This is an auto-generated transcript of Never Enough Podcast Episode 3. It 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 AA 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' 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 uh 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 little a little bit more chill although I'm about to get busy we're about to work on uh 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 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 they sleep through so nice
I I get to bed around 10: or so and then I 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 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 I don't really I don't schedule things I don't have a lot of stuff on my calendar um I didn't really use a calendar very much before u 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 buil 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 there 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 for for hay 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 fantastic so maybe I got to make this switch Fantastico is a great product it really is I 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 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 hate calendar has a has a literally a 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 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 golf stream 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 golf stream 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 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 cuz the street streets are 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 it's fine and 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 this 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'm I've always been motivated to just make much
better versions of things and and charge very very fair prices for them like with Bas camp 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' been 99 bucks unlimited user 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 cuz you're a good guy or is that because you and David don't 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 that's not the main reason there's some of the ladder which is we don't want to build an organization that would that would have to service an account that's paying us $65,000 a year and has 6,000 employees
and you know 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 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 software still not software but like 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 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 uh 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 you know 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 stuff it right that I 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 you so much 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 know anyone anything I'm really curious a is that an accurate reflection and B where does that come from for you like what 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 dependent 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' no 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 is uh that valuable to to give up to trade for
3% I mean I appreciate that it's very very generous but I it almost doesn't feel like a fair deal to you uh so I I just I didn't want to be obligated in that way where does this come from I don't I don't know other than I I you could trace it back to a million things and I don't know if any of them are the reasons so I'm not going to go through the long list but I just know that because I'm in this position where I can do what I want and we built a business that allows us to do what we want and
we haven't taken outside money that prevents us from doing anything we want we can stay in business as long as we want we're profitable on purpose with high margins so we can mess around and screw around and get things wrong and it won't matter too much I've just come to the conclusion that like I should take it full advantage of that opportunity that rare opportunity to truly say no to things that would seem to be obvious yeses but that I just feel in my gut I just don't want to deal with and I've
I you could say I've made mistakes around this I remember I I don't think of things as mistakes frankly by the way but I could see other people saying this so for example I was offered the opportunity to invest 100 Grand into Airbnb when Airbnb was running out of their apartment originally I think they had like eight people I don't know what that would be worth today I mean I have no idea but I I didn't do it at the time because like I didn't want to go I want to go through the process of the paperwork
and also like they they you know at the time they weren't profitable and for me it was important to invest in profitable businesses and of course they were tiny and who knew what they were going to be but I mean looking back now you can see but I didn't do that I was just catching up with ow one from intercom there was a moment in in time when they' offered me 1% for advice as well and I'm like I just I didn't do the paperwork you know I didn't so like I mean it's cost me money in a sense but I
but it it doesn't I don't really look at it that way but it's cost you it's it's paid you Insanity I mean I was going to ask you cuz so you externally looking at you and you know I know you as a friend I talk to you a couple times a year externally I always go Jason's got it all figured out he doesn't do anything he doesn't want to do obviously you do what are those areas where you still get frustrated or you still have obligation or you get pulled down rabbit Trails you say yes to things like what
where do you need to where do you have work to do yeah I mean I don't have it all together I'd say with work we have it pretty together but there's things I don't know how to do like we've grown our business to a certain level I don't really know how to grow it beyond that I don't need to grow it beyond that but I really don't know how also and so that can be a little bit frustrating from time to time we've tried a bunch of things that we have never been able to crack the the nut on like marketing
specifically not like the way David and I talk about the product we're and the company we're good at that but to like deliberately set out to say we're going to spend 5 million bucks and make this worth it we just can't figure out how to do that I don't know how to do that we've hired a few people we're exploring things but I just there's some stuff that by the way it doesn't really frustrate me because we don't need to do that but I wish I knew how to do that and I don't so but I I don't look at
that as like self-improvement I need to to worry about it's just like also I'm I've gotten much better at acceptance just like I don't know how to grow a business beyond the business I've grown and if I was a CEO of another business I don't think I'd be very good at it I think that I was uniquely suited to do what I'm doing right now and built something that works for me but I don't think I'd fit in pretty much anywhere else so just accepting the fact that like I'm not some great CEO I'm just the
guy who knows how to run this business like I fit into this suit I don't fit into some other suit I fit into this one really well it's tailored for me and it works I'm okay with that so I don't know I I tend not to worry too much about like what we're supposed to be or how we could be like people will often tell me like you guys have left so much money on the table and you guys could be so much bigger and I'm like yeah probably right I don't really care though uh it'd be interesting to know how
to do that but I don't really care to do that um and maybe that's just because we've gotten very lucky and we don't have to care um and I'm perfectly okay with that outcome too so I don't know but in terms of like life for example you know a parent I'm a father there's things I I need to get better at there especially around acceptance with with kids you know know I often like want my kids to do certain things or be a certain way and they're not that way and that's been something I've really had
to work on so I feel like most of the work I have to do right now is is on the personal side of life and not professional so often yeah I was just an hour and a half late to drop my kid off at school and then I dropped him off and then I got a call five minutes later from the office and they said his entire class is on a field trip and so I spent the entire morning shuttling him off and buying him a bathing suit for this field trip last minute so I feel you on that it's interesting like if you look
at different types of businesses you mentioned craftsmanship you know there's someone like the great sushi chef jro from Jiro Dreams of Sushi where he's got like two locations it's him and his son they're the only trusted people they charge the maximum price and they do the best possible job and then on the flip side there's Chipotle and Steve 's right and you guys are really interesting because you've had incredible financial success UC but you have gone more on the Juro side would you be okay
to just say my business will never do more than this in revenue or expand or how do you guys think about that like at what point would you pass the Reign to a CEO or focus on one area of the company or whatever like is this a relay race or is this a life race or what what is it it's a good question I've been thinking David and I've been thinking more about that we just this is our 25th year in business so it's it's a long time naturally we don't have another 25 years us to do this I don't think
that wouldn't make sense I don't want to be 75 doing this it just doesn't make sense so there's a few things in there let's first start with the the Juro uh or Chipotle comparison we're definitely more on the jro side although we're making more products so we are essentially opening more stores in a way I see each product that we make as a bet on an idea and some hit and some don't we hit huge on base camp we hit pretty big on high-rise we've had some smaller hits and we have some things that have
not been hits and and we have some more bats for sure we have more ideas we want to do and I want to actually be a bit more ambitious over the next few years so we're actually going to be working on multiple products at once which is something we've never done before not once once.com which is a different thing but like simultaneously so we're going to currently we're starting to work on two products which we're going to build simultaneously and hopefully release on the exact same day and this is
a really hard thing to do and we're going to do that so we're interested in that we think both of them are going to be hits and so I don't want to wait to do one and then do the other we're going to do them together so will we grow our business Beyond where it is I'm sure we can and I think we will but it's not like there's a number or a Target it's more like let's just keep doing interesting things and see where the chips fall and see how things go if we grow more if we grow 10% or 20% or 30% great
if we if we stagnate for a few years that's fine too I'm comfortable with that we've actually been fairly flat for a little bit here totally fine with that but so it's not we don't pick on new things to hit numbers we pick on new things because we have ideas and we want to see new things in the world and we also want to use those things so we don't build things for others we build things for ourselves and then other people use them and then of course ultimately we do build them for them
after the first version's out so I I would say that all those things are true I'm comfortable with where we are if we can get big or great but it's not because of some goal or some number I don't believe in goals as far as the handoff idea I don't know frankly I've wondered about this actually was going to catch up with you we can maybe just talk about it now um I know you've hired a bunch of CEOs to run a bunch of businesses I I've not done that I don't know how to do that I am afraid I wouldn't
trust someone enough to do that and I'm afraid that I would get in the way actually so I don't know if I'm capable frankly it's really hard I mean you think about it as your business is like a child and a new CEO is like a foster parent except it's a foster parent that you watch and some foster parents abuse your children some dress them in ways you would not like or take them to you know events you wouldn't want them going to and stuff and some of them are wonderful and it's really hard to predict
what you're going to get when you do it the first time I think what would drive you crazy and what kind of drives me crazy a little bit is so we bought the Aeropress coffee maker company about three or four years ago and I'm a designer like you I love products and I love Aesthetics and you know well-made objects we bought the company and we hired a wonderful CEO and we had some highlevel ideas about product Innovation and all that kind of stuff and now I'm seeing those products so I'm getting you
know in two weeks I'm getting a prototype the second prototype of a new product we're going to release soon I I get it I use it I admire it but it's kind of like I'm a consumer of it I'm not really I didn't have any responsibility for any of the design decisions I could just say like great job guys and so it's it's a little bit like the difference between being the owner of a soccer team or the star player and being the star player is really cool but it's also stressful and hard
on your body and so it's a it's a hard decision and it's kind of it's I bounce between the two and it's I was going to say it's so interesting watching you guys bounce around too because I remember about 10 years ago you guys announced that you were going from multiple products to focusing just on base camp I think there's this natural kind of when you're a creative person you naturally expand and then you contract and it it's exciting to see you in this moment of expansion but tell me you talk
a little bit about that just for a minute we touched on a bunch of different stuff here but when you guys made that decision to just focus on base camp what happened over those 10 years that caused you to start all these new products again so we went all in on base camp and either folded existing products in or or spun them off or just sort of kind of kept them around but didn't sell them anymore and so we were all in on Bas Camp changed the name of the company to base camp built an extraordinarily
good version of Bas Camp Bas Camp 3 and then Base Camp 4 which is the current version which is which is the best version we've ever had I'm really proud of it but I found that working on one product I thought I thought I was going to love that and we made it really really really good and we keep making it better and better and better but every once in a while you have a new itch I think we suppress those itches for a while I found that I just don't want to suppress I I don't feel good when I suppress
so like at our at our core David and I and the rest of the company we make things we're makers we like to make new stuff I don't like to feel suppressed we had these ideas let's do them let's build hey was the next thing we built after that and it was just so much fun to build something new again to bring new ideas to Bear to design in a new way like hey looks very very different than than base camp everything about it different we're able to sort of stretch and flex our muscles again and like make
something from scratch again and that was wonderful even though we make new versions of base camp every handful of years there's there's still this path from the previous version of the new version there's still a commonality even though like it's new it's still the same product in a sense sense hey was brand new um campfire which is the new thing under once or even just the idea of the once once.com pay for software once thing is a new thing and these two new products are going to be new as well
with products we've never done before new categories we've never explored before so I feel like we're just we had to eventually be honest with ourselves again and sometimes what happens is is that you you come up with a a direction or a strategy and you stick to it because you you made the promise to yourself or or to the industry or whatever and 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 and so some
people are afraid then that point to like change their mind because people see that as like some sort of weakness or like you said You' never do this or whatever it's like I don't really care what I said like for a long time we felt this way now we feel this way and we're going to expand into this new feeling so I found that to be not only like exciting but liberating and healthy and the company's in the best place it's ever been in because of that we actually are able to attract really ambitious
people who want to build stuff like we're a place where you build things this year we're going to have four products out four new products out like it's very rare to join a company of our size where anything is released that's significant in a handful of years and so you know by doing this we're going to attract even more and more people who are ambitious and interesting and and up for the challenge and I think that's going to reinvigorate us in a lot of other ways too so I think ultimately
it's a long answer and I kind of said it but like we just had to look ourselves in the mirror and be honest about us and forget about what we thought about us but who are we now and we are a company and a group that wants to make stuff so here we are do you ever find yourself doing that by the way you like you stick to some principle that you put out there in the world and you feel like you must now support that principle till the end of time it's like kind of frustrating totally well I always I
always think about that that Jeff bezos's quote smart people change their minds right right you know we faced this with public market investors oh well you know you said you were going to focus on XYZ 2 years ago and you know well the world changed AI came out there's always shifting things and I think that you have to be able to do that it's been it's been fascinating though because you know so I about 10 years ago I delegated all the operations of all of our businesses to CEOs and I'd find myself
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