The Secret Sadness of Entrepreneurship

David Allan: Hey, everybody today on the show we have Eric Stafford. I think I first heard about Eric from buddy of mine
Colin Theriot, and you guys are good buddies Eric?

Erik Stafford: We are. I’ve known Colin for a number of years he’s a very good dude.

David Allan: Now you come from an advertising and design background you’ve won a bunch of awards and you’ve been a serial
entrepreneur, product creator and soforth lending your expertise to multiple businesses over time how did you get into the, you know, the advertising world and maybe take us through your sort of
superhero origin story about how you got into all this.

Erik Stafford: No sure absolutely so on you know I guess you could probably say gave that my life has been a series of realizations and moments where I just you know sort of was like well this just isn’t gonna cut it anymore and I’m not sure if you could say that’s true about everyone but I think that’s probably true about most people I thinkmost people you know when they look back on their life with a critical eye they can kind of see where they had these very specific moments where they just decided look something’s got to change
right and I know that I’m a marketing wonk so I read a lot of books I know that Malcolm Gladwell called this a Harajuku moment. A moment… a defining moment right? And I think Tim Ferriss may
have had stolen that from him and used it and what his folks as well but the first one that I can think of specifically as it relates to busines was you know I had two young kids and we had built a very successful advertising agency here in Southwest Florida but I
was working 80-hour weeks and I just you know I just one morning realize look you know I can’t do this I can’t do this forever you know I I will work my way into a grave and my kids will be you
know grown and gone and I won’t I will never know them and you know it’s a painful realization because my entire life I had wanted growing up to be a creative director in an ad agency right and so I you know I out there and I got to that point and realized well you know I’m not happy and you know we were winning all these

incredible awards addy awards and Art

Awards and um we’re even featured in all

sorts of press we’re doing incredible

work for clients that really inspired me

but it just it just wasn’t sustainable

as far as I was concerned and so I

realized I had to make a change and so

you know I majored in fine art grew up

got to the position that I wanted to be

in in sort of the creative world I was

running an ad agency the creative to the

creative department of an ad agency and

so I realized something had to change

and so I started researching different

businesses that I may start and that led

me into internet marketing and led me to

creating my first products and things of

that nature and I developed a bunch of

digital products I hadn’t built an

incredibly successful business and then

one morning woke up and realized that I

was unhappy with that business and I

understand right now that I’m probably

coming across as the most ungrateful

turd on the planet but but that’s

literally what happens to me yeah

well that’s exactly why I wanted you on

the show I’d seen a video yours I think

you went on so Facebook live or

something and you were talking about you

know how you woke up one day and just

realized and it sounds like for the

second time or more that this wasn’t

what you wanted to be doing and you know

I have definitely felt that way for sure

I definitely instantly related to that

I’d started other businesses in the past

and and gone on for some cases years and

then realized this is just not what I

thought it would be and definitely don’t

want to do this anymore and you know I I

would just outright just quit like that

day basic right as if as if I was never

interested in it at all and so that’s

that’s so maybe talk about that I mean

I think it takes a while to get to that

point to that maybe people don’t even

realize because I know I didn’t yeah I

mean it depends you know I tend to think

that entrepreneurs are wired a little

bit differently than the normal people

and you know most entrepreneurs myself

included aren’t willing really so much

to settle and so even if I were willing

to settle I don’t think the universe is

willing to let me settle and so that’s

the whole reason that I quote-unquote

quit my job to begin with was because I

just didn’t didn’t feel that working

that many hours and missing that much of

my kid’s life was something that I could

put up with right and so that’s why I

quit my job to begin with and so when

this happened the second time in my

business when I fast forward from you

know from the early two-thousands to

like 2008 and this happened in my own

business it was a very sort of similar

thing it was like you know I’ve woke up

and realized I hated my business but it

was quite a bit it was quite a bit

harder for me to get my head around and

it was quite a bit harder for me to

stomach but it’s it’s a very similar

feeling it’s like right well you know

I’m not willing to do this anymore this

just doesn’t work for me anymore but

when you’re an entrepreneur and it’s

your own business and it’s something

you’ve built with your own two hands

from scratch especially you know when

you’re in an industry you know sort of

similar to the industry that I was

working and at the time you know is

working in sort of like personal

development online marketing digital

digital product development things like

that it’s very difficult it’s very

difficult to admit and and I think this

may be true for a lot of business owners

difficult to admit that you’re unhappy

when you’ve worked so hard to build

something that on the surface appears to

be going so well right right and so you

know at the time I was spending all the

time in the world that I wanted with my

kids my wife and I were extremely happy

I built an engineer to life that I

really wanted but I really had always

envisioned but the physical act of doing

the work that it took to live that life

I hated it

and it’s it’s tough to admit that you

know there’s people that subscribe to

entrepreneurial style followings there’s

a lot of talk about being grateful and

about gratitude and about abundance and

so it’s very difficult you know to say

that you’re unhappy you can be grateful

and yet I’m happy but I didn’t quite

understand the distinction at the time

and so I just remember a very long

period of time

of me sort of thinking myself like Eric

what’s wrong with you man why are you so

on the motivated are you say depressed

like look at you know look at the money

you make and look at how you get to live

your life like if you told any of your

friends that you felt this way they

would they would laugh at you they would

think you’re in it but I couldn’t hide I

couldn’t hide from those feelings I you

know I I clearly was not happy and so

it’s a very difficult thing when you’re

an entrepreneur to sort of own that and

separate it from thoughts of like not

being grateful or not feeling fun the

secret sadness it is yeah it’s sort of

this painful solo you know journey that

entrepreneurs have to take and you know

I’ve not heard anyone else talking about

this and yet I know it to be true for a

lot of my peers and my colleagues and my

friends and you know I’m I’m grateful

that when I went through this process

and as you said I’ve gone through this

process three times now but I’m grateful

that uh you know I kept the rails on

somewhat for each of those three

transitions right but you know I know a

lot of people where this process is led

to you know heavy heavy alcohol abuse

and heavy drug abuse and lots of you

know trips to Vegas and full of spending

of money interactions with prostitutes

cheating on spouses even in some cases

suicide and it’s just it’s a it’s a

secret sadness that not many

entrepreneurs are really able to talk

about or discuss and an own you know

it’s really difficult to aim the lens at

yourself and I certainly know I didn’t

feel like I could talk with my wife

about this you know my wife just wanted

to know that

everything was gonna be fine and that we

would still be able to get Evan the

private soccer lessons and that we’d

still be able to take the summer road

trip and um you know so I very much felt

alone in this journey I didn’t feel like

I could speak with any of my colleagues

or peers I didn’t want anyone to

perceive me as being weak and so it just

was that sort of thing I just sort of

sat with yeah I think that’s uh that’s

I’ve seen that I think I saw it until we

started talking here just recently about

this I you know I sort of reflected

knowing that you were coming on the show

just kind of like you know where have I

seen this elsewhere you know and I was

just like yeah you know I can pinpoint a

few other people where I just like they

said things to me at the time which

didn’t really register and I thought to

myself probably what you like you were

saying about your friends how they would

have judged you I think I probably I

never said it to their face but if I

judge a thing like man you know talking

about but I was just kind of like oh man

I’m sure it’ll pass kind of thing you

know and then and then I had it happen

to me in at least one occasion where I

was just like man I just don’t want to

do this I just and I think it was a sort

of multifactorial problem that sort of I

came into and that I really just wasn’t

what I thought it was I didn’t really

want to do it anymore because I aspect

of it but not the other six you know

yeah I could I remember thinking myself

like really I worked so hard for this

and it’s finally I was finally going

successful yeah but you could see that

it was going to be so for you and you’ve

done this now three times where did you

start with at first did you realize like

I got a I mean obviously quit but but I

mean did you have a specific plan of

action that you were gonna take or did

you later come into that well I mean I

think it all starts with that sort of

harajuku moment that moment where you’re

like shit what have I done like a moment

that moment where you go how did I how

did I get here you know and it’s funny

because you know I can track moments

like that throughout my life

now that I know what to look for in

terms of you know relationships or in

terms of my health you know if if you’re

overweight you know you you will never

lose the weight that you want until you

have that moment no amount of your

spouse beating on you you know I speak

from experience I lost 60 pounds over

the last several years and it wasn’t

easy yeah yeah thank you man I

appreciate it it wasn’t easy but it

became so much easier once I had that

moment and that moment in terms of my

weight loss was I actually was flying

somewhere and couldn’t get a seatbelt

around right and the stewardess said to

me do you want a seatbelt extender which

apparently in America is a thing which

is even creepier but but anyway that was

the moment dude where I was like this

has to change this this this is

embarrassing this is shocking this is

shin I hate this this has to change and

so it starts with that moment and the

moment with the ad agency with with my

sort of first career was I lived about

about a 20 mile drive from the office

but during season you know Florida’s

very seasonal during seasons sometimes

that drive could take upwards of two

hours and so during season I would I

would try and go to the office really

early to avoid traffic and then come

home either early in the day if possible

which never happened or late at night

and one night I was driving home late at

night and I started to fall asleep at

the wheel and I opened my eyes and

snapped out of it and realized I was in

the middle of a red light and so I

slammed on the brakes and my Jeep sort

of fishtailed and did this earth thing

and I stopped at 2:30 in the morning in

the middle of a red light with no other

cars around anywhere if there had been a

car there I would have been killed and

that was the moment where I was like

yeah I got to do something about this

and so it starts with that moment and

it’s funny dude you had said you know

that you know there’s been a couple

times in your life where you found

yourself in situations where you’re like

yeah right this doesn’t work for me I’m

blowing this up I’ve done and that

certainly is you know one of the op

in my experience when this happens

there’s there’s four options the first

option is to ignore it and do nothing

which we’ve talked about a little bit I

don’t know for most people especially

entrepreneurs I don’t know that that’s

really an option right I don’t think

entrepreneurs are really wired that way

and I think you know we might be able to

ignore for a little while because we

like you know we like giant incomes and

we like being able to have that car or

we like being able to live the life we

live or whatever but right I don’t I

don’t think for most of us we can ignore

it forever so I don’t really see the

first option as an option the second

option is to quite simply get fed up and

blow it up and just walk away again I

don’t know that that’s the best option

but again we’re finicky beasts us

entrepreneurs and sometimes we’ve just

had enough and that’s it right so um

that certainly is what happened in 2010

or so with the first internet business

that I had built I woke up one morning I

received an email from a customer a guy

that had purchased one of my courses in

the middle of the night and he emailed

me and said hey bro I bought your course

in the middle of the night it really

needs to work for me because if it

doesn’t I need to make five grand by

this might even three grand I need to

make several grand by this weekend

otherwise my kids and I will be homeless

Wow and I was like yep I’m done you know

because my sales letters never promised

any sort of money from the sky or any

other yeah but at the time you know it

was 2010 and the the housing crisis was

becoming a very real situation that the

banking collapse was looming and it was

just a very difficult time for a lot of

people and my systems and my lead

generation systems my affiliate stuff

was geared to bring me those people and

I didn’t realize it until that moment

and and at that point I blew that

business up I literally uh I logged in

oh my god I can’t believe him tell

people I logged into autoresponder I

deleted 75,000 people from my email us

Wow and then I logged into my CMS or

whatever and I deleted all of my monthly

members I had over a thousand people

paying us $50 a month for a monthly

membership for training and stuff and I

logged into my FTP client deleted all my

websites and I basically blew it up I

blew it up and I walked away and I like

to tell people that you know I had

sunglasses on I was walking slowly it

was exploding behind me it was very cool

there were kittens involved like it you

know that’s but no in truth told brother

it was extremely painful I spent I spent

a long time right it’s just not

understanding what had happened how I

built a business I hated and not

understanding what to do next

worried about my family and not sleeping

it was a terrible time when I felt like

a failure dude because you know who he

does that right and so I think the first

step is that Harajuku moment of

realizing that you are no longer

comfortable where you’re at and you’re

no longer willing to settle with where

you’re at and then the second step is

understanding that it’s okay and

understanding that all businesses go

through silence and that all

entrepreneurs shift and change goals

shift and change a good example of that

being Netflix you know your your your

longer in the tooth like I am you

remember when Netflix used to just be a

DVD company they would send you DVDs in

the mail and they transitioned from that

to being an online service and now

they’re transitioning from that into

being a movie studio yeah right and so

on

you know this stuff it when you

understand that this stuff is inevitable

and that it’s natural and it doesn’t

mean that you’re a failure then you can

start to look at other options besides

the first two which are to ignore it or

to blow it up right okay you see a lot

of people serve and that maybe that’s

exactly why is you know you see people

pivoting their businesses and so forth

and you think to yourself oh this guy’s

just being very clever

trying to get into something new but I’m

thinking about it now I’m probably sure

there’s a lot of those scenarios with a

person well that’s how they got out of

where they were yeah if they’re smart I

mean it it definitely takes a lot of

self-awareness and it takes a lot of a

willingness to really aim the lens at

your own self which can which can be

painful it’s it’s not always been an

easy process but but I you know I will

say that when you understand that this

sort of thing happens you know I was

chatting I was chatting with one of my

favorite authors a guy named Marty

Neumayer who wrote a book called the

brand gap and he wrote also called zag

which are incredible marketing books but

I was chatting with him once and and I

was explaining this to him and he goes

oh yeah dude like that’s happened to me

like six times in my life that happens

to me like every two years

and I was like shut up really I don’t

hear about this on you know on podcaster

in the interview I don’t hear anyone

talking about this and he’s like now

dude it’s totally natural like you know

everyone pivots my first business was

designing software boxes there’s not

even software boxes anymore let alone a

computer stores to buy software and I

had changed my business and I was like

oh wow shit and so um yeah I mean

understanding it and owning it allows

you to look at like you had just

mentioned the other two options which

are you know to remove yourself from

your business you know methodically

remove yourself whether it’s something

as simple as just starting to outsource

some of the things that make you the

most unhappy document what you’re doing

and outsource it or hire someone to come

in and and do those tasks so that you

don’t have to and you can focus on other

more more liberating and more more soul

filling tasks in your business or you

know to go as deep as to remove yourself

completely you know to hire an

Operations Manager and pay him a large

salary and just take a smaller

percentage of the business and let

someone else run it or even sell your

business right that’s certainly an

option and then you know the fourth

option is to realign your business which

you had mentioned it’s to sort of pivot

and and move

your business back into alignment with

your ethics and with with you know where

you’re at and what your goals are right

you’ve seen that over time with a few

I’m trying to think it doesn’t matter

even to mention you know names but you

certainly have seen that in the internet

marketing thing over time you’ve seen a

few people go through that where they

chose to rely in they’re there for

ethical issues or whatever their reasons

were you can sort of see you know coming

up born-again marketer almost of thing

right that yeah it’s tough man it’s

tough to separate it’s tough to separate

the reality from the chaff because you

know I know certain markers who have a

retirement sale every year right so I

mean it’s um it’s a very strange place

it’s a you know it’s not an

entrepreneurial it’s not commonly seen

to be an entrepreneurial trait to be

vulnerable right and to be open and to

be shamelessly honest with yourself

everyone needs to appear bullet right

and so it requires a certain level of

vulnerability to really look at where

you’re at and say you know look I’m

grateful I’m grateful but I’m unhappy

there’s a big big difference the most

recent time that this realignment

occurred for me was at the beginning of

the summer and at the time you know I

loved everything about my life except

what I had to do to live it that was

super happy we were making great money

I was never wearing shoes I was working

on my lanai in the beautiful Florida

weather I was working out at the gym a

lot I was going to yoga a lot I was

eating lunch with my friends almost

every day I was watching a ton of

European soccer yeah life was a really

good man but you know I would open my

laptop in the morning and just go oh

like really I got to do this today

yeah well that’s interesting too because

from seeing like you know we’re friends

on Facebook and so forth you know just

watching you

from a distance and that’s what was

probably you know real surprising to me

when you put up the video and I thought

okay well that’s interesting because I’d

see your stuff popping up you know you

would take your family to Vegas in the

Pacific Northwest and so forth and you

look like you’re just living the life

you know and again that’s part of that

you know no one I would have never

suspected for a second that you weren’t

happy with what you were doing because

you know you get the suppression of

people based on a series of photos

videos or snapshots on the internet or

whatever yeah yeah for sure I mean I

don’t feel that I was intentionally

deceiving people I think I was deceiving

myself yeah because I didn’t want to

admit it I didn’t want to look at it I

didn’t want to cast the lens at myself

and and like I had said you know I loved

almost every aspect of my life during

that time except one and so for me too

for me to go really am I gonna I gonna

blow something up again or am I gonna I

gonna do this again

really but like I had said you know as

I’ve done this now several times it’s it

I will say to those of you listening

that it gets less painful every time and

it takes less time every time and at

least for me it’s been a less radical

shift every time so this last time that

this happened it was a a slight

realignment that really has brought me

immense pleasure and happiness and

working again that’s great to hear man

yeah that sounds like you’ve learned

lessons of course from the previous

realignments if that’s the term we’re

going to use

and so yeah the fact that happens

quicker and stuff it’s not such a

colossal ordeal where you have all these

doubts cuz you’ve had these things

before and you realize what it is yeah

yep yeah the first time it happened I

switched entire careers right right and

the second time it happened I blew

everything up and started over the third

time it happened it was merely a

realignment a slight adjustment in my

path based on my shifting goals okay so

let’s take you back to begin let’s take

it back to the beginning of the summer

what was your business then and what did

you realign so I had built I had built a

business where I was doing conversion

consulting based on my experience in in

in the agency world and also in

participating in a lot of high-end

launches launching my own product split

testing a lot of my own pages and a lot

of my own assets and then working with

clients for so many years but I built a

business where I was just consulting and

helping other entrepreneurs with their

conversions and it was it was a great

business it was a really really

lucrative business we charged a $2,500 a

month flat retainer and we would meet

with our clients once a week or twice a

month depending on what suited them and

you don’t need a whole lot of clients at

$2,500 a month to live a very good life

but what had happened is a couple of

things the first thing that it happened

was I let I let some of my clients

readjust our arrangement to better suit

them and I loved I loved all of the

people that I was working with at the

time and I don’t think it was malicious

but I do think it’s human nature to try

and get as much as you possibly can out

of any situation that’s why people eat

at buffets right and so could you know a

couple of my clients one of them in

particular they were like oh well you

know we fired our in-house team and so

is there any way that you could just

update all the split tests this week and

and because I love watching European

soccer and going to yoga and hanging out

with my kids I said yeah sure no problem

and suddenly I was doing all of the

implementation instead of consulting

which is how I’d originally envisioned

isness right and so there was a lot of

school

creep there and there was a lot of extra

hours that were happening suddenly there

and I just didn’t have the balls to tell

them no because I loved everything else

about my life and so that happened with

a couple of my clients one of them

I went from consulting to actually

writing their emails okay and part of

this also is you know I feel a strong

sense of responsibility and I wanted my

clients to get results and a lot of

times I would just say to myself look

you know this this guy that’s working

for my client is an idiot I’m just gonna

do it like just tell your guys to leave

this alone I got this yeah because I

wanted my clients to get results right

and so the business sort of crept up on

the intern into something where I was

back to doing a lot of pixel pushing and

a lot of copy writing and a lot of

implementation which is not how I had

envisioned the business right another

one of my clients landed their dream

contract and literally got so busy that

they were no longer able to get on the

phone with me right and so you know I

would I would send them all my

recommendations I would send them my

conversion on it and I would say hey man

look let’s get on the phone next week

and they go yeah yeah definitely and

then we just never would and so you know

man just send the invoice it’s all good

we’re just slam and I just I was feeling

these people $2,500 a month and

literally doing nothing for right it

just didn’t sit well with me you know it

was minor things and again I understand

that I sound like the world’s biggest

herb for for being unhappy right to kill

someone for doing nothing I you know but

but again I mean you only live this life

once I think that when you can build a

business that’s in such alignment with

who you are and with your passions and

your goals that it literally is seamless

and you show up you know for your wife

the same way you show up for your kids

and the same exact way that you show up

for your clients it is so integrated

with how you want to live your life and

how you want to show up that there is no

distinction that that was my goal and

and so I had I had to I had to change it

so you made these so this sort of

as you were going along and then and

what way did you decide okay this is the

buck stops here we’re doing this from

now on yeah so what happened what

happened at the beginning of the summer

was that as soon as I sort of realized

that I was no longer able to deal with

this I think it became very apparent and

the work that we were doing for our

clients they were still getting results

but our heart wasn’t in it within a very

short period of time I gently let go of

or was let go of by almost all of our

clients within the space of six weeks we

sort of separated and went our separate

ways from nearly all of our clients

within six weeks within eight weeks all

of them were gone Wow and I tell you

what though dude

like no joke it was the most liberating

feeling in the world because it created

space for me to really spend some time

over the summer sitting and reflecting

on what that ideal business might look

like and where I might transition to to

fill me up and to make me happy does

sound liberating and I could tell just

by the way talked about it that it was

like this yeah it’s so true and you know

it’s an emotional thing for me to

discuss because you know I’d said

earlier that each time that I’ve gone

through this process it’s taken less

time and it’s become easier and it’s

also it’s also become more liberated and

more free and you know I I quite

honestly I never I never really thought

that it was possible to build a business

that I enjoyed so much I never thought

that it was possible to do something to

where I felt in alignment with with

really what I feel I do best for people

and how I want to show up and and the

results that I get for people the

Japanese have a a term for this actually

it’s called I key guy i ki GA I I

believe but it basically means your

reason for being and it’s a combination

between that which you love to do and

that which the world needs and that

which you are very good at and when all

of

those are in alignment with that which

makes you money then you have found your

IQ guys according to the Japanese you

found your reason for being I found mine

I found that yeah it’s no it’s like I

don’t know I feel like that scene in the

matrix right where every morning I wake

up and I grab my bulletproof coffee and

it’s like I see the code Wow check this

out

very cool that’s the slight real in a

long roundabout way I’m sorry I didn’t

answer your question but the sly tree

line that I made was I realized that the

best way for me to serve my clients and

the thing that I am best at and that

which inspires me is to help businesses

through this process it’s to help

entrepreneurs build businesses or

recreate or reinvent their businesses

into something that not only makes them

more money but also makes them happy

right that’s great ma’am it sounds like

you really have found that that

intersection people need and obviously

what you want to do so that’s that’s a

great realization

thanks man yeah it feels very good so

what is the immediate future hold for

Eric Stafford are you going to it’s it’s

not a sort of situation where it’s like

great let’s build a sales team and I’m

gonna build a webinar we’re gonna we’re

gonna blow this up and you know like

like I had mentioned I’m really quite

happy with every other aspect of my life

and so for me it’s just a matter of

putting that intention out there and

understanding that this message will

resonate with the right people and if if

that looks like a great fit for us to

work together then I’m certainly open to

that and if it isn’t then it isn’t and

that’s just out of this and again it’s

just super liberating to not feel tied

to those outcomes it’s just liberating

to know that I’m doing what I’m what I’m

here to do and so the clients the

clients understand and the right people

have showed up and I’m working several

clients and

and it’s incredibly rewarding now if

people do want to get a hold of you and

they listen to this and they they feel

like they may be in this or quagmire

were there you know secretly sad but the

what what they want and they’re thinking

about pivoting or blowing it up or we’re

just suffering and needlessly in

desolation that how do people get a hold

of you so the best way to reach me you

can certainly find me on Facebook I’m

guessing if you’re listening to this we

probably share some similar friends you

can find me on Facebook Eric Stafford on

Facebook or you can check out Stafford

marketing.com

or Eric Stafford calm those are my

websites awesome this is something that

virtually nobody talks about I’ve never

heard another not listen to every

podcast on earth but I’ve certainly

listened to a lot of the major ones and

I’ve never heard anyone I’m really

delving into this this is something I

think that exists probably in a much

greater number than anyone wants to talk

about or even understands kind of the

tip of the iceberg idea there but you

have some real good strategies and I

haven’t gone through it yourself Eric it

sounds like you got a grip on this thing

well thank you very much man I

appreciate you having me and uh and I

respect what you do so I’m proud to be a

part of it thanks a lot Matt and we’ll

be back again to the next episode and

hopefully we’ll have someone as real and

authentic and as kick-ass is Eric