Anniversary Throwback - #17: Taylor Brooks, Simple Donation

As we near one year since starting In The Thick of It, we're working on a celebratory episode. In the meantime, we'd love for you to catch up on some founder stories you may have missed.

In this episode of In the Thick of It, host Scott interviews Taylor Brooks, founder and CEO of Simple Donation. Taylor shares his journey from growing up in Atlanta to attending Auburn University and working various jobs before starting Simple Donation, a software company that builds online donation platforms for nonprofits and churches. He discusses the challenges of balancing a full-time corporate job while also running his startup on the side for many years. Taylor provides insights into building company culture, hiring the right people, learning from mistakes, and focusing on solving customer problems rather than just selling features. He emphasizes creating long-term value and building relationships. Throughout the interview, Taylor stresses the importance of persistence and consistency in business. He aims to continue leading Simple Donation for 30-40 more years with a stewardship mindset.

***

About Taylor:
Taylor Brooks is the Founder and CEO of Simple - a company that provides financial tools for churches such as online giving, event registration payments, donor analytics, and corporate card programs.

He was born and raised in Atlanta, GA, graduated from Auburn University, and moved to Texas in 2010. #texasforever

Taylor has been married to Rachel for 14 years and has three children: Wyatt, Lyle, and June. For fun he likes to hunt, fly-fish, read old books, listen to old music, and play tennis.

About Simple:
An easy-to-use giving platform for churches that use Rock RMS, with personal consultation tailored to your congregation's needs. All in service of helping you grow the generosity of your people. We're here to support your mission so you can focus on your ministry. With expert guidance, analytics, and custom giving software designed for your Rock RMS church, we're your partner for community impact and giving that's cheerful, meaningful, and … simple.

To learn more, visit simpledonation.com.

***

If you or a founder you know would like to be a guest on In The Thick of It, email us at [e-mail]

Creators & Guests

Host

Scott Hollrah

Founder & CEO of Venn Technology

Guest

Taylor Brooks

Founder & CEO, Simple

What is In The Thick of It?

Join Scott Hollrah, founder of Venn Technology, as he takes you "In the Thick of It" with the real stories of founders who are actively navigating the challenges and triumphs of running their businesses. This podcast goes beyond the typical entrepreneurial success stories and delves into the messy, gritty, and sometimes chaotic world of building and growing a company. Get inspired, learn from the experiences of others, and gain insights into what it truly means to be in the thick of the entrepreneurial journey.

Hey, listeners, this is Scott Hollrah.

It's hard to believe that we launched
In The Thick of It almost a year ago.

As we're nearing our first anniversary,

we're working
hard on a celebratory episode.

In the meantime, we'd love for you
to catch up on a founder story

you may have missed.

In today's episode,

I got to chat with Taylor Brooks, founder
and CEO of Simple Donation.

From growing up in Atlanta
to attending Auburn University.

He shares what inspired him
to create an online donation platform

for nonprofits and churches, all while
balancing a full time corporate job.

What you learn about Taylor
is that he's all about creating long term

value, building relationships, and taking
a stewardship mentality in business.

In fact, his goal is to continue leading

simple donation
for the next 30 to 40 years.

He has a great perspective
on persistence, consistency

and creating win win
solutions for customers.

I think any new or aspiring
founder will resonate with his approach

to entrepreneurship.

Well,

Taylor, thank you so much
for making the trip up from Austin.

It's great to have people actually
in the studio.

We can do remote sessions
and they work great,

but there's always something nice
about seeing people in person.

So thank you so much for
for making the trip and making the effort.

Yeah, it's a pleasure to be here.
Thanks for having me.

We always like to start with
what was growing up like.

So where did you grow up?

What was your family like?

What was the family dynamic like?

grew up in Atlanta, Georgia.

So I'm a true son of the South.

I grew up in a great home.

I have a brother
who I actually just spent time with.

This past weekend
we got the kids together. Was really fun.

Yeah.

Dad owned his own business.

Grandfather owned his own business?

Yeah, just running around
and played sports a lot.

When I was growing up,
I had a really great, great home life.

But. Yeah.

What sports were you into.

Or in track? In high school
or in cross-country?

In high school?

I played golf, tennis.

I didn't play football or baseball,

but I tried to run the gamut
on everything else.

And are you still a runner today?

I've gotten back into it.

Okay, so you got your woop
and we were talking earlier.

You got some other new fitness
tracking stuff on the way, so.

I do I've started tracking sleep tracking,
and I just hired a coach

this year, a fitness coach.

And so I have a goal this year
of running a sub seven minute mile.

Good for you, man.

501 was my fastest in high school.

Dang.

And I don't think at 41
that I can break five.

So I'm going to set my bar at seven.

And then eventually six.

I want to run a run another five minute
mile at some point in my life.

Good for you, man.

That is awesome.

Going back to growing up,
what were you like as a student?

Were you a straight-A student? Were you.

Awful student?

Terrible. Hated school.

Okay. I didn't. Hate it. Per se.

I felt in this was more so in college,
but in high school,

I felt like there was such a disconnect.

I just didn't see the through line of,
like, how does this connect to real life?

I did spend a lot of time

just kind of shadowing my dad
and shadowing my grandfather,

and I just didn't see the connection
between what they were doing

and how they treated and interacted with
their customers and grew their business.

And what I was learning in school.

Which is funny now,
because now I feel like I'm backfilling

a lot of the things that I perhaps
didn't appreciate.

I'm reading a lot of history now.

I'm interested in the Roman Empire
and like it would have been pulling teeth

when I was a little kid or in high school
in college, to appreciate those subjects.

So growing up, I did okay.

In school, I was more focused on sports.

But yeah, not student wasn't my game.

You mentioned the Roman Empire,
and lately, like, there's been

this whole social media blow up about men
thinking about the Roman Empire.

Were you reading about the Roman Empire
before this?

Prior? Okay. Right.

So you really have been thinking
about the Roman Empire? Yes.

Okay, well.

I also have a business partner
now who is a, like, history buff.

Actually, this is funny.

When I knew
that he was going to be my partner.

We were at a conference in Las Vegas,
and we were walking around the strip

and he, for 2.5 hours, just unloaded on
This Is How Rome Fell.

And I was fascinated.

I was like,
how in the world, you know, so much.

And so that being in proximity to him,
spending a lot of time with him,

I've gleaned a lot of history
and it's infectious.

His interest in it has been infectious.

Very cool.

All right.

You mentioned your.

Dad. Had his own business.

And did your grandfather also
or were they working together?

Yeah.

Pops, as he was known,
had a plumbing supply company that he ran.

It had.

I mean, imagine what home

and even commercial construction
was like prior to Home Depot or Lowe's.

It was all mom and pop shops.

So he owned this
plumbing supply company in Atlanta.

I think they had ten locations
at the height.

He ended up selling it.

He was always retired
as long as I'd known him.

And then he went back into starting a CPA
firm,

and dad went and worked under him

for Brooks and Brooks Associates,
which is the CPA firm.

My uncle still runs that CPA firm.

I'm the black sheep of the family.

My brother is a CFO of a construction
company, commercial construction company.

I'm the only non CPA in the family
and coincidentally, I run a business.

I think you've done okay.
I think you've made the family proud.

So that was kind of their deal.

Was that the accounting practice was what?

How was the intersection
of all the family?

And then dad ended up doing
commercial real estate development.

Uncle ended up starting other companies.

So there's an entrepreneurial bug
in the Brooks genes.

Yeah.

I'm thinking about your grandfather
going from plumbing supply to being a CPA.

Those seem worlds apart.

Did he have an accounting background
or did he just decide one day

I'm going to go sit for my CPA
and start a accounting firm?

He had a JD, CPA prior to this

plumbing supply,
but he didn't have the firm.

So while he was running this company at,

you know, Post-acquisition
what do I do next?

And so he started the accounting practice.

I think he did it more so to get reps
with other business owners than to, like,

try to build a business.

I think he wanted to be in the arena
in the game versus

I mean, he didn't need to work.

You mentioned
you're the black sheep of the family.

My brother is a fighter pilot.

So like, how do I compete with that?

I've started a somewhat
successful business

and he's the fighter pilot,
so I don't know.

I feel you there.

All right.

Growing up in Atlanta,
did you guys move around or were you there

K through 12 all the way through? Yep.

And you went off to Auburn.

Did or you go.

Where you go. I'm
so glad to hear you say that.

You know,
I went to Texas A&M and we won't talk

about the most recent matchup
the Aggies won.

I'm so sick of Alabama winning things.

I'm just so sick of it.

And actually it's been kind of nice
the last couple of years.

But yeah in the roll tide War Eagle
I'm a I'm a war eagle.

So I don't know how you feel about this,
how conflicted you are.

And this is perhaps going off
topic of this podcast.

But when Texas plays Alabama.

Do you pull.

For Texas and hold your nose
or what do you do?

Man, I was really conflicted that game.

And knowing
that we're going to play Alabama,

I tend to root for the the SEC.

Now next year that's going to change.

But I would rather play an unbeaten
Alabama team because it helps us.

If by some miracle
we actually beat Alabama.

I think you get a shot
this year. I actually do. I'm with you.

I'm right there with you. Auburn.

What did you study in school?

I wanted to be a pilot.

Really? Yeah.

Commercial pilot. Navy pilot. Air force.

I didn't want to join the military,
but I did want to be a pilot.

That is another theme in the Brooks
family is aviation.

My dad was a Vietnam War veteran and flew.

He was in Vietnam and I was always
interested in planes, I still am.

If you look at my YouTube history,
you'll see.

Poker and you'll see ATC.

In plane landings.

I just love aviation.

So I went to Auburn.

I coincidentally, the professional flight
program is in the School of Business.

I don't know why it's not in the School of
Engineering, but I wanted to be a pilot.

And 911 happened my freshman year.

And something that I thought was more
it was clear to me

then that this is a hobby
I'm trying to turn into a career.

And there was less optionality

in pursuing a professional flight degree.

And so I transitioned to general business,
but continued to fly out of Atlanta

was actually really hard to get ours
out of the Austin or Auburn airport.

So I flew out of Atlanta
and got my license there,

and then very quickly realized
this isn't a career for me.

I still enjoy being around planes
and look at planes

and but yeah,
that was a not a career choice for me.

So I ended up going general business.

And at the time Auburn had
there was germinating

a entrepreneurship degree,
and I was really attracted to that.

It was literally the first year
that they had started it.

So it wasn't fully formed.

They didn't have a lot of specific classes
around entrepreneurship.

It was more of a buffet,
you know, go get some air,

go get some management,
some in my ass accounting, etc.

there was two classes that was taught by
a professor that I really, really liked.

Michael Kincaid, awesome guy.

New venture creation was one class
and entrepreneurial marketing

was the other one.

And then I took another marketing class,
Consumer Behavior,

that was in the psychology department.

But that professor just spending time
with him after class and drinking beer and

even though he had a one foot in academia,

he also had started several businesses.

And going back to what I said earlier,
he really melded those two together.

What is real life experience
look like with what you're learning here

in the College of Business?

And so that was really formative
for me to go, Like,

I would, I think as a junior at that time
when I started studying under him,

but really, really enjoyed that.

The professor makes all the difference.

Like it could be one of the most
boring subjects in the world.

But if you got a good professor
that really cares about it and has that,

you know, just dynamic nature, to him,

it didn't really matter
what the subject matter is.

I 100% agree and I do it the same today.

I feel like I don't read books.

I read authors when I find an author
that I really respect

and I really resonate with,
I try to find their whole catalog.

Everything that they've done podcasts,
videos, articles, op eds,

I just want to read that person's mind.

And Kincaid was just a great teacher.

And these were entrepreneurship
specific classes.

Like what was the coursework like?

A lot of case studies.

So following after Harvard,
you know, you take a case and then you,

you know, argue a position
and then you argue the opposite position

and then they don't tell you what the
I don't know what it could be.

It was so long ago, but it could be hey,

we're facing the strategic,
you know, initiative.

How would you basically deploy
resources and capital

and go after this initiative
and what's the right way to do that?

And the story was already written,

but you would kind of work
through that case and different teams.

The class would be separated into teams,

and then you get to find out like
how it actually played out in real life.

And we would just do those over
and over and over.

So it was a lot of reps of working
through cases and different situations.

You didn't get the full story,
you got the starting elements

and you had to go
put it together on your own

and see how your outcome matched up
with the actual case.

That's right.

Yeah, that is really cool.

I wish I had taken a class like that
in college.

I think it'd be fun to do today.

Yeah.

Outside of your classwork,
what was your college experience like?

Obviously a lot of SEC football.

What else?

Were you in a fraternity
or involved in things on campus?

I was really involved in a campus ministry
on campus.

You know, I grew up going to church.

The Brooks Boys had this tradition
where every Saturday morning

we go to waffle House,
and I can just remember my grandfather.

I could hear him

walking up the stairs to come
wake me up and singing amazing Grace.

So that's kind of the ethos and world
in which I grew up in.

Was hanging out with my grandfather,

my dad, my brother, and going to waffle
House and drinking diner coffee

and, scattered,
smothered in covered hash browns.

But I feel like it's common to hear people
go off to college.

So they're wild oats and, you know,
perhaps walk away from the faith.

I had the opposite experience at Auburn.

There's a really great campus ministry.

I'm still in contact
with the director there,

and my faith really grew at Auburn.

It was a really, really formative time
for me and, extremely thankful for that.

And it was through
no work of my own, for sure.

Did you get back to campus at all?
Do you go for games?

I haven't been back in forever.

I've been to Kyle Field
more than I've been to Auburn.

All right.

What was your first job?

Did you work at all in college?

Did you work in the family business.

And did not work in the family business
in high school?

I grew up having, you know, working
retail stuff, a cleaners.

I worked for a commercial plumber,
of all things, but not connected

with the family business.

I did a lot of hard work
and I did work through

college, building doors, doing carpentry
and stuff like that.

So are you handy today? No.

I mean, I can watch a YouTube video.

And figure it out. I can figure it out.

I've talked once before about this,
but I'm not super handy.

There are some things that I am
capable of doing.

Need me to hang a ceiling fan
or a light fixture?

We're good.

The minute
it becomes plumbing like I'm out.

Yeah, dad would say gas goes boom,
so be careful with that.

Good advice.

I actually had a gas leak in our attic
not too long ago, and we had the call

the fire department to get it shut off
and then bring in the plumber

to get it all fixed.

And I definitely would not have touched
that on my own post-college.

Where did you go from Auburn?

Yeah, let me run it to today really quick.

I'll just give you a quick 60s
graduate from Auburn, stay in Atlanta,

work for chick fil A, chick fil A,
go to family business, family business.

Moved to Nashville, work
in the entertainment industry there.

Go from Nashville to starting my own gig

and doing a little technology projects.

In 2010, moved from Nashville to Austin

to work for a political consulting firm,

then go to work for a consumer
email startup,

then go to work for a SAS company,
then start simple,

then go to work for a fortune 15 company,
and then go full time with simple.

That's the quick rundown
from post-college to 2023.

That's a pretty diverse background,
and we'll kind of jump around in there,

but simple.

As a software company, it is.

Are you a developer? Yes. All right.

I didn't hear a whole lot of like,
software development in college.

When you went to chick fil
A, were you in the I.T.

Like where were you building
apps for chick fil A?

I was in it, but I was more in hardware.

my responsibility there was to basically
go around to the different stores,

install new point of sale systems
to train the staff

more so the management on back office
software.

How this talks to the corporate office
and then go to the next door.

And by the time that you finished
the full fleet of stores,

it's time to turn a new point
of sale system and you're on the road.

So first job out of college,

living on an expense account,
being on the road, not having a

girlfriend, not being unencumbered by,
you know, a family or anything.

I say encumbered. That sounds bad.
I know what you mean.

It was awesome.

I got to see a lot of the country
through that experience and learned a lot

is a great so more
so on the the hardware side of it.

There was a team that went into ran
all the networking wires

and stuff,
but if I was bored, I'd go in at night and

run wires
and yeah, for cable, cat5 and all that.

Chick fil A is a company
that I admire for many, many reasons.

Last week
I went through the drive through one night

and the young man that took my order was

1718 and he looked me in the eye.

He called me sir,

which I don't need to be called, sir,
but like the polish and the precision

and the my pleasure, like chick fil
A just does so many things, right.

And two things.

If I see on a resume,
I'll give an interview no matter what.

If they worked at chick fil A,
or if they were an Eagle Scout

and may not get the job.

But I want to talk to that person,
because if you've been through the proving

ground of chick fil A man,
you got some good stuff going on.

So was
was it a great place to work for you?

And obviously your role was unique
and different

than what
most people think about with chick fil A.

You know,
I did worked in a store in college.

I worked in a mall store in college,
so that wasn't my first exposure

to the business.

In fact,
that actually goes back to high school.

You know, being in Atlanta,

one of my teammates and track
is the current CEO of chick fil A.

No way. Yeah.

So the Cathy family
all went to my high school,

and the other side of the Cathy family
went to Auburn.

And so I am thankful to have an inside
peek at how that all works.

And that yeah, it's a great family.

It's a great business.

They do an amazing job of cultivating
that culture and protecting it.

I agree with you.

I've got a ten year old
and I'm already thinking your first job

is going to be a chick fil A
because it's so formative.

They do instill hard work
and respect, mutual respect for customers.

And like you,
I have a high admiration for that.

That company.

All right.

Nashville
next on Twitter from my uncle's family.

You know, because he was a CPA,
he would see a lot of these.

What, you know, Buffett, Munger
would call cigar butt businesses,

perhaps on their way out.

And there was one more puff on the cigar.

And so he would buy these businesses

that his customers wanted to get out of,
and he would get them at a fair price.

And then turn them
or liquidate them or whatever.

So I went to work
for one of those businesses,

and I worked there for maybe

8 to 10 months as kind of a gym

and, was working in managing this factory
that built of all things,

window and door products,
which I was connected to.

And in Auburn.

It was a great experience.

And then from there went to Nashville,
to work in the entertainment industry.

As an entertainer. Are you. Musical?

No, I worked as a an agent for keynote
speakers.

So folks that would do college
commencement speeches or corporate,

you know, rah rah sales meetings
or annual meetings.

I worked in that industry.

Who were the speakers
that were in your portfolio.

At the time?

It was all of the Fox News talking heads.

So, Glenn Beck,
Hannity, Colter, Holly North Cavuto.

I spent three months on the road
with Glenn Beck during his,

Inconvenient Book tour.

He had just transitioned from,
I think it was CNBC to Fox News.

This is prior to him moving to Texas.

You're still pretty young at this point.

You're mid 20s.

Yeah. What was that.

Like getting to be around celebrities?

I'm not one to be starstruck.

I mean just normal people.

But yeah, it was interesting just
to see the when someone walks off stage,

what are they like on the bus.

What do they like when they're
how do they treat other people?

Just all great.
I don't have anything negative to say.

Sure.

I imagine that with as many people
as you were working with,

you probably got to see some that were
very, very kind and some that were not.

Don't name names.

But is that a fair statement?

Yeah.

I mean, you have people
that are very impressed with themselves

and they want other people to know it.

That was actually more of a rare case,
believe it or not.

I think, you know, a lot of talent
or comedians or speakers,

they treat it like a business.

And so there is a need
to have some representative

that can advocate
on behalf of their schedule.

I mean, they have families.

They, you know, going
traveling across the country

requires
them to be away from their family.

And so if they want
they don't want a private jet

because they're prima donna
and they want to fly on a Gulfstream

everywhere, they want to be back
at their kids little League game.

And that's the tool that does it.

So when you communicate
that to a customer, they're like, well,

I don't want to pay for a $30,000
round trip Learjet flight.

It's like,
well, you're not going to get them.

For another speaker.

Yeah, that's okay.

Like here's four other options
that are in your range.

So it was an interesting business
to be in.

I call it smile and dial.

That was my role
there was to drum up business.

And I had a sheet card of 30
calls and emails,

30 calls, 30 emails,
60 contact points per day.

And did that Monday through Friday.

Wow. So you cut your teeth in sales like.

And that's hard selling to
that's not inbound you know warm.

Let's work it. You're cold calling.

That's correct.

How has that helped
you in what you're doing today?

I like to say I have a mentor
that was in the

in the entertainment industry as well.

And he said eight no's for breakfast

and I love that.

I would call people in.

My approach was I would call someone,
I call some,

you know, marketing director,
event director in a company and say

you're not interested in a speaker
this year, are you?

And they go, no, I get great.

Number two, you're not interested
in speaker this year.

And, you know, I couldn't make it
a full day without finding 30 no's.

So it's not personal.

It's just my approach to sales

and company building is it's meat
and potatoes.

I'm just going to be persistent and
consistent over a long, long, long time.

And we're going to grow that way.

I'm not the sharpest tool in the shed,
but I, I can go a long time.

I'm pretty persistent and pigheaded.

I was at an event this past weekend
and they brought in a band to play band.

It's called Telephone Friends,
which I highly recommend.

you check out,
and there's a line in one of the songs.

I'm not going to get it exactly right,
but it's something to the effect of every.

No, it's one step
closer to a yes and every yes.

There's the end of a whole bunch of no's
or something to that effect.

And it was,
like I said, worded far better.

And I'm like, wow, like spot
on, smiling and dialing, traveling around.

Did you get to go on the Gulf Stream?

Not a Gulf Stream, but I've been on.

Yeah, I traveled on several planes
with some of the talent.

Yeah.

I remember being in a King Air,
with Huckabee on the way to an event

and it being really, really bumpy.

And even though I like aviation,
you never get used to turbulence.

And it was really turbulent.

I remember him being cool as a cucumber
and going, you know, these planes,

they use these planes and hurricanes
to like, measure the wind.

And I was like,
that is not helpful right now.

Governor.

My first job
out of college, I worked for an aviation

services company,
and we had three company aircraft.

And I can remember
getting so spoiled at 2223,

parking my car in the hangar,
getting on the company plane

and being wheels up,
you know, three minutes later, no 23 year

old should get to do that.

We actually had a King Air think I was
a King Air 250 or something like that.

And it's really cool.

And to your point,
it does seem bougie, but I totally get

the mindset of no,
this is how I get home faster.

I don't have to go through security,
don't have to get there two hours early.

I can just show up and go. Yeah. Goals.

Yes, yes.

I don't have a lot of.

Aspirations for material things like I'm

I'm very, very happy with what I've got.

And you know, as I've gotten older,
relationships have meant a lot more.

But if there is one thing
that I could snap my fingers and get,

it would be a check and Netjets card,
but that'll never happen.

It's such a for me.

I don't travel enough to justify the cost,
and I'm a homebody anyway,

but that would be the indulgent
spend that I would have.

When you need it, it buys you time.

Oh man, when
you have three kids under three

and you're trying to go on a trip and haul
all these kids through the airport,

you're like, I will

charter a jet before I do that again,
but I don't.

My kids are older now and they,
you know, they're self-sufficient.

Getting through the airport.

Yeah, I can totally relate.

I remember those days.

My oldest,
we put him on a plane when he was probably

just a few months old,
and on the flight out

we had people coming up to us and saying,
when I saw you sit down, I was so nervous

to be sitting next to a baby
because I just, you know,

you're on the plane, the baby cries and
oh my gosh, your son, he was just perfect.

The trip home was the exact opposite.

Screamed the whole way.

I'm like cowering in my seat, like, okay,
is there a parachute?

Can I just jump out of this plane?

And anyway, we're we're
well beyond that today, thankfully.

But I get what you're saying. Yeah.

All right. Skipping ahead of the jobs.

That you had leading up
to starting. Simple.

Where did you learn the most?

You mean as far as technology.

Technology business?

You know, I had a project post, speaker
rep courier.

I was like, what do I want to do now?

And I was talking to a buddy that worked
for a nonprofit down in Atlanta,

and he was not complaining,
but he was talking

through all these challenges
that he was going through.

And I was thinking,
these are solvable problems.

This doesn't seem insurmountable.

Dabbled in,
you know, WordPress development.

And and I ran
my own little blog at the time.

This was 2007.

So I think I was a little early
on, you know, dabbling in technology.

You graduated from college in
oh five. Yeah.

And the next time I was like, maybe
my roommate at the time was a programmer.

He was on the development team
at the speaking agency, and he had written

all custom software,
totally homegrown CRM, and it was awesome.

And it had a built in telephony thing.

So he was
we had soft phones, IP based phones,

that connected to the homegrown CRM.

It was amazing.
Like unbelievable developer.

And he was my roommate.

And I came home from talking to this buddy
of mine that worked for this nonprofit,

and I said, hey, my friend was talking
about all these things.

Do you think that maybe we could cobble
something together?

He's like, yeah, I think so.

And so I write a little proposal,
and the next time

I hang out with Jonathan, I'm like, hey,
how are those challenges?

He's like, oh man, it's
we're still have all these issues.

And I slide this little one pager
and I had t shirt sizes on it,

and I was like, well,
this price range solves these problems.

And it was whatever 17 five.

And like this price range
25 K solves these problems.

And then like this bottom 132
five this solves all of your problems.

They go away.

And he was like interesting.
You can do all this.

I'm like, yeah, yeah, we can do it.

Narrator. He could not do it.

A lot of businesses have been born
like that, though.

Yeah, I.

Knew I could figure it out.

And, I mean, I'll be damned.

He goes and.

Takes that little sheet to his boss.

I get a signed contract for 25 grand
and a check.

For 12 five.

And we're off to the races, and I'm like,
oh, boy, now we got to build this thing.

So I'm like, John, my roommate.

And I'm like, John,
we're about to build some software.

I need you to, well, really, you're about
to build some software, and I'm about.

To crack the whip and get you to build it.

So that experience was my first ever
custom software development project.

And it was dead on.

Arrival didn't pan out. It delivered.

And it solve the problems
that we set out to solve.

The thing that I didn't learn was
that software is never done.

It is never done.

It takes continual
gardening and investment

and pruning and it's dynamic.

You know, the systems and services
that you're interacting with, they change.

And so therefore you need to change.

I did not anticipate
that when we deliver it,

the requirements
generally stayed the same.

But the underlying systems
that we were interacting with had changed.

And so I was like, hey, this is new scope.

And customer didn't like that.

So I started to see if we're not going

to get new budget for this, then
this is going to eat through our margins.

And like this, math just won't work.

We can't pencil this out.

So I think I learned a lot through it.

I mean, a ton through it.

I also learned, man.

I'm paying this developer a ton of money.

I should be on that side
of the transaction.

And so that was and I really enjoyed

talking through the designs
and the schemes and all that stuff.

And it was enough of a puzzle for me.

I just had a toe in the water
at that point

where I knew that
I felt like I would enjoy

being on the developer side of things.

So that was my first entrance
into a technology

like full scope technology product.

I'm like, I could spend my whole career
doing stuff like this.

One of the things you mentioned
was you enjoyed the

design and architecture of the system.

You didn't have a ton of that
in your background up to that point. Was.

I don't think so.

But yet you knew enough of,
you know, technology,

you understood relational databases,
and you were able to piece that together.

Yeah, actually, I'm glad you brought
that up when I was at this agency,

you know, booking keynote speakers
because my roommate was the developer,

the CRM that he had built
had a lot of prospect data in it,

and I kept wanting more and more access,
like granular access to that data.

So it would help me smile and dial better.

And he said, gosh, man,
you're just exhausting my email

and shoulder tapping me.

He's like, here's a read
only user to our SQL database.

And so I downloaded a little MySQL client.

He put the correct permissions on it so
I wouldn't torch the production database,

but I cut my teeth writing SQL
and like grabbing all this information.

And that was so fun.

No nice pretty user interface
your raw table access. Yep.

And to get the information you want,
there's no view for it.

You literally have to go
write a query and.

Yeah, and export it to Excel.

And then do a pivot table and then
graph it out in Excel or whatever.

So I understood databases through that.

And people may be thinking why
is the salesperson writing SQL statements?

It made sense to me.

Excel is a database.

If you really think about it.

And a lot of business people spend time

in Excel,
so SQL didn't seem that much different.

So I liked that part of it.

Got the rep doing this project.

On the software side of it.

I knew in college I had, like I said,
dabbled in WordPress stuff,

so I knew HTML and CSS, but
that interstitial piece of how do you get?

I know how you get HTML on the page.

I know how browsers work,

but I don't know how you get
from the database to the browser.

And that backend software
development was the missing piece for me.

And in the early 2000,
I remember my first job out of school

and I talked about earlier
we were going to redo our website

and the website at the time,
each page was individually coded

and linked together,
and I remember talking with our IT

director who said, okay, Scott,
if you're going to go redo our website,

the website has to be database driven,
like the idea of a content management

system really didn't exist.

So you're cutting your teeth, right?

As that technology
is really coming to fruition. Yep.

I want to go back to you talked about
when you slid that sheet of paper across.

There's something you said
that really, really jumped out at me.

And I think this is something

that is so important and is now actually
challenging me to think about how we.

So you didn't go in with a list
of features for this much money?

We will build feature A feature
B feature C, you approach it.

As for this much,
we'll solve these problems.

For this much we'll solve the next set.

At the end of the day,
nobody cares about features.

You had the foresight.

You had the understanding.

You had the sales acumen very early
in your career to be able to say,

this is we're not selling your features,
we're solving your problems.

Did you just instinctually know
to do that?

Or had you read books or listened to sales
coach, like,

how did you know to do that?

I don't know, but that is a big part
of simple company culture today.

In fact, this is one of my favorite.

Sorry,
I'm kind of jumping forward to present

in our onboarding process
when we hire someone new.

there's a great video.

It is a technical talk.

It was given that a technical conference
at a programing conference.

But the name of the talk is called Hammock
Driven Development.

And it's by this guy, Rich Hickey, who,
you know, was a language architect

for closure, this programing language.

But the nature of the talk
is how to solve problems.

And he references a couple books.

And so the thought is
this most of your time

as a developer is not spent
in the keyboard writing code.

It's actually thinking about what
is the problem actually trying to solve.

And so therefore a lot of your time
should be spent laying down in a hammock

thinking about the problem in the context,
in the what the possible solutions are

and what the trade offs are,

what are the pros and cons
and, you know, risks and all that stuff.

So when someone joins simple,
we send them that talk

and then two days later they get a hammock
in the mail and you're expected

to be away from the keyboard in a hammock,
thinking through what are the problems?

How can we solve these problems better?

So I don't know where it came from
initially.

I don't know if it was something.

I just got ingrained from being around

Dad and Pops and uncle,

but that just
has always seemed natural to me.

Like even it is so such a core thing
and how we work today

and how I've always worked
is like we're solving problems.

Some people don't like that

you can sub out problems
for opportunities or whatnot,

but I feel really strongly
that if you're not creating value

in business by solving problems,
then it's probably immoral.

Like you really should be creating value
by solving these problems.

So for people that are listening,
like write that down

and figure out how to put that
into practice in your business.

And I don't know if it was like this
for you getting simple off the ground,

but for me and for most founders,

you are the sales engine for the company,
at least in the early days.

And again, for people that are listening,
if you're thinking about

getting something started,
you need to be prepared to be selling

and this mindset will help you accelerate
that greatly.

Yeah. It doesn't even feel like selling.

It feels like,
hey, we're discovering something together

along with this customer
or this partner or whomever

of, you know,
what's the highest order bit?

What's the thing
that keeps you up at night?

What's the thing
that if you could automate, you could.

And those are all the opportunities
and things that we look for.

And I think that we just

naturally look for and stack, rank them
and then just knock them out.

Moving around.

You find yourself in Austin
at some part of your career.

Who did you work for
when you first moved to Austin?

I worked for a company called Upstream
Communications.

It was during the 2010 midterms.

This was a company
that it was three parts.

they did mail marketing,
political mail mailers.

They did political consulting,
and they did digital strategy.

It was actually Karl Rove's
former company.

So when he went to work

for the administration,
he had to divest his business interests.

And so that company basically split
with the directors.

We all office in the same office building.

But I went to work for the digital side,

working for campaigns and exploratory
committees during the 2010 midterms.

Tangibly. What was the work like there?

That was actually
my first real developer job.

So I had just wrapped up that project,

that nonprofit project, that first one,
and I was like, I got to be developer.

I really want to close that interstitial
programing back in programing.

And so I tried

finding that in Nashville,
actually couldn't find it.

And I was like,
oh, this looks interesting.

This job opportunity
in Austin for the resume out there.

And they were like,
how quick can you get here?

And I was like,
I can, I don't know, next week.

And then I go there
and their job offer on the spot.

When can you start?

I don't know, I'm brand new married
like I was married three months ago.

They're like, can you start Monday?

I'm like,
which Monday? They're like the next one.

And I'm like, I need to talk to my wife
and figure this out.

So what I told them was I was very clear,

I don't know
a lot of the technical questions

that you're asking me
and talking through some of these,

you know, technical concepts,
I don't know.

I was very clear upfront
this will be learning, but I'm very hungry

and I'll figure it out
and I'll make good on your offer to me.

And I really cut my teeth a lot.

I'm so thankful for some of the lead devs
that were there that kind of took me

under their wing and helped me,

you know, learn the gaps that I had,

and I felt like
I did actually earn good on that.

And by the end of my tenure there,
I was leading the teams,

and it was an intensive, almost boot camp.

I would have really benefited
from some of these technology

and coding bootcamps
that are out there today.

But you got it on the job.

I got it on the job, and I'm so thankful
for the the CEO of that company

that took a chance on me,
and it really helped

launch part of my career in that space.

Being that
this is a political consultancy,

I would imagine
that your business is very seasonal.

I guess there's stuff to do all the time,
but like it really picks back up.

So when you came into this job,
was it with the expectation that after

the election was over,
it was job was done,

or was the expectation that now
this is an indefinite gig?

let's get inside.

I mean, there was very many late
nights there, although it wasn't stated.

There was next bit of cultural expectation

that you would be like
if you left the office at midnight,

or one like, that's what you were doing,
because, you know,

the campaign demanded
that I can't remember

when I rolled off, if I rolled off during
one of the slow seasons, but it's funny.

So we did campaign websites.

We did digital ads.

We did, you know, imagine
a campaign is like a small business

that has this ephemeral,
you know, time to exist.

And then if your horse wins
the race, then, you know, you disband

and I don't know, maybe you get picked up
and you go work in government.

That's another thing I learned.

Campaigns are very different

from a governmental role
and just very, very different.

Did you have aspirations
to go into the government?

No. This was just a tool
for me to learn technology.

But also we built these, you know,
it's like a little small business.

But we also had a donation
platform called us contributions

that had was homegrown
and did political contributions.

And I think I had

approached the CEO,
the guy who was running upstream and said,

hey, it would be good to have some ballast
for the ship and have some normative.

So it wasn't.

So a lot of cash flow and revenue
wasn't so lofty during off seasons.

Maybe if we had like a different customer
segment

we could go after, because the
if you just reskin this application,

we could go for general nonprofits,

we could go for, you know, general payment
processing or whatever.

He was right to say.

Those are completely different businesses,
completely different

go to market strategies
and, you know, whatnot.

So thanks, but no thanks.

And there was a germ there of

I think that would be a interesting thing
to build.

At some point.

The seed was planted.

Yeah.

What was the tipping point for you to say?

My time here is done.

I'm going to I'm
going to move on to the next.

I got recruited away.

I went to work again for this,
little consumer email startup.

The guy named Noah Kagan,
who was number 30 at Facebook, number six

at Mint, kind of a firebrand
at this company called App Sumo.

That was growing really fast.

And I was like,

wow, this is this would be fun to go
on this rocket ride and learn under

under this guy how this at the time
Groupon was really big.

So daily emails and deals with,
you know, Appsumo at the time

the tagline was daily deals for geeks
or you know, for nerds or whatever.

And we'd sell Photoshop bundles and,
you know, online courses and whatnot.

I know that at some point
I've bought WordPress plug ins

and probably half a dozen software
apps through Appsumo.

Yeah.

So I went to work for App
Sumo, and I learned a lot there.

I learned more about marketing there
than I have anywhere else.

One of my favorite things
there was Noah was very clear

on the company and that the company
will have a singular focus.

He was like, there's only three things
this business will ever focus on

profit, growth or engagement.

And we will only focus
on one of those at a time.

So when I was there,
we were only focused on growth.

The only metric, the singular metric
that we were focused

on was net new emails per day.

How did you go about collecting those?

So imagine
you do a deal on a WordPress thing,

or WordPress plugins
or a group of WordPress plugins.

Do people share that deal

with their other friends,
which they then subscribe?

That was the metric on which that deal
was evaluated on.

And was there an incentive to share it
with your friends?

Yeah, yeah, we built all internal tooling
around ads and sharing and going viral

and whatnot,
but I think at the time the list was

85,000 email subscribers.

And it was the goal was,
how do we get the city of Austin?

Yeah.

How do we five access and get 500,000
email subscribers in six months?

And we did it.

So credit to him for

we're only going to focus on net new

email subscribers per day.

And the dev team there had built this

amazing integration with Facebook ads,

where the margins were actually great
on that business as well,

because you're essentially selling
software products

in all the margin that came in from an ad
that was spent, you know, from a deal

that was doing really well,
would go back into refuel, more ad buys.

And so it was just like automated.

And so we'd just spiral out
and we were spending

100 K a week or so on Facebook,
and it was backing out.

Clearly the profit didn't matter
if you were pumping every dollar back

into growth.

Profit was not the motive at that point.

He was running at breakeven.

It was still
the business could have been profitable,

but it was being intentionally
run at break even for growth.

And I'd just never been exposed
to that sort of thinking before.

But I appreciated it.

How did the work vary
from the political consultancy to Appsumo?

And let me break that up into two parts.

How did the work differ
and how did the culture differ?

Yeah, I mean, the culture.

I'll start with the culture question
first,

actually, in some ways is very similar
in the sense that you have a mission

and like, you're really focused on this
singular mission, but in some ways,

the political consulting,
it wasn't necessarily our mission.

We were more partners
in a mission with the candidate.

And when that candidate either
shut down their campaign

or got elected there, you know,
our mission was on to the next thing.

We were hired gun.

We were hired gun. We were mercenary.

And with Appsumo, it was like,
this is a hundred miles an hour.

And like, we're getting after it.

And it was that way all the time.

Was it easier to be bought in at Appsumo,
where

it was the company's mission, than it was
to be bought in at the consultancy?

Yeah, I think that's a fair assessment.

Yeah.

We were responsible for our own success
or failure.

You were there in the growth phase.

Were you there in either
the engagement or profitability phase?

No. Okay.

What was the tipping point
for you to exit?

Appsumo it wasn't my choice.

The founder decided
we're going to move to profit phase,

and we went from 25 people to four. Wow.

Yes. Deep cuts, deep cuts.

But it was very clear.

This is him.

I'm moving to the profits.

You guys, you're not coming.

Along are not going to profit based.

So it's very ruthless.

But it was very clear up front.

This is what we're going to focus on.

I guess it didn't dawn on me until that,

you know, walk on a Friday like,
oh I'm not coming along.

And then the next person goes on a walk

and the next person gets, oh,
and there's a diaspora

now of some of those folks
that I work with.

I still keep in touch with them
and they coincidentally all gone on

to found their own companies
and do their own things, and

each are successful in their own right.

So no bad blood there.

Part of those kind of experiences are it's
hard to see it in the moment,

but they can be good, right?

It created an opportunity for you to go
do something else that has led you here.

And I think back to one of my early jobs,
early in my career,

the company ended up actually

going out of business about 60 days
after my first child was born.

Company just shut its doors
and no severance, no nothing.

Like we didn't
have the option to go on Cobra

because there was no company
plan behind it to offer the Cobra through.

And, you know,
I worked with some of the greatest people

there, and many of them
I talked to on a very regular basis,

one of which is actually part of our team
today.

And I also got a front row seat to what
not to do.

And as painful as it was,

it was a good learning
and growing experience for me.

Yeah, it was for me to
I did challenge him on that walk

because I had numbers
of the deals that I was doing

and I said, man, even if you do switch
to profit, the margin,

my salary as a percentage of the deals
that I've done and like

working on sourcing deals for the list,

like the margins is six hired my salary
like why would you cut someone

that has is bringing in this much
extra margin?

That doesn't make sense to me.

So it was weird because I did
feel kind of like objectively

on that walk, like I was evaluating it,
not from a like,

I was like, you're changing my life
and I don't like my life to be changed.

It really was,

hey, man,

I understand why you're doing this,
but this is making business sense to me.

Like,
is there something else going on here?

How do you answer that?
I don't think he expected it.

I think he really thought like, man, am I.

You're bringing up some good points.

I'm making the right call here.
Call him the question.

Yeah, but.

They ended up going different ways
and we still,

you know, played tennis and hung out.

But yeah, there's some semblance
of a relationship there still after that.

Was it Aetna that came next.

Next was a company called Active Prospect
which was in the CPL or cost

per lead industry like Zillow's
business is basically getting leads

and then selling those leads to mortgage
brokers or realtors or whatever.

So Active Prospect built
this piece of software

that facilitated
delivering those leads into CRM,

like Salesforce or HubSpot or whatever,
and then do an intelligent routing, like,

like imagine you're a realtor
and Zillow says, all right, well,

we'll give you leads.

And you're like,
well, I'm a realtor in the metroplex.

Like,
I don't want leads from Tulsa, Oklahoma.

I don't want to pay for those.

And Zillow was like,
well, you just you get what we get.

Like we our software doesn't have that.

But there was this mechanism
where you could return

a lead in under five seconds
and you wouldn't have to pay for it.

So that tool called Lead Conduit
essentially did that.

Instead of delivering the leads,

the realtor, the mortgage broker,
or whatever going to Zillow said,

instead of delivering
the leads me directly

to delivering the lead conduit,
and then I can go into lead conduit

and configure the parameters
that I don't want.

Like maybe I want leads in the metroplex
where someone was looking at a house

or a mortgage for over $1 million,
and I went, I'm going to do jumbo loans

or something like that.

They had the ability to configure like
their market and only pay for those leads.

And that was what Active Prospect did.

That was technology at scale.

We had a trillion Rowe MySQL database,
and it was

we were processing
60 leads a second like it was

a impressive performance business.

Man, a trillion rows.

That's a lot of data. Yes.

And because of there was a recent
at that time,

tcpa went into effect,
the telecommunications Privacy Act.

The government said you have.

To keep.

Every customer that signs up
for an email list or that option.

You have to have proof of express prior
written consent.

That's why you had to keep that data
around, even though you may not use it.

If you got audited, if you.

Got audited, or you had a suit come,

you had to say, hey,
here's the proof of opt in right here.

So that's why you had these very, very
large data sets on behalf of customers.

Real estate and mortgage in particular,
also highly regulated industries.

Before I started, my company had a project

with a large mortgage company
headquartered on the West Coast,

and we were implementing CRM,
implementing Salesforce.com for them.

And we spent a lot of time
not just with their salespeople

and IT and marketing, but we actually had
to spend a lot of time with their legal

because they were using the system
to generate marketing materials.

If a mortgage broker
wanted to generate a flier,

they were going to do a joint open house
with, with a realtor.

They could go into the system
and they could they could do it.

Well, each one of those
had to have the appropriate footers

that had all the, you know, legal fees
and from state to state, that would vary.

And it would change from time to time.

And if they got audited,
they had to be able to go pull

that document and demonstrate
that they were using the right disclosure

on January 2nd, 2014,
or they could be in in serious trouble.

Yeah. Very similar. Yeah.

I take it you were doing development work
there as well.

Yeah. Okay. What came after that.

And that came after that.

But I started simple
while I was at Active Prospect. On.

Just as the side thing.

Yeah.

So the church that I was going to
at the time,

you know,
when I found this out in nonprofits

and it's a pretty common story,
but the church I was going to at the time

decided that they needed, you know,
rebrand and new website and whatnot.

So myself, along with the designer,
they went to the church,

were Volun told
that the you're on the team to do this

and it was truly just moving
from one content management system

to another, which the scope ended up
being, let's change all the things.

So nothing was off the table.

Email marketing.
Let's move it to MailChimp.

Kids check
in, let's move it to something else.

Let's move volunteer
scheduling to something else.

Let's look at online
giving and I had a particular bone

to pick with online giving the system
that we were using at the time.

First
you had to create an account to give,

then you had to log in to give.

And this was before
like this was probably 2012, 2012

before you have LastPass in one pass
and whatnot.

So the password rules for this online
giving system were so Byzantine

and I would create some obscure
password I'd forget it.

Couldn't find that post it had come back
a month later to to give to my church,

and I can't remember my password.

And I have to reset it.

And my new password has to be different

from my past ten and has to conform
to these ridiculous rules.

And I'd be like, I cannot be the only one
having this problem.

We got to solve this.

And so I look for something off the shelf,
couldn't find something

that fit the bill, and I was like,
I'm a software developer by trade.

I, I can probably build something
really quick and thinking through

what I was exposed to it, US contributions
and the political fundraising,

I'm like, yeah, I think I know
all the ingredients to build this thing.

I just should just put pen to paper
and do it and wrote the first version

bespoke just for that church,

and then kind of dusted my hands off.

And it wasn't until about six months later
that some of the staff

from the church said, hey,
there's a lot of other churches

in that are being planted in Austin
that are asking us what we're using.

Have you thought
about turning this into a business?

And it was like an anvil
on top of my head like,

oh man, it's staring me right,
right in the face.

It wasn't in the back of your mind
the whole time.

Not really

from the technical like code level,
I did not build a multi-tenant database.

I built a single database
specifically for this organization.

So there was no concept of accounts
or sign up or anything like that.

I mean, it was purely
just a bespoke database.

In our organization we talk about projects

and products,
and those are two very different things.

That sounds like a project.

Yes, custom one off real quick,
as you were telling the story

of the pain of the process,
create the account

sign in, give reset your password
a month later, and so forth.

I'm starting to see
where the name simple came from.

Is that accurate?
You're a quick one, Scott.

I don't pick up on many things too fast,
but you may have too obvious for me.

All right.

Six months
after you launch this for your church,

the anvils dropped on your head.
I love that analogy.

I'm going to start using that to talk
about the the epiphanies that I've had.

But I'm going
to I'm gonna talk about the anvil because.

I love Looney Tunes so much. Man.

Our kids don't know what they're
missing out on Saturday morning cartoons.

And yeah, love the Looney Tunes.

What was the first step?

Was it I'm going to go out and find
business.

Is it?

I'm going to start rebuilding this to be
a scalable, multi-tenant application.

I'm thankful in the sense that the the
initial customers just kind of came to me.

There was a guy that ran a design shop

that was kind of reskilling
church websites and nonprofit websites

who had

provided the initial design
for our church's website, and he basically

handed over Photoshop files and said, hey,
cut these up and turn it into something.

So I had a built in pipeline already

through him of going,
hey, I'm working on this other project.

The thing that they have is not great
either.

Could you help with this?

And so I really got pulled into it.

That's a lot
of how our product development goes today.

We do not build spec software or
we don't build anything based on a hunch.

It's almost all of the things
that we build products, services, etc.

are we get pulled into.

People say, hey, we really need X
or we need to solve X problem.

If it's strategic
and it makes a lot of sense

and we feel like we can be really,
really good at it, then we move forward.

But so short answer is
we just got pulled in into stuff.

And were you working at Aetna
at this time?

I left to work on simple for a year.

I was like,
I'm going to I'm going to really go for it

and invest in a lot of time
and writing and developing.

And my wife, who we haven't talked about
that much, was the breadwinner

that year,
and she was so supportive and awesome.

You know, we had just found out
we were pregnant with her firstborn.

It was a big jump, but she kind of pulled
us through doing interior design stuff.

And and then after that, went back
and I got recruited from a guy

who was a colleague at Active Prospect
and he went on to Aetna.

And then he pulled me into to Aetna
about a year or so later.

Roughly what time frame is this?

It's 2000, 13 or 14.

First code was written first
simple was written on July 4th of 2012.

And that was the project
or that that was the project.

Yeah. Okay.

And at that time,
I think it's safe to say, like,

you hadn't incorporated
you hadn't set up a house.

This was I'm just trying to help
my church.

It's a volunteer effort.

At what point did you say,
okay, we're actually going to turn this

into a legitimate business,
and we're going to get an LLC or.

I don't know what your structure is, but,

you know, when did you file
to become a legal entity?

When I started that project,
that initial project

in Nashville,
I'd create an LLC in Tennessee.

And at some point I wrapped
what is now simple

the product into that LLC.

And it wasn't until much, much later
that like read domesticated

that entity into Texas.

I already had some entity that was around.

Okay, you mentioned
we hadn't talked much about your wife.

I think back to you've been married
three months.

You get on a plane to interview
in Austin, Texas.

What was her response?

Obviously you went, but
what was her response when you came home?

I was like, hey babe,
we need to be in Austin on Monday.

Yeah. What did she have
to say? Monday's too quick.

How about a couple Mondays from now?

So she's been so awesome
and so supportive.

It was an adventure.

I think it was probably the best thing
for our marriage.

We didn't know a soul in Texas
and specifically Austin.

And, you know,
when we had gotten married in Nashville.

Like.

We had two distinct friend groups,
I had my friends in Nashville,

she had her friends,

and we would bounce back and forth

on the weekends between hanging out
with different friend groups.

But when we moved to Austin and moved to
Texas, people met us as a unit.

They met and says, like,
these are the Brooks.

And it was
there was no delineation of friend groups.

And so it was great for our marriage
to like, go on this adventure together.

That project that I'd worked on way
back in Nashville and our taxable income

was below the poverty line for sure,
like it was in the 20s.

And I remember getting that offer
from upstream and going,

we made it and it wasn't a big number,
but I was like, we made it.

You can quit your job,
you can do whatever you want.

Like, I got this.

I felt like
we were living high on the hog,

but it was a really fun time
in our marriage.

So you talked about it being an adventure.

And one of the words I'm thinking about
your wife is, this is she adventurous?

And so much more than I am.

Yeah, yeah. It's either risk taker.

I'm definitely not a risk taker.

Despite being a business owner
or an entrepreneur.

I think I'm really risk averse, actually.

I have to see
and we'll talk about that in a little bit.

And and how that plays out that.

Yeah, she frolics and that's why not.

And that is not me.

All right.

You've got a good paying job

and you leave
and you go down to zero income.

You talked about
she was incredibly supportive.

She was the breadwinner.

What was that conversation like
when you said to her, I want to do this?

She's like, yes, let's do it.

No hesitation, no thought, no.

Let's put a plan together
and, you know, pencil this out and

and see
how long we can make the money last.

It was just like.

We'll figure it out
feet first. Yeah. Jump. Yeah.

She's like that.

In retrospect, that is so empowering.

Just like if you have someone who's like,
hey, let's have the race a little bit

like, like where your head's at, like,
let's think through this.

It may have turned out differently,
but to have someone

who's like such a cheerleader and say,
yeah, let's go for it.

Almost every founder we've interviewed has

an incredibly supportive spouse,
and I'm in the same boat.

My wife was much more risk averse
and it was more of a process.

But when we made the decision to do it,

she was and continues to be incredibly,
incredibly supportive.

Yeah, Rachel's name is not on the website.

She is every bit a co-founder
and a founder of this business,

as I am, and probably more so.

I love that.
I mean, she's like chief psychologist.

I would come home and I was and would
say, like, I'm wrestling through this.

She has no idea what Ruby on Rails
is or a Postgres databases.

And but she would sit there and nod
and listen, and that sounds really hard.

And she still does it to this day.

She's so patient and just is a great
listener and cheerleader.

Do you find it hard to talk about.

Work at home?

No. Do you?

Sometimes when it's been a tough day
or we're in a tough season,

I know that my wife has her own,
you know, things going on.

And, you know, a lot of times
I don't want to put that on her.

Now, I'm not a very good poker player
and it shows on my face.

I wear my heart on my sleeve
and it's pretty obvious.

But I think we've we've actually
even more recently started

talking more about those kinds of things
than we have in the past.

And so I guess it goes in spurts.

Yeah, there's some things that I need
time to mull over and think through

before I kind of want to expose it
and I just need to sit with it

and just like,
really wrestle with an idea.

And but it's not like I'm
withholding something from her wanting

to like on the flip side, there are some
things that I get really emotional about

and I'm like, I just come out of my office

immediately from a call and I'm like,
you're not going to believe, you know?

And she is still supportive,
but she's is that psychologist,

which is like,
hey, let's not catastrophize

let's think of this in context,
like what's really going on.

Here's their possible motivations.
Could wow.

Yeah, that's really impressive.

Yeah. She should be a hostage negotiator.

Like you need somebody
with that mentality.

If you've met my three year old,
you realize she is a hostage negotiator.

Fair enough.

Real quick.

We were talking before
we started the interview.

We both use something in our organizations
called Culture Index.

Yeah. What is your pattern?
Oh, I'm a craftsman.

What are you?

I'm an administrator with an ad conflict.

And that creates all kinds of
consternation for me with decision making.

Where are you on the logic side of things?

And I don't remember.

I'd have to go pull up my chart.

I'm low ingenuity, but I'm high logic.

For those of you that aren't familiar,
Culture Index is a personality

profile kind of thing,
similar to desk or Myers-Briggs,

and it's been incredibly helpful
for our organization,

and I think it's been incredibly valuable

in helping us understand ourselves
as much as it is

trying to help us understand
other people in the organization.

And as an aside, I'm
going to say that a quarter

to a third of our people are craftsmen
and we've had excellent

luck with hiring craftsmen,
especially for technical positions.

I was so anti personality tests,
I did not want to do it.

You're going to say something.

I'm the exact same way.
When I was in college.

I graduated college in 2003
and I go to these career fairs.

And the first thing that all of them would

have you do is go through
some kind of personality assessment.

And I thought,
oh my gosh, this another one.

Like, really, there's no value in this.

As I've gotten older and more mature,
I've come to see incredible value.

And in the last few years, between Culture
Index, Strengths

Finders, Enneagram six, Working Geniuses
and I feel like I'm forgetting one.

Like for whatever reason,
I found myself in a situation

where I've taken
a whole whole bunch of these and each one

is like peeling another layer of the onion
and helping me understand myself.

And as I'm reading some of these reports,
I'm like, oh my gosh,

that is me to a tee.

And with one of them,
I think it was Enneagram.

It didn't just say you do these things,
but it actually got into

why I have these behaviors
and thought patterns.

And my mind was just absolutely.
What's your Enneagram?

I'm a nine, I think wing three.

I'm an eight.

I have a great story about Culture
Index, a buddy of mine,

this is a couple of years ago.

We have a position open
for kind of sales at simple.

And this running buddy of mine,
I was like, you know,

he's doing solar sales commission
on solar sales and he's crushing it.

And I'm like, man,
you would be so good working for simple.

And he's like, I'd hate it.

I was offended.

I was like, why would you hate it?

Like, we.

Run together, you know, we hang out like,
I don't understand.

He's like, I would hate it.

We would not work well together.

And I was like, you're wrong.

I'm like,
you should just interview, just interview.

And he wouldn't do it. Fast forward
a couple years.

We implement Culture Index and I'm like,
oh, and I'm

you know, I came around to I'm like,
this is really valuable.

I've learned a lot about myself.

I've learned a lot about our team.

That was, you know, stiff
armed it for the longest time.

But now I'm a believer.

And so I go, hey, John,
I've got this thing called culture index.

I'm not trying to hire you.

I know that you don't want to work here,
but would you just take.

Indulge me. Just indulge me.
Just take this.

And you know, in Culture Index, you create
basically the seed profile of what you

the characteristics of the particular job
and the role and what you think is

would be a great fit for it.

And that's one of the benefits that I say,

if Culture Index is like
this is as objective as you could get

at hiring, at least for culture,
because culture is kind of like,

could I hang out in the airport
with them for four hours?

And what I, what I like him
and he was that for me.

That's why I thought he'd be a great fit.

So he takes it 1% match.

He would have been a train wreck
in this role.

Again, he did not want to take it.

He finally took it,
you know, kicking and screaming.

And I said,
you're not going to believe this,

but it's so good that we didn't work
together.

That's hilarious.
He knew something I didn't.

I was so convinced
that. He'd be a good fit.

Self-awareness is really important. Yeah.

So I'm going to get him some point
some day.

Different role? Yeah.

Different role. Yeah, I'm gonna get him.

Let's go back to getting the business
started.

You took a year
and your wife carried the load.

What was the impetus
for you to go back to a W-2 kind of a job?

I mean, frankly, that simple just didn't
have enough to support a full time gig.

I mean, I spent a lot of heads down time
basically building out the multi-tenancy

of that application
and taking it from a project to a product.

I like the way you phrase that earlier

and that doesn't really drive value
for customers.

It drives value for the business,
but it's not really solving problems

for customers.

But that needed to happen.

You have to do that in the software.

SAS world in particular with, you know,
any sort of payments or money movement.

The challenges is you have to build the
whole pipeline to get a dollar through.

It's not capital intensive in the same way
that you have property, plant

and equipment,

but it is intensive in the sense
that you're committing a lot of time

to get a single thing.

Like there is no MVP,
like the MVP is the whole thing.

I don't know
if you seen that picture online,

but there's a meme of like,
how to draw an owl.

And it's like step one, draw circles.

Step two draw the rest of the owl.

I think it's

actually one of Twilio core values is draw
the rest of the owl. Wow.

And it's funny.

Like if you look at the meme,
it literally is like kids circles.

And then it's like almost like this
beautiful

woodcarving illustration of an owl
that's like has all this fine detail.

That's what it felt like building
the initial version of simple is like,

I'm building the owl,
but there's not a lot of revenue

that I think the first year
it made $43 the entire year in 2014.

You know, today that won't get you
a full family fed at Chick-Fil-A.

It will not.

It will actually not pay your server bill
or your domain

hosting or any cost of that.

I mean, take any line item
and it doesn't doesn't cover it.

Yeah,
that's rough to an acronym and a term

just to help define for listeners
that may not be in the world.

Talk about what multi-tenancy is.

So it's the concept that if you build a
a software product,

you're not going to build a database
for every single customer and spin up

an instance of MySQL, which is a database
engine for every single customer.

You're going to run
all those transactions.

You can think of it like, yeah,
let me map it to Excel.

You're not going to create a
if you have a an Excel spreadsheet

with transactions in it,

you're not going to you can put
all the transactions in one sheet.

You're not going to create different tabs
for different sheets.

You may have a column
that says like customer.

In that way you would be able to run

pivot tables and like do group bys
and filters on that customer.

Oh, so multi-tenancy is essentially

making a single sheet database.

You can build it once
and everybody has the same experience.

That's right.
And then the other was, MVP.

This is not most valuable player.

This is minimum viable product.

So the bare minimum that the application

has to do in order for it
to be useful for somebody.

Yeah, the MVP is essentially the final,

the final thing in the sense
that if you could call something

final,
I mean, there's something we're still

continuing to work and improve on it
today.

Spent a year made $43.

I imagine that today
you guys have iterated on your pricing,

models and have,
you know, got to a much different place,

but you had to go back to a W2 for a time.

How long was that? Six years.

I worked at Aetna.

Funny enough,
this may be surprising to folks.

I actually didn't leave that in until 2020
1st July of 2021. Wow.

So simple has been a side thing
for a long time.

I had four full time employees
while I was still a W2.

What was that. Dynamic like for them?

Hey, our boss actually has another job,
but this is our full time job

to that create
any friction or difficulties with y'all?

I mean,
I think people were just like baffled.

Nobody at my W2 knew about it.

There's a couple like colleagues

that knew about it,
but I don't think they knew the extent.

Like I've got a whole team
that was working on it, and my team

certainly was that simple, was just
just thought it was comical.

It is what it is.

We're going to do it
what we get paid to do.

And yeah, I felt really strongly
that I can be a good follower

when I need to be, but my preference
is to own the whole thing and to lead it.

And then there was something in between.

While I was at upstream,
I started a company with a buddy of mine.

The hypothesis was
it was called Speaker Wiki,

and the hypothesis
was the agency that we worked at.

You didn't need agents.

It was a search engine
and you would check out a speaker

in the same way that you check out
shoes on Zappos or Amazon or whatever.

So we raised a little bit of money
for that.

I mean, it was very short lived,
and I started it with that same guy

from Nashville who was best man
at my wedding, and I was best man in his.

And I realized I did not like that
pressure of having outside capital.

And I didn't
also did not like having a partner

love him,
did not like the partnership dynamic.

So I needed to own and lead

and be the sole
I need to be my own little megalomaniac.

And that now was the seed capital.

My W2 was the seed capital, for
that was only one way to do it.

Something has to support it.

So me carrying
another job was the way to do that.

I trust you were doing well at Aetna
and at a minimum,

you know, you had a steady income.
It was predictable.

I imagine working for a large health
insurance company, you also had great

benefits.

What was the moment that you said,

okay, I can go do simple full time now?

Again, I was pulled into it.

Aetna was a great job
and I had a lot of fun there.

And I continued to learn a lot
in another highly regulated industry.

And I learned about scaling
and automated deployments.

But I talked to my CFO and I was like,
hey, is very clear.

My business partner and simple.

We were not managers.

We did not want to lead people.

It just wasn't our skill set.

Actually,
both of us are craftsmen on Culture Index.

We came to find out later, but we worked
really well together building product.

And so when we looked at each other,
we were like, all right,

we need to hire someone to like,
manage this company.

So we hired a CEO and we were going
to build all the org under him.

And I kept asking him every quarter,

so who can we hire and backfill
some of the stuff like what is non

strategic for you to work on that
we can hire and take off your plate.

And one day he said it's you
we need to hire you.

The business needs more of your time
and I need more of your time.

And I can't compete
with Aetna for your time.

So you need to move. That is. Fascinating.

When he made that statement,
was he needing your time from a

hands on the keyboard execution standpoint
or was it I need to tap

more into the visionary and be able
to help better execute the mission?

I think it was both. I think he needed.

I was kind of the code czar, so like,
I approve every pull request,

even though I may not be writing
all the code

like I'm responsible
for reviewing on it, reviewing it.

And so there'd be features or,
you know, problems that were queued up

and they would queue up
and he'd have customers waiting on them.

I'd be like, I need you to review this,
and I'd be gassed.

I would be.
So I mean, I saw the sun come up.

So I mean, I was doing 8000 hour weeks
like nothing.

Between both jobs.

Doing both jobs like I would finish at six
at Aetna, have dinner.

I go back into my office and I hang up.

I turn the office lights off at two
in the morning, and I'd wake up at 9 a.m.

for a stand up call

with Aetna the next morning and do it
all over, and I did that for not 2 a.m..

All the time, but very, very regularly.

You had some of that early in your career.

You talked about the consultancy
like that was the lifestyle.

Have you always been that way?

Like were you the kid that was studying

till 2:00 in the morning in college
or didn't study?

Yeah.

Not with academia,
but I'm not averse to working hard.

Yeah.

If there's any fault I have, it's
I don't turn off.

I will work very, very hard.

Do you require much sleep?

You know, I got this. Woop.

And I've learned.

That I require a lot of sleep.

So I'm working on that.

I require a lot of sleep, and it shows
very quickly when I don't get enough.

I've always been envious of the people
that can run on 3 or 4 hours of sleep and,

you know, do that for days on end
without it impacting them.

I've got some in-laws that are like that
and I'm just not.

Yeah.

So going back to Jeff,
Jeff is the CEO and.

He. Was like,
this is the right thing for the business.

There's so much growth opportunity here.

And you not being here
is hindering the like day to day

operational side of things.

But there's also such like a big growth
opportunity.

And the either

you don't see it or you see it
and you're not willing to take a big leap.

I mean, the golden handcuffs
are a thing with a large company.

I mean, I was doing really well there,

and I had to walk away from a six
figure stock for investment.

And that's nerve wracking.

I mean, so but it was the
it was totally the right thing to do.

And the business was at a place
where you had enough customers that you

felt good about that, or was it still kind
of a risky proposition for your family?

No, it was not a risky proposition
at that point.

I totally agree with you.
This is the right move.

In fact, I've probably I've probably held
on too long to the blankie.

Yeah, I was just going to say like this
had been sitting there for a while.

The business was at a financial point
that you could have done it earlier.

You didn't see it,

and it really took that conversation
with him to pull you over the line.

Yeah, I.

Guess I thought, like, I'm working,
that doesn't require that much time.

I'd love this phrase of constraints,
forced creativity.

And because I had these W-2 jobs and
and stuff,

we just did things really differently
product wise, sales wise, whatnot.

I actually built my own CRM
inside of simple and built my own

emailing tool
that automated outbound email,

because I was working a full time job,

and I just didn't think that
it really warranted that much of my time.

I can manage as is.

It was very clear
that there was a lot more

that we could be doing,
and I could really accelerate

the growth and the product development
and all that stuff.

But by going full time and the team needed
it, they needed more face time with me.

They needed to hear from the leader
on, hey, where are we going?

What is the next hill
we're going to charge?

Like people need that.

You made that move in 2021.

It was certainly an inflection

point from the standpoint
that it was a big move for the business.

But has it been an inflection point
in terms of sales or other performance?

Yeah.

The funny thing is that since 2017,
we've doubled every year.

So we had been doubling prior to that.

And Jeff was like, dude, we're doubling
and you're not here.

Like, what could we do if you were here?

So it was definitely viable
from that point.

What has your family dynamic been like

since you made the shift
and are only focusing on simple?

Are you still doing the midnight 2 a.m.

kind of nights?

No. I've hired out a lot of that.

I still do rotations on support.

You know, I listen to one of your podcasts

yesterday and there's like,
I like being close to the customer.

I feel like my superpower is being able

to, like, interpret
the challenges that a customer has

and then understand and go well
and then just ask.

Probing questions, not leading ones,

but probing ones and say, what is it
that you're really trying to get at?

And then be like,
that is what we need to build.

A lot of times it could be an issue.

What comes out of that is a new product

or a big enough feature
that bolts on to the existing product.

And I feel like that's
what I'm really good at.

But you have to be close to customers
to do it.

And so a lot of my time is perhaps
not doing the development,

but sitting close to those customers
and trying to understand

and be exposed to those problems.
I love the product side.

I think that if there's anything I hold on
to, it'll be the product development.

But hiring Jeff, our CFO,
he does all the sales and I haven't

I don't do much sales.

I haven't done it since 2019.

He does it a lot better than I do
a lot of the more rote

customer support stuff, where
perhaps our documentation isn't there

and someone writes in, hey,
how do I do this?

Like that goes to a team that manages it.

But most of what I focus on
is kind of the product side of things.

And so therefore,
I have a lot of time to be in the hammock

and think
and I'm more in control of my schedule.

And so therefore my family,

I don't really work after dinner
and get back in the office.

I might on occasion,
but there's not a need to.

It's really self enforced by me.

So yeah, they get to see more
of their husband and dad and hang.

One of the things I love about doing

these interviews is everybody's
story is different.

And before I started doing this podcast,

I kind of had a lot of assumptions
that everybody kind of follow this path.

And the more people I talk to you,
the more different paths I've seen

and your path of there's
a lot of people that have a side business

with their W-2 job, but I've not met many
and probably not anybody

that has built a meaningful business

with employees as a side business.

And one of the things that stands
out to me in that is you have to.

Have really.

Good people to build a meaningful business

where your customers are happy you're
growing, you're doubling every year.

How have you gone about finding
good people?

Fuck or the providence of God?

It's not by my own work, for sure.

Let me step back.

My partner in the business,
he wasn't my partner from the beginning.

He was a guy that I had known
from Nashville.

We went to the same church together.

He's the guy I mentioned who,
you know, caught my ear

and talked about the Roman Empire,
fall of Rome in Las Vegas.

I have a lot of respect for him.

He's the smartest person I know.

And whenever I would go on vacation
and cut from the business

or want to cut from the business, I'd say,
hey, can you babysit everything?

Just kind of manage it.

I would pay him some fee, but he was
a contractor for simple at that point.

And then he was like,

then he started to see what I couldn't see
that there was a lot of opportunity.

And he would say, hey,
I want to partner in this business

and I want to own some of it.

And I was like, I've done the partner
thing, not interested.

And he was like not being a jerk about it.

But he was like, I'm not interested
in being your babysitter for this.

Anytime you go on vacation,
that's not going to happen anymore.

And I'm not interested in contracting
because I can go do something else.

I was like, oh man.

And I said, well, here's my fear.

My fear is that I restructure everything

because I've kind of got
the corporate side dialed in,

and I'm going to restructure stuff for you
to put you as a partner in the business,

and then you're going to leave
in the short term.

This is what I thought it was, and I'm
going to have incurred all this costs

and whatnot.

And he was like,

I'm worried about the long term that
we have some sort of handshake agreement.

And the 25 years from now we have some,

you know, thriving business and that you,
you know, renege on the deal.

And I'm like, well, this is great.

I'm worried about the short
term. You're worried about the long term.

I have a long term orientation.

Like we're aligned.

We're aligned in a lot of ways.

But in this way we're really aligned.

I said, propose something
and I'll there's a 90% chance

I take whatever you propose.

So he proposed it like great.

And that was the first kind of boss

battle or like key thing
that happened in the business.

Great.

I've got someone who is with me in this,
and they're in the trenches,

and I have a lot of mutual respect
for him, and he does for me.

And of course, like people do,
you butt heads.

And we had a lot of that early on.

And but we work really well together.

And then I don't know, was that accident,
was it

me kind of manifesting that or,
you know, God's providence?

I don't know, just common grace.

The church I'm going to guy
comes off the mission field.

He's looking to get a job.

And every job interview
he goes to, they say

what have you been doing for
the past ten years?

I've been a missionary in India.

Like, great. Next, next. Yep.

And so I'm like, I've got this little,
you know, fledgling business.

Like, you want to take a crack at that,
like pay you, but work on

growth and smile.

And for me, that's what I need help with.

So he does it
and I'll be damned if he doesn't close

some of the biggest deals
that we've still got to this day.

Like he closed him and I was like,
hey mayhem, I'm like, this guy is awesome.

I knew at that point
this guy's on borrowed time.

Someone's going to recognize his talent

and he's going to crush it
wherever he goes.

So he ends up going somewhere.

And for the next four years,
I try to court him back,

and he tried to court me as his CTO,
but I won.

I figured out he's like,
I respect him a lot too.

And I said, hey,
do you do any CEO coaching?

Like, I think I need a coach.
I think someone to help me.

And he was like,
yeah, I sell blocks of 20 hours.

And so I bought 20 hours.

And I said, for the. And he was like,
what problems do you face?

And I was like, I need a CEO.

And for the next 20 hours I'm
going to convince you to come work for me.

That's what this 20.

Yeah.

Versus four
is lobbying you to come work for me.

And it worked.

He told me he said I won't come
unless the Lord calls me to Austin.

And so it didn't work like that
didn't work.

But eventually
they originally from Austin.

They have agent parents.
It made sense for them to come back.

And he said,
is that offer still on the table?

I said, you bet it is.

So he's been phenomenal.

Josh has been phenomenal.
Every single person.

I don't know what's happened.

We've just knocked the cover off the ball
with every single person that we've had,

and it feels like
all cylinders are firing.

We've got an awesome team and
I don't think I really appreciated that.

You know,
you mentioned getting older and maturing.

I think where I am now,
I appreciate that a lot.

And we just rebranded.
We used to be simple donation.

Our focus is very simple.

Then we build software
and we build relationships.

That's it. We're in the people business.

So I have, as I've gone on this journey,
I have appreciated more of the people side

of things, the relational side of things
with our customers, with our team.

So yeah, accident.

I think it's how we've gotten
such a great, great staff.

What's the biggest surprise
that has happened along the way?

Good surprise, bad surprise.

You know, we haven't had any like big
like downsides.

There hasn't been like any like
oh my goodness.

You know we're not going to make payroll
or something like that.

I mean we've had trip ups and stuff,
but I don't know

I think probably the surprises,
the success of the business, like

I think my expectation was this was always
a side business and it was held together

with chewing
gum and duct tape and rubber bands.

And perhaps I expected it to fail,

or I expected it to have some term
and it hasn't died.

That's the. Surprise.
That's a surprise. We haven't died.

Which is funny because we celebrated
ten years of marriage

a couple of years ago,
and it was great, this great landmark.

And Rachel said, hey, what's your goal
for the next, next ten years?

And I said, to be married.

And she was like, that's a pretty low bar.

And I'm like, in order to succeed,
first you have to survive.

So there's not many divorce rates
really high, like there's a 5050 chance.

Like if we can survive,

then we can think about the success
and celebrate, you know, everything else.

But yeah, I just
this is my mode right now.

And so I just want to outlast.

And so I'm kind of surprised
that we've lasted this long in some ways.

I'm sure our customers
that might listen to us go, oh my gosh.

What is going on?

It's a really stable business. It's great.

And my goal with
this is to actually run this

for the next 40, 50 years
to operate for a long time.

I noticed I don't remember if it was
on your website or your LinkedIn profile,

but there's a statement that you are
you are building this for the long term.

Yeah.

You're not building this for an exit? Yep.

Has that been your mindset from day one?

There's been a lot of M&A
in the space, mergers and acquisitions.

A lot of our competitors have been bought.

There was a a roll up in 2017 where
there was a big PE firm that put together

$1 billion fund and just started
rolling up church donation companies

and one of the conversation
points on sales calls

with some of our prospective customers
were, are you going to be around?

Are you planning to be bought and sold

and I was like, what is the answer
you want that gets the deal done?

Okay, I love the transparency.

And they were like,
we're looking for a long term partner.

And I was like,
all right, we're a long term partner.

In truth, again,
I have an orientation to run things

for long term and to just, you know,
keep my nose to the grindstone.

And it comes up now
we're getting approached.

You know, every month
there's some new analyst that emails us.

And this really is something that I'm
inspired to run a very, very long time.

I stumbled upon
this group called the Tug Boat Institute.

I don't know if you seen it a couple of
weeks ago, and I'm like my people.

I felt like I opened the door
and it was like all my people.

It's a group of companies that are closely
held, privately owned, no outside

capital and are either still run

by a family, a founder employee owned,

and they plan to have

a kind of a permanent ongoing orientation.

And so and they're very purpose driven.

That's the other thing is they're very,
very purpose driven, mission driven.

And that's why I really want a model.

Simple.

After that,

we are very kind of mission
oriented business based on the customers

that we serve,

and we want to feel like
we're part of their staff

and we're kind of helping them
along with their mission.

I think most founders at some point
have had like,

oh, like, this is really, really bad.

One of our guests from a while back
started a meat market,

and within a couple of weeks of opening
their refrigeration, quit working.

And, you know, that's a bad, bad thing
when you're,

you know, selling perishable food.

You told me a story that probably wouldn't
have been catastrophic, but it hadn't

been one of those, oh my gosh,
what are we going to do kind of moments?

You probably know
the one I'm talking about.

Would you
would you may be sure that real quick.

Yeah.

There's nothing

like figuring out that you've done
something wrong and you're want to puke.

And this was one of those like oh my gosh.

Oh my gosh.
Oh my gosh. Like I'm going to throw up.

And what's the one thing that you should
never do as a payments company.

Double charge someone.

And the way that our system works
is, you know, people set up

recurring donations to these organizations
that they want to support.

And let's say they give, you know, monthly
on the first or whatever.

We just built something or we released
a bit of code, I released a bit of code.

It was me.
Because you're doing the review.

Because I'm doing the reviews
and I actually wrote the original code

for this that introduced this bug.

So it was totally on me and recurring

runs and people are getting
double charged.

I don't know how many people it was
at that time, but this particular day,

like they got double charged,
I saw it happening in real time.

But the thing is,
it's like I couldn't stop it.

I had to let it finish
and then go back and clean up the mess.

So I'm freaking out.

I'm like, all right, now
we're going into crisis management mode.

Let's find out who all was,
which customers were affected.

Let's get in front of this.
Let's call them.

Let's admit it, let's own it.

And let's start telling these customers,

we're happy to reach out to these donors
and admit it on your behalf.

Or if you want to reach out to them, like
how do you different

customers
had different ideas on how to do that.

So I tell my partner
in the business to say, hey,

I need you to to basically see
what the give me a list of people

that were affected and sort
the column by donations.

And so there's one guy that was giving
10-K a month on a transaction.

$120,000 a year. That's a lot of money.
It's a lot of money.

And that day he gave 20 grand.

And I'm like, all right,
that was the largest one that day.

And I said, oh,
I need to call this customer.

I need to call this executive pastor,
like stat.

So I called him

and I said, hey, I'm going to send you
a list of everybody that was affected.

There's a guy on there
who gave 20 K today,

and you probably want
to call that guy first.

And he was so just like he's

been through conflict and crisis before.

So he was just very matter of fact, like

just give me the stuff
and I'll start working.

Panhandle North Texas guy.

It's great to deal with other Texans who
just like have a get it done mentality.

So I'm like, yeah, I'm so sorry, man.

Anything that I'm thinking,
all these customers are going to turn.

They have a right to
they have an expectation of excellence.

We failed to deliver.

This is going to suck.

And so I'm expecting
maybe this is the surprise moment.

In retrospect, it didn't
it didn't seem like that big of a deal.

But at the time
it was I'm going to throw up.

He calls me back.

He says, you're not going to believe this.

I called that guy and he said,
you know what?

I really feel like
we were under giving to our church,

and can you just reset my monthly donation

instead of ten
K a month to 20 K a month? Wow.

And he was like the executive pastor,

you know, on the phone,
he goes, Taylor, what?

Your mistake. God use this.

He's intentionally working amidst
your faults and this was providential.

Yeah.

For this one man's life,
for him to be a better steward of what?

This guy's controlling gas.

And so this was the kick in the pants

that needed him to take further
along in his faith journey.

And he was like,
it's all working out, man.

Like, don't sweat it.

I was like, I've.

Got a lot of other customers to call,
and they may not have the.

Same perspective, but yeah, that is a
that's one of those we haven't done it

since, and there's been a lot of tooling
that prevents that from happening again.

But that is one of those moments of
oh boy.

Yeah, that's a mistake
you don't make twice. No.

Did you lose some customers over it?

Not one.

I think there's an important lesson there.

And I think I've talked about this
in another interview

at some point
and it'll probably come up again.

We have something at my company called
The Mutual Understanding of Imperfection.

Yeah, I've read this. I love it.

And the idea is, if you're selecting us
because you think

that we're going to be perfect,
then you should find somebody else.

Because we are human beings,
we are flawed.

We will make mistakes.

And conversely,
we understand that you, Mr.

Customer, are also humans
and you will make mistakes.

And we need to go into this engagement
knowing that we're both flawed

and we need to be prepared to have grace
for one another when something happens.

And I think there's so much to be said
about the character

qualities
of an organization, of an individual.

When you mess up how you handle it,

and it sounds like you went about it
the exact right way,

at some point you are going to screw up
and you made it right.

Yeah.

That is another thing that I think
is really important for us.

Just culturally, it sets us apart,
perhaps from our customers is saying

when you have an issue like or Johnny
on the spot, we're going to get it done.

And when you email us,
it doesn't go into a support queue

and you get a number back and it's like,
hey, your ticket number or whatever,

I don't do it as much now because
I'm not on those initial sales calls.

But a lot of time I was giving up
my personal phone and going,

if you have any issue, ring me
and we'll get it done.

And I think a lot of people appreciate
that.

They go, I have a direct line to the CEO
who they didn't know was working the job,

but I've got a direct line to the founder
and CEO of this company,

and they don't know how big it is
or how small it is, but that alone,

that having that direct line
to it, to a title like that,

they gave it a lot of credence to that.

And instills a lot of confidence. Yeah.

Did you get many phone calls?

Yeah, I would give

as I still get some today of some of our
and larger organizations.

And now I'm just traffic cop.

I just kind of pass it to the team
and some of the ones I take, but

I actually love it.

I don't try to manufacture crisis

to like, prove that we're human
and we can make things right.

But yeah, don't waste a good crisis,
is what they say in politics, right?

What would you go back and do differently?

Nothing. Have zero regrets?

Maybe join earlier, but I don't know.

I learned a lot.

There was a lot of large scaling things
that I learned in automated deployments,

and a lot of technical stuff from Aetna
that I learned and brought in to sample

a lot of best practices.

I mean, I was exposed to very, very good
engineers, and I benefited from that

and kind of applying that same technology
stack to our business.

So I don't I don't know, I don't know
there's anything I would change,

very happy and satisfied.

So nothing you would change.

But is there any advice
or words of encouragement

that if you could go talk to your younger
self,

that would have helped
make the journey any easier?

If you'd pose the question of what advice
would you give to someone else?

I might answer it differently
than what I would say to myself.

Go for it.

This is something that I again,
we've talked about it earlier,

but just to repeat,

like solving the problems and figuring out
a way to like create value,

I would do work that I know we wouldn't

get paid for just because I knew
it was a the right thing to do.

And I knew that the

it was really valuable to our customers
may not be valuable to us.

And I knew at some point
it would snowball into like,

we'll get it back,
like this is the right thing to do.

It'll come around.

So my advice to a lot of other people
are thinking about starting a business

or thinking about starting
some new venture is find

the problems, solve
those problems, find ways to create value.

Don't focus on.

I've never done a pro forma,

you know, PNL or projection
or anything like that.

It's all just I guess it's B.S.

and they're always wrong.

But if you make something that people want

and you solve the problem, that's
the only thing that I know how to do.

I'm not smart enough to do anything else.

What are the parts of the job
that you enjoy most?

And conversely,
what are the parts of the job that you

wish you didn't have to do?

Yeah, product development is what I enjoy
the most, like the intersection

of technology and customers.

And I love being that bridge.

I love bringing new products to market
and bringing new creative ways

to solve problems to market.

I thrive on that.

The things that I perhaps loathe,
although,

I only do I reconcile our books
four times a year, once a quarter.

Some people might advise that you do
that, you know, maybe monthly.

But yeah, like my brother or my dad
or my uncle, the CPAs, they would.

Say you. Should listen to them.

Yeah, I don't if I had to do it month,
I think I'd loathe it.

But I manage it by only doing it
four times a year,

and I just take a day
and just reconcile everything again.

We have a great team.
We have great people.

I have one direct report.

If I had a lot of direct reports

and that direct report is the CFO, we work

really, really well together
and it doesn't feel like managing.

He manages up.
I don't really mean it's down.

You know,

I think
if I was managing a group of people,

I think that'd be really challenging
for me.

I'm pretty to the point and just,
hey, get it done.

Like I don't have time to talk about
feelings or anything like that.

Just get it done.

Which is not what you want.

A managers persuasion to be.

I'm in the right spot
for where I need to be right now.

I think that's credit to our team.

What's next?

My goal it would be to run this thing
for the next 30 or 40 years.

I feel like I'm chief steward.

I feel less of like a CEO.

I'm very open to the fact that one day
I may not be the founder

and I'll always be the founder,
but one day I may not be the CEO, one day

I may not be the head
of this organization.

And that doesn't scare me.

We've built a great business.

We've built a business that solves
our customer's needs

and is providing a lot of value
to our customers.

It's providing a place where people
can work and provide for their families.

I get texts from employees
that say, I'm on a date night,

and I haven't been on a date

night in three years,
and thank you for this opportunity.

There's nothing better than that
for someone to really feel like

they're pursuing their calling
and yet have time with their family.

So if I can just continue doing this
for the next 30 or 40 years and hear,

well done, good and faithful servant,
that is a good life for me

and invest in my kids and my wife

and in marriage, that's next for me
is just continuing to do that.

Is there any thing
that we didn't talk about that

you wanted to share as part of your story?

I don't think so.

What do you have
in those notes over there?

I haven't actually looked at them at all

for you.

I'll show
you what. I did here in a minute.

So we'll land the plane.

I didn't know if you're trying
to pull something out of me

that you knew, something I didn't know.

I did email Jeff late last night.

Did you really say, hey,
have you got a story?

Have you got to, like, a question
I need to ask?

Course you did.

And I got an out of office, and
I should have thought way ahead on that.

But anyway.

Yeah, well, Taylor Brooks, thanks so much
for being on In the Thick of It, man.

It's been a pleasure.
I really love what you're doing.

I mentioned before we pressed record
how I listen to a lot of your back

episodes, and I want to meet

everybody that you've had on,
and I think this is just really cool.

I'm glad that you created this.
Well thank you.

Our mission is to inspire and encourage
current and future entrepreneurs, and

everybody's got a story,
whether they think they have

wisdom or knowledge to share,
they've got a story.

And there's so much that can be learned
through everybody's story.

So thank you for sharing yours.

Yeah man this Scott thanks.

That was

Taylor Brooks, founder
and CEO of Simple Donation.

To learn more, visit simpledonation.com.

If you or a founder
you know would like to be a guest on In

The Thick of It,
email us at [e-mail]