayed it this way. He's like, "If you're walking on a path, if you're climbing a mountain or something, and you're going on a path, and you trip or you stumble or whatever, you don't start back." You can't take that stumble back. It just happened.

Jason Fried: The Navajo leave these in their rugs because they just happened, and this is a record of what happened. I love that. I just thought it was so lovely, and I've tried to do that with the things that I do. I don't want to leave typos and stuff. That's not quite the same thing. But if I make a mistake on a video or something or whatever, like whatever.

Jason Fried: That's what you would do in the real world, so I'm comfortable with that. I've always found that to be very, again, a very beautiful thing, that these are not mistakes. Mistakes are a concept we put on ourselves when we do something that wasn't what we intended. Why does that have so much weight? Maybe what we intended was wrong, too. I don't know. Are these rugs worse because there's a stitch off? No, they're not worse. They're better.

Jason Fried: And that's kind of what I'm striving for with this stuff, is not to take things so damn seriously and build a company that's afraid of itself and afraid to do anything wrong and afraid to have an opinion. All these companies, not all, that's a very broad statement, all these companies.

David Senra: Yeah.

Jason Fried: You know what? Everyone's afraid. Companies are afraid, the PR people, and they've got to talk to lawyers before they publish anything. Everyone's afraid of everything, of saying something wrong, doing something wrong, being wrong in some way. That is not endearing. I think people want to do business with people, and they have to do business with companies because companies provide a lot of product. But I think they really want to do business with people, and maybe this is why I like the dry cleaner. Maybe this is why I like the grocery store.

Jason Fried: Maybe this is why I like running my business my way. I feel like people are dealing with people. We don't have a big corporate structure. We're just 62 people currently doing the things that we're doing. We're all accessible, all reachable. No one's hiding from anybody. This is what we do. And there's, again, a thinness, a directness to that which just has an aesthetic value to me that I can't quite explain. It's like the quality that cannot be explained.

Jason Fried: I think it might have been Christopher Alexander or something, who was an architect, who talked about this. I might be totally off on this, but I think conceptually the idea was you can go see buildings in native villages, and there's no architect that made any of this stuff. They didn't have any architects. They had people making places for them to live and work and worship, and there's a certain quality to that which is not textbook high quality, but is beyond high quality because it's a perfect fit for what they wanted for themselves. That's the kind of stuff I like to build.

David Senra: It's kind of how you're designing your company.

Jason Fried: Yeah. Perfect fit for us, for what we want and what we need, and again, getting back to the original thing, how many other people are there out there like us? Enough. That's the business model.

David Senra: This is exactly how I started doing the podcast. I think I'm drawn to that, too. I think in people, not companies, right?

Jason Fried: Yeah

David Senra: And this is why I was drawn to podcasts to begin with, because it's impossible. Some of these podcasters that I was fans of before I had a podcast, I've heard them speak for hundreds of hours. You can't hide who you are at that point.

Jason Fried: Right.

David Senra: You're going to like the good, you're going to hear the mistakes, and you used the word endearing, and that's exactly how I feel for some of the people that I admire.

Jason Fried: Mm-hmm.

Jason Fried: Mm.

David Senra: There's something about them that is endearing. In fact, a friend of mine just texted me this morning, my friend Lulu, she was listening to one of my old podcasts on Napoleon's maxims on Founders, Episode 337, if I remember correctly.

Jason Fried: Uh-huh

Jason Fried: Yeah.

David Senra: And she thought it was hilarious that I didn't edit out the fact that I was mispronouncing all these French names. And I'm just like, I don't know.

Jason Fried: Right.

David Senra: I'm reading from the book. I'm like, "I don't know what this is.

Jason Fried: Yeah.

David Senra: I don't speak French, so I'm just going to do this phonetically."

Jason Fried: Yeah.

Jason Fried: Yeah, just do it your way.

David Senra: But it was endearing to her that I didn't act like I speak French or anything.

Jason Fried: Of course

David Senra: I was like, "I read books, and I'm just guessing at how this is pronounced."

Jason Fried: Yeah.

Jason Fried: You're not putting on airs. I admire anyone who is truly themselves, and that's what that was for you. You're like, "I could have probably faked the accent." You watch TV news, and the guy uses the Hispanic accent for some Spanish word, and you're like, "That's weird."

David Senra: I know.

Jason Fried: You're trying too hard. If you don't speak Spanish, you don't need to fake the accent to try to speak Spanish, is what I was trying to get at. But you see it all the time. I don't know how to pronounce French words either. I'm not even going to try. I'll just say what I say and read it phonetically, and you could even say, "I don't know how to say this."

David Senra: I do say it.

Jason Fried: Yeah.

David Senra: Exactly.

Jason Fried: I don't know what this is. You're going to laugh at me, but this is what it... And then you move on, and no one gives a damn because you're you, and that's not the point of the story. The point of the story is not perfect French pronunciation with seven words out of 5,000. What is the story, and who's telling it, and why are you telling it? That's what matters. Figuring out the stuff that actually matters is what's important about that process, and I think, again, running a business and making decisions about product, it's like, "What matters? What doesn't matter?" That's fun.

David Senra: Going back to you writing these letters for the landing page.

Jason Fried: Yeah.

David Senra: Do you do it like Bezos, where they write it before the product is created, or you're doing it after the fact?

Jason Fried: In the middle, usually. So, like with HEY, I wrote one for HEY, which is our email service, and before we launched, before the product was even anywhere near done, I wrote the letter.

David Senra: I need to interrupt you. I was a fan of your writing.

Jason Fried: Yeah.

David Senra: The first time we met, I showed you the Amazon. I was like, "Listen, I have receipts here. I've been reading your stuff for 13, 15 years."

Jason Fried: Yeah, yes.

Jason Fried: Yeah.

David Senra: I bought HEY, just because I wanted to give you money, because I'd buy your books, but I didn't have a team, and Basecamp's project management, and I'm working by myself.

Jason Fried: Right.

Jason Fried: Yeah.

David Senra: And so I couldn't ever give you money, and then you built up so much goodwill by teaching me so much through your writing, that I was like, "Oh, I use email."

Jason Fried: Yeah.

David Senra: "I'm going to buy that product." So, I am a proud subscriber of HEY just because I was like, "I've got to give this... I've got to pay you back somehow."

Jason Fried: I appreciate that.

Jason Fried: Thank you.

Jason Fried: Thank you. I do that with other products, too, where I'm not going to use them, but I just love the people behind them, and you want to support them.

David Senra: It happens so much.

Jason Fried: And it's a cool way...

David Senra: This goes back to we identify with people, not companies.

Jason Fried: Yes, and it's a cool way to purchase something.

David Senra: Yeah.

Jason Fried: Sometimes, the use is the support, not the actual use of the product. But anyway, during the development of HEY, we launched this pre-launch page months before HEY was done, and so I wrote this letter about why email is a beautiful thing, and for the longest time, people have hated email because they despise it because email has gone off the rails, and we can bring it back on. Do you remember when you used to get an email from someone you loved or your grandparent or an old friend?

Jason Fried: It's a wonderful thing to get an email from someone who you care about. The problem is that most emails now are spam and sales and garbage, and meetings and shit. Anyway, we can get into that, but the point was, to your question, was I wrote that in the middle. I didn't know what the product was going to be yet. We're going one day at a time. I didn't know what it was going to be.

David Senra: Was that the why behind the product? How would you describe...

Jason Fried: It was the love behind the product.

David Senra: Love?

Jason Fried: Yes.

David Senra: Say more about that.

Jason Fried: Well, I don't want to get silly about it, because you can't really love...

David Senra: It's not silly

Jason Fried: I know, but it's a different version of love.

David Senra: No, I love podcasts, so I know exactly what you're talking about.

Jason Fried: Yeah.

David Senra: No, I love them.

Jason Fried: Yeah.

Jason Fried: Yes.

David Senra: And when I make one, and I listen to it before anybody else does and I'm like, "I'm happy with this," that is love.

Jason Fried: Yes.

Jason Fried: Yes.

Jason Fried: Yes.

Jason Fried: Yes, that.

David Senra: You're not silly. It's not silly to me.

Jason Fried: Yeah, I know, I know. Okay, so there's a certain warmth and tone that comes through when you make something you're really proud of in that way. We got proud about running the business for 27 years. I'm really proud of the products we make. The business, again, is like the envelope. I'm not proud of the envelope. I'm proud of the things that sustain the business, which are the products. And I love getting them as right as I possibly can.

Jason Fried: And there is a warmth that comes to you when you're really proud to share something that you're done with, that you've finished, that you want to put out there in the world. And it could be a letter, it could be a line, it could be the right word in the right place, it could be an entire product, and it can also be a company, in a sense. But there is love reserved for that, for sure.

David Senra: So, this is a love for the decentralized... I remember reading this. You were talking about if the actual creation of email is actually a miracle, we've just kind of f***** that up.

Jason Fried: Yeah. It's amazing that anybody in the world can get in touch with anybody else. There's no platforms. Everything else is a platform. You want to write someone on WhatsApp? Well, they have to have WhatsApp. Signal, they have to have Signal. Whatever, right? Email, beautiful thing. It's as beautiful as the web. The web is beautiful because anyone in the world with a web browser made by any company can use HTTP and connect to some other website. Same thing is true with basic email.

Jason Fried: These are wonders of the world, and how did they become so despised? I blame Apple, I blame Google, I blame Yahoo, I blame Microsoft for making shit email products that they just don't care about. Now, they've started to care more about them, but they didn't care about them for a long time, and everybody knows that nobody cared, and so we care. I live in email sometimes.

Jason Fried: We don't use email inside our company. We use Basecamp, but for the outside world, we use email. And I want to use tools I love. I want to use tools that matter to me, and if I'm going to spend most of my day in Basecamp, I want to make Basecamp. If I'm going to spend the other part of my day in HEY, in email, I want to make an email tool that I'm proud of, that I want to use, that I have a certain love for, and that's what that is. And that letter, it was a love letter, in fact, it ended, if I remember correctly, like, "This is a love letter. HEY is our love letter to email," and I meant it.

Jason Fried: Yeah, it's a great thing. It's an amazing thing.

David Senra: You just used the word tool a few times.

Jason Fried: Yeah.

David Senra: Do you identify with Tobi Lütke? He's like, "I'm just a..."

Jason Fried: Toolmaker.

David Senra: Yeah. "I'm a toolmaker."

Jason Fried: That's all I make, too. I make tools.

David Senra: That's how you think about it?

Jason Fried: Yeah, so when people are like, "What do you do?" I go like, "I'm in the software business," so they understand what I do, but I don't like that term. I also don't like, "I'm in the tech industry." I'm not a tech person. I don't like that. I make tools. They just happen to be made of software. That's all I know how to do. I don't know how to make things out of wood, but I know how to make things out of software and code and design and conceptual ideas, and so, yeah, I make tools. We make tools. We make levers. It's just a lever.

Jason Fried: It's a lever that lets you do more with it than you could without it. That's all it is. You can move more things. You can organize more people. You can come up with better ideas. You can see those ideas through. You can make progress with the products that we make. That's what a tool is for, is to make progress.

David Senra: I'm fascinated by a lot of your time spent out of the business, and a lot of the inspiration that you derive in life seem to be from physical things. You just named a bunch.

Jason Fried: Yes.

David Senra: And you have a love of architecture, we just talked about, watches, cars, the Concept Rower. When you said, "You could change your mind, David, maybe you're not podcasting in the future."

Jason Fried: Yeah.

David Senra: What I know for sure is if I ever do anything else, it's going to be physical, because the same phenomenon where I barely look at numbers.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: I know you barely look at numbers, but it's just numbers on a screen.

Jason Fried: Right.

David Senra: And those numbers happen to be big, but you don't understand that.

Jason Fried: Yeah.

David Senra: You just don't feel it.

Jason Fried: Yeah.

David Senra: I remember, Mark Leonard of Constellation Software did this podcast.

Jason Fried: Mm-hmm.

David Senra: He talked about one of his most fulfilling jobs he ever had was not starting and compounding whatever it was, 50 million to 80 billion or whatever he's done with pure software.

Jason Fried: Sure

Jason Fried: Yeah.

David Senra: He was building stone walls.

Jason Fried: Mm.

David Senra: And even to this day, he said he'd go... I think he was a kid or a young man, maybe he was in his 20s, 30s back then. But you can go to where the stone wall that he worked on 30 years ago, and he's like, "Point at it," he's like, "I did that."

Jason Fried: That's badass.

David Senra: "I made that."

Jason Fried: Yeah.

David Senra: Why do you draw so much inspiration from physical things?

Jason Fried: I'll take some guesses, because I don't know. Just like I don't know why I like certain flavors. I just do, right? You can't really explain these things, but if I had to guess, again, it comes back to there's something real about them. I like being able to hold things, touch things. I like texture. Something you'll see in a lot of our software products is actually texture, which is not real, it's simulated, but a lot of software these days is very flat. I like gradients and colors and lines and some texture.

Jason Fried: I just find it to be very fulfilling and real to rub your finger over something and feel it. I like patina, I like age on things. Software doesn't age. I mean, it does age. It can look old or whatever, but software looks the same over time. A great building, a great brick, to get back to bricks, bricks are beautiful because they look even better as they get older. They collect age on them. They get stronger. They build into other things.

Jason Fried: There's something about the physical world to me that is just... We're from it, okay? We are it. We are part of it. There's something so fundamental about it that I try never to get too far away from it. I would much rather lay on the ground than fly in the air, you know? I just want to be closer to things that are real. Now, flying in the air is real, too, of course, but you know what I'm saying. I'd rather walk somewhere. I'd rather drive. I'd like to be closer to the ground. I've begun to collect rocks that I think are cool looking.

David Senra: Oh, now you can move to Malibu.

Jason Fried: Yeah.

David Senra: Are these rocks crystals?

Jason Fried: They're not crystals. I was going to save that in case you asked me. They're not crystals. I'll just find something at the beach, or I'll find something interesting with a cool pattern in it, and I just like it. I don't know. I love nature. I love all the textures and patterns and colors. Like, for example, when you're coming up as a designer, in the early days when I was designing identities, like logos and stuff, you'd go through these logo books or corporate identity books. I think there was an organization called... I want to call it Brand, but maybe I'm wrong. Print, actually. It was this magazine that had all these pictures of business cards and stuff, and every designer I know would look through other business cards for inspiration, for color patterns and palettes and layouts, and I'm like, "Go outside." The best designs ever are right there.

Jason Fried: That leaf is the best it's ever been. Obviously, it has survived and evolved. This is a great thing, and so if you want to find great colors, look at a bird. Don't look at a book. Look at a leaf, right? Look at the ocean. Go to a tide pool and just look at the colors in that tide pool. Look at the way the light reflects. Like, that's the real stuff, and... I have goosebumps. For me, whatever it is, whenever I talk about this, it's just fundamentally real to me, and I just love it, and I love the screen, too. I love making software, too, but probably because I'm in that a lot, I really like not being in that, too.

David Senra: I don't think you love the screen. You said if you sell your business-

Jason Fried: Right now, I do. If I...

David Senra: All right, we never answered that.

Jason Fried: Okay, let's get into this.

David Senra: Yes. You said if you sold your business, you're never going to use a computer again.

Jason Fried: Yeah.

Jason Fried: Well, I said I would never start another business again. What I would like to do is I'd like to shut my laptop. I'd like to turn off... Yeah, okay. I don't need a screen to survive my days. I'd like to close my laptop for a year and just not use it. I'll use my phone because I get in touch with people, right? But I don't want to "compute." I don't need to compute. Let me just close it and walk away. Again, this isn't.. The computers are some of the most, probably the most amazing tool humans ever made. So, I don't despise them, hate them, but I could take some time away from them.

David Senra: The... Yeah.

Jason Fried: But I think time away from nature would bug me a whole lot more. If I couldn't go outside for a year, it'd bug me way more.

David Senra: Oh, you'd go insane.

Jason Fried: Yes.

David Senra: Yeah.

Jason Fried: I'd jump off the cliff.

David Senra: I think people have gone insane.

Jason Fried: They have, for sure. Right, exactly, so I want to be out. I want to be out there. I think it's just a wonderful... So, the screen is wonderful. Software is wonderful. Computers are incredible things, and right now is an amazing time for computers, one of the most amazing times since the web back in the late '90s or mid-'90s, really. And it's cool to live through both of these moments. But I'd still rather play with some bricks and work on a stone wall, even though I don't know how.

Jason Fried: But that wouldn't pay my bills either, so I have to be practical. I've built a great software company. I like this stuff a lot. I don't know how to build stone walls, but I wouldn't mind playing with them.

David Senra: The bills are taken care of.

Jason Fried: The bills are, but I still...

David Senra: I don't think you have to worry about that anymore.

Jason Fried: I don't, and I don't do it for that reason.

David Senra: I know you don't.

Jason Fried: But yeah. My point is, had I built stone walls for 27 years, I'm not sure where I would be, you know?

David Senra: No, the bills would be piling up.

Jason Fried: My hands would be very sore, for sure.

David Senra: The bills would be piling up.

Jason Fried: Yeah, yeah.

David Senra: One of the people I most hope to get on the show and I want to talk to is Christopher Nolan.

Jason Fried: Yeah, uh-huh.

David Senra: Have you ever looked into his personal philosophy at all?

Jason Fried: No, I just like his movies. Yeah.

David Senra: Okay, so there's something that me, you, and him, I think, have in common. He desires to live in an analog world. I'm almost positive that's a direct quote.

Jason Fried: Yeah.

David Senra: It might be me summarizing reading his biography.

Jason Fried: Yep.

David Senra: And so if you think about the juxtaposition between, like, you make software, but you want to be on a hike outside.

Jason Fried: Yes.

David Senra: You want to look at the ocean, right?

Jason Fried: Yeah.

David Senra: He makes some of the most technologically advanced films that have ever been created, and yet he doesn't have a cellphone. Like, you can't get in touch with him.

Jason Fried: Love that.

David Senra: You have to email his assistant, he has to track him down.

Jason Fried: That's amazing.

Jason Fried: Yeah.

David Senra: He will purposely put himself into a difficult position. So, he'll drop into a new city.

Jason Fried: Yeah.

David Senra: He doesn't have a smartphone, so no GPS.

Jason Fried: Right.

David Senra: He's got to go up to somebody and be like, "How do I get to the deli?" or whatever.

Jason Fried: Yeah.

David Senra: If he wants you to be in his movie, like, "Oh, email me the script," he's not emailing you the script.

Jason Fried: Yeah.

Jason Fried: Right.

David Senra: Okay? He is printing it out physically, flying to you.

Jason Fried: Yes

Jason Fried: Yeah.

David Senra: So I'm Christopher Nolan, and I want you, Jason, in my movie.

Jason Fried: Yeah.

David Senra: I'm showing up at your door.

Jason Fried: Yeah.

David Senra: "Here's the script," and you're like, "Great, I'll read it."

Jason Fried: Yeah.

David Senra: And I'm sitting here until you're done reading it, and then when you're done...

Jason Fried: Waiting.

Jason Fried: Take it back.

David Senra: I'm taking it back.

Jason Fried: Amazing. Amazing. That's cool.

David Senra: And I feel that exact same way, where it's like, your entire product is delivered digitally.

Jason Fried: Yeah.

David Senra: Mine is, too.

Jason Fried: Right.

David Senra: But I like to read physical books. I like to be in person. I will not do a remote podcast.

Jason Fried: Right.

David Senra: Now I've got to the point where I won't even go on other people's podcasts remote. I was like, "No, no, like, let's go meet and hang out."

Jason Fried: It's cool.

David Senra: I want to talk on the phone if I can't be with you in person. I don't want to text you.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: I want to live in an analog world. I just feel better being outside reading physical books not looking at a goddamn screen.

Jason Fried: Yeah.

Jason Fried: I'm with you, and what's important about that is not actually... This is going to sound... Whatever you said doesn't matter, actually. It's that you know who you are. That's what matters, that you know that you like that, that you've figured out that you like that. It's good to figure out what you like eventually. Like, a lot of people don't know what they like. They like what other people like. They like what they're supposed to like. They live up to other people's expectations. They kind of run someone else's business, in a sense. Not like an executive running their business, but people grow businesses that they think they have to grow because that's what you do.

Jason Fried: They make decisions they think other people would make. They don't even have a sense of who they are and what they're all about yet, and I hope all of them find it because it's a wonderful thing when you know what you're into, and also that you know maybe that might change, too, but you know right now you're into that. The other thing is, you don't need to pick sides. You can love digital, and you can love physical.

Jason Fried: They're all the same thing. We live on this speck of dust, you know, in space. It's all the same thing, right? So, it doesn't, really, any of it, matter. What you like and why you like it, just that you do, and that you know that you do. You don't even know why that you do, but that you do, and you respect and treat yourself to those things that you find beautiful.

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David Senra: So, you told a story earlier, when you were making products, you were, like, in high school, and you were designing it just for you.

Jason Fried: Yeah.

David Senra: You're the first user. That is an indication that you're comfortable trusting your own judgment. You just said it's really important to know who you are. At what age do you really think that you finally figured out who you are?

Jason Fried: I think probably more recently, frankly, than then. I think I knew what I liked to do, but I'm not sure I still know fully who I am, but I... That's the big question, right? Like, who are we and the whole thing, right? I don't totally feel like I should... No one should be certain about that. But I feel like I've come more into my own actually since getting married and having kids. Looking back on maybe how I was, how I acted, how I was in the world, I'm glad I am who I am now than who... I wouldn't want to be that person again.

David Senra: Why? Didn't you say you used to have, like, anger?

Jason Fried: I think I was... Yeah, I was definitely more of a punk, you know? Like a young...

David Senra: Say more.

Jason Fried: I don't know. I think I probably resented things for some reason. I was sort of... I had a chip on my shoulder. I mean, maybe that was good. Like, you've got to prove yourself when you're new into something, and you're young, and you're breaking in, and people don't think you're any good at what you do. The only time I'm ever competitive is when someone slights me. Otherwise, I'm not competitive. So for whatever reason, if someone's like, "You can't do that," or, "You guys aren't good enough," or... I remember this...

Jason Fried: Actually, early on in my career when I was a web designer, before I made software, I just designed websites, I submitted a website design to an award thing, and I'm trying to remember what... It might have been called the High Five Award or something. I can't quite remember what it was, and I can't remember the guy's name right now. Dave Siegel, actually, was his name. I do remember now. Back in the day, getting an award from Dave Siegel, I think, was his name, was a big deal in the design community.

Jason Fried: So I submitted a design, and he wrote me back saying, "You suck." Literally, "You suck. Find another day job." And I loved that. I loved that. That was like... I loved that. I love when someone says you can't do something, that you're not good at something, you know. Maybe this comes from being, like, I'm 5'7", and I'm pretty good at basketball, and you walk on the court, and people don't think you're very good. You know, I love that kind of stuff, right?

Jason Fried: So, that just fired me up. So as far as finding confidence, I think I probably had a lot of that early on, where people were like, "You're just one guy. How could you do this?" Or, "How could you do that?" Or, "You don't know what you're doing. You don't have a degree in this." That kind of fired me up for a while, but there's a point where you want... This is, again, to the point of, kind of like, you want to sort of launch, and then you want to find a place to settle, where you kind of just, I think, come into your own at a certain point. And I think I probably did that in my forties. I'm 51 now. So I think in my forties, I probably came into my own actually, settled into my own. Had some psychedelic experiences, which helped as well.

David Senra: Did you?

Jason Fried: Yeah.

David Senra: John Mackey... I don't know if it was in the episode, I can't remember.

Jason Fried: Yeah.

David Senra: But this guy keeps trying to get me to do psychedelics. I think we talked about it at the end.

Jason Fried: Yeah.

David Senra: I was like, "I'm not doing psychedelics." What did you do?

Jason Fried: Why not?

David Senra: I...

Jason Fried: Let's turn this interview around.

David Senra: Let's go. It's a conversation. You can do whatever you want.

Jason Fried: Yeah.

David Senra: I think me and you both bond over... Like, there are some positive things. Obviously, the tech industry and the Bay Area and San Francisco have created great companies and great products and stuff, but there's also a lot of just wacko shit, and a lot of them are...

Jason Fried: Sure.

David Senra: There's just too much drug use, in my opinion. I don't do drugs.

Jason Fried: Yeah.

David Senra: And I like the way my mind is, and I don't want it to change.

Jason Fried: Yep.

David Senra: And yeah, and I'm very resistant to doing drugs, because I've also had, like... My cousin died of a heroin overdose. My dad did drugs his whole life. He went to jail for selling drugs.

Jason Fried: Yeah.

David Senra: I've never seen somebody high on cocaine make a great decision.

Jason Fried: Yeah, yeah.

David Senra: So it's like, we carry all the stuff that we experienced earlier, and I'm like, "Well, what's the opposite of that?"

Jason Fried: Yeah.

David Senra: The opposite of that is not doing drugs. So, I'll just not do drugs.

Jason Fried: Yeah.

Jason Fried: I'm not here to convince you to do drugs.

David Senra: No, no, go for it.

Jason Fried: For me, the experience was very... Okay, as I think I mentioned earlier, my favorite thing in life is to have an insight, and so psychedelics for me were an avalanche of insights, and that was fascinating to know, that my mind could see things and understand things in ways I didn't know were possible. I could see, like... This will not make any sense, but maybe people who've done this will understand. You think of an idea, and I never thought an idea was like a three-dimensional object that I could turn around and see from the other side. Not like a different perspective on an idea, but literally, I could turn it around and see what was behind it. Things like that, like, that fascinated me. Having insights about the nature of existence and all this other stuff was fascinating, too, but just having... I remember... I've done this a few times, and the experiences are always like, "Wow!"

Jason Fried: Like, while I'm doing it, like, "Wow, I never thought about it that way," or, "I've never seen it..." So for me, it's candy, and this sounds like maybe candy and drugs, I don't want to mix them, but there's a sweetness to having an insight that you've never had before about something that you think you knew, that psychedelics have shown me. But I don't do "drugs."

David Senra: But it's an insight of...

Jason Fried: I've done this three times.

David Senra: How does it help you know yourself better?

Jason Fried: Well, that's not why I did it.

David Senra: Okay.

Jason Fried: I don't think I know myself better, but I feel more expansive now that there's more than I thought I knew. Here's how I kind of thought about it afterwards. You have to picture an old car radio from maybe the '50s or something. An old pickup truck had a car radio with a needle, and you could move the dial, and the needle moves, right? Get the little glass window with all the channels, and you're in one of the channels. That's where you are all the time. You're in this channel, 95.7 is you. And psychedelics let me turn the knob a little bit and tune into something else that's always been there, but I couldn't hear that frequency. Like, it's amazing. And then if you look at a radio and you turn the knob, you're picking up things that are there that you can't hear until you turn the knob. That's what it was like for me.

Jason Fried: And how does it make me a better whatever or know myself better? I think all experiences help you know yourself better. So it's just a mirror and a reflection and a detail and a crumb that creates the pile of you. I don't really know. It's not like that was a huge breakthrough for me, but it was fascinating enough to do it a few more times and learn a few more things that were just fascinating. One thing I'll just share, it's a little bit of an aside, but again, it comes back to this object thing, and maybe this is me seeing how my mind works that way, because we talked about objects before. But I remember having this experience where I was just puzzling through this three-dimensional puzzle and being stumped by it, but enjoying the problem-solving. And then I finally, just...

Jason Fried: Again, this is conceptual and metaphorical and not so literal, but I turned it around and saw it from the back, and it was dead simple. And what it basically told me was, turn everything around. This is inverted. Everything's a lot simpler from behind. Everything's real. The back of things are real. The front of things are fronts. The back of things are real. So, what does that mean? How do I apply that?

Jason Fried: I don't try to apply that. This is not trying. It's just an insight and a revelation of, like, get behind something to really know what it is. Again, I don't constantly refer to this, but it's something that now I have that I didn't have before, and I'm very glad I have it. So that's part of that. It's just seeing through a different lens, and I'd rather have a few more lenses available to me, if I can, that are harmless. This is not heroin, cocaine, and that kind of stuff. But again, I'm not here to sell any of these things, and I'm not a doctor, and all the disclaimers, right?

David Senra: I know. Yeah.

Jason Fried: But I would say it was a very worthwhile experience for me.

David Senra: Did you read Rick Rubin's book, "The Creative Act?"

Jason Fried: Yes.

David Senra: Do you think about things similarly to him?

Jason Fried: Yeah. When I read that book, I was like, "Did I write this book?" Not like, really.

David Senra: Yeah. Okay.

Jason Fried: He wrote the book. But you know what I mean? Like the...

David Senra: I just read it, just did an episode on it.

Jason Fried: Yeah.

David Senra: And when I hear you speak...

Jason Fried: Yeah.

David Senra: He's just like, we live in a magic world. All that stuff's not... You have an intelligence that is not coming from your brain.

Jason Fried: Yes.

David Senra: The world is beyond your comprehension. You have to be comfortable with ambiguity and not knowing, and I just feel I hear that from you constantly.

Jason Fried: Yes.

Jason Fried: There's Taoism in that, which is not knowing, not trying, not doing. Like, the world just works somehow in some magical way that we don't fully know. And this isn't about getting metaphysical, actually. I actually want to kind of bring it back, but I do think that there's... This is part of the make-it-up-as-you-go philosophy of business, which is just kind of going a bit more with the flow of where things go.

David Senra: Mm-hmm.

Jason Fried: This is the squirrel. Like, there's something very honest and real about that that works to me, and so it's similar to what he's talking about, which is, like, things just happen. You don't need to know exactly why all the time, but feel into them and understand them and pay attention to them, and trust them, and trust your intuition, your gut. Like, I'm a fully intuition and gut-driven entrepreneur, and I don't even love that word, "entrepreneur." I make products. There has to be business around it. I run the business, but I'm gut and intuition-driven. I don't look at numbers. I don't care about the numbers as long as we're profitable, and I know there's enough blubber in the business, as we've talked a little bit about. To make...

David Senra: No one's going to get that.

Jason Fried: That's fair.

David Senra: You have to talk about the blubber. And then I want to get back to intuition.

Jason Fried: Yeah.

Jason Fried: Okay.

David Senra: And then we'll get back to Rick Rubin.

Jason Fried: Yeah, sure.

David Senra: You mentioned this point that your business should have some blubber. And it's very memorable. What does that mean to you?

Jason Fried: And I had not said that before until last night. The word "blubber," it just came to me, which is just like, I don't want to run a very tight-margin business where I can't make mistakes, or I'm afraid of them. So, I believe in cushy margins.

David Senra: Blubber.

Jason Fried: So we can screw up, and it won't matter that much. I mean, it can matter, obviously. Again, I'm not oblivious to the reality, businesses can go out of business. They do all the time. All of them do eventually, basically, at some point. We take risks. We don't put ourselves at risk, is kind of how I like to think about this. So, I'm willing to take plenty of risks, but I'm not going to do something that's going to bet the farm unless we had to. And if I'm at the point where I have to, I feel like it's over already anyway, frankly. I'm not interested in betting the farm. It's just not even that fun. I'd rather just have the farm and then not have the farm.

David Senra: So big margin of safety is the way you think about it.

Jason Fried: Big margin of safety.

David Senra: A lot of cash, high profit margins. You still pay attention to your costs.

Jason Fried: Yeah.

David Senra: Yeah.

Jason Fried: We pay attention to costs.

David Senra: Yeah.

Jason Fried: When we talk about cutting costs, like we just... David wrote this great article about how getting off the cloud is going to save us something like ten million bucks and whatever it is. And a lot of people are like, "Why are you putting in all this effort to save ten million bucks?" It's because it's our money, man. We don't have outside funding, and I don't want any outside funding. Everyone has wanted to give us money over the years. I don't want anyone's money. It's our money. We make money through our customers, through revenue. So we take very good care of that money, and we're careful with it, and we watch our costs.

Jason Fried: So again, if you want to stay in business, your only competition are your costs, which hopefully you want to stay in business. So these are the things that I'm paying attention to, and so I want to have margin. That's why we keep the company small. We don't spend money on marketing. We've spent some money on marketing over the years, but it's been a rounding error for 27 years. We don't waste money on stupid things. We just don't blow it on things. We just save it, keep it, and allow ourselves to make more mistakes elsewhere that we sort of enjoy trying and making. And so, I would not want to run a grocery store. I don't want to run a 2% or 1% margin business. And what's always blown me away is how many companies in Silicon Valley who are in the software business lose gobs and gobs of money.

Jason Fried: It's like the most unbelievable thing for an industry like Silicon Valley to lose so much money on the highest margin product in history, software, with no costs, nothing. There's nothing to software. It's bits. There are some data costs, but it's called basically zero, all things considered. And there are still companies that are blowing billions, have never made a penny. They're big companies that you know of, just blowing money. It just blows my mind. It seems so incredibly irresponsible to me, but that's just me coming from a small business entrepreneur mindset, I suppose. But I just don't get that world.

David Senra: So the blubber, if we're going to use...

Jason Fried: The blubber, let's get back to the blubber.

David Senra: The blubber helps you stay in business.

Jason Fried: Yeah, it's fat reserves. Like, you should have those. It's cool to have 6% body fat, but it's not a good thing to live that way for a long period of time. You need to have some... If you're stuck out in the wilderness for a while, you need to burn something, right?

David Senra: You're dead.

Jason Fried: So, we've lived through dot-com crash, 2008 stuff, COVID. We have fat on the bone. I think it's very important to have that and not just be at the bone. The other thing is that because we're an LLC, at the end of the year, whatever money is left over goes to the members, the unit holders, which are me, David, and then we have two other people on the cap table. And then also, 10% of our profits go to our employees every year. And it's based on seniority. Or actually, that's the wrong... It's based on longevity, not seniority. The two aren't the same thing. However long you've been here. So every month you've been... You basically accrue units, up to ten years' worth of units. At that point, you've maxed out your units, and we distribute profits based on that. So, it's not based on which role you're in.

Jason Fried: It's not based on the salary or your title. If you've been here for ten years and you're a principal software engineer making hundreds of thousands of dollars a year, your bonus, your profit-sharing bonus, is the same as someone on customer support who's maybe making 90 grand or a hundred grand, who's been here for 10 years. So, all that money goes to real people. It's real money, it's real cash. No options, no RSUs, no stock, any of that BS. I find almost all of that to be pretty much BS, unless you're a really well-established public company. Our bonuses are based on profits. We've been profitable for 27 years, and they're distributed every year, and they're meaningful. I looked this up before the show. About 20 out of the 62 people last year, or 2024, because we haven't closed the final books on 2025 yet, there were six-figure bonuses, and this is year after year after year after year. It's real cash.

Jason Fried: That's the beauty of a simple business, a simple cap table, an LLC, and sharing real profits. There are plenty of people in our industry, plenty of our competitors, which I'm not going to name, that hire a lot of people and promise them a lot of stock, and you look at the chart, and it's down and to the right. And I feel bad for those people because they were promised something they'll never, ever get.

Jason Fried: So getting back to real, I want to pay people with real money they can actually put as a down payment for a home, pay for the college education for their kids, go on vacation, sock it away, whatever they want to do. This is real cash on an annual basis, and this is all part of a good business with sound fundamentals that has high margins and high profits and is an LLC, so we can distribute it every year. We have to, in fact, you can't leave any money in an LLC. You can, but you've got to pay taxes. Anyway...

David Senra: I know.

Jason Fried: You know what I... Just so, there's some pedantic person watching, you know.

David Senra: The wrong show for this.

David Senra: I want to go back to Rick Rubin and you knowing yourself through this psychedelic experience, partially in your forties. Before you had that experience, what was your inner monologue like? Let's say, when you're running your business, you're 10 years into it, you're 35 years old at the time, did you have a negative inner monologue?

Jason Fried: No, I think I was just more aggressive. I don't know how I'm coming off. I try to be pretty steady.

David Senra: You're definitely not... No, you're like a soulful dude.

Jason Fried: Okay, good. Okay. Well, I don't know. Like, I don't know. Sometimes I have a scowl, and people think... I was probably a lot more aggressive...

David Senra: Yeah.

David Senra: No, it's not a scowl.

Jason Fried: Probably resting face...

David Senra: The kids call it RBF.

Jason Fried: RBF, oh, yeah.

David Senra: Resting B**** Face. You should see our photographer, Mike.

Jason Fried: Yeah.

David Senra: He sends me pictures of me, I'm like, "I'm happy!"

Jason Fried: You're like, "I'm happy!" Exactly. Yeah.

David Senra: There are so many times where I'm like, literally, we're having this conversation, and this is how I know I'm going to do this for a long time, I'm like, "This is so much fun."

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: "Can I do it again tomorrow?"

Jason Fried: Yeah, exactly.

David Senra: While we're talking.

Jason Fried: Yeah, exactly.

David Senra: But, like, my face just, like...

Jason Fried: I know. Yeah, anyway, I think I was more maybe aggressive, or I don't even... I kind of don't remember myself, actually. I'll just pull it back to something else, then I'll come back to this thing in my mid-thirties, perhaps. But we don't do post-mortems. I don't look back on things. I don't like to look back on things, actually.

David Senra: Jimmy Iovine sat in that exact same chair, and he said, "I have no rear view mirror."

Jason Fried: Yeah, but that's how I feel.

David Senra: No trophy room. No, just like...

Jason Fried: So you're like, "What were you like at 35?" Like, I don't... Probably more aggressive, but I don't really know. And I'll tell you why I don't like to look backwards.

David Senra: Yeah.

Jason Fried: First of all, backwards is a story you're telling yourself about what you remember about something, and it's probably not true, and it's probably perverted in a million different ways. And there are a million different things that have happened to you that cause you to be the way you were. And all the things, like, I don't know what any of them are, and the reason I don't like the post-mortems in business, and I know a lot of businesses do this, they launch something, they spend all this time and energy looking back on it, trying to figure out why it did what it did.

Jason Fried: And my general sense is you'll have no effing idea why it did what it did. You're going to find some reasons that you're going to believe, but had you done that again, it may have turned out differently. Who knows? One little thing could have been different, the world could have been different, the way you said something could have been different, who knows, right? If you want to find certainty, you're going to find it, because you'll convince yourself of it. I just don't have any interest in looking back.

Jason Fried: I'd rather learn by doing something again, making more things. So if you draw a line, people are like, "Well, you should learn from your mistakes." I'm not sure what you can learn from them, frankly. I think you learn from moving forward and doing something. You learn by doing. You can't redo what you did, you learn by doing. So if you don't like something that you did, and you kind of have it in your head, just don't do that again. Like, that's the learning. It takes one second to know that, and move on, and learn by doing new things. So, I don't like to look back. Now, that's not like absolving myself of things I'm not proud of. That's who I was when I did the things, and that's that. So, I'm moving forward.

David Senra: So, I want to pull up something. The reason I asked the question about the negative inner monologue, it's very common with a lot of people.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: And we've been talking a lot about Rick Rubin, and I love his answer to this, which it sounds like if I was going to ask you this question now, you would answer it in a similar way.

Jason Fried: Yeah.

Jason Fried: Okay.

David Senra: So, he was asked the question, "Do you have an engine of constant dissatisfaction, self-criticism, that I could have done better?" And his answer was almost near...

Jason Fried: Can I guess?

David Senra: Go ahead.

Jason Fried: I don't know what it is.

David Senra: Okay.

Jason Fried: You couldn't have done any different than what you did. Is that his answer?

David Senra: Very close. Yeah.

Jason Fried: Yeah.

David Senra: So, he goes...

Jason Fried: And I believe that to be true. Go ahead.

David Senra: This is what I wanted to know, how you look at this.

Jason Fried: Yeah.

David Senra: So, I was going to ask you to answer that question next.

Jason Fried: Yeah.

David Senra: So he goes, "No, I'm pleased with the work that we did, excited to keep working. It's fun." You've said this multiple times today.

Jason Fried: Yes. Yeah.

David Senra: "I don't know what else I'd do with myself. I like making things. It's fun."

Jason Fried: Yeah.

David Senra: That sounds like you again.

Jason Fried: Yeah.

David Senra: "I feel like it's my reason to be on the planet, so I just keep doing it. If it could have been better, I would've kept working on it. If it could be better, it's not done. I've done everything I can to make it the best it can be. I can't do more than that, so there's nothing to be critical of. It's almost like a diary entry."

Jason Fried: Yes.

David Senra: It's very fascinating. "Everything we make is a reflection and a moment in time. Could be a day or could be a year."

Jason Fried: 100%. That's exactly how I see things, which is, I did what I did, I did the best I could or the worst I could, whatever it is, it was what I did, and there it goes. Now what? That doesn't mean be an asshole to people, and just... You can be an asshole. Other people remember what you did, too. So, they'll remember what you did.

Jason Fried: So you want to just be a good, honest person anyway, but some people might hear this, that's why I'm saying this, some people might hear this and go, "Well, that's an excuse to just do whatever the hell you want. There's no ramifications to any of these things." There are ramifications to these things, but they are written in history, and that is that. I've always just tried to do the best I can. This is why... I'm going to tie this back to numbers. We don't have revenue targets, except for, like, I want to be profitable. I don't have sales targets, revenue targets, user targets. I don't have any of these things. We just do the best work we can.

Jason Fried: A target shouldn't make me do better work. I should do better work because of the pride I take in the work that I do, and the seriousness in which I take the work that I do, and the enjoyment in the work that I do. I'm going to do the best I can. That's what I do. That's all I can do. That's all I should be doing, and I don't need something to try to tell me that I could do better had I aimed for some target. The target is the work I'm doing now. That's the best I can do. So, fully on board. He said it more eloquently than I did, but that's how I've always felt about this stuff, which is why I don't like measurement. I just like the product. The product is the measurement, not the number of things that people have done it, used it, and whatever. It is what it is. The number, the money, is ultimately like the byproduct of making something good. It's not the reason to do it. People are in search of certainty all the time, and I think it's nowhere to be found.

Jason Fried: But it makes people very uncomfortable not to know why this happened, or... And by the way, I shouldn't say it's not to be found. If you're making widgets on a line, and the widget's supposed to have a circle in the middle, and all of a sudden the circle's off, you can trace that back to where the machine went offline. Like, you can figure out some of these things. Of course, if they're mechanical and you can track it all down, but most businesses are not mechanical in that way. They are a series of decisions, ideas, timing, market conditions, competitor conditions, perhaps, your mood on a given day, the way it rolled out, what other news was happening in the day the thing... Like, to try to pinpoint the answer and then to go, "Okay, now next time we know not to do or to do," and to feel like you now know something that you actually don't know, but to be so certain that you do because you've "figured it out," I think it's really dangerous.

David Senra: Is that why I've heard you say a few times that you don't think you could do Basecamp again today?

Jason Fried: Yeah, no way. No way. No way could I do it again.

David Senra: The amount of friends that I have that sold a company and just thought like, "I'm good at company building."

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: And then their second shot is not going well or ended in failure and really made them question who they are.

Jason Fried: Right.

David Senra: I think that's actually an important thing to say. It's like, maybe you don't know why it actually succeeded.

Jason Fried: Yeah.

Jason Fried: I think that's true. You don't know why it didn't work, and you don't know why it worked. I really think that's true.

David Senra: But people don't understand how devastating that is, where you sold a successful company... First of all, it's almost nearly impossible to build a successful company.

Jason Fried: Right.

Jason Fried: Yes.

David Senra: Just a tiny percentage of humans that have ever existed have been able to accomplish this goal.

Jason Fried: Lighting in a bottle.

Jason Fried: Yes.

David Senra: This is why I started one of the shows, because I want to celebrate the people that have done this and say, "Hey, if you want a role model, maybe we should... You know, people that build companies and products that make other people's lives better, those are maybe good people to listen to hear speak. They probably know some shit if they've been doing it for multiple decades."

Jason Fried: Yeah.

Jason Fried: Right.

David Senra: Turns out, they have a lot of wisdom, or they've acquired a lot of knowledge in that. But it's so devastating to have had that, and then in the case... I always think of Trader Joe's, because again, talk about different... Me and you bond over the fact that we want to make products that are different, where I'm not interested in making a me-too product.

Jason Fried: Yeah.

Jason Fried: Yeah.

Jason Fried: Doesn't need to exist. Yeah.

David Senra: He had a completely differentiated product. He loved it. He wrote this autobiography. It was very fascinating because he writes it... I would say 90% of the pages are building Trader Joe's. He clearly loves it. It's very difficult.

Jason Fried: Yeah.

David Senra: Just put his whole heart and soul into it. Then he gets scared, and he winds up selling it, I think in the 1970s, if I remember correctly. It may have been the '80s. Sold it because he was fearful.

Jason Fried: Yeah.

David Senra: Then lives another few decades.

Jason Fried: Mm.

David Senra: I think at least three, maybe four decades.

Jason Fried: Yeah.

David Senra: Like, a long time.

Jason Fried: Yeah.

David Senra: And the last 10% is like, "Yeah, I did some investing, I did some real estate, I did consulting." But then the last paragraph is, he's like, "I must admit something to my own self. I wasn't true. I regret selling."

Jason Fried: Mm.

David Senra: "Thanks for listening, Joe Coulombe..." I don't know how to pronounce his last name. I don't know how to pronounce anything.

Jason Fried: Yeah.

David Senra: I'll call him Joe Coulombe.

Jason Fried: Do it in a French accent, please. Do it in a French accent.

David Senra: But then he goes, you know, "Thanks for listening, Joe Coulombe." Book gets published, he dies the same week.

Jason Fried: Oh!

David Senra: Yeah.

Jason Fried: Wow, that's quite a story.

David Senra: And I always think about that when you're like... This guy's life, you could tell, is full of regret.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: Full of regret.

Jason Fried: Yeah. I know people like that.

David Senra: Yeah.

Jason Fried: And it tends to happen in your thirties, once you've built this big thing and sold the first thing, and you're like, "I'm loaded now and I'm going to...

David Senra: You have decades ahead of you.

Jason Fried: Decades left. And it's not arrogance, it's just belief, like, "Oh, I can do that again." And some people can. Most people cannot. Or if they can, they don't reach the same height. And so, they're jumping, and it's like if you try to jump a 100 times, you can't get to those first jumps because you're tired, and that's just what ends up happening. And so then, they might build something great, but they can't see the greatness in it because it's not as great as the thing before, and that's even more tragic, is that they can't see something that's still an incredible achievement, but it's not the same. And other people will see it as less than, and it's just a terrible outcome.

Jason Fried: I'm afraid of it, not so much now anymore. But David and I talk about this all the time, which is, we do negative visualization, and practice. So, like AI, what if this just changes the whole damn landscape, and soft SaaS is just dead in three years? Our answer is, "Well, we had a great run." Like, 27 years, amazing, and by that time, maybe 30 years. What a run.

Jason Fried: We should be happy and proud of that experience. Not like, "Oh, damn, that sucks that we're out of this now." More like, "We should be enjoying this, and I hope we sure did, because that's a rare and fortunate experience to even have that experience." But I wouldn't go and start another business after that. I would just do something else. I don't know what it would be, but I wouldn't want to try to do this again because I don't think I could.

Jason Fried: I don't think I could, and I think it's totally fair to admit, I don't think I'm good enough again to do what I did before. I don't have the stamina. I don't have the drive. I don't have the thirst and the hunger to build a brand-new software company from scratch again. I just don't. I would have the curiosity, but I know that wouldn't carry me enough.

Jason Fried: Probably early on, I was, again, more aggressive, younger, pumped, you know, it was the early days, and we were pioneers. There's that kind of energy that you have, that you just don't have again, and it's fine. It's fine. I think one of the great... I think it was Bob Dylan, being interviewed on 16 Minutes, and I think it was Morley Safer or something was asking him about songwriting, and he was saying something... I don't know if you've seen this quote, but it's great.

Jason Fried: He was reciting one of his great songs. I forget the name of the song or whatever, and he still has an incredible memory to remember these incredible lyrics. And he's like, "I used to be able to write music like that," or "writes..." I'm paraphrasing. "I used to be able to do that. There was a certain magic to that. I don't know how I did that. I know I couldn't do it again, but I can do other things now."

Jason Fried: And when I saw that, I'm like, "That is a mature..." I mean, he's in his 80s now. I hope he's mature. But that is a mature human being to go, "I could do that before. I don't really know how I did it. Somehow I did it. I can't do it anymore, but I can do other things." And I think that's important because if you identify as an entrepreneur and you sell your business, like, if your identity is tied up into entrepreneurship, you have to go start another business because you have to... There's continuity there, that you have to be that person again. And then if you, again, can't achieve the heights, you just feel like you're disappointment.

Jason Fried: I've seen this in friends who've sold businesses, and it's just like, it's so sad to me to see that in them, when they can't just see that what they did was incredible, in that moment. These are moments that you have. These are periods of time that you have. These are experiences you have, and that's what happened in that time. Actually, can I go back to psychedelics for a second?

David Senra: Yeah.

Jason Fried: I'm going to tell you a little story. I don't know if it's good or not, but it's meaningful to me. The last time I did... These are mushrooms, by the way. So, the last time I did mushrooms, I remember going into it, telling the guide I did it with, because I did it the first time, and I had this incredible experience to this one song. She was playing different songs, had this one song, that I had this experience where I just felt like I learned everything in an instant.

Jason Fried: The next time I did it, I'm like, "Can you play that song again at some point? I want to see if I have that experience again." And so she was like, "Yeah, maybe, we'll see," you know, whatever. And so, at some point, I was aware enough that she played the song, and I had no experience. It was blank and empty. And after the song ended, I broke out in laughter, and I go, "Of course, you cannot have the same experience again. You cannot have the same experience twice. You don't deserve the same experience twice. It's not even possible to relive something again.

Jason Fried: That thing happened then, and this is now. They're detached, they're separate, they can never be the same. And it was a wonderful thing. So, I've now used that with my kids. My kids are growing up. They're 11 and seven. I'm never going to have the experience with my 11-year-old again as an 11-year-old. Once he's 12, he's 12. I can't have that again. So, you have to really savor those things now, and recognize that they are what they are now, and you will never get them again, and don't be sad about that. It just is. And that's the kind of stuff that, like, those experiences that I had in those times, really, those are the things I carry with me, and hopefully do affect the way I move through the world now today.

David Senra: That's beautiful.

Jason Fried: Mm.

David Senra: When you were talking about selling a company, and then maybe your next company in this entrepreneur's life is not as financially successful or big, as well-respected.

Jason Fried: Right.

David Senra: I've never heard a great definition of "What success means?" And the best answer I ever heard to "What is success to you," actually came from Steve Jobs, and it was beautifully simple.

Jason Fried: Mm.

David Senra: It was like: "Did I make something I'm proud of?"

Jason Fried: It's good.

David Senra: Yeah.

Jason Fried: It's good.

David Senra: And that's the way I think about it, is like, for your podcast, you need X amount of listeners. It's like, no, did I make something I'm proud of?

Jason Fried: Yeah. That's great. I think that's great. The way I think about it is, would I want to do this again?

David Senra: The next day?

Jason Fried: Just this, whatever this was. Like, would I want to do it again? If the answer is yes, then it was successful. If I hurt myself, I wouldn't want to do that again. If I wasn't proud of what I said, I wouldn't want... It's the same thing, like, knowing what I know now, would I hire this person again? It's the same question. Would I want to do this, whatever I just did, again? If so, it's successful. And I think that that's enough of a definition for me.

Jason Fried: It's not about money, it's not about any of those things. It's like, "Would I want to do it again? Would I want to spend my time doing that again, playing replay?" And I know it wouldn't be the same outcome, but the experience of it would be different, but it would still be the same trajectory. I'd like to do that thing again.

David Senra: You were speaking earlier about humans' propensity to take something simple and make it complex. Even though we crave simplicity, we abhor complexity, we kind of trend in the trajectory of making things just more complex.

Jason Fried: Yeah.

David Senra: I don't know why, when you were speaking, this came to my mind, but one of my favorite podcast episodes ever was back in 2023, Rick Rubin interviewed Jimmy Iovine.

Jason Fried: Mm-hmm.

David Senra: And they talked about one of the first... Rick Rubin tells the story of the first time he met Jimmy Iovine. Jimmy is already a legend. He's 10 years older than Rick, so he was well-known, and Rick is there with some other music executive, and Rick plays him this song he just produced. And Jimmy said something that changed his life, or the way he thought about things.

Jason Fried: Mm.

David Senra: He goes, "Oh, I wish I could still make something that simple."

Jason Fried: Mm-hmm.

David Senra: And Rick's like, "What do you mean? I'm sure you can. You're better at this than I am. You have a lot more experience than I do. You've been doing this a lot longer.

Jason Fried: Yeah.

David Senra: Of course, you can make something simple." And the point was that you don't know what you don't know.

Jason Fried: Mm-hmm.

David Senra: And so, he made this beautiful, simple thing, and then you tend to think you need to add more things to it, and make it more complex.

Jason Fried: Yeah.

David Senra: Where Jimmy just, again, like, that's just the way he is when you're with him. He'll say one sentence, he just gets right to the heart of the issue.

Jason Fried: Yeah, it sounds like an incredible thing to have, like a skill to have, basically. Yeah, I think that is the trend, it is just to add more things, I mean, naturally. And part of it is because you feel like, "Well, people get bored of things, and so they have to kind of expand the things," or there's expectations to do more, and people put a lot of pressure on themselves as business owners, or they take money from the outside world, and they have to grow a certain amount because they have to return the investment. And all of a sudden, they've unmoored themselves.

Jason Fried: They've lost connection with why they started this in the first place. They're no longer running their own business. They're running someone else's business. They just created a job for themselves, working for someone else. That's what can happen when you've just taken the simple thing that you had, and added a layer to it, that just blows it up in a different direction. In some cases...

David Senra: It makes it worse.

Jason Fried: I mean, for some people, it makes it better, right? But I think for a lot of people, it makes it worse, because now you're on a track which you can't get off. There's only one outcome that works. This is optionality. Let me get into this. Like, my feeling, in general, is that businesses... Okay, the most important thing to me, in business, is independence, which is, profitability is also the same, actually, the same thing. As long as I make more money than I spend, I can stay in business. That's independence.

Jason Fried: Independence is also, no one can tell us what to do. We actually feel obligated to do things nobody would allow us to do. That's a thing, David, and I talk about all the time, like, "We should do this. No one would let us do this. Let's do it!" You know, that's like the exciting stuff for us, the stuff we're not supposed to be doing. That, to me, is just a big part of it, and I think what ends up happening is... This is so funny, because there's no dry cleaner who's raising VC money, right? There's no pizza shop that's raising VC money.

Jason Fried: So, most businesses in the world are not like this. But in my industry, a lot of people have an idea and go raise money. And the moment they go raise money, they've cut off almost every option. They think they've expanded their experience and their opportunities, but they've cut off almost every possible off-ramp outcome, because now they have to be a big business or they fail. That's it. That's one option.

Jason Fried: I mean, some people become very rich doing that, if that's what they want to do. But most people blow right through what would've been a good business, and is now not good enough for someone else. And once it's not good enough for someone else, that's got to be a s***ty place to be as an entrepreneur, thinking that you just gave up this thing that was actually a good business, but it's not good enough anymore. And you can't get more money. You built a business to raise more money. You built a business that needs more money. Now, you've got to lay people off. Now, it just falls apart, and it's just over because you have no options except one.

Jason Fried: I'm a big fan of optionality. We could go IPO. I don't want to. We could raise money. I don't want to. We could raise more money. I don't want to. We could sell to PE. I don't want to. We could quit. I don't want to. Like, these are all options that we have, and keep going for as long as we want, as long as the business survives. We can do that, right?

Jason Fried: That is gold to me, is optionality. And I'd like to see more people think that way, because I think it'll benefit them, and not cut themselves off when even they think there's this mirage that, like, "Oh, I got a bunch of money, and I can do anything now." No, you can't. You can do one thing: Build a big business. That's not a lot of things.

David Senra: I feel you're attracted to timeless things. You have two tweets. One of them just went viral, and it's related to this, basically craving simplicity of abhorring complexity.

Jason Fried: Hmm.

David Senra: One was about... Was it the design of a Rolex over time? Was it, that the brand of... It was some kind of watch.

Jason Fried: Mm-hmm. Yeah.

David Senra: Which brand was it?

Jason Fried: It might have been Rolex. I mean, there's a few. Could have been an Omega Speedmaster. They've just maintained the same design. Porsche 911, similar.

David Senra: But you were showing pictures from, I think, let's just say it was Rolex.

Jason Fried: Yeah. Yeah.

David Senra: Look at this Rolex design in 1960.

Jason Fried: Oh, yeah.

David Senra: Basically perfect, has everything I need, nothing I don't.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: Look at the updated version, whatever, 2010.

Jason Fried: Yeah.

Jason Fried: Yep.

David Senra: Look at all the other stuff they added.

Jason Fried: Right.

David Senra: Why are you drawn to the first?

Jason Fried: Well, I'm drawn to the first... By the way, I don't think the new one is bad. So, it's just that what attracts me is the purity of the first one, because that is the purest form of the idea. And I love ideas and insights. Someone had an insight to design a watch that looked like that. And then from there, everyone based their designs off of that initial thing. But there was a time when that was the first thing that looked like that.

Jason Fried: That gets me going. For example, you take a Rolex Daytona today, and you look back at the first one in 1963. To me, the one in 1963, not just because it's older, it's better, in my opinion, aesthetically. Because it's the purest form of the concept, of the idea. Everything else from there has been layered on because they need to sell more, they need to come up with a new version, a new model, and this is what happens. They couldn't still sell that first version. That's not the way the world works. You have to keep making new stuff, right?

David Senra: Purity is the word that comes to mind, "Purity."

Jason Fried: Purity and the pure idea, like the pure form of the thing.

David Senra: Interesting.

David Senra: Could you use the word essence or no?

Jason Fried: I mean, essence is part of it, I think. Maybe you could. What's the French word for essence? I want to hear you say it. "Essence." I don't know what the hell it is. But to me, it's purity. It's like, that's the beauty, is that this is the initial idea, this is the original concept, and this is the first execution of that idea in three dimensions, in a product. Actually, the gym I used to go to had some old Concept, getting back to the Concept2, old Concept2 rowers. And I, actually, really liked looking at the early ones. And then looking at the changes over the years, and in that case, the changes were more functional. Like, they used better materials that lasted longer and stuff. But the idea, the fact that this idea of this product that's so good today, was so pure back then, and still kind of the same thing just gave me... I'm more attached to the brand because of that.

Jason Fried: Like, they didn't just add stuff to add stuff. They added stuff that literally did improve things, not just to sell new models, but to... You could see the material changes. Meanwhile, a lot of things like watches and stuff, it's just like, new dial colors and new stuff just to kind of sell more.

David Senra: That's a great point.

Jason Fried: You know?

David Senra: You're adding to it, but you're not making it better.

Jason Fried: Right. There we go.

David Senra: So, that's the second viral tweet, where you kind of laid out this huge essay about smart electronics.

Jason Fried: Yes.

Jason Fried: Oh, God!

Jason Fried: My parents were visiting for a couple of months, so we rented them a house down the street, so they had some more room. They like their room. So, we rented them a house, and it's a brand-new construction house, so we're like, "Oh, it's nice. There'll be no issues," you know, no leaks and no issues. So we get in the house, and like most new construction, it's got digital shit everywhere, right? The thermostats aren't like thermostats that you can just turn anymore; they're like touch screens. And some of those are good, like Nest is good.

David Senra: Yeah.

Jason Fried: This doesn't have Nest. Nest is a great product. It's funny, because it's a great product based on the original Honeywell design, that Dreyfuss design, I forget his first name. The round dial. Nest just updated that because it's such a good design.

David Senra: Yeah.

Jason Fried: These are, like, rectangular and big and have the weather forecast on them. I'm like... Or whatever. But actually, the thermostats don't. That's the alarm panel that has an... It's like a huge iPad screen. Anyway, screens and screens, and everything's a touch screen. Everything's a big black glass thing with too much stuff on it, because you've got to fill up the screen. You can't just have a tiny screen, you got to have a big screen, and if you have a big screen, you put stuff on it, so you put stuff on it.

Jason Fried: The dishwasher couldn't be used the first time without an app to register it. So, my mom wants to do the dishes, but they don't work. She had to call the house manager guy. He had to come down. He's like, "Why doesn't this work?" He plugged it in, and "Oh, there's an app. I got to get an app." Like, what?

David Senra: You're adding, and not making it better.

Jason Fried: To do the dishes?

David Senra: Yeah.

Jason Fried: Exactly. Your insight is exactly right. Adding it, not making it better. The alarm panel is slow and laggy. The thermostats, they say a number on them, and you're like, "Is that the current temperature or the temperature I want it to be?" I changed the temperature, but then there's a schedule which I can't quickly, simply modify, because it's in this little menu structure with this little laggy UI, and you're like, "Does anyone use this?" The people who built this certainly don't have this in their house. There's no way.

Jason Fried: There's no way they have this in their house, right? This is not a product built by people who are using the product they're building. This is a product built to specifications. Someone imagined this. There's this... Whatever. I don't actually know how that happens. I'm baffled by how it happens. The TVs, you know, now... I'm not a Luddite old-timer thing. But you don't turn a TV on anymore, you boot the TV up, and it takes twelve seconds to get a menu before you can... Again, there were some things that were better before.

David Senra: Yeah.

Jason Fried: You turn the TV on, and the channel that you were on would be ON. That was good! It's amazing, like, you can't do that today. That's actually not even a possible thing. You turn it on, and you're back to some menu with all the options again. It's like, "How do we go backwards?" I call this the great regression.

Jason Fried: Thermostats have gotten worse. Nest, maybe, is an exception. I'll grant them that. Good product. A really good product. Big alarm panels, a lot of panels, a lot of third-party products with big glass screens, bad. Touchscreens, often bad. In fact, car manufacturers, with the exception of Tesla, because Tesla's is outstanding, but everyone else who put a bunch of screens in their cars, they're starting to move back to dials again and buttons again, because people are like, "This sucks."

David Senra: Mm-hmm.

Jason Fried: Software is hard, and a big piece of glass; there's no tactile feedback. I can't do it, and I have to look at it. There's no muscle memory, because I'm not sure I'm just confirming what I'm doing. Like, these are bad things. So, the technology can get worse, and then it can slide back, and hopefully, it can get better again, and new lessons can be learned. But it was a revelation to me to go into a new home with the state-of-the-art stuff, and see how backwards it was. And I'm in technology. Again, I'm not a Luddite. I'm not afraid of this stuff, I get it. But to see how bad it's gotten, like the light switches, literally...

Jason Fried: When we rented the place,  my agent, who found it and whatever, and did the negotiations and stuff, he's like, "Hey, they want to do a walk-through with you." And I go, "Cool, I'll be there tomorrow." And I thought the walk-through was going to be just like, "Here's the house," but it was like, "No, here's how you use the lights." You're like, "I have to... What? What?" The best interface ever, was the switch. It works.

David Senra: It's ON, OFF.

Jason Fried: ON, OFF. Beautiful! It's almost like, the way I see it, it's like that has not been discovered yet, because, I mean, it had been, but then it had been forgotten. This is like an old technology from the Romans or something. Like, how do they build concrete so well? We still don't know today how the Romans built concrete so well that it lasted so long. Like, there's a lost art there. I feel like the light switch is a lost art. It's just gone. And it will be rediscovered one day, and people will be like, "Oh, my God, this is so much better than this damn technical shit," you know? There's a room and a place for all sorts of advancements, but there also are regressions. And it's unfortunate that the industry I'm in, is the one that tends to sell many of these to people.

David Senra: It makes me think of, again, I'm going to tie this back to Rick Rubin, since we've been talking about him a lot.

Jason Fried: Yeah.

David Senra: He has this concept of a ruth...

Jason Fried: Rick just has candles in his house, I'm guessing. He just doesn't... I don't know. I don't know.

David Senra: These guys are close with him. Ask him.

Jason Fried: Okay.

David Senra: But he has this idea of ruthless edit, and so he's like, "Okay, you made 30 songs for your album?"

Jason Fried: Yeah, yeah.

David Senra: He's like, "Pick the five that you absolutely can't live without."

Jason Fried: Yeah.

David Senra: Okay, so now we have a five-song album. It's a perfect album. Maybe he needs some more. So he's like, "But then we decide, out of the 25 left, before we add number six and seven, did it make it better?"

David Senra: Going back to, "You're adding to it, but you're not making it better."

Jason Fried: Yes.

Jason Fried: Yeah.

David Senra: I think the throughline here is, you see this timeless design of the 1963 Daytona.

Jason Fried: Yeah.

David Senra: And you're like, "There's nothing to add to it."

Jason Fried: Yeah.

David Senra: There's nothing else that's going to make it better, so just leave it.

Jason Fried: Yeah.

David Senra: It is perfect. I know you're a big fan of Porsche.

Jason Fried: Yeah.

David Senra: It seems like the silhouette, it's very similar.

Jason Fried: Yeah.

David Senra: In fact, here in Malibu, do you remember going up to PCH? There was that burnt-out...

Jason Fried: I do, yes. Yes. Yes.

David Senra: You could tell...

Jason Fried: Towards the Palisades, on the right-hand side.

David Senra: Yes.

David Senra: Exactly.

Jason Fried: Yes, yes.

David Senra: You could just tell...

Jason Fried: Why is it still here? But you knew it was a 911.

David Senra: You knew it was a 911.

Jason Fried: It's a 997, in fact.

David Senra: It sat there for a year, by the way.

Jason Fried: Yeah, yeah.

David Senra: But immediately, the other cars next to it burned out. I have no idea what it is.

Jason Fried: Yeah.

Jason Fried: Yeah, which model is that? Exactly.

David Senra: But that was just like, I know exactly what that is.

Jason Fried: Yeah.

Jason Fried: I know.

David Senra: And I think about that all the time. I think products, you should think about this. Jerry Seinfeld has this really interesting concept, where he says, "Dosage matters."

Jason Fried: Mm.

David Senra: And he's like, "You could go see a stand-up comedian, and 45 minutes in, you're like, 'This guy's great.' An hour and fifteen, you go, 'Eh.'"

Jason Fried: Yeah.

David Senra: It's like, he should have stopped at 45.

Jason Fried: Yeah.

David Senra: It's so hard. I guess the reason I'm bringing this up, it's so hard for us to stop.

Jason Fried: It is hard.

David Senra: To stop adding complexity.

Jason Fried: Yeah.

David Senra: To just sit there. When I asked you about timeless design, go back to Rick Rubin. What I love about him and that exchange between him and Jimmy Iovine, that happened probably 40 years ago, Rick would say, he's like, "Somebody playing the piano, just the piano, a piano and a beautiful vocal sounded great 50 years ago, sounds great today."

Jason Fried: Right.

Jason Fried: That's right.

David Senra: "It'll sound great 50 years from now."

Jason Fried: Personnel.

David Senra: So, when he tried to revive Johnny Cash's career, there's this great song called "Hurt," which I listen to all the time.

Jason Fried: Yeah, yeah.

Jason Fried: Yeah, sure.

Jason Fried: Yeah, "Nine Inch Nails."

David Senra: Exactly, that Trent Reznor of the "Nine Inch Nails," as a 21-year-old man wrote it, and he's talking about regret.

Jason Fried: Yeah, yep.

David Senra: And Rick's point was, like, a 21-year-old talking about regret is one thing. A 75-year-old man, when he can't go back and fix it, it's a way deeper cut.

Jason Fried: Right.

Jason Fried: Yeah.

David Senra: But his whole point is, like, "A great vocalist with a guitar sounded great 50 years ago."

Jason Fried: Always.

David Senra: It sounds great today. Let's just go back to the essence of what we're actually building, and I think, not many people building products... You just gave the perfect example.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: There's no essence there. They're not even using their own products.

Jason Fried: No. This actually ties into some other advice that Jeff gave us way back, right when we first met him, which was that, he told us to focus on the things in our business that don't change. He goes, "There's going to be plenty of things that do change, but make sure you focus on the things that don't change." And the examples he gave us said something like, "Ten years from now, people are not going to wake up and go, 'I wish Amazon's customer service was worse.' They're not going to wake up 10 years from now and go, 'I wish it took longer to get a product from Amazon.' They're not going to say 10 years from now, 'I wish Amazon's prices were higher.'"

Jason Fried: So, these are the core essence elements that he clearly invested in. Things are coming faster than ever. Another one is, like, "People aren't going to wake up 10 years from now and go, 'I wish I couldn't get this on Amazon.'" Like, more selection, faster delivery, great customer service, fair prices, even competing against other people and offering a lower price, even if Amazon doesn't sell it; these are the things in his business that he knew would never change, and he can still explore a whole bunch of other things, because they do a lot of other things.

Jason Fried: But don't lose sight of those basics, is something that he really instilled in us, and something we've tried to focus on. So, this is the essence, like, what is the essence or the purity or the core fundamental basics that really matter, and don't lose sight of those. Because it's very easy to lose sight of those, because they can become boring. Like, "I've done that for a while. Let's do something else," and you can kind of lose sight of that. Yeah.

David Senra: This is why I think people that have run companies for as long as you have are so rare, and it's why... If you look at the first few guests, I bet you, if you took off the average length of time the person has been working in their business, it's probably, like, 30 years. It's just like...

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: You said you like old people. People always say I'm obsessed with old people, which is funny.

Jason Fried: Yeah.

David Senra: But I'm just not obsessed with old people. I'm obsessed with people that do things for a long period of time.

Jason Fried: Longevity.

David Senra: This is where me and you will actually have a disagreement, where you're like, "I don't work hard."

Jason Fried: Hmm.

David Senra: Do you remember talking about this last night?

Jason Fried: Yeah, yeah, I do.

David Senra: And I was like, "Jason... Jason," and I was like, "We add it up."

Jason Fried: Yeah.

David Senra: So yeah, this is where I would argue that you work harder than most people that have ever lived. You just have spread it across 27 years. So, I literally pulled out my phone last night.

Jason Fried: You did.

David Senra: And I was like...

Jason Fried: Did the math.

David Senra: Yeah, you're like, "But I only work 40 hours a week." I go, "Yeah. 40 hours a week, over 27 years, whatever that number is, I think it's 54,000 hours or whatever the number is.

Jason Fried: Right.

Jason Fried: Yeah.

Jason Fried: Yeah, it's something like that. Yeah.

David Senra: And my question back to you is, "How many people have worked on the same thing for 54,000 hours?"

Jason Fried: Yeah. I don't know.

David Senra: Tiny.

Jason Fried: Yeah, I mean-

David Senra: Tiny amount.

Jason Fried: Probably.

David Senra: Yeah. I just like that you spread it across time.

Jason Fried: Yeah.

Jason Fried: Yeah, I mean, yeah, I suppose. I mean, again, it's, like, one day at a time, so it wasn't intended.

David Senra: You were laying bricks.

Jason Fried: I was just laying bricks. I just keep doing it. I mean, and then it just adds up, and the path gets bigger and adds up, and that's what happens. But yeah, I've always admired things that have stuck around for a long time. We used to have a podcast back in the day called "The Distance," which was a podcast that we did for a few years, of businesses that have been around for 25 years or more.

David Senra: I listened to it.

Jason Fried: And maybe that's not even that long, all things considered, but it's quite long for most. Yeah.

David Senra: No, that's incredible.

Jason Fried: And it was awesome, and most of these are family-owned small businesses. They just nailed some things and got them right, and I love businesses like that have been around for a long time. I'm not talking about us here, but there's something about, if it's been around that long, it's not a fluke. You can have something that's hot for a while, and it can go out. That's kind of a fluke, or a trend, or a fad, or something.

Jason Fried: But to be around for a long time signals that there's something, that is repeatedly right about this thing, right enough to stay in business for a long time. A lot of these businesses are tight. Like, you could have a dry cleaner, their margin's thin, and maybe it just is enough for them to get by. But they'd rather still be doing that than something else. And so, they're in it for a long time. It's not that it's a great business, but it's a sustainable business. And that, to me, is a great business. If they can keep doing that, there you go.

David Senra: Right.

David Senra: It's the same insight you had earlier with the leaf. You're like, "Why don't you look at this leaf, it has evolved forever."

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: Do you know who Mark Spitznagel is?

Jason Fried: No.

David Senra: I read his book called "The Dao of Capital," and this was probably, seven years ago.

Jason Fried: Hmm.

David Senra: He runs this hedge fund. I don't even know if he's still doing it anymore. But he has an entire chapter in that book on conifer trees.

Jason Fried: Uh-huh, yeah.

David Senra: He's like, "They're the tree that is present and can survive in the most extreme environments on Earth."

Jason Fried: Yeah.

Jason Fried: Yep.

David Senra: "They've been evolving for extreme time period," and he was drawing all these parallels between a great business that could survive, using the insights he derived from studying these trees, which I think is, is very fascinating.

Jason Fried: Yeah.

Jason Fried: Yeah.

Jason Fried: I love it. I've often thought of our business as an oak tree. I love oak trees. Oak trees are trees that I love.

David Senra: Bezos uses the analogy of Amazon as an acorn that grew into an oak tree.

Jason Fried: Hmm. I don't think about it as the acorn so much.

Jason Fried: That's cool, though, especially "A," "Acorn," "Amazon."

David Senra: Yeah.

David Senra: Mm-hmm.

Jason Fried: There you go, whatever. Wonder if he thought about Acorn as a company?

David Senra: No, it was...

Jason Fried: Never.

David Senra: You remember this. You're old enough.

Jason Fried: Yeah.

David Senra: The directories were in alphabetical order, like...

Jason Fried: Oh, yeah, that's why...

David Senra: Remember?

Jason Fried: That's right.

David Senra: Remember, there wasn't that many websites, so you could actually list them all.

Jason Fried: That's right, that's why he named it

Jason Fried: That's right. I remember that. I remember reading that.

David Senra: And he almost did, like, "Abracadabra."

Jason Fried: Hard work or something like that? Yeah.

David Senra: No, it's like Abracadabra or something like that.

Jason Fried: Yeah.

David Senra: And then people thought it was cadaver, and they're like ...

Jason Fried: Ah.

David Senra: It's like, that's not a good association.

Jason Fried: Funny.

Jason Fried: They don't sell cadavers there, do they?

David Senra: No.

Jason Fried: No, they don't. They don't. It's amazing. The "Everything Store" doesn't sell cadavers.

David Senra: Yeah.

Jason Fried: Okay. So, I've always thought about our business as an oak tree, which is like a... You know, oak trees are very stable. They can withstand a lot of storms. They don't grow very fast. They're actually quite slow-growing. Some are faster than others. But in the Midwest, where I came from, a bur oak is a very slow-growing tree, but it lasts a long time, can weather a lot of storms.

Jason Fried: And I've always found that to be a very appealing kind of tree to be, versus a cottonwood, which grows really fast, makes a lot of noise. Like, you can hear cottonwoods when it's windy. They make a big mess. Everyone notices them because there's cotton all over the place, and they die in about 75 years, or something like that. And they come down hard. It's just not as interesting to me. I don't need to be flashy. I don't need to leave signs all over the place that I've been here. Just going to be nice and quiet, build a great business, keep a solid foundation, add a little bit every year, so it just feels more stable, and weather storms.

Jason Fried: Over the years, in the tech world, there's a lot of... If something comes out, it's like, "It's a killer. It's a Slack killer. It's a Basecamp killer. It's a whatever killer." When you've been around for a long time, you see that played over, and over, and over. There's a lot of things that are killing, supposed to kill something else, but very few of them can withstand and outlive the storms that come. So, you can be hot for a while. But the hardest thing is just to stay around, to stick around. So people are like, "How do you compete?" Well, we just stay around longer than everybody else.

David Senra: Yeah, the line I have on this that's repeated over and over again in these biographies is, "You just stay in the game long enough to get lucky."

David Senra: There's going to be something that happens in year five, 10, 15, 20.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: Usually, an innovation invented by somebody outside your company, you can take advantage of.

Jason Fried: Right.

Jason Fried: Right.

David Senra: The example of this, like, Coca-Cola with refrigeration, they didn't invent refrigeration, but it drastically expanded their market.

Jason Fried: Uh-huh.

Jason Fried: Yeah.

Jason Fried: Yeah. Tobi! Tobi's interview with COVID, in a sense. Like, COVID saved Shopify in a lot of ways, right?

David Senra: He needed that difficult time period to then grow, and to realize all the things he was doing wrong, and he realized...

Jason Fried: Yeah.

Jason Fried: Yeah.

Jason Fried: And people were shopping online more, and all that stuff, too.

David Senra: Well, he had that huge spike in stock price, which he talked about, and then, it going down.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: But it's when he realized, "Oh, like, I'm cosplaying."

Jason Fried: Right, yes.

David Senra: "I'm a public company CEO, and this is what I do."

Jason Fried: Yes.

David Senra: He's like, "No! There's still..." I love what he said in the conversation where he's like, "There's not one right way to do something. There's probably 100."

Jason Fried: I believe that.

David Senra: "At least 100."

Jason Fried: Yeah. I think the way you did it, if you had to do it again, you'd do it the same way. But there are 100 different ways to do that same thing.

David Senra: I want to go back to what you just said, though, "Something can be hot, it can be a fad." The maxim I have for this is, "Time is the best filter." It's the only filter I trust for businesses, for ideas, for books.

Jason Fried: Mm-hmm.

David Senra: I usually read a lot of old books, but it works for people, too. Because a huge influence on my thinking is, like, Charlie Munger and his whole thing. It's like you need to build a seamless web of deserved trust with high-quality people.

Jason Fried: Yeah.

David Senra: And the only way you know if somebody's high quality is time.

Jason Fried: Yep.

David Senra: And him and Warren's case, they knew the same people for decade after decade after decade.

David Senra: I'm rereading the book "The Snowball."

Jason Fried: Right.

David Senra: It's the 700-page biography of Warren Buffett right now.

Jason Fried: Uh-huh, oh.

David Senra: And the amount of friends that he accumulates in his 20s, 30s, 40s, that are still around when they're in their 70s and 80s is absolutely remarkable.

Jason Fried: Yeah.

David Senra: For a business, time carries most of the weight, as another maxim. I got that from Munger because, when you read "Poor Charlie's Almanack," his thing is that you should master... There's only a handful of big ideas in all these different disciplines, so, you know, biology, physics, economics.

Jason Fried: Right.

David Senra: He's like, "And if you just master the big ideas," he says, "those few handful of big ideas carry most of the freight."

Jason Fried: Mm.

David Senra: And reading that and thinking about his... He prioritized durability in a business.

Jason Fried: Yes.

David Senra: And I was like, "Oh, so time carries most of the weight. You just have to survive, which goes back to your blubber, having a margin of safety.

Jason Fried: Blubber and small units.

David Senra: Yeah.

Jason Fried: That's a big part of it, too. This is a bit of an aside, but it's tied to it, and I think it's important to talk about, is pricing. So, with Basecamp, for example, nobody can pay us more than 299 dollars a month, okay?

David Senra: Mm.

Jason Fried: It doesn't matter how many users you have. So, you could be a big enterprise, and 299 dollars a month is the most you can possibly... Our prices go way low, but that's the most we allow you to pay us. Now, many of our competitors will be, like, "Hey, you want to pay us 50 grand a month? You got 2000 seats, we'll take it." I don't want their money, because what I want is a static group of customers.

Jason Fried: If you think about static, like an old TV, like the dots, they're all equal-sized. You should be able to pick out 10 random customers and lose... I don't want to lose customers, but if you could pick out 10 random customers and lose them, I think you have a good business. If you could pick out a 100 random customers and lose them and be okay, you have a good business.

Jason Fried: What you don't want are a bunch of outlier companies that you cannot afford to lose. You don't want customers that you cannot afford to lose. And so, by equalizing our pricing and not letting anyone pay us more than anybody else, we create a bunch of small units, which are individual customers, and if you take one out, it's not like Jenga, where the whole thing's going to fall. It doesn't matter in a sense, because everyone's essentially equal, no matter how big you are.

Jason Fried: And then we can develop software for the customer base as a whole, and not for a handful of customers that pay us a lot more than everybody else. And that's the enterprise game, is getting as many seats as you can, and landing these whales, and I just don't find that interesting. I also don't find it durable. Durability is about a lot of small things. And if someone wants to chip away at some of those, it doesn't matter because there's a lot more left. That's kind of what we were aiming for with durability.

David Senra: So, one thing that we haven't touched on, which I think is really important, we've danced around it a few times, you've mentioned it a few times, is that you are all intuition.

Jason Fried: Yeah.

Jason Fried: Yeah.

David Senra: I want to hear your thoughts on intuition, and I want to hear how you refined your intuition.

Jason Fried: I mean, intuition for me is just making decisions that you're comfortable with. I mean, and not look... Actually, you do want to look around, you want to pay attention to things, as many things as you can, in a sense. But ultimately, you have to be willing to make a human decision about something, and stick by it and stick behind it. I think these things, these decisions come from somewhere where you can't quite define where they're from. It's not like there's one thing that tips it over. Intuition, to me, is like a collection of a lot of things that you can't quite split apart, that lead you to make a decision. And that's how I'm driven.

Jason Fried: I go by gut, I go by intuition, whether it's a pricing, or a product decision, or a feature, or a new product, or a name, or whatever it is. We don't test things. We don't do focus groups. We occasionally A/B test for fun, but not because it matters.

Jason Fried: And that's it. Like, I'm not looking at numbers. I've never seen a spreadsheet that's ever made me do anything. I don't want to make a product decision because a spreadsheet told me to. That's just a thing, and there's a lot of other things that can tell me to do other things. I don't want to value this because it's a spreadsheet with numbers on it. That's just a thing.

Jason Fried: And so, I'm very careful not to put too much weight into something that purports to be more valuable than some other feeling I have, just because it has numbers on it. Now, of course, I don't want to do stupid things. I'm not going to throw 50 million dollars at a Super Bowl ad. Like, I'm not going to do that.

Jason Fried: So, your intuition has limits, too. But everything we do is based on just kind of what we want to do, what we feel. I want to feel into these decisions and go, "I feel good about this. No matter what happens, let's do it anyway." Yeah, that's what it is for me.

David Senra: How have you refined it over time?

Jason Fried: You just do things. You make decisions. I mean, to me, it's all about time under the curve, in terms of making decisions... Or area under the curve, sorry, I think is the actual correct way to phrase that. So, the more decisions you make, the more time you have, the more intuition you're refining. But you don't actively refine it. You don't practice intuition. You just make decisions.

Jason Fried: And the more you make, the more you make, the more it sharpens everything up. It takes the edge off, I think, eventually, as you make more and more and more, and you're tumbling these things around, essentially, you end up with a nice, smooth orb, and it feels really good to have that in your hand. And it feels right. And that's kind of where you want to get to.

Jason Fried: So, you want to have this place where, when you make a decision, you're like, "This feels like the right decision. I'm not afraid of this decision. I'm excited about this decision. It could go wrong, and I'd be okay with that, too. I just know that this is the decision I want to make right now, and I'm lucky to be in this position where I can make it. No one can tell me I can't." That's another part of intuition. Because you can have intuition that keeps hitting a ceiling, and someone else says "No," and then you don't get to use it. So, intuition has to be used, I think, to really be enjoyed. And that requires, again, back to independence, back to optionality as well.

David Senra: Jason, one of the coolest things about my job is that I can have somebody like you, that I've read and has shaped my thinking over a decade and a half. We've become friends, we get to hang out, and then you also get to come on the show, and then share all the things I love about you for everybody else. I really appreciate the time today, man. Just f****** awesome.

Jason Fried: It's been a blast. Thank you so much for having me on. It's really fun, yeah.

David Senra: Yeah, sure. Thanks for doing it.

Jason Fried: Yeah, you bet, man.

David Senra: I hope you enjoyed this episode. Please remember to subscribe wherever you're listening, and leave a review. And make sure you listen to my other podcast, Founders. For almost a decade, I've obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show, first found me through Founders.