📖 Read the full transcript of this episode
Founder and CEO of 37signals (makers of Basecamp, HEY, and ONCE) Jason Fried joins the podcast for a wide-ranging conversation covering software products and services, saying 'no' to millions, learning drums, and more. Jason shares his unique perspectives on building and running a hugely successful software company while staying true to his values.
Whether you're a tech entrepreneur or simply fascinated by the career of one of the industry's most unconventional and opinionated leaders, Jason's experiences and philosophies are sure to challenge and inspire you. Tune in for an honest and spontaneous discussion touching on the deepest questions in life and business.
00:00 - Introduction
2:20 - Inspiration Behind Hey Calendar
3:47 - Fantastical vs. Hey Calendar
4:55 - What Keeps Jason Going
7:24 - Why Hey Calendar Caps at $99
9:09 - Jason's Commitment to Independence
12:59 - Limits to Improvement and Acceptance
15:56 - Jason's Plans on Growing His Business
19:12 - Learning to Trust CEO Hires
20:59 - Why Jason Decided to Build New Products After 10 Years
24:21 - Changing Your Mind & Balancing Growth and Maintenance
28:06 -Keeping Businesses Simple
32:20 - What Jason Does With His Money
36:28 - The Courage to Close A Business
39:42 - The Burden of Wealth: Philanthropy and Responsibility
42:43 - Finding Joy in Spaces and Experiences
45:11 - Alternate Career Paths Jason is Drawn To
48:01 - The Future and Existential Worries
52:56 - Growing Old, the Younger Generation, and Life
59:27 - Things Jason Has Been Loving Lately
62:49 - Embracing Fiction: The Power of Storytelling
Twitter/X: @jasonfried
LinkedIn: @jason-fried
37signals: https://37signals.com/
Auto-generated from YouTube. May contain minor errors.
I've always been motivated by being pissed off at something frankly I got on the board and I looked at the budget and I saw that we're spending $10,000 a year on this software and it just pissed me off it was just like why is this acceptable so when you're 90 oh wait no you go to Peter Attia so when you're 100 and 110 when you're on your deathbed I'll be broke by then David and I and the rest of the company we make things we're makers we like to make new stuff and sometimes what happens is is that you come up with a direction or a strategy and you stick to it because you made the promise to yourself but then you end up cheating yourself because you're stuck to something you said in the past that was true back then but is no longer true so I feel like we're just we had to eventually be honest with ourselves again is there a fantasy of not doing what you're doing yeah was that too quick of a yes by the way yeah very very quick the industry that you and I are in it would be insane to think about closing a business that does tens or hundreds of millions of dollars in Revenue but there's this tiny part of me that thinks it'd be amazing just to close the business dude what's what's going on what have you been doing today well I recorded a podcast earlier with someone else which was good I'm just kind of trying to wrap up going a little quick trip up to a renovation project I'm doing up north a bit so I got every six weeks or so I got to go up for a day or two to review current work on a project and then come back what's your usual day look like these days are you busy are you chill been a little bit more chill although I'm about to get busy we're about to work on some new products so that's kind of a fun thing but it's been fairly chill this year so far actually I would say I'm trying to take a little bit more advantage of free time during the day because I've got kids and at night like it's basically right after work it's all family time and the weekends are actually not that open either so kind of during the day is sort of my open time of course I've got to work too but trying to watch that a little bit Yeah found having kids actually is a great forcing function like you can't really work after 5 there's no more late nights or anything and then if you stay up late working you're screwed cuz your kids will wake you up at 600
are you sleeping are your kids sleeping through now my kids sleep yeah they're 9 and five so they sleep through so nice I get to bed around 10 or so and then I get up at 6:37 it's kind of great a great setup for me actually it works out well but yeah for a long time sleep was not good you guys a couple years ago released hey which is a really awesome email client and then you guys just launched hey calendar I'm curious why launch a calendar product was that born out of like were you miserable and over scheduled and trying to come up with a solution or what prompted that I'm never over scheduled because I don't really schedule things I don't have a lot of stuff on my calendar I didn't really use a calendar very much before I used sort of just the built-in Apple calendar and then Fantastical was sort of the client that I used on top of that but the main reason we built it was because we had some new ideas around calendaring that were sort of bugging me about old calendars the way calendars had been built for many years digital calendars my wife has this huge she set up this huge paper calendar in our kitchen for our whole family it's better than any digital calendar I'd ever used kids could scribble on it we could put stickers on it like we could look forward to things it's like 10 days to Hawaii and there's like a countdown on each day and all these things that you're like why can't digital calendars do this and why on digital calendars does like a doctor's appointment I'm dreading have to be the same as a birthday party I'm looking forward to like they're just these bullet points with times you know and everything's treated like it's going to be a meeting it's like this is not how it should be and so I looked at this paper calendar and I go we can bring some of these ideas over to digital and then also email and calendaring kind of just go together they just do as the number one request we've ever had for hey so it made sense to bring them together and to do it in our own way
I haven't really played with it extensively but I'm currently on Fantastical so maybe I got to make this switch Fantastical is a great product it really is I used it for years and if you just want a really nice client on top of like a standard calendar setup it's a very very good thing if you want to explore like what calendars could possibly look like if you were to kind of want to explore a different approach and not look at everything just as like dots or grid lines and everything a grid being a grid and you want to have more flexibility with your time it's kind of a cool thing like the hey calendar has a literally a strip like a film strip style view where time never stops it's just like it's just day and the day moves slowly across your screen and everything's vertical and it's a really unique way to look at time that really does change the way you look at your day because you see open spaces we actually label the amount of open time you have and not just like the amount of the number of events you have but like you've got four hours between this thing or two hours between this thing and here's nighttime and you've got stars and the next day comes in the screen it's kind of a very interesting thing so it's worth checking out you had a tweet the other day that I that was really interesting so you you know you've for anyone that doesn't know you guys have built this huge software business over the last what 20 25 years 25 years yeah 25 that's crazy 25 years well 20 years in software we've been around for 25 years yeah and you guys were an agency before that and then you launched base camp so financially you've been incredibly successful built this huge business I would assume that you have enough money that you don't need to keep working you wrote a tweet about why you keep going and what drives you can you talk about that cuz it's not the usual thing that drives you're not talking about I want to buy the New York Mets or I want to buy a new Gulfstream or I want to give it all away this is a very interesting way of thinking about it yeah I don't want any of those things a Gulfstream would be cool I'll admit that that would actually be pretty interesting I've always been motivated by being pissed off at something frankly
I moved in this neighborhood a few years ago where I live today I just got on the board of the HOA like the homeowners association we've been using the software to like if a guest comes they get like a parking pass kind of thing because the streets are you know you need to have a pass to park basically it's just been like this miserable crappy piece of software it's fine in that it works but it's just everything about it you can tell like it was outsourced or no one cared there's just so many things you look at that and go there's just no way someone cared about this things are shoved into place there's weird gaps it's just like not carefully considered it was bad enough but it was again it was fine and then I got on the board and I looked at the budget and I saw that we're spending $10,000 a year on this software and it just pissed me off it was just like why is this acceptable it's not it's just purely not acceptable but of course the HOA like no one knows what other software exists they were probably sold this thing some guy came and sold them the thing and they're like sure this looks good we need something just this acceptance that like mediocrity is worth 10 grand it just pisses me off and so I've always been motivated to just make much better versions of things and charge very very fair prices for them like with Basecamp for example you cannot pay us more than $299 a month period you can have 9,000 employees we cap the amount you can spend at 300 bucks and for everyone else it's you know 15 bucks a user right now and historically it's been 99 bucks unlimited users so we've always kept our prices low hey's 100 bucks a year yeah it's more than free email but like you can't pay if you're a business you can't pay us that much more
I just don't like the idea of software being expensive is that because you're a good guy or is that because you and David don't want the hassle of administrating huge teams and dealing with Enterprise and sales and all that kind of stuff well I'll take credit for maybe being a good guy but that's not the main reason there's some of the latter which is we don't want to build an organization that would have to service an account that's paying us $65,000 a year and has 6,000 employees and account managers and customization and all that stuff there's a lot to it there's a lot to that that we don't want to do but I just don't think software needs to be expensive I don't understand why it is frankly I understand why a handmade piece of wooden furniture is expensive because like it took a lot of time and the materials and you can't make many of them at once I understand why a lot of other things are expensive that have really high-end materials and again can't be built at scale but if you can build something at scale typically price should be coming down at that level software is one of these things that you basically build once and you replicate a billion times for free I don't know it just always bugs me that something like that should be expensive it just shouldn't be so anyway that's one of the things that drives us but more than that it's not just the price it is the combination of first of all I just think solutions are still an unsolved problem in so many different Industries there's so many bad pieces of software that people just put up with and accept
and I see it like in my kids school like the educational software our kids are forced to use it's so bad I'm sure it's I know some of it's free Google gives stuff away for free and the Google stuff isn't bad but like the custom stuff that they these school districts buy is so bad so convoluted and I've seen the budgets and it's so expensive it just bothers me so we want to put amazing stuff out in the world that is fairly priced and reasonably priced and that drives me so I remember one time I came to you and I said Jason I'm doing this software company and I want to give you free shares in it I wanted your advice I just wanted to be able to call you and I said I'm going to give you I think it was like 3% of the company or something like that I sent you the docs the contracts and you just said I don't want to do a contract I don't want to deal with that just tell me that if something goes well you'll take care of me later obviously I really appreciated that trust but I thought it was really interesting that here's this thing and who knows what that's worth but let's say it's worth on paper $50,000 or something and you just went I don't like contracts I don't want to do this right that is one of the most fascinating things about you you more than any other entrepreneur I know you don't do stuff you don't want to do
and you've structured your life and your business in a way where you never have to do anything you don't want to do I admire that and I've taken a different approach where there are times where I do things I don't want to do and I often think of you and go man I wish I had Jason's situation where I didn't owe anyone anything I'm really curious is that an accurate reflection and where does that come from for you like what happened to you in your life that's important to you I Value Independence basically Independence for me means really like being truly independent which is the ability to do what you want to do how you want to do it and not have to answer to anybody else or have to ask for permission or any of those things and I think I just take that to not the extreme to be extreme but like I really take advantage of Independence I'm financially independent at this point so like I don't need 3% of your company like I kind of also don't want 3% of your company I just want to help you because I like you we're friends like I just want to help I don't need the financial ties to it I don't need the obligation to it I don't like to mix up that way I've invested in your company and I've invested in other private companies but I don't need to be given anything if I'm going to get something back I want to put something in basically it's another side of that too and I don't think advice frankly is that valuable to trade for 3% I mean I appreciate that it's very generous but I it almost doesn't feel like a fair deal to you so I just I didn't want to be obligated in that way
