#42: Reagan and Elle Pugh

In this episode, we feature our first-ever husband and wife duo—Reagan and Elle Pugh—each with their own thriving entrepreneurial ventures. Together, they share the personal and professional experiences that not only brought them together but also fuel their mutual support in business.

We explore key topics like the value of mentorship, navigating financial highs and lows, and the power of open communication with business partners. 

Reagan, a motivational speaker and author, and Elle, the founder of an Enneagram coaching business and luxury greenery company, Gracious Garlands, also reveal their future plans and insights on entrepreneurship.

Tune in for an inspiring conversation on balancing marriage and business!

***

About Reagan
Reagan Pugh is a writer and speaker dedicated to helping individuals and teams find more meaning in life and work. With a focus on emotional intelligence and self-awareness, Reagan delivers keynote speeches and workshops to thousands of people each year, having worked with organizations like Facebook, Pepsi, Whirlpool, Cardinal Health, all branches of the US Military, Meals on Wheels, and the American Red Cross. Prior to writing and speaking full time, Reagan guided programs on storytelling and culture at companies like Nike, Western Digital, and Kimberly Clark as Chief Storyteller for a global management consulting firm. From 2009 to 2011, Reagan served as a tenth-grade English teacher with Teach for America on the Rosebud Reservation in South Dakota. During that time, he  launched a theater program that, in its inaugural year, won the state one- act play competition for the first time. Reagan has instructed at Texas State University, Trinity University, and Angelo State University. He continues to prioritize speaking to student audiences throughout the United States, having visited over 50 college campuses to date. Reagan is a TEDx speaker and frequent podcast guest. His first book, Too Emotional: Overcome the Thunderstorm of Feelings, Shame and Self-Doubt, was published in May of 2024. He lives with his wife, Elle, and their white Labrador, Lily, in Austin, Texas.

To learn more, visit https://www.reaganpugh.com/

About Elle
Elle Pugh is a Certified Enneagram Facilitator and Coach, Registered Nurse, and entrepreneur dedicated to holistic wellness and personal growth. Whether it’s one-on-one coaching, training leadership teams at multiple Fortune 100 companies, or designing workshops for startup teams, Elle is committed to helping individuals and organizations understand themselves so they can find healing and renewed connection with one another. Elle started her career in the pediatric cardiac ICU. After realizing the US healthcare system is not designed to heal people, she left the bedside to take a role as the first employee at a healthcare startup. There she grew the team to over 30 medical professionals and formed her working philosophy that healthy organizations are made up of healthy individuals. Elle's entrepreneurial endeavors also extend to Gracious Garlands, a luxury wreath company known for its farm-fresh products and a made-to-order catering company that helped her make money in college. An unabashed Swifty, she still loves to cook and her goal is to ski 50 plus days every winter. 

To learn more about Beyond Enneagram, visit https://www.beyondyourtype.co/

To learn more about Gracious Garlands, visit https://graciousgarlands.com/

***

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Creators & Guests

Host

Scott Hollrah

Founder & CEO of Venn Technology

Guest

Elle Pugh

Founder & CEO of Gracious Garlands and Beyond Enneagram

Guest

Reagan Pugh

Speaker & Author of Too Emotional

What is In The Thick of It?

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

The thing that I avoid the most, that is always

the most important thing, is to go out and to

socialize my challenges with people who've been there before and

to try and find myself a new mentor.

So you just kind of boldly have

to say, this is what I'm worth.

There's a little bit of fake it till you make it

and you know so much more than you think you do,

and it just is getting in there, doing it.

Welcome to In The Thick of It.

I'm your host, Scott Hollrah.

For the first time on In The Thick of It,

we are highlighting a husband and wife duo

that each have their own entrepreneurial ventures.

Reagan and Elle Pugh shared the experiences

that not only brought them together, but

led them to support each other's pursuits.

This episode dives into the importance of

mentorship, planning for financial ups and downs,

and open communication with business partners.

Reagan is a motivational speaker and author, while

Elle runs an Enneagram coaching business and a

luxury greenery company called Gracious Garlands.

Tune in to hear about Reagan

and Elle's endeavors and future plans.

All right, I say this all the time.

I'm excited about the episode today,

but for a totally different reason.

This is a very different episode

than we've done in the past. I actually don't know.

We might have had one or two times where we've had

a founder and a co-founder on at the same time,

but this is the first time that we've ever had a

husband and wife who both have their own entrepreneurial ventures, that

have their own businesses that are on at the same time.

And that's part of why I wanted to

do this episode today was to talk about

this from just a whole different perspective.

Yes, we're going to get into the business, but

also want to get into what's the dynamic like

with both of you having your own businesses.

We have Reagan and Elle Pugh,

based out of Austin, Texas.

Reagan is a speaker and an author who just

actually had a new book come out in May.

Elle, you run multiple businesses beyond your type

and gracious garlands, which those, I think, are

probably very different from one another.

So can't wait to hear how that came about.

And so, anyway, yeah, let's jump into it.

Y'all are down in Austin today.

Reagan, I know you grew up in the Dallas area.

Ellie, what about you? Where's home?

I'm from Nashville, Tennessee. Love Nashville.

Yeah, Nashville and Austin.

Kind of sister cities. Yeah.

You know, without a doubt.

Well, Elle, let's start with you.

So what was growing up like in Nashville?

Did you live there all the way through, or did

you move around and kind of ended in Nashville?

My whole childhood was spent in Nashville,

and Reagan and I talk a lot

about the differences in our childhoods.

And I was brought home from the hospital to one

room, and I left for college in that same room. Wow.

So neither of my parents are from Nashville.

They're from North Carolina, but it is still home.

It's still home for me.

My parents don't live there anymore.

They moved back to North Carolina.

But we just have a very tight knit community in

Nashville that I am just so, so grateful to have.

And it was a wonderful place to grow up

and went to some different schools, but a lot

of the schools kind of fed into other schools.

And so that made transitioning schools easy because

I always had familiar faces, was privileged enough

to grow up going to private school.

So smaller, really nurturing environment.

And that's the very high level

understanding of my growing up.

Do you have siblings or you an only child?

Yes, I have an older brother.

He is four years older.

And what kinds of things were you into as a kid? Gosh.

So I loved being outside.

We had an amazing neighborhood, so we were always outside

playing in the trees, playing freeze tag at night.

We were able to roam, and that was just amazing.

I played a lot of sports.

I played every sport until high school.

Danced in the summertime.

I was swimming, doing swim team,

and going to summer camp.

Learning to sail and camp is a huge part of my life.

So just very active, very active little kid, if I wish.

So I'm an Enneagram coach, which

I'm sure we will get into.

And I wish I had known, particularly

in high school, about the Enneagram to

at least maybe identify the different types.

And I would have probably been able to

tell you I was a seven and to

understand how that played out in my life.

Just interested and excited about everything.

So that was little Elle, and I'm

not much different from that today.

It sounds like you had that idyllic childhood

that kids don't have anymore, where, you know,

you're playing until the streetlight comes on and

mom and dad call you home for dinner.

And life just isn't like

that many places anymore, truly.

And we really, we've talked about that a lot recently

as we're trying to start our own family and the

grief around that, that we just really would love to

give our children that, you know, the anxious generation is

a huge topic in our friend group.

And so, yeah, I was very, very blessed and

privileged to grow up the way I did. That's awesome.

How did you make your way to Texas?

Well, I went to Ole Miss, and a lot of Texans

go to Ole Miss, and so I ended up moving to

Dallas after college, followed my college boyfriend back home, back to

Texas, left Texas, said, I'll never come back, and then ended

up back in Austin, and several years later, met Reagan and

moved to Austin nine years ago. Awesome.

I've got a niece at Ole Miss right now.

She's a sophomore.

She's loving, loving it. Hotty Toddy. That's right.

I think she found the right spot for her.

It's a great, great place.

All right, Reagan, you grew up here in the Dallas Fort

Worth area, not too far from where I'm sitting now.

I've actually had the privilege of knowing your

dad through church for many, many years, man.

What was growing up like for you?

Yeah, man.

Though we were in Dallas, moved quite a bit and

had a little bit of a different story than Elle

as far as, like, the continuity of place.

And people started in grand Prairie, then Irving,

and then finally ended up in Capel.

And along that journey, I think,

changed schools about six different times.

So I think, as a kid, that allowed for some

quick learning on what it looks like to reset and

figure out how to make relationships wherever you go.

It also probably created some internal questions

around, well, what is home, really?

All that said, I look back on childhood,

and it was a lot of riding on

bikes and exploring the woods around our house.

And I was big into my imagination.

And I think from an early age,

my identity was as an artist.

And so I loved Batman, and I

loved drawing Batman, then I loved drawing.

And then I quickly got into theater when

I realized that sports might not be my

thing and loved theater and speech and debate

and those kinds of activities all through childhood.

I have two younger brothers, were

split apart by five years.

So I'm 38, so 33 old brother

and then a 28 year old brother.

And man, for all intents and purposes,

childhood was a really special time.

And when I think back to

young Reagan, makes my heart happy.

Yeah, man.

You talked about moving.

I moved twice, once at age 13,

and then again at age 16.

And I don't know about you, but moving is

hard, but those were really, really formative years, and

it was a really difficult time to move, especially

after I had kind of rebuilt my friend group.

And now, all of a sudden, it's time

to uproot again and do it all again.

But at the same time, I think it prepared

me for a lot of things in life.

Having to put myself out there and make new connections,

does that resonate for you at all, or was it

just kind of like a fleeting thing and you just

kind of got through it and moved on?

It resonates a lot.

Scott, along the lines of what you said,

the ability to create new connections and understand

how to kind of read the social dynamic

around you and figure out where you fit.

And then I think now that I look back on

it with some hindsight, it allows for me to have

a little bit more clarity when it comes to transitions

because I tend to buck up against big life transitions

and believe that they're going to be a real interruption.

But you have all these data points from

growing up, where you say, on the other

side of that transition, good things happened.

And so there's some nice learnings that you're

able to pull forward from that respect. Trey, it's hard.

It really stinks when you're in it, but looking

back with some maturity and other life experience, I

think you learn to look at it positively.

So after high school, you went to Texas

State down in San Marcos, is that right? Yeah. Yeah.

I was going to go to SMU and do theater because I

was a theater guy and I had a pathway to SMU, but

I was in love with my high school girlfriend, and she was

going to go down to Texas State and be a bobcat.

So I threw that dream away and went to

Texas State and had a really hard freshman year

because she cheated on me with a ta. Oh, wow.

In one of her classes. Yeah. Scandalous. Wow. Okay.

But after that recovery, Texas State ended up being a

blast, and I loved it and got super involved, and

I'm going down to a football game on Thursday, tomorrow.

I remember little bits and pieces.

You were really involved. Yeah.

My senior year, I was student body president

there, and, man, that is one of the

core life experiences that continues to pay dividends.

We actually, that year, got to cobble

all of the different stakeholders together.

Everybody at that time was finally ready to move

our football team up to division one a.

And so we raised the student service

fees and had a referendum and got

alumni based together to give some money.

And so that was a really big year and a really fun

thing to look back on that we got to do that year.

I bet, man.

I went to school at Texas A and

M and had friends that were student body

presidents and other big positions on campus.

I mean, that's a huge time commitment.

And how did you juggle the class and the responsibilities

of being student body president, I never, ever thought that

I would know what it was like to be an

athlete, except for this one moment where I feel like

the student body president role allowed me what I can

only imagine college athletes get, which is a little bit

of grace from all your professors.

And so, thankfully, that year, you had to

have a lot of conversations with professors up

front about the demands of the role.

And there's a lot of absences because you're going

to the Capitol to testify for stuff, and you're

going to other campuses, and you've got to be

at events, and there's a really great tutoring center

that you could go to and get support.

So it was a lot to manage.

Thankfully, man, it was a big to do.

I mean, I had an assistant as a 21 year

old to help with stuff, and, I mean, it was

a really cool thing that I certainly wouldn't have been

able to navigate if I was just trying to manage

school and being student body president.

So there's an assistant, then you.

We had budget to hire a chief of staff.

We had budget to hire somebody

to take care of press stuff.

It was a cool deal, man. What.

What a great way to get some

life experience as a 21 year old.

Now, I got to believe that on the

flip side, once you got out of school,

it's like, hey, where'd my assistant go?

And where's my chief of staff?

So what was your first professional

experience like, right out of college?

What did you go do?

I definitely would tell people who would

become student body president after me.

It's the cruelest thing in the world to happen

to you, because at 21 years old, you get

to be in rooms with people who have spent

30 years trying to get into that room.

And then you graduate, and you're back at

the low end of the feeding line.

I majored in English and with a focus on

creative writing and poetry, and I graduated in 2008.

In a recession.

The only thing I had to make me a

potential candidate for jobs was the student body president

thing, because no one wanted to hire a poet.

And thankfully, I actually, there was a business owner

who we knew through Irving Bible Church who had

a nurse staffing firm and Koppel, Texas.

And they hired me to come in and do business

development for them and help them figure out how to

build more relationships and increase their marketing efforts.

So I got to jump into kind of a big boy job

doing a lot of cold call sales in the Dallas area.

That, in hindsight, I look back on it and I

think, man, I was way out over my skis.

Now I've had to do very, very little cold

calling in my career, but the little bit that

I have done, I hated every second of it.

Are you one of those people that

actually gets a high off of that?

I know those people exist.

It is the worst thing I can imagine doing.

Man, this employer was so kind.

They sent me to conferences and they

paid for me to get coaching.

But at the end of the day, you're having

to walk into hospitals with physicians that are already

busy and convince them that they need your nurses

that you're trying to rent out.

And so I, man, I made that nine months, and

they were so amazing to give me that opportunity.

And then I saw another opportunity that felt a

little bit closer to home and I jumped ship.

And what was that?

Have you ever heard of Teach for America?

Yeah, yeah, yeah.

So I had some colleagues that were joining

the Teach for America Corps, and I thought,

man, that would be a real adventure.

That's a two year program.

Yes, sir, two year program.

They send recent college graduates to low income

school districts who are short on teachers.

And they're thesis is, if we can send people

who demonstrated high potential in college, whether or not

they went to school for teaching, we can get

them certified over the summer to teach, and their

ambition will carry out their education camp.

And where did you get sent?

Well, Scott, I loved the movie Freedom writers

diaries, and I thought I could go and

be some cool teacher in the inner city.

And so I said, I want to go

teach English in Chicago, New York, Washington, DC.

So I preferenced all those places.

And then they call me and they say,

hey, we had a really big application pool.

We have a spot for you, but it's on a

reservation in South Dakota, a town of 400 people.

Not New York.

Not New York.

No, we're close.

Nowhere close.

I remember I was at the shell gas station

on Dett and Tap Road in Coppell, Texas, and

they called me and said that I was pumping

gas, and I just instinctually I needed a change.

And I said, yes, I'll go.

And then three weeks later, I was there. Wow.

So two years in South Dakota, I mean, just anywhere

that teach for America was going to send you was

probably very, very different from your high school experience.

What was that like?

It was quite a culture shock. Yeah.

So not only are you moving all the way across

the country, not only are you moving to a town

of 400 people, you're also moving to a reservation where

I grew up in white suburban Dallas.

And for the first time in my life, I'm

one of the few people that look like me.

But the community could not have been more welcoming.

And I got adopted into a family, and they

were just so glad that we were there.

And there was a small group of teachers in our area

that we became very close and had a really good time.

I ended up teaching 10th grade English, and I

got to tap back into some of my theater

roots and became the theater director and got to

direct the one act plays there.

That's awesome.

That is awesome.

Did you ever go back up there?

When we were there as teachers, we formed

a band because there's nothing to do.

And we knew that there were 38 teachers in the

region who had nothing to do on the weekends.

So we had a standing show at this 1

bar, and we ended up playing 30 something shows

over the course of two years in Nebraska, Wyoming,

and South Dakota and had an absolute blast.

So after we finished, we had a

reunion show a year or so afterward.

But, man, I don't know.

Six of the guys that I served with or were at

our wedding two years ago, and we're all still very close,

as you can imagine, going through an event like that, a

period like that together, it brings you close.

What do you play?

Or are you a singer?

I played bass.

I knew a little bit of guitar.

And they said, you know, the instrument that he

could play, that he could do the least amount

of damage to our sound would be the bass.

And so there you go.

That's kind of chugged along. That's awesome.

Well, sold out crowds and everything.

That's fantastic.

Let's shift over to Ellie for a minute.

We'll come back and kind of talk

through the other steps in your career.

But, Ellie, you wind up in

Dallas after going to Ole Miss.

What kind of work were you doing here?

Great question.

So I had actually, I knew I wanted to be a nurse.

Majored in psychology, prepped, took

all the nursing prerequisites.

I actually thought I would go

get my nursing degree in undergrad.

But when I was at Ole Miss, you couldn't really

stay on campus in Oxford and get a nursing degree.

And I fell just way too in love with Oxford to leave.

And I remember walking across my dormouse freshman year

parking lot about halfway through first semester thinking, I

don't ever want to leave this place.

So majored in psychology, and I got in TCU nursing.

So move.

And right before I went out there for orientation, I

presented to my father my financial plan for how I

was going to pay for this TCU nursing school.

And TCU's not a cheap school.

No, no, Scott, it's a very expensive school.

No, Scott, it is not.

And I had my folder prepped to have this conversation,

and my sweet dad, who cares so much, basically just

said, I don't think this is a good idea.

And so that doubt that descended on me caused

me ultimately to withdraw my spot in the class.

And I said, okay, well, if I move to Texas,

I can get the Texas nursing prereqs, and then I

can go to a public institution after I've gained residency.

That'll be much cheaper.

In the meantime, I'll work as

a nurse tech in hospital systems.

So I worked at Texas Scottish, right?

Which I absolutely loved.

And then I ended up working at

Texas children's in the pediatric cardiac ICU.

And ultimately, my college boyfriend and I broke up.

I said, I gotta get out of here.

I applied at Belmont nursing in

Nashville, which, thankfully had rolling admission.

I find out in, like, six weeks.

I get in and I move back to Nashville,

go to nursing school in a second degree program.

Takes about 16 months to get that.

Also not cheap.

But I just knew I was lucky enough for

my parents to pay for those four years.

They said, that's all you get.

If you're doing any education

beyond that, that's on you.

And so took that education, that new

degree, moved to Charleston, South Carolina.

And when I moved there and had just graduated from

nursing school, I realized how much debt I had that

I was probably going to need a little bit of

supplemental income in order to make ends meet.

And so my mother, at the time, my parents

had moved to North Carolina, and she had this

fresh greenery, fresh wreaths, and garlands business.

My whole childhood, from, like, about age ten

on, she had started gracious garlands, which was

started by a friend saying, hey, Vicki, I

actually think you could sell this beautiful greenery

that you bring back every Thanksgiving to decorate

your house to your friends and neighbors.

So I created her a flyer on word because

she didn't know how to use the computer.

Made a clip art border with

those clip art Christmas trees.

You know the squiggly one?

I've got a mental picture of this. Yep.

So we printed it out, and she came

up with the name gracious garlands, and we

stuck flyers in everyone's mailbox in our neighborhood.

And that was almost 30 years ago.

And that began gracious garlands.

Well, fast forward 20 years, and she's tired.

She doesn't really want to do this anymore.

It's still just a holiday business.

She is still, almost ten years ago, mailing.

People order forms and they are mailing

them back with their credit card number.

No kidding me.

I'm not kidding you.

And it is still like, we have not innovated.

We have not innovated.

We have moved from checks to, like, credit

card machine that you can write, you type

in the number and run things anyway.

That's as innovative as we've gotten.

And she just said, you know, I

think I'm ready to call it quits.

She still likes to debate whether or not I slid in

there in a weak moment and took over the business when

she was just really not ready to let it go.

But I said, you know what?

I've been running this business for a very long time.

You know how it works.

You're the creative, I've been the

business mind in all of this.

I can do this.

I've been helping you decorate homes and mailboxes.

I know all these products so well.

So what if I just take it over? That'll be great.

It'd be a great way for me to make some extra income.

I immediately get on, square up and create

a square marketplace to put everything online and

start collecting orders and kind of slid in

there and took over her business.

What year is this?

Roughly what year?

This is 2014.

It's ten years ago.

And you're nursing full time and

now you've taken this on? Yes.

And you already mentioned, like, it's seasonal, so I imagine

most of the year, like, not a whole lot.

But, golly, when you get into that Thanksgiving

Christmas time period and you're working full time,

like, how did you manage all of that? Scott?

I do not know.

And then once I left the bedside, I ended

up working in the startup space for a medical

legal startup company and helped to grow that company.

And so there was a time in

gracious Garland's existence where we were running

a full fledged holiday operation in Nashville,

a full fledged holiday operation in Austin.

I was flying back and forth between the two cities.

We were decorating over 40 homes and

businesses between two cities, running a pop

up, Reagan's, delivering Christmas trees in Austin.

I have a team of people delivering and

installing Christmas trees in people's homes in Nashville.

While I'm, like, trying to keep my team

of 30 medical professionals that I managed afloat.

And it's no wonder I've struggled with a

little bit of health issues in the recent

years from that time of just extreme stress.

And I think, to this day, how on earth did I do that?

And I don't know.

Sure will and determination, a little bit of, I must

be some bit crazy to be able to withstand that.

But I also have a loving husband who stepped in

from, you know, the very beginning of us dating to

help me pull some of these things off.

So real quick, you said you were

delivering Christmas trees, like an actual tree. Yeah.

You started, though, just doing like

table decorations and things like that. Is that right?

So actually, we did trees from the very

beginning so people would order their fresh wreaths

and garlands and Christmas trees from us.

And we could, if you ordered a Christmas

tree, you could order Christmas tree installation.

And so we had our install team that

would take your Christmas tree to your house.

We would give it a fresh cut, blow it out,

shake it out, get all the dead needles off of

it, put your tree stand on, take it into the

house, get it just right, water the tree and leave.

I mean, like white glove Christmas tree service, everything

but putting the ornaments on, everything but that.

And we, of course, did that for certain clients.

But 95% of our customers that ordered

Christmas trees ordered that installation service.

We do not, we sadly don't do Christmas trees anymore.

But yes, we were mostly, we've always mostly been.

Reagan's not sad.

Well, I kind of like it.

He kind of likes the torture like I do.

You know, we're kind of crazy, you

know, Scott, like, you're kind of crazy.

I kind of like it sometimes.

Okay. Wow. Yeah.

So a few years ago, I had to

get honest with myself about what was sustainable

and I really had like three or four

businesses under one in the gracious garlands world.

And so I decided to streamline things and basically

get rid of Christmas trees, get rid of decorating.

We partner with designers that will refer

people to that use our products.

But I don't do any more in home

decorating and I solely focus on our products.

And now we have no in person location.

It's all drop shipping.

Everything is made fresh on the farm that makes

our products and then they ship with two day

shipping and show up at your doorstep.

And I just had to really be honest, like, what brings

me the most joy and what is best for the business

and that is the most profitable arm of the business.

And I had another business that I wanted to grow,

so I had to make some space in my life.

So let's go ahead and jump into that.

Your other business, like, couldn't be

more different than home decor.

And im going to make a major assumption here,

but you said you studied psychology in college.

Is that what kind of pulled

you into this Enneagram world. Absolutely.

I mean, when I woke up one day finding myself

having built this Enneagram coaching and consulting business, I realized,

oh, all my roads have collided into one now. So.

Always been so curious about people my whole life.

And real quick, I think a lot of people know

what Enneagram is, but there's probably plenty that don't.

Can you just kind of explain that for a minute? Yes.

So the enneagram is a fantastic tool that

we can use to raise our self awareness.

And the Enneagram symbol itself looks

like a map or a compass.

And there's nine points and there's nine numbers.

Those nine points we use to represent nine core

different personalities that we see within human behavior.

They're really equivalent to our ego

that we develop in early childhood.

And hopefully you're listening to this podcast.

If you've never heard about the enneagram, then lucky

you, you are now introduced to this tool.

Hopefully we get to a place in our journey where

we are introduced to this idea that our ego, our

personality, is not all of who we are.

It's a mask we learn to wear to cope

and survive in the world based on the messages

we received and also kind of our internal makeup.

But the work through the enneagram is to

identify your point on the map, which is

equivalent to that personality, that mask.

And our work is to begin to move around

the map and recover our wholeness that we lost

touch with by reclaiming each point along the map.

And so it's a tool for growth and evolution.

So to kind of tie into my journey as a

nurse, I went into nursing to help people heal.

I should always have identified as a healer.

And I wanted to meet people on that healing

journey, bring more of that energy into the world.

And I realized, oh, our healthcare

system does not do that.

It is not built at this point to help people heal.

It actually, it's kind of built

to keep us stuck and sick.

And so I got really burnt out in our system so quickly.

And so I jump ship.

I left the clinical world knowing that I had such

a passion for helping people heal, but I needed to

go kind of on my own journey and figure out

what's going to be the modality I can use to

really help people on this journey.

I use the Enneagram to help people really live

a holistically healthier life by first identifying their personality,

which helps us to really highlight the way we

self sabotage in all areas of our life.

So from a health perspective, we're getting healthier

our relationship to our self is improving.

Our physical health is improving, our relationships

are improving, our professional life is improving,

and even our spiritual life really, really

deepens through using this tool, the enneagram.

So when I found out about it when I was

at this startup, started using it in my own personal

life and with my team, and I just thought, oh,

my gosh, I'm obsessed with this tool.

Can I teach this to people for money?

Can I make a living off of this?

And sure enough, I found out, yeah, I

could go get certified and did that four

years ago and started this coaching business.

And I coach people one on one, and I work

with teams and integrate the Enneagram into their team culture.

Do you remember that moment when you thought,

could I make a living doing this?

Oh, so vividly.

I was sitting on our couch listening to.

Are you familiar with Richard Rohrdez? I'm not.

He is, like, my spiritual guide, and

he runs the center for Action and

Contemplation in Albuquerque, New Mexico.

And they have a couple of amazing podcasts out there.

Well, they had one on the

Enneagram called Enneagram map makers.

And I happen to be sitting it's peak pandemic.

I'm on my couch listening to this podcast, and

I got this, like, very intuition kind of voice

that just kind of gut punches me.

Hey, you could teach people this.

You want everyone on the planet

to know about this tool?

Go do a quick Google search and

see if you can get certified.

Like, how do you do that?

And it was just such a clear calling in

that moment and spent about four months in discernment

researching, talking to different programs, saving up, and decided

to leave that startup and pursue this avenue.

And you and Reagan were dating at that point.

We were dating 2020. Yeah.

One of the questions that we ask a lot is for

most of our guests who were married at the time when

they decided they were going to go do this thing.

What was your spouse's reaction when you

said, I want to go do this?

A little bit different if you guys aren't married.

But, like, did you guys talk about

that before you made that jump?

Or did you just kind of say,

hey, this is what I'm doing?

Oh, for sure.

So Reagan and I, we've been

together for seven years, babe.

Seven and a half.

And we moved in together in 2019.

So our lives were very fused by 2020, and

we were working to figure all of that out.

And from a very, very, very early on in our

relationship, a few months in, it was very evident.

We are a team.

We are helping each other through these

big life decisions, supporting each other.

We've always been entrepreneurs as we've been together.

But he, of course, had some reservations.

He said, whoa, whoa, whoa, whoa, whoa.

We've been talking about simplifying your

life and divesting gracious garlands.

Now you want to add something else?

And this was one of those moments.

The discernment period was probably so long because I have

a husband who needs to really sit with change and.

And be convinced of things.

But I will say this.

There are a few times in our journey where I've just.

I've.

It's been very clear this is the path.

I feel an unwavering certainty about it and

peace about it, and it's just kind of

figuring out, giving it space and time to

breathe, not hastily jumping into something.

And that was one of those times.

Four months did feel like a long time to

wait to make that decision, but it was the

right thing, and I really value that.

He is more risk averse than I am.

And so we balance each other out in that way big time.

A quick just aside.

When I graduated from college, it seemed like every

company I applied to, the first step was you

had to go through some personality assessment, and I

couldn't even tell you how many of those things

I took my last semester.

I'd go to the career fair, I'd talk to all these

people at the table, and first thing, boom, go do this.

And at the time, I remember thinking,

this is a bunch of baloneye.

I was skeptical about it and didnt

see a lot of value in it.

The company that I went to work for right

out of college, they were big on disc, and

so everybody had their disk profile on their desk.

And again, I was kind of like, yeah, whatever.

About four or five years ago that my company,

we actually decided to implement something called culture index.

And went into that a little skeptical.

But the more I dug into it, the better it

helped me understand myself, the more convinced I was.

And for a variety of reasons over the last

several years, I've ended up doing working geniuses, obviously,

culture index, Myers Briggs, a whole bunch of others.

And then somebody said, hey, I

want you to do Enneagram.

And with each of these, it's really created

more and more self awareness and helped me

to realize, oh, I do this thing.

And that may not always go over too

well with the people that I'm interacting with.

And with Enneagram in particular, it helped me actually understand

why I do some of the things that I do.

And that was this huge, huge revelation.

So for anybody who's listening who was like me, that

thought this was a bunch of baloney, I would strongly

encourage you, like give it another chance and really dig

in because I guarantee you will learn things about yourself

that you didn't realize were there.

Absolutely.

I have people say all the time

to me, so is it like astrology?

And I'm like, no, no, no, I'm fairy. I'm a head type.

And so data and the science behind this

tool to validate is really important to me.

And so I will then say, well, no, it's

really just, it's a metaphor for personality development.

And we all go through this.

And I'll tell you the neuroscience

that backs up the Enneagram tool.

And there's so much more to it than, oh,

it's just another personality test, a party trick.

So I'm so glad that you said that.

And, you know, I think that there are so

many different ways we can highlight this truth.

And a tool to make you more curious about

yourself and others can do nothing but good.

Absolutely nothing.

Wholeheartedly agree. All right.

You said you went through a four month discernment

period to really kind of sort this out.

And Reagan, I imagine you were getting comfortable

with it along that time as well.

You said you went through

some classes, you got certified.

What was your thought around?

Like, how am I actually going to monetize this?

Did you have a business plan?

Like, heres how Im going to find that first customer.

Heres how Im going to charge for it?

What was that process like?

Yeah, I am really grateful that I had the experience

of gracious garlands as a foundation before launching a new

business because I have made so many mistakes.

I have pivoted 1000 times every year.

It's a new business basically from gracious garlands.

And so even though GG is a product based business,

there was a lot that I foundationally understood about how

to run a business, anywhere from marketing to a financial

model to how do I set up a business account?

How do I build a website, a Google workspace?

How do I get an email that isyondyourtype.com or, you

know, all these things that we forget as entrepreneurs.

When we started out, we had to figure out, you know,

so all of those things I didn't have to worry about.

I knew immediately I could just

go, I could build this business.

I knew how to do all of that.

The thing I had a big question mark

about was when can I start charging?

And there was a little bit of imposter

syndrome, you know, as a service based business,

like, oh, am I good enough?

When can I start taking people's

money for giving them my time?

And I had a couple people in my life really push me

and encourage me to do that as soon as possible, to feel

like, hey, let's look at the history of your career.

And while you haven't been a certified Enneagram

coach for very long, you majored in psychology.

You worked in the hospital system for seven years.

You know how to talk to

people and ask intentional questions.

So what I ended up doing

was built a test coaching program.

I had four people that I said,

hey, I'm looking for some beta testers.

I did four for free, ran them through it,

got their feedback, and then I started charging.

And I ran that same program for a year before.

Then I said, okay, now I'm going to

come back to the drawing board and figure

out what needs to change from this.

And then as far as corporate clients, I think

I probably did one or two for a discount.

But I had the built in coach.

And Reagan, who is a facilitator and

a speaker, he does this for a

living, working with companies and running workshops.

And I'd been.

We've had a trial period when

I worked for him formally.

That didn't go so well.

About every couple of months, I think, do

you need me to step back in?

He's like, no, that went horribly.

Let's not do that ever again.

So he was there to help me understand kind

of benchmark where I need to start, pricing wise.

And so that was really valuable.

And so, you know, you just kind of boldly

have to say, this is what I'm worth.

There's a little bit of fake it till you make it,

and you know so much more than you think you do.

And it just is getting in there, doing it.

This was probably 1314 years ago.

I just gone through some training for some technical

stuff, and I was getting ready to go into

my first meeting, pitching something to a prospect.

This was before I started my business.

I was a couple companies back, and I remember flying to

Boston and getting on the rental car with my boss.

And we get there, and we're in the parking lot, and

he can tell I'm nervous, and I'm really, really nervous.

And he said to me, you know more than they

do, no matter what, you know more than they do.

And when he said that, like, that was

a light bulb moment for me, and it

gave me the confidence to go in there.

And when we came out and this, he was

not someone that gave a lot of praise.

He said you rocked that.

And just that, just that little shift.

You know more than they, you may not know

it all, but you know more than they do.

You know more than you think. You know.

I think that more and more people need to

hear that, frankly, just whether an entrepreneur or not,

people need to hear that and have that extra

little bit of courage in their careers. Totally.

I think one little note on that.

I also think the Enneagram helps

people to understand what's your tendency?

Because I have plenty of people that went through

my same program that still haven't launched a business,

and they are not social sevens like me.

Sevens are a little bit neurotic in that oftentimes

we think we're experts before we're experts, but that

helps us to be entrepreneurs because we're willing to

go out there and kind of look like a

fool, maybe more than others.

And then there are certain personality types that

really are motivated by security and they're worried

about doing it or approval, so they're worried

about doing it or control.

And so they're the, they're worried about doing.

If we can get to the why and what is

holding you back, then we can actually propel you forward.

And in the same way, it was really important

for me as a seven to know my tendency

is to press the gas a little too preemptively.

And so what do I need to do

to make sure I really am prepared?

And I'm building one branch of this

business at a time, because with gracious

garlands, I had a million branches.

So for the past several years, it's mostly

been focused on building that one on one.

And then it was, all right, let's

really lean into the corporate work.

And that was really important for my

personality to develop that expertise that sometimes

can fall to the wayside with us.

You said something a second ago I

think was really enlightening and important.

You said there were people that you went

through the certification program with that still years

later, have not actually launched a business.

And before you said that, I heard you talking about

you actually had to come up with your own program.

And here's what this is going to function like.

So when you went through your classes, it wasn't like,

hey, we're going to train you up on this and

here's how you build a business around it.

Here's your enneagram consulting practice in a box.

Go do.

You had to figure out all the

nuts and bolts from scratch, right?

And actually, Scott, that's a potential business that I have

is creating a program for, a funnel program for coming

out of these Enneagram certifications and say, okay, now I've

got, let me hand you a business model and run

with it, because I've done it. I have it.

I could do it.

My work is to stay focused on what's most important.

And so I haven't done that yet,

but there's a huge need for it.

And I'm just really fortunate

that I am entrepreneurial minded.

That stuff doesn't scare me, and I had done it

before, so the barrier to entry was very little.

Reagan, let's jump back to you.

Take us from South Dakota to Austin, Texas.

What were the things that happened in between there?

Absolutely love South Dakota.

It was so hard to leave because as we get

older, rarely in our lives do we have these containers

of time that you're doing with the same group of

people, like a college or like a grad school.

And so TFA was that in South

Dakota, many of my colleagues were staying

for a third year beyond their requirement.

But at that time, like I said, this Texas

state student body president thing continues to pay dividends.

I had a mentor from Texas State who was

an alumni who was really invested in young leaders

at Texas State who had defected from Deloitte with

another guy and started a management consulting firm.

And they were going gangbusters.

And he also had a nonprofit that he

was trying to get off the ground that

was a student leadership curriculum that he wanted

to get into college campuses, particularly Texas State.

So step one was, and this is the importance of

mentorship, and we could take that tangent if you want,

but my goodness, step one was, I had a relationship

with a person who said, I believe in you.

I don't know what position you're going to

play yet, but let's do something together.

And so spent about a year working with him, building

this leadership curriculum that at first, and this is a

great entrepreneurial lesson I've learned over the years, that at

first, no one wanted to buy, and so we just

started doing it for free to demonstrate its value.

So no universities wanted to make our

class A curriculum on their campus.

So we would find a student leader, and

students who were enrolled at the university could

rent university space us, as outsiders couldn't.

So we would find a student leader, convince them to rent a

classroom for us, and we would go teach this 14 week class

for free for any student who wanted to do it.

And next thing we know, two,

three semesters later, we're oversubscribed.

We've got like 40 students and 40 students on

the waiting list wanting to do this program.

And so two or three years into that, we have

a program that Texas State is offering for credit.

Trinity University down in San

Antonio is offering for credit.

Angelo State University out in San

Angelo is offering for credit.

And me and my boss would go teach a

night class on Thursday night in San Antonio, drive

to San Angelo, teach an 08:00 a.m.

class Friday, drive to San Marcos, teach a 01:00 p.m.

class.

And we did that for semesters, and we had the most fun.

So this is where this, like, teaching

facilitation stuff continues to be a theme.

This leadership curriculum, self awareness,

experience making becomes a theme.

But about that time, he says to me, this is all fun,

and I still want you to do all of this nonprofit stuff,

but I'm tired of paying you from the nonprofit budget.

So we need to make you add some value

to this consulting firm where we have more money.

So then I get a completely different experience in

education, moving into the management consulting world, and I

get a spot on the marketing team and I

get to make up my position.

So I decide I want my position to be

raconteur, the chief storyteller of this consulting firm.

And I wanted to make movies and videos to

tell the stories of the work we were doing.

So he lets me go buy a bunch of camera equipment.

I go to Ut and get an intern from

the radio, television and film department and spend five

years working for this consulting firm, flying around our

clients and filming kind of talking head interviews about

the changes that we're helping them create.

And never thought I'd find myself

in the business world there.

But I got an unofficial MBA from getting to shadow

that man and getting to work in that consulting firm.

And that was just a really, really fun season.

You said the m word and it comes up a lot.

Mentor, and I just love that.

And it seems like that kind of

came about serendipitously, or it was not

like you went out intentionally seeking that.

It doesn't sound like it just kind of happened.

And it's amazing what happens when

quality people find other quality people.

When he came to you and said, hey, we got to figure

out how to pay for you, did that catch you off guard?

Was that well received?

Like, how did that hit you?

He is a dynamic Richard Branson type.

Like burn the candle at both ends.

And so he always pushed it.

I remember the first day on the job, he told

me, I'm really excited you're here, and I'm going to

put things on your plate until you squeal.

He valued running fast, and so I was certainly

not surprised whenever he made a decision like that

and said, hey, we need to move you over

here, and you still need to do the other

stuff, but it's all going to be really fun.

And he was so good at making everybody excited

to work really hard and run really fast.

Was that exhilarating when he basically said, you get

to create your own position, you come to him

and say, hey, I want to buy all this

stuff, and here's what I'm going to go do.

Was that exciting?

Was that scary?

A little bit of both.

Initially it was super exciting.

And again, what a gift to have someone who sees promise

in a younger person and says, go crazy, go for it.

The imposter syndrome started to set in when I

realized that I knew nothing about filming anything.

And this intern that I was paying $13

an hour could really take my job.

And actually, he ended up taking my job

when I left the consulting firm, and he

was way more qualified than I was.

But on the front end, it was really exciting.

Over the course of those five years, as I was

going around telling the stories of the people that we

were working with and doing this video stuff, it became

evident, though, that, you know, Scott, one of the big

lessons over my career has been that there's a big

difference between being interested in something and actually wanting to

execute on the activities required of that thing.

And when I talk to younger people, that's one

of the most important things that I tell them,

is that interest does not equal promise.

And so I was interested in video storytelling, but when you

look at what it actually takes on a day to day

basis, that kind of technical stuff ended up draining me.

And so there came a time where it was

time for me to jump ship from that role.

Thats something that I think is really important.

And I think its okay that some things are there

for a season in your life, and something that you

start off with a ton of excitement and passion for.

You may not have that forever, and it's okay.

And you can take and build on that and

use that to go do something else and learn.

And I think that's probably a big part of your story.

Where did that take you after

you left that management consulting role?

So I've always been taught to just pay attention

to the themes, pay attention to what's bubbling up.

And so at that time, when I knew that it was

about time for me to move on to the next thing,

I kind of looked backward and realized that there were some

themes around speaking in front of people, facilitating an experience for

people, and creative writing of some sort.

And in addition to all that work with the class

we were teaching and the consulting stuff, of course, that

gentleman that I worked for also found a role for

me to plan and facilitate our annual firm gathering.

And I found myself in a role

of, like, facilitating meetings and retreats often.

And so I knew I needed some time to think about,

what does it look like to be like a speaker facilitator?

At that time, I don't even think facilitator was

a job title people were talking about yet.

And thankfully, a dear friend of ours here in

Austin had launched a startup that was focused on

helping people with some college but no degree.

So they had to drop out of college for one

reason or another before they finalized their degree, helping them

finish college, because what they found was in just in

the Austin area, 80% of the people with some college

and no degree will never finish that degree.

So he figured out a way to pair them with online

schools, and I jumped on to help him build a coaching

program to get those people to and through graduation.

At that time, with the consulting firm,

I was traveling all over the place.

But at that time, I'm here in Austin.

I'm in an office every day, and I'm starting to

go to meetups and going to south by southwest and

getting involved in this, like, facilitation art scene.

And two buddies of mine and I, we start

hosting these, like, salon dinners at my house, where

once a month, we'll have a dinner where we

facilitate an intentional discussion around one topic.

And I turned my birthday into an experience where we

would carve pumpkins and use pumpkins to tell stories.

And then those two friends and I,

we started just throwing our hat in

the ring to facilitate experiences for companies.

So this is the classic, you

know, just like, iterate on it.

So we built a few different prototypes

of workshops we thought would benefit companies.

And I'll never forget, there is

an association for building managers called

the Building Owners and Managers Association. Bomade.

And a friend of mine was on that committee, and

they were going to pay us $500 to come and

teach a 60 minutes lunch and learn about effective communication.

And the three of us walked out of

there, and we had a $500 check.

And there's the moment that's real money.

And so after working with my buddy for

a year at that nonprofit, the three of

us then started a little consulting firm called

Assemble as in to assemble people together.

And so that was the very beginning of

me being on my own, trying to figure

out how to speak in front of people

and facilitate experiences that guide people toward growth.

We had a blast doing that for about a year.

Then one of the guys got into his dream PhD program,

and another, the guy, they got pregnant with their first kid,

and he needed to go make some guaranteed money.

So then it ends up just me, but

I still want to continue the work.

And so what I do today as a speaker and a

facilitator and a writer came from that assembled group of guys,

and then I just kind of continued that work.

I still called it assemble for another year or so.

And then I just dropped that.

And I became Reagan, the guy who talks and facilitates.

I love that.

Reagan, the guy that talks and facilitates.

All right, we were talking a minute ago about Ellie

having to kind of put this program together and figure

out how to price it and so forth.

You had that first client that paid you

$500 to come and talk over lunch.

Walk me through the what was the thought

process there of $500 split in three ways?

That didnt go super far.

So how did you take and build on that, and

how did you figure out how to price the next

thing and the next thing and the next thing?

Im in this season right now, Scott.

The thing that I avoid the most, that is always

the most important thing, is to go out and to

socialize my challenges with people who've been there before and

to try and find myself a new mentor.

It took me a while of doing a bunch of

free stuff and charging $500 because that's all I'd ever

charged to finally go to the National Speakers association in

Austin and ask one of the old fogies over there

to take me to coffee and tell me.

It took me a while to realize that there is an

alumni from Texas state who is a public speaker who had

written three books, and if I drove down to visit him

in San Antonio, he'd probably buy me coffee.

And, man, it took me almost a year of

taking $500 checks until I finally did what was

good for me and realized that people are happy

to tell you the road that they had traveled.

So I remember after those conversations started to happen, and

I was telling these folks what I was charging overnight,

my 1 hour session went up to $1,500.

And then I started asking one guy, particularly anytime

I had a session in Austin, id ask him

to come watch me and critique me afterward.

And that had been invaluable.

And then finally, yeah, I dont go to

the National Speakers association stuff as much, but,

man, I cant advocate enough for an industry

specific mastermind kind of a thing that helps

you understand what the going rate is because

otherwise youre probably going to undercut yourself.

Pricing, I dont care what business youre in.

Pricing is one of the hardest things about

business, especially when youre carving a new path.

You dont want to charge too much that you

lose the business, but you also dont want to

leave money on the table from client to client.

The line for that could be different.

And it takes a lot of courage to plant the flag and say,

no, this is it, and this is what we're going to do.

And again, like, you had to have people outside of

you telling you this for you to actually take action.

And so, so important to have

other people speaking into it.

You said something else there, though,

about people speaking into things.

You very intentionally opened yourself up to critique.

You told this person, I want you to come and listen.

I mean, when you're doing something creative, when

you're putting yourself out there like that, that'd

be hard for a lot of people.

Was it hard to hear that feedback or was it easy?

What were those first few conversations

like after him hearing you speak?

I have some big wounds from this guy.

He took me to coffee and he ripped it to shreds.

And I still sometimes am afraid when I see him

around because I'll see him at events throughout Austin.

But to bring in the enneagram,

I know he's an enneagram eight.

And through the work of understanding yourself with

Enneagram, how beneficial that is, it's also so

valuable to help you understand others.

And I know his motivation is

to help people reach their potential.

That's what aides want.

But sometimes they get angry that people aren't there

yet, and so they just want to shake them.

And so now I can interact with him and know that he's

going to be gruff, but there's a teddy bear under there.

But I'll tell you what, man, that was really hard.

There was another time that I was at a national

speakers association meeting, and they allowed you an opportunity to

get up and try out a part of a speech.

And I tried out a part of a speech, and there's

this old british woman there, and she ripped me to shreds

in front of a room full of, like 30 people.

And, dude, that's no fun.

That's no fun at all.

And yet, I will never forget any of those lessons.

And I've never made any of those mistakes again.

So it made you better. It did, man.

And in the speaking world, in the

facilitation world, if you're not doing something

out loud, it doesn't count as practice.

So many people in this business, they want to ride it

and they want to rehearse it in their head, and then

they want to show up and try it cold.

And you're not going to serve your clients

well if you do it that way.

Jeff, I've been to plenty of conferences over the years

where they brought in all kinds of speakers, and some

of them are great and some of them just aren't.

And even the ones that aren't, like, I feel bad

because they've poured every bit of themselves into it.

I'm like, man, that just didn't hit.

Like, I don't know what to do with this.

Do you feel like you've found your voice and, like,

have you got to the point where, like, you've really

honed your message and you've got, like, a really clear,

a really clear track that's resonating with people?

So I love this quote by Miles Davis.

He says, it took me my whole life to learn

how to play like myself, and I've really resonated with

that on this last seven years of crafting, messaging, and

trying to get it to resonate with people.

I'd say for the first over half of my career,

what I tried to do, let's speak about the things

that I thought people wanted to hear about.

So if you wanted a time management

session, I got your session on productivity.

If you want a session on mentorship, I got it.

If you want a crucial conversation session, I got it.

If you want a session on habits, let's go.

And so people appreciated my energy.

Scott and I wrote handwritten thank you notes afterward,

and it was easy to work with and so

I could get repeat business and referrals.

But one of the cardinal sins that I continue to

learn about as I get further into this professional speaking

world is having too many things that you talk about

to the point where people couldn't say, oh, yeah, that's

the guy that talks about x.

And so the journey over the past two or three years

has been, what does it look like to refine a message

and go deep enough with it so that I know it

intimately, so I can serve my audience excellently and so that

I'm sticky in their memory and they don't just say, oh,

yeah, I don't know what he talks about, but he's good

and I think that the greatest tool to actually find my

voice, to actually learn how to play like myself, was the

really arduous process of trying to write a book and finally

getting that out into the world.

And I'd say that started during COVID and

it took me, you know, almost four years

to get that book into the world.

But now that that's out there, it's like, oh, man.

Thankfully, this really lasers in on the message that

I really want to share with people, Trey.

So just kind of putting the timelines together.

Ellie, at the time, youre coming to Reagan saying, hey,

I think I want to make this career change.

Youre going through a bit of a speaking in writing.

I guess they pair very well together,

but thats a whole new venture.

So youre both going through some change

or something significant at the same time.

Is that a fair statement? Yeah. Yeah.

Yeah, I would definitely say that.

Well, he would say this, too.

I knew he had a book in him and just

desperately wanted him to find out what that was and

write it and put it out into the world.

The first time I saw Reagan speak was a few months

into us dating because he did TEDx here in Austin.

And I thought, wow, this guy is so

charismatic and such an incredibly talented speaker.

It's no wonder he comes from a

line of pastors, lead pastors, you know?

So he's got that pastor vibe

to him that just people are.

He's magnetic and as good, as

fantastic as he is a speaker.

He is a writer, and he always says, you're biased.

You're like, you don't count.

It's like your mom saying, oh, my son's just the best.

I remind him that again, I'm a head type.

I'm not a heart type.

If I didn't think your stuff was good,

I wouldn't tell you that it was good.

That's just not how I operate,

I'll be honest, you know?

And so it was just so, ugh, lovely to watch him

begin that process and just cheer him on the whole way.

Let's talk about the pandemic for just a second.

Reagan, your work is pretty heavily tied

to getting in front of audiences.

What was that like for you?

Obviously gave you some time to sit down and start

writing, but what was going through your mind at that.

At that time, it was really scary, Scott.

I just sold the biggest deal that I ever sold.

It was a series of workshops and trainings for a

credit union that was to be delivered over a year.

It was a five figure deal.

I couldn't believe that I'd sold something like that.

And no joke, we are in the second training session

of what is supposed to be an entire year's worth

of stuff, and we take a break for lunch.

And after lunch, it is in, it's in mid March.

After lunch, the training director calls me into

our office, and she said, honey, I'm sorry,

but we're about to shut everything down.

We're gonna have to cancel this whole thing.

Also, I learned an important lesson at that time

about the language of one's contracts because I had

no safeguards in place on my one page contract.

So I remember going home, thinking dad was going to

pay some bills, man, and wallowing for like, two weeks.

And then, thankfully, I've got this

really resilient and amazing partner.

Not wife yet at the time, but partner in

Ellie, who says, dude, you're going to need to

get ahead of whatever people are doing, and you're

going to need to figure out what's going on.

Everyone's going to zoom.

So, dude, we started looking at the people that were

on the forefront of doing the Zoom stuff, and we

brought in mics, and we had a DSLR camera, and

we had a backdrop, and we had a studio, and

I had all of my workshops on time management and

habits and crucial conversations, and we put them up on

my website and started doing virtual sessions and taking tickets.

Dude, I was taking $9 tickets from people, and

ten people would show up to these things.

That's cheaper than a movie.

Yeah, yeah.

So you were doing these.

And then, thankfully, because Ellie

pushed me to do that.

And we got on that early when all of

the associations that I was already doing in person

work for who had canceled on me realized that

their members still needed professional development.

In the pandemic, they said, oh, dude, Reagan already

figured out how to do the virtual thing.

So, man, thankfully, I was able to

transition a lot of business to virtual

Zoom based trainings during that time.

And that was thanks to some

quick reaction from my wife.

But, dude, it was scary.

Two weeks pondering what was going to happen.

I have so much empathy for you.

On March 11 of 2020, I signed a

lease opening an office in Washington, DC.

We worked there literally one day.

We just hired some people to open up that office.

The only time they ever went

back was to get their stuff.

It was a very, very scary time.

Something Ive said a number of times on

the podcast is theres no one path to

entrepreneurship, and theres all kinds of different ways

that people find themselves in it.

And theres obviously all kinds of

businesses that you can start.

But what youre doing, Reagan, theres not a

whole lot of people that are doing that.

I mean, obviously theyre out there, but there are way

more people that do what I do out there in

the world than there are what you do.

How did you build the business?

Ellie talked about she knew she needed to

get a website and knew about the accounting

side and all that comes with that.

But how did you figure out how to build a business?

A mentor of mine once said, you're kind

of always doing one or two things.

Ideally, you'd know the right timing for them.

You're either building or you're selling.

And for me, anytime someone asks me how do I

get into the speaking or facilitation game, I say, don't

quit your day job and do 100 for free.

And thankfully, being an adjunct professor at all these different

universities, talking about leadership and personal development and then doing

the events for the consulting firm and trainings for the

consulting firm, I got so many reps and that when

I wanted to start going, doing things for free around

town, man, I would sign up to speak at south

by Southwest at the worst time, but I would get

to speak at south by Southwest and put that on

my resume.

And so that was like the real building season.

But then there had to come the selling season.

So how did I build the business, man, I tried so long

to figure out how to do it myself, but it was finally

being willing to open myself up to ask for help.

That changed everything for me, because like you

said, there's not that many people who are

professional speakers or professional facilitators, and those folks

are really interested in helping one another.

A good friend of mine, during the pandemic, in

order to make ends meet, he started mastermind groups

that he would facilitate and he would pair random

entrepreneurs together over an eight week program.

I think I ran through that thing three times.

It was so valuable to knock heads against other people

that were trying to figure out their own businesses, to

learn how to invoice and how to do accounting.

It took me a while to build a website.

Even to this day, I'm not really great on promotion

because such a huge part of the business is referrals.

But it's a quirky business.

You're largely referral based, and the people

who really like you, they can't necessarily

bring you back immediately because they need

to keep fresh faces on the stage.

So I'm trying to figure out right now,

what does another source of revenue look like?

That's not me on a stage or in a room

somewhere and hoping that the book can be part of

that, though it's really hard to sell books.

And I don't know if canned online trainings is the

way to go or I should move into coaching.

But that's been the journey.

Trey 2020, through Ellie's encouragement,

you get the book going.

Walk me through that journey of going from

the idea to actually seeing it published.

I started writing a book about how to live

a more meaningful life, which is great, and who

doesn't want to live a more meaningful life?

But then I.

I put it in front of some people, and some of

the feedback that I got was, this is really good, Reagan.

This is really good.

But, like, what about your wounds?

What about what you've overcome?

How is this speaking to that?

Like, what is the one thing you can say?

So I went back to the drawing board, and,

man, Scott, this is a real theme that's showing

up today that I need to listen to, because

here's what I'm going to tell you, dude.

I need to listen to this.

I went to a group of people, and I didn't do it alone.

So this is still pandemic.

And I find a writing group that's run

under Seth Godin's umbrella called writing in community.

And you pay $250 for a 90 day program where

you're in a cohort and you have to submit pages

every day to your little cohort of people, and you

get on a Zoom call for an hour every morning.

And they helped me refine this book, and that book

came out of there, and I didn't do it alone.

Entrepreneurs are generous people, and the next help

that I needed was I needed an editor.

And that costs some money, dude, because I heard

Ryan Holiday say once, if you think hiring an

expensive editor is expensive, try hiring a cheap one.

So I paid for a good editor, and then I had

to pay for another editor to help me publish it.

So the theme of finishing the book is, I didn't do it

alone, and I found people who are better at the things that

I didn't know how to do, and I was willing to double

down on myself to get the thing out there.

Robert, I love what you said about, if you think

an editor is expensive, try hiring a cheap one.

And I want to go back to your comment earlier

about the contract that you had for this program.

Man, one of the things that I've been

so reluctant to spend money on attorneys over

the years, and, man, that's one thing.

If I could go back and tell myself I would go

back and say, hey, no pause, go spend the time.

Go spend the money with the attorney because thats going

to help you down the road more than you know.

And so there are definitely limits to it.

But as entrepreneurs, weve got to spend money and

weve got to spend in the right places, but

weve got to be willing to spend money on

things that are sometimes hard to spend money on.

Absolutely.

And then the psychological benefits that come

from essentially, like burning the ships. Right.

Like youre double committed, I think, helps.

Without a doubt.

This is really interesting already.

I love the background and I love the stories, but

I think where the story gets much more interesting is

how does this play out at home for y'all, where

there's no steady w two paycheck coming in?

So one of the things, themes I've already

heard over and over is partner, partner, partner.

And there's been a lot of help.

But I guess day to day, what

does that look like for y'all?

Ellie, are you constantly listening in on his

calls and giving him that critique afterward?

And, Reagan, are you helping with

invoicing and things like that?

What does that look like day to day?

I just had this thought and got

a little emotional thinking about it.

We're really lucky how obsessed we are with

one another because we both work from home,

so we're together all day, every day.

And he travels a lot.

I'm starting to travel more.

And so we hate that.

We like being together.

And I think that we're really lucky that that's

our situation, that we'd rather be together than apartheid.

And we are a really good team.

We're actually better when there's, like, a project for us

to be working on and putting our attention towards.

Instead of, if there's not much going on, then,

you know, what happens is your energy starts going

at one another, and that's not the best.

So we do step in and support

each other a lot over the years.

It was Reagan pulling me in after he

built a new talk to go over it.

And it used to be more last minute than it is now.

And it's always, hey, can I get a little bit

of your time and toss some ideas on you and

helping to refine his talks or help him order his

chapters in his books or in his book.

I've always wanted to do that.

And he has always stepped in whenever I've

needed him, whether it be gracious garlands.

I mean, he's been, he's known

as Mister Yuletide in that business.

Many people think he must work in the business daily.

And during the holiday season, he has historically

taken one or two months off of his

work to work for gracious garlands.

Sometimes not out of his own fruition.

He just out of dire need and desperation that I've

put too much on my plate, not planned in advance.

And luckily the holiday time is a slow time

for speakers, so he's able to do that.

So he's been so selfless.

But I do think we just have this unspoken understanding

that we're solopreneurs, but we're kind of co workers.

That's been essential. Totally.

I mean, we kind of got the family empire

and there's, there's three businesses that exist within it

and my websites, I've never done any of that.

Ellie does that.

On the night before my book launched, Ellie's

launching a brand new website for me.

And then there's days during gracious garlands where she's

like, hey, I need to read through all these

new pricing that all these new reads are going

to be, and I need you to copy it

down so we can understand the difference.

And then the room she's sitting in right now

is our front room in our house that fortunately,

by happenstance, has a separate entrance to it, because

when she's in her busy season, she's seeing twelve

or 15 coaching clients a week.

And so they're in and out of that.

And she has a sound machine outside the door.

Scott and me and the dogs have to tiptoe around

all day long while she's in there meeting these clients.

Sometimes I want to take my shirt off and

like, go pick weeds in the front yard.

And she has to be like, put it on.

Put your shirt on.

Don't, don't.

And then I'm upstairs right now.

But she'll sometimes she'll tell me, dude,

you're yelling on that phone call. Can you.

Can you shut up?

But then we'll take a walk with the

dogs at the end of the day.

And normally the talk is something about one of

our businesses and how we've got to restructure it.

And I think sometimes we have to

be intentional about not talking about work.

We've constructed our life around it,

for better or for worse.

I don't know, doing anything

entrepreneurial, it obviously involves risk.

You all are both in this risky position.

Do you ever worry about that?

Hey, what's our income going to be like?

Hey, that gig didn't come through, or I thought

I was going to get this Enneagram program going

with this company and that didnt come through.

Like, is that a thing for y'all or is

it just kind of like, eh were okay. Yes.

And again, this is where were on Reagan is a four.

Im a seven on the enneagram, which I always say

to my clients, hey, I would not be married to

my husband if it werent for the Enneagram, because it

helped me to see why he is the way he

is, because he's so different than me.

And some of that is, like, cultural overlay.

And personality wise, I'm the fly

by the seat of her pants.

I will figure it out.

Sometimes hopelessly optimistic, but I will

say sevens are great manifesters.

And we just believe that what we

think's going to happen will happen.

Reagan is the counter force to that energy and the

more practical one, but the one that might worry more.

And we were just talking about this today.

We have an amazing guy who is

a therapist and a financial advisor.

And so it's financial therapy planning

that we do every other week.

That's a very interesting combo.

It is amazing.

We love him.

Ed combs.

It is so great because we do

have, like, feast and famine season.

So, so summer is always slow.

And we've yet to really, really figure out how to save in

a way, to where at this time of year, about August.

We're not freaking out because the reality is

fall is bountiful for both of us.

But when we get to this point,

we've kind of gone through our.

The savings that we've built up to live on.

And so that makes us a little nervous.

Now, I will say we also.

Have you heard of profit first? Yeah. Yeah. Okay.

So we really profit first our businesses,

and we profit first our life.

And so we have a system down to where I

think it just makes so that things feel fair.

And we also are very diligent about saving.

And so we have buckets that we

are for people that don't know.

Every paycheck that comes in, we put it in

a spreadsheet, and it is divided up percentage wise

by what percentage goes to bills and expenses, what

percentage goes to personal spend, what goes to retirement

house savings, travel fund, health savings.

And so we have these buckets, and

we've built up a safety net also.

And so we've done a really good job of building

in these systems to where we're not flying by the

seat of our pants, but it can feel nerve wracking

when that bills and expenses account has hit zero.

And we're having a pull from some

accounts that we don't want to pull

from because we're saving for something else.

That is like, my answer to that, and I would love

to hear Reagan's, because his experience with this, he's way more

anxious about this on the regular than I am.

What say you?

Yes, I say I am way more anxious.

I will take that title, man, I

didn't make any money in July.

If you look at my piano, I made $0.

And so that freaks me out.

Now, here's the thing.

We also love the freedom that this lifestyle provides.

So knowing that we're not going to make a lot of money.

Her family lives up in the mountains of western

North Carolina, where the high is 75 degrees.

We live in Austin, Texas.

We go stay there for a month over the summer.

So it's not like we're just.

I'm just sitting in Austin

sweating and making no money.

So we try to take advantage of it.

But, dude, it's scary.

It's scary to get to the end of the summer

and to say, oh, man, I thought that money in

that house savings account was going to stay in that

house savings account for us to buy a house, and

we're paying the bills with it.

Ellie's done a great job of meeting me in the

middle, and the fact that we've got a single source

of truth in our system that works for us.

And by the way, anyone who's listening to this,

pick and choose from all the systems and find

one that works for you, because none of them

is going to be uniquely suited to you.

But we found a rhythm that works for us.

Do we have our weekly family money date every week?

No, we miss it.

But that's really brought a lot of calm

and, dude, people book events six months out.

The furthest I have business booked is January of 2025.

You look at the rest of

next year, I have nothing booked.

And so that's very anxiety inducing for me.

And hindsight, after doing it for seven years,

man, you know, once you just put yourself

out there, like, it's kind of crazy.

You put your faith in something bigger than yourself,

and you keep doing the work, and, like, the

calendar kind of starts to populate once you start

to get to the end of the year.

But, dude, it's a constant question of, are we

going to make it the next six months?

Apart from the financial, are there other friction points

that having both of you being entrepreneurs creates?

We have worked through a lot of them over the years.

It used to be, yeah.

Who's going to get what office at

what time of day for client?

You know, kind of like, who's more important?

Some chest puffing that we go on trying to

get into a rhythm of each person's daily routine.

And how do you honor their routine?

How do you not come in and interrupt them

and want attention when they're in the flow?

We both still do that and get mad when the

other one doesn't give us the attention we want.

Right now, we both have different things about

our business that are most important to us.

And so we can take our own

bias and project that onto the other.

And we have to be, I think, careful around that.

Give you an example.

Like, I believe that social media marketing is

a free opportunity for all of us.

And it is a huge part of my work and online presence.

It's how I've built both businesses.

I typically do that at the end of the day when

Reagan is ready to play and he begins to think that

me being on my phone is me not giving him attention.

And I have to be like, no, I'm still working.

So there's those little points of tension, but we've just

worked through it over the years, and I feel like

now it's just the dance that we're going to have

to play around starting a family and both wanting to

continue to work, and so then both taking up childcare

duties, and at some point, we're going to have to

figure out a rhythm of who gets to say yes

to this opportunity and who says no.

Because what if we have work at the same time?

Who's going to be home?

So those are other hurdles we will have to cross.

But we've done a really good job

of, we're very open and direct communicators.

I think I witness a lot of my clients or

friends, even parents, in their relationships, and I think, gosh,

we're so much more brutally honest with one another.

We just tell each other like it is.

And I think that really makes us

be able to move through those.

Those points of conflict, because we

just don't really hold back.

I think a new source of friction, I don't

know that it's necessarily conflict, but friction that's coming

up is Ellie's extending more into her Enneagram, coaching

for teams, and she's doing more corporate work.

She's jet setting as well.

So historically, I'll travel two weeks a month.

I historically don't have to ever think

about it, and I just book everything.

But now we're looking into our fall, and we're like,

oh, dude, we both just said yes on the same

weekend and who's going to watch the dog?

So that's a new thing to have to figure out.

And I think an old one that we worked through, but an

old one is I eventually, at the end of the day, get

to the point where I'm ready to stop talking about work.

And I want to connect because I'm a

heart type on the Enneagram, and Ellie's a

head type, and she's just constantly interested in

what new things she could be trying.

And so we really had to work through moments where we'd be on

a walk at the end of the day, and I'm over it.

I'm over work, and I'm over the challenges of the day.

And she's wanting to brainstorm something

which feels like love to her.

And so I'm wanting to connect with

her, which feels like love to me.

And so neither of us is getting what we want, and

we have to figure out, okay, when does she get her

brainstorm time and when do I get my connection time?

That really required a lot of intentional

work because we're just built differently.

And the Enneagram helped us to put language to that.

It's good that you both have fully embraced that.

That would be tough if one of you

was all in and the other was not. Totally.

So that's great.

Talking about down the road, having a family someday

and traveling, it reminds me of a story.

And so, Reagan, this is more for you. Lesson learned.

Earlier in my career.

This is even before I started my business in 2013,

I traveled to La 26 times on top of a

whole bunch of other places my wife and I had.

I think we just had two kids at

the time and 2 hours time difference.

I'd call her, I'd get back to the room

at 839 o'clock, and she'd be getting ready for

bed, and she'd say, what'd you do tonight?

And I was like, oh, my gosh.

The client took us to this amazing sushi

restaurant, and we had this and did.

And she goes, I made pancakes for dinner.

So just little pro tip.

When you're traveling and down the road, when a kid

does come, careful how you talk about your adventures.

Noted.

Well, guys, this has been awesome.

I'm going to wind down with our question.

We always ask, and that is, what's next?

What's next is I'm stuck in the breakout

sessions track of conferences that I speak at.

And it's great.

You go to a conference, and then there's the concurrent

breakout sessions, and 100, 150 people go to those.

And then there's the main stage speaker, and it's in

front of the 800 people that came to the conference.

And there's normally an opening

keynote and a closing keynote.

And the book was certainly something I wanted

to do as an emotional endeavor and as

part of my journey of self discovery.

And it was very intentionally created to help me

focus in on a message that mattered to me

so that I could become a little bit more

known for helping people solve a specific problem.

So as I'm looking into the next year, next 18

months, I want to see myself starting to take a

swing at more of those main stage keynote opportunities.

Because I think what that allows me to do is

get the message that I believe is really important in

front of more people as an act of service.

And as we're hoping to start a family, the

ticket price for those keynotes is a little higher.

So that allows me to travel less and do less

events and still take care of our financial situation.

So that's really where I want to

be focused from a business perspective.

Ellie, how about you?

Well, I'm sure you won't be surprised to find

out that I'm working on a new business.

I was wondering when we were talking earlier

about how to help other people, is that.

Am I thinking the right path?

It's not that one.

It's not that one.

So it feels more like the next iteration

to this work I'm doing in the enneagram.

And I have a name for it.

I'm not sure I'm ready to publicly put it out there.

And we have the branding all done.

Website domains taken, emails, set

up, all those foundational things.

It is a community based membership for women to

resource and educate them on how to improve the

quality of their life and achieve optimal health.

On my own journey, I have experienced being back in our

healthcare system, but on the patient side, and all of that

rage that I felt as a nurse and frustration, the reason

I left and said I got to go find something so

I can come back and just dismantle this whole thing.

All those feelings came up over

the past year and a half.

And I struggled so much to find the answers and

the help that I needed as an educated white nurse.

I even myself, I could not figure out

who to ask and what to do.

And so that's really been what

has inspired this new business.

And it will be an online platform for women to

join at a very affordable rate, to be able to

talk to one another, to ask questions for the community

to help build more resources for each other.

I've seen that to be very effective for women

and then also a landing place for I've got

these symptoms and what is going on, but also,

how do I live a healthier life?

What do I need to do?

Because our culture just doesn't really encourage

those answers and those lifestyle modifications to

really be the best you.

And so that's the next thing.

Well, it's doubly exciting and really appreciate you

guys coming on and sharing your story. Thank you, Scott.

Thank you, Scott.

Thanks for having us.

That was Reagan Pugh, speaker and author of two emotional

and Elle Pugh, founder and CEO of Beyond Enneagram.

To learn more, visit

reaganpugh.com and beyondyourtype.co.

If you or a founder you know, would like to be a

guest on In The Thick of It, email us at [e-mail].