Anniversary Throwback - #17: Taylor Brooks, Simple Donation - In The Thick of It

Episode Transcript
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(00:00):
Hey, listeners, this is Scott Hollrah.
It's hard to believe that we launchedIn The Thick of It almost a year ago.
As we're nearing our first anniversary,
we're workinghard on a celebratory episode.
In the meantime, we'd love for youto catch up on a founder story
you may have missed.
In today's episode,
I got to chat with Taylor Brooks, founderand CEO of Simple Donation.

(00:23):
From growing up in Atlantato attending Auburn University.
He shares what inspired himto create an online donation platform
for nonprofits and churches, all whilebalancing a full time corporate job.
What you learn about Tayloris that he's all about creating long term
value, building relationships, and takinga stewardship mentality in business.
In fact, his goal is to continue leading

(00:44):
simple donationfor the next 30 to 40 years.
He has a great perspectiveon persistence, consistency
and creating win winsolutions for customers.
I think any new or aspiringfounder will resonate with his approach
to entrepreneurship.
Well,
Taylor, thank you so muchfor making the trip up from Austin.
It's great to have people actuallyin the studio.

(01:04):
We can do remote sessionsand they work great,
but there's always something niceabout seeing people in person.
So thank you so much forfor making the trip and making the effort.
Yeah, it's a pleasure to be here.Thanks for having me.
We always like to start withwhat 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.

(01:26):
I grew up in a great home.
I have a brotherwho I actually just spent time with.
This past weekendwe got the kids together. Was really fun.
Yeah.
Dad owned his own business.
Grandfather owned his own business?
Yeah, just running aroundand played sports a lot.
When I was growing up,I had a really great, great home life.
But. Yeah.
What sports were you into.

(01:46):
Or in track? In high schoolor in cross-country?
In high school?
I played golf, tennis.
I didn't play football or baseball,
but I tried to run the gamuton everything else.
And are you still a runner today?
I've gotten back into it.
Okay, so you got your woopand we were talking earlier.
You got some other new fitnesstracking stuff on the way, so.
I do I've started tracking sleep tracking,and I just hired a coach

(02:09):
this year, a fitness coach.
And so I have a goal this yearof running a sub seven minute mile.
Good for you, man.
501 was my fastest in high school.
Dang.
And I don't think at 41that 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 minutemile at some point in my life.

(02:32):
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?

(02:54):
I did spend a lot of time
just kind of shadowing my dadand shadowing my grandfather,
and I just didn't see the connectionbetween what they were doing
and how they treated and interacted withtheir customers and grew their business.
And what I was learning in school.
Which is funny now,because now I feel like I'm backfilling

(03:14):
a lot of the things that I perhapsdidn't appreciate.
I'm reading a lot of history now.
I'm interested in the Roman Empireand like it would have been pulling teeth
when I was a little kid or in high schoolin college, to appreciate those subjects.
So growing up, I did okay.
In school, I was more focused on sports.

(03:35):
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 menthinking about the Roman Empire.
Were you reading about the Roman Empirebefore this?
Prior? Okay. Right.
So you really have been thinkingabout the Roman Empire? Yes.
Okay, well.
I also have a business partnernow who is a, like, history buff.

(03:56):
Actually, this is funny.
When I knewthat 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 onThis 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,

(04:21):
I've gleaned a lot of historyand 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 alsoor were they working together?
Yeah.
Pops, as he was known,had a plumbing supply company that he ran.
It had.

(04:41):
I mean, imagine what home
and even commercial constructionwas like prior to Home Depot or Lowe's.
It was all mom and pop shops.
So he owned thisplumbing supply company in Atlanta.
I think they had ten locationsat the height.
He ended up selling it.
He was always retiredas long as I'd known him.
And then he went back into starting a CPAfirm,

(05:04):
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 constructioncompany, commercial construction company.
I'm the only non CPA in the familyand coincidentally, I run a business.

(05:28):
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 intersectionof all the family?
And then dad ended up doingcommercial real estate development.
Uncle ended up starting other companies.
So there's an entrepreneurial bugin the Brooks genes.
Yeah.

(05:48):
I'm thinking about your grandfathergoing from plumbing supply to being a CPA.
Those seem worlds apart.
Did he have an accounting backgroundor did he just decide one day
I'm going to go sit for my CPAand start a accounting firm?
He had a JD, CPA prior to this
plumbing supply,but he didn't have the firm.

(06:10):
So while he was running this company at,
you know, Post-acquisitionwhat do I do next?
And so he started the accounting practice.
I think he did it more so to get repswith other business owners than to, like,
try to build a business.
I think he wanted to be in the arenain the game versus

(06:30):
I mean, he didn't need to work.
You mentionedyou'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 somewhatsuccessful 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.

(06:52):
Did or you go.
Where you go. I'mso glad to hear you say that.
You know,I went to Texas A&M and we won't talk
about the most recent matchupthe Aggies won.
I'm so sick of Alabama winning things.
I'm just so sick of it.
And actually it's been kind of nicethe last couple of years.
But yeah in the roll tide War EagleI'm a I'm a war eagle.

(07:13):
So I don't know how you feel about this,how conflicted you are.
And this is perhaps going offtopic of this podcast.
But when Texas plays Alabama.
Do you pull.
For Texas and hold your noseor what do you do?
Man, I was really conflicted that game.
And knowingthat we're going to play Alabama,
I tend to root for the the SEC.

(07:35):
Now next year that's going to change.
But I would rather play an unbeatenAlabama team because it helps us.
If by some miraclewe actually beat Alabama.
I think you get a shotthis 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.

(07:55):
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 Brooksfamily is aviation.
My dad was a Vietnam War veteran and flew.
He was in Vietnam and I was alwaysinterested in planes, I still am.
If you look at my YouTube history,you'll see.
Poker and you'll see ATC.

(08:18):
In plane landings.
I just love aviation.
So I went to Auburn.
I coincidentally, the professional flightprogram is in the School of Business.
I don't know why it's not in the School ofEngineering, but I wanted to be a pilot.
And 911 happened my freshman year.
And something that I thought was moreit was clear to me

(08:40):
then that this is a hobbyI'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 oursout of the Austin or Auburn airport.

(09:00):
So I flew out of Atlantaand got my license there,
and then very quickly realizedthis isn't a career for me.
I still enjoy being around planesand 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 hadthere was germinating

(09:20):
a entrepreneurship degree,and I was really attracted to that.
It was literally the first yearthat they had started it.
So it wasn't fully formed.
They didn't have a lot of specific classesaround 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 bya professor that I really, really liked.

(09:46):
Michael Kincaid, awesome guy.
New venture creation was one classand 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 timewith him after class and drinking beer and
even though he had a one foot in academia,

(10:06):
he also had started several businesses.
And going back to what I said earlier,he really melded those two together.
What is real life experiencelook like with what you're learning here
in the College of Business?
And so that was really formativefor me to go, Like,
I would, I think as a junior at that timewhen I started studying under him,

(10:27):
but really, really enjoyed that.
The professor makes all the difference.
Like it could be one of the mostboring subjects in the world.
But if you got a good professorthat really cares about it and has that,
you know, just dynamic nature, to him,
it didn't really matterwhat the subject matter is.
I 100% agree and I do it the same today.

(10:47):
I feel like I don't read books.
I read authors when I find an authorthat 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.

(11:08):
And these were entrepreneurshipspecific 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 positionand then you argue the opposite position
and then they don't tell you what theI 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.

(11:31):
How would you basically deployresources and capital
and go after this initiativeand what's the right way to do that?
And the story was already written,
but you would kind of workthrough that case and different teams.
The class would be separated into teams,
and then you get to find out likehow it actually played out in real life.

(11:52):
And we would just do those overand over and over.
So it was a lot of reps of workingthrough cases and different situations.
You didn't get the full story,you got the starting elements
and you had to goput it together on your own
and see how your outcome matched upwith the actual case.
That's right.
Yeah, that is really cool.

(12:13):
I wish I had taken a class like thatin 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 fraternityor involved in things on campus?
I was really involved in a campus ministryon campus.
You know, I grew up going to church.

(12:34):
The Brooks Boys had this traditionwhere every Saturday morning
we go to waffle House,and I can just remember my grandfather.
I could hear him
walking up the stairs to comewake me up and singing amazing Grace.
So that's kind of the ethos and worldin which I grew up in.
Was hanging out with my grandfather,
my dad, my brother, and going to waffleHouse and drinking diner coffee

(12:56):
and, scattered,smothered in covered hash browns.
But I feel like it's common to hear peoplego 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 contactwith the director there,

(13:17):
and my faith really grew at Auburn.
It was a really, really formative timefor me and, extremely thankful for that.
And it was throughno 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 Fieldmore than I've been to Auburn.
All right.
What was your first job?

(13:38):
Did you work at all in college?
Did you work in the family business.
And did not work in the family businessin high school?
I grew up having, you know, workingretail 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 workand I did work through
college, building doors, doing carpentryand stuff like that.

(13:58):
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 amcapable of doing.
Need me to hang a ceiling fanor a light fixture?
We're good.
The minuteit becomes plumbing like I'm out.
Yeah, dad would say gas goes boom,so be careful with that.

(14:22):
Good advice.
I actually had a gas leak in our atticnot too long ago, and we had the call
the fire department to get it shut offand then bring in the plumber
to get it all fixed.
And I definitely would not have touchedthat 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 60sgraduate from Auburn, stay in Atlanta,

(14:45):
work for chick fil A, chick fil A,go to family business, family business.
Moved to Nashville, workin 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,

(15:07):
then go to work for a consumeremail 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 rundownfrom post-college to 2023.

(15:30):
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 filA, were you in the I.T.
Like where were you buildingapps for chick fil A?
I was in it, but I was more in hardware.

(15:52):
my responsibility there was to basicallygo around to the different stores,
install new point of sale systemsto train the staff
more so the management on back officesoftware.
How this talks to the corporate officeand then go to the next door.
And by the time that you finishedthe full fleet of stores,

(16:15):
it's time to turn a new pointof 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 countrythrough that experience and learned a lot

(16:36):
is a great so moreso on the the hardware side of it.
There was a team that went into ranall the networking wires
and stuff,but if I was bored, I'd go in at night and
run wiresand yeah, for cable, cat5 and all that.
Chick fil A is a companythat I admire for many, many reasons.
Last weekI went through the drive through one night

(16:58):
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 filA just does so many things, right.

(17:19):
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 waswas it a great place to work for you?
And obviously your role was uniqueand different

(17:39):
than whatmost 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 trackis the current CEO of chick fil A.
No way. Yeah.
So the Cathy familyall went to my high school,

(18:02):
and the other side of the Cathy familywent to Auburn.
And so I am thankful to have an insidepeek at how that all works.
And that yeah, it's a great family.
It's a great business.
They do an amazing job of cultivatingthat culture and protecting it.
I agree with you.
I've got a ten year oldand I'm already thinking your first job

(18:23):
is going to be a chick fil Abecause it's so formative.
They do instill hard workand respect, mutual respect for customers.
And like you,I have a high admiration for that.
That company.
All right.
Nashvillenext 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, Mungerwould call cigar butt businesses,

(18:46):
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 themor liquidate them or whatever.
So I went to workfor one of those businesses,
and I worked there for maybe

(19:07):
8 to 10 months as kind of a gym
and, was working in managing this factorythat 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?

(19:29):
No, I worked as a an agent for keynotespeakers.
So folks that would do collegecommencement speeches or corporate,
you know, rah rah sales meetingsor annual meetings.
I worked in that industry.
Who were the speakersthat were in your portfolio.
At the time?
It was all of the Fox News talking heads.
So, Glenn Beck,Hannity, Colter, Holly North Cavuto.

(19:55):
I spent three months on the roadwith 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?

(20:15):
I'm not one to be starstruck.
I mean just normal people.
But yeah, it was interesting justto see the when someone walks off stage,
what are they like on the bus.
What do they like when they'rehow do they treat other people?
Just all great.I don't have anything negative to say.
Sure.
I imagine that with as many peopleas you were working with,
you probably got to see some that werevery, very kind and some that were not.

(20:40):
Don't name names.
But is that a fair statement?
Yeah.
I mean, you have peoplethat 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 talentor comedians or speakers,
they treat it like a business.
And so there is a needto have some representative
that can advocateon behalf of their schedule.

(21:02):
I mean, they have families.
They, you know, goingtraveling across the country
requiresthem to be away from their family.
And so if they wantthey don't want a private jet
because they're prima donnaand they want to fly on a Gulfstream
everywhere, they want to be backat their kids little League game.
And that's the tool that does it.
So when you communicatethat to a customer, they're like, well,

(21:26):
I don't want to pay for a $30,000round 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 optionsthat are in your range.
So it was an interesting businessto be in.
I call it smile and dial.
That was my rolethere was to drum up business.

(21:47):
And I had a sheet card of 30calls 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 tothat's not inbound you know warm.
Let's work it. You're cold calling.

(22:08):
That's correct.
How has that helpedyou in what you're doing today?
I like to say I have a mentorthat 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

(22:30):
you're not interested in a speakerthis year, are you?
And they go, no, I get great.
Number two, you're not interestedin speaker this year.
And, you know, I couldn't make ita 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 meatand potatoes.

(22:51):
I'm just going to be persistent andconsistent 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 weekendand they brought in a band to play band.
It's called Telephone Friends,which I highly recommend.

(23:12):
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 stepcloser to a yes and every yes.
There's the end of a whole bunch of no'sor something to that effect.
And it was,like I said, worded far better.
And I'm like, wow, like spoton, smiling and dialing, traveling around.

(23:35):
Did you get to go on the Gulf Stream?
Not a Gulf Stream, but I've been on.
Yeah, I traveled on several planeswith 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.

(23:56):
I remember him being cool as a cucumberand going, you know, these planes,
they use these planes and hurricanesto like, measure the wind.
And I was like,that is not helpful right now.
Governor.
My first jobout of college, I worked for an aviation
services company,and we had three company aircraft.
And I can remembergetting so spoiled at 2223,

(24:21):
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 wasa 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.

(24:42):
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.

(25:02):
But if there is one thingthat 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 indulgentspend that I would have.
When you need it, it buys you time.

(25:24):
Oh man, whenyou have three kids under three
and you're trying to go on a trip and haulall 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

(25:47):
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 babybecause I just, you know,
you're on the plane, the baby cries andoh my gosh, your son, he was just perfect.
The trip home was the exact opposite.
Screamed the whole way.

(26:09):
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'rewell beyond that today, thankfully.
But I get what you're saying. Yeah.
All right. Skipping ahead of the jobs.
That you had leading upto starting. Simple.
Where did you learn the most?
You mean as far as technology.

(26:31):
Technology business?
You know, I had a project post, speakerrep courier.
I was like, what do I want to do now?
And I was talking to a buddy that workedfor a nonprofit down in Atlanta,
and he was not complaining,but he was talking
through all these challengesthat he was going through.
And I was thinking,these are solvable problems.

(26:53):
This doesn't seem insurmountable.
Dabbled in,you know, WordPress development.
And and I ranmy own little blog at the time.
This was 2007.
So I think I was a little earlyon, you know, dabbling in technology.
You graduated from college inoh five. Yeah.
And the next time I was like, maybemy roommate at the time was a programmer.

(27:17):
He was on the development teamat 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 waswe had soft phones, IP based phones,
that connected to the homegrown CRM.
It was amazing.Like unbelievable developer.

(27:39):
And he was my roommate.
And I came home from talking to this buddyof mine that worked for this nonprofit,
and I said, hey, my friend was talkingabout all these things.
Do you think that maybe we could cobblesomething 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?

(28:00):
He's like, oh man, it'swe're still have all these issues.
And I slide this little one pagerand 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 range25 K solves these problems.
And then like this bottom 132five this solves all of your problems.

(28:23):
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 bornlike 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.

(28:45):
I get a signed contract for 25 grandand 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 aboutto build some software, and I'm about.

(29:07):
To crack the whip and get you to build it.
So that experience was my first evercustom software development project.
And it was dead on.
Arrival didn't pan out. It delivered.
And it solve the problemsthat we set out to solve.
The thing that I didn't learn wasthat software is never done.

(29:27):
It is never done.
It takes continualgardening and investment
and pruning and it's dynamic.
You know, the systems and servicesthat you're interacting with, they change.
And so therefore you need to change.
I did not anticipatethat when we deliver it,
the requirementsgenerally stayed the same.

(29:47):
But the underlying systemsthat 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, thenthis is going to eat through our margins.
And like this, math just won't work.
We can't pencil this out.

(30:08):
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 sideof the transaction.
And so that was and I really enjoyed
talking through the designsand the schemes and all that stuff.
And it was enough of a puzzle for me.

(30:30):
I just had a toe in the waterat that point
where I knew thatI felt like I would enjoy
being on the developer side of things.
So that was my first entranceinto a technology
like full scope technology product.
I'm like, I could spend my whole careerdoing stuff like this.
One of the things you mentionedwas you enjoyed the

(30:52):
design and architecture of the system.
You didn't have a ton of thatin 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 broughtthat up when I was at this agency,

(31:14):
you know, booking keynote speakersbecause my roommate was the developer,
the CRM that he had builthad 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.

(31:35):
He's like, here's a readonly user to our SQL database.
And so I downloaded a little MySQL client.
He put the correct permissions on it soI wouldn't torch the production database,
but I cut my teeth writing SQLand like grabbing all this information.
And that was so fun.

(31:55):
No nice pretty user interfaceyour raw table access. Yep.
And to get the information you want,there's no view for it.
You literally have to gowrite a query and.
Yeah, and export it to Excel.
And then do a pivot table and thengraph it out in Excel or whatever.
So I understood databases through that.

(32:16):
And people may be thinking whyis 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.

(32:36):
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, butthat 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 getfrom the database to the browser.
And that backend softwaredevelopment was the missing piece for me.

(32:58):
And in the early 2000,I remember my first job out of school
and I talked about earlierwe 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,

(33:19):
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 technologyis really coming to fruition. Yep.
I want to go back to you talked aboutwhen you slid that sheet of paper across.
There's something you saidthat really, really jumped out at me.
And I think this is something

(33:40):
that is so important and is now actuallychallenging me to think about how we.
So you didn't go in with a listof features for this much money?
We will build feature A featureB 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.

(34:01):
You had the foresight.
You had the understanding.
You had the sales acumen very earlyin your career to be able to say,
this is we're not selling your features,we're solving your problems.
Did you just instinctually knowto do that?
Or had you read books or listened to salescoach, like,
how did you know to do that?
I don't know, but that is a big partof simple company culture today.

(34:25):
In fact, this is one of my favorite.
Sorry,I'm kind of jumping forward to present
in our onboarding processwhen we hire someone new.
there's a great video.
It is a technical talk.
It was given that a technical conferenceat a programing conference.
But the name of the talk is called HammockDriven Development.
And it's by this guy, Rich Hickey, who,you know, was a language architect

(34:46):
for closure, this programing language.
But the nature of the talkis how to solve problems.
And he references a couple books.
And so the thought isthis most of your time
as a developer is not spentin the keyboard writing code.
It's actually thinking about whatis the problem actually trying to solve.

(35:07):
And so therefore a lot of your timeshould 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 consand, 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 hammockin the mail and you're expected

(35:29):
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 frominitially.
I don't know if it was something.
I just got ingrained from being around
Dad and Pops and uncle,
but that justhas always seemed natural to me.
Like even it is so such a core thingand how we work today

(35:53):
and how I've always workedis like we're solving problems.
Some people don't like that
you can sub out problemsfor opportunities or whatnot,
but I feel really stronglythat if you're not creating value
in business by solving problems,then it's probably immoral.
Like you really should be creating valueby solving these problems.
So for people that are listening,like write that down

(36:15):
and figure out how to put thatinto practice in your business.
And I don't know if it was like thisfor 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

(36:37):
and this mindset will help you acceleratethat greatly.
Yeah. It doesn't even feel like selling.
It feels like,hey, we're discovering something together
along with this customeror this partner or whomever
of, you know,what's the highest order bit?
What's the thingthat keeps you up at night?
What's the thingthat if you could automate, you could.

(37:00):
And those are all the opportunitiesand things that we look for.
And I think that we just
naturally look for and stack, rank themand then just knock them out.
Moving around.
You find yourself in Austinat some part of your career.
Who did you work forwhen you first moved to Austin?
I worked for a company called UpstreamCommunications.
It was during the 2010 midterms.

(37:22):
This was a companythat 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'sformer company.
So when he went to work
for the administration,he had to divest his business interests.
And so that company basically splitwith the directors.

(37:43):
We all office in the same office building.
But I went to work for the digital side,
working for campaigns and exploratorycommittees during the 2010 midterms.
Tangibly. What was the work like there?
That was actuallymy 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.

(38:06):
I really want to close that interstitialprograming 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 opportunityin 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.

(38:27):
And then I go thereand their job offer on the spot.
When can you start?
I don't know, I'm brand new marriedlike 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 wifeand figure this out.
So what I told them was I was very clear,
I don't knowa lot of the technical questions

(38:50):
that you're asking meand talking through some of these,
you know, technical concepts,I don't know.
I was very clear upfrontthis will be learning, but I'm very hungry
and I'll figure it outand 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 devsthat were there that kind of took me

(39:12):
under their wing and helped me,
you know, learn the gaps that I had,
and I felt likeI 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 benefitedfrom some of these technology
and coding bootcampsthat are out there today.

(39:32):
But you got it on the job.
I got it on the job, and I'm so thankfulfor 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 thatthis is a political consultancy,
I would imaginethat 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

(39:56):
the election was over,it was job was done,
or was the expectation that nowthis is an indefinite gig?
let's get inside.
I mean, there was very many latenights there, although it wasn't stated.
There was next bit of cultural expectation
that you would be likeif you left the office at midnight,
or one like, that's what you were doing,because, you know,

(40:16):
the campaign demandedthat I can't remember
when I rolled off, if I rolled off duringone of the slow seasons, but it's funny.
So we did campaign websites.
We did digital ads.
We did, you know, imaginea campaign is like a small business
that has this ephemeral,you know, time to exist.
And then if your horse winsthe race, then, you know, you disband

(40:39):
and I don't know, maybe you get picked upand you go work in government.
That's another thing I learned.
Campaigns are very different
from a governmental roleand just very, very different.
Did you have aspirationsto go into the government?
No. This was just a toolfor me to learn technology.
But also we built these, you know,it's like a little small business.
But we also had a donationplatform called us contributions

(41:03):
that had was homegrownand 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 ballastfor the ship and have some normative.
So it wasn't.
So a lot of cash flow and revenuewasn't so lofty during off seasons.

(41:23):
Maybe if we had like a different customersegment
we could go after, because theif you just reskin this application,
we could go for general nonprofits,
we could go for, you know, general paymentprocessing or whatever.
He was right to say.
Those are completely different businesses,completely different
go to market strategiesand, you know, whatnot.

(41:43):
So thanks, but no thanks.
And there was a germ there of
I think that would be a interesting thingto 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'mgoing to move on to the next.
I got recruited away.
I went to work again for this, little consumer email startup.

(42:07):
The guy named Noah Kagan,who was number 30 at Facebook, number six
at Mint, kind of a firebrandat this company called App Sumo.
That was growing really fast.
And I was like,
wow, this is this would be fun to goon this rocket ride and learn under
under this guy how this at the timeGroupon was really big.
So daily emails and deals with,you know, Appsumo at the time

(42:31):
the tagline was daily deals for geeksor you know, for nerds or whatever.
And we'd sell Photoshop bundles and,you know, online courses and whatnot.
I know that at some pointI've bought WordPress plug ins
and probably half a dozen softwareapps through Appsumo.

(42:51):
Yeah.
So I went to work for AppSumo, and I learned a lot there.
I learned more about marketing therethan I have anywhere else.
One of my favorite thingsthere was Noah was very clear
on the company and that the companywill have a singular focus.
He was like, there's only three thingsthis business will ever focus on

(43:13):
profit, growth or engagement.
And we will only focuson one of those at a time.
So when I was there,we were only focused on growth.
The only metric, the singular metricthat we were focused
on was net new emails per day.
How did you go about collecting those?
So imagineyou do a deal on a WordPress thing,

(43:35):
or WordPress pluginsor 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 dealwas evaluated on.
And was there an incentive to share itwith your friends?
Yeah, yeah, we built all internal toolingaround ads and sharing and going viral

(43:56):
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 500,000email subscribers in six months?
And we did it.
So credit to him for

(44:18):
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 greaton that business as well,
because you're essentially sellingsoftware products
in all the margin that came in from an adthat was spent, you know, from a deal

(44:41):
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 outand we were spending
100 K a week or so on Facebook,and it was backing out.
Clearly the profit didn't matterif you were pumping every dollar back
into growth.
Profit was not the motive at that point.

(45:03):
He was running at breakeven.
It was stillthe business could have been profitable,
but it was being intentionallyrun at break even for growth.
And I'd just never been exposedto that sort of thinking before.
But I appreciated it.
How did the work varyfrom the political consultancy to Appsumo?

(45:23):
And let me break that up into two parts.
How did the work differand how did the culture differ?
Yeah, I mean, the culture.
I'll start with the culture questionfirst,
actually, in some ways is very similarin the sense that you have a mission
and like, you're really focused on thissingular mission, but in some ways,
the political consulting,it wasn't necessarily our mission.

(45:45):
We were more partnersin a mission with the candidate.
And when that candidate eithershut 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.

(46:06):
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 wasto be bought in at the consultancy?
Yeah, I think that's a fair assessment.
Yeah.
We were responsible for our own successor failure.
You were there in the growth phase.

(46:26):
Were you there in eitherthe engagement or profitability phase?
No. Okay.
What was the tipping pointfor you to exit?
Appsumo it wasn't my choice.
The founder decidedwe're going to move to profit phase,
and we went from 25 people to four. Wow.
Yes. Deep cuts, deep cuts.

(46:47):
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

(47:09):
and the next person gets, oh,and there's a diaspora
now of some of those folksthat I work with.
I still keep in touch with themand they coincidentally all gone on
to found their own companiesand 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'shard to see it in the moment,
but they can be good, right?
It created an opportunity for you to godo something else that has led you here.

(47:32):
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 daysafter my first child was born.
Company just shut its doorsand no severance, no nothing.
Like we didn'thave the option to go on Cobra
because there was no companyplan behind it to offer the Cobra through.

(47:54):
And, you know,I worked with some of the greatest people
there, and many of themI talked to on a very regular basis,
one of which is actually part of our teamtoday.
And I also got a front row seat to whatnot to do.
And as painful as it was,
it was a good learningand growing experience for me.

(48:17):
Yeah, it was for me toI did challenge him on that walk
because I had numbersof the deals that I was doing
and I said, man, even if you do switchto profit, the margin,
my salary as a percentage of the dealsthat I've done and like
working on sourcing deals for the list,
like the margins is six hired my salarylike why would you cut someone

(48:38):
that has is bringing in this muchextra margin?
That doesn't make sense to me.
So it was weird because I didfeel kind of like objectively
on that walk, like I was evaluating it,not from a like,
I was like, you're changing my lifeand 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.

(48:58):
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 waysand we still,
you know, played tennis and hung out.
But yeah, there's some semblanceof a relationship there still after that.
Was it Aetna that came next.

(49:20):
Next was a company called Active Prospectwhich was in the CPL or cost
per lead industry like Zillow'sbusiness is basically getting leads
and then selling those leads to mortgagebrokers or realtors or whatever.
So Active Prospect builtthis piece of software
that facilitateddelivering those leads into CRM,

(49:42):
like Salesforce or HubSpot or whatever,and then do an intelligent routing, like,
like imagine you're a realtorand 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 mechanismwhere you could return

(50:04):
a lead in under five secondsand you wouldn't have to pay for it.
So that tool called Lead Conduitessentially did that.
Instead of delivering the leads,
the realtor, the mortgage broker,or whatever going to Zillow said,
instead of deliveringthe leads me directly
to delivering the lead conduit,and then I can go into lead conduit
and configure the parametersthat I don't want.
Like maybe I want leads in the metroplexwhere someone was looking at a house

(50:29):
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 liketheir 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 processing60 leads a second like it was

(50:52):
a impressive performance business.
Man, a trillion rows.
That's a lot of data. Yes.
And because of there was a recentat that time,
tcpa went into effect,the telecommunications Privacy Act.
The government said you have.
To keep.

(51:13):
Every customer that signs upfor an email list or that option.
You have to have proof of express priorwritten consent.
That's why you had to keep that dataaround, 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, verylarge data sets on behalf of customers.

(51:37):
Real estate and mortgage in particular,also highly regulated industries.
Before I started, my company had a project
with a large mortgage companyheadquartered on the West Coast,
and we were implementing CRM,implementing Salesforce.com for them.
And we spent a lot of timenot just with their salespeople

(51:57):
and IT and marketing, but we actually hadto spend a lot of time with their legal
because they were using the systemto generate marketing materials.
If a mortgage brokerwanted to generate a flier,
they were going to do a joint open housewith, with a realtor.
They could go into the systemand they could they could do it.
Well, each one of thosehad to have the appropriate footers

(52:18):
that had all the, you know, legal feesand 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 demonstratethat they were using the right disclosure
on January 2nd, 2014,or they could be in in serious trouble.

(52:39):
Yeah. Very similar. Yeah.
I take it you were doing development workthere as well.
Yeah. Okay. What came after that.
And that came after that.
But I started simplewhile I was at Active Prospect. On.
Just as the side thing.
Yeah.
So the church that I was going toat 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

(53:00):
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 toldthat the you're on the team to do this
and it was truly just movingfrom one content management system
to another, which the scope ended upbeing, let's change all the things.

(53:22):
So nothing was off the table.
Email marketing.Let's move it to MailChimp.
Kids checkin, let's move it to something else.
Let's move volunteerscheduling to something else.
Let's look at onlinegiving and I had a particular bone
to pick with online giving the systemthat we were using at the time.
Firstyou had to create an account to give,

(53:43):
then you had to log in to give.
And this was beforelike this was probably 2012, 2012
before you have LastPass in one passand whatnot.
So the password rules for this onlinegiving system were so Byzantine
and I would create some obscurepassword I'd forget it.

(54:04):
Couldn't find that post it had come backa 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 conformto these ridiculous rules.
And I'd be like, I cannot be the only onehaving this problem.
We got to solve this.
And so I look for something off the shelf,couldn't find something

(54:27):
that fit the bill, and I was like,I'm a software developer by trade.
I, I can probably build somethingreally quick and thinking through
what I was exposed to it, US contributionsand the political fundraising,
I'm like, yeah, I think I knowall the ingredients to build this thing.
I just should just put pen to paperand do it and wrote the first version

(54:47):
bespoke just for that church,
and then kind of dusted my hands off.
And it wasn't until about six months laterthat some of the staff
from the church said, hey,there's a lot of other churches
in that are being planted in Austinthat are asking us what we're using.
Have you thoughtabout turning this into a business?
And it was like an anvilon top of my head like,

(55:10):
oh man, it's staring me right,right in the face.
It wasn't in the back of your mindthe whole time.
Not really
from the technical like code level,I did not build a multi-tenant database.
I built a single databasespecifically for this organization.
So there was no concept of accountsor sign up or anything like that.
I mean, it was purelyjust a bespoke database.

(55:32):
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 passworda month later, and so forth.
I'm starting to seewhere the name simple came from.

(55:54):
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 monthsafter you launch this for your church,
the anvils dropped on your head.I love that analogy.
I'm going to start using that to talkabout the the epiphanies that I've had.
But I'm goingto I'm gonna talk about the anvil because.
I love Looney Tunes so much. Man.

(56:14):
Our kids don't know what they'remissing 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 findbusiness.
Is it?
I'm going to start rebuilding this to bea scalable, multi-tenant application.
I'm thankful in the sense that the theinitial customers just kind of came to me.

(56:36):
There was a guy that ran a design shop
that was kind of reskillingchurch websites and nonprofit websites
who had
provided the initial designfor 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

(56:57):
through him of going,hey, I'm working on this other project.
The thing that they have is not greateither.
Could you help with this?
And so I really got pulled into it.
That's a lotof how our product development goes today.
We do not build spec software orwe don't build anything based on a hunch.
It's almost all of the thingsthat we build products, services, etc.

(57:22):
are we get pulled into.
People say, hey, we really need Xor we need to solve X problem.
If it's strategicand 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 iswe just got pulled in into stuff.
And were you working at Aetnaat this time?

(57:44):
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 timeand writing and developing.
And my wife, who we haven't talked aboutthat much, was the breadwinner
that year,and she was so supportive and awesome.
You know, we had just found outwe were pregnant with her firstborn.

(58:07):
It was a big jump, but she kind of pulledus through doing interior design stuff.
And and then after that, went backand I got recruited from a guy
who was a colleague at Active Prospectand he went on to Aetna.
And then he pulled me into to Aetnaabout a year or so later.
Roughly what time frame is this?
It's 2000, 13 or 14.

(58:29):
First code was written firstsimple was written on July 4th of 2012.
And that was the projector that that was the project.
Yeah. Okay.
And at that time,I think it's safe to say, like,
you hadn't incorporatedyou hadn't set up a house.
This was I'm just trying to helpmy 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.

(58:51):
I don't know what your structure is, but,
you know, when did you fileto 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 wrappedwhat is now simple
the product into that LLC.
And it wasn't until much, much laterthat like read domesticated

(59:12):
that entity into Texas.
I already had some entity that was around.
Okay, you mentionedwe hadn't talked much about your wife.
I think back to you've been marriedthree months.
You get on a plane to interviewin Austin, Texas.
What was her response?
Obviously you went, butwhat was her response when you came home?
I was like, hey babe,we need to be in Austin on Monday.

(59:34):
Yeah. What did she haveto say? Monday's too quick.
How about a couple Mondays from now?
So she's been so awesomeand so supportive.
It was an adventure.
I think it was probably the best thingfor our marriage.
We didn't know a soul in Texasand specifically Austin.
And, you know,when we had gotten married in Nashville.

(59:56):
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 outwith different friend groups.
But when we moved to Austin and moved toTexas, people met us as a unit.
They met and says, like,these are the Brooks.
And it wasthere was no delineation of friend groups.
And so it was great for our marriageto like, go on this adventure together.

(01:00:20):
That project that I'd worked on wayback in Nashville and our taxable income
was below the poverty line for sure,like it was in the 20s.
And I remember getting that offerfrom 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.

(01:00:40):
I felt likewe were living high on the hog,
but it was a really fun timein our marriage.
So you talked about it being an adventure.
And one of the words I'm thinking aboutyour 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 owneror an entrepreneur.

(01:01:01):
I think I'm really risk averse, actually.
I have to seeand 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 leaveand you go down to zero income.
You talked aboutshe was incredibly supportive.

(01:01:22):
She was the breadwinner.
What was that conversation likewhen 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 togetherand, you know, pencil this out and
and seehow long we can make the money last.
It was just like.
We'll figure it outfeet first. Yeah. Jump. Yeah.
She's like that.
In retrospect, that is so empowering.

(01:01:44):
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.

(01:02:06):
My wife was much more risk averseand 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-founderand a founder of this business,
as I am, and probably more so.

(01:02:27):
I love that.I mean, she's like chief psychologist.
I would come home and I was and wouldsay, like, I'm wrestling through this.
She has no idea what Ruby on Railsis or a Postgres databases.
And but she would sit there and nodand listen, and that sounds really hard.
And she still does it to this day.

(01:02:48):
She's so patient and just is a greatlistener and cheerleader.
Do you find it hard to talk about.
Work at home?
No. Do you?
Sometimes when it's been a tough dayor 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 timesI don't want to put that on her.

(01:03:08):
Now, I'm not a very good poker playerand it shows on my face.
I wear my heart on my sleeveand it's pretty obvious.
But I think we've we've actuallyeven more recently started
talking more about those kinds of thingsthan we have in the past.
And so I guess it goes in spurts.
Yeah, there's some things that I needtime to mull over and think through
before I kind of want to expose itand I just need to sit with it

(01:03:31):
and just like,really wrestle with an idea.
And but it's not like I'mwithholding something from her wanting
to like on the flip side, there are somethings 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

(01:03:53):
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 somebodywith that mentality.
If you've met my three year old,you realize she is a hostage negotiator.
Fair enough.
Real quick.
We were talking beforewe started the interview.

(01:04:15):
We both use something in our organizationscalled 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 ofconsternation 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.

(01:04:36):
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 helpfulfor our organization,
and I think it's been incredibly valuable
in helping us understand ourselvesas much as it is
trying to help us understandother people in the organization.

(01:04:59):
And as an aside, I'mgoing to say that a quarter
to a third of our people are craftsmenand 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 2003and I go to these career fairs.

(01:05:22):
And the first thing that all of them would
have you do is go throughsome 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 CultureIndex, Strengths

(01:05:42):
Finders, Enneagram six, Working Geniusesand I feel like I'm forgetting one.
Like for whatever reason,I found myself in a situation
where I've takena whole whole bunch of these and each one
is like peeling another layer of the onionand 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.

(01:06:04):
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 behaviorsand 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 CultureIndex, a buddy of mine,

(01:06:24):
this is a couple of years ago.
We have a position openfor kind of sales at simple.
And this running buddy of mine,I was like, you know,
he's doing solar sales commissionon 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.

(01:06:45):
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 forwarda couple years.
We implement Culture Index and I'm like,oh, and I'm

(01:07:05):
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, stiffarmed 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.

(01:07:26):
And you know, in Culture Index, you createbasically the seed profile of what you
the characteristics of the particular joband 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 likethis 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 airportwith them for four hours?

(01:07:47):
And what I, what I like himand 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 wreckin 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 worktogether.

(01:08:07):
That's hilarious.He knew something I didn't.
I was so convincedthat. He'd be a good fit.
Self-awareness is really important. Yeah.
So I'm going to get him some pointsome day.
Different role? Yeah.
Different role. Yeah, I'm gonna get him.
Let's go back to getting the businessstarted.
You took a yearand your wife carried the load.
What was the impetusfor you to go back to a W-2 kind of a job?

(01:08:31):
I mean, frankly, that simple just didn'thave enough to support a full time gig.
I mean, I spent a lot of heads down timebasically building out the multi-tenancy
of that applicationand taking it from a project to a product.
I like the way you phrase that earlier
and that doesn't really drive valuefor customers.
It drives value for the business,but it's not really solving problems

(01:08:53):
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 thewhole pipeline to get a dollar through.
It's not capital intensive in the same waythat you have property, plant
and equipment,
but it is intensive in the sensethat you're committing a lot of time

(01:09:14):
to get a single thing.
Like there is no MVP,like the MVP is the whole thing.
I don't knowif 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 drawthe rest of the owl. Wow.

(01:09:38):
And it's funny.
Like if you look at the meme,it literally is like kids circles.
And then it's like almost like thisbeautiful
woodcarving illustration of an owlthat's like has all this fine detail.
That's what it felt like buildingthe initial version of simple is like,
I'm building the owl,but there's not a lot of revenue

(01:09:58):
that I think the first yearit 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 billor your domain
hosting or any cost of that.
I mean, take any line itemand it doesn't doesn't cover it.
Yeah,that's rough to an acronym and a term

(01:10:22):
just to help define for listenersthat may not be in the world.
Talk about what multi-tenancy is.
So it's the concept that if you build aa software product,
you're not going to build a databasefor every single customer and spin up
an instance of MySQL, which is a databaseengine for every single customer.

(01:10:42):
You're going to runall those transactions.
You can think of it like, yeah,let me map it to Excel.
You're not going to create aif you have a an Excel spreadsheet
with transactions in it,
you're not going to you can putall the transactions in one sheet.
You're not going to create different tabsfor different sheets.
You may have a columnthat says like customer.
In that way you would be able to run

(01:11:03):
pivot tables and like do group bysand filters on that customer.
Oh, so multi-tenancy is essentially
making a single sheet database.
You can build it onceand 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.

(01:11:25):
So the bare minimum that the application
has to do in order for itto be useful for somebody.
Yeah, the MVP is essentially the final,
the final thing in the sensethat if you could call something
final,I mean, there's something we're still
continuing to work and improve on ittoday.
Spent a year made $43.
I imagine that todayyou guys have iterated on your pricing,

(01:11:48):
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 20201st July of 2021. Wow.
So simple has been a side thingfor a long time.

(01:12:10):
I had four full time employeeswhile 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 createany 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.

(01:12:32):
Like I've got a whole teamthat was working on it, and my team
certainly was that simple, was justjust thought it was comical.
It is what it is.
We're going to do itwhat we get paid to do.
And yeah, I felt really stronglythat I can be a good follower
when I need to be, but my preferenceis to own the whole thing and to lead it.

(01:12:56):
And then there was something in between.
While I was at upstream,I started a company with a buddy of mine.
The hypothesis wasit was called Speaker Wiki,
and the hypothesiswas the agency that we worked at.
You didn't need agents.
It was a search engineand you would check out a speaker
in the same way that you check outshoes on Zappos or Amazon or whatever.

(01:13:19):
So we raised a little bit of moneyfor that.
I mean, it was very short lived,and I started it with that same guy
from Nashville who was best manat my wedding, and I was best man in his.
And I realized I did not like thatpressure of having outside capital.
And I didn'talso did not like having a partner
love him,did not like the partnership dynamic.
So I needed to own and lead

(01:13:43):
and be the soleI need to be my own little megalomaniac.
And that now was the seed capital.
My W2 was the seed capital, forthat was only one way to do it.
Something has to support it.
So me carryinganother job was the way to do that.
I trust you were doing well at Aetnaand at a minimum,
you know, you had a steady income.It was predictable.

(01:14:04):
I imagine working for a large healthinsurance 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 joband I had a lot of fun there.
And I continued to learn a lotin another highly regulated industry.

(01:14:24):
And I learned about scalingand 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 workedreally well together building product.

(01:14:47):
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 goingto build all the org under him.
And I kept asking him every quarter,
so who can we hire and backfillsome of the stuff like what is non
strategic for you to work on thatwe can hire and take off your plate.

(01:15:10):
And one day he said it's youwe need to hire you.
The business needs more of your timeand I need more of your time.
And I can't competewith Aetna for your time.
So you need to move. That is. Fascinating.
When he made that statement,was he needing your time from a

(01:15:31):
hands on the keyboard execution standpointor was it I need to tap
more into the visionary and be ableto 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 writingall the code
like I'm responsiblefor reviewing on it, reviewing it.

(01:15:52):
And so there'd be features or,you know, problems that were queued up
and they would queue upand 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 weekslike nothing.
Between both jobs.
Doing both jobs like I would finish at sixat Aetna, have dinner.

(01:16:14):
I go back into my office and I hang up.
I turn the office lights off at twoin the morning, and I'd wake up at 9 a.m.
for a stand up call
with Aetna the next morning and do itall 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 consultancylike that was the lifestyle.

(01:16:36):
Have you always been that way?
Like were you the kid that was studying
till 2:00 in the morning in collegeor didn't study?
Yeah.
Not with academia,but I'm not averse to working hard.
Yeah.
If there's any fault I have, it'sI don't turn off.
I will work very, very hard.
Do you require much sleep?
You know, I got this. Woop.

(01:16:57):
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 showsvery quickly when I don't get enough.
I've always been envious of the peoplethat can run on 3 or 4 hours of sleep and,
you know, do that for days on endwithout it impacting them.
I've got some in-laws that are like thatand I'm just not.

(01:17:19):
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 hereis hindering the like day to day
operational side of things.
But there's also such like a big growthopportunity.
And the either

(01:17:39):
you don't see it or you see itand you're not willing to take a big leap.
I mean, the golden handcuffsare a thing with a large company.
I mean, I was doing really well there,
and I had to walk away from a sixfigure stock for investment.
And that's nerve wracking.
I mean, so but it was theit was totally the right thing to do.
And the business was at a placewhere you had enough customers that you

(01:18:02):
felt good about that, or was it still kindof a risky proposition for your family?
No, it was not a risky propositionat that point.
I totally agree with you.This is the right move.
In fact, I've probably I've probably heldon too long to the blankie.
Yeah, I was just going to say like thishad been sitting there for a while.
The business was at a financial pointthat you could have done it earlier.

(01:18:23):
You didn't see it,
and it really took that conversationwith 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 andand stuff,
we just did things really differentlyproduct wise, sales wise, whatnot.

(01:18:48):
I actually built my own CRMinside of simple and built my own
emailing toolthat automated outbound email,
because I was working a full time job,
and I just didn't think thatit really warranted that much of my time.
I can manage as is.
It was very clearthat there was a lot more

(01:19:08):
that we could be doing,and I could really accelerate
the growth and the product developmentand all that stuff.
But by going full time and the team neededit, they needed more face time with me.
They needed to hear from the leaderon, hey, where are we going?
What is the next hillwe're going to charge?
Like people need that.
You made that move in 2021.

(01:19:29):
It was certainly an inflection
point from the standpointthat it was a big move for the business.
But has it been an inflection pointin 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 doublingand you're not here.

(01:19:50):
Like, what could we do if you were here?
So it was definitely viablefrom that point.
What has your family dynamic been like
since you made the shiftand 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.

(01:20:11):
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, interpretthe challenges that a customer has
and then understand and go welland then just ask.
Probing questions, not leading ones,

(01:20:31):
but probing ones and say, what is itthat 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 featurethat bolts on to the existing product.
And I feel like that'swhat I'm really good at.
But you have to be close to customersto do it.
And so a lot of my time is perhapsnot doing the development,

(01:20:52):
but sitting close to those customersand trying to understand
and be exposed to those problems.I love the product side.
I think that if there's anything I hold onto, 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.

(01:21:13):
He does it a lot better than I doa lot of the more rote
customer support stuff, whereperhaps 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 onis kind of the product side of things.
And so therefore,I have a lot of time to be in the hammock

(01:21:35):
and thinkand I'm more in control of my schedule.
And so therefore my family,
I don't really work after dinnerand 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 moreof their husband and dad and hang.
One of the things I love about doing
these interviews is everybody'sstory is different.

(01:21:59):
And before I started doing this podcast,
I kind of had a lot of assumptionsthat 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'sa lot of people that have a side business
with their W-2 job, but I've not met manyand probably not anybody

(01:22:20):
that has built a meaningful business
with employees as a side business.
And one of the things that standsout to me in that is you have to.
Have really.
Good people to build a meaningful business
where your customers are happy you'regrowing, you're doubling every year.

(01:22:42):
How have you gone about findinggood 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 knownfrom Nashville.
We went to the same church together.
He's the guy I mentioned who,you know, caught my ear

(01:23:03):
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 vacationand 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 wasa contractor for simple at that point.
And then he was like,

(01:23:23):
then he started to see what I couldn't seethat 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 partnerthing, not interested.
And he was like not being a jerk about it.
But he was like, I'm not interestedin being your babysitter for this.
Anytime you go on vacation,that's not going to happen anymore.

(01:23:46):
And I'm not interested in contractingbecause 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 gotthe corporate side dialed in,
and I'm going to restructure stuff for youto put you as a partner in the business,
and then you're going to leavein the short term.

(01:24:07):
This is what I thought it was, and I'mgoing to have incurred all this costs
and whatnot.
And he was like,
I'm worried about the long term thatwe 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 shortterm. You're worried about the long term.

(01:24:27):
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 somethingand 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 thingthat happened in the business.

(01:24:48):
Great.
I've got someone who is with me in this,and they're in the trenches,
and I have a lot of mutual respectfor 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?

(01:25:09):
I don't know, just common grace.
The church I'm going to guycomes off the mission field.
He's looking to get a job.
And every job interviewhe goes to, they say
what have you been doing forthe 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.

(01:25:30):
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 itand I'll be damned if he doesn't close
some of the biggest dealsthat 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 pointthis guy's on borrowed time.

(01:25:51):
Someone's going to recognize his talent
and he's going to crush itwherever 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?

(01:26:12):
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'mgoing to convince you to come work for me.
That's what this 20.
Yeah.
Versus fouris lobbying you to come work for me.

(01:26:34):
And it worked.
He told me he said I won't comeunless the Lord calls me to Austin.
And so it didn't work like thatdidn't work.
But eventuallythey 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.

(01:26:57):
Josh has been phenomenal.Every single person.
I don't know what's happened.
We've just knocked the cover off the ballwith every single person that we've had,
and it feels likeall cylinders are firing.
We've got an awesome team andI 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.

(01:27:19):
Our focus is very simple.
Then we build softwareand 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 thingswith our customers, with our team.
So yeah, accident.
I think it's how we've gottensuch a great, great staff.

(01:27:40):
What's the biggest surprisethat has happened along the way?
Good surprise, bad surprise.
You know, we haven't had any like biglike downsides.
There hasn't been like any likeoh my goodness.
You know we're not going to make payrollor 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

(01:28:02):
I think my expectation was this was alwaysa side business and it was held together
with chewinggum and duct tape and rubber bands.
And perhaps I expected it to fail,
or I expected it to have some termand it hasn't died.
That's the. Surprise.That's a surprise. We haven't died.
Which is funny because we celebratedten years of marriage

(01:28:24):
a couple of years ago,and it was great, this great landmark.
And Rachel said, hey, what's your goalfor 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 ratesreally high, like there's a 5050 chance.

(01:28:44):
Like if we can survive,
then we can think about the successand celebrate, you know, everything else.
But yeah, I justthis is my mode right now.
And so I just want to outlast.
And so I'm kind of surprisedthat we've lasted this long in some ways.
I'm sure our customersthat might listen to us go, oh my gosh.
What is going on?
It's a really stable business. It's great.

(01:29:06):
And my goal withthis is to actually run this
for the next 40, 50 yearsto operate for a long time.
I noticed I don't remember if it wason your website or your LinkedIn profile,
but there's a statement that you areyou are building this for the long term.
Yeah.
You're not building this for an exit? Yep.

(01:29:26):
Has that been your mindset from day one?
There's been a lot of M&Ain the space, mergers and acquisitions.
A lot of our competitors have been bought.
There was a a roll up in 2017 wherethere was a big PE firm that put together
$1 billion fund and just startedrolling up church donation companies
and one of the conversationpoints on sales calls

(01:29:49):
with some of our prospective customerswere, are you going to be around?
Are you planning to be bought and sold
and I was like, what is the answeryou 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

(01:30:11):
for long term and to just, you know,keep my nose to the grindstone.
And it comes up nowwe're getting approached.
You know, every monththere's some new analyst that emails us.
And this really is something that I'minspired to run a very, very long time.
I stumbled uponthis group called the Tug Boat Institute.
I don't know if you seen it a couple ofweeks ago, and I'm like my people.

(01:30:35):
I felt like I opened the doorand it was like all my people.
It's a group of companies that are closelyheld, 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.

(01:30:56):
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 missionoriented business based on the customers
that we serve,
and we want to feel likewe're part of their staff
and we're kind of helping themalong with their mission.

(01:31:17):
I think most founders at some pointhave had like,
oh, like, this is really, really bad.
One of our guests from a while backstarted a meat market,
and within a couple of weeks of openingtheir refrigeration, quit working.
And, you know, that's a bad, bad thingwhen you're,
you know, selling perishable food.
You told me a story that probably wouldn'thave been catastrophic, but it hadn't

(01:31:40):
been one of those, oh my gosh,what are we going to do kind of moments?
You probably knowthe one I'm talking about.
Would youwould you may be sure that real quick.
Yeah.
There's nothing
like figuring out that you've donesomething 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 shouldnever do as a payments company.

(01:32:04):
Double charge someone.
And the way that our system worksis, you know, people set up
recurring donations to these organizationsthat they want to support.
And let's say they give, you know, monthlyon the first or whatever.
We just built something or we releaseda bit of code, I released a bit of code.
It was me.Because you're doing the review.
Because I'm doing the reviewsand I actually wrote the original code

(01:32:26):
for this that introduced this bug.
So it was totally on me and recurring
runs and people are gettingdouble charged.
I don't know how many people it wasat 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 finishand then go back and clean up the mess.

(01:32:47):
So I'm freaking out.
I'm like, all right, nowwe'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 donorsand admit it on your behalf.

(01:33:08):
Or if you want to reach out to them, likehow do you different
customershad different ideas on how to do that.
So I tell my partnerin the business to say, hey,
I need you to to basically seewhat the give me a list of people
that were affected and sortthe column by donations.
And so there's one guy that was giving10-K a month on a transaction.

(01:33:31):
$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 youa list of everybody that was affected.
There's a guy on therewho gave 20 K today,

(01:33:53):
and you probably wantto 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 stuffand I'll start working.
Panhandle North Texas guy.
It's great to deal with other Texans whojust like have a get it done mentality.
So I'm like, yeah, I'm so sorry, man.

(01:34:16):
Anything that I'm thinking,all these customers are going to turn.
They have a right tothey have an expectation of excellence.
We failed to deliver.
This is going to suck.
And so I'm expectingmaybe this is the surprise moment.
In retrospect, it didn'tit didn't seem like that big of a deal.
But at the timeit was I'm going to throw up.
He calls me back.
He says, you're not going to believe this.

(01:34:37):
I called that guy and he said,you know what?
I really feel likewe were under giving to our church,
and can you just reset my monthly donation
instead of tenK a month to 20 K a month? Wow.
And he was like the executive pastor,
you know, on the phone,he goes, Taylor, what?

(01:34:58):
Your mistake. God use this.
He's intentionally working amidstyour 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 furtheralong in his faith journey.
And he was like,it's all working out, man.

(01:35:19):
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 athat's one of those we haven't done it
since, and there's been a lot of toolingthat prevents that from happening again.
But that is one of those moments ofoh boy.
Yeah, that's a mistakeyou don't make twice. No.

(01:35:40):
Did you lose some customers over it?
Not one.
I think there's an important lesson there.
And I think I've talked about thisin another interview
at some pointand it'll probably come up again.
We have something at my company calledThe Mutual Understanding of Imperfection.
Yeah, I've read this. I love it.
And the idea is, if you're selecting usbecause you think

(01:36:01):
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 humansand you will make mistakes.
And we need to go into this engagementknowing that we're both flawed
and we need to be prepared to have gracefor one another when something happens.

(01:36:26):
And I think there's so much to be saidabout the character
qualitiesof an organization, of an individual.
When you mess up how you handle it,
and it sounds like you went about itthe exact right way,
at some point you are going to screw upand you made it right.
Yeah.
That is another thing that I thinkis really important for us.

(01:36:49):
Just culturally, it sets us apart,perhaps from our customers is saying
when you have an issue like or Johnnyon 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 becauseI'm not on those initial sales calls.
But a lot of time I was giving upmy personal phone and going,

(01:37:10):
if you have any issue, ring meand we'll get it done.
And I think a lot of people appreciatethat.
They go, I have a direct line to the CEOwho they didn't know was working the job,
but I've got a direct line to the founderand CEO of this company,
and they don't know how big it isor how small it is, but that alone,
that having that direct lineto it, to a title like that,

(01:37:32):
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 ourand larger organizations.
And now I'm just traffic cop.
I just kind of pass it to the teamand some of the ones I take, but
I actually love it.
I don't try to manufacture crisis
to like, prove that we're humanand we can make things right.

(01:37:53):
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 thingsthat I learned in automated deployments,
and a lot of technical stuff from Aetnathat I learned and brought in to sample

(01:38:14):
a lot of best practices.
I mean, I was exposed to very, very goodengineers, and I benefited from that
and kind of applying that same technologystack to our business.
So I don't I don't know, I don't knowthere's anything I would change,
very happy and satisfied.
So nothing you would change.
But is there any adviceor words of encouragement

(01:38:35):
that if you could go talk to your youngerself,
that would have helpedmake the journey any easier?
If you'd pose the question of what advicewould you give to someone else?
I might answer it differentlythan 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 outa way to like create value,

(01:38:58):
I would do work that I know we wouldn't
get paid for just because I knewit was a the right thing to do.
And I knew that the
it was really valuable to our customersmay not be valuable to us.
And I knew at some pointit would snowball into like,
we'll get it back,like this is the right thing to do.
It'll come around.

(01:39:18):
So my advice to a lot of other peopleare thinking about starting a business
or thinking about startingsome new venture is find
the problems, solvethose problems, find ways to create value.
Don't focus on.
I've never done a pro forma,
you know, PNL or projectionor anything like that.
It's all just I guess it's B.S.

(01:39:40):
and they're always wrong.
But if you make something that people want
and you solve the problem, that'sthe only thing that I know how to do.
I'm not smart enough to do anything else.
What are the parts of the jobthat 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 enjoythe most, like the intersection

(01:40:00):
of technology and customers.
And I love being that bridge.
I love bringing new products to marketand 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 booksfour times a year, once a quarter.
Some people might advise that you dothat, you know, maybe monthly.

(01:40:23):
But yeah, like my brother or my dador 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 itfour times a year,
and I just take a dayand just reconcile everything again.
We have a great team.We have great people.

(01:40:43):
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 togetherand it doesn't feel like managing.
He manages up.I don't really mean it's down.
You know,
I thinkif I was managing a group of people,
I think that'd be really challengingfor me.

(01:41:04):
I'm pretty to the point and just,hey, get it done.
Like I don't have time to talk aboutfeelings or anything like that.
Just get it done.
Which is not what you want.
A managers persuasion to be.
I'm in the right spotfor 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 thingfor the next 30 or 40 years.

(01:41:29):
I feel like I'm chief steward.
I feel less of like a CEO.
I'm very open to the fact that one dayI 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 headof this organization.
And that doesn't scare me.
We've built a great business.
We've built a business that solvesour customer's needs

(01:41:52):
and is providing a lot of valueto our customers.
It's providing a place where peoplecan work and provide for their families.
I get texts from employeesthat 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 thatfor someone to really feel like
they're pursuing their callingand yet have time with their family.

(01:42:16):
So if I can just continue doing thisfor 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 meis just continuing to do that.
Is there any thingthat we didn't talk about that
you wanted to share as part of your story?

(01:42:37):
I don't think so.
What do you havein those notes over there?
I haven't actually looked at them at all
for you.
I'll showyou what. I did here in a minute.
So we'll land the plane.
I didn't know if you're tryingto 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 questionI need to ask?

(01:42:57):
Course you did.
And I got an out of office, andI should have thought way ahead on that.
But anyway.
Yeah, well, Taylor Brooks, thanks so muchfor 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 recordhow 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.

(01:43:20):
I'm glad that you created this.Well thank you.
Our mission is to inspire and encouragecurrent 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 learnedthrough everybody's story.
So thank you for sharing yours.
Yeah man this Scott thanks.

(01:43:49):
That was
Taylor Brooks, founderand CEO of Simple Donation.
To learn more, visit simpledonation.com.
If you or a founderyou know would like to be a guest on In
The Thick of It,email us at intro@founderstory.us

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Anniversary Throwback - #17: Taylor Brooks, Simple Donation