Episode #191 – Kevin Rogers On Your Path To Freelance Success. Simple Ideas To Get Out Of Your Own Way

by John McIntyre

Kevin Rogers is a fellow performer.

For the better part of 10 years, he was a hardcore standup comedian making his living on the road.

Looking into the future, he saw older comedians who hadn’t “made it” and decided to shift gears.

With the help of a close friend, he found the world of copywriting.

Another comedian friend was also a little ahead of him on the very same path.

His first “sales letter” was a mocking treatise for a self-pleasuring device.

His friend told him it was better than 70% of the copy he came across.

From finding his first clients to advice he received from copywriting legends…

…this episode delivers the goods and may re-shape the way you’re molding your copy career

Dive in and listen now.

In this episode, you’ll discover:

  • What are the top mistakes Kevin hears from the client side of the copywriting business.
  • Kevin’s best piece of advice for every copywriter entering the field. (The two-part process for standing out.)
  • The “slippery banana syndrome” of the early stages of your copy career. How Kevin brought his focus in tight and his copy done.
  • HThe number one mistake people considering a copy career make. (It has nothing to do with getting good at copy.)
  • Kevin learned faster and escaped impostor syndrome with THIS advice from two legends.

Email Marketing Podcast Episode 191


Intro and outro backing music: Forever More by CREO

David Allan: Hey everybody, we’re back for another edition of the podcast I’m David Allan from makewordspay.com – we have a very
special guest today on the show, someone I’ve been looking forward to talking to for a long time he is a copywriter or a freelancer – you know mentors other copywriters he has a
wildly successful forum and stuff for copywriters that you may already be guessing who I’m talking about he’s also a
stand-up comedian… Kevin Rogers welcome to the show.

Kevin Rogers: Thanks for having me brother, I’m looking forward to the conversation

David Allan: Yeah it’s been good I’ve we have some
interesting things in common including when I started my own podcasts that I did called Takeover Tuesday and you
started the Truth in Marketing podcast I believe we were using the same music – by some weird we’ve been gone looking
for the same royalty-free music

Kevin Rogers: Right, exactly funny they think one of us is that’s a cool they picture us in there like conducting the band

David Allan: So let’s let’s go back maybe you know I’m sure a lot of people you know know maybe a little few things about you for those who are completely brand-new let’s go back to your sort of superhero origin story you know how did you get into all this marketing stuff.

Kevin Rogers: Yeah well it’s a pretty long and sordid tale so I’ll I’ll give you the highlight reel it’s you know I was a confused young teenagers I think we’re all supposed to be but you know 17 my kids 14 now and like other parents of kids his age are mapping out their entire professional lives you know it’s this all this pressure to know exactly what they want to do with the rest is crazy so yeah 18 and to win like deadbeat jobs

and not really you know know what to do

but love comedy and so I ended up on on

stage and an open mic night and

Wow is he a hooked man within five

minutes it’s funny Dave you know like

you’re a performer when people tell me

they you know I’ve been thinking about

doing stand-up I’m like well you have to

now like you you’re obligated to

yourself and potentially the world of

comedy and entertainment to go find out

if there’s something there right because

it’s not a normal thing for somebody to

want to do this actually right it’s been

fear in the world just any public

speaking let alone gun everybody I’m

hilarious you’re not gonna believe what

I’m about to say you know you gotta be a

weirdo and so it’s if it’s for you

though it’s like this you know you

change on a cellular level the second

you you walk off stage and can breathe


the first time and that’s what happened

to me and yeah so that was it man you

know ended up figuring out how to get

rode gigs and spent almost ten years on

the road probably seven like hardcore

traveling that was how I made my living

took a shot at ya sitcom riding out in

LA and some different stuff that I

didn’t end up loving like I thought I

would and and then you know decided I

had to get off there I really just

burned out man I just couldn’t couldn’t

stand up in front of you know 24 you

know southern southerners there Warner

Robins Georgia you’re going yes it was

pretty good be funny not feeling the

inspiration here so uh I you know what

do you do then it’s like I didn’t also

didn’t want to become god bless them you

know there’s there’s there’s guys that

scared me for my future when I back then

you know cuz cuz I’m seeing them in

their 50s and right I mean it can kill

the room and they’re solid club

headliners but you’re like I don’t know

if you’re ever gonna get that break you

know and I was like I man if I hit like

if I’m approaching 30 and nothing’s

happening I gotta think this over you

know and

it’s kind of what happened it’s like I

tried some different avenues and I’m

like I don’t know how this works like

how do I get how do I get in control of

this I couldn’t see that right because I

didn’t understand business certainly

didn’t know anything about marketing so

did a bunch of like no resume jobs

bartending and in in Belle hopping and

through some miraculous you know kismet

found this copywriting thing and

discovered Wow hey a lot of those

instincts that serve to me as a comic

can work here as well and fumbled my way

through the process of getting those

early clients and you know made a go of

it and it’s been amazing yeah you know

when you’re looking back at the you know

when’s the first time you really heard

about copywriting when somebody actually

said that word or you he thought what is

that her totally yeah I remember clearly

because I thought it was the dumbest

thing I’d ever seen right like a friend

of mine named Chris Tomasulo he’s kind

of known in the industry yeah

yeah yo doc sulo a really brilliant guy

and that was sort of the amazing thing

that happened was I was working for an

old comic friend of mine who was running

you know timeshare resale company you

know basically a shady as it sounds

although he was trying to do it right

until the crack took over but that was

another story but so he hired Chris came

in to consult and Chris’s a master of

inbound telephone sales you know but I

was learning a lot from Chris and really

liked him and he knew I loved to write

and so he’s like you know you should try

you should look at copywriting the hell

does that mean and he showed me a sales

letter and I was like it was one of

those like you know nineties you know

early 2000 sales that is where it was

like purposely really ugly and and I’m

just like honestly I was like if

somebody sent me this I would

immediately mark it as spam you know

like it but but then he started

explaining the the persuasion behind it

and why it was ugly and and how it and I

was like I started getting really

interested then he turned me on to so

it’s a Halbert and Carlton and I started

reading there

their blogs and I was like now it was

like electricity at that point it’s the

hope so as I studied it then it was the

big problem of how do I get someone to

pay me for this find out if I’m good

enough to get paid right right that

becomes the next problem absolutely so

what were those first steps like did was

Chris giving you you know ideas or were

you looking around or out of yeah Chris

was helping me discover that I might

actually have some I’ll tell you what’s

funny is the first thing I ever wrote

was I was mocking copy because I I was

just kind of being a smartass and I

wrote this and I read a few letters in

thought I get this whole thing and my

instinct is as I guess a comedic thinker

was to write satire right right right

and so I wrote like half of sales letter

about the in my mind the product was I

don’t know mature audience is like I

don’t know how to even say this without

no go for it being disgusting but the

big joke was going to be the product was

you know a device that helps you blow

yourself okay you might want to edit

that in some way or am I not

but to me it was just funny like like

how do you build up to this right and it

was all about you know it was discovered

this ancient art of self-gratification

was discovered in in a in a cave atching

you know and and I’m just like cracking

myself up writing this thing right and I

show it to Chris and he goes look he

goes he goes I know you’re being a

smartass but this is actually pretty

good he’s like this is probably better

than like 70% of the copy I sees I’ve

seen it you need to maybe like seriously

think about you know yeah that’s good so

yeah so then the other amazing I guess

you know if you look back it’s like

amazing things happen when you’re

supposed to be on a certain path right

right so then I found out through a

weird email chain letter among cold

comedy friends that of comic

my name VIN montello was studying that

Masterson course okay and I was like why

you know what are the chances so I start

talking a VIN and VIN was like just

starting to get his first clients and so

he was actually really instrumental in

me figuring out how to you know respond

to certain you know job requests there

was a forum back then called the

copywriting board or the copywriters

board okay

written by a run by Michel Fortin and

that was a great board that’s kind of

the inspiration one of the inspirations

for copy chief hey cuz that went away

and then there was just like the warrior

forum and all these cesspools you know

yeah so then my very first gig was the

guy post that he wanted an autoresponder

series and I was still really new to the

whole marketing side of it you know and

especially like digital marketing and so

guys like I need an autoresponder series

and if you’ve you know you send me some

samples so I so VIN goes here’s what to

do he’s like he’s like tell the guy

write to him and tell him you’ll eat

normally it’s a hundred an email but

you’ll do all five for 300 as a package

deal I go okay great I’ll do it I go by

the way what’s an autoresponder what

does that even mean to me so the guy and

that had to write one you know mm-hmm so

I literally sat on my kitchen table and

in wrote one about a golf product and

the funny thing is did I don’t golf

you know I’ve gone flike twice in my

life I don’t like it I’m not interested

in it but I don’t maybe cuz I was

studying Carlton and I know Carlton

wrote like golf ads no I got that seems

interesting enough to write about so I

sent it to the guy and I get the gig you

know and it was funny was he wrote to me

he said you know some other people were

had lower prices than you he’s like but

I can tell you know what you’re doing

so I learned a lot of that like one is

like just go for it even if you really

don’t know what you’re doing it you know

if you care about doing good work it’ll

probably work out okay and the other

thing is like have somebody watching

your back you know like I you know if I

wouldn’t have known that I then could

check my work I don’t think I would have

had the confidence to even put myself

out for the gig right right so you know

it’s it’s a tricky thing with

freelancing it’s like you don’t need to

wait around forever for some magic power

to anoint you that you’re ready you also

don’t want to promise something you know

you can’t deliver so but you know if you

have a mentor and you have some backup

in some people around you who can help

guide you then you can definitely get a

head start a lot faster absolutely

that’s very good very good advice so now

you are a mentor for copy writers and

copy chief has taken off and become a

real valuable and favorite resource from

many up-and-coming copywriters let’s

delve into some of the pitfalls and

stuff of the freelancer like you said

you just listed off stuff like maybe

imposter syndrome where oh yeah you know

getting here getting your first clients

and stuff like whatever yeah I’m sure

much like when I take a look at people’s

copy and critique it and stuff this is

usually the same mistakes that are being

made over and over again is that the

case with relaxed copywriters and and

what do they what do they screw up huh

you meet from the writing from the

getting into it part and then yeah well

I guess on the writing part we can we

keep going forever you know with some of

the beginner mistakes but I think yeah

some of it is like I think well let’s

just let me just say what I know helps

right because I guess I’ve coached a lot

of freelancers now I would say the the

best thing you can do for yourself when

you’re starting out is just saw–

specialize and I know people say this

but not just in a certain niche but

decide like what do you want to write

what’s you enjoy writing what do you

feel particularly good at write so well

I’ll tell you one mistake I see is

people will come to me sometimes and say

okay hey

you help me figure out how to get some

clients and I’m like sure so let’s talk

about what do you like to write and

who’s been your best client or and

they’re like oh now I haven’t written

anything yet I just you know I read this

book and they’re my man and I come on

like so the number one thing is the

copywriting will not solve your

financial conundrum right they forget

that you’ll you’ll ruin your reputation

you’ll screw over some clients even if

you you don’t mean to like your number

one goal is not how do I make a living

at this your number one goal is how do I

get damn good at this right and again I

I see some people who are already good

floundering with their confidence and

not getting paid what they’re worth and

and those things too

but that’s better and certainly more


than the other problem which is I don’t

never have no idea what I’m doing and

I’m just out trying to hustle money for

for it you know so and I’ll tell you

that that is the biggest problem I hear

from the client side too is it’s really

hard for them to know who to trust and

even simple things like you know just

because they talk a good game on the

phone like you know vet their samples

make sure they’re actually their samples

like make you know and talk to some of

their past clients and make sure they

didn’t flake on the gig and you know so

those are the biggest problems I hear is

like they get the voice all wrong they

they miss deadlines or they ghost

completely right just terrible stuff

where it makes it so much harder for the

people who are are talented and want to

do good work so you know like – yeah

definitely don’t look at a copywriting

as the the quick fix to your money

troubles I tell people if they’re like

you know like I’m launching my my course

right now fit for the fur it used to be

just private one-on-one and it was

really expensive now it’s 10% of that

price just for the curriculum which I

still do live right but even now people

come to me and they’re like hey if I

take your course can I can I be getting

how much do you think I can be getting

next month and I’m like don’t take the

course I don’t you know you’re just

you’re looking at this all wrong

it’s a foundation on which you can build


career but you got to be committed to

the long haul of this I’ve seen it

happen in three months for people I’ve

seen it take three years you know it

absolutely is not a I don’t know what to

do go figure out Facebook AdWords or

something like that don’t don’t try to

you know put people’s whole career in

your hands for how you’re gonna

represent them in a sales letter it’s

you’re not ready so what should be

what’s what a you know maybe top two or

three things that people should be doing

everyday if they’re there so they’re

gonna play the long game if they’re

gonna get better at this what what are

the top things they should be doing

every day they should be yeah breaking

down ads you know like really studying

like like hand copying is cool for me

not for the reason it is good to the

whole rote learning thing of you know

I’ll move my hand in this way and it’ll

see her into my brain what could copy

looks and feels like however I wrote to

Gary Pennsylvania when I was new in this

business and shockingly he wrote back

and I’ve basically asked him I was like

look you you and you’re on Carlton are

the only people who I literally had a

visceral reaction to your copy you know

and and I said I just have to I so

desperately want to understand how

you’re doing that is I said to him is

like is it an LP like what am i what am

i experiencing that would make me feel

that way you know yeah and he said the

truth is you you have to really believe

in the product

right if you really believe in what

you’re writing about then it’s it’s not

hard all you’re feeling is my enthusiasm

channeled you know obviously there’s

there’s some persuasion things in place

but it’s not trickery you know it’s it’s

genuine enthusiasm he said and he said

the if you want to get good my best

advice is read of control at every day

in and he said don’t just read it he

said but then ask yourself what is one

thing I might change about this ad that

I think would make it convert even

better and that was so huge to me

because I realized and then the John

Carlton who became a friend and mentor

later really solidified this to me it’s

like really what you’re getting paid for

is the ability to is jumping is calls it

critical think about the offer about the


well you know the relationship the

emotions it’s the thinking where we

really earn our money in and so if you

start developing that early that’s the

thing that’s gonna set you apart right

right look here’s what makes a

copywriter great it’s it’s not that we

all have access to the same case studies

and information and formulas and all

those things right it’s what is that

thing you’re gonna bring to it that

nobody else on the planet could because

you happen to be interested in in this

part this particular science or human

evolution or you know like you know ten

different writers can all have the exact

same product research but they’re all

gonna come up with different big ideas

and hooks because they all have this

unique DNA and the set of experiences

and it’s the combining of those two

factors that create the magic right so

you know think critically you know get

to get really good at research but don’t

ignore your other interest and your

freaky little habits and fetishes that

you know bring those other elements into

it and you combine those two and that’s

where the great ideas happen because

honestly you know if you’re good at

nothing but coming up with great big

ideas and understanding how to sell

those and in a sales letter even if

you’re not the greatest writer you’ll

have a great career in this business

they they will they will put other

writers around you you know what I’m


it’s the ideas that are that the rare

commodity in this business right that’s

very very good advice for a good advice

and now you mentioned of course that

John Carlton became a mentor and a

friend to you did you reach out to him

and forge that relationship or how did

that works I know a lot of people out

there are probably also afraid to reach

out to some of these people who share a

hold in high esteem yeah yeah it’s

interesting it is scary especially when

you’re not sure what you want from them

right and so the reason John and I is

relationship if all the way it did I

think is because first of all something

about John just really resonated with me

and I had this weird problem

early in my career and it got it must be

so much worse for freelancers now which

is you know I had I had information

overwhelmed but there’s a certain like

patch of development in a freelance

copywriters career where you’re you’re

good enough to get paid and get gigs but

you’re also learning so much and when

you’re actually doing the work when you

read something that opens up your mind

in a new way you really want to

implement it like immediately right and

so a few times I was being in the middle

of a sales letter and I’d read something

on like clay make pieces blog back when

it was active or on the that forum or

somewhere and it would be so

revolutionary to me I go man if I don’t

stop Fred I have to start this letter

over or I’m not giving the client

everything I’ve got you know and but

then eventually I was like I gotta I

gotta quit this like this is

overwhelming so I said here’s what I’m

gonna do I’m gonna I’m gonna only follow

one one great you know because my my

thing was if I could get as good as one

of the grades I mean like even a half as

good we take me probably years but that

would be good enough to have a great

career right and feel in control of this

thing and so I said I’m gonna choose one

and I’m shutting out everything else off

like I’m just um because I want to get

to know their thinking and their process

so well that it would literally like

they’re sitting next to me at the

computer and when I come to a crossroads

and the copy I could turn to them and

say what would you do right here and

literally know exactly what they would

advise me right and so for me I chose

Carleton it was an easy choice because

again he was he was my guy he just I

loved how he wrote and how he talked

about the subject matter he chose and so

I just studied the guy to death and I

was so obsessed with with him in his

work in his wisdom I used to drive

around back and forth to my job

listening to his kick-ass comedy

kick-ass copywriting his secrets you

know audio over and over and over and so

when I actually finally got in front of

him and reached out to him

I felt like I had earned his attention

not not just because I put that that

obsessed on him but the one other thing

I did was I waited for an opportunity to

earn his attention and so he had a form

and he used to do critiques and he was

gonna be out of town and he said hey

what why don’t you one of you hotshots

take over the critique for me this week

and you know show us your stuff and I

was like ah this is what I’ve been

waiting for right

I took the critique and I you know III

think I did a screen cap I must have

done it like three times you know like

just I can get it better better really

put a lot of work into it

and posted it up because I knew that

John would have to watch this to make

sure I’m not giving crazy ass advice you

know right and so John wrote to me

privately and he’s like hey I just wanna

I wanted to thank you you know you did a

really good job and I critique and he’s

like you know let me know how I can

return the favor I was like finally so I

said I said your honor I just want one

thing from you I could you look at my

some of my copy cuz I totally had

impostor syndrome at this point you know

I was exactly at that place where it’s

like am I even should I even be taking

this money like do I know what I’m doing

and it’s so he read my stuff and he said

you know yeah clearly you’re still kind

of new but you’ve got great instincts

your writings good and he said you know

overall I can tell you you’ve got the

goods and once I heard that I was like

good night everybody you know no more

imposter sin come from yeah I just felt

and uh and then from there we we just

kept talking and developed a friendship

that’s lasted jeez 10 years now so it’s

been amazing awesome if people want to

get a hold of you they won’t get

involved with you you have copy chief

and your coaching program and stuff

where should people go after they get

involved yeah just go to copy chief

dot-com and you know if your first visit

there you’ll probably see an offer to

get on the waitlist that means that we

open to new members about once a month

and you know until then you can enjoy

the you know the podcast are there on

the site and you know tons of great

articles we focus a lot on story and and

all that kind of stuff and copy so yeah

I’d appreciate you coming by and I think

you’ll dig it awesome I really want to

thank you for coming on the show Kevin

it’s long overdue I think and it’s been

this hours just flown by and I just want

to extend my gratitude for taking the

time out for our audience thanks man I

really enjoyed it and for everybody else

hopefully we’ll be back again and we

will be back again with another edition

of the podcast next week hopefully with

someone as insightful as Kevin

Leave a Comment