Episode #193 – Dennis Demori On Digital Nomad-ism Beyond The Hype

by John McIntyre

Dennis found himself in advertising a few years ago.

Working on marketing strategy and branding for Fortune 500’s and Non-Profits.

His first foray into business was a web design business which went belly-up.

Another web designer suggested “copywriting” might better suit his skillset.

Once revealed…

…he dove into the deep end with everything direct-response.

Then he began searching for a mentor.

Years ago he had a martial arts mentor and understood the life-changing value.

He’s pretty new to the whole world of freelancing and the digital nomad lifestyle…

…and his fresh eyes will reveal the truth, dispel some myths, and give you perspective…

…from someone experiencing it in real time.

He’s only been a freelance copywriter for a year but he learns fast and has plenty of opinions on what you need to do…

…to make it in this marketing game.

Dive into this episode now!

In this episode, you’ll discover:

  • How to avoid being a sucker while finding and vetting a mentor.
  • Two quick-start reasons you need a mentor now. (Or spend years flailing away in freelance purgatory!)
  • 3 “No-brainer” problems every freelancer (of any kind) is trying to answer every…single…day. (Here are Dennis’ solutions).
  • Why most “digital nomads” are focusing on a completely wrong factor. Change how you decipher true success from mediocrity.
  • A golden nugget of advice about content creation to start luring in the right clients. (Dennis shares 4 mentors he worked with…or continues to work with)

Email Marketing Podcast Episode 193


Intro and outro backing music: Forever More by CREO

David Allan: Hey, everybody we’re back with another edition of the podcast, I’m David Allan from makewordspay.com and we have a fellow copywriter on the show today he is a digital nomad he’s relatively new to the lifestyle so he’s gonna be demystifying some of the aspects of what you may think about being a digital nomad here and talk heavily about that Dennis Demori welcome to the show

Dennis Demori: What’s happening David, thanks for having me.

David Allan: Yeah man, it’s a real pleasure. I’ve sort of just become aware of you in the last maybe six months or so you know we belong to various face group – I’m just gonna merge those words together – Facebook groups together and so forth and you seem to have…be of like mind and you’re relatively new to this whole digital nomad lifestyle so it’s interesting to see some thingsyou’re sharing maybe let’s start like we normally like to do we go back to your origin story where you were before how you found your way into this Machiavellian world of digital marketing and travel and so forth…

Dennis Demori: Yeah sure so briefly I grew up in New York and lived all over the US throughout the ears and about five, six years ago I ended up in advertising okay and I work with a number of different clients region could not provost a fortune 500 and in my role at that time I was a brand strategist and it has the comedy cuz they’re pretty creative about the names in the advertising field like and maybe my focus was market research and strategy for our clients but I got kind of sick of it after a while I did it for a few years and then thought okay what’s next
and after a a brief failure as a web designer because you gotta feel your first business right sorry laughter after doing that very badly I I found out about copywriting I found out about it from a fellow web designer we mentioned that she had worked with several copywriters and design projects and I was like you know what that is probably a better fit for my skill set and I think there’s better opportunities with that and actually did write some copy when I when I started doing web design because my first client and was my brother versus are with your family nice
so I had to read the copy for his website because he sure as hell isn’t gonna do it I just went down the rabbit hole and I found out about direct-response copy a few months later and completely immerse myself in the books and the courses and working with mentors and all that thing so I haven’t been a copywriter for that long it’s only been a little bit over a year mm-hmm when I’ve gone through that initial learning curve very quickly because I just do it right in right the style should took real action yeah that’s been my focus of the full-time copywriter freelance copywriter for the past year and I’ve worked with a lot of different clients from financial publishers KP commerce stores to fitness coaches a little bit of everything…

David Allan: okay okay so those first steps you found out about it you started okay that direct-response is the thing what is that about you’d open to some of those classic texts we’ve heard about so many times
you also access to mentors maybe talk

about that like it was that something

that you were just like aware of in your

life in general or was that suggested to

you or how did that work yeah actually I

didn’t have access to an incredible

mentor years ago in back in college was

in that situation I got into martial

arts which is wondering like I wanted to

do since I was a kid I think a lot of us

guys too right

so I did it in college and he was


anyone who’s done martial arts no it’s

not yeah you get into it

learn how to kick somebody’s ass that

they do learn about things like

discipline and dealing with adversity

and challenges learning how to learn

like all these types of things that are

really important to us so that was my

first exposure to it and then

fast-forward to this past year or so as

I was getting my feet wet and direct

response copywriting I keep thinking in

terms of time and opportunity costs so

you know who’s the best person that I

can learn from and that can help me

really accelerate my career growth right

because if you look at for example

professional athletes

they’ve always got coaches right does it

matter my boudoir doesn’t matter if you

work bran or Kobe or whoever even even

presidents I know like for example Bill

Clinton had had received advice or

coaching from Tony Robbins mm-hmm you

know so it’s really it doesn’t matter

what what profession you’re in or what

level you’re at there’s always somebody

who knows more than you do can help you

we can see things from a different


right and and also help you save time

because right you’re not going to make

any more time and that’s more valuable

than money you know that saving the time

is the most important thing and getting

on the right track as fast as possible

so you so the copywriting mentors he’s

sought out would how did you vet these

people did you like sort of this

person’s always talked about or what

sort of steps to take well I was a

little sneaky about it you know everyone

everyone offering coaching or mentoring

or consulting today well I would hope

has testimonials right Shirley so the

video case studies so I can go to their

website and find out why I look at who

is doing the testimonials and then I

just look them up on Facebook and send a

message right and say hey I’m thinking

about doing this what’s your experience

been I think that’s the best way to do

it because once you’ve talked to

least a handful of people right we start

hearing the same thing over and over

again like this was good this was not or

you know I’d you written it do you

recommend it right if you have five

people or 10 people who all recommend it

that for me is a good sign to move ahead

right so that’s what I would do if

anyone else was is thinking about

working with a mentor or a coach off to

the students know and and the mentor

should also be transparent about having

you talk to the students if they’re kind

of like NDA or other people you can talk

to them that would be a red flag to me

so I give that some extra consideration


was there any mentors in particular you

want to give a shout-out to yeah yeah


so the the first one well actually I

worked with a few natan all of them

unless I forget anybody but I work with

Jenny Burress kind of be ER es gens

fantastic actually met her alone in LA

and she’s a copywriter but she’s shifted

I don’t know how her business is split

off right now but she does a lot of

coaching and horses for freelancers okay

she’s great to help you get in to

understand how to pitch clients right

very good for that so not for copy but

for freelance broad ones lying that

client acquisition very good and and I

also work with Lucas for Chesky right

she’s an awesome copywriter and I work

with him really to to just get like the

the one-on-one on direct response copy

Brett to understand that and he’s great

then I was also in the trafficking

Fellows Program okay welcome Chris Evans

they’re very good at the mindset of

business right and and and client

acquisition and paid traffic and all

that mm-hmm

and finally I’m work with Jake awkward

right now who run

reading an academy I’m moving in that

direction now that I’ve been praying for

the past year and working different

clients his whole thing is financial

copy working the big financial

publishers of Agora right so that is

another type of the skillset and angle

and copy ready that a lot of people

don’t don’t know about so I’m looking to

Jake now he’s great he’s no BS he’s he’s

through what he’s done things also good


awesome awesome that’s great those if

it’s a great lineup of people that’s and

that’s something I think a lot people we

have on the show had in common they had

some great mentors and accessed you know

to cut that learning curve down it makes

a huge difference and I would say if I

could pay two things that are really

really important to any not just sake

writers but freelancers one is or your

mentors you know have you never have you

never work with a mentor why not because

if you can find a good mentor coach

they’re gonna save you a ton of time and

they’re gonna help you avoid the

mistakes and get on the right track and

then number two is the environment

number two and we’ve talked about it in

the beginning of this and this interview

with ace groups yes Facebook groups yep

but your environment

yeah who are you hangin out with you

hanging out with go-getters and

ambitious people or not so I try to

surround myself with the absolutely best

people possible right yeah absolutely

absolutely is that old saw about your

the average of the five people you hang

around with the most or whatever however

it goes yeah it’s fully true that’s a

very powerful idea unto itself all right

so you started into the mentorship you

were cutting down your learning curve

you knew that it was copywriting you

wanted to freelance with what were some

of these mentors teaching you how to get

clients did you try it on your own

first how was the what steps did you

take there yeah

I mentioned four different mentors and

or I am working with each one for a

specific reason

okay so I think that’s the first thing

to think about is why do I want to work

with this person like I wouldn’t really

look for a general coach unless that’s

that’s really what you need but I think

what happens with most people is that

you run into a sticking point right

something is not working the way you

want it to so that could be like i like

i did this proper reading mentorship I

needed my focus there was still that

position right you know what can I learn

here that I’m not gonna learn in or in

books or this just gonna help me learn

it much faster sure because that’s my

primary skill set in my business or with

someone else I was working with it was

it was pitching like how do you pinch

fly it’s old right but that’s something

that a lot of people struggle with and a

lot of people do but they just don’t

know how to do it right we’re in it in a

way that’s gonna help them land clients

different I mean it’s way too much to

cover yeah today when I picked a lot of

things from different people so I think

with with really any type of freelance

business you’re gonna struggle with the

same things it’s gonna be one getting

better at your craft whether you’re a

copywriter or graphic designer what

designer whatever right who is client

acquisition how do you find clients you

know do you do that through Facebook do

you use cold emails what do you do and

then three is how do you convert them

do you have an organized sales process

from A to Z that takes somebody from

cold and not only anything about you to

hang you to work together right and I

think that those are probably that I

could think three areas that everyone

struggles with at one point or another


especially with client acquisition I’ll

give you one a good point right now

which I picked up from from the traffic

and funnels and which i don’t

following which is to focus on one

platform at a time and I give the same

advice for my clients when I’m kind of

in a consultative role is I see them

trying to do too much and I talked about

this on Facebook in my post is

everyone’s trying to do a million things

at once and you’re looking at Gary Vee

and Grant Cardone and all these guys who

are huge and okay yeah and they got

books podcasts video live streams posts

on Facebook event all this you know

public speaking events all this stuff

right last if you’re new or if maybe

you’re in your first year or if you’re

not at six figures of revenue I mean

whatever it is if you’re still kind of

just in the early stage however you

define it I think it would be to your

benefit to focus on one maybe two

platforms at a time so you could you

could do for example Facebook and an

email list right or maybe Facebook or

LinkedIn and then repurpose that content

on your blog right just just pick one or

two and go deep instead of like wide and

shallow right because as I would buy to

my clients you want to get famous in

your niche mm-hmm right if people don’t

know who you are they’re not going to

work with you and it seems like it’s

such an obvious thing but I can I mean

you and I know you’re in the same kind

of groups in circle but I guarantee you

can probably count the copywriter

there’s produced consistent content on

Facebook on two hands

maybe you name ten people yeah and

that’s it I can’t think of that many

more and I know a lot of them sure of

the ones who are actually out there

producing content it’s not many

and the reason is I think is because it

is a grind it takes time and it takes

work to do that and also I think people

are lacking confidence yeah it’s really

it doesn’t feel good does it feel good

when you post something and you get no

likes or you know a couple times but for

the most part I’ve been fortunate that

my stuff has got tons of engagement and

there’s a good sign yes so what I’ve

dealt with the same type of issues where

you’re like I just don’t know people are

gonna like this or if they’re gonna read

it or am I am I gonna look stupid so I

think a lot of people deal with that and

just kind of self sabotage themselves

and end up doing nothing right just gets

stalled oh it is yeah so just gonna read

that at that point I think people need

to do it do a better job of focusing I

think one or two platforms and dominate

the hell out of them and get known and

that is because finding acquisition is

just a big part of it that people

struggle with it with with it is why I

mention it I focus on one or two areas

that you can get really famous in I mean

just within the people that could be

your customers and that would that’s

kind of a key 8020 rule right where

should I fill this most Bannerjee you

know that is a really helpful tip this

does help me quite a bit yeah that is a

great tip actually is a great tip so now

your your remote you’re able to work off

your laptop you’re traveling you’re

experiencing this newly created and last

year digital lifestyle let’s delve into

some 1x I know our audience is you know

really interested in that and John of

course who started the podcast he

himself and myself are both digital

nomads let’s delve into that lifestyle

start demystify maybe some of the things

that people think are true or they have

a certain perspective that they haven’t

been open up to the other perspectives

and you’re fresh at this so you have the

best it’s all it’s all new to you let’s

just jump in and start telling us some

of the things that you

you may be thought and have been the

demystified in your own excursion I’m

just living the dream just retreats it’s

not like that at all it’s not in my

experience that’s the difference between

it for real and how it’s sold yeah well

here’s the thing first of all let me let

me take a step back doing the phrase

digital nomad is very popular and we use

it and when we say we we know what we’re

talking about like what the other person

sure we’re talking about someone who

travels and works online basically right

right but I don’t like that term and the

reason I don’t like it is that with

digital nomads I kind of don’t like the

nomad part of it and I love travel just

as much as anybody else but the problem

is when you’re living this kind of

nomadic lifestyle you’re not grounded

right no it’s really difficult to grow

up business when you’re constantly

moving every two or three weeks or even

every month mm-hmm because you need time

to get grounded you need time to be

familiar with a city right and just find

out basic things that sounds stupid but

I’m dealing with it right now is like

where’s the grocery store is it like

these little things that you don’t think

of as issues until they become an issue

like filters and so I don’t like that

part of it I also don’t like and this is

how you and I started talking on

Facebook the other day was I’m totally

pissed people off by saying this but

the digital nomads people in that scene

are really just focusing like where’s

the cheapest place possible that I can

live outside the US that has good Wi-Fi

what is mean and that is just a total

scarcity mindset because I see nothing

to brag about if you’re living somewhere

that’s cheap and a dumpy apartment

mm-hmm maybe with with roommates I mean

yeah we all start everywhere our

businesses have to start somewhere and

that’s from zero right I think that’s

because maybe fine for your period but

the goal for everyone should be to grow

right to grow personally even grow your

business and to get to a point where you

don’t have to be in the cheapest place

as possible like right now I was just

talking to friend last night about

visiting him in May and visiting him

somewhere that is absolutely not

considered a digital Nomad destination

and you would never guess what it is

mmm I’m thinking of going out to New

York that’s nice and working out there

working remotely for a month and you

never yeah in the different Nomad scene

you hear about Chiang Mai you hear about

a medi yeah maybe I’ve been hearing

about Mexico City and the amount and

yeah Vietnam I’ve got a good friend

there right now actually and I’m gonna

try to visiting this year but I think

people just need to take the longer-term

view of how can I really maximize my

life and how can I set myself up and and

I talked about environment before how

can I send myself an environment where I

can grow my business

because if your business is doing its

same revenue twelve months later

something’s wrong right or if you’re

just not hitting your goals something’s

wrong or you go like the Chiang Mai if

you drop shipping or whatever like you

learn by here doing and it’s really

going anywhere I mean what the heck are

you doing you can’t honestly tell me

that you’re leaving that much better

in Southeast Asia or in Latin America

than you are in your middle-class

neighborhood and Dallas or Chicago right

because it’s not evil I don’t think you

can prepare middle class the u.s. middle

class in Latin America or or off East

Asia there’s just this is a bit much

bigger divide and like SD right now in

Mexico see I don’t see too much of what

I would call a comfortable comfortable

to middle class of us right I see kind

of more like working-class for Mexicans

here you also have like the very

high-end red neighborhood which is

really just like choice for many so it’s

really it’s an enormous City it’s about

nine million people I think which is

about twice the size of the way better

than that mm-hmm like I would say that

there’s maybe three nice neighborhoods

there where there’s somebody from the

from the West in the US for Australia or

UK would would probably consider living

and living comfortably right that’s

excellent that’s excellent I mean it

awesome if people want to get a hold of

you Dennis how do they go about it yeah

a couple ways one you can check out my

website Dennis the more you calm and if

you want to connect you’re totally

welcome to reach out on Facebook just

look me up Dennis the more te mo RI and

I’m I was seeing on Facebook at least

once a week so I’m pretty easy to find

awesome awesome well I think you gave a

lot of great information a lot of value

was you’re very easy to talk to and

interestingly and have a lot of common

I’m sure and it’s just uh I think our

audience will get a lot of value out of

this because I know those people out

there and I get daily if not weekly

emails from people asking these very

questions so here it is folks you know

don’t just take it from me take it from

someone who’s living it and it’s fresh

into it and it seems some of the

challenges and some of the rewards and

hopefully you know I give you something

to think about before you and I wouldn’t

agree I mean if this is something you

think you want to do you gotta just do


yeah I I’ve always had this this this

way of thinking because I’ve lived in

several cities around the u.s. you know

I don’t know exactly how it’s gonna be

your house gonna turn out but if it

turns out I don’t like it

I can always get go back to go back home

the last place other lives and that I

found that the more you travel the more

you under understand what you want

because you’re just to get a little

philosophical we’re all kind of a

journey of self-discovery right try to

figure now what do we want out of life

what do we enjoy what do we not want so

we can find those things that we really

they make us happy as possible and being

here like I’ve said this pros and cons

at the same time is maybe if we

appreciate my life in the u.s. more

because you kind of especially was

listening to people in the digital nomad

community that are a lot of kind of like

anti us mm-hmm

is that you know the grass is not always

greener there there are going to be some

things you like but definitely things

you don’t know this trip has has kind of

opened up my world a bit but at the same

time maybe think you know what I do have

a pretty good we’re a ran United States

and it’s it’s better than I thought so

that it tell me with that appreciation

awesome awesome man I really want to

thank you for coming on the show a lot

of fun and for everybody else would back

again with another edition of the

podcast next week hopefully with

somebody as entertaining and delivering

as much value it

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