292: Josh Pigford — The Open-Source Transformation of Maybe

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Arvid Kahl: Today, I'm talking
to Josh Pigford. He is the

founder of Maybe and he recently
open sourced the whole codebase

for this financial software
tool. He also sold Baremetrics a

couple years ago for $4 million.
So this project now is a

continuation of his interest in
the financial industry and

dealing with money. I talked to
Josh about all kinds of things

about involving people from the
community and building your

product about raising money for
something that could also be

bootstrapped and how to manage
such a thing in a community and

an industry that is usually
pretty slow to take up new

technology. Enjoy this
conversation between me and

Josh. The whole conversation is
sponsored by acquire.com. Now

here is Josh.

Josh, thanks so much for coming
on the show. You've been giving

a building in public master
class over the last few weeks

and I really enjoyed it. Let's
talk about maybe, what is it?

Why are you building it in
public? And why are so many

people so excited about it right

Josh Pigford: Yeah, well, thanks
for having me on. So maybe it's

something that started back in
2021, post exit of a previous

company and we spent the better
part of 18 ish months building

that not in public really,
launched it and found ourselves

in a pickle, where we had gone
the sort of typical VC route,

hired a lot. And then we
launched the thing and

essentially ran out of money to
be able to see it through to

grow it. So we found ourselves
on the spot where we'd be like,

downsize the whole team to like
two or three of us and

ultimately shut it down. And
then a few weeks ago, I got

really nostalgic and decided to
open source the whole thing. And

that hit a nerve and now it's
alive again and we've raised

some more money, but rebuilding
the company differently this

time. But yeah, people are
pretty pumped about Sienna, the

FinTech software, the insides of
it. So

Arvid Kahl: That's the
surprising part to me, too, like

FinTech tends to be a very
closed source ecosystem. And you

just throwing it out there and
open source like, how did you

come to that kind of conclusion
to just throw it out there?

Because you could have done many
different things, right, you get

to just restarted hired
outsourced all that, but open

source, that's a pretty solid

Josh Pigford: I well. So I had,
I really wasn't thinking that

anything. In my head, the the
choice is sort of binary, and

that either this, this stays in
a private Git repo, and no one

ever sees it. The end member had
no plans of reviving it anyway.

And so it was that or make it
open source. And then like,

maybe somebody can do something
with it. And it was so complex,

that it wasn't the kind of it
was, it was never the kind of

thing that I was gonna build,
just grab the repo and like,

deploy it and have their own
version of maybe like we had

sort of over engineered it for a
multitude of reasons. But it

was, you know, even now, we're a
few weeks and have 10s of 1000s

of people like seeing it and
like it still is kind of a

hassle to get it up and running.
So like, it was more of just a

Yeah, I'm curious what other
people will do with it.

Curiosity more than anything.

Arvid Kahl: Yeah, I see you
rehired one of your software

engineers to me, that's so I
love this. I love the cyclical

nature of this. There's,

Josh Pigford: there's more of
that. There's more of that

coming. Oh, wow.

Arvid Kahl: That's cool. I was
reading Sachs tweets about it.

And it was pretty interesting,
because he gave some very

transparent insight into the
back then. And then now of where

the vision goes. And apparently,
he was talking about a lot of

compliance stuff like, version
one had a lot of requirements,

because you had a lot of advice,
financial advice they were

giving. And version two, the
open source version doesn't have

that. Can you just kind of
elaborate on that choice? And

why? Yeah.

Josh Pigford: So when we first
started, it was the impetus for

maybe was, was sort of exited
barometric so that company took

home close to 4 million like me
personally. And so what is the

situation we found ourselves in
was, us, me and my wife was

we've got all this money from
this exit, I want to not blow

it. So I started working with
financial advisor. And that was

the first time first time we've
ever worked with a new advisor

or planner or whatever. So it's
like, I've got this mix of we're

doing this and I have all the
free time in the world. And I

can dig into like, what is what
does a financial adviser do? How

do they grow our money? Um, and
why are we paying them a

percentage of the assets that
they're managing? And so that's

when I like went deep dive into
this, this that whole world

realizing like oh, they're not
doing anything all that great to

warrant taking a percentage of
assets. However, it is nice to

have a third party kind of like
gut check you on some stuff. So

the idea was we'll build this
like modern platform for

managing You're on finances. But
with that will tack on and a

financial advisor as part of
your account. And that choice,

though, meant that we've got an
infinite number of regulatory

things to comply with. And so
that added a ton of overhead, it

meant that we could only be in
the US. I mean, we could expand

other places, but like, we would
have to meet all the regulatory

requirements and all of those
countries too. And so that very

quickly sort of limited us on
sort of addressable market, how

fast we can move on things, tech
choices, because there's things

like we have to keep, and, you
know, an unchangeable copy of

every single interaction for
like, seven years or something

like, there's just a lot of a
lot of tech choices that that

forced. And so that made
overhead very high and text that

complicated, like all sorts of
stuff, but now we're saying

we're not doing that anymore.
There's no advice component, we

can rip out half the code. Like,
that's sort of where we're at.


Arvid Kahl: that's cool. Yeah,
that's awesome. And I think just

kind of shaving off complexity
is generally a good idea, right?

If you want to revive something
that was too expensive to run.

So I kind of I kind of really
appreciate that that logic makes

sense to, do you think that
people are going to build their

own advice systems on top of on
top of this, because right now,

you're kind of just supplying
the way to gather data

Josh Pigford: correctly? I guess
you could, I mean, you know,

there's, it's not in the current
sort of most recent commits. But

like, if you go to the very
first commit of the thing, that

open source a few weeks ago, the
whole like, advice dashboard is

there. So like, you could build
and we had built a very full

featured, a certified financial
adviser could go in, and it's

like a whole thing for them to
manage their clients and

interact with him, like a chat
system, uploading videos and

audio, like tons of stuff.
That's there, if somebody wants

to grab it and do something with
it, but it does, it comes with

regulatory overhead. And at this
point, we're not interested.


Arvid Kahl: that's, that sounds
very complicated. And it sounds

like very hard to monetize as
well. Because you know, that,

that just the increase in costs
and all that, that probably

makes it hard to get a cut how
you're going to monetize this

open source kind of system.

Josh Pigford: so pretty typical.
I mean, you know, the, I think

the example most people would
understand are sort of like,

see, the correlation is like
WordPress, where, you know, it

was wide open source for ages.
And then they did like

wordpress.com. And so you can
have your own hosted WordPress,

essentially the same thing, I
don't think it's a little less,

it's a little more consumer, I
guess. And on our side, where

we're not gonna, like, talk
about maybe is like, get your

own hosted version of like,
we're not gonna use that

language, I guess it's just,
you'll go to the maybe a website

and sign up for an account. And
that's that. But there is, it's

sort of the hosted version that
you'll pay for, will just be the

version that you know, most of
civilization uses. And the open

source stuff is like, it's
available for those that want to

self deploy and all that stuff.

Arvid Kahl: seems to be one of
the few but very promising ways

of monetizing any kind of open
source project, right should

keep you keep the core free, you
keep itself deployable, but you

kind of have these added
services or just the

Josh Pigford: well, there's
things especially in the

financial world, where, you
know, like connecting all your

bank accounts. There's all these
different data aggregators,

plaids, sort of the most well
known one. And very few, I mean,

quite literally, probably 99% of
these aggregators across the

world don't have an option for
an individual to use them. They

just require enterprise
contracts and stuff. So you

know, on the on the hosted
version of maybe that will, will

offer for pay, that will include
those data aggregators, where

you're not having to sort of
manually import CSVs and things.

Whereas a self hosted most of
that will be either manually

inputting data, or uploading a
CSV or something like that. So


Arvid Kahl: there's the upsell,
now I get it, I was wondering

just a little bit where that
value would be of a hosted

version. But of course, like you
having the capacity to get these

aggregators, and I was, I was
thinking a lot about this,

because ever since I moved from
Europe to Canada, like the

automate, automate ability of my
financials has just gone down

the drain. It's like super
crazy, the kinds of standards

that Europe has or Germany with,
you know, the in FinTech, there

are API's that every single bank
has to offer, and you can kind

of fetch data from there does
not exist here. When I go to my

bank here in Canada, it's like,
yeah, you can kind of copy and

paste it from the website, if
you like. It's like, it's, it's

really hard to pull that into
anything else. So how is that

like, you come from a place
where within a day, you can

build something really cool. You
can refactor if you want it to

your whole code base and 24
hours right? Let's go a tweet at

you throw out a couple a couple
days ago. You could and nobody

can stop you. But working with
these banks working with these

particular interstates, and I
guess if you expand to other

places like Canada, with these
very self contained places How

are you approaching that kind of

Josh Pigford: So what we're
working on right now is

essentially standardizing the
data model on our side. And

then, and then everything will
have to sort of meet that. So

like, Will will make it so that,
you know, we build a plan

integration, even just for us to
use, but it'll then have, its,

it'll be sort of self contained,
and then just pull in and

process the data so that it
matches our data model. So, you

know, it ends up being anybody
can build a data source sort of

plug in or something that
depending on where they're

located, or whatever, you know,
eventually this stuff all

becomes like integrated with

Arvid Kahl: that's interesting.
It's kind of like a Zapier for

financial data that

Josh Pigford: yeah, essentially,
it is, it's like, a lot of the

banking data includes more sort
of detail than is actually

necessary for the average sort
of financial application. So

it's like, we can we can
standardize or sort of reduce

the complexity into, you know,
money and money out kind of

thing, in most cases. And it
gets a little bit more

complicated when you're talking
about investments and buying and

selling things and whatever. But
the idea is, we can sort of

standardize all that stuff and,
and simplify the incoming data.


Arvid Kahl: reminds me so much
of that one XKCD, always about

like, there's 15 standards for
this kind of thing, let's just

implement the standards for all
standards. And now there's 16

standards for that kind of
thing. Right? It's fun, though,

I think it's just necessary,
right? If you want to be able to

integrate with all these
platforms, and there is no Core

standard or Central Standard,
you just have to establish an

interface for it. I love the
idea. Because once that is

established, and is also fully
documented and communicated to

your community of contributors,
and people who are interested in

using it, they can start
building these extensions, and

you can kind of add them to the
system as they come. And they

can also be externally
maintained, which is really

cool. Is that like an ongoing
plan to just like, give the

community the opportunity to
keep building and maintaining

these things? Are you going to
pull them all in? I

Josh Pigford: think so there's a
little bit, the only sort of, I

guess, hesitation or risk of
having too much external stuff

is security. When you're talking
about financial stuff. I think

the state like linking out to
stuff that's like, hey, download

this thing that pulls in your
banking data, like, that feels a

little bit feels a little risky.
So yeah, I feel like we would

need to have some sort of, you
know, we have an internally

hosted is set of Doc directory
of plugins or something I don't

know, that's been vetted and
made sure that it's not, you

know, scraping your data or
something. But um, yeah, I don't

know. I think it may be one of
those things that the self

hosting crowd ends up having
their own sort of lots of

plugins to choose from. And this
is kind of the case, again, to

the WordPress example, like, you
can install plugins on

wordpress.com. But like, there's
some limitations to that, right?

Like, you're not going to have
the full breadth of plugins to

choose from. So yeah, I don't
know, we're still that's still

super early. So yeah,

Arvid Kahl: and I would love to
just kind of your brainstorm

these kind of things, I find
them very interesting. Because

when you're, when you're at this
point, now starting just to

build the potential for a plugin
marketplace, if that would even

be the name for it, or just a
repository that is kind of

validated and tested and
secured. Like, there are so many

different ways. If you look at
WordPress, the example is great,

I think you can, you can install
manually, like any plugin

anywhere, it can be locally
installed, but it kind of has to

go to adhere to the
restrictions. Or you can just

choose one of the ones that they
have pre approved, right, that

are securely located in there,
the big list of things that are

wonderful, and you just click on
it, and it's right there, right?

That that kind of duality, gives
you some choice as a platform

maintainer, to just want to
offer and how to secure it that

that's a really cool thing, too.

Josh Pigford: Yep. Well, and
that sort of jumps into another

way that we're thinking about
this. And I've tweeted about

this a little bit like the
concept of maybe being your

like, the sort of OS for
personal finance, where, you

know, internally, we talked
about having apps or modules

such that, you know, you could
potentially build your own sort

of module that's got its own set
of like tools for whatever

specific stage of life you're in
or something like that. I think

we'll have our own stuff that
we're building, but the idea of

being able to create your own
Yeah, watch this thing.

Arvid Kahl: Yeah. And any kind
of standardized interface makes

perfect sense for that. Right.
That's, that's fun. Yeah,

standalone. Absolutely. That
kind of reminds me of a tweet

that you just sent prior to this
conversation about once like the

stuff that Basecamp people have
been doing. Is that kind of the

taste that you have for these
apps just to be just standalone,

instead of being hosted on
something else?

Josh Pigford: Not necessarily. I
am most curious about the ones

stuff from a deployment
perspective, like how easy

they've made it to sort of self
host, in this case camp fire

their first app. I like that
idea, at least as far as some

sort of inspiration around
making the maybe app itself sort

of self postable. Making it
where it's, you know, you copy

and paste this one, literally
single command into the command

line, and then it walks you
through everything else. Like,

that's, that's sort of, to me is
like, sort of the gold standard

for self postable. But also like
modifiable codebase. Yeah,

Arvid Kahl: I have some very
recent experience with that kind

of stuff in the PHP ecosystem.
Like my most recent Sass

projects are both built on
Laravel. And Laravel, has this

incredible ecosystem, like there
are like billing portals and

back end admin portals and all
that, that you just pull into

the package management system,
you still have to kind of log in

with your, you know, account or
API key, if it's a paid system,

or some of them are free. It's a
very interesting monetization

model that too, but it all gets
pulled into composer, which is

kind of the the NPM of PHP, for
anybody working with JavaScript,

right? The idea is to just have
it be hosted somewhere, you pull

it in, and then it's right
there. And maybe it's kind of

just a vendor thing, it works in
the background, but you can

expose the actual contract files
and the view files. And you

know, what the way it looks like
the what text is in there, just

how the database is connected
all of that yourself and just

keep building on top of it. And
I think once in the Ruby world,

that is the idea of having the
standard on Ruby apps, or it's

doing the exact same thing.
It's, it's a very interesting

approach, and kind of a novel
and not so novel approach, it

reminds me very much of the
beginnings of open source

software, right, it's kind of a
cycling back, let's, let's talk

a little bit about tech choices.
Because like, I think 40 to 50%

of your tweets over the last
couple days have been about

tech, like just straight up
JavaScript or rails, like which

to do to do which to take which
to choose which not to do is can

it just kind of give me a
glimpse into your mind regarding

to picking a tech stack for a
project like this? And why? And

what what kind of concerns you
have in picking this?

Josh Pigford: Yeah, so we're in
a super weird spot with maybe

where are you know, if I'm
building something, myself, but

no one else is involved, I'm
choosing rails 100% of the time,

um, and previous company
Baremetrics were Rails app. When

I started, maybe, in 2021, I had
no plans of building any part of

it. I mean, like, from a coding
perspective, at least. And, and

I think that choice at the time
was coming off of like, I hadn't

really been building much of
anything, the prior few years,

because I was in full on CEO
mode. And so I think, in part, I

didn't feel equipped to be able
to build this financial app at

the time. And so it was like,
well, I'll hire some, I'll hire

engineers, and they can talk
amongst themselves and choose

and whatever, like, it doesn't
really matter to me, because I'm

not coding any of this. Um, so
that resulted in React being the

sort of base for it, react and
next Jas, and a few other bits

and pieces. I mean, that's, you
know, was and still is, on a lot

of levels, like the the most
popular sort of tech stack. And,

and so it was like, Okay, let's
do that, because there's a huge

pool of developers, you know,
available for that, etc. So that

was the, that was like a choice
that was made in early 2021.

And, you know, we just went with
it. Now, where we're at at this

point is, we've revived this
thing, it's still that same tech

stack. But you know, as we were
talking, before we started

recording, that whole world has
changed drastically since 2021.

And it's changed drastically in
the past six months. And so now

we're at this place of like,
okay, we're already having to

rip out a ton of code. Because
of that, there's so much in

there for the compliance stuff.
And the features that aren't

part of the app anymore, we're
already having to rip out stuff,

a lot of the stuff, a lot of
stuff just doesn't work, because

like, the JavaScript world
changes so fast, and whatever

packages have updated, and
they're no longer compatible

with each other and whatever
else. And so it's kind of a

dumpster fire from like a
compatibility perspective of all

the different bits and pieces.
So now, the thing we're playing

around with, in our heads and
talking amongst ourselves about

is, what if we, we rebuilt it in
Rails? Obviously, that reduces,

and this is the discussion
that's been happening on Twitter

for the past 72 hours is you've
reduced the number of available

developers, then Bush, my
argument there is but you

increase the quality of
developer Oh, that's what I want

to be clear. I'm not trying to
burn Anyone here because I think

it's the, the reality is so many
people brand new devs, of

course, that the tech stack that
they're learning is the thing

that's most being hired for. So
like, I don't fault people for

that, it's just there happens to
be a lot of very, very green

developers in that world. Fine,
totally cool. Nothing wrong with

that. Um, but I think that also
means you end up with a lot

more. And we've found this to be
the case already in our OSS repo

for maybe is like, a lot of the
discussions are like people sort

of, you know, arguing semantics
of code versus just writing some

code. And it's very easy to
argue about the way you should

or shouldn't do things, instead
of just making decision and

building the thing. And so, I
tend to find that most people in

the Rails world, air towards,
let me let me ship something

over, let me like, try to get
this code in some sort of

standardized way, or, I don't
know, like this argue about that

stuff a lot, a lot less that
still exists. But either way,

that's sort of where we're at
is, like, we already know, the

data model behind maybe is set,
like how we organize all the

data, and then how all these
things sort of relate to one

another, I think is very solid.
And a lot of these big decisions

have already been made. So then
it becomes, okay, let's just get

the infrastructure around it
rebuilt. And I joked about

building in 24 hours. But like,
last summer, when we started,

like trying to simplify some
stuff as a proof of concept, I

rebuilt the maybe like net worth
dashboard stuff in like five

days, like, by myself. And so I
think it's very doable to you

know, I think one of the other
tweets I said was like, in 30

days, I think I could rebuild
the entire thing. And I do think

that that's true. Now, you know,
certainly people disagree with

that being a possibility, but
like, Well, I think it's

possible. And so we're just sort
of looking into that. I mean,

you know, later today, we've got
a call with a number of people

who have very deep ties in like
the JavaScript world that can

potentially, like change our
minds on some of that stuff.

But, um, we're just sort of not
I don't want to, like make a

keep doing something just
because like, that's the code

that's there. And then we end up
sticking with something we're

constantly trying to backtrack
or undo stuff or like, I don't

know, just just there's a lot of
overhead that I think comes with

the JavaScript ecosystem. Yeah,

Arvid Kahl: for sure this is
done. And there's the risk of

just sunk cost fallacy kind of
behavior, right? You don't want

that either. Just because you've
invested time into this doesn't

mean it's a good choice. And
honestly, I've been doing a lot

of JavaScript like I was, I
wasn't around to the

CoffeeScript days of 2000, like
nine and 10, and stuff. And it

was a good time, and it's stuff
was developing, and it still is,

I've never stopped developing,
right? It's not like there,

there ever is like an end point
to where this goes, it's just

developed so fast. That's just
what you said, the libraries

you're using today might have a
major version update tomorrow

that requires you to integrate
TypeScript or whatever, and then

all of a sudden, you have a
completely new thing to put into

your stack. And it just makes it
brittle, which is, I think, why

there is this massive discussion
around best practices, because

people want to avoid this
brittleness of their code,

knowing that over time, it's
just gonna decay so fast, you

don't really have this as much
in the rails or PHP or an in the

Python community, right? There
is there's a lot of standardized

stuff that is just from smartly
designed language things, that

JavaScript as a very, you know,
evolving language just doesn't

have. But I want to talk about
something that is just here to

say like, the outside feedback
from the the open source

contribution community, and I
want to I recently read a book

called working in public by by
Nadia Akbar, it's on stripe

press. It's really nice. It's I
think I have it right here. It's

pretty cool. I guess it's a book
about open source projects. And

I found a quote in there, which
I really liked was about people

who build these projects, if the
project management is kind of a

one way mirror, and she she
quoted somebody else saying,

like, you wouldn't criticize a
painter while they're still

painting that piece. But a lot
of the people in open source do

exactly that, as you're building
the code. They're going in there

looking at every leg a little
bit and saying this is not

right, this is wrong. How do you
deal with this? How do you deal

with the inevitable community
originating feature requests and

criticism kind of stuff right

Josh Pigford: Yeah, I so this
the stance that I've been taking

the replies that I sort of give
to people who are making either

filing issues on the repo or
even making pull requests. My

response is, generally look,
what's the impact of this

decision? Like what are how does
how does the entire repo and the

community of developers at large
benefit from this change? And

that right there, you know, a
lot of the sort of semantic

arguments well, you there's no
it's there's not a response. So

that says, This is good for
everyone, it ends up being more

of like, well, this is my
preference, okay, well, then I

don't care what your preference
here is, like I need, we need to

have tangible benefit to making
people change the way that

they're doing things or to make
this big overhaul that means

people have to go and like, you
know, redownload the whole repo

and run a bunch of scripts
again, to get it to update or

whatever. Like, it's, it's just,
I need an explanation, like you

need to be to make the case for
it. And it can't be well, I like

doing it this way. Or it can't
be, well, it compiles faster.

Okay, what is faster? About
three milliseconds? Like, I

don't care? Like, it doesn't
matter, you know, and that's to

me as, like, you need to explain
to me why it matters. And so I

tend to be a little dogmatic
about that on my responses,

which sort of ends a lot of that
stuff, I think,

Arvid Kahl: Do you think you
have enough or like sufficiently

calibrated tools to deal with
these kinds of things? They've

already been in like, what's in
it the whole open source

maintenance management tools
that kind of Oh,

Josh Pigford: like, does does
GitHub provide enough? No, they

don't. I think it's, you know,
there's a lot of stuff that I

would love to see sort of built
around the management of an open

source project. But it's, it's
not that bad. It's just like,

Okay, well, there's a lot of
people involved. And it's just

people management and ends up
being more like the kind of

tools that you need to manage
like a Discord server. I feel

like I need that on GitHub. But

Arvid Kahl: yeah. How's that?
What's that looking like for

maybe like, how are you
involving the community? Like on

GitHub, Discord, any other
places? Or how are these things


Josh Pigford: Mostly, it's, it's
yes, Discord, GitHub, and

Twitter is kind of where
everything happens. And, you

know, it's try trying to, you
know, writing up documents about

how to contribute, being really
responsive in discord when

people ask questions, or say
they have trouble getting some

getting something up and
running, like, okay, let's talk

through that, that gives us
feedback over how we can make it

easier to get up and running
with the platform. So I don't

know. It's mainly just being
present and responsive.

Arvid Kahl: Yep, that makes
sense. You've, you've talked

about just earlier, like funding
with us. I think that's an

important part, because
obviously, this is the bootstrap

founder podcast. And
bootstrapping is technically non

funding activity. But I believe
that you your funding approach

is kind of bootstrapper ish. I
think we had this whole

conversation, or I guess the
community had this conversation

when you sold parametrics. And
everybody was calling you like a

bootstrapper? And he said,
Actually no, brain guys, I will

look like why do we act like
one? But you know, this funding?

Is there. How's that happening
now with maybe what's what's the

plan for this?

Josh Pigford: Sure. So we back
in 2021, if you'll recall, the

the landscape was very
different. And people were just

throwing money at everything
under the sun. So it was easy to

raise money. And we end up
talking about the bootstrapper

sort of mentality. So we, we did
not raise a traditional type of

VC round we did, we went the
crowdfunding route using reg CF,

which sort of allows anyone to
invest and not have to be

accredited. So we have, we have
around 1300 investors, because

of the craft table, you know, as
little as like $20 of people are

involved in. So that was the
sort of impetus or the

origination of funding for us.
So raised 1.4 ish million back

in 2021 2022. So that was that
was the original end, like we

spent, the vast majority of that
trying to get the maybe product

out the door and hired a team of
at most are eight people, eight

full time people plus
contractors. So there's a decent

number of people involved. And
that was the most expensive sort

of route to go. But anyway, so
essentially, we're running out

of money, shut all this stuff
down, did a quick pivot, then

built a tool called detangle.
That thing makes money or at

least isn't losing money. But
then when we open sourced all

this stuff, again, there's a
whole other world of people who

are interested in investing in
open source projects, at least

commercial like commercially
viable open source projects. And

so yeah, so in the past 10 days,
we've raised another 1.1 and

some change million dollars. But
we're like refocusing like,

okay, not going to VC typical
grow at all cost route of

rehired to people from the
previous maybe team and and like

that's essentially our overhead
is that and so much larger focus

on like, building the very
sustainable, profitable

business. And leaving it at that

Arvid Kahl: sounds like a con
business to me like,

Josh Pigford: Well, that's the
goal like it's the kind of thing

I talk about my sort of view of
Maybe as the kind of thing that

you start using when you're like
18 and or 16, or whatever, like

you get your first job and
you've got some money. You need

to figure out a budget it and
all that stuff until you die and

you've gotten a state that
you're like leaving to your kids

or something like that, right?
And like all of the stuff that

happens in between and all the
different ways that you manage

your finances. And so, with that
in mind, we're like building a

company that needs to be around
for the lifetime of its users.

So yeah, so that needs to be
calm. It can't be, go, go, go go

go. We're like spending, you
know, 1000s of dollars to

acquire a single customer and
like we need VC money to prop up

our terrible customer
acquisition costs. And now it's

like, okay, we're like building
a very long play here.

Arvid Kahl: Is that also a
choice that you made for

yourself? Because like post
exit, a lot of founders kind of

switch, right? They switch from
I need to, I need to oh, I might

or now I don't have to anymore,
but I'm choosing to do things

intentionally. Was that baked
into the fabric of Maybe?

Josh Pigford: So the thing that
the Baremetrics acquisition sort

of allowed me to do is not need
to do anything, which pros and

cons to that, for sure. However,
there's, now not the need for

some or there's not the pull
towards some sort of like, exit.

Like, it's okay if this thing
takes a long time. It's fine,

you know. I haven't taken a dime
from like a salary perspective

for maybe ever leaving from when
we had all this funding a couple

years ago. So like, I can be all
in on the Maybe stuff. And we

just see what happens. Like,
it's like, we can take some like

a typical risks because I'm not
having to like, this isn't my

job in the sense of like, this
is how I'm supporting my family,

like, we're fine. So there's
sort of different outcome needs,

I guess, pros and cons, though.

Arvid Kahl: Yeah, and let's
maybe dive into the cons here as

well because everybody's going
for the exit, going for the big

cash influx. But the time that
comes after that has a couple of

challenges too. What you just
said to me, I reminded me very

much of my own choices right
now. The businesses I'm

building, they don't have to be
profitable immediately, I would

like to, but they don't have to.
I can definitely invest a lot of

you know, like, capital in it
myself, having access to it and

just see it, you know, survive
long enough to make money. It's

something that I heard somebody
called this post economic state

of mind, right? A state of mind
where you do not need to think

of your mortgage, payments, or
whatever. You think about years

or decades, you don't think
about next week or next month.

And that makes a lot of
difference. But you were talking

about challenges of this state
of mind of this time. What

challenges did you encounter
after selling?

Josh Pigford: Well, I think the
sort of challenges of not

needing to make money means that
you also aren't necessarily

optimizing for it, or at least
the speed of it. So I think it

can also be, you know,
constraints sort of breed

creativity, right? And like, if
you're trying to build something

that makes money, well, then
like, you need it to need to

make money. And so there's less
urgency with that. And again,

like, there's trade offs on all
that stuff and but I think for

me, it's the con can be like,
sort of, oh, we'll get around to

the money making part. Instead
of like, we have to get around

to the money making part. So, I
don't know, sometimes lighting a

fire under you is a good thing
and other times, I don't know,

just depends. But I think for
me, that's been the harder part

I think is I don't feel the
urgency most of the time. And

sometimes that's good. Sometimes
it's not. The inverse of that is

also true. So

Arvid Kahl: I relate to this
super strongly, like, my life

often feels like, oh, I could be
doing more. Or I could turn this

into and then some kind of
monetization idea comes along,

but then I'm then like, no, I
don't have to and I would rather

just be nice and kind to people
and help them with stuff. And

then you know, money will come
as a consequence of helping

people anyway. It's one of the
core tenants of what I believe,

which is why I'm building in
public and sharing everything

that I do anyway because I see
that you know, helping other

people help themselves best way
to do it. And you do the same

thing with what you're currently
doing in a very cool way. Yeah,

I think it's definitely a
challenge to still keep doing

stuff when you don't have to.
Have you ever considered and

this is kind of a metaphysical
question, but have you ever

considered what your enough is
in terms of not necessarily

money because money, you know,
scales infinitely, but in terms

of the contribution, like how
much time you want to spend

doing things for other people
compared to doing things for

yourself? You know, like, all
this kind of oh, after I sell,

I'm gonna sit at a beach and
drink like margaritas all day

kind of thinking. That's like,
obviously, the one extreme. The

other extreme is, I'm working
full time, like, all the time

doing new things. And I think
most people like you and me,

we're somewhere in between,
like, where is that line? Like,

have you ever consciously
reflected on that?

Josh Pigford: So for me, it ends
up being my core is this sort of

need to create something now,
whether that's software, whether

that's like music or like
woodworking or anything. That's

the pole. So at the end of the
day, I'm sort of optimizing for

that. That's sort of where I get
a lot of fulfillment from. But

that has a lot of different
flavors. And, you know, it's

like, currently, I'm doing a lot
with software. I mean, I've been

doing that for the better part
of 20 plus years. And so it's an

easy way for me to get, like
some sort of fulfillment, from a

creativity perspective. But I
think that changes over time.

And that's like, a lot of that's
based on life stuff, right? So

it's like my kids are older. I
have one adult kid, couple of

kids in high school, like the
sort of time and sort of

investment in that side of life
is like, different now than it

was 10 years ago when they were
little. And like, I think life

sort of, like always evolving
regardless. And so for me, the

constant is just like, every
day, I want to create something

and then that enables certain
things, right? Something like a

big exit, gives me more freedom
to do things with kids and for

us to have different experiences
and that kind of thing. So I

don't know, it's a weird melting
pot of things. But the way my

brain works is like, I have to
make stuff in some form or


Arvid Kahl: Yeah, that's so
incredibly noticeable, like with

you in particular, like, I don't
remember a time where you didn't

do something really interesting.
And we think about detangle as a

thing of just recently, but also
Laser Tweets and all these other

things like over the past, like
Laser Tweets, you sold that too,

right? Like these things go come
into your life and they leave

your life again, like you have a
very high churn and the best

kind of sense, in terms of
projects that you're working on.

Do you want to keep doing this
forever? Like, that's also part

of this enough question for me.
Is this just the state of being

that you always want to do?

Josh Pigford: Maybe, I mean, so
I have this list of like, every

project that I've ever done on
my website and it's I think I

was the other day was updating,
it's like 70 projects or

something like that. And that's
everything from just dumb. So I

start tracking that stuff in
2003. So that's 20 years of

making stuff. So like, I don't
know that it's just a sort of,

it's not necessarily a fad for
me, like I don't know that I'll

stop. Because that's been at
least half of my life, at least

from a business perspective, I
guess. Certainly, as a kid, I

was making all sorts stuff too.
So I don't I see it changing.

But I feel like the hobby side
of it may change a bit to the I

said something other day where
it was like, I want to use

projects or I want to build
stuff that like hundreds of

millions of people use but also
want to go like live in a cabin

by myself and never talk to
another human again. And I

genuinely feel that where, you
know, is there a scenario one

day where, you know, my wife and
I are often in the mountain

somewhere and like, away from
civilization, maybe. I

personally would love that. My
wife's not quite as like, anti

human as I can be. But I, you
know, I think it morphs over

time, but as my interests change
and I think to me, that sort of

the constant is that it has to
be something sort of new for me.

I'll just get bored. And so
there has to be some sort of

fresh way to approach it.
Otherwise, I'll lose interest.

Arvid Kahl: Which makes this
whole open source thing such a

smart idea, I feel. Right?

Josh Pigford: And I think that's
one of the motivations behind it

was like, well, why not? No one
else has really done this. So

let's give it a try. That was
the case with Baremetrics, where

like, we made our dashboard
public for everybody to see. It

was early on before it was
really making much money was and

I talked to other founders, the
advice was like, no, don't like

put that out in public. Like,
you're shooting yourself in the

foot with like competition and
stuff. And I was like, well, I

don't know why not. Like, I like
the experiment of it. And I sort

of feel that way with this open
source stuff is I like the

experiment of what happens when
you make a million dollars worth

of FinTech software, open source
for anybody to use and then try

to build a business around it,
you know.

Arvid Kahl: Yeah, that's very
cool. I love that both of these

kinds of experiments are kind of
transparency forward

experiments. Instead of just
making things like even more

secretive and more secluded, you
just opening up, right? And I

love that with Baremetrics. You
kickstart I think in many ways,

the whole open dashboard thing
that so many people still do to

this day, right? There is a time
in every business is life where

it's beneficial to have it open.
And then there is a time when it

becomes problematic when there's
too much attention. But still

for that time, like building in
public as well as a seasonal

activity, that is a wonderful
thing that gets a lot of

goodwill, a lot of trust
established in the community of

people. And that is always good.
And I really like that that's

the outcome of this. So with
Maybe being an open source

project that you will monetize
through, like additional

services, what's the vision for
this going forward? Like what

will make you stick with
something like this for decades

to come when you're a person
that always needs novelty?

Josh Pigford: Yeah, I think that
it's understanding that software

hasn't ever finished. I mean,
depends on what problem you're

solving. But I think having a
very lofty sort of goal, that

where we want customers that
will use the software for 60

years, like, if that's the goal,
there's a lot of work to do to

sort of meet the needs of in the
same way that you know, your own

personal finances are always
changing, growing whatever or

not growing, which is its own
problem to solve. And like, if

we can build products that help
people for a lifetime, there's a

lot of interesting things to try
to make that happen versus, you

know, some other more hyper
specific tool set or something

like that. So I don't know,
given the breadth of work to do

that sort of a never ending sort
of thing to solve.

Arvid Kahl: Yeah, it's a field
that will present you with not

only throughout the seasons of
anybody's life that are also

changing, but even the economies
of the future are going to

introduce new things, right?
Like the whole bitcoins and

whatnot, like all the crypto
stuff, that will be an

interesting challenge to
integrate. And that will change

that will be flexible. Man, I'm
so close to making a joke about

lifetime payments and lifetime
prices here. And I don't really

know what the joke would be. But
have you thought about

monetizing with that kind of
stuff? Because obviously, when

you think about 60 years, like
would you ever think about

selling access to a product for

Josh Pigford: I could see if
Maybe was able to be a sort of

downloadable product that didn't
need external data, yes. So the

problem here with finances
depends on, a lot of times it

just needs external stuff. Even
if you're manually inputting

data, there's still a lot of
stuff around the value of

certain things. So like stock
market data, for instance, like

if you've got investments will
like we need the investment data

to tell you what the current
value is of your investments.

And that is the reason, a lot of
the reason at least to have a

subscription fee is like each
account has costs for us, right?

And so, you know, as nice as it
would be to sort of almost go

this somewhat altruistic route
of like, let you have a one time

fee for it. The reality is that
that's not super possible at the

moment. Maybe it will be in the
future. I don't know.

Arvid Kahl: That's aptly named
product, I guess, for that kind

of, you know, unspecific future.
But I think that's kind of where

I'm getting with the whole one
stuff where the base camp people

like the idea of like selling a
product once having people self

hosted and running forever makes
perfect sense if it's its own

internal, kind of isolated
database and you just have, you

know, people chatting with each
other and you keep it all on

your server. But the moment
there are API integrations that

you only can provide, like if
people can run it on their own

service, that's also fine. But
if there's stuff that you need,

obviously subscription model
makes sense. Yeah. And in many

ways, your definition of
lifetime is a very refreshing

one. Because like most people
would define lifetime as

lifetime of the product, right?
Lifetime of however long they

want to run their servers. But
for you, it really is the

lifetime of the customer. So I'm
very much looking forward to

seeing you just go on this
journey and build something

really, really cool in front of
everybody with the help of

people who are interested in it.
If people want to follow you on

this journey, both you
personally, the product, the

company, where do you want them
to go? Where do you want them to

see the journey, whether you
want them to contribute? Put it

all out here.

Josh Pigford: Yeah, the easiest
place is Twitter. So just

@Shpigford, that's where I talk
too much. So you can go to

maybe.co, there's some links to
that stuff that'll change a lot

over the coming weeks. But that
sort of ends up being the

launching pad to not be behind
on stuff. Anywhere else, I'll

send you and it'll change in the
next week.

Yeah, that's right. Maybe
tomorrow, who knows? Change is

the only constant, right?

That's for sure.

Arvid Kahl: Thank you so much
for sharing all of this. I'm

super excited for you in this
project that gets really really

cool not just to see that you're
building something amazing that

I might find very useful for
myself, just to see the just the

excitement and enthusiasm of
people in the community that

over the last like, what 20 days
or something has just exploded.

That is so so cool. So I'm
really, really happy that you're

sharing this, that you're doing
it. And thank you so much for

chatting about it on the show
today. Thank you so much, Josh.

Josh Pigford: For sure. It's
been a ton of fun chatting.

Thanks for having me.

Arvid Kahl: And that's it for
today. I will now briefly thank

my sponsor acquire.com. Imagine
this, you're a founder who's

built a really solid SaaS
product, you acquired all those

customers, and everything is
generating really consistent

monthly recurring revenue.
That's the dream of every SaaS

founder, right? The problem is,
you're not growing for whatever

reason, maybe it's lack of skill
or lack of focus or play in lack

of interest, you don't know. You
just feel stuck in your business

with your business. What should
you do? Well, the story that I

would like to hear is that you
buckled down, you reignited the

fire and you started working on
the business, not just in the

business and all those things
you did, like audience building

and marketing and sales and
outreach. They really helped you

to go down this road, six months
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successful business. That is the
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unfortunately, is not as simple
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you might find yourself in is
looking different for every

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common, but it looks different
every time. But what doesn't

look different every time is a
story that here just ends up

being one of inaction and
stagnation. Because the business

becomes less and less valuable
over time and then eventually

completely worthless if you
don't do anything. So if you

find yourself here, already at
this point or you think your

story is likely headed down a
similar road, I would consider a

third option. And that is
selling your business on

acquire.com. Because you
capitalizing on the value of

your time today is a pretty
smart move. It's certainly

better than not doing anything.
And acquire.com is free to list.

They've helped hundreds of
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it out at try.acquire.com/arvid,
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this is the right option for
you, your business at this time.

You might just want to wait a
bit and see if it works out half

a year from now or a year from
now. Just check it out. It's

always good to be in the know.

Thank you for listening to the
Bootstrapped Founder today. I

really appreciate that. You can
find me on Twitter @arvidkahl.

And you'll find my books and my
Twitter course there too. If you

want to support me and the show,
please subscribe to my YouTube

channel and get the podcast in
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see and leave a rating and a
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It really makes a big difference

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other people's feeds. And
that's, I think where we all

would like it to be just helping
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understand new things. Any of
this will help the show. I

really appreciate it. Thank you
so much for listening. Have a

wonderful day and bye bye.

Creators and Guests

Arvid Kahl
Arvid Kahl
Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.
Josh Pigford
Josh Pigford
✨ dabbler 💰 @maybe 💱 @synth_finance ⚖️ @detangleai
292: Josh Pigford — The Open-Source Transformation of Maybe
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