FULL INTERVIEW Jason Fried Podcast Interview: Love Your Work w/ David Kadavy

FULL INTERVIEW Jason Fried Podcast Interview: Love Your Work w/ David Kadavy


Hey YouTube Subscribers. It’s been awhile
since we saw each other. I just wanted to tell you about my new podcast, Love Your Work. so in case you don’t keep up with what I do
in other places on the web, I wanted to let you know about a podcast that I started, called
Love Your Work. It’s been going on for a couple of months
now, but it’s done pretty well. It hit the #1 in the New & Noteworthy podcasts in the
business category on iTunes. And I figured there’s probably some of you who are subscribed
here on YouTube and you’re not necessarily following everything that I do everywhere
online so I wanted to make sure that you got a chance to check it out. So the show is basically
I try to interview people who have really carved out success by their own definition.
and I try to dig into how did they get where they are. How did they find their superpowers?
How did they bust through doubts that they had along the way? What are compromises they’ve
had to make? And the first guest that I had was Jason Fried of Basecamp who is I think
the perfect person to talk about building one’s success by their own definition. So
I just want to go ahead and share the interview with Jason here and I don’t plan to share
all of my interviews on YouTube, this is just kind of maybe a one-off thing and so go ahead
and enjoy it on YouTube, I’m going to put some links in the description so that you
can subscribe and make sure that you don’t miss any future episodes. So, enjoy. [music] S1 00:11 This is Love Your Work. On this show
we meet people who have carved out success by their own definition. I’m David Kadavy,
best-selling author and entrepreneur. This is the first episode of the show, so if you’re
not familiar with me, I wrote a book called Design for Hackers, which is a bestseller.
It debuted in the Top 20 on all of Amazon. Before that, I was the lead designer for a
couple of startups in Silicon Valley, and I freelanced as well. I blog at kadavy.net.
That’s K-A-D as in David, A-V as in Victor, Y, and you can tell how many times I’ve repeated
that in my life. You can follow me on Twitter at @kadavy, or you can join 60,000 others
and take my free design course at designforhackers.com. One thing that’s really important to me is
helping people build a business and a lifestyle that suits them. It’s something that I’ve
managed to do, and I want more people to experience it, and that’s kind of the  idea behind
the show. With this show, I want to introduce you to people who have created businesses
and lifestyles that are all their own. They’ve achieved success by their own definition and
built a life according to their own values. They’re not necessarily going to be millionaires,
but they will be happy people. As the name of the show would imply, they love their work,
and also, I love their work. Now, to help us get the show off to a great start, can
I ask you a favor? S1 01:26 In this first few weeks of the show
we have the opportunity to be featured in the iTunes store in their new and noteworthy
section, and this show is a bit of an experiment. I’m launching with a few episodes and I’m
going to see how it goes, but this first few weeks is absolutely critical. This is the
one chance in the lifetime of this show to really bring in more listeners, and more listeners
means I can put more of my energy into bringing you great guests with wisdom to share. But
in order for that to happen we need reviews on iTunes. Lots of them. They also have to
be positive reviews, but that’s, of course, up to you and the actual quality  the show.
So can you please review this show on the iTunes store? If you loved it and want to
hear more, please give it five stars. [music] S1 02:14 I’m very grateful to bring you this
first guest. He is one of my biggest heroes, and he’s the perfect example of someone who
has built a business and a life according to his own values. Jason Fried – yes, the
Jason Fried – hardly needs an introduction. He is the CEO of Basecamp and a New York Times
best selling author. Jason co-founded Basecamp way back in 1999. It was originally a web
design shop, but they built a little project management app called Basecamp, and now that’s
the focus of the company. In the process of building Basecamp the company also created
Ruby on Rails, which is an open-source web framework that powers thousands of sites.
And the thing I admire most about Jason is his contrarion thinking. Whatever the prevailing
wisdom is, Jason seems to speak up and explain why that wisdom is wrong. He intentionally
has setup his company small. His employees can live and work wherever they want, and
they get a three day week during the summer months.
The company is almost totally bootstrap. I say “almost” because they did take a little
bit of investment from the one and only Jeff Bezos of Amazon, primarily just to be able
to give him a call once in a while. S1 03:23 Jason has co-authored three books,
one of which is the New York Times best selling Rework, in which he and his co-founder, David
Heinemeier Hansson, share their rules for running a simple business. This interview
is about one hour long, and there is so much more that I wanted to ask Jason. It could’ve
been several hours easily. We talk about Basecamp in the beginning, which you may already be
intimately familiar with, but stick it out and we soon start digging into the source
of Jason’s famously contrarion thinking. I’m really fascinated by where it comes from,
because I’m someone who tends to be a bit contrarion myself, but  these thoughts, they
usually come after I have this deep internal conflict, and it seems like it just comes
so naturally to Jason. So that’s something that I try to unpack in the interview, and
you’re going to find some good tips for listening to that mischievous voice in your head. If
you aren’t already familiar with Jason, prepare yourself. He really spews brilliance. Everything
that comes out of his mouth could be quoted, or could be a Tweet or could be the subject
of a blog post. He’s really easy to interview, which is great because he’s one of the first
people that I’ve interviewed. So I’m very excited to bring you this interview. Let’s
get started. [music] S1 04:44 Okay. So I’m here with Jason Fried
in the Basecamp offices, and I look around here, and there’s this beautiful wood paneling
and it’s just a quiet office. I can’t help but notice there’s nobody here. S2 04:58 No one’s here. One person’s here,
but  he’s at lunch. S1 05:00 Oh, okay. That person’s at lunch. S2 05:02 That person’s at lunch. S1 05:03 Well, we are talking here on the
day before Thanksgiving, so I wonder if that has something to do with it. S2 05:09 A little bit, but also most of the
people even who work in Chicago work remotely, so we’re a remote company. People across 30
some-odd different cities around the world, and, including the people who are here, we
have 14 people in Chicago. Usually any given day there’s five of them here, and it might
be a different five each day but that’s how we work here. Yeah. S1 05:28 Wow, five people. Okay. And this
is a huge office. S2 05:31 It’s a big office, yeah. So we have
50 people in the company and we all get together twice a year. We have an office that’s built
to handle the whole company, but a very small portion of the company is in the office on
any given day. Half the office, too, is dedicated to public space. We have a theater. We’ve
got a big kitchen area, a reception area. It is still a large office, though. S1 05:54 Yeah. We’re in Chicago so there’s
a little more space available.  So you guys have had this office for how long now? S2 06:04 Since August of 2010. S1 06:07 Okay. It’s quiet, there’s lots of
space, there’s lots of private spaces as well. To what extent do you feel like this office
kind of is an expression of your own personality? S2 06:19 Well, I think it’s an expression
of the company’s personality, which is probably derived at some point from mine since I was
one of the founders. But mostly we’re kind of an introverted group for the most part.
Definitely there’s some extroverted people here though as well, but we try to be respectful
of one another’s space, and privacy and time. So we kind of treat the office like a library,
in that the rules here are kind of like library rules, which is that you walk into a library,
everyone knows how to behave. You’re respectful of one another. You’re quiet. You don’t interrupt
people. People are studying, and thinking and working, and that’s the same way the office
here works. So for the most part, even if it’s full of people, it’s pretty quiet and
pretty hush, and  then people can go into these private rooms like you and I are sitting
in right now and have a full volume conversation without interrupting people on the outside.
Just like a library, they have little side rooms where you can sort of talk loudly and
not interrupt people who are reading outside. S1 07:14 Yeah, that was always something that
bothered me whenever I worked at a company. I might have a bunch of different roles, but
I might be ears deep in some code, and somebody would come up, and tap me on the shoulder,
and interrupt me and just lose all of it. S2 07:28 You lose it all. You lose the focus,
the zone, and so we want to protect that because that’s a really hard thing to get into in
the first place. So if you’re in that, we want to make sure that you stay in that as
long as possible, versus inviting interruptions all day long, which is what a lot of modern
offices are all about these days. S1 07:45 Yeah, I can definitely relate to
that. I’ve noticed that before. So you guys started out as a software sort of consultancy,
right? Or a web design company. S2 07:57 Web design. Yeah, we started as a
web design  company. S1 08:01 And that was called 37signals. S2 08:02 Yeah. In 1999 we launched the company
in August, and we were doing website design for hire, but just redesign work for the most
parts. So we weren’t doing programming. We were just doing visual redesigns. So people
already had the sites and we were like, “We can make that site a little bit better,” and
so they would hire us to do that. S1 08:19 Yeah. And now you are concentrated
entirely pretty much on this one product, Basecamp. S2 08:25 Yeah, Basecamp. And Basecamp 3, the
third version of that, just launched a couple weeks ago. S1 08:30 Oh, cool. S2 08:30 Every four years or so we completely
reinvent the product from the ground up. Not a single line of code, not a single piece
of design is shared. We make it all over again every four years, roughly. So we just did
that for our third major time. Basecamp’s been around for 12 years. It came out in February
2004. So about 12 years total now. So we’re on the third major version. S1 08:50 That’s funny. I guess I hadn’t noticed
that you reinvent the whole product every four years. S2 08:55 There’s similar themes. So it’s a
lot like– think about  cars. We’ll take the Porsche 911. Porsche 911 was released
in 1963. It’s about 52 years old now, but there’s been seven generations of the Porsche
911. So every seven years, roughly, they do a new chassis, they do new engines, they do
new technology around it. But it’s still a Porsche 911. It looks roughly the same. The
engines in the back. The driving dynamics are similar. You can identify a 911 that was
made today and a 911 that was made 50 years ago. You can tell there’s continuity, but
roughly every seven years it’s an entirely new car. And the same thing is true for like
a Honda Accord or a Civic. These lines have been around for decades, but every four, five,
six, seven, eight – in cars it’s more like five to eight years because it’s very expensive
to make a new car – they make a new car. It’s still an Accord, which means it’s a four-door
primarily. They have a coupe version too, but it’s like a family car. And the Civic’s
a little bit smaller. They have these themes and these spirits around the things, but
they’re all new. And so  that’s what we do with Basecamp, is that Basecamp today, in
2015, can trace back to base camp classic, which is the first version of Basecamp in
February 2004. The themes were similar but the product is reconsidered in a big way every
four years, and in between that we just sort of improve the existing version. But then
there’s a point where you can’t pack new ideas onto an old chassis, so we kind of redo the
thing from scratch. S1 10:26 Yeah, that car analogy is interesting.
I’m not totally up on the designs of cars, but I imagine that, say a Honda Accord, there’s
certain values that are portrayed – values about what a car is and what is important
in a car being portrayed in that. And then there’s all this changing technology, and
then there’s certain trends maybe that are influenced by other– S2 10:47 Exactly. S1 10:48 –what the drivers are used to. S2 10:52 Yes. S1 10:53 That those sort of things change,
and so that sort of calls for a total redo. S2 10:59 Totally. And you think about,  like–
I think just cars are really good metaphors for this because you think about the Corvette,
which has been around, I think, since the 50s, and there’s like a spirit to that car.
It’s a two-door sports car, it’s kind of a long-nose. There’s a spirit to it. And even
though they don’t all look the same over the years, there’s a language and an idea behind
the Corvette which stays in the DNA of the car, but the car is redesigned and reengineered
completely from the ground up every seven years or something. That’s just how that industry–
most industries work that same way. S1 11:33 Yeah. I mean, they’re still positioned,
in a way, against other types of cars. The Corvette, it’s a different thing from a Camaro,
right? It’s a different type of person that will drive it and it’s different sort of values
that person has. Right? S2 11:48 Yes. So each car has it’s spirit–
it’s much like– look, you are not the same person – I’m not even talking, like, personality
– you don’t share a single cell in common with yourself from  ten years ago. S1 12:00 Yeah. S2 12:01 So you’re actually– but you’re still
David. You’re still the same guy. You’ve changed. Your tastes have changed and your points of
view have changed, but you’re still you, even though you’ve been completely reengineered
from the ground up in many ways all the time. So there’s iterative tweaks, and then at
a certain point you’re all new. You’re actually all new compared to what you were ten years
ago. S1 12:23 Yeah. So let’s talk about that. S2 12:24 That’s a little bit of a weird analogy,
let’s stick to the car one. But that’s kind of what we’re trying to do here, instead of
the alternative, which is typically how software works, which is that it’s constantly iterated
on. Which is good, but that’s when the code base gets really difficult to work on at a
certain point, because it gets old and the technologies that you build on are kind of
old. It becomes hard to work on, you begin to slow down, and you can’t handle brand new
ideas because you try and fit them into the current patterns and it’s like, “But this
won’t quite fit anymore.” So you kind of shoehorn it in, then you make compromises, and that’s
how things start to get bad over a certain point  of time. S1 13:01 Yeah. So let’s talk about that DNA,
then. Basecamp, for those who aren’t familiar, is a project management web app, basically. S2 13:14 Yes. S1 13:14 I mean, there’s probably– S2 13:16 There’s iOS and android apps, yeah.
All that stuff [inaudible]. S1 13:19 When you started, it’s like your
main competitor was maybe Microsoft Project. S2 13:26 Main competitor has always been the
same: email. S1 13:28 Email, okay. S2 13:28 Email and habits. S1 13:31 But when people would think of project
management, would they think of email back when you guys were first starting? S2 13:39 If you ask people even today what
their primary method of working on projects with people is, it’s still email. So email
is still the biggest. Our industry thinks there’s certain products of the time that
are the big product, but the biggest of them all is email. And that’s not a product, it’s
like a thing. S1 13:58 It’s a protocol. S2 13:58 Yeah, right. But  that is the thing
you’re always battling against, is email, phone, in-person habits. That’s the thing
you’re battling mostly against. The biggest thing that you’re trying to do is sort of–
there’s this idea of non-consumption, which is this concept that there are people out
there who work with others, and they need a better way to do that, but they don’t know
how to do it. They don’t use any products to do it yet. I mean, they use products, but
they use products that are not built for this purpose, but they just use other things. And
they don’t even realize that there’s something out there that would help them. They’re non-consumers.
They want to consume. They want something better, but they don’t even know something
exists. So our industry sometimes thinks that whatever the hot product of the moment is,
that everybody uses that. But actually, all things told, a very small slice of people
use that, and most people don’t use anything. So that’s always the biggest  competition
in our opinion, is the people who don’t use anything. S1 15:03 I feel like there’s a parallel we
draw in there between email and what we were talking about with office interruptions. The
email is this sort of portal where anybody can interrupt you, and you’re providing a
space through which everything is about this project that you’re working on right now – all
the communication that’s happening and all that within Basecamp. What is that DNA of
Basecamp? S2 15:32 Here’s the thing. So the DNA of
Basecamp, there’s a couple things going on here. No matter what it is that you’re working
on, if you have a team there’s a few things you need to do. I don’t care if you are building
a building, or you’re working on a small school project, or you are putting together a publication
or you’re building a website, when you work with people you’ve got people problems. So
you need a way to divvy up and organize the work that needs to get done amongst the group.
 Our take on that is to-dos, but let’s forget our implementation for the moment and just
get back to the fundamentals. So you’ve got a group of people. You want to do some work
together or whatever it is. You’ve got chunks of work, pieces of work that need to be outlined
and divvied up in some way and assigned out. You need a way to hash things out quickly.
So sometimes you just need to hash stuff out and go informally back and forth really
fast. Sometimes you need to slow down and present something, and think about something,
and pitch something, and write a thoughtful post or something and give people a chance
to write back in time. So there’s moments when you need to make announcements, there’s
moments you need to hash stuff out quickly. You need to keep track of when things are
due and what the major milestones are – what’s coming up next, when is thing launching or
when are we doing this thing together? So there’s some dates around it. There’s artifacts.
There’s files, and there’s documents, and there’s sketches, and there’s PDFs and there’s
stuff that– typically you need to keep track of that stuff. S2 17:00 You want to organize that stuff.
You need a place where everyone knows where it is, and where to go to get it and that
sort of thing, right? And then finally, you need a way to check in on people. Like, “How’s
it going?” And, “How are we doing?” And, “Are we doing the right thing?” And, “How do you
feel about how we’re doing it?” And, “Are you stuck on anything?” Those kind of things.
So to me, it doesn’t matter the kind of work. When you work with people, those are things, right? Hashing stuff out, divvying up work, dates,
artifacts, making announcements, being able to get a hold of people when you need to no
matter what their speeds are, that sort of thing, right? So that, to me, is the DNA
of what Basecamp’s about. It’s about understanding how groups actually work together to make
progress on something. There’s difference too, because there’s moments when you’re just
social and you’re just kind of, like, social. You’re not trying to make progress there.
But when you want to make progress on something, Basecamp comes in and helps you make progress
on things with other people. S1 17:51 Yeah, and I like that you’re– S2 17:52 It’s a collection. Let me– it’s
really a collection. That’s the the thing that’s always set Basecamp apart, is that
it’s a collection of unique  tools that work together to help a group make progress on
something together. There’s many ways to approach things. There’s a way to piece together a
bunch of separate tools, and duct tape them together and try to point at each thing, or
there’s a way to buy something that kind of tries to do all those things really well in
a simple way, and that’s kind of our side. We want to give you one thing that you can
use to do all these things together with a group, versus you having to go out and shop
for a bunch of different solutions, and try to tie them all together and get people on
board on five or six different products. S1 18:35 It sounds like you’ve been able to
really think about the abstract needs that are there and separate that experience from
the technology itself. It’s not Ajax, to use a very 2002 term [chuckles]. S2 18:50 Very early, yeah. S1 18:51 It’s not Ajax. It’s not about all
these individual technologies or something. It is managing these sort of abstract things
that are floating in  the ether and making them into something that you can get a handle
on. S2 19:04 And getting your head around it and
getting organized around it is a really important part of working together with people. The
thing is that everyone can have their own individual messes, but if you bring someone
else into your mess they’re going to be like, “Woah, I don’t know where things are.” So
you need to have an organized place, a space, a shared place where you can do this kind
of work. But yeah, it’s not about technologies. It’s not even necessarily about individual
feature sets, because when I say, “Hash things out quickly,” what I actually mean is– in
our implementation is more of like chat. Campfires are now in Basecamp 3. But in five
years chat might not be they way to hash things out quickly. There may be another way to hash
things out quickly. So, it’s not about staying true to a tool set. It’s about staying true
to the problems you’re trying to solve. This is what gives us the opportunity to resolve
those in new ways [crosstalk] Use it to [crosstalk] technology at hand. Exactly. Just like the cars that change over time
with technology. S2 20:00 Totally. Yeah. Bluetooth wasn’t
a thing in cars eight years ago. Now it is. Navigation wasn’t a common thing, and now
it’s in almost every car. So technology moves, ideas move and things you can do change. And
that’s why I think forcing yourself to reinvent yourself and be willing to look at those technologies
and those new options on a regular basis is very viable. S1 20:23 Now, when I think about you reinventing
the product every four years, I can’t help but think about how most people would react
to doing something like that or the idea of doing something like that. They would be so
scared that everybody would be so pissed when you change everything that they’d be afraid
to make a change like that. How do you get over that? S2 20:49 Yeah, it’s a great question, and
the way to get around that is to, again, get back to people. People do not like to be forced
into change.  People don’t mind change. People hate forced change. So we never force anyone
to switch versions of Basecamp. People who’ve been using Base– we have customers who’ve
been using Basecamp for 12 years. Same version. They signed up for Basecamp when it was just
called Basecamp. Now it’s called Basecamp Classic, which is the original version. We’ve
never forced anyone on Basecamp Classic to move to Basecamp Two and no one on Basecamp
Two has to move to Basecamp 3. We’ve made a commitment to our customers to always maintain
every major version of Basecamp forever. So if you’re happy with Classic, our definition
of new may not matter to you. New doesn’t matter to you. Consistency might matter to
you– S2 21:39 But the new customers, it would be
to your detriment to have the original interface with the technology of 2002 or whenever it
was– S1 21:48 2004, yeah exactly. S2 21:49 –2004, and somebody shows up and
that’s what you’ve got, that would be a problem. S1 21:53 Totally. So new customers today
who go to Basecamp.com will be signed up for Basecamp 3. That’s the only thing they can
sign up for. The newest, latest,  greatest version of Basecamp we’ve ever made before. Customers
who’ve been with us from 2004, some of them might still be on Classic if they’ve chosen
to. Some of them might be on Basecamp 2 if they’ve chosen to be. Up to them completely,
entirely. That’s how we solve that problem. We don’t force change on anybody ever. S2 22:17 You don’t run into situations where
that backwards compatibility is just impossible to support? S1 22:21 We don’t support backwards compatibility. S2 22:23 Maybe I’m using the wrong terminology
there, but– S1 22:26 If you start on 3 you can’t move
to Classic, because there’s not a future parity. For example in Basecamp 3, you can assign
– this is a small example – but you can assign to-dos to many people. In Classic you can
only assign to-dos to one person. So if you’re in Basecamp 3 and you assign a to-do to six
people, and you try to go back to Classic somehow, you’d lose data because we wouldn’t
know where to– you can’t move backwards in time. S2 22:50 So you’ve been doing this for a long
time. Basecamp has been around for 12 years in itself. The company has been around– S1 22:57 16 years. S2 22:57 –for 16 years. This  reinventing
every four years, is that something that helps you keep it fresh and keep it being something
that you want to be doing everyday? S1 23:08 Yeah, it’s for everybody. It’s partially
for us. It’s fun to make something new and it’s fun to improve that thing for a while,
but at a certain point you want to make something new again. The way we did it in the past was
we kept making new products. So we made Basecamp, then we made Backpack, then we made Campfire,
then we made Highrise and then we made the job boards. We’ve made a variety of things
over the years. What ends up happening, though, is that making something is actually the easy
part. The hard part is that once it’s out in the wild you’ve got to maintain it. You’ve
got customers using it. They have demands, and you’ve got to provide customer service,
and support and all these things. So we love the act of making new things, but we’ve decided
that we want to focus on making one new thing over and over. That’s how we keep it fresh
for us, also keep it fresh for the market and keep it fresh for customers, but also
not ever  upset existing customers by forcing them on to something new that they’re not
ready for or they don’t want to be in. Something I learned early on – and it’s sort of a ridiculous
revelation because you just expect that you would know this, but it’s one of the things
you just don’t think about. Software companies especially almost never think about this.
People are always in the middle of something, right? S1 24:19 So if I release a brand new version,
and they’re in the middle of a project and they’re trying to work on a client project
with somebody, and we release a new version, we push some them on to the new one, they’re
in the middle of something else. They’re not ready to move to this. They don’t want their
software to change in the middle of their project. So once we realized that, we realized,
like, “Okay, that’s a deep insight and very important. Our product is not their lives.
Their lives is their livelihood. The work that they do for their client is what’s important
to them, and they don’t want their software tool that’s aiding them all of the sudden
changing on them in the middle, because that’s really disruptive and anxiety producing and
stuff.” So that’s why we don’t  force anyone to change. You’ve got to get to those human
insights. The thing I’ve noticed most is that the things that drive people away are fear and
anxiety. It’s not about, “You don’t have this feature. You don’t have that feature.” It’s
the fear and anxiety attached to forcing me to shift, or forcing me to change, or forcing
me to switch or forcing me to do something I’m not ready for – that’s where people really
recoil. S2 25:24 Not having control. S1 25:23 Yeah. People don’t want to be in
a situation where someone’s changing up underneath them that they rely on. That’s a really uncomfortable
feeling. It’s like an earthquake. You live somewhere. You rely on the ground to be solid.
You trust that the ground will be solid. Then one day the ground starts to shake, and that
is terrifying because you can’t go hide from that. S2 25:45 Have you experienced a couple earthquakes
before? S1 25:48 I have, and it’s terrifying. S2 25:48 Yeah, I have too. It’s terrible. S1 25:49 Terrifying. S2 25:50 And they weren’t even big ones. S1 25:52 No. Right. S2 25:52 It’s the worst. S1 25:53 I’m a Midwesterner, so a small one
is a big one for me. But the thing is, if it’s really crappy weather-wise outside you
can kind of go inside and hide,  but you cannot hide when the earth beneath you moves,
and that’s a terrible feeling, and that’s what software’s like to people. When there’s
this thing they’ve been relying on that’s been consistently working a certain way and
all of a sudden it changes on them, that’s an earthquake. We don’t want to create earthquakes
for customers. S1 26:14 Yeah, especially this things that
they’re relying upon to help them– S2 26:19 Do their job. S1 26:20 Do their job, do their work, to manage
their projects. If I’m using a bad word there, I don’t know. S2 26:25 Totally fine. Actually, what’s interesting
is we’ve gone away from the word “project,” which maybe we can talk about in a little
bit. But yeah, fundamentally, absolutely. People use Basecamp to run projects, and they
use it for other things too. Imagine if you’re doing work for a client. You’re a designer.
You do work for a client. You’ve trained the client on this thing. You’ve told them this is how
it’s going to work. This is a client relationship, which is often delicate. They’re paying you
a lot of money. You might be friends with them, but it’s still a delicate relationship
at some level. And all of a sudden, this thing you told them was going to work one way, all
of a sudden works a different way on Tuesday then it did on Monday. That is a  bad situations,
so we don’t ever want to put our customers in those situations. S1 27:04 Right. You’ve definitely gotten really
comfortable over all these years with your particular way of doing things, but I want
to step back a little bit further and get an idea of where it all comes from. I’d say
that you’re probably known for being a contrarian thinker. Would you agree with that? S2 27:26 Yeah, probably. It’s funny because
I don’t think my ideas are contrarian at all, of course, but against our– let’s call it
against our industry, yes. S1 27:35 Yeah. I think that a lot of people
have thoughts from time to time where there’s a prevailing wisdom and they think, “Well,
that doesn’t seem right.” But then they think a lot of people– they bottle it up inside
or they don’t act upon it. They don’t give themselves the permission and the confidence
to go ahead and say, “I don’t think it should be that way. It should be this other way,”
and to go ahead with it. I think that that’s somethin,  even if you go back and look at
the 37signals – which is the former name of the company – 37signals.com/manifesto, there’s
all these things about, “We’re small on purpose,” and all these things that are against the
prevailing wisdom. “We purposely are not full service,” things like that. S2 28:23 By the way, even that site itself–
actually, that site is the most contrarian thing we’ve ever done. We’re a web design
company. There wasn’t a piece of work on that site. It was black and white. It was all text.
37 ideas is what that was. If you think about back then – that was in ’99 – web design firms,
even today– S1 28:45 1999 for those who can’t remember– S2 28:47 Right, 1999, the previous century. S1 28:50 It was a different century [chuckles]. S2 28:53 But even today, it’s all the same.
Basically, agency sites are portfolio sites for the most part, which is like, “Here’s
our  shining work and here’s the work we’ve been doing. Here’s pictures of it,” and I
get that. We didn’t have a single picture of any work that we’d done on that site, and
the whole idea was that everyone’s work pretty much looks the same. If it’s good, it’s roughly
the same, right? But what sets companies apart and people apart, I think, are the ideas that
they have, and most companies don’t think they way we thought we thought. And so we
want to put our ideas out there to make us appear different and to attract the kind of
customers that we want to work with, who were people who’d appreciate this kind of thinking,
versus just someone who’d appreciate a pretty picture of a website that we made. That doesn’t
help us self-select our clients. So that was the idea behind that. S1 29:38 I think this is something that’s
so important for people to master, to be able to have a thought that’s different from the
prevailing wisdom and to give themselves permission to go forth with it. Take us back to 1999
when you decided to make this all text. Was that something– did you know that it was
something different from the prevailing way to do it?  How did you arrive at that and
give yourself permission to do that? S2 30:04 Great question. We knew it was different.
We knew no one had never done anything like that before. It’s funny, they were almost
like tweets or short blog posts. They were just these really short thoughts. We weren’t
trying to be different. We just realized that we were, and then we’re like– Originally,
one of my partners in the business was a guy named Carlos Segura, who’s a graphic designer
in Chicago. He has a line that says, “Communication that doesn’t take a chance doesn’t stand a
chance.” That’s his motto, and that drove us early on, which is like, “Let’s take a
shot. What do we have to lose here? What we actually had to lose is not being ourselves,
and that is a bigger loss than being yourself and not getting traction.” If we were trying
to act like everyone else  then we weren’t really being ourselves, and that’s the loss.
“So let’s take a shoot at putting ourselves out there, doing this differently, and let’s
see who we attract this way. Everyone’s fishing with this lure. Let’s put a different lure
out and see what we attract, and maybe we attract some big fish that no one else knows
how to attract, because everyone things the only way to attract this kind of fish is this
way.” S2 31:20 And it turned out that we landed
a couple big projects, and we’ve been profitable as a company ever since then because of that.
I mean, looking back, it’s a bold move, but at the time we just didn’t think it was bold. We’re
like, “We have nothing. We have nothing yet. We have no company yet, so we have nothing
to lose. So let’s take a shot.” It’s a lot easier now, in my opinion, to be hesitant
and being afraid to take a risk when you have something to lose. Like, “We have something
to lose. We’ve got a great business. We’ve got a lot of customers. We’ve got a reputation.
We could lose that now,” and then you get a little bit tight.  So we’ve tightened
up as a company over the years. I think most companies do. But when you’re fresh and brand
new, that’s the time to take a real shot. Why not, you know? S1 32:10 It’s funny to think about that thought
process that you had, because I think– how old were you then? S2 32:17 25. S1 32:19 Maybe around 25 was when I started
to wise up to, “Okay, these thoughts that I have in my head that are different from
the way other people are doing things, I should do something to pursue those,” but I think
before that I allowed other people’s ideas of what success was, or what it meant to what
I should be doing, I think I allowed those ideas to– I know I did. I know I allowed
those ideas to dictate my own actions and put me in situations that didn’t make me happy.
So did you ever experience that sort of thing where you were maybe making decisions based
 what somebody else had decided? S2 33:02 Oh, absolutely. Yeah. Before 37signals,
I was just a freelancer doing website design on my own, and I always referred to “me” as
“we.” When I was doing proposals I’m like, “We will provide a–” because I always felt
like I had to act bigger. I had to act like I was a company. I wasn’t a company. I was
me. I was just me, and I just thought I had to be something else. I remember at the time–
you’ve been around for a while, too. You might remember there was something called USWeb,
which was like wrapping up all these small web design firms trying to make this big web
agency made of– I don’t know if you maybe remember this. I barely remember it. S1 33:46 I don’t remember that. What year
would that have been? S2 33:48 That was like mid-90s, late 90s sort
of thing. It was like– S1 33:54 Mid-90s I was making web pages on
my AOL space and not really– S2 33:58 Yeah, but so was I. Anyway,  it’s
just a thing that didn’t go anywhere, but I’m like, “Man, my firm might be acquired
by a conglomerate.” Like, this weird, stupid shit I was thinking about at the time. S1 34:14 I remember wanting to work for Razorfish
and seeing, “Oh, wow. MTV is a client, and they’re doing all these good things.” Actually,
my thing was Communication Arts magazine. S2 34:25 Sure, CA. Absolutely. S1 34:25 As a designer, I would pour through
the pages, and I’d write down every firm that was there, and I would go to the city and
I would call and try to get an interview. S2 34:34 I’d do the same thing. Same thing. S1 34:37 Really? That’s interesting. S2 34:37 Yeah. I’d go through these designing
[annuals?] and go, “Man, I wish I could do that kind of work.” That’s actually how I
met Carlos for the first time. S1 34:41 That’s exactly the way I was. S2 34:44 Yeah. I think most people are that
way. I think it’s good. I think it’s a good start, and then you come into your own at
a certain point. I think your mid-20s are actually a really healthy moment for that. Before
that I was wide-eyed, and excited, and wanted to act bigger than I was and wanted  to be
more professional. This is the thing. I want to be more professional. That’s the thing
you have when you’re fresh out of school – you want to be a professional. “I need to write
really long proposals and I need to talk in a certain way. I need to act a certain way.
I need to appear bigger.” And that’s just insecurity, and it’s natural. Like, you don’t
know. What do you know? You’re 21, you’re 20. You don’t know anything yet, right? So
you’re trying to act. You’re an actor, and at a certain point you become yourself. And
I think that’s when it’s formative, is when you begin to realize– and I realized this
at some point. I realized it by accident. I was doing these long proposals because
I thought that’s what you had to do. Like, 20-page proposals. I remember writing 20-page
proposals about– S1 35:47 Oh, yeah. I’ve done a couple of
those. S2 35:47 Right? S1 35:48 Yeah. S2 35:49 And you spend– I don’t know. Weeks
and all-nighters, and you write these proposals– S1 35:53 You don’t get the job. S2 35:53 You don’t get the job, right? And
then I realized– first of all, I hate writing 20-page proposals. I think they’re a waste
of time. Because here’s what  happened to me. My parents were doing a kitchen renovation
at home, and they were getting these proposals from contractors. I saw them look at them,
and all they did was they turned to the last page. Like, “How much is it going to cost
and how long is it going to take?” That’s all you care about when you get a proposal,
because to get a proposal from somebody, you’ve already vetted them at a certain level. Like,
“I’m curious about what they would do for me. I know who they are, so what would they
do?” You just want to know, how much is it going to cost and how long is it going to
take? So I realized this. I’m like, “I’m doing these 20-page proposals. I’m busting my ass
on them. I don’t like doing them. It’s what you’re supposed to do, right? Or is it?” So
I started doing shorter, and shorter and short proposals and started winning jobs. At the
end of my freelance career I was doing single-page proposals, and I wasn’t losing any business
over them. I realized, “Holy shit, I don’t need to do what everyone else is doing. I
thought this is how you had to do it, but you don’t have to do it that way.” That’s
where I gave myself permission to go, “Well, what else don’t I have to do that everybody
else is doing?” S1 37:01 Okay. This is exactly what I’m looking
for. This is the time when you slowly started making the proposals shorter and shorter,
and you realized that this thing that other people had told you was so, or somehow you
had come to the conclusion was true, was in fact not true. S2 37:18 It was in fact not true. I don’t
even know if people told me, or I just thought you– I don’t even know. S1 37:23 It was more than not true. It was
false. S2 37:24 It was false at a variety of levels.
It was false that I had to do that to get jobs. It was false that I had to stay up late
and  bust my ass to get work. It was also false that it would make me happy. I was miserable
making these long proposals, so I realized if I can eliminate the misery, and I don’t
have to stay up late, and I can be concise, and get to the point and present my work clearly
in a page or two, man, that’s a bunch of wins, plus it’s a win for the customer on the other
side. And I told them that. I’m like, “Look, I know how proposals are. You’re just going
to look at the–” I said this in my proposal. I’m like, “I know how proposals are. You thumb
through a bunch of stuff, and at the end of the day you just look at the price and how
long it’s going to take, because you’ve already seen my work because that why you’ve asked
me to submit a proposal. So I don’t need to go through all my work again. Here’s how much
it’s going to cost. Here’s how long it’s going to take.” That was my pitch, basically. Like,
“Look, let’s cut through the bullshit, because that’s going to represent how I’m going to
work with you. I’m not going to bullshit you. I’m going to be direct and clear, and we’re
going to work concisely together.” It was like an embodiment of  how we’re going to
work also. That resonated with people. Then I started to realize, “Man, I don’t have to
be like everybody else. This opens up opportunities.” Now, I didn’t see all the other opportunities.
It was just like a moment where I could poke the way you’re supposed to do it and get away
with it, and then like, “Oh, maybe I can do this more.” So I started doing more things
like that. S1 38:57 There’s sort of a sense of mischief
to it. It kind of makes things more fun that way. S2 38:59 Absolutely. S1 39:00 I know I’m that way where if I get
stuck in a rut, I just kind of say, “I’m going to just write this silly, mischievous blog
post or email,” and suddenly it feels fresh and people respond more. S2 39:12 Absolutely. This is something I’m
actually thinking about here right now. Next year there’s some stuff I want to do that
doesn’t seem like it would be a reasonable thing to do. Like, it would be difficult to
justify in the same way  that I think a single page proposal would be difficult to justify
until you realize it works, and then you don’t have to justify anymore because it becomes
true. And so there’s a couple things – I’m being very vague here because I don’t want
to talk about it quite yet because I haven’t formed any ideas thoroughly – but there’s
a couple things I want to do that seem counterintuitive to our own company or our own way of working
that I want to ruffle a bit. S1 39:58 Yeah. So it sounds like you’re trying
to shake things up a little bit in the office. You don’t want to get too complacent in doing
things a certain way. Is that going to bring some freshness, or what’s driving that? S2 40:10 Yeah. Well, that’s part of the whole–
reinventing Basecamp is part of that. Like, being on this schedule where we have to reinvent
Basecamp on a frequent basis. It’s not that frequent, but like four years. S1 40:19 Four years is [inaudible]. S2 40:20 But yeah, in this industry– actually,
it seems like a long time in some ways, but– S1 40:25 Yeah. S2 40:26 My opinions change over the years,
and I have new ideas, and a thought comes to mind, and I’ve been doing some–  one
of the things that’s been interesting is I’ve been doing a lot of in-person demos of Basecamp
3. I’ve never really done a lot of in-person demos of Basecamp before, and it’s been really
interesting because I’m seeing some really cool insights that come from followup questions.
We’ve always thought about demoing Basecamp with videos, or tutorials or whatever, right?
But what I’ve realized is that that kind of demo doesn’t lead to followup questions, and
followup questions are really valuable, because that is where someone requests or looks for
clarity. Like, “Wait. What do you mean by that?” Or like, “Wait, how do you do that?”
Or, “Wait, how do you think about that?” S1 41:21 It’s kind of like where they ask
the question that they were initially too afraid to ask or something like– S2 41:26 That’s a good way to put it. S1 41:27 –but they thought was a dumb question
before, but somehow– S2 41:30 Totally. [crosstalk] That’s a great
way of putting it.  Yeah, a great way of putting it. Those moments, I’m realizing,
are extremely valuable, very valuable. In fact, it’s almost all the value. Yet, when
you do a lot of self-service stuff you don’t get to that value because you don’t talk to
the person, right? S1 41:49 See their facial expressions or– S2 41:51 Yeah, or just the things that– it’s
like a comedian. A comedian writes material, and if they want to do a one-hour show on
HBO, they spend a year in the clubs perfecting that material They don’t know how audience
are– they think all the stuff they’re writing down is funny, but they’ve got to try that
stuff out. You’ve got to try it out in front of an audience and see what reactions– and
sometimes the audience give a reaction on something that you didn’t think was going
to be that funny, or they react to the timing or something. You’ve got to try that stuff
out. So what’s been interesting is I gave a couple of demos of Basecamp 3. One of the
interesting features of Basecamp 3 is– it’s such a basic thing. You can create folders,
and you drag things into folders to  organize them your own way, and I got a standing ovation
from this one group [chuckles]. I was really surprised by that. It was not something that
I thought was going to be like this eureka moment for people, right? But I had to be
there to see that, to feel it, to know that there’s something there now. Then I can follow
up on that and get– wow. I’m like, “Whoa. Why was that such a big deal for you.” “Oh, because–”
and then you get the because. S2 43:06 Every word after because is gold,
you know? You don’t get that when you just kind of like put material out there that people
can do on their own. So I want to do a lot more in-person stuff next year. This is stuff
that does not scale. We have well over 100,000 paying customers. We have a very big business.
Tons and tons of customers, millions of people use Basecamp. I can’t possibly demo it for
all of them, right? But  I don’t have to. What if I can demo Basecamp to 200 companies
a year? What if I could do that? How much better would the product be? How much better
off would they be and how much better off would we be? I think it’s undeniable that
there’d be a deep value there, and I want to think about doing that kind of stuff. Anyway,
that’s very different from how we’ve ever done things before. So that’s just one of
the things I’m thinking about, but I just feel it’s really important to shake up your
own thoughts from time to time. S1 44:02 Yeah, and I love this idea of these
insights of these things that you are taking for granted in a way for whatever reason – maybe
it was an obvious solution to make the folders draggable like that – and then it just blows
away these other people. I think that that’s something that– I find that myself just in
trying, or I have found that in trying to find my own entrepreneurial voice or deciding
what to do in my own career, is that every once in a while somebody  will make an observation.
They say, “Oh, you’re really good at explaining things,” or something like that. And you’re
like, “Well, wait. I didn’t know that.” Was there anything like that for you personally
that helped you find your own path in the early days of 37signals or something? Things
that you didn’t necessarily know that you were good at but you later discovered through
observations like that. S2 44:58 Yeah. I’m not sure if it’s a specific
thing other than like a way of looking at things. So we would do work for clients all
the time, oftentimes bigger clients. Like, back in the early days we’d do work for Hewlett-Packard
or something. We did a website for them. And I’d be sitting in a meeting with them, and
there’d be a lot of people on the table, and they’d be talking stuff through, and they’d
be like– they’d be talking stuff through, putting the ideas through their own process,
which often involved a lot of people, followup meetings and a whole timetable to get something 
to try something. I’d be like, “Why don’t we just try it right now? Why don’t we just
make the change right now and just look at it together?” That, to me, was like, “Of course.
If we want to see how it looks, let’s just do it, and then let’s look at it.” For them,
that was just like a revelation. Like, “What? But doesn’t it have to be this, and that and
approved?” I’m like, “It could be, but it doesn’t have to be. Right now, let me pull
out my laptop, and I’ll make the change, and I’ll hit reload and let’s look at the page.”
That came from me being a freelancer. I was working on my own. I had no one else to talk
to. No one else to rely on. I had to do it all myself. I did all the HTML and design.
There was no process. S2 46:18 So for me, just growing up that way
in the industry, helped me realize that you don’t need a lot people to get things done.
You don’t need a lot of process to try stuff. But a lot of the clients I worked with early
on, they couldn’t believe– they’re like, “You’re a genius.” I’m like,  “I’m not a
genius at all. That is like the worst label to give me. I’m actually being a simpleton.”
I’m just being like, “Let’s just change it and hit reload.” So it wasn’t like a thing.
It was just a way of cutting through. So what I saw there was that process creates layers,
and layers and layers, upon which you then begin to rely. And you don’t realize that
there was a time, when you didn’t have to have all those layers, but you’ve become used
to them and you think then that’s the only way. So I think what I was good at early on
was coming in and cutting through that stuff, and being like, “We don’t need to do all that.
Let’s just do it this way.” And they’d be like, “What? What? You’re not allowed to do
it that way.” S1 47:15 Again, it goes to this contrarian
thinking thing. I’m trying to figure out like how much of it is your DNA and then how much
of it was– was there ever a time–? Huh. I guess what I’m trying to figure out is–
I think that, yeah, I can show a lot of  people, “Here we’re talking with Jason Fried.
He sees things differently from the way other people do,” but somebody can’t just flip a
switch and start thinking in their own way or gain that confidence. Was there ever a
time when you didn’t have the confidence to do that, and how’d that happen? S2 47:53 Oh yeah. I mean, I’ve always had
a world view, I think, which is things are simpler than they appear actually. Which is
funny, because they’re also way more complicated than they appear. What I mean by that is that
things can be simpler. Like, whatever the thing you’re trying to solve, there’s a simpler
version of that. I’ve just always had that in me, that I’m like, “There’s no way this
is the only way we can do this. We can do this simpler. We can be clearer about this–” S1 48:18 What do you think was the earliest
example you can think of– S2 48:22 Of that? S1 48:22 –where you did that? S2 48:29 I remember back before  the web
was around– the way I got started in any of this stuff was I made this program called
AudioFile, which was a music organizing tool. It was like iTunes kind of way, way back,
but there was no digital music. So it was just like a way to organize your CDs and your
tapes. Because I had bunch, and I was loaning them out to friends and never getting them
back. S1 48:51 Tapes, for people who don’t know,
was this thing that had two reels on it and there was this tape-like thing that had music
on it. S2 48:57 It was actually tape. It was tape
that moved [chuckles]. S1 49:00 It wasn’t sticky. S2 49:01 Right. It was magnetic and weird.
Anyway, so I would loan stuff out to friends and never get it back. I didn’t know who
borrowed it and I didn’t know– so I’m like, “I need to organize this stuff. I need to
get my stuff together.” So I started looking on AOL, actually, because the internet wasn’t
around. This was like the early 90s. But AOL was around. There was software boards and
stuff where you could download shareware and stuff. I downloaded a bunch of these music
apps, because there was lot of other people who had this problem, and I just found them
incredibly complicated, and just really  weird, and strange, and ugly and all the things that–
it’s still subjective, but my aesthetic was not being satisfied by their aesthetic. I’m
like, “I don’t know how to do this, but I need something, and I’m going to make one
myself.” So I just got FileMaker and learned how to do it, and made a much, much, much,
much simpler version, because I just made something that I knew I needed. And it wasn’t
about imagining what everyone else needed, it was just like, “What do I need?” And I
was able to cut right to that, and it became very successful product. I made $20,000 off
this little shareware thing. S1 50:08 Just getting checks in the mail and–? S2 50:10 Yeah, and this was the revelation
that I could do this for a living. So I put in the [product?]– just like it was shareware,
which is like, “You could use it for free, but if you like it, send me 20 bucks, and
here’s my home address.” So people started sending me $20 bills, and I’m like, “Holy
shit, I can do this.” S1 50:29 Were there moments of doubt along
the way? S2 50:31 Never, because I  didn’t care. S1 50:33 You didn’t care. It just happened. S2 50:33 It was for me. The product was for
me. If no one used it, didn’t care. And that’s how I’ve always tried to make it, which is
like– we still make Basecamp for ourselves. We need Basecamps to run our own business.
I care a lot more now because we have tons of customers and we’ve got a payroll – 50
people – and the whole thing. But fundamentally it’s still we want to make something for ourselves,
because we know there’s a lot of people out there just like us who need what we need.
That’s how we look at it. But with AudioFile, the first thing ever, I was in high school
or whenever it was, and there was never a moment of doubt because it didn’t matter if
anyone used it. It was a miracle that anyone did. But I needed it for my own thing, and
so it wasn’t even about confidence. It was like, “I need it anyway.” That’s how I kind
of learned graphic design, and learned a little bit of software development, and learned usability,
and learned about customer feedback and all that stuff I learned through those channels
because I’d made my own little software thing. S1 51:32 So there are no existential crises
over like, “Should I do this or that?” S2 51:40 I think the biggest one we had recently
in the company was deciding to go all in on Basecamp, and then what to do with the other
products and stuff. That was like an existential thing, but it was like a moment, and there
was risk involved and all that stuff. Those moments still come up. I mean, deciding what
to do with a product. Do we release it this way or release it that way, and how do we
price it? We have those discussions and decisions all the time, but I try not to worry about
it too much. I worry about it probably more than I should still, but it’s like, “Let’s
make a call, and move forward and see how it does.” S1 52:17 All right. I’ve got a few questions
that are a little more canned questions as we wrap up. What’s the biggest compromise
that you’ve had to make in your career to have the success that you have? S2 52:30 Well,  the biggest compromise. That’s
a really great question. I’ve never been asked that question. I love when I’ve never been
asked a question before. Those are great questions. So I made a compromise– I’ll talk about inside
the business, and this is interesting because it turned out to be a great thing. So David,
who’s my business partner– I’d had two partners originally in 37signals and then they both
left, and so it was just me. And taking on another partner was a compromise in some ways,
because it’s, to me, like, “I’m running the show now, and now I’m going to bring someone
else in and someone else’s opinions are going to matter at that level.” So it was like– S1 53:19 And David, by the way, could be called
a contrarian thinker as well, right? S2 53:24 Absolutely. S1 53:25 So lots of opportunities for you
to disagree. S2 53:27 Yeah, and we do disagree. We still
disagree deeply on certain things. We agree on
most things, and then there are some things that are on the edges that we disagree on
deeply, which is really healthy, and that’s my point. Sometimes it feels like I have to
give– it would be easier if I could just do whatever I wanted, right? But the company
wouldn’t be better, and that’s what I’ve come to realize, and I realized it pretty early.
I’m just talking about the moment of thinking on taking on another partner, again, was this
moment where I have to make compromises, and it turns out that compromises are actually
really damn good things to make sometimes. But at the time I just remember thinking,
“I’ve got it all now.” And this actually includes ownership in the company. I owned a 100% of
the company, and David came on as a partner and now he owns a piece. He owned more and
more over time. Looking back on it, it’s one of the best decisions I’ve ever made, but
I just remember, going back, thinking about– S1 54:28 It was a point of tension, right? S2 54:29 Yeah, absolutely. Internally. S1 54:30 It could have gone either  way. S2 54:32 It could have gone either way. Also,
I talked to my dad about it, and my dad’s always been someone who’s like, “Never have
a partner in business. Never take on a partner because a lot of them dissolve and it gets
really messy and horrible,” and I’ve been really fortunate to always be able to work
with great people. But this is not a compromise I’ve considered recently. I’m thrilled with
how things have turned out. But I just remember at the moment really feeling like I’m taking– S1 54:57 And the two of you had worked together
before that point. It wasn’t just blindly going into this partnership. S2 55:02 No. Yeah, we’d worked together, and
I actually encourage people to do that. I hired David– S1 55:06 Like dating before getting married. S2 55:07 Yeah, absolutely. And I hired David
as a– David was still in school when I first met him, and I hired him. He only had ten
hours a week to give me as on a contract basis to build Basecamp. Actually, before that we
were working on some client work together as a contractor, because we didn’t have any
programmers on staff and he was the first programmer I had ever worked with. This client
hired us to build an intranet for them and we’re like, “We can do the design,”  and
they’re like, “Well, we want you to do the back end too,” and I didn’t know how to do
that. I found David, and he did it with us. Anyway, we had experience working together
on multiple levels, but it’s still– like, the moment you decide to bring someone into
your business, as the remaining founder, it’s a difficult moment. Even though [crosstalk]. S1 55:58 I [?] it myself. I own 100% of my
business, and it would be kind of agony to make a decision like that. S2 56:07 Totally. And I think there’s still
times– I’ll speak for David. I’m guessing David feels the same way, that there’s times
David would just like to do things his own way and there’s times I’d like to do things
my own way. But the fact that we can’t do that and we discuss these things with each
other, we end up with something better. But there’s also, of course, frustrating moments
for everybody in every relationship. I mean, it’s a relationship, right? And that’s cool,
but it is important, I think, when you–  I think a lot of entrepreneurs these days
look for founders. They’re like, “I need a co-founder. I need a co-founder. I need a
co-founder.” So they just go out and try and find one. You’ve got to date someone first,
basically, for a while. I really think that’s important. Because people are complicated,
money is complicated, and people and money together is extremely complicated. There are
few things in the world that are more complicated than that, and that’s the kind of complication
you’re getting yourself into when you take on a partner in a business. S1 56:59 Yeah, it’s almost like this commodity
approach to something that’s so personal, or a person. Co-founders. Like, “Oh, I’m just
going to grab some milk at the store.” S2 57:11 Yeah, it’s not that way. S1 57:13 “I’m going to go grab a co-founder.” S2 57:14 It’s not that way. Especially if
you’re in a business 50/50 or something, like a lot of people do. They start out co-founder
for 50/50. Actually, 50/50 is the worst number in business. There needs to be tiebreakers.
But anyway, that’s another topic. But anyway,  as far as compromises – to get back to that
– I think at the moment it was a major compromise that I had to get over, but I’m so glad that
I did. But it was a big moment. S1 57:41 Yeah. Well, that’s a great one.
I’m so flattered to have asked you a question that you hadn’t been asked before [chuckles]. S2 57:45 I love that. S1 57:47 I’m sure you’ve been asked a lot
of questions. What was the last book that you read that changed the way that you saw
 something? S2 57:52 A great questions too. I typically
do not like business books. I find them boring and too long, but I read something recently
which I don’t even consider to be a business book. A book called– S1 58:03 It doesn’t have to be a business
book, by the way. It could be about– Adrian, who I talked to, said he read a book about
ants. S2 58:11 Totally. And I know that book, and
he told me about it and it’s on my list. But just being honest about it, the last thing
I read that really changed my mind on something happened to be a business book. S1 58:23 Got you. S2 58:23 Although, actually there’s– can
I give you two answers? S1 58:26 Yeah, absolutely. S2 58:27 Okay. So one of them was a business
book called Turn the Ship Around, which is a wonderful book by this guy named David Marquet,
who  was a captain on a nuclear sub, and he was brought in to turn the worst sub in
the Navy around. Like, turn it from the worst sub in the Navy to the best, and the way they
measured this was sailor satisfaction, people who wanted to sail on that ship again. There’s
a variety of things. I don’t remember all of the details, but it was like– let’s say
there was 100 of them. It was number 100. The worst. S1 58:56 Yeah, wow. S2 58:57 And they brought him in to make it
great, and he did it by doing something extremely contrarian. In the military it’s all about
orders. You give orders. Business is often structured a lot like military.
The orders come from the CEO and we all follow the orders, right? And he realized, “Look,
there’s 800 people on this ship. I’m one of those 800. If I’m the one getting orders,
then there’s only one brain on the ship. It’s mine. What a terrible waste to have 800 brains 
but only one of them has to work, and everyone else just does what I say. That is a waste.”
So he decided not to give any orders, which is something the military– you don’t do.
It’s the opposite of what you do. The only order– S1 59:47 This sounds like a great book. S2 59:47 It’s a wonderful book and it’s a
great story, and he tells it. It’s not a business book at all, by the way. It’s not at all.
But it’s sort of like– S1 59:54 Lots of parallels. S2 59:54 Tons of parallels. But it’s not a
business book. He talks about how the only order he reserved for himself was the order
to fire a weapon that could kill somebody. So if they had to fire a torpedo, that was
still on him. Everything else– what he did was, he said– and it took him a while to
make this work, which is what’s really cool about the book is he is very honest about
the failings of it initially. After he enacted the system, everything in his bones told him
to step in and fix these problems, but he’s like, “No, I got to let this settle out the
way I want it to.” Anyway, was that people were not– so the way that it typically worked 
is people would come to him, and they’d say, “Captain, what should I do?” Or whatever it
is, and he’d be like, “Turn this ship 30 degrees starboard,” or whatever. I don’t know. They’d
be like, “Aye, aye captain,” and they’d go do it. He’d give the order. But what he wanted
people to do instead was to come to him and say, “I intended to turn the ship 30 degrees,”
and then he could okay that. But the point is that his okay would just– they’re already
saying what they’re going to do. They have to, in their mind, already know what they’re
going to do. They can’t come to him to ask him what to do. They have to come to him and
tell him what they intend to do. S1 61:12 They have to go through that whole
mental process of taking it through which is– S2 61:15 “Because if he says yes, I’ve got
to do this now.” S1 61:17 Yeah. S2 61:16 “And I came to him with the idea.”
So he got people to come with intent– S1 61:20 Accountability there. S2 61:21 Totally, and think it through and
come with intent. S1 61:25 And ownership [crosstalk]– S2 61:25 And that changed everything. Totally.
And they started thinking. It took a while because it was weird at first, and this is
part of  the thing, is whenever you enact something new at a company, it’s very easy
to fall back on, “This isn’t going to work. This is too weird.” But he talked about the
process of getting over that and giving it space and distance to see if it would work,
and it turned out that it worked and became the best ship in the navy. S1 61:47 That’s a great recommendation. S2 61:49 It’s a wonderful book. S1 61:50 I will read that book. S2 61:50 He’s a wonderful writer and a very
honest storyteller. So there’s that book, and the other book is a book which has the
cheesiest cover ever and also a very cheesy title. It’s called the Mayo Clinic Guide to
Stress-Free Living, and it’s like the cheesiest– the book cover is someone doing a cartwheel
in a field. S1 62:09 Stress-Free Living. S2 62:11 It’s horrible. But it’s this guy– S1 62:13 Made by the Church of Scientology? S2 62:14 It looks like it would be, but it’s
actually the Mayo Clinic, which is like the world’s best hospital. This guy who wrote
it is a doctor there who sort of unlocked a couple of really interesting truths about
the brain and how to reduce stress in your life,  and it’s fascinating. It changed my
life in terms of– I haven’t mastered the techniques, but they’ve influenced me greatly.
The number one thing I’ll tell you about it is that basically there’s a sense– what he’s
realized – and different religions and theologies have come to similar conclusions, but he’s
trying to make this very practical – is that there’s two modes of the mind. There’s the
default mode and the focused mode. The focused mode is when you’re working. He talks about
when you’re really into something, it’s all you’re thinking about, and you’re cruising
and you’re nailing it, right? But when you’re not focused and you’re wandering, your mind
tends to wander towards worry. It tends to wander towards– you start having these thoughts
in your head about the things you should be doing, the things you’re not doing, and, “What’s
going to happen if I do this?” And, “Oh my God, global warming. We’re all going to die.”
You just start– because evolutionarily, you’re programmed to do that, because if you just– S1 63:31 It’s amygdala taking over. S2 63:32 Yeah. It’s like, “There’s a tiger
who’s going to kill me, and I’ve got to be wary.” But he’s like, “In the modern world,
most people don’t have those things anymore.” We’re pretty safe. Not everywhere, but most
places. So you’ve got to get your mind off the default mode, which is the wandering mode,
and back into focus. So he helps you figure out ways. Some people do meditation. He’s
like, “Meditation’s a wonderful thing if you have all this time to commit to it, and
learn and really master it–” S1 63:59 Is that something you’ve tried? S2 64:00 I have, and I’ve never been able
to do it very well. So this really spoke to me, because he’s like, “I think meditation
is a wonderful technique, but it’s not a practical technique for most people.” In fact, a lot
of meditation’s about just letting your thoughts come and go, and that’s when you have a lot
of the bad thoughts. It’s very hard to really, really master that technique. So anyway, I’m
not going to get into deeply, but the book’s wonderful. It’s really, really approachable,
and there’s just some really good fundamental things that have sort of changed my way of
dealing with those moments when I race  towards bad thoughts, how to deal with those in a
practical way. Anyway, those two books I highly recommend. S1 64:39 This is my first time asking this
one. Do you make your bed? S2 64:44 No. I sometimes throw my bed. Like,
I kind of just flop the sheets so it looks made up. But no, never been into that. S1 64:57 Just, one of these things I’d heard
over and over again is, like, “You should make your bed,” and I started doing it. S2 65:06 It’s like a thing you just– S1 65:08 It’s one of these things I never
did when I was a kid because it was like, “It’s such a waste of time, mom. I’m not going
to make my bed.” S2 65:12 The reason why I don’t do it is because
I don’t like made beds. When I go to a hotel the first thing I do is I tear the bed up.
I don’t like them– S1 65:20 I kick sheets from under. I hate
having my feet trapped. S2 65:22 Me too. I don’t like things tucked
in and tight that way. I like it to be semi-presentable on a certain level, but I don’t  go through
the details. I certainly don’t tuck things in. S1 65:34 Yeah. You maybe flatten it out a
little bit or something. S2 65:36 A little bit. Sometimes, but not
all the time. S1 65:38 So it’s not all just a bunch of– S2 65:39 A flop. Yeah, floppy. S1 65:41 Yeah, just flop it. When have you
left money on the table? S2 65:49 All the time. S1 65:50 And what did you get in return? I
guess the question I’m really asking is, what sort of values have you guided– because money
is a certain value, and then there are other values. What are the values that have guided
your decision making? S2 66:06 I’ve never ever been someone who’s
been interested in squeezing the last dime or penny out of anything. I don’t find that
to be interesting at all. I don’t find extreme optimization to be interesting, like, “How
can we move the numbers by .5%? Because there’s money out there that we’re not–” That doesn’t
do it for me, and also I feel like there’s a moment where – this is very non-scientific
– you’re doing well enough.  It’s about enough. And we continue to make efforts to grow the
business revenues, and we always have every year. Our revenues are higher than the previous
year. Our profits are greater than the previous year. I’m a fan of that level of growth, but
I’m not a fan of trying to bust our ass to make 10% growth if naturally we can just do
8. If we can just do 8, I just don’t need 10, you know what I’m saying? I just don’t
need that, so– S1 66:57 That last 2% is what ruins your life
[chuckles]. S2 67:02 Exactly, and so I’ve just realized
that, “Hey–” I’m just making numbers here. “If we can do 5% growth, I’m actually pretty
happy with that.” We do more than that, but what if we did just do 5% every year forever?
That’s pretty damn good still. That’s wonderful. Fine. What if we could do 20% with a simple
change? I’d love that, but I’m not gonna bust my ass to try and go from 5 to 6. That just
doesn’t interest me. So those kind of things don’t interest me. What interests me is having– 
I do believe in creating cushion. So I do like to have room. I don’t like to feel like
we’re so tight that payroll would be a problem. That is something I’ve never had to deal with,
and I don’t want to deal with that. So I always want to create very healthy margins and lots
of room to try to experiment and not struggle through those things. I’ve always worked that
way, but I’ve never looked at the numbers and felt like I need to move the numbers in
a meaningful way by squeezing. So I’m not a numbers-driven CEO in terms of like, “There’s
got to be a way to pick up more,” but I’d also think that there is plenty more to pick
up, and I’m interested in picking it up as an exercise, but not because I feel like we
must. That’s kind of how that happens. S1 68:32 What do you feel  like you get in
exchange? S2 68:33 By the way, I’m also big fan of just
profit. So getting back to that, numbers for me have never been about top line growth or
revenue. It’s about profit, because profit to me is food, air and water for a company
and it allows the company to continue indefinitely, and that’s sort of what I want. Revenues do
not do that, profits do. So I’m very big in the profit generation and not just trying
to grow. Companies are like, “I want to get to $700,000,000 in revenues so we’re worth
$44,000,000,000.” If they’re only making $3,000,000 off all of the effort that goes into making
[?], that doesn’t interest me. Anyway, that was just an aside there, but I forget what
else you were saying. S1 69:15 What do you feel like you get in
exchange for leaving that money on the table? S2 69:19 A lot less stress. A lot less worry.
Those things. And also just, I think, time back, and also a focus on more important things,
like taking care of people.  We do a lot of really interesting things for employees
here that, if I was financially driven, I couldn’t justify these expenses. We do some
very expensive things for employees. Above and beyond salary, above and beyond benefits,
but just other things. I don’t need to go into them specifically, but they don’t make
sense from a financial standpoint, but they make sense to me as someone who wants to create
great experiences for employees who spend their days working for me and I get to work
with them. So those are the things you get when you don’t worry about those other things. S1 70:16 Do you have a final message for our
listeners? Any parting words that you’d like to give them? S2 70:22 Well, tell me about the listeners.
Who are the listeners? Tell me about the audience. S1 70:26 The audience. Well gosh, I don’t
know. You’ve really stumped me with that question, Jason [chuckles].  You know, I’m bringing
in people like you, and the reason why you’re going to be the first guest on this podcast
is because you’re somebody who has played by your rules and you have very clearly worked
to achieve your own definition of success, which the evidence abound in this interview,
I think. I’d like for people to see, through you, parallels in their own life. Not for
them to do the same thing that you’re doing, but for them to give themselves permission
to listen to whatever contrarian voice might be in their head or whatever new way they
might have of seeing something, and to give themselves permission to go forth with it. S2 71:22 If that’s the sort of the goal of
the show, I think the most important thing – and it took me a while to realize this in
my own life – is just to be completely true to your self and recognize  that you’ve got
to get to know who you are and then you’ve got to just live that life. I don’t mean give
up. That’s not what I mean by, “Just live that life,” but what I do mean is that if
you believe in doing things your way and it doesn’t compute with the rest of the world,
do things your way, because you know yourself and that’s how you want to live. If you want
to take a certain chance and everyone else thinks you’re crazy but you believe in it,
then do it. You really have to get to know yourself and answer to yourself, versus letting
other people define your own limits and your borders. It’s a little self-helpy, which I
don’t like about it, but it’s really true. You’ve got to get to know yourself. Something
I hear from people when I speak, they’re like, “Oh, I want to be like you guys.” I’m like,
“No, you don’t. You want to be like you.” You want to be like you, because  acting is hard.
Acting makes you have to hold a bunch of things in your head about a different state of the
world that is not natural to you. Once you stop acting, then everything becomes a lot
easier. You may succeed and you may not, but at least you’re being honest and true to yourself.
That is the most important thing. S1 72:49 I can totally relate to that because
I know, sitting across from you, you’re somebody who I followed online for so long, and I was
always watching what you were doing, and reading what you wrote and things. Eventually I had
to find my own way of doing things. I know I’m not Jason Fried. I’m not going do things
the same way that Jason Fried does things. S2 73:08 Yeah, and you shouldn’t. You shouldn’t.
You should do things the way you do things. I think there’s a lot of copying in our industry.
I think there’s a lot of people who try to be someone else. This is probably not even
just in our– I think this just in the world, right? I think the earlier you realize that
acting and playing a part is really  hard but being yourself is really easy, then you
should take the easier road. There’s nothing wrong with that, and it’s actually the more
honest road, and I think that you’ll ultimately be happier at the end of the day. So that’s
my advice to people. S1 73:43 That’s great parting wisdom for everybody.
Thanks so much for meeting with me. It’s been a huge honor, and I think it’s going to be
a huge help to a lot of the listeners out there. Thanks so much. S2 73:54 Thank you. Let me say this, too.
I think your show has a lot of legs, because you’re a really good interviewer, and you
have really good, deep questions and original questions. So I’m really excited to hear all
your future interviews. S1 74:05 Hearing that from you is fantastic.
Thanks so much, Jason. S2 74:08 You bet. Thanks. [music] S1 74:17 So there we have it. Before I go
I’ve got to ask, do you like books? If you do, I’d love to send you my book recommendations.
About 90% of them will be nonfiction on subjects spanning from biographies to neuroscience.
Just go to kadavy.net/reading/, and make sure you put one more trailing slash on the end
of that URL. Sign up, and you’ll get my first set of recommendations right away. You’ll
be supporting this show if you buy any of those books through the links in the email.
This has been Love Your Work, and I’m David Kadavy. The theme music for this show is See
In You, performed by the Album Leaf, courtesy of Sub Pop Records. Love Your Work is a production
of Kadavy Inc.

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