Build and Learn

In this episode, we talk with Chris Oliver about his deliberate approach to building GoRails and his other businesses on Rails. In a tech world that only seems to be moving faster and faster, we discuss the slow and steady path he has followed to create a fulfilling life for himself and his team while shipping awesome Rails things for his customers.

Some links to things we discussed:

Some of the things Chris and his team work on:

What is Build and Learn?

A podcast about software development and developing ourselves as software engineers. Hosted by CJ Avilla and Colin Loretz.

CJ: Welcome to Build and Learn.

I'm CJ

Colin: And I'm Colin, and today we
are hanging out with Chris Oliver.

Welcome Chris.

Chris: Hey, thanks for having me.

Good to see you guys.

CJ: You too.

I, I think we should probably
just run down the list of all the

things that Chris works on in case
you don't if you haven't already.

Chris: all that?

Colin: Do you have time for all that?

Chris: Yeah.

It doesn't feel like it.

Some days

CJ: I mean, the, the biggest thing right
now is that you've got a baby, right?

Which is like taking all of your sleep.

Chris: That's been, it's been wonderful.

But yes, it is very, he's been a
really good baby though, so like,

I feel like he sleeps really well.

He eats really well.

He doesn't really cry that
often unless he's hungry.

Or, like yesterday he got his shot, so he
was like quite fussy compared to normal.

But you know, I think
we've been very lucky.

He turned seven months old today actually.

CJ: Okay.

Chris: I'm enjoying it, but it, it
does take like the routines all change.

So like in the morning, get up,
feed him, change him, take him to

daycare and like that was my prime
time for recording videos and stuff.

And now that's gone.

And then some days I gotta pick him
up from school early cuz like, he

got his shot, so he had a temperature
yesterday and they were like, oh, we

gotta send him home just to be safe.

And I'm like, Ugh.

So now I gotta go take out an
hour of my day in the middle

of the day to go get him.

And then I've, I haven't been home the
rest of the day, so it's not like I'm

be doing much recording then and stuff.

So it's, it's definitely squeeze work
in where you can find it now, but at

least like I work for myself and I
can, I can work weekends or nights

or whatever, you know, works out.

Colin: sounds like a little bit of
a forced work life balance though.

You got

Chris: Yeah, it is.

Colin: gonna happen.

Chris: It is great.

It's also been, you know up until February
of this year, it was me and Colin,

Colin started in January of last year.

So 2022

Colin Giber yeah, he, he was the first
employee last year and then in February

this year ended up hiring Kent and
Andrew, and so now we're a team of

four, which was like a much easier
decision cuz like in the past I was

just kind of like, well, there's more
support, I'll just like do it and.

I had some time and it wasn't a big deal,
but now it's like I have way less time,

so time to like reinvest the money into
the, the business and grow the team and

it'll take some time to train them and
me to learn to be a manager and whatever.

Like I'm, I'm doing a very different
job now than I was but still trying to

also do that same job I was previously
doing with recording videos and

maintaining code and projects and stuff.

But you know, it's time
to spread the load.

CJ: is everyone on the
team recording videos?

I know Colin did a bunch.

Chris: Yeah.

Colin's been doing he's been doing
like the entire Ruby for Beginners

series on our new learning path.

So we're trying to give.

Go Rails for the longest time has been
like Rails Cast was, which was like,

here's the feature and we just kind
of jump around to different features

and you know, some of them may be a
multipart thing that's like four or five

videos long, but it was just kind of
like, here's a random topic every week.

But there was a lot of in, in order to
like help beginners more and get more

people in the Rails community, we ended up
like, let's go build a sort of curriculum.

And so we're gonna have like intro
prerequisites which will cover like

Ruby sql, html, C s s, JavaScript,
you know, basics of all those.

Then we'll build, like, I'm in the middle
of recording our second rail series,

which is gonna be building a forum.

We built a blog originally and just did
like all the little things of like, here's

H T D P requests, here's how routes are
mapped, and everything in, in rails.

The forum is like, Assume you
learned a lot of those things.

We'll, repetitively do these things
so you understand it as you go.

But like we will be little less detailed
on some of those and like, you know,

jump into more complex things as we go.

And a forum generally is like a blog, but
there are all these other little nuances.

Like a blog didn't need associations
really, but now the forum needs a

topic in forum posts and categories.

And, you know, you may want to,
like the feature I was building

today was like opting in or out
of a thread to get notifications.

Not one's like, well if you posted.

In the thread, you're by
de facto like subscribed.

But if you're subscribed through
that, then you might want to

opt out, but you also might not
have interacted on that topic.

You just want to see any new posts
so you can opt in and you know,

there's like four different states
or whatever you could be there.

And so we're, you know, eeking our way
into those like more complex topics and

stuff, but start out, do all the basics of
the forum, then like here's notifications.

Turns out they're not as simple
as everything we've done so far.

So, you know, it'll be a
challenge when you get to that

part, but that's the point.

Like, do the repetitive work, ingrain
that in your head and then like do some.

Expansion stuff that's a, a
challenge or whatever for you.

So I've got at least 10 different
projects like that on the to-do list

to do for like Rails for beginners.

And then we're gonna do some other
stuff too, like building products

and integrating Stripe and, you know,
doing more complex stuff and we'll

probably have like three or four
levels of different content for it.

But trying to, you know, give sort
of a curriculum and still also on

top of that, do our weekly Screencast
and maintain Hatch box and maintain

jumpstart and all of the open source
projects too, and is kind of nuts, but,

CJ: Yeah.

That's wild.

Have you ever considered, yeah.

And having a baby, I mean, it's
great that you're growing the team

too, cause that'll take a load off.

Have you considered teaching or like
having a course about building a business?

Like I feel like you've kind of figured
the business stuff out pretty well too.

Chris: that's a really good one.

I haven't thought about doing exactly
that, but sort of in that sense like

because what I want to do with Jumpstart
is like give people more than just

code for like starting your business.

So that would fit in really nicely there.

Cuz I've thought about, like, I've
actually written up, I haven't published

it yet, but, you know, go use Stripe Atlas
and then, you know, go find a lawyer and,

you know, Consider an S corporation if you
don't want, you know, if you don't want

investors, then, you know, just having
sort of like this whole detail thing about

like, make sure you set up an email list
and get people on there and automate the

welcome emails and have, you know, an
evergreen sort of thing going on there

to pitch your product to those people.

And then, you know, trying
to get into all that.

So that would definitely make sense
to do like a course with that.

So yeah, I'll definitely have to
have to think about that and what

it might, what it might look like.

Yeah, I like it.

That would be really fun.

Because I would definitely, what I like
making is stuff like that where I'm

like, I wish I could have bought that
10 years ago when I was starting, if

I could've paid 500 bucks or whatever
for the, you know, complete course on

all of those, like, little decisions
you have to make along the way.

Even little things that are like here,
how do you deal with, with sales tax?

You know, do you even need
to deal with sales tax?

I had no idea, but we can
use, you know, Stripe Tax or

whatever to figure that out now.

Much easier than, I like, read a
bunch of crap on Missouri's website

about sales tax and was like, well,
if it's like they don't charge sales

tax for Netflix, go Rails is pretty
close to Netflix, so I assume I don't

have to charge sales tax in Missouri.

And like, they eventually sent me a
letter in the, in the mail that was

like, you owe us $5,000 or something.

And I was like, for what?

And then I had to call them and they
were like, You know, you explain your

situation and they're like, yeah,
just send us a note that this is why.

You know?


And they, and they basically just do
that as a tactic to scare you and, you

know, taking it seriously and stuff.

But they like estimate what
you probably would owe.

And I was like, oh God,
I don't like have $5,000.

And I was like, and also I'm pretty
sure I don't, I'm not supposed to.

Colin: I would pay attention to that
cuz states are becoming aware of SaaS.

The opportunity of sas and
they're starting to come after,

even down to the state level.

I think it was Chicago that is now
doing like a, I don't know if it's,

you have to have customers in Chicago
or if you're based in Chicago.

Transistors running into this
because John Buddhas in Chicago.

And so part of the
transistor team is there.

And so Justin Jackson has a whole
bunch of episodes on their podcast.

Build Your Sass about the trials
and tribulations of just trying to,

just trying to stay on the right
side of the line is so difficult.


And you don't know what you don't know.

And so like having that, that
bulleted list of, you know, this

is how Jumpstart recommends you
run your business would be pretty


Chris: Yeah.

And a lot of that too, you can rely
on, you know, if you have a good

accountant, then they will know
somebody who's a good lawyer for tax

law and, you know, can refer you to
somebody to get advice and whatever.

Cuz we had them reach out again, I think
it was, and it was like, or no, when, when

we launched Jumpstart, my accountant was
like, Hey, let's just go talk to a tax

lawyer and have him look at your product
and like write up whatever document.

And it was basically like, you know,
this is not taxable in Missouri.

And if.

There ever comes contention with the state
of Missouri than like the tax lawyers.

It's, it's on his shoulders.

So you're basically paying him like a
thousand dollars for insurance to protect

you in case something does happen.

So it's like, if he made a mistake
then okay, then he will deal with it.

But we.

You know, just paid, we paid a thousand
dollars for a document for no reason,

unless something becomes a problem
in the future, which it shouldn't,

but it better safe than sorry.

And, you know, you're on the,
the right side of things there.

But yeah, it's a pain.

When Colin Gilber join, he's in Louisiana.

So Louisiana has different
laws and so we have to collect

sales tax for just Louisiana
customers, for just some products.

Because not all digital sales
in Louisiana are the same.

So a platform is a service like Hatch Box.

Not sales taxable, but like
Jumpstart is to Louisiana customers.

And then also he lives in a, not a
county, but a parish in Louisiana.

They have their own sales tax there.

So you gotta do it on the state level
and the county level or the parish level.

And some states, like you mentioned,
Colin, that are like where you're selling

to, not where your company is based,
they want to collect sales tax too.

So technically there's a lot that.

Even like having one sale in the
UK or in Europe or whatever, can

like put you over the threshold.

And so you're supposed to do that and
it just is making it awful for like

entrepreneurs because you're gonna have
to have just like a, you have to use

something to help you because there's
no way you can like do all that work

because you're trying to make the
business and make a salary period.

But it's like, oh, great, now you
have all this overhead to even begin

before you can make your first dollar.

You'll have to like figure out all that.

It's just, it's I don't know,
barriers to entry that are not great.

Doesn't really encourage people to
create their own companies or anything.

It's not good,

Colin: It sounds like a good business
opportunity for somebody out there

if anyone's listening and wants
to pull up their sleeves and get

into tax.

You know, I mean, a new
government would be useful.

I mean, we, we are like 50
unique countries, right?

As the United States.

It's like we, CJ and I ran into
this when we were doing e-commerce

with, I mean, it's a physical
product, but it was a subscription.

And are you in Nexus or are you not?

And do you use, which vendor do you use?

This was pre-trip text too, so it
was like, you know, which other

a p I do we have to pay for?

And I think Justin concluded
there wasn't really a good

bulletproof service for this yet.

So it's an opportunity
out there for somebody.

Chris: Yeah, yeah.

Stripe Tax was probably the easiest piece
for me cuz I went in and created the

products and then like read through all of
the options for what tax category it was.

And then I found ones that were
like, platform is a service.

That's pretty much what Hatch Box is.

Just select that and then like,
okay, now I know in the previews

it would show like zero tax from
Missouri, whatever for Louisiana.

And you know, any other future states
we have added, it'll show that.

And I would just kind of know
where before I was like trying to

read the Louisiana, you know, law
rulings and whatever for stuff.

And it's like, good luck, you'll,
you will never find what you want.

Or you might find what you want but you
can't understand it because it's written

in some obscure language, legal ease.

CJ: Yeah.

Need some chat.

G P T to translate it
into simple whatever.

I, I remember when I was working outta
the collective Colin, a Anne, like, sat

down with me and like helped sh you guys
have like a bunch of cheat sheets and

stuff for getting hooked up in Nevada.

That was pretty cool.

I don't know if that's still like a, a
thing that you offer at the collective.

Colin: it, it's something we
should do more of for sure.

It, it's one of those things where,
I mean, I didn't expect that we were

gonna, this is, this is the tax episode
for everybody who is just joining us.

But even with the co-working space,
we're a weird one where like every

time we had to switch accountants for
filing our taxes and they were like,

you guys are passed through income.

And I was like, if you change our.

Our income to pass through.

Like it affects us in such a weird way
and we're not passed through income.

Like a co-working space is not
someone buying property and

then renting it out to somebody.

We, it's like a whole
service on top of the space.

And there's obviously like, Probably
a spectrum of co-working spaces

where some of them just rent
to somebody and call it a day.

But like, we have a team, we have a
whole bunch of services and things

that we offer, including like
what you were just talking about.

So, you know, I was like, this is how we
should be classifying our, our revenue.

And the, the accountant wanted to
fight me about it, and it's like,

we've been in business for 13 years.

We are not doing this every year
that we have to file our taxes.

We did this then.

And you know, even the city was like, we
don't really understand what you do here.

And it's like, okay, let's,
let's make business a little

bit easier for everybody.

I, I know every new Secretary of
States, like, we're gonna make

government better for business,
so let's, let's actually do that.


Like better websites, better like,
let's get an a p i for all the

State Secretary of State websites.

Like that's, that would be, you
know, in 2023, you'd expect that

Chris: It'd be written
in like soap though.

Colin: it would be, yeah.

Like can we just get a web hook?

Can we get.

CJ: Yeah.

I think like co-working spaces are
pretty, pretty new, like and also a

lot of the companies that are being
created with tools like Jumpstart are

kind of like, a lot of people have new
ideas and so sometimes they don't fit

nicely into these tax rules, whatever.

And I heard this quote on a
podcast recently and I thought it

was really funny and it's that.

We have paleolithic emotions, medieval
institutions, and God-like technology.

And I just think about this all the
time with like these politicians

who are these old, you know, crusty
people who lived in a completely

different era than we are right now.

And like, just the thought of them
trying to regulate something like

AI or regulate something like, like

Chris: Yeah.

Like that interview with the
TikTok ceo, that was like, the

guy was asking about like, do you
have access to my home network?

And he was like, well, duh.

Like it run, like if you're at home.

And you have, how do you think
you get internet at home?

Like it's on your home network.

That's what that is.

And it's just like, yeah, how, how could
they possibly, well, and you read some

of those, some of those tax categories
are hilarious cuz it's like this one

really obscure little one-off thing
and you're like, why is their sales

tax for like chocolate chip cookies
in this one location or whatever.

It's like some weird thing that happened
and, and then there's like just these very

vague like electronic service and you're
like, well, I don't know, maybe that's it.

But yeah, it's a, it's a mess.

Everybody in governments like super
old, don't really know technology.

We don't even know a lot of the
stuff that's going on as people.

It, like, we do one thing, but it's not
like, you know, all the stuff that's

going on in tech, there's just too much.


CJ: Our, yeah.

And our kids are gonna have to grow
up in like a completely different,

they're, they're already growing
up in a completely different world.

I'm looking over my monitor at my son, who
is building a Google sheet of components

for his own, like custom PC build.

And he's using Bing, g p t, like,
to confirm the, like compatibility

of different components.

So as an eight year old, he's able to
like copy and paste from e-commerce

websites to tell like, is this
a TX board compatible with this

power supply compatible with this

like ram?

And so like this is, this is like a
thousand times in the future or like,

you know, a thousand steps in the future
from where I was when, when I was eight.

So like, this is, it's it's moving
at a pace that's just like yeah.

I, I don't know how
government is gonna keep

Colin: we're just gonna have to, we're
gonna have to get into politics, guys.

We're gonna have to,

CJ: Yeah, I mean, I, I almost wonder
like if I'm already outta date, you know,

like there's, there's a few things where
I'm like, okay, I, I feel like I missed

some stuff with that whole crypto wave.

And there's definitely some details
in there where I would not have an

informed opinion about how to regulate
it well, and so like even I, as you

know, I'm in my thirties, like I
already feel uncomfortable about making

policy around those, like, new things.

And so, yeah.

I don't even know.

Colin: I think that's a, that's
a good baby step from eighties

though, like eighties to thirties

CJ: True.

Colin: you, and you have
this learning mindset.

I think that's the difference.

It's like we, we learn these
tools, we play with them, we.

There needs to be a way to, to, to
think about those kinds of things.

I really like, like the 18 F, which
is the digital service as an option.

They are not big enough to deal with all
the government tech problems that exist.

Like I think they've started with
just making the websites accessible.


Which is a big.

Pain into itself.

But here in Nevada, they're like, they
spent a lot of money on this new, like

all-in-one business platform thing.

And it is garbage.

And I will publicly say that any
day they are now talking about

doing an R R F P for redoing it.

And I'm like, how much
money is allocated for this?

And either a, can I bid on it

Chris: Yeah.

Colin: I, like, I have a whole bunch
of accountants and bookkeepers and

businesses that we've seen the problems.

We know what needs to be


Or like, are you gonna have a transparent
process for picking the next person?

Because it's like, is it just
to rebuild the current one?

Is it to refactor it?

Is it to start new?

Because we all know what happens
when you try to do a full rewrite.

Like we're gonna lose a lot of the context
that happened in the first one, and no

one's gonna know why the thing exists.

And they're like, oh, why
does this thing do this?

It's like, oh yeah.

Some random weird rule
in some county somewhere.

Chris: Yep.

Yeah, there's, have you guys watched
that movie war Dogs or whatever, where

it was like, where like they have the,
the government contracts that they're

like, we just need to buy like a thousand
Berettas from anybody, and like anybody

could submit a proposal and they start
like selling random stuff and whatever to

the government and making tons of money.

It's, you'll have to

Colin: I'm gonna have to watch

Chris: you can be the next war dog.

CJ: Yeah, it's pretty funny.

They've also, there's like a, there's
a book too that they one of them

wrote I have a buddy that, that works
for a government contractor, and we

used to talk about this all the time.

Like, we should just submit for government
contracts to like, make screws or

Colin: give more
governments on rails, right?

CJ: Yeah.

I mean, I'm sure

there's tons and tons of

Colin: jumpstart, government,

Chris: you

CJ: Yeah.

Solving all the, all
the world's needs here.

Colin: just a little bit
of device and you know,

a little bit of

CJ: when you, when you deploy with Hatch
Box, like have you run into anything where

people have to be like HIPAA compliant
or have like any like crazy compliance

Chris: People have asked and
it's pretty much like, we're

not gonna be HIPAA compliant.

I'm pretty sure like, it's
such a vague set of rules too.

It's like hard to know that
you're really compliant.

So you probably need to go through some
company that can certify that you're

actually HIPAA compliant and stuff.

And it was like, I'm one person you
know, I don't need to do this for

a one-off customer, unfortunately.

And like a Heroku, I, I looked
into it at one point cuz a couple

customers had reached out about that.

And I was like, looking at Heroku's.

Version is like, starts at $2,000 a month.

And I was like, oh,
that's that's tempting.

But it kind of brings you back to
like the points that like Basecamp

has made where they're like, we
don't wanna make a oversized amount

of money from one or two customers.

Cuz if they ever leave us and like
our business goes out the window, like

we lose half our business or more.

And then what do we do?

And we gotta fire all
these people or whatever.

Like we're we're un like diversified.

So that was kind of the same thing where
I was like, you know what, we could end up

with a few customers that are paying us,
you know, most of our customers are pretty

small, under a hundred dollars a month.

And then you come in with a couple
that are like 2, 3, 4, $5,000 a month.

And then if they disappear it's like, oh,
that's a lot of customers to replace them.

Colin: Or they start
throwing their weight around,

Chris: yeah.

Colin: Like they have other
requests that you have to do cuz

they're paying you more money.

Chris: And then it's basically you're
a consultant company for these two,

three big customers and you're not
really running your own ship anymore.

You're just getting
dragged behind their boat.

And it's like you're not
really independent anymore

running your own company.

CJ: Mm-hmm.

Chris: that's pretty much where I left it.

It was like, yeah, you guys are
better served at Heroku or whatever,

like, we're not gonna provide that
much better of a service or whatever.

But yeah, somebody was trying to
use AWS gov cloud and other things

and like, cool, but you know,
it's, it's just not worth it.

So I'd rather and I like helping the,
the small like Jason Fried and DH h

just post like tweets and blog posts
about like helping the underdogs.

And I really like, I like that a lot.

I want to help the, that's why Hatch Box
and Jumpstart and Go Rails all exist like.

And rails, I feel like is why I'm, I like
Rails and Laravel and things like that

because it does help the underdog succeed.

And it can be one or two
people building cool stuff.

And like, you know, even if they don't
build a company that can employ 50

people, who cares if they ever like
having a wonderful living by themselves

or with a small team, they win.

Like, that's amazing.

That can be life changing.

So, you know, they're the
underdogs and I really enjoy

that sort of, that sort of stuff.

CJ: Totally.


I think that that was one of my
favorite parts of my job at Stripe

was just helping people earn their
first, like money online is, I think

that was, it was so, so powerful.

Chris: this is the best
feeling in the world.

Like, I, I tell the story
regularly, but like, I with a

friend built this little not so.

Not so like compliant with the
Apple terms of service, but he was

like buying these templates for iOS
apps for like a Flappy Bird clone.

And then he changed the graphics
and make it like Flappy Panda or

something stupid thing and like
put his add network IDs in there.

And then the only way he could
actually make money was like

finding people to review his game.

So it got rated in the app store
enough to like get some downloads

and get some people playing it
and get, you know, ad views.

And so he had these Facebook groups who
were, people were sharing their apps

with each other and reviewing them.

So we like built this little rails app.

And you would pay $5 for every
app you wanted to put in the pool

and then you would review other
people's, and yours would get.

Pushed up the queue, so then other people
would review yours first and then you

get this little review group going and we
made like 30 grand on that, but before it

kind of got shut down by Apple and stuff.

But it was like the first time we made
like $25 and I think you, we had just

used PayPal for it back in the day,
cuz this is a pretty long time ago, but

I was going to the movies, I sit down
and it's like, turn your phone off.

And I like opened my phone and I
see a notification that I just made

$25 and I was like, wait a minute.

I didn't do any work.

And I'm the movie's free.

Like what?

This is nuts.

And like I was, you know, always
trading time for money until that point.

And then I was like, oh my God,
like I'm sleeping and I woke up

and I made a hundred dollars.

Like, what is this?

This is insane.

So that, yeah, I, that feeling is wild.

If you've never experienced
that before and you like wake

up and made money, it is insane.

And that's, I want as many people
to like experience that as possible.

Cuz it, it starts to really just like
change your, per your perspective

or you're not, You're not trying to
do things trading your time anymore,

which has like a natural limit.

You can only work so many hours a week
and you're only gonna ever be able

to charge so many dollars per hour.

Like as a developer, you might
get lucky and be able to charge

two 50 an hour or something crazy.

But you can still only
work 40 hours a week.

So like you're limited there.

But if you're doing something like our
Screencast at Go Rails, like I can make

one video, 10,000 people could watch
it and pay 19 bucks a month for it and

like, I only had to do it one time.

But that same value was able to
be like reused for everybody.

So it just like starts to.

Open your eyes to those, like
those business ideas that are

scalable like that or whatever.

And then, then you start to realize like,
that's where people really make a lot.

They like figure out something
like that that can be done

without trading time for it.

Colin: I have a follow up on that that
I'm curious about because I'm like

having previously been a consultant,
like you become habituated to trading

time for money, and I know people who
start to think about their time as money.

And so now that you've kind of
disconnected your time from your

money, like do you ever find yourself
like thinking about like how much

like, oh, I just spent eight hours
on this and I could have been made.


have you been able to
separate yourself from that?

Chris: So now, we built our house and
we have a lawn now that I have to mow

that takes a lot longer and we have a
pool that needs maintenance every week

cuz we got trees around and it's like
random leaves and other crap and frogs

and I found a turtle in our pool and
whatever, and it's like, okay, if I was

doing all of that, I'd have to spend four
hours on every weekend mowing the lawn.

I'd have to b be spending at
least that during the week, like

cleaning the pool and whatever else.

So like I've started very much now being
like, all right, I can pay somebody to

do that, get that time back and I can.

I can choose to spend that time
trying to make more stuff, or I can

like spend that time with my son
or whatever and like, choose that.

That's like a, I'm gonna pay the money
so I get time to spend with the family

instead of like, okay, it's worth this
much money and I could go back and

like record another course in that
eight hours I save every week and like

in the three months maybe, you know,
publish a new course or whatever.

Sometimes I think about it that way.

It does help me rationalize, like
spending more money on things.

But you also like, at a certain
point probably make enough

money that you can do that.

And so it's like, it's, it's
one of those benefits where it's

like if you, once you get to that
size, you're like actually now.

I'm making enough money, I could just
shovel it into savings or whatever.

But why don't, my parents were always
really bad about this, like saving

money and not actually spending it
to enjoy their life in the moment.

They're always just saving it.

And then like my dad had colon
cancer years ago, and it was like

all of a sudden he almost died.

He's recovered and he's fine now,
but like he almost died and they're

like, Holy crap, life is short.

We actually need to, like, we've been
talking about traveling, like we've

been, never been to New York City.

Like we should go do that.

It's not that expensive.

Like, why didn't we never do, why didn't
we never make the time to do that?

So they like are doing those things
now and like it was great for me

to see that when I was younger
and be like, yeah, what the hell?

Like, I'm 25, my dad almost died.

I don't want to like be 50 and then
regret that I didn't do those things.

So, you know, like I'm just trying
to spend as much time as I can

with my son when he's little and
I don't want to be the dad that's

like always working and whatever.

So yeah, it's, it's, you know, a tool.

That's how I try to think about
it now is like the money's a tool.

Allocate it where you want.

You're in a here in tech, so chances are
you'll never really have a trouble finding

another job in like worst case scenarios.

So it's not like you have to
shovel everything into retirement

and be scared about it.

But you know, you should still do
some of that, but you should also

enjoy your life in the moment too.

But what are you gonna say, cj?

CJ: Oh, well the first thing I was
gonna say is like, soon enough,

your son, you could just make him
mow the lawn and clean the pool.

But also like,

it's like, yeah, I mean, that's
gonna be a few years, right?


The other thing before I forget is I want
to, to recommend the Die With Zero book.

It's so good.

And like, the whole point of the
book is basically like, try to Yeah.

Like squeeze every ounce out of your
financial life as possible so that

you don't end up like, with a bunch
of money in the bank dead and like

not have any experiences or whatever.

Obviously you gotta like,
have a balance, but,

Chris: Yeah, you, you need to be
able to retire at some point, so

you need some retirement money
and it's good to plan for that.

But it's also like you might
not make it to retirement.

And then what was the point of having 5
million in the bank by the time you're

78 and you can't use any of that cuz
you're stuck at home or something.


Colin: And you didn't experience
any of those things that

you wanted to do, Right, You're like,
oh, only when all this stuff is super

perfect, I'll go take that vacation and

Chris: Yeah.


My grandparents did that and they went
to like Russia and stuff, but as they

were after they were retired, so it was
like they couldn't really walk very far.

And you know, just, and my grandpa was
a farmer so he was like beat up from

doing all the stuff outside in the
farm for years and years and years.

And my dad's kind of the same way.

He's got a bum knee and whatever
from doing all that too.

And I'm like, you know what?

It makes it.

Virtually impossible for you guys to like
go explore cities now without like, you

know, riding in a car to go around a lot.

And I'm like, I want to go wander around.

I had the most fun wandering around
like New York City and just any place.

So it's like, do it now while you can

CJ: Mm-hmm.

Chris: your kids on those
experiences, cuz that will really

like open their eyes to things.

CJ: It totally changes your perspective
too about when you think about

how, oh, in the future things are
gonna probably cost way more money.


And so you think, oh, maybe like over
time my expenses are gonna increase.

But the counterintuitive reality is that
as you get older, you can't actually

spend the money as easily because,
because of these physical limitations

that your body has as it's breaking down.

And so like when you are in your fifties,
you'll be able to spend a lot of money,

and then you'll be able to spend less
in your sixties, even less in seventies.

In like, like even less in your

Chris: Your healthcare expenses
through the roof, though,

CJ: True, that's true.


But like, yeah, if

Chris: at least here in the

CJ: fixed income Yeah.

Stuck in, stuck at home or
whatever, and you're not actually

going, going anywhere, like,

Chris: Yeah.


it's it's one of those things
that I was like always.

Every time I had a job with a salary,
I was working on the side to like, just

go build something because I knew like
the only real career for the most part

that's uncapped is like sales where
you get basically free reign to make

as much money as you want, as long as
you bring in the business and whatever.

Then you get paid the commissions and
stuff and you, you have no real cap.

You, you have sort of a minimum, but
it's kind of like being a, you know,

a bartender or waiter and it's like
you get this like really, really low

salary or minimum wage and then you,
you're free to be as charming and you

know, as good as you want at the job
and you can make as much as you want.

And that doesn't really generally exist
in a lot of software developer careers.

You got a salary and, you know,
they, they can't tie your work

directly to revenue that comes in
like they can with the salesperson.

So it was always like interesting to me
to like, At least do consulting instead

because then I could choose to work my
butt off and do quarter million a year or

half a million a year or something crazy.

Cause it was entirely up to how
much time do I put in, how good

can I be at sales and actually
get the work done and everything.

And you know, sky's the limit, but
at a certain point you're like, well,

I can only do so much as one person.

And like in the past couple years with Go
Rails, like I've been on my own for what,

seven, eight years when Colin joined and
it was, it, it was coming to the point

of like, I'm burning myself out trying
to do all this work myself, but I've

kind of hit my natural limit of, and I
had a chip on my shoulder just to figure

out like, how far can I get by myself?

And it was like, Crazy numbers, you
know, per year, but with one person.

And I was like, this is sweet,
but this is also unsustainable.

Like this is great.

But then you get to a point of now your
decision is, do I shut things down and

stop and cut things out and get my life
back, or do I change what I do and hire

a team and we continue building stuff.

And you have to think too, like,
I've been doing this for eight years.

Do I want to do this for another
eight years or 20 years or whatever?

And I'm not really bored of building
stuff and rails and, you know,

helping the community and whatever.


The, the appeal was more to like, well,
I guess if we have a team, then we can

do more stuff and we can accomplish
more things and contribute even more.

But if I, like, am just myself, I gotta
shut things down and like simplify and

like, just focus on the, maybe the stuff
with the best roi, which maybe isn't the

thing that helps the community the most.

And so it was kind of like conflicting
itself if I was to go that route.

So I ended up like, all right, my job's
gonna change, becoming more of a manager

and you know, a leader in the company.

But also it might make the business more
like sellable in the future where it

was a hundred percent dependent on me.

I now have really an asset that I could
sell, that someone could take over.

They could hire teachers and
record stuff and keep doing the

Go Rail screencast and like, this
is now a business that's not just.

Me that isn't really valuable for
anybody else unless they hire me as

an employee, which would not work
because why would I want to do the same

thing for somebody else if I'm already
doing it for, for myself, just fine.

So that was, there was a lot of
different decisions there in the

last couple years that made it,
having a kid makes it very obvious,

like, which path you want to take?

Because I just kicked the can down
the road for like five years just

thinking about like, what do I do?

I don't know nothing.

There was not enough pros or
cons for one way or the other.

I'm just stuck in a limbo of like,
comfortableness where things aren't

so bad, you have to shut it down.

Things aren't so good that you're like, I
am going to just throw everything at this.

I'm just like, ah, just
keep chugging along.

It's, it's going fine.

Keeps growing and you're like in a weird
spot there where it's like things are.


Pretty good, but they're not like
blowing up out of control where I

have tons of money and have to go
hire people and grow the business.

But I al it also doesn't suck.

And it's not a point where
you're like, why am I doing this?

Let's just shut it down
and do something else.

So that took a long time, but I think
it, it eventually got to the point

where it was like, it makes plenty of
money and I need some, some quiet times.

Some like just, you know, share
the burden with somebody else.

You know, and, and so that's what.

I ended up doing in the past
couple years, and it's been great.

It's just now like we doubled the company
from two to four in February and that's

that's a big move, a very big move.

And what went from, like, most of our
meetings in the past were basically like

this where we just hop on two pool and
chat for whatever, like 15 minutes or

an hour or the whole day about anything.

And we always knew what
everybody was doing.

And now it's four people and it's like,
well, you're working on this, I haven't

talked to you for like three days.

And like, it is a totally different
experience now with, with four people.

So I'm learning all of that and trying
to be, you know, cognizant about what

do I need to get better at and how
do we become a well-oiled machine?

And just now you got more personalities
and you know, people with different.

Responsibilities and other time zones
and all these different things to figure

out how do we all work together well
and efficiently and make sure that

everybody has their own space to just
go do work without, you know, like I

need a lot of quiet time to just poke
around at a problem and explore it.

And it may not turn out to be
anything, but you know, I gotta go

just mindlessly think through something
by myself without interruptions.

And that is like a lot more rare now.

So it's interesting to like see
that and maybe over time I'm not

contributing code as much or something.

Or like D HH is kind of like, At
least in Rails as an example, he

like shows up, does a whole bunch of
stuff, and then disappears for like a

year or something and does that again
and kind of like, you know, does it

when it makes sense and whatever.

So I don't know if I'll end up in that
situation or whatever, but it's, it's

interesting to, to go through this change
and actually like, have to grow things.

But I want to keep it slow and, you
know, steady, but, It's it's good.

I think it's gonna be very good in the
long run, but also it's one of those

two where if you make mistakes, you
make mistakes and you can like reset.

It's okay.

Like if you hired people like Adam
Wathan did that for tailwind and

like realized it wasn't working.

He hated it.

And, you know, pulled the plug
and shrunk the company back down

and, and was like I have to, like,
it's my company, it's my life.

I can make it whatever I want.

So if I'm not happy, like I need to
go fix it and just not deal with it.

Like, this is, this is my life, so
I wanna make sure I'm enjoying it.

Colin: We've all had startup experiences
where, if you have investors, you

don't necessarily always get to
go slow and steady like you're

talking about and seeing what Adam's
doing, seeing what you're doing.

Like, I mean we got to
hang out at Rails Conf.

It was fun to see people react to seeing
Go Rails, like you know, the whole

four four of you, it's like you have
a bigger footprint now and honestly

there's some resiliency there too, right?

Like if you were sick, go Rails still
has three people who can work on stuff.

It's not just a thing you can sell,
it's a thing that, you know, doesn't

need to have Chris show up every
single day in order for it to exist.

Chris: I mean that was, that
was just before Rails Comp.

When I went on vacation for nine days.

I didn't touch the computer for nine days.

Like, that was the first time in
probably nine years that, that I had

that long of a stint without working.

It was crazy.

And now, yeah, I got my bodyguards
at Rails Comp and whatever, so,

CJ: Is there, like I assume there's,
there's like a back channel that you have

with all these other business owners.

Do you have like a, a chat thread
going with a bunch of ballers that are

like, oh, what are you doing, you know,
with your marketing this month, or

Chris: a few people, but it's not
really like, and, and I probably need

to make it something more formal like
that, like a mastermind or something

where we either just have a discord
and we just use that, or I don't know.

We've tried, I've tried a few
masterminds or it's like a weekly

meeting or even biweekly and it's like,
I don't know, we're a small business.

A lot doesn't happen in two weeks.

Like nothing major changes that often,
so you really, yeah, it's, it's kind of

tough too, cuz some of the, the learnings
you get from, if somebody's got a company.

That's, say 10 times where you are, if
you're like building an agency, what you

really, you need to be really in with the
person who's like 10 times ahead of you

so you can see like, oh, we're doing these
things and that really doesn't make sense.

But oftentimes, like they're not gonna
get any benefit from talking to you.

So it can be interesting to
try and find the right balance.

Where as long as you can provide
something in return value wise

those really work out well because
you can pick up a lot of things.

It can be not as useful if
everybody's kind of on the same

level and it's like, we're all here.

We're not sure how we get to
there, but here's what I tried.

And they can still be useful definitely.

But I feel like it's just kind of
more like you really want to see the

person who's like two steps ahead of
you, but it's maybe harder for you

to like, Provide anything in return.

Cuz they're like, yeah,
you're, you're behind me.

I need the, I need the
guy 10 steps ahead of me.

CJ: Mm-hmm.

Sometimes it's energy, though, just like

being pumped and like being excited and
talking about new, shiny things, and I

mean, I think that's probably valuable
for those, the folks that are ahead.

Chris: yeah.

That is definitely a lot of fun.


So, yeah, I, I like that for sure.

And it's, it's a way to, sometimes
you just don't have anybody who's

Understands the problems that you have.

Like, okay, if you're worried about
paying salaries, like you can't talk to

employees about that, like you need to
talk to another business owner or whatever

that understands like, oh God, yeah,
we had this issue and like we ended up

opening a line of credit with the bank
to like smooth things out over time.

And it's like, oh, I never even
would've thought that I could do that or

whatever, and that makes a lot of sense.

I'll go do that and try that.

And so sometimes, yeah, there's
really helpful things and just

the energy of like, you have peers
to, you know, vent to, or whatever

it is, be excited with and stuff.

In general, like the education
space is just like rough.

So I feel like that's not everybody
I end up talking to in that,

that's doing something similar.

It's like, yeah, this just sucks.

Have you listened to the hackers
Incorporated that Adam Wathan

and Ben Orenstein are doing,
they're, they nail a lot of those.

Like it feels like they're talking to me
when I'm listening to that cuz I'm like,

everything Adam struggles with basically
doing an education business even though

it's like a open source CSS thing.

It's very similar to what we do
in all the struggles we've had.

Cuz the thing that made Go Rails like
unsustainable for the longest time was

like, oh, I want, people are asking me
to do these videos for these topics.

So I try and cater to those and like, I
don't have any interest in doing like a,

a backbone js and rails api, whatever.

But people were asking for it and I was
like trying to accommodate everybody and

like I'd burn myself out cause I gotta
go teach myself backbone and learn all

the ins and outs and then in 40 hours
still may not really understand it very

well to the point where I can teach it.

Or I might end up teaching it
in a way that's just like really

janky cuz that's how I learned
it from these other tutorials.

And then people are asking you
questions about how, how am

I supposed to fix this thing?

And you're like, I.

I don't know, like I just learned it
last week, you know, as much as I do.

So I have tried to pivot and just like
build stuff and then teach what I'm

building and like that, I'm usually
very excited about those things and

then I can also much more easily
teach that content cuz it's fresh in

my mind as opposed to like trying to
learn something brand new and teach

something I don't fully understand.

It's much easier if you already know
something deeply and go teach it that way.


that's made it, that's made the
whole business like sustainable.

But it sustainable is relative to,
because it's still publish a video every

week and it's, you know, the, the, yeah,
the grind of same, same thing that all

the Twitch Streamers are stuck with.

You gotta show up every night, play
video games for 10 hours straight

and never miss a day and like, That
becomes a job real fast, even though

you're playing video games, it's a job.

CJ: Yeah, I burnt out real hard, just
like making tons of content last year and

like, yeah, I like couldn't do it anymore

Chris: and, and you had to, like, you had
to do that of using JavaScript frameworks

and P h P and Ruby and like you were
doing something that seems to me like

is extremely hard cuz you, you have to
go so broad, whereas in Rails, I can go

real deep on Rails and only care about
Ruby and Rails things, but you're like,

you're deep on stripe, but broad on every
language, which is like crazy to me.

That sounds very, very hard.

CJ: Yeah, it was, it was tons of fun to
learn, like the frameworks and stuff.

And in the beginning I had a blast
just like picking up all the, like the

same patterns in different languages.

But yeah, to your point, I would
make a video in Ruby having fun with

something, and someone would be like,
can you do the same thing in php?


I'm like, oh my gosh.

Like, like, I don't know.

Colin: We need some some elixir.

We need some rust.

CJ: Yeah.



Same Yeah.

All right, well as always, you can
head over to Build and

to check out all the links and
resources in the show notes.

Colin: Bye friends.