David Senra - Jason Fried, 37signals (makers of Basecamp, HEY and ONCE)

Episode Date: February 15, 2026

Jason Fried is the co-founder and CEO of 37signals, the software company behind Basecamp, HEY, and ONCE. Fried is widely regarded as one of the most influential voices in modern product development, remote work, and business philosophy. He founded 37signals in 1999 as a web design consultancy, initially creating websites for clients while developing strong opinions about simplicity, clarity, and user-centered design. In 2004, the company pivoted to product development, launching Basecamp as a project management tool born from their own internal needs. The product's success led 37signals to transition entirely from consulting to software. Under Fried's leadership, 37signals became known for challenging Silicon Valley orthodoxies. The company remained bootstrapped and profitable, rejected venture capital, embraced remote work decades before it became mainstream, and advocated for sustainable growth over hypergrowth. In 2014, the company rebranded as Basecamp Inc. to focus exclusively on its flagship product, before returning to the 37signals name in 2022 as it expanded its product line. That same year, the company launched HEY, a reimagined email service, and later introduced ONCE, a new approach to software licensing that allows customers to buy rather than rent software. His accomplishments include co-authoring multiple influential business books with David Heinemeier Hansson: Getting Real, REWORK, which became a New York Times and Wall Street Journal bestseller, Remote: Office Not Required, and It Doesn't Have to Be Crazy at Work. Fried has been a prominent voice advocating for calm companies, reasonable work hours, and building businesses that prioritize profitability and sustainability over valuation and exit strategies. He writes and speaks extensively about product design, company culture, and the future of work, influencing a generation of entrepreneurs to question conventional startup wisdom. Show notes: https://davidsenra.com/episode/jason-fried Made possible by Ramp: ⁠https://ramp.com⁠ HubSpot: https://hubspot.com Function Health: https://functionhealth.com/senra Chapters (00:00:00) Build Products for Yourself (00:01:40) Low Costs, Small Company, Enough Customers (00:03:06) Your Only Competition Is Your Costs (00:05:25) How 37signals Stays Lean (00:09:43) Rewriting Basecamp & Fighting Software Bloat (00:13:42) Why "Enough" Beats Growth (00:17:44) Product People vs. Business Shells (00:22:41) The "So What?" Mindset (00:27:45) Staying Close to Customers (00:34:43) The Reward for Good Work Is More Work (00:39:57) Six-Week Horizons & Compounding Decisions (00:45:20) Anti-Fragile Business With Tiny Units (00:50:55) Galápagos Product Design (00:52:44) Radical Authenticity Over Marketing Tricks (01:27:39) Rick Rubin & Intuition-Driven Building (01:42:25) Lightning in a Bottle & Knowing When to Stop (01:50:29) Defining Success: Pride in the Work (01:53:58) Independence Through Profitability (01:59:23) When Tech Adds Friction Instead of Value (02:04:11) Ruthless Editing & What Never Changes (02:08:14) Longevity as the Moat (02:17:28) Building by Intuition Learn more about your ad choices. Visit megaphone.fm/adchoices

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. 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 like way back when 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 the stuff because I keep losing these things. So I made this product, which I eventually called audio file,

but I made it for myself. It was just this database, right? 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, like, I'll put a little text file in this archive of this software that said, if you like this, send me 20 bucks.

And I put up on AOL. So it's like pre-internet, right? Put up on AOL. And I got this envelope, actually an airmail. envelope. One of those with like the red and blue check marks, like old school like envelope from, and it's from Germany. And I opened it up and someone I printed out this piece of paper, which was the thing I included with the software and gave me a $20 crisp U.S. bill, right? And that was the moment I think 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, you. And then there'll be other people just like you. 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. 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. Yes, and this is all tied into like keeping your costs low. So, you know, if you have a lot of costs, high cost,

big company, you have to find a lot of people like you. But, But if you keep your cost low, keep your company small at the time, it was just me, you know, when I was doing the software thing. And I was making like, I don't know, 20 grand a year, like selling software as a solo person when I was like 16 years old or something like that or 17. Then I went into college a little bit as well. 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 like, you know, a few thousand people to pay me that money, 20 bucks, right, to get that eventually. But if I had a big business and I had a lot of money, you know, 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. So keep your cost 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. Like 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 like enough of a small world to like what I like and we're golden. You put it in a very interesting way. You said your real competition is your costs. Is that the line that you have?

Yeah. It's your only competition. Explain that. Well, like a business is very simple. You've got to make more than you spend. That's a business, basically. Like, I mean, you can keep borrowing money and then you can, you know, borrow more than you spend. And eventually you've got to make more than you spend.

So if you're making more than you spend, then you're kind of, you're competition is your costs. 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 they're going to do. You're going to do what they're going to do. You're going to 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 I can't 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

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. 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. 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, Andrew Carnegie, Rockefeller, like this, this theme reappears over and over and over again. It's one of the reasons why, you know, my main partner's ramp because they want to help companies control their costs. For sure. It was like the perfect alignment for the audience and what these, these history's greatest entrepreneurs are saying. But we were talking the other day where it seems very fascinating how, you know, you can have a software company and has insane margins, to lose money. Yeah.

And when I talk to these young founders, I'm like, just go study the early days of Microsoft. Yeah. It's like Bill Gates. The first, 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. First software company to get to a billion dollars in sales

of just pure software in a year. Yeah. But the first 30 employees of Microsoft were Bill Gates, his secretary and 28 programmers. There was no fat at all. No fat. That's something you talk about a lot. Can you talk about the importance of keeping cost low, small teams, and then you want essentially

like no fat anywhere? We have 62 people at 37 signals. And we've gotten as high as I think 80 at some point. And then we're about 63 or 62 right now, which is, feels really good. But we also built a lot of things when we were much smaller. We had like 12 people way back in the day or four 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. there's fewer, 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, like I want to avoid all of that. Get rid of all the things that get in the way of making good stuff. And I actually think too many people get in the way oftentimes and 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 working on a feature. One programmer, one designer. That's pretty much it. 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 that's 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. 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 software, 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. I just found there's no better way to do that than to keep the company small and tight. 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 pull back from that and go, we don't, that wasn't helpful. What did you not like about that?

But there's two people in the executive team, me and David, my business partner. That's it. We've had a CEO for a while. They were fine. They were good people. We just didn't. There wasn't enough work for them, frankly, to do the work. So they were doing things that they didn't 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 like 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. We've had like engineering managers and we found out again

that there was like too many levels in between David, who's the CTO and the people doing the work. He had to like 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. So we just, we tried those things. We had some things.

thoughts that maybe this would be a better thing for us to do, and it turned out, it turned out not to be a better thing to do. How long does it take you to realize a year? Okay. Basically. C-O-O 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 37 signals. 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. We look at numbers. and it's like one simple question. I always try to like, if I can, I always try to boil everything down to a question

that answers all the other questions. 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?

And so it turned out with the management stuff, 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. Does that work with products, too, or features of products? It can.

It's harder. You've rolled back people. You roll back entire products. Do you have a rollback features? We have done that in some ways. Typically, so every five, six years, we kind of reinvented Basecamp, which is our main product, our biggest product. Do you write it from scratch? We have in the past.

So from base camp one to base camp two was a total rewrite, from two to three was a total rewrite. Three to four was not and four to five, 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. And I'm always trying to make, 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, like, limits that push back on those expansions. It's like if this mug was burning hot, like 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. Like you look at this. If this thing was made of a really, really fragile material or something that would like melt if it got wet, you'd be like, that's a bad design. Like there's some things that are telling you this is a bad design. In software, you don't get that. 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 than 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. That's like the big challenge. And actually, frankly, like the most fun part of building products over the long term is can we buck the trend of having them slide downhill and instead like maintain or make them even better over time? Why is that fun? 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, it 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 like what it could be or what I think other people. think of it is, but like, what is this really trying to do? And it's fun to have these insights. So, like, my favorite thing in life, frankly, is to, like, have an insight. And I don't get to decide when I have them, right? No one does. You just, like, have one. 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 I 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. 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, like the shower and the software. 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 Kareem, who's the co-founder and CTO of Ramp. Ramp is the presenting sponsor of this podcast,

and Kareem is one of the greatest technical minds working in finance. today. Karim was obsessed with crafting a high-quality product and using the latest technology to constantly create better experiences for his customers. 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. In fact, Kareem 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. We were talking a lot about this conversation. I just with Toby Lucay. I know both you and I admire him. Oh, yeah. And what I love about Toby that you have in you as well is like, when you talk to him,

the next response out of his mouth is like not predictable. Yeah. And some of his like views are not correlated with one another, which also makes it really interesting. So like, for example, you've been running your company, started your company when you're 25. Yeah. You've been running for 27 years. Yeah.

You guys have been profitable every single year. Yeah. You have made, you know, 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. 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, like, 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, like, I don't like to plan. long-term plans. I like to make things up as I go. So that's all tied into that. But yeah, I don't particularly like business. I like running my business. Like I figured out how to run my

business. But the idea of me running another business, like 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 and the right ideas at the right time and all that stuff. That's what made this thing and continues this thing, 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 like, that's enough for me. I don't need to, like, 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. Like this, the 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 against serial entrepreneurship.

Like, it's boring to me. All that's boring. Okay, there's a million things I want to unpack there. You said a bunch of things. The serial entrepreneurship I want to hit on because you and I were talking about the conversation I had with John Mackey, where he was referencing some of his friends just love to like start. And you're like, oh, I actually have like this metaphor that I want to start talking about. And it is envelopes and letters.

Envelopes and letters. Yeah, and then we'll go back to the fact that you don't like business. Yeah. That you only like and you're not really important. Two, don't let me forget, is you have no sense of envy. Like, I know you well enough now to other people's businesses. Like, I don't think that is an act. No, 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. If any, you got to decide, if you 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, like, I don't have. What is the underlying thought there?

It's just like, 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. Like, I love what I've built.

It's great. I'm very happy with it. And it's a good fit for me. You know, 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. Like, we have ours. We do our thing.

We do our thing our way. And that's it. And if I had to do my thing someone else's way, it would just, 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. What is playing entrepreneur? to you? It means a lot of things to me, but I think there's a lot of people who, who, this is,

let's get into the envelope thing, because this is kind of part of that. Okay. And I remember when I was getting started being an envelope guy. So the envelope, to me, there's, 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? Like, it just, 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, and 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 like 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 gotta 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 gotta know who you are. I know I'm not an envelope person. I don't just wanna 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 sell it.

I want to just work on a 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 like nothing of substance inside that yet. 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 just kind of, it's repellent, actually. Why does it need to, you just use the word thin shell to describe the envelope. Why do you want a thin shell? Oh, what does that mean? Well, I would say this.

The more mass of 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, metaphors don't perfectly line up. But in my head, I think of like a thick business. It's hard to change. It's heavy. It's massive. There's, it's, there's too much distance between it and the customers, it and the product. There's space. Like, right? You can imagine, like, if you just imagine something very thick, this is the thing that matters. And you 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 try to build at 37 signals. It's a very thin business with a thick set of products that are good and solid and real and generate real profits and our real businesses. And then the rest of it is just enough to hold it all together. That's like 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. But it's mainly just to show people that like, 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. It's like, you know, there's the hockey stick, right, chart, right? That is like unappealing to me. I like more of like a metaphor where it's more like a rocket into orbit. So 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 maintaining. 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. 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 be trying to get to orbit year two. You've got to be like 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 like, why? I'm like, so what if you if you're massive and you're twice as massive? Like, so what? Why? Why? What's that all about? And they may have an answer for you. I don't. I don't know what they don't know what they're. would be other than like just growing for growth's sake. But I'm a big fan of getting somewhere and then

holding. When I think of you, I think one of your maxims that you repeat the most is that that idea. Like I hear you say so what all the time. Yeah, so much question. Yeah. Explain more about that. Well, you'd have to ask a question. That would be like, so what? I don't know. Like why grow? I mean, maybe that's not a good one. But for example, like we're definitely leading money on the table. I'm sure of it. Like, 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 like, so what? Like, 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.

I'm like, I don't want to fuck that up. I think people fuck 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 isn't, maybe there isn't. Maybe there's a way to optimize. Maybe there isn't. I just, it doesn't interest me.

So it's so what to that. I don't really care. Tell me if this observation that I have about you is correct. Yeah. You seem to have this inherent natural revulsion against optimization. Yeah, I don't like optimization. Okay. Actually, okay, so here's the consistency thing.

It's all about context. I don't like optimization around numbers. Like, I'm just picking, we can make $5 million on this. Well, it'd be amazing if we'd make $5.1 if we did X, Y, Z. I don't care about the X, Y, Z to make 5.1. But I am interested in optimizing a product to make it better. That to me is a worthwhile optimization. Like, it's better for me because I use it.

It's better for our customers because they use it. That's fun. But, like, squeezing out an extra $100,000 off $5 million or something, it's just, like, not fun. It's boring, not fun boring. Like, 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. That is the thing I'm here for, not to squeeze an extra $100,000 out of something. or an extra million onto something. I don't care. It doesn't matter. Like, 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 in 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. I don't even think you think of yourself as a C, and there goes to So what again.

You asked for it. I don't think you could help yourself. I don't think you think of yourself as a CEO. I don't. I don't actually even like you. the term, frankly. Okay. Like executive officer? What? Of what? Like, I make products I run the company with David. Dave and I run it together. Like, I don't need the CEO. How do you say, chief? Chief executive officer. Of what again? Like, of what? Like, 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. Like, 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 got to leave a little bit of room there for some humility. Like, we can always make better products. So I'm not going to call our products fantastic. 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 like 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. But I don't think of myself as a CEO. I would say whoever says it's not a good at use of your time. A lot of people say it, dude. Yeah, but like they need to listen to founders because they're all like this. The best entrepreneurs and founders in history, and I think what me and you bond over is exactly that.

Like, all they care about is products, I don't care about anything else. Yes. I think the way you think of yourself as a designer. Yeah. Is that correct? Yes. Sure.

Okay. It's a presumptuous. Like, I think of it, yes, fine. You're not a presumptuous person. I didn't mean it that way. I know you didn't. Yeah. But when I talk to you, it's like you've just designed everything in your life.

I like to make things. Yeah, but you just say that. But you put a lot of, there's a, you're a very thoughtful guy and you see the, like, 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. Yeah, as best I can.

I mean, I have a family and I have kids and, like, you don't always get, thanks the way you want them to be, right? But, like, 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. The best founders, I see this over and over again. You said something about, like, the thickness of the envelope and all this stuff that's between the person running the company and the customer. You have to make that a small, almost non-existent as possible. One of my favorite examples is this, this, this example for over 100 years ago, the found, Jim Casey, the founder of UPS. What he realized is,

like, he had all these executives, he paid attention incentives, he realized they would, over time, just tell him what he wants to hear. And so therefore, he was only getting, he's getting his ass kissed all the time, not getting used from information. So he's like, forget this. I'm not, I don't want to talk to them. Yeah.

He would have, 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.

He spent all his time talking to the person that's actually doing the work for the customer. So I don't think, they know the most. I don't think anybody saying, Jeff Bezos,

I know he owns, he's a partner is your, of yours, you know, it's a percentage of your company. You know, he railed about this forever. Right. And he made every single executive, you'd have to spend a day or a week or a month on support. Or whatever.

On customer support. Yeah. We do the same thing. We haven't done that for a bit, but we used to do that. We should do it again, actually. We used to have this thing called everyone on support where people 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. I think, you know, there's a, there's a, there's a, when I lived in Chicago, there was a grocery store. on the street called Olivia's. There still is. And I 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. Like,

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. Like I could walk past on the street. I could walk past 75 of our customers in 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. 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 Base Camp, the first thing you see is a letter from me with my email address, 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 it 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. 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. And there's no other way to do this. 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 has been there for 40 years. I love the local grocery store. I just love businesses. Those to me are so much more interesting than the billion dollar whatever. Why? That's a great question. I feel like, I feel like they're more real. I like real things.

For whatever that means, I define it however you like. But a business. A big thing, a big thing. A big, billion dollar business or a 10 billion dollar business just 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 clean to bring it up I pick it up from the person who owns the place This is her living is what they do There's something for me that I connect with something that's real That I feel like I can hold in my head and I can I can understand I keep coming back to this well not keep but I have already in this interview once let's idea of surface area and like a business as an object.

I want to be able to see the whole thing, understand the whole thing, a massive entity with tens of thousands of people and billions of dollars and whatever. I just, I don't understand it. And that's maybe my own shortcoming or whatever. I don't really care again. Like, I don't need to understand that.

It's not my thing. But I just prefer smaller businesses. And that's, 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. So a business that can't be beyond a single person's comprehension, like you can understand. Dry Cleaner's very, you give this great story. I don't remember if it was one of your books or not. There was like this, you have like a love of craftsmanship that I get from your writing. And yeah, there's like a pizza place where it's like he will only sell,

is it the fresh dough and he has no. It's a sandwich place. Okay, sandwich. Can you tell this? When they ran out of bread, I'm not there. I don't know if they're in business anymore. They're in Chicago. Vinnie's, I think it was the name of the place on Chicago Avenue,

if anyone wants to look it up. Sandwich place, sub-Italian joint, you know, 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. They're not making, like, they're not anti-optification. Yeah, they could, I'm sure, get more sacks to bread from that.

It actually comes like in a sack, you know, like the big baguettes or whatever. And like, they just weren't out. They're done. And maybe usually it's like 2.30 or something. There's no hours on the door. They close when they close when they're done. for the day. I just, there's something to me very poetic and beautiful about that. And like, again, enough. It's this, it comes back to this idea of there's enough in that. They're done

for the day. It's enough. They sold enough. But he does that because they could sell more, but then where do you stop? But this is the thing, but it's the quality though, right? Because I mean, you're right. It is the quality too, but they could get more quality bread also. But there's the, okay, so where do you stop? Like, where does this end? Well, you could stay open until six, I mean, seven probably, we could do seven 30. Someone's at the door, we could do eight. Like, you could see how this doesn't end and how 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's, then you're so attached to it that you can see how this could expand to that degree. 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, like, 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, I just, 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, 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. Like, isn't that what this is about? Are you proud of how long that you've been able to stay in business? I'm not proud of it.

Like, I'm not, I didn't mean that, like, in a negative way. It's like pride is not a... Is it important? I feel fortunate. Is the time important to you? Like, 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 take the 27? I would take the 27.

Because I like to, but the money is a side effect of all of this, right? So all the money does, like Patrick, who you interviewed, O'Shaughnessy, right? Yeah. I love what he said about work. It's like, I think something like, I work so I could work more or something like him, right? The reward for good work is more work. There you go. It's to keep going.

Great way to phrase it. And so that's why 27 years is more interesting than 15. I like this stuff. Like 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. 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. Like, that's why I want to, 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. Like, there's great products all over the place. I'm like, wow, that's an amazing thing that someone made. Like, for example, one of my favorite product. is the concept to rower. Are you familiar with this? Yes.

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'd look at things, by the way. I looked at the products, not the companies. 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... I do this for people. If you can make a great product, you're probably an interesting person to talk to. 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 concept two is probably one of my favorite products of all time. The concept two, rower. Their bikes are good too, and they make a ski machine too, but the rower is like 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. It's roughly the same thing, every iteration, but slightly better. It comes in a big box, very easy to a set. It's a big machine, but it's very easy to assemble. The display is black and white LCD, not even LED, LCD with like 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. A shit, like it's

done, get some new batteries. Like, it just works. The buttons you press, there's no touch screens. The thing is reliable. It always works. It's incredibly durable. It does exactly what 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, like a paper clipped and a concept two, Roer. Like, hard to improve on both of those things. Like, 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. But I can still like 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. 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. I believe in being around for the long-term.

But I think the best way to do that is day by day, not like 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. I can plan like, what, 900,000 days in advance, but, like, tomorrow I can't figure things out if I don't have a plan.

Like, you can figure things out tomorrow if you can figure things out for the next thousand days. Explain how you plan day by day. There's no plan. I mean, like, we have a direction. So the way I think of it. about this, and this is like, again, another weird metaphor, perhaps. But I think of our business, and maybe me even, like, like I'm a squirrel. Okay.

Probably weren't expecting this. So you watch a squirrel run across a field. What does it do? Like, 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. 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. That was like 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 figured out as we go. We just figured out as we go on a day-to-day basis. Like the teams figure it out as they go. Like I kind of set or son David or someone sets like the target generally, not like financial targets, but like 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, happy to come in.

I'll review stuff as we go. But it's a bunch of course correction to get us there. 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 not, today's Thursday. just take Friday, five Fridays from now or tomorrow. I'd probably have a better idea of what might happen tomorrow than I do five

tomorrows or 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

on Wednesday. Like 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. 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. They're like, you seem to have something good going right now.

What does success look like, oh, five years from now? So you hate the question. I'm going to ask you, I'm going to ask what your answer is, and I'm going to tell you what my answer to that question is. I don't know. This is the answer. I don't care. So what?

So what? What is five? I don't even know five years from now. Like, what's a difference? Like, it's an interesting question because it's a directional question, but I don't care. I don't have an answer. My answer is boring. Just more of this.

Yeah, sure. I think there's very... I mean, that's essentially what it is. Until... 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, like, it's kind of a silly thing to answer or even to ponder.

So, yeah, I'm with you, which is like this. This is the answer, basically. I've read all your books. I've listened to almost all your episodes. We've shared a bunch of meals together. And I never even knew that you just did the day thing, too, because that's what I was like, I just feel, I was like, I try to make a good 24 hours.

And then I was like, oh, I like this day. So, like, I'll do it again tomorrow. And I had this line that I just said by accident. I was like, well, all a great life is, it's just a string of great days. So, like, all I'm focused on is just, let me make a great day. And I told you last night where it's like,

way I think about very similar to what you're doing or what I'm doing is like, I'm just laying bricks. And like 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. And so my answer to question is it's like this. Like five or sorry, I just want to be making more podcasts. I know I'm going to be reading books. I just want to be reading books. I just want to be reading books. I just want 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. Yeah. And I don't think I'm ever going to stop doing that.

So that's what this is. Yeah. Great answer. And if one day you decide you don't want to do this anymore, then you just change. That's where me and you start to separate a little bit. I don't know. I said if. There might be a time.

I'll jump off a cliff. I'd be very disappointed. Maybe that would be the thing you start doing. It's not going to have cliffs. I don't know. Well, with parachutes, hopefully. But I mean, you might find, you might find, you might find another interest in your life. 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. Like, then when he said, I'm like, yeah, I have always felt that way because, like, I'm into things now that I wasn't into 10 years ago. That I didn't know about 10 years ago. And so I'm hopeful for you that there's other things. too, even though you can do this too.

But like, who knows? Like, 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 like, okay. I can tell you don't believe me.

No, I don't believe you. Maybe we do this till 80, right? Hopefully. But, but, and I hope you do too, because you're damn good at it, right? But like, who knows? And it's like, it's okay. It's okay. This is why the whole idea of a five-year plan.

It's like 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 like in some ways tying it back to the thinness. You want to find tiny units. Find small units. So a day is a good small unit, right?

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. Like if tomorrow sucks because whatever happened and it, okay, it's behind you in 24 hours. It's over. Like versus big, huge decisions where you take eight months to think about it and pulling 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 like, it's so hard to make those calls. 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. It's like what you basically want then is enough good things, enough good units in a year, right? Not like 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. Small units, bricks, build that way. And I think that you just, you become like more anti-fragile, basically, in that way, you know, 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? Like, 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. Like, stop worrying about all the other things you can maybe do and just focus on the thing that you're doing and like make that work over and over and over and over as long as you want to do it. 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. 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. 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. Do you feel you have like a narrow aperture with the world? I feel like you're like... I don't. Okay. Well, actually, what do you mean by that, first of all? Like, what you just said? Like, why are you worried about all these other opportunities out there in the world?

Like, 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 destructive way by any means. Like, yeah, you just, you don't really care what other people in your industry are doing. You have like a narrow focus on. Yeah, I don't know if it's narrow or wide. It just is.

Like, I'm doing what I'm doing. And it doesn't matter what they're doing. How often are you like breaking, like paying attention to how other people are making their products? Very rarely. I don't actually want to pay attention to it. Why? I think what ends up happening is when 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, you tend to just, that's the way you think it has to be done or can be done.

You're not open to like alternatives because you don't see them anywhere. And then you get people, 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. I'd like to take inspiration, if I'm going to take inspiration from anything product-wise,

it's going to be outside my, it's the concept two rower. It's not another piece of software. I'm not inspired by their software. I like buildings. I like furniture. I like concept two. I like watches. I like other things outside of my world that I can sort of admire and,

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. Like, everyone's always like, how does that come back and help you build your business? Like, I don't know. I don't care. Why does it have to?

Why does everything have to come back to business? Like, why does everything have to influence your decisions? It's like, 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 you just become, like, I think if you admire a variety of different things and pay attention to different things and enjoy a walk in the woods. Like a few days ago, I was just, it's 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. Like, I'd rather look at that than a 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 look, go for a walk. I want to look at nature. I want to look at great furniture. I want to be in great architecture. Like, that fills me up in a way. I'm getting enough with 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. Tell me about your idea of Galapagos Island product design. I just, like, there's something really cool about islands that, like, I have evolved on their own. I just, like, I don't know. I've never been to the Galapagos. My wife's been.

She asked me if I want to go. I don't want to go. because it's too far, but I should have gone, probably. But actually, I didn't want to go, frankly, because part of that was it was too far. I also felt like, like, can we let it be? Although I, it's got to be, I mean, she loved it, and I'm so glad she went, and the pictures are incredible,

and it seems like an amazing experience. 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, think of us as the Galapagos, I don't think of us this way, really, but like, conceptually there's, I don't like to use the word the Galapagos Island of the software and just, 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 whatever else is doing. I'm like 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. Like, 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 a 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. Nothing works like base camp. 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 like enough for us. Even your landing page just look different. They're essentially a letter from you describing what the product is and why it exists.

Yeah, I wouldn't like I always try to build things that I would want to see. Like 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. So all of our, I don't do the design on the land. I work with our designer to do a lot of that,

but he's sort of a visual person there. But I do all the writing. And I want every word to land with meaning. This is again like thin, thick. I don't like thick stuff thin. Like how can I just get to the right point, but not be sterile? It's a problem sometimes when you get into the point

and you be sterile. So like 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.

The company is right. 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. Like, this is, 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 like 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 like connect with people in a real way. This is like a real person showing off a real product. This is a real person writing a real thing. My name's on it, my signatures on,

and my emails on it. Like we are who we are. We are. We represent ourselves as we are. We are not a corporate entity hiding behind a structure. We're not a CEO or we're a CTO hiding from our customers. We don't have a board. We're like, 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, you know, we open source most of our 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. I just want to be direct and clear with people. And like, hopefully they like that. And some people don't. Some people like, oh, you guys are too small. I can't trust you. Like, I'm not out to convince anybody of anything. Like, that's the other thing. Like, 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. Like, 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. Like, some people don't like it. That's totally fine. I get it.

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. It was, I can't remember the culture, but they would do rub. I'll tell you the story. I was in Wisconsin in this little town called Mineral Point, Wisconsin. Small little town, about 50 miles west of Madison. was wandering through this gallery. Strangely, like, it was this weird building. It looked like a junkyard inside. Like, you peered in. It's like, what is going on here? Something, and I saw

some, like, old man on 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, like, junk everywhere. Anyway, he comes out, and you're like, okay, this guy's a character. 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 collects 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 was looking, and I find them very beautiful.

They're very simply patterned and the colors are very vibrant and they're very interesting. And there's just, 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 just to try to figure out why. 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 noticed that they have a lot of errors on them. Like there's what I thought was an error. Like there's geometric shapes. So their rugs are very geometric. They're stripes, they're squares, their triangles, there are all sorts of different shapes. And a lot of them like weren't quite right. You know, you can look at a shape and go, it's not, they're trying to make a perfect triangle, but it's like not quite right.

And I asked them about that 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 he said to me, he said, you know, and again, I don't know. this is true, but this is what he told me, which is the Navajo, like, they don't see those as mistakes. They're just like a moment in time. And he related 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, like, you don't start back. You can't take that stumble back. It just happened. 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 like so lovely. And I've tried to do that with the things that I do. I mean, I don't like want to leave typos and stuff. Like that's not quite the same thing. But like if I make a mistake in a video or something or whatever, like I, whatever, that's what you would do in the real world.

So I'm comfortable with that. I've always found that to be very, just again, a very beautiful thing that like 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. 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. You know, all these companies, that's a very broad statement, all these companies. You know, like,

Everyone's afraid. Companies are afraid like that PR people and they can talk to lawyers before they publish it. 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. 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 I just find that to be, there's, again, a thinness or 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. 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 like 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. It's kind of how you're designing your company. Yeah. Perfect fit for us, for what we want and what we need. And again, getting back to the original thing, like how many other people are there out there like us? Enough.

That's the business model. This is exactly how I started doing the podcast. I think I'm drawn to that too. Like the, I think in people, not companies, right? And this is why I was drawn to podcast to begin with because you, 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.

Like, you can't hide who you are at that point. You're going to like the good, you're going to hear the mistakes. And I use the word endearing. And that's exactly how I feel for like some of the people that I admire. They're like, 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 like Napoleon's Maxim's on Founders, like episode 337, if I remember correctly.

Yeah. And she was like, 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, I'm like reading from the book. I'm like, I don't know what this is. I don't know what this is. I don't speak French. Like, so I'm just going to, I'm going to do this phonetically. But it was endearing to her that I didn't like, you know, look up how, like, act like I speak French or anything else.

Like, this is, I read books and I'm just guessing how this is pronounced. You're not putting on errors. Like, like, I guess like, 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 know, like, you watch TV news and it's like, the guy, like, uses the Hispanic accent for, like, some, you know, Spanish word. And you're like, that's weird.

Like, you're trying too hard. Like, just, like, you don't need to, like, 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. And it's like, but you see it all the time. It's like, just, I don't know what, I don't know how to pronounce French words either. Like, I'm not even going to try. I'll just say what I say and read it phonetically. And, like, you can even see.

say like I would even go like I don't know I don't know how to say this I do so yeah like I don't know what this is you're gonna laugh at me but this is what it what 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 story is not perfect French pronunciation like with seven words out of 5,000 it's like 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. Going back to you writing these letters for the landing page,

do you do it like Bezos, where they write it before the product is created? Or you're doing it after the fact? In the middle, usually. So like with Hay, I wrote one for Hay, which is our email service. And before we launched, before the product was even anywhere near done, I wrote the letter. I need to interrupt you. I was a fan of your writing. 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. 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 Base Camp's project management, and like I'm working by myself. 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, I'm going to buy that product. So I'm a proud subscriber of, hey, just because I was like, I got to give this, I got to pay you back somehow. 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. It happens so much.

And it's a cool. It's a cool way. This goes back to we identify with people, not companies. Yes, yes. And it's a cool way to purchase something. Like sometimes, like, 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 like months before Hay was done. And so I wrote this letter about, like, why email is a beautiful thing. And for the longest time, people have hated email because they despise it because the email has gone off the rails.

And like, we can bring it back on. Do you remember when you used to get an email from someone you loved or like your grandparent or like an old friend? Like, it's a wonderful thing to get an email from someone who you care about. The problem is that most emails now are like spam and sales and garbage and like meetings and shit. So I just got to this. Anyway, we can get into that.

But the point was to your question was like, I wrote that in the middle. I didn't know what the product was going to be yet. We're going one day to time. I didn't know what it was fully. Was that the why behind the product? How would you describe it? It was the love behind the product. Love.

Yes. Say more about that. Well, I don't want to get like silly about it because it's not, you don't really, it's not silly. I know, but like it's a different version of love. No, no, I love like highcasts. So I know exactly what you're talking about. No, I love them.

Yes. And the way, 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. Yes. That. You're not silly. It's not silly. No, I don't mean.

Yeah, I know. I know, but like, 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 to 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 not proud of the things that sustain the business, which are the products. And I just, I love getting them as right as I possibly can. And there is a warmth that comes to you when you're really. proud to share something that you're done with that you finish 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 there is love reserved for that for sure. So this is a love for the decentralized. I think I read, I remember reading this. You were talking about like if the actual creation of email is actually a miracle,

we've just kind of fucked that up. Yeah. It's amazing that anybody in the world can get in touch with anybody else. There's no, like, platforms. Like, 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, like, 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, like, connect to some other website. Same thing is true with basic email. 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 care. And so we care. I live in email sometimes. We don't, 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. Like, I want to use tools that matter to me. And if I'm going to spend most of my day in base camp, I want to make base camp.

If I can 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. Yeah.

It's a great thing. It's amazing thing. You just used the word tool a few times. Yeah. Do you identify with Toby Lucke, just like, I'm just a toolmaker. I'm just a, yeah, I'm a toolmaker. I make too, make tools. That's how you think about it.

Yeah, I don't make, I'm in the, so people 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, I'm not tech person. Like, I don't like that. I make tools. They just happen to be made a 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. design and conceptual ideas. And so, yeah, I make tools. We make tools. We make levers. It's just a lever.

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 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 to make progress.

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. named a bunch. You have a love of architecture we've talked about. Watches, cars, the concept rower. There, when you said, you know, you could change your mind, David,

maybe you're not podcasting in the future. What I know for sure is if I ever do anything else, it's going to be physical. Because the same phenomenon where, like, I barely look at numbers, I know you barely look at numbers, but it's just numbers on the screen. And those numbers happen to be big,

but like you don't understand that. Yeah. It doesn't feel it. I remember there was a Mark Leonard of Constellation Software did this podcast. He talked about one of his most fulfilling jobs he ever had was not, you know, starting and compounding, you know,

whatever it was, 50 million to 80 billion or whatever he's done with pure software. Yeah. It was, he was building stone walls. Mm. And even to this day, he said he could go, and I think he was like 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 out it's like, I did that.

That's bad. I made that. Yeah. Why do you draw so much inspiration from physical things? 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 it's 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. I just find it to be very fulfilling and,

and real to like 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 like the 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're just, they build into other things. I just, there's something about the. physical world to me that is just, we're from it. Okay, like we are it. We are part of it. Like 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 like fly in the air. You know, I just want to be

closer to things that are real. Not flying in the air is real too, of course, but you know what I'm saying? Like I'd rather walk somewhere. I'd rather drive. I'd like to be closer to the ground I've begun to collect, like, rocks that I think are cool looking. Oh, now you can move to Balibu. Are these rocks crystals? They're not crystals. I was going to save that in case you ask you. 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, you know, when you're coming up as a designer in the early days, when I was designing, like, identities, like logos and stuff, You'd go through these, like, logo books or like corporate identity books.

I think there was an organization called, I want to call it Brand, but maybe I'm wrong. Print, actually, 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 like color patterns and pallets and layouts. And like, I'm like, go outside. Like the best designs ever are right there. That leaf is the best it's ever been. obviously it's like survived and evolved this is a great thing and so i like if you want to find great colors look at a bird don't look at a book like look look look at a leaf right look at the ocean look look look look

look 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 whatever i have goosebumps right like for me whatever it is whenever i talk about this like it's just fundamentally real to me and I just love it. And like, 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. I don't think you love the screen. You said if you sell your business right now I do. If I, we never, let's get this. Let's get into this. Yes. You said if you sold your business, you're never going to use a computer again. 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. I, I, 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 like compute. I don't need to compute. Let me just close it and walk away. I have, again, like this isn't one of the,

the computers are some of the most, probably the most amazing tool humans have ever made. So like, yeah. I don't despise them, hate them, but I could take some time away from them, but I think time away from nature would bug me a whole lot more. If I couldn't go outside for a year, it bug me. Way more. You'd go insane. Yes. I jump off the cliff. I think people have gone insane. They have for sure. Right, exactly. So like, you know, I want to be out. I want to be out there. I think it's just wonderful. So the screen is wonderful, software is

wonderful. Computers are incredible things. And right now is like an amazing time for computers. Like one of the most amazing times since the web back in the late 90s or mid-90s. 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. You know, I don't know how. But that wouldn't pay my bills either. So I have to be practical. Like, I 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. The bills are taken care of. The bills are, but I still, I don't think you have to worry about that anymore. And I don't do it for that reason. I know you know. But, yeah, I mean, I still like, my point is, had I built stone walls for 27 years, I'm not sure where I would be. No, the bills would be piled out. My parents would be very sore for sure. Yeah, yeah, yeah, yeah.

One of the people I most hope to get on the show and I want to talk to is Christopher Nolan. Yeah. Have you ever, like, looked into his personal philosophy at all? No, I just like his movies. Okay, so there's something that me, you and him, I think, have in common. He, you know, he desires to live in an analog world. I'm almost positive. That's a direct quote.

it might be me summarizing, reading his biography. Yeah. And so if you think about the juxtaposition between like you make software, but you want to be on a hike outside. Yes. You know, you want to look at the ocean, right? Yeah. He makes some of the most technologically advanced films that have ever been created.

And yet he doesn't have a cell phone. Like, you can't get in touch with him. Love that. He's like email his assistant. He has tracked him down. He will purposely put himself into like a difficult position. So like he'll drop into a new city. Yeah.

He doesn't, no, he doesn't have a smartphone. So no GPS. He's got to go up. to somebody like, how do I get to the deli or whatever? If he wants you to be in his movie, like, oh, email me the script. He's not emailing his script. Right. Okay?

He is printing it out physically. Yes. Flying to you. Yeah. So I'm Christopher, Christopher, Nolan, and I want you, Jason, on my, in my movie. I'm showing up at your door. Yeah. Here's a script.

And you're like, great, I'll read it. I'm sitting here until you're done reading it. And then when you're done, I'm taking it back. Amazing. Amazing. And I'm cool. And I feel that exact same way where it's like, you know, You know, your entire product is delivered, you know, digitally.

Mine is too. But I like to read physical books. I like to be in person. I will not do a remote podcast. Right. Now I've got to the point where I won't even go on other people's podcast remote. I was like, no, no, like, let's go meet and hang out. I want to talk on the phone. If I can't be with you in person, I don't want to text you.

I want to live in an analog world. I just feel better. Yeah. Being outside, reading physical books, not looking at a goddamn screen. I'm with you, and what's important about that is not actually, 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 so a lot of people don't know what they 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. They make decisions they think other people would make. Like, 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 like, you don't need to pick sides. Like you can love digital and you can love physical. It doesn't, they're not, they're all the same thing. We live on this like speck of dust, you know, in space. Like it's all the same thing, right?

So it doesn't like really any of it matter, like 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. All of the founders and extreme winners that I have studied have this one trait in common. They have excessively high energy levels. If you're going to be the best at what you do, you need to maximize your energy and output. And that's why I've partnered with Function. I signed up for Function long before.

They were a sponsor of this podcast. And when you sign up, they ask you what your health goals are. And my response in all capital letters was maximum energy. Function provides access to comprehensive blood tests and other lab testing to help you improve your health so you can perform at your highest level. Function has made it easy for me to monitor and improve my internal health markers so that I feel at my absolute strongest. As a member of function, you get access to test over 100 plus best. biomarkers, from hormones to toxins to markers for heart health, inflammation, and stress. Function gives you a straightforward analysis of all your results, along with advice from expert doctors on how to improve things like your testosterone, your stress hormones, how to

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and you're designing it just for you. 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. I think probably more recently, frankly, than then. I don't think I, I think I knew what I liked like to do, but I don't think I, I'm not sure I still know fully who I am, but I, that's the big question, right? Like, who are we in the whole thing, right? I don't, I don't totally feel like I should,

no one should be certain about that. But I feel like I've come more to my own, actually, since getting married and having kids. Looking back on who I, maybe how I was, how I acted, how I was in the world. I'm glad I am who I am now, then who, I wouldn't want to be that person again. Why? Didn't you say you used to have, like, anger? I think I was, yeah, I was definitely, like, more of a punk, you know?

Like a young. I don't know. I think I probably resented things for some reason. I was sort of, I had a chip in my shoulder. I mean, maybe that's part, maybe that was good. Like, you got to prove yourself when you're getting, 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.

I, the only time I'm ever competitive is, is when someone slights me. Otherwise, I don't, I'm not competitive. So for whatever reason, like, if someone's like, you can't do that or you guys aren't good enough, or I remember this, 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 Segal, I think was his name, was like a big deal in the design community. So I submitted a design and he wrote me back saying like, you suck, literally, you suck, find another day job. And I loved that. I loved that.

That was like, I love that. I love when someone says you can't do something, you're not good at something. Maybe this comes from being like, I'm 5-7 and I'm pretty good at basketball and you walk in the court and people don't think you're very good. I love that kind of stuff, right? So that just fired me up. So as far as like finding confidence, like I think I probably had a lot of that early on where people are like, you're just one guy.

Like, 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. Like that kind of fired me up for a while. But there's a point where you want, this is like, again, to the point of like, 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 40s. I'm 51 now. So I think like in my 40s, I probably came into my own, actually, settled into my own. Had some psychedelic experiences, which helped as well. Did you? John Mackie, I don't know if it was in the episode, I can't remember, but this guy keeps trying to get me

to do psychedelics. I think we talked about at the end. I was like, I'm not doing psychedelics. What did you do? Why not? Let's turn this interview around. Let's go. It's a conversation.

You can do whatever you want. I don't, I think me and you both bond over like there's some positive things. Obviously, the tech industry in the Bay Area in San Francisco have created, you know, great companies and great products and stuff. But there's also a lot of like just wacko shit. And a lot of them are like, there's just too much drug use, in my opinion. I don't do drugs. And I like the way my mind is. and I don't want it to change.

And, yeah, and I just, I'm very resistant to doing drugs. Because I've also had, like, my cousin died of a heroin overdose. My dad went to, my dad did drugs his whole life. He went to jail for selling drugs. Like, I've never seen somebody, you know, high on cocaine make a great decision. So it's like, you know, we carry all the stuff that we experienced earlier. And I'm like, well, what's the opposite of that? The opposite of that is not doing drugs.

So I'll just not do drugs. I'm not here to convince you to do drugs. Go for it. I just, 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, like, my mind could see things and understand things in ways I didn't know where possible.

I could see, like, this doesn't make any sense. We'll not make any sense, but maybe people who've done this will understand. Like, you think of an idea. And, like, 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 that I've done this a few times. And the experiences are always, wow, like, wow. like while I'm doing it like wow that I never thought about it that way or I've never seen it so for me like it's just it's candy and this sounds like maybe candy and drugs I don't want to mix them but like there's a sweetness to having an insight that you've never had before about something that you think you knew that psychedelics have have shown me um but I don't do drugs but it's an insight I'm not I've done this three times. How does it help you know yourself better? Well, that's not why I did it. Okay.

I don't think I know myself better, but I feel more expansive now, that there's more than I thought I knew. Like, here's how I kind of thought about it afterwards. You have to picture an old car radio from maybe like the 50s or something. You know, like an old pickup truck had a car radio with a needle,

on 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, like, let me turn the knob a little bit and tune into something else that's always been there. But I couldn't, I couldn't hear that frequency. Like, it's amazing. And then you're like, 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. 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. Like 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 like, 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 like puzzling through this like three-dimensional puzzle and being stumped by it, but but enjoying the problem solving. And then I finally like just again, this is like conceptual and metaphorical and not like. 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 like invert. 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? Like I don't try to apply that. This is like not trying. It's just an insight and a revelation that, like, get behind something to really know what it is.

Again, I don't like constantly refer to this, but it's something that now I have, that I didn't have before. I'm very glad I have it. So that's like part of that. It's like it's just seeing through a different lens. And like, I'd rather have a few more lenses available to me if I can that are, like, 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?

But I would say it was a very worthwhile experience for me. Did you read Rick Rubin's book, The Creative Act? Yes. Do you think you're, you think about things similarly to him? Yeah, when I read that book, I was like, did I write this book? Not like really. Yeah, he wrote the book. But, you know what I mean?

I just, I just read it, just an episode on it. And when I hear you speak, I'm like, you're, he's just like, we live in a magic world. All this stuff's not, you have an, you have an intelligence. that is not coming from your brain. 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.

There's like Taoism and that, which is like not knowing, not trying, not doing. Like there's just, there's things. 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 like the, I do think that there's,

this is part of the date, like 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. 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, like, 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,

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 me, no one's going to get that. You have to talk about the blubber. And then I want to get back to intuition. And then I want to get back to Rick Broomin. Yeah, sure.

You mentioned this point. They're like, your business should have some blubber. And it's very memorable. What does that mean to? And I had not said that before until last night. The word blubber 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. So we can screw up and it won't matter that much.

I mean, it can matter. Obviously, again, I'm. I'm not oblivious to the reality. Like, 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.

It's 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, like 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. So a big margin of safety is the way you think about it. A lot of cash, high profit margins. You still pay attention to your costs. Yeah. We pay attention to costs. When we talk about cutting costs, like, we just, David wrote this great article about, like, getting off the cloud, it's going to save us something like $10 million bucks and whatever it is. And it's like, a lot of people are like, why are you putting an dollar's effort to save $10 million?

Because it's our money, man. We don't have outside funding. I don't want any of outside funding. Everyone's 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. Again, if you want to stay in business, you're only competitionary 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 you keep the company small.

We don't spend money on marketing. We've spent money some money on marketing over the years, but it's been a rounding error over 27 years. We don't waste money on stupid things. We don't blow it on things. We just like 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. 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. Like, there's nothing to software. It's bits. There's like some data cost, but like it's called basically zero, all things considered. And there's still companies that are blowing billions have never made a penny. They're like big companies that you know of, just blowing money. It just blows my mind. I just, it seems so incredibly irresponsible to me. But that's just me coming from a small business entrepreneur mindset, I suppose. But like, I just don't get that world. So the blubber, if we're going to use it. The blubber, let's get back to the blubber. The blubber helps you stay in business.

Yeah, it's fat reserves. Like, you should have those. Like, it's cool to have 6% body fat, but, like, 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? So, so, so, you know, we've lived through, you know, dot-com crash, 2008 stuff, COVID. Like, we have, 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, 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. 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 basically accrue units up to 10 years worth of units. At that point, like you've maxed out your units, and we distribute profits based on that. So it's not based on which role you're in. It's not based on the salary or your title. If you've been here for 10 years and your 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 100 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, no, like, any of that BS. I find almost all of that to be pretty much BS unless you're like 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, a 2024, because we haven't closed the total books on 25. There were six-figure bonuses. And this is like year after year after year after year. It's real cash. That's the beauty of a simple business, the simple cap table, an LLC, and sharing real profits. Because there's 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, you know, down into the right. And I feel bad for those people because they were promised something they'll never, ever get. 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't distribute it every year. We have to. In fact, you can't leave any money in an LLC. You can, but you got to pay taxes. Anyway. You know what I was. Just so like there's some pedantic person watching. The wrong show for this.

I want to go back to Rick Rubin and you knowing yourself through the psychedelic experience, partially in your 40s, 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. Do you have a negative inner monologue? No. I think I was just more aggressive. I don't know how I'm coming off.

I try to be pretty spanky. Definitely not. No, you're like a soulful dude. Well, I don't know. Like, I don't know. Sometimes I have a scowl and people think of, like, I was probably a lot more. No, it's not a scowl. The kids call it RBF. RBA. Oh, yeah. Resting bitch face. You should see our photographer, Mike. Yeah.

He sends me pictures of me. I'm like, I'm happy. You're like, I'm happy. Exactly. There's 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. Can I do it again tomorrow? Yeah, exactly. While we're talking. Exactly. So, but like my face just like. I know.

I think, yeah, anyway. I think I was more maybe aggressive or I don't even, I kind of don't remember myself, actually. Like, I'll just pull it back to something else. Then I'll come back to this thing in my mid-30s, perhaps. But we don't do like post-mortems. I don't look back on things. I don't like to look back on things, actually. Jimmy Avine sat in that exact same chair and he said, I have no rear of your mirror.

Yeah, that's how I feel. No trophy room. No. So you're like, more you're like a 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. First of all, backwards is a story you're telling you. 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's 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 do.

They launch something. They spend all this time and energy looking back on it, trying to figure out why it did what it did. And my general sense is you'll have no effing idea why 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. The time, who knows, right? Like, 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. I'd rather learn by doing something again, making more things. So if you draw a line, like people 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 I do. But I don't, it's like, that's who I was when I did the things and that's that. So like, I'm moving forward. So I want to pull up something. The reason I asked the question about the negative inner monologue. It's very common with, you know, a lot of people. Yeah.

And we've been talking about a lot of Eric Rubin. And I love his answer to this, which it sounds like if I had, if you were going to ask, if I was going to ask you this question now, you would answer in a similar way. 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. Can I guess? I don't know what it is. Okay. You couldn't have done any different than what you did.

Is that his answer? Very close. Yeah. And I believe that to be true. Like, go ahead. This is what I wanted to know how you look at this. So I was going to ask you to answer that question next. 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. I don't know what else I do with myself. I like making things. It's fun. That sounds like you again. Yeah. 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 have kept working on it. If it could be better, it's not done. 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. It's very fascinating. Everything we make is a reflection and a moment in time. Could be a day or could be a year. 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 knows. It was what I did. And there it goes. Now what? that doesn't mean be an asshole to people.

And like just, you can be an asshole. Like that people, other people remember what you did too. So like, they'll remember what you did. So you want to just be a good honest person anyway. But like this, some people might hear this. That's why I'm saying 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 have tie this back to numbers. Like 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. Like, 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. Like, and the seriousness in which I take the work that I do and the enjoyment in the work that I do. Like, 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 things that people have done it, that 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. And so, but it makes people very uncomfortable not to know why this happened. And by the way, I shouldn't say it's not to be found. Like, if you're making widgets on a line and like all this, and the widget's supposed to have a circle in the middle and all of a sudden the circle's off,

like you can trace that back to where the machine went offline. And like, you can figure out some of these things. Of course, if like the mechanical and you can track it all down. But like 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,

all the way it rolled out, what other news was happening in the day of the thing. 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 figured it out, It's really dangerous. Is that why I've heard you say a few times that you don't think you could start,

you could do base camp again today? Yeah, no way, no way. No way can I do it again? The amount of friends that I have that sold a company and just thought like, I'm good at company building. And then their second shot is not going well or ended in failure and really made them question

who they are. I think that's actually an important thing to say. It's like maybe you know, you don't know why it actually succeeded. 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. 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. Yes. Just a tiny percentage of the humans that have ever existed to be able to accomplish this goal. 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, like, listen to hear, speak. They probably know some shit if they've been doing it for multiple decades. It turns out they have a lot of wisdom or they've required 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, you know, because, again, talk about different. Me and you bond over the fact that, like, we want to make products that are different. Yeah. I'm not interested in making a Me Too product. Doesn't even exist. Yeah. He had a completely differentiated product.

He loved it. He wrote this autobiography. It was very fascinating because he writes it. you know, I would say 90% of the pages are building Trader Joe's. He clearly loves it. It was very difficult. Just put his whole heart and sold to it. Then he gets scared.

He winds up selling it. I think in the 1970s, if I remember correctly, I could get, might have been the 80s, sold it because he was fearful. Yeah. Then lives another few decades. I think three, at least three, maybe four decades, like a long time. Yeah. And the last like 10% is like, yeah, I, you know, did some investing.

I did some real estate. I did consulting. but then the last paragraph is like, he's like, I must admit something to my own self. I wasn't true. I regret selling. Thanks for listening. Joe Columbo, or I don't know how to pronounce his last name.

I don't know how to pronounce anything. I'll call him Joe Colombo. Do you have a front accent, please. But then he goes, you know, thanks for listening, Joe Colombo. Book gets published. He dies the same week. Oh, wow. That's quite a story.

And I always think about that when you're like, you know, this guy's life, you could tell he's full of regret. Yeah, full of regret. Yeah. I know people like that. Yeah. And it tends to happen like in your 30s once you've like built this big thing

and sold the first thing and you're like, I'm loaded now. You have decades ahead of you. Decades left. And it's not arrogance. It's just like 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 like jumping and like, it's like if you try to jump 100 times, like 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. 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 like practice like like what if this just like AI like

what if this just changes the whole damn landscape and like 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 of what a run like 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 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, like, 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 just, I wouldn't want to try to do this again because I don't think I could. I don't think I could. And I think it's totally fair to admit, like, 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. I had like probably early on. I was again, more aggressive, younger, pumped. You know, it was early days. Like, we were pioneers. Like, there's that kind of, like, energy that you have that you just don't have again.

And it's fine. It's fine. I have again. One of the great, I saw, I think it goes, Bob Dylan was being interviewed on 60 minutes. And they were, I think it was like morally safer or something. I was asking him, like, about songwriting. And he was saying something.

I don't know if you've seen this quote, but it's great. He was talking about, like, he was like, reciting one of his great songs, I forget the name of the song or whatever. And he's like, 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. 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. 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. So how I did it. I can't do it anymore, but I can do other things.

And I think that's important because, like, if you identify as an entrepreneur and you sell your business, like, if your identity is tied up into entrepreneurship, like, 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 can't, again, can't achieve the heights. Like, you just, you feel like you're a disappointment. I've seen this in friends who've seen. sold businesses in. 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, like, it's, 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? I can tell you a little story. I don't know if it's, it's good or not, but it's meaningful to me. The last time I did, these are mushrooms, by the way. So last time I did mushrooms. I remember going into it, telling the guide I did it with. I did it the first time and had this incredible experience to this one song. She was playing different songs.

Had this one song that had this experience where I just felt like I learned everything, like in an instant. 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 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 and 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, 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. I've now used that with my kids.

I'm like, my kids are growing up there, 11 and 7. Like, 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. Like, 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 on those times really, like, those are the things I carry with me and hopefully do affect the way I move through the world now today. That's beautiful. When you were talking about selling a company and then maybe your next company in this entrepreneur's life is not as financially successful, it's big, it's well respected, I've never heard a great definition of like what, like what success means.

and the best answer I ever heard to like, what is success to you? Actually came from Steve Jobs. And it was beautifully simple. It's like, did I make something I'm proud of? It's good. Yeah. And that's the way I think about it was like,

Dick, for your podcast, you need X amount of listeners. It's like, no, did I make something I'm proud of? That's great. I think that's great. The way, the way I think about it is what I want to do this again? The next day?

Just this, whatever this was. Like, would I want to do it again? If the answer is yes, then it was successful. Like, I wouldn't want to, 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 to. It's the same thing.

Knowing what I know now, would I hire this person again? It's the same question. Like, 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. 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. You were speaking earlier about like humans' propensity to take something simple and make it complex,

even though we crave simplicity. We have poor complexity. We kind of trend in the depth, the trajectory of making things just more complex. 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 Iveen.

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

He goes, oh, I wish I could still make something that simple. And Rick's like, what do you mean? I'm sure you can. Like, 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. Of course you can make something simple. And the point was that you don't know what you don't know.

And so he made this beautiful, simple thing. And then you tend to like, need to add more things to it and make it more complex. 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 like the heart of the issue. Yeah, it sounds like an incredible thing to have, like a skill to have, basically. Yeah, I think that is the trend. It is to 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 like there's expectations. to add 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 they've unmoored themselves they've lost a 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're now they just create a job for themselves working for someone else that's what can happen when you when you when you've just taken when you've taken the simple thing that you had and added a layer to it that just blows it up in a different direction. Like, in some cases, it makes it worse. I mean, for some people, it makes it better, right? But, like, I think for a lot of people, it makes it worse, because now you're on a track, which you can't get off.

Like, there's only one outcome that works. This is optionality. Let me get into this. Like, my feeling in general is that businesses, like, okay, the most important thing to me is 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.

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 like 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 is stuff we're not supposed to be doing. That to me is like just a big part of it.

And I think what ends up happening is this is like so funny because like there's no, there's no dry cleaner who's raising VC money, right? There's no pizza shop who's raising VC money. So most businesses in the world are not like this. But in my industry, like 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 in big business or they fail. That's it. That's one option. I mean, some people become very rich doing that, like if that's what they want to do, but most people blow right through what would have 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 kind of a shitty 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 like over because you have no options except one. 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 the PE, I don't want to.

Like, 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. Like, we can do that, right? 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 like this mirage that, like, oh, I got a bunch of money. I'm like, 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. You feel, I feel you have, you're attracted to like timeless things. You have two tweets. One of them just went viral.

And it's related to like this, this, you know, basically craving simplicity of abhoring complexity. One was about, was it the design of a Rolex over time? And they just started, was that the brand of, it was some kind of watch. Which brand was it? It might have been Rolex. It might have been, I mean, there's a few. Could have been like an Omega Speedmaster. They've just maintained the same design.

Portion 9-11 similar. But you were showing pictures from like, I think, let's just say it's Rolex. Look at this Rolex design in 1960. Oh, yeah. Basically, perfect. Has everything I need, nothing I don't. Look at the updated version, whatever, 2010. Look at all the other stuff they added.

Right. Why are you drawn to the first? Well, I'm drawn to the first. By the way, I don't think the new one is bad. So, like, 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. That gets me going. I just like, for example, like, 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 and they need to come up with a new version, and a new model, and this is what happens. Like, they couldn't still sell that first version.

That's like not the way the world works. You have to keep making new stuff, right? Purity is the way, that's the word that comes to mind. Purity. Purety and like the pure idea, like the pure form of the thing. Could you use the word essence or no? 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. Assence. I don't know what the hell on this. But it's more about the, 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 concept two, old concept two rowers. And I actually really liked looking at the early ones and then looking at the changes over the years. And in that case, 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, like just gave me, I'm more attached to the brand because of that. 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 you could see the material changes. Meanwhile, like a lot of things like watches and stuff, it's just like new dial colors and new stuff just to kind of sell more. That's a great point. You're adding it, adding to it, but you're not making it better. So that's the second viral tweet where you kind of laid out this huge essay

about smart electronics. Oh, God. my parents are visiting for a couple months so we rented them a house down the street so they had some more room that's they liked the room

so we rent them a house and it's a brand new construction house so we 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 like the thermostats aren't like thermostats that you can just like turn anymore they're like touch screens and some of those are like nest is good this doesn't have nest like nest is a great project It's funny because it's a great product based on the original Honeywell design that Drifus designed,

if I forget his first name, the round dial. Ness just updated that because it's such a good design. 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, 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 got to fill up the screen.

You can't just have a tiny screen, you get up a big screen. And if you have a big screen, I put stuff on it. So you put stuff on it. A dishwasher couldn't be used the first time without an app to register it. So like my mom wants to do the dishes, like they don't work. She had to call the house manager guy. He had to come down. He said, why doesn't this work?

I plugged it in and, oh, there's an app. I got to get an app. Like, what? You're adding and not making it better. To do the dishes. Exactly. That is your insight is exactly right. Adding it, not making it better.

The alarm panel is slow and laggy. the thermostats are, like, they say a number on them, and you're like, is that the current temperature or the temperature I wanted to be? Like, I change the temperature, but then there's a schedule, which I can't quickly simply modify because it's like in this little menu structure

with this little laggy UI, and you're like, does anyone use this? Like, the people who built this certainly don't have this in their house. There's no way. 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, there's this, whatever. I don't know, I don't actually know how that happens. I'm baffled by how it happens. The TVs, you know, now, like, you know, and I don't, this is not like, I'm not like a Luddite old-timer thing, but, like, you don't turn a TV on anymore. You boot the TV up, and it takes, like, 12 seconds

to get a menu before you can, before, like, again, like, there were some things that were better before. Yeah. You turned the TV on, and the channel that you were on would be on. Like, that was good. Like, you actually, it's amazing. Like, you can't do that today. Like, that's actually not even the possible thing.

Like, you turn it on and you're back to some, like, menu with all the options again. It's like, how do we go backwards? I call this the great regression. Thermostats have gotten worse. Nests, maybe is an exception. I'll grant them that. Good product, a really good product. A big alarm panels, a lot of panels, a lot of third-party products with big glass screens, bad.

Touch screens often bad. In fact, car manufacturers, with the exception of Tesla, because Tesla 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. Software is hard in 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 it's confirming what I'm doing. These are bad things. So technology can get worse and then it can slide back and hopefully 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.

was. And I'm in technology. I'm not like, again, I'm not a lot of it. I'm not afraid of this stuff. I get it. But to see how bad it's gotten, like the light switches. Like, literally, when we run to the place, my agent who found it and whatever and did the negotiations and stuff, he's like, hey, they want to like do a walkthrough with you. And I go, cool, I'll be there tomorrow. And I thought the walkthrough 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? Like, the best interface ever was like the switch. Like, it works. On off. Beautiful. It's almost like the way I see it's like, that has not been discovered yet. Because it had, I mean, it had been, but then it always had been forgotten.

This is like an old technology from the Romans or something. Like, how do they build concrete so well? Like, we still don't know today how the Romans built concrete so well that lasted so long. Like there's a lost art there. I feel like the light switch is a lost art. It's just like gone. And it will be rediscovered one day. And people, oh my God, this is so much.

than this, like, 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. 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. He has this concept of a...

Rick just has candles in his house, I'm guessing. He just doesn't... I don't know. These guys are close with them, I'll ask him. But he has this idea of ruthless edit. And so he's like, okay, you made 30 songs. for your album. He's like, pick the five that you absolutely can't live without.

Okay, so now we have a five song album. It's a perfect album. Maybe it needs some more. So he was like, but then we decide out of the 25 left, before we had number six and seven, did it make it better? Going back to you're adding to it, but you're not making it better.

I think the through line here is you're, you see this like timeless design of the 1963 Daytona. Yeah. And you're like, there's nothing to add to it. Yeah. There's nothing else that's going to make it better, so just leave it. It is perfect. I know you're a big fan of Porsche.

Yeah. I don't, it seems like the silhouette has, it's very similar. In fact, here in Malibu, do you remember going up to PCH? There was that burnt out. I do, yes, yes, yes. You could tell. The Pals of the Palestinians. Yes.

Exactly. It was a, you could just. Like, why is it still here? But you knew it was a 9-11. You knew it was a 9-11? It sat there for like a year, by the way. Yeah. Yeah.

But immediately, the other cars next to have burned out, No idea what it is. Yeah, which model is that. Exactly. But that was just, it was like, I know exactly what that is. 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.

And he's like, you could go see a stand-up comedian and 45 minutes in. You're like, this guy's great. Hour and 15, you go, eh. Yeah. It's like he should have stopped at 45. Yeah. It's so hard. I guess the reason I'm bringing this stuff, it's so hard for us to stop.

It is hard. To stop adding complexity. Yeah. to just sit there. When I asked you about, like, timeless design, go back to Rick Rubin. What I love about him and that exchange between him and Jimmy Iveen that happened, you know, probably 40 years ago, Rick would say he's like, somebody playing the piano, just the piano.

And a piano and a beautiful vocal sounded great 50 years ago. Sounds great today. It'll sound great, or 50 years from now. So when you try to revive Johnny Cash's career, this is this great song called Hurt, which I listen to all that, 9-inch Nails. Exactly. That Trent Reznor of Nine-Ach Nails. as a 21-year-old man wrote it,

and he's talking about regret. 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. But his whole point is like, a great vocalist with a guitar

sounded great 50 years ago. It sounds great today. Let's just go back to the essence of what we're actually building. And I think, you know, not many people building products. You just gave the perfect example. There's no essence there.

They're not even using their own products. 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 were, it said something like 10 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 longer. 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.

So these are the core essence elements that he clearly invested in. Things are coming faster than ever. Another one's 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 the lower price even if Amazon doesn't sell it. Like, 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,

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 idea of what is the essence, this 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. 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 of the average, average length of time the person has been working in their business, it's probably like 30 years. It's just like, I'm upset. You said you like old people. People always say I'm obsessed with old people, which is funny. But I'm just not obsessed with old people. I'm obsessed with people to do things for a long period time. This is where me and you will actually have a disagreement where you're like, I don't work hard. Do you remember talking about this last night? Yeah. I was like, Jason. Jason. And I was like, we added up. So yeah, this is where, like, 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 up my phone last night. You did. And I was like, did the math. Yeah, I was like, you're like, but I only worked 40 hours a week. I go, yeah, 40 hours a week over 27 years, whatever that number is. How many, I think it's 54,000 hours or whatever the number is. And my, my question back to you is like, how many people have worked on the same thing for 54,000 hours? Yeah, I don't know. Tiny. Yeah, I mean, yeah, I mean, the amount. Probably. Yeah. I just, I like that you spread it across time. Yeah. Yeah. I mean, yeah, I suppose. I mean, like, again, it's, it's like one day at a time. So it wasn't, it wasn't an you were laying bricks. I was just laying bricks. I just keep doing it. I mean, and then it just adds up.

And the past 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 had burned off 25 years or more. And maybe that's not even that long, all things considered. but it's quite long for most. That's incredible. 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 that have been around for a long time. There's something about, 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, like, have something that's hot for a while and it can go out.

That's kind of a fluke or like a trend or a fad or something. But to be around for a long time signals that there's, something 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 can have a dry cleaner that their margins thin and maybe 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 like 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. It's the same insight you had earlier

with the leaf. You're like, why don't you look at this leaf that has evolved forever? Do you know who Mark Spitznagle is. No. I read his book called the Dow of Capital. And this was probably like seven years ago. 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. And he draws, he's like, they're like the tree that is present

and can survive in the most extreme environments on earth. They've been evolving for whatever extreme time period. And he was drawing all these parallels between like a great business that could survive

using like the, the insights he derived from studying these trees, which I think is very fascinating. I love it. I've often thought of our business as an oak tree. I love oak trees. Oak trees are like trees that I love. Bezos uses the analogy of Amazon as an acorn that grew into an oak tree.

I don't think about it as the acorn so much. That's cool, though, especially A, Acorn, Amazon, there you go, whatever. I wonder if you thought about acorn as a company. No, it was, uh, remember, you remember this? You're old enough. Like, the directories were in alphabetical order. Oh, yeah, that's why. Remember there's, there's right.

Remember there's, like, where there's that many websites, so you could actually list them all. I remember that. I remember reading that. And he almost did like abacadabra. Or something like that. It's like abacadabra or something like that. And then people thought it was cadaver. And they're like, that's like that's a lot of good association.

They don't sell cadavers there, do that? No. They don't. It's amazing. The everything stored and sell cadavers. Okay. So like I've always thought about our business as an oak tree, which is like, 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 like in the Midwest where I came from, like a burr oak is a very slow growing tree, but it lasts a long time, can weather a lot of storms. And I've always found that to be a very appealing kind of tree to be

versus like a cottonwood, which goes really fast, makes a lot of noise. Like you can hear cottonwoods when it's windy. They make a lot of 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. Like, it's just not as interesting to me.

Like, I don't need to be flashy. You don't need to leave signs all over the place that I've been here. It's 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. And there's been a lot of over the years. Like, you know, 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 base camp killer.

It's a whatever killer. Like, 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.

Yeah, the line I have on this that reappears over and over again in these biographies is you just stay in the game long enough to get lucky. There's going to be something that happens year 5, 10, 15, 20. Usually an innovation invented by somebody outside your company that you can take advantage of. Right. The example of this like Coca-Cola with refrigeration, they didn't invent refrigeration,

but it drastically expanded their market. Yeah. Toby's interview with COVID in a sense. Like COVID saved Shopify in a lot of ways, right? He needed that difficult time period to then grow and to realize all the things he was doing wrong. And this is, he realized. And people were shopping online more and all that stuff too.

Well, he had that huge spike in stock price, which he talked about and then the, it going down. Yeah. But it's when he realized, oh, like, I'm cosplaying. I'm like, I'm a public company CEO, and this is what I have to do. 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 a hundred. I believe that. At least 100. Yeah. I think the way you did it, if you had to do it again, you do it the same way, but there are a hundred different ways to do that same thing. I want to go back to what you just said, though, like, you know, something could be hot, it could be a fad.

The maximum I have for this is time is the only, like, time is the best filter. It's the only filter I trust for businesses, for ideas, for books. 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 that deserved trust with high quality people. And the only way you know somebody's high quality is time. And him and Warren's case, they knew the same people for decade after decade after decade. I'm rereading the book Snowball.

It's like the 700-page biography of Warren Buffer right now. 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. The time is the, for a business, time carries most of the weight is another maximum. I got that from Munger because when you read Portiawold Zominak, 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. And he's like, and if you just master the big ideas, he says those few handful of big ideas carry most of the freight. And reading that and thinking about his, It's the prior, he prioritized durability in a business. And I was like, oh, so time carries most of the weight.

You just have to stay, you have to survive, which goes back to your blubber, having, you know, a margin of safety. Blubber and small units. Yeah. That's a big part of it too. This is a bit of an aside, but it's tied to it. I think it's important to talk about is pricing. So with Basecamp, for example, nobody can pay us more than $2.99 a month. Okay.

It doesn't matter how many users you have. So you could be a big enterprise, and $2.99 a month is the most you can possibly pay. Our prices go way low, but that's the most we allow you to pay us. Now, maybe our competitors will, like, hey, you want to pay us $50,000 a month. You got $2,000 seats, we'll take it. I don't want their money because what I want is a static group of customers. Like 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 about 100 random customers and lose them and be okay, you have a good business. 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 Django or the whole thing's going to fall. Like, it doesn't matter in a sense because,

everyone's essentially equal, no matter how big you are. 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. 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. I want to hear your thoughts on intuition, and I want to hear how you refined your intuition. I mean, intuition for me is just making decisions that you're comfortable with. I mean, like, 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, these, these

things, these decisions come from somewhere where you can't quite define where they're from. Like, 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. 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. I don't, we occasionally A-B test for fun, but not like because it matters. And, and that's it. Like, I'm not looking at numbers. I've never seen a spreadsheet that ever made me do anything. Like, I don't want to make a product decision because a spreadsheet told

me to. That's just like 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 like a spreadsheet with like numbers on it. Like, That's just a thing. 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, like, throw $50 million at a Super Bowl ad. Like, I'm not going to do that. So, like, 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. How have you refined it over time? You just do things. You make decisions.

I mean, to me, like, it's all about time under the curve in terms of making decisions. So, or area under the curve, sorry, I think it's 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, like, actively refine it. It's not like you're, you don't practice intuition. You just make decisions. And the more you make, the more you make, the more it sharpens everything up. It's like 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 like 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. 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. Like, 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. Like, 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. Jason, one of the coolest things about my job is that I could have somebody like you that I've read and has shaped my thinking over a decade and a half. We become friends. We get to hang out. And then you also get to, you know, come on the show and then share all the things I love about you for everybody else. I really appreciate the time today, man. This is fucking awesome.

It's been a blast. Thank you so much here with me on. Yeah, sure. Thanks for doing it. Yeah, you cut in. 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-graced 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. Thank you.