Freelance Survival Skills – How to Stay Alive and Thrive in the New Economy

April 8, 2018

[EP 42 The Blog Chronicles]
Steve Roller
In this straight to the point talk about the realities of freelancing, my long time friend and mentor Steve Roller sets out a few hard truths about who will actually make it in the ‘Wild West Gig Economy.’

I met Steve about six years ago at his Big Ideas Retreat in Vermont, since then I gained much knowledge from Steve which has helped me grow in my own online business.

I sat down and chatted with Steve Roller about his book – The Freelancer Manifesto – 11 Big Ideas To Stand Out And Thrive In The New Economy.

Any freelancer out there should definitely connect with Steve and even read his book, it will save you a lot of time and money if you’re not sure which direction to take.

Here are a few pointers from Steve’s book that will have you thinking about whether freelancing would be a lucrative online business for you or not and that freelancing is actually great fun at the same time as hard work and dedication.

In this Episode of The Blog Chronicles, Steve lays it all out in a realistic look at the realities of freelancing in a hard ass competitive world.

Here are some things you’ll discover in this interview…

* The Darkside of freelancing involves a lot of negativity and myths.

* Freelancing is not for everyone and if you have fallen under the spell that freelancing is all ‘fun in the sun and lazy days working from home?’ Think again. It’s definitely not a ‘get rich quick scheme’ and it’s definitely not for everyone.

* It takes hard work and dedication, sometimes juggling two jobs at a time because it’s not something with all the fringe benefits that a normal working job has.

* The biggest myth is that anyone can freelance.

* This is one of the 7 sacred cows that Steve slaughters and he exposes the truth about making it in the competitive world of the gig economy.

* This is all the more reason to read this great and inspiring book that turns all those myths into the reality that freelancing can be fun, lucrative and shows you how to stand out and get noticed.

* How the Gig Economy works and how you can use your skills to get it to work for you.

* Why being set to one specific niche is not that important.

* It’s more about developing your own personal brand and being authentic and transparent.

* Why keeping secrets in the freelance world is imperative to your survival and your success.

* How to use a Trade Mark to protect yourself… and so much more.

Join me, Matthew Kaboomis Loomis in this Episode of The Blog Chronicles as we explore the pains and joys of freelancing in the ‘Wild West Gig Economy.’


Please leave any comments you may have for Steve Roller in the comments box below.

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Steve Roller – Café


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Steve Roller Interview Transcript

( For those who enjoy reading.)


Matthew K Loomis: Hi Steve Roller,

Welcome to the Show!

Steve Roller: Hey Matthew,

Thanks for having me!

I’m honored to be here and I’m looking forward to doing this.

Thanks for having me!

Matthew K Loomis: It’s great to have you on the Show.

You know Steve, I’ve known you now for six years and I’m so grateful that I met you when I was starting out as a freelancer back I think it was six years ago now back in 2012, I think it was.

Steve Roller: Yip.

Matthew K Loomis: The personal coaching calls we did in 2013.

Your writing retreat that I attended in Vermont.

Those were all instrumental in helping me to grow and to get me to be better in this Wild West called ‘the gig economy.’

Steve Roller: Haha…

Matthew K Loomis: Or freelancing…

In fact, some advice you gave me in 2013 led one of my copywriting clients to become a business partner. So, I wanted to make sure I shared that because any freelancer out there who is not familiar with you Steve Roller, should be.

They need to visit your blog -Café or connect with you on Facebook.

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They should get your book that we are going to be talking about today.

So I just wanted to thank you for being such a giving person out there and providing a lot of hope and encouragement for freelancers.

Steve Roller: Matt, thank you for saying all that and I really appreciate it.

I remember the first time we met.

I know we met online, but I remember going to dinner at a nice Italian restaurant with you and talking and continuing our conversation with coaching calls and the retreat and stuff… But, no I really appreciate that.

That means a lot to me and I’m really glad that it had that effect and that you did something with it and it’s just been fun to watch your career take off since then too for a lot of reasons, a lot of things that you’re doing right.

It’s just been fun to watch you and I’m excited to see where you are today and where it’s all going. 

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We’ll be talking more about that too, but anyways, thanks for saying all that Matt.


Matthew K Loomis: Absolutely Steve!

Today we’re going to be talking about a book that you just wrote called:

The Freelancer Manifesto: 11 Big Ideas to Stand Out and Thrive in the New Economy

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Now, I’ve read this book and I will say I love the book. You really did a nice job on it Steve. It’s a fantastic book for anyone considering going into freelancing.

I like how, in the first part of the book, you call it the ‘Darkside’ of freelancing.

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Steve Roller: Haha…

Matthew K Loomis: What you do is you talk about the realities of freelancing the negatives… and you bust a lot of myths about freelancing that are out there.

Which was very refreshing because like you say in the book, you don’t hear a lot of people talking about the realities of working for yourself.

So let’s start with the darkside of freelancing.

Steve Roller: You’ve got a great voice for that Matthew.

Matthew K Loomis: Shooooowhooooshhhhh… Do the Darth Vader breathing….

Steve Roller: So what can I say?

What do you want to know or what do your listeners want to know about the darkside of freelancing?

Matthew K Loomis: I’ve put some questions together for you.

I’d like to start with, there are a lot of freelancers out there, you know they sit on the beach while they work and they get to work at home in their pajamas.

I know you love those two descriptions I just made about freelancing.

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Steve Roller: Haha…

Matthew K Loomis: Haha…

In all seriousness, those of us who have freelanced know that that’s not the reality!

That’s like poppycock!!!

But we know that that’s how marketers sell products that target freelancers. So why did you decide to get so real in your book?

Were you trying to blow some people out of the water, why did you decide to spend some time on these negative aspects of freelancing?

Steve Roller: Good question.

It wasn’t to blast anybody that’s promoting that side of things.

I have no problems with the fact that there are marketers out there that are promoting the freelance lifestyle and that it can be fun and they can write on the beach and all that stuff.

My purpose isn’t to say anything negative about them in general.

I guess what I really want Matt, is for people who are thinking about giving in to this, is to understand the realities. For me, I really was and I guess that whole aspect has really been oversold.

So the notion of the idea that anybody can do it, that it’s easy, that it’s fun, that it’s really lucrative right away and all this stuff.

Those things can happen. BUT, I want people to realize that I’m not trying to sell freelancing. I’m really not trying to sell it.

I’m trying to show people who have decided that they want to do this…


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‘Hey, here’s the reality and this is what it’s going to take!’

I guess I started out with that because I don’t see anybody else doing it.

Everybody is talking about the ‘fun’ and ‘lucrative’ and the ‘freedom’ aspects of it and those things can be there but I want people to know that if they are going to get into this that it’s going to take WORK.

I guess in a way I really do want to kind of scare people off because there are some people that are getting into this that have business doing it.

They are doing it for the wrong reasons they thinks it’s going to be real easy and they don’t know what it’s going to take to develop the skills and develop a marketing plan and to get clients and all this stuff.

So, I guess I started with that to combat the over selling of the ‘fun lifestyle’ and really to show people the reality. Obviously, from a book view point it was a contrary viewpoint that made for a good book.

So…All those reasons.

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What Kind Of  A Person Will Survive The ‘Wild West’ Gig Economy?

Matthew K Loomis: Good, good.

Yeah, I’m really glad that you did actually.

In fact in chapter four, you slay seven sacred cows of freelancing.

The first one that you butcher is the myth that anyone can succeed in freelancing.

Now, since we’re talking about the darkside here. First, tell us what kind of a person cannot succeed in freelancing? For some of us that are listening right now, if they are willing to be honest with themselves.

How can they take an honest look at their personality to determined that freelancing may NOT be right for them?

Steve Roller: I think if somebody works well under a lot of structure and order.

They like hierarchy and they like the typical company structure of jobs, and I’ve worked in that environment too, and if people crave that and they crave regular feedback on their work from somebody.

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They want recognition for their work, they want regular benchmark salary increases and promotions, they are really into the idea of titles. They like going to a place and feeling like they are getting some work done and then leaving their work and coming home and having a real life at home.

If someone likes all those things?

Then that person is probably NOT going to do well in the ‘freelance world.’

Because as freelancers –

– We don’t have order.

– We don’t have structure.

– We don’t get recognition from people very often.

– We don’t have anybody helping us.

– We don’t have a boss.

– We don’t have somewhere to go.

This is a small aspect and I don’t know if I really touch on this in the book, but some people like that idea of getting up, taking a shower, getting dressed, putting on nice clothes, getting into their car and driving to an office or driving to work to their job.

Feeling like ‘okay, that’s actually doing something.’

Some people can’t wrap their head around the idea that, ‘hey, I can walk down the hallway to my home office and that’s where I’m going to work.’

All those things, so if somebody needs more order, structure or recognition in their life and they need someone kind of telling them what to do?

Then this is NOT going to work for them.

Matthew K Loomis: I’m glad you covered that.

J-O-B. Right?

There’s that attitude out there and a lot of people use that and they bash job situations.

I recently heard Jon Acuff talk about these entrepreneurs that bash corporations and job situations are really doing something dumb, because here they are trying to scale a business and they are going to be hiring people, employees, but yet they are bashing jobs.

Jon Acuff – ACUFF.ME

Steve Roller:  I really don’t like that acronym.

For people who use the acronym ‘JOB’ for people? That just oversell the idea that if you’re working for someone else? If you’re working for man? If you’re working for corporate America? you’re just getting by you’re just never going to accomplish anything significant for yourself.

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I mean, ‘more power to them,’ but this country or our society would not operate without corporations or jobs, hierarchy and structure.

There is a lot to be said about having a regular job with a salary, with getting paid every two weeks with benefits and having a boss and having somewhere to go and being able to leave it.

All those things are great for the people that like that, for the people that want that and for different seasons in your life that might be a good fit.

This idea that ‘freelancing,’ that’s the dream that everybody wants and everybody should aspire to. That’s obviously what everybody would want to have. Why wouldn’t you want to have that lifestyle and the fun and the beach and all that stuff?

That’s a bunch of HOGWASH!

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There’s a lot to be said for regular jobs, so I just think it’s a matter of determining for yourself is that the best fit for me?

Or, maybe, should I look into this idea of working for myself?’

Then again, you might not necessarily be one type of person or the other your entire life, it may just be seasons that you’re going through. I went through seasons when my kids were smaller where I needed to have a job. I needed the bank balance, I needed to have the health insurance and all that kind of stuff.

Then at a certain point I transitioned out of that, but I wouldn’t have been able to function very well at a certain point in my life in the freelance world either and so it’s got to be the right timing too.

I Absolutely Recommend My Listeners Get Your Book Before Considering The Freelance World.

Matthew K Loomis: Absolutely!

There is so much more we can talk about on that.

Lets go ahead now and focus on those of us (Oh, that’s what I was going to say was,) that’s what I like about your book is how…If somebody is listening right now and they aren’t sure about freelancing.

Or they think they might want to do it yet they’re not sure. This is a really good book, Steve Rollers book – The Freelancer Manifesto – You should pick it up, because of the fact that he covers the realities of freelancing and it will really help you to decide whether freelancing is for you or not.

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Steve Roller: It could be the cheapest quickest way for people, it could actually save people.

I’m not exaggerating here it could save someone thousands or tens of thousands of dollars in going in the wrong direction.

Matthew K Loomis: Yeah. Absolutely!

Steve Roller: I do know people that thought that, ‘hey I’m tired of this.”

They were running away from their job and their boss and they thought ‘I hate my job and I hate what I’m doing right now, so I’m going to try this freelance thing.’

They did it and they spent an inordinate amount of money on courses and programs and coaches, conventions and all this stuff trying to build their business and it didn’t work out in the end anyway.

They went back to a job and they had spent a lot of money.

So, in some ways I want people to read this because for twenty bucks you might save yourself tens of thousands of dollars for going down the wrong path.

On the other-hand the ideas and the bright side of the book will, I think, if you apply them, will make you a lot of money too because I give people strategies and ideas to really stand out and thrive if this is the way they want to go.

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What Role Does The Gig Economy Or The New Economy Play In The World Today?

Matthew K Loomis: Exactly!

Now lets suppose that someone reads your book and they decide that freelancing is for them.

We’re going to shift into something that you talk a lot about in the book and you call it… Well, it’s a term that everyone is using now, it’s called ‘the gig economy’ or ‘the new economy.’

I understand what the gig economy is personally, but there are probably a lot of bloggers out there people aspiring to blog full time who are listening now.

They’re essentially looking at possible ways to become self-employed like a freelancer as a blogger.

They don’t realize that they will become a part of this economy yet.

So, I was wondering if you could help us understand what the gig economy is, this ‘new economy.

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How does it work today?

Steve Roller: I think there’s a lot of societal trends and things that led to this point.

What I take the gig economy to mean is that at this point in time it’s going to become an ever increasing part of our culture, is that, more and more people even if they do have a full-time job, more and more people are doing something on the side as well.

Part of that came from necessity as salaries have stagnated and as have needed to work more and the cost of living and inflation has gone up but salaries haven’t kept up with that.

Part of that is out of necessity.

I know a lot of people who have good paying regular full-time jobs, who for monetary reasons have chosen to also do something part-time.

I know people who are photographers or who are graphic designers. They have these skills that they have developed.

Maybe they always had them or maybe they developed them recently online.

Then they have these other skills that they can do for people in addition to their jobs. So they do them in addition to their jobs on weekends or in the evenings or stuff like that.

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Like some reports that I’ve read, this is a few years back, but there are a lot of reports that said by the year 2020 they estimate that 40% of all worker are going to be in some form of freelance work or working for themselves or self-employed.

I don’t know where we are today with that actual statistic, but I believe that we are probably getting close to it.

The gig economy could mean someone that has a full-time job but is just doing something on the side or somebody that’s in this full-time, but they’re doing different gigs for different people.

For example as a copywriter, I have a number of different clients and people are paying me to do a ‘gig’ a job or a project.

Sometimes it’s an on going thing where they need me every month, but sometimes it’s just a one time thing. It’s a gig they need it, I can provide it and they pay me for it.

In a way I think Matt, that this is a very efficient way for our economy to run. The people who need services only need to hire people when they actually need something and there’s all these people that do things.

For example I just had a logo done. I don’t have to hire a graphic designer or hire an agency or that, I just go online pay someone two hundred bucks to make me a logo and they make me a logo and I’m done with them, move on to somebody else then.

All these things all that to say…I don’t know but, I think we’ve been getting to this point for a long long time but it’s here to stay and because of the internet and being able to work online being able to work from anywhere and provide these skills and connecting buyers and sellers for all these services, it all combines for this gig economy, this new economy that we’re in.

I, for one think it’s a wonderful thing!

If you’re on either end, buying services or as a service provider making money in this gig economy, either way, I think it’s a good thing if you can position yourself right or you can stand out and make it work for you.

Matthew K Loomis: Definitely, we will get into the ‘how’ here in a little bit.

The gig economy is definitely here to stay for sure.

You see it as a good thing obviously, you said it’s wonderful.

‘The Gig Economy Is A Good Thing?’

Steve Roller: I do.

But I see so much from the press that it’s a ‘bad thing’.

It’s like ‘oh, jobs are going away and everybody’s doing a hustle online and doing these piddly little things online, ‘the gig economy’ there’s no benefits and people are being taken advantage of…..’ And all this stuff.

I’m like, ‘NO! THIS IS A GOOD THING!’ 

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Here’s another two examples, real quick. Uber is a prime example of the gig economy. It’s certainly a disruption for the taxi cab industry.

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The taxi cab industry doesn’t like the word, but Uber is great for people who want to get around. When my college aged son wants to get around, he doesn’t have a car, he just calls up Uber on his app on his phone.

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For people providing that service, the last time I used Uber I was actually out in Vermont at my retreat. I took an Uber from the airport to the inn.

The guy who picked me up was my age, a middle school English teacher, who has a good job. This was in October, so this was after he was done teaching for the day, he picked me up in his Uber and drove me.

He had told me that he had just gotten started two months before.

In two months as a middle school English teacher he had also found the time to give five hundred Uber rides around Burlington Vermont.

Matthew K Loomis: Wow!

Steve Roller: Whooohoooooo!!!!

So he’s making as much money and probably even more driving for Uber as an English teacher.

He loves it! 

This is the kind of thing people are just piecing together whatever works for them. So, I could give all kinds of examples, but that’s an easy example, people understand that.

Uber are a gig economy and I think it’s a great thing. It’s an efficient way for our economy to operate.

Matthew K Loomis: I’m a big fan of the gig economy too!

airbnb is another good example.

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Steve Roller: Yep!

Why Is Being Homed In On One Specific Niche Not That Important?

Matthew K Loomis: Alright Steve, let’s transition into another one of your sacred cows that you slaughter.

In your book, this is another sacred cow where people say, you have to focus on a specific niche to be successful.

Now, you do say that a narrow focus can be profitable,  you believe that it isn’t necessary.

So, why do you think that is?

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Steve Roller: Why do I think you don’t have to?

Matthew K Loomis: Yeah, why do you think that you don’t have to focus on a niche?

Steve Roller: I think it’s been over promoted.

Just like some other things that they’ve over promoted from that aspect. But, I think it’s been over promoted by, get this, the people who specialize in helping you find a niche.

But to answer your question why do you not need to. So, what you’re talking about…Okay, if you’re going to in our world of copywriting…In this book by the way, The Freelancer Manifesto, it’s speaking to all kinds of freelancers, not just copywriters.

In our example, let’s just say somebody is a copywriter the common, the standard advice would be, the only way you going to make it is if you specialize in a particular niche.

So, maybe you like pets and you like the whole world of pets, so you become a  pet copywriter.

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Well, that’s fine and that’s good, but the thing is no matter what niche you pick, you’re still competing with a lot of other copywriters who are also in that specialty.

Somehow, you also need to standout in a different way in terms of, to me I think there are two different ways I think that people can standout.

Without even picking out a subject niche, is to pick a service niche and specialize and get really good at one particular service. Maybe your thing is,  ‘hey, I’m really good at email marketing that’s going to be my thing, I’m really going to become an email master.’

Or, ‘I’m really good at writing video strips.’ Or whatever it might be.

So also focusing on a particular service.

The other way that I think is just as is important is standing out and specializing by creating what I call your personal brand.

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Really standing out in a number of different ways, by developing a strong personal brand where people know you for great things that you stand for and the way you present yourself.

The way you call yourself and your title, the look and…There’s a number of things, I’m not going to go off in that direction. But, there are a lot of different things that are incorporated into your different brand.

I just think that in this day and age with know how competitive everything is and having to stand out, that you really need to focus on building a brand to even more than just focusing on a particular niche.

Just the last thing I’ll say and that too, I’ve never picked a niche.

As a copywriter I’ve been full-time copywriting now for nine years and I’ve written in all kinds of areas.

I’ve written for the fitness industry and alternative health and financial and all kinds of different subject niches. Unless it’s a really highly technical area that you really need to become a master, I think the skills of copywriting or the art of persuasive writing applies across all different niches.

Personally, I find it more interesting too if I was writing about the same subject. and I hear this and one of the reasons I wrote the book was because for many years I’ve heard from copywriters who did so on a subject niche and they are like, ‘oh my gosh if I have to find out one more way to write about dog food I’m going to go berserk!’

Because they get tired about writing about the same thing and the same stuff.

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So, I find that one of the things about becoming a copywriter is just that it’s really interesting. You get to learn about different things all the time.

So, for all those reasons, that particular sacred cow.

Matthew K Loomis: I couldn’t agree with you more Steve.

I know Purina here in St. Louis has in house writers, so they’re all focused on dog topics.

I also realized after I read this part of your book, I was like, ‘you know, in house copy writers and ad agencies, they not niche specific, they’re writing for a wide variety of businesses.’

So, why are freelancers any different?

If you focus on the brand and ditch the niche, like our friend Katherine says, I think you’ll be better off too.

Steve Roller: That’s an interesting point.

You’re right, ad agencies writers, they’re writing for a different client. They’re writing all over, as they might be writing for Toyota one day, they might be writing about Yogurt the next day.

It’s more the creative process and the ability to come up with good ads, creative ads and good copy’s.

Matthew K Loomis: I actually agree with you.

If you have a niche and you find a good niche, that’s great. But, like you say in your book too, ‘if you find an untapped niche, don’t expect it to stay untapped for too long.’ Right?

Steve Roller: Exactly.

What Does ‘Staying Under The Radar’ Mean Specifically For Freelancers?

Matthew K Loomis: Now, let’s talk about a few points in part two of your book called – 11 Big Ideas To Overcome The Darkside Of Freelancing.

All eleven of these ideas are good by the way, all eleven are good ideas to help you succeed in freelancing.

We have time for one or two here today.

First of all, let’s talk about your idea to ‘stay under the radar’ I’ve been hearing you say that a lot now and again over the past six years, as long as I’ve known you.

You talk about ‘staying under the radar.’ What does that mean when you tell freelancers to stay under the radar?

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Steve Roller: What I mean by that Matt.

Often times, and I’m seeing this over and over, as you know I run this group called Copywriter Cafe. It’s a group for copywriters, but what I see happen a lot of the times is that people will come up with a new idea.

Maybe they will find somewhat of an untapped niche or a new service that a lot of people are talking about.

What people should be doing is focusing their efforts, their promotional efforts, their marketing efforts on just talking to their potential clients. They do that too, but what I find a lot of the times is these people will be so proud of their new found skill and their new found niche or their new found service that they landed and they’re excited about it and they’ll go mad about it.

But, what they do is they’ll advertise it and they’ll shout it from the rooftops and promote it and talk about it.

In groups like my Copywriter Cafe where it’s full of other copywriters, what a lot of times happens and not that people are trying to steal other people’s ideas.

Other people will see that and they’ll be like, ‘ah, wow, that is kind of a good idea!”

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What happens is that just instantly floods that market and so what that person has done by not talking about it and not staying under the radar, is that what they have instantly brought upon themselves is a lot of competition that they didn’t need to have.

This is especially true if you’re developing a new idea or come up with a new name for a business even. Or a new tagline or anything before you protect it, before you develop it fully and before you protect it. Say like for a intellectual property for example, say you come up with a really good tagline.

I met with a copywriter just a few days ago over in Atlanta and she came up with a great tagline for her business. She told me about it because I’m helping her, she hasn’t told anybody else about it and she took the extra step to actually register it with the U.S Patent and Trade Mark Office, as a trade mark or whatever you call it when you have a slogan.

She protected intellectual property wise, her slogan, so that’s what I mean by staying under the radar.

Wait until you have an idea or a business fully well developed before you tell other people about it going to your prospects and clients.

It’s not the people are out there to steal it but ideas are ideas.

If I come up with an good name or something and I throw it out there on a blog post or something and I don’t use it?

Well, it’s there for the taking someone else can use it. 

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Matthew K Loomis: You actually recommend going ahead and using the Trade Mark symbol even if you haven’t technically ‘Trade Marked’ it.


Steve Roller: I do.

I won’t get into the whole legal part of that right now.

Yeah, you can actually use that little TM symbol that stands for Trade Mark. You can use that on things, like say, I come up with a name for some thing, like I use I use it with the Big Ideas Retreat.

The Big Ideas Retreat™

October 14-17, 2018
The Strong House Inn
Vergennes, Vermont

Café Writer

I have used it for a few other things that I’ve coined and my domain name and stuff.

I haven’t taken the steps to hiring an intellectual property lawyer and paying for the actual Trade Mark number, but if you can see this at the actual Trade Mark and Patent Office website that they will allow you to use that TM symbol, if you have intentions of using it and if you are using it, especially if you have the domain name for it and all this stuff.

You can use it with the intention of using it.

Now, if you wanted to fully use it, then you would want to take that extra step of registering it. What it does is it shows people that you are serious about using it.

I think if you come up with something that’s elaborate and creative and somethings that’s kind of a neat idea, it kind of puts your stamp on it too and says,

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‘Hey, this is mine, I didn’t just grab this out of nowhere,’ 

‘I actually developed this name, I created this name!’


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How Does A Freelancer Develop Their Business And Protect Their Ideas?

Matthew K Loomis: I like that.

I think I’m going to start doing that too! 🙂

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Okay, Steve, so when it come to staying under the radar, how does a freelancer find a balance in keeping their ideas ‘under the radar’ and then on the other hand promoting themselves and marketing their skills to pull in new business?

‘Is balance even possible?

Steve Roller: I guess in this day and age where everything is online.

It’s kind of hard to stay quiet for too long and stay under the radar as it were. I would say, mainly, don’t be shouting it from the rooftops.

Don’t be telling you peers and your colleagues about it!

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Just focus completely on your audience that you want to serve and the chances are slim that they are going to do anything with it or use your idea.

But, if you are talking to colleagues and people that are in the same profession as you, there’s a very good chance that someone is going to use your idea or borrow it or steal it outright.

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I would say the only way to do this is to focus as much as you can on talking to your audience.

This is kind of an off-sided point that kind of relates to that, I see so many freelancers, all kinds, whether they’re graphic designers, copywriters or whatever, spending a lot of time online with people that are doing the same thing as them.

That’s not bad. I have a group myself of copywriters where I love the engagement and the participation.

I tell copywriters all the time…


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Hang out with your audience. Hang out with your prospects. We are not the ones paying your bills!

I think there’s just this idea that people and get validation for ideas, the comrade or the commiserating over bad clients.

Man, I think people in general need to stop spending so much time…

It’s almost like you were working in an office environment by the water-cooler talk, spending too much time over the water-cooler talking with you co-workers.

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In the virtual word as a freelancer, stop hanging out with other freelancers.

Hang out with you clients who are probably not hanging out on Facebook all day, you could be serving them. Go to them.

One last thing I’m saying about staying under the radar is that I’m still a big fan in this digital age and this digital marketing economy. I’m still a big fan of using print and direct mail, and direct mail is one way to avoid having your competitors see what you are doing with your adverts and your marketing.

For example if you were in the fitness industry and you were trying to reach all the personal trainers within a fifty-mile radius, you get a list of that.

You could easily compile a list of that and send those people things through the mail, that your competitors are never going to see, but as soon as you put a Facebook ad up, promoting your services to personal trainers or even having that on your website.

Everybody who competes with you is going to see that and it’s quiet easy to copy what you’re doing. 

Matthew K Loomis: A lot of people out there, I think, they’re usually not in marketing for copywriting.

But, they think direct mail is basically dead, they really couldn’t be more wrong. Right?

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Steve Roller: Oh, for sure!

I give examples of this all the time, but I mean at any given day, my mailbox is full. Just yesterday I had two things from local people, I got something from a tree-trimming service and a landscaping service and another one from an air conditioning service somewhere here in town. Obviously with summer coming up in a few months, people are thinking about that.

On any given day I get things from, realtors, insurance people and financial advisers and all kinds of service professionals and they wouldn’t be doing it if it wasn’t working.

Yeah, by all means, direct mail is not dead!

Matthew K Loomis: Yeah!

It’s NOT DEAD and it helps you SAY UNDER THE RADAR!

Steve Roller: YES!

Matthew K Loomis: Good stuff!

Okay, Steve, you mentioned a little while ago about personal branding. I’d like to talk for a minute about that.

Now, in chapter nine of The Freelancer Manifesto, the chapter is called – Branding Is The New Black, and it’s all about personal branding.

You had someone else write that chapter, and I hope I pronounce her name right, is it Desislava Dobreva?

Steve Roller: Yes, Desislava Dobreva.

Des is what she goes by, just DES, yes.

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That is the one chapter out of the twenty-one that I did not write. Go ahead, I’ll let you ask your question.

Matthew K Loomis: I was going to ask you.

Why you asked Ms. Dobreva to write that chapter for you?

Why do you consider her one of the best personal branding experts out there? Maybe you could share a couple of things which you learned from her.

Steve Roller: Well, this is not something that I just decided on a whim.

I actually had full intentions of actually writing this chapter myself.

But, complete transparency here, I had twenty chapters done, I had the introduction done, the forward was done, I had the back cover copy done. I had everything done with this book except for chapter nine.

Even though I’ve done it and I’ve done personal branding for myself, just out of instinct I have a good pretty strong personal brand with who I am and how people know me and how people perceive me and all that stuff.

I just didn’t quiet feel qualified to write that chapter.

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Desislava Dobreva – BADASS BRAND SQUAD

But, I wanted it in there because I feel it’s so important, that I got Des. I don’t know, only about a year or two ago, I think.

I discovered her online and she has this group called the Badass Brand Squad and we joke about it. She and I talked just the other week ago about it, and we kind of joke it about how we have such different styles. You know, she’s young, she’s hip, she’s attractive, she has an accent.

I have none of those things!

She has done a phenomenal job and she has courses on branding. I guess that what I have learned from her is a couple of things Matt, I truly do consider her to be one of the foremost experts out there on branding.

Not just for freelancers, but she also does consulting with corporations and stuff like this on their branding. So I feel strongly and I feel really good that I asked her to do this and I was honored that she did do it for me.

A couple of things that I’ve learned from her is that…And this is talked about a lot, but I don’t see it in action a lot is just the idea of being authentic and just being real.

Here’s the thing, we’re in a very competitive market place online. Everybody is shouting and screaming and trying to get noticed in this industry and this and that, but what I think what really gets you noticed is not the shouting and screaming and the big sales letters and the being loud and shouting higher and louder than anybody else.

It’s being authentic and being transparent and she does a really good job at that with her own brand and her own company. I think that that’s one thing that I was taking from her, I think that I was doing it already but it just stressed to me the importance of being real and letting people see who you are.

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I intertwine my personal life and my business life a lot so even clients know a lot about me and my personal life. They know about my kids and what they’re doing and they know that I like to travel, they know a lot of things about me.

I just try to be really real. I’m not one of these people that thinks you should keep business and personal stuff completely distinct and separate.

My life is kind of an open book online and so I think this whole idea of authenticity is a big part of it.

Then the idea of telling stories, this is something that we hear a lot from a lot of people and there’s people like Donald Miller who’s got the Building a StoryBrand and stuff like that a lot of bloggers that talk about the idea of a story.

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Donald Miller – STORYBRAND.COM

Des does this really well herself with social media posts and her email marketing and on her website, but just telling stories. People will listen to stories more than they will listen to a sales pitch or a sales letter or a promotion.

So if you can find a way to incorporate stories into your brand, and again, this goes back to just telling people who you are and why you do what you do.

I don’t know if that answered your question Matt, but I’m just really big on this idea of branding and I just think that Des does a great job of it and I’ve learned some great things from her.

Just for anybody listening, just to let you know, Desislava Dobreva, on Facebook, Badass Brand Squad. Just to let you know Matt, and our listeners, she and I are going to be teaming up on something later this year or early 2019 like a live event.

It’s going to be unlike anything that either of us has ever done and unlike anything you’ve seen out there.

It’s going to be really interesting because we both have different audiences. We acknowledge the fact that she and I are both very different people but we’ve had this really interesting connection and we really are in sync on a lot of things and it’s going to be fun and it’s going to be super powerful too.

So I’ll be talking about that more in the future.

Matthew K Loomis: It sounds intriguing Steve!

For those of who who are listening, there’s links in THE SHOW NOTES to Desi’s website and her social media connections.

I think I am friends with her on Facebook, but I haven’t yet dove in to her content, so now I really want to do that.

Steve Roller: Check it out when you get a chance for sure.

Eleven Mental Building Blocks -The Freelancer Manifesto

Matthew K Loomis: Okay, fantastic!

Steve, let’s go to part three of your book now which is called – Your Abundant Future.

You talk about taking your business to level eleven, you list Eleven ‘Mental Building Blocks To Lead A Prosperous Freelancing Career.’

Can you elaborate on this a little bit, maybe talk a little bit about these ‘mental building blocks’ that will help freelancers to actually prosper?

Steve Roller: Yeah, let me think Matt, it’s been a while since I read that chapter, haha…

I’m trying to think what these ‘Eleven Building Blocks’ are okay, yeah,yeah,yeah…

So first of all, ask me a question.

What was the final question again there?

Matthew K Loomis: If you could just touch on one or two of the eleven, give us a few tips on how a freelancer can really turn it up to eleven and succeed.

Steve Roller: So, this Level Eleven.

For those of you who don’t know the movie Level Eleven Spinal Tap, look it up online, go to YouTube look up Level Eleven This Is Spinal Tap. This is the movie clip that that comes from, but it comes from the movie the term, so I won’t go into that.

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But, the idea is taking it past level ten. Most thing go to level ten, you know what I’m talking about, the thing is the volume goes up to level ten, but we want to take it up to level eleven. So, it’s a metaphor, but the idea is going beyond what most people do and what the typical person is going to do.

Really making that one of your goals to just get to this Level Eleven of being super successful.

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Too many people kind of dip their toe in the water, and they kind of try this out and they hope for, you know, ‘I hope I can make it, I hope I can make it as much as with my full-time job?’ Or maybe the big goal is to make six figures on this.

My thinking on this is just the idea that we should be thinking kind of bigger than the norm.

One of the things that I put in there is, so, I have these Eleven Mental Building Blocks, one of them is just to make this decision to reach this level eleven.

Another one them is what I call just not putting a premium om leisure time. Personally, I like having fun. I like travelling and stuff, but I’ve never understood this, ‘working for the weekend’ mindset.

You know, the drag and the 9 to 5 and Monday through Friday and finally it’s, ‘Oh, thank God it’s Friday’ and the dreaded Monday and all this stuff.

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Honestly, I can’t stand that attitude!

I think a lot of the time this is why people gravitate towards being a freelancer and doing their own thing. They don’t like doing the 9 to 5 thing.

I think whether it’s the 9 to 5 or the freelance world, you should be doing something you enjoy.

I mean, it took me a while to land into this land of copywriting, but once I did, I just knew I was enthralled with it. I love it! I wouldn’t go as far as to say I would do it if I wasn’t getting paid, but I love what I’m doing.

I know in some way in some capacity, writing and copywriting will be a part of my life for the rest of my life and I enjoy it!

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Going back to this idea of not putting a premium on leisure time, I think we put too much time, in our culture I think this is an American thing too, but the living for the weekend and just you work hard, the weekends are just for play and then you’re back to work.

I don’t know, my life is just kind of intertwined. I enjoy spending time on a Saturday doing my work and doing that.

Sometimes I go out on Saturday night, I go to Starbucks and work for a few hours, people think I’m kind of a strange person for that.

To me that’s just, I like doing things different to most people.

That kind of goes into another one of these Eleven Points and I’ll finish with this one. It’s just adopting a contrarian view-point of work.

I did mention this in the book, but my good friend Ed Eslow say’s,

‘I want to live my life so that you can’t tell whether I’m working or playing.’

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That just kind of goes along with, why can’t work be fun?

I went away for ten weeks. I went to Ecuador for ten weeks. People asked me, ‘well. what did you see and what did you do?’ Well, actually I stayed in a studio apartment and I walked to a cafe everyday and I wrote my book, that’s what I did.

They’re like, ‘Oh, that sounds kind of boring.’ I’m like, ‘no, it’s fun, I enjoyed it!’ I did a few other things too.

Most people associate work with drudgery and if you’re doing something that you don’t like, I suppose it is.

I think it’s important to find work that you really do love and then it’s not going to be this way, and that’s another reason why I think this whole gig economy is great, because even if you are working a full-time job and you have to do it because you need the money and you need the benefits and all this stuff.

Why not find something that you really enjoy and that you can really get into and sink your teeth into. Maybe make a transition and do on the side, but little by little transition into that full-time.

One last one that I think is important is, I think this was number seven in there of those Eleven Mental Building Blocks to get to number eleven is, I think it’s really important to study and learn from rich people.

I’m going to go off on this and go off on a rant and things, but there is just such an attitude in our country of kind of despising and thinking that wealthy people somehow got that way by ill-begotten means.

Either they con people or they get it off the backs of people that are working for them, or they inherited their wealth or somehow they stumbled upon it. They got rich somehow and there must be something wrong about it, they’re not the people to emulate and admire and stuff like this…

I say, that that is all wrong and somehow we should find a way to study and learn from people who have accumulated wealth and built successful businesses and do everything we can to find out what they did and how they did it and emulate them.

I would go as so far as to say try to surround yourself with people who either are wealthy or aspire to be wealthy. I, for the most part hang out with people who are wealthy or people who want to get there.

That’s not the most important thing in life, but I think there’s nothing wrong with wanting to be really wealthy. I think we should learn from people who are.

Matthew K Loomis: The book is called, THE FREELANCER MANIFESTO.

It’s a great read by Steve Roller.

If you are interested in getting this book and I think you should, I’ve got links to Steve’s Amazon author page down in THE SHOW NOTES.

Now, I want to close this question with one other question that I think the listeners will find fascinating, is that okay Steve?

Steve Roller: Yeah. Absolutely!

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Artificial Intelligence Versus Freelancers In The Gig Economy.

Matthew K Loomis: So Steve, as an authority on self-employment, I would like to get your thoughts on the future of the gig economy.

Particularly, the rise of robotics and artificial intelligence. For the aspiring writers out there, designers, web developers, actually pretty much any line of work is fair game.

Should we be concerned about AI limiting our opportunities for work?

What is your take on the future of freelancing?

Steve Roller: Man! Than is an excellent question!

That came out of the blue because I wasn’t expecting it.

It’s a great question and it should be on everybody’s mind.

First of all, the future of the gig economy.

Number one, the gig economy is not going away I think in the future, it’s not going to be the norm to have a regular job. The people like us who are in the gig economy doing our thing and working here and there.

Working wherever we want and working for this client here and that client there and piecing together a life and a business.

That is going to be the norm and the typical 9 to 5 is not going to be so common anymore.

So I think the gig economy is here to stay. Again, going back to what I said earlier, I think it’s a very efficient, effective, productive way to run the economy.

As far as where it’s going with, so as with your question with  all this stuff like AI and robotics and stuff like this, are you asking Matt, are some of us depending on what we do, are some of us and our skills maybe in danger of being replaced, is that what you’re kind of asking?

Matthew K Loomis: I’m just asking what you think, you know.

You and I are in the copywriting field and I know some copywriters maybe a little concerned that a robot could end up writing as well as a human.

What do you think, that we could survive, or who will survive?

Steve Roller: Well, here is what I will tell you.

I think it is a legitimate concern.

I think a lot of the players in our field, talking about writers, content writers, even bloggers and copywriters, all of those.

I think it is a legitimate concern and I think five – ten years from now, right now, people might not like me saying this, but I think there’s a lot of writers.

There certainly is a demand, but really Matt, content writing, copywriting all this stuff is in danger of becoming a commodity. There are AI programs and stuff there is an AI that can write copy as good as any human.

They have proven this.

They can write good headlines and stuff, based on, and I don’t know how all this stuff works, but a company could not have to hire a human and just get it from other ways, so it is in danger of becoming a commodity.

Now, who’s going to last, who’s going to survive and how are they going to do it?

I think there’s always going to be a creative class, so I think as much as, yeah, you can come up with a lot of stuff through AI, but the people who have good ideas and can think about…I think where we are going to be able to bring value to our clients is if, and this is something that I talk about all the time, you’ve heard me say this before Matt.

So, if I’m a copywriter, but instead of just delivering copy to people, if I can be known as an idea generator and a problem solver.

That has value and that is something that, nobody can replicate my brain, the ideas that I come up with the way I think and the ideas that I can convey to my clients and help them build their business with. 

So, if we can be giving our clients ideas, and constantly generating ideas and interesting ways of looking at things and new angles, new thoughts and new ideas, new concepts. That’s what’s going to be important.

I think some of the commoditized stuff, the content writing like writing an article, yeah, you could get a machine to write an article as good as like humans.

But, if you’re being creative and you’re giving your clients ideas and you’re helping them solve problems, that’s the way that everybody should be thinking about their business or whatever kind of freelancer.

I’m not just talking writers and copywriters here.

Whatever your business is, be thinking of yourself as someone who can help your clients think of new ideas, that they wouldn’t have thought of without you and help them solve whatever their business challenges or whatever their business problems are.

On top of all that, if you are genuinely a likable person, I can’t stress this enough either, but this is something that you can learn. You can’t take a book, you can’t take a program on it, but if you are just a genuinely likable person and you have a good way of developing repore with people, connecting with people.

Those people are going to rule the world!

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Those people are going to rule the gig economy! 

That’s what it takes, being likable, generating ideas, solving problems then you don’t have to worry about all that other stuff, but you do have to keep you eye on things. Adapt with the time and maybe your services that you provide will change with the times.

Be focused on those three things and I think we’ll be okay.

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Get Connected With Steve Roller On Social Media.

Matthew K Loomis: We finished with a BANG!

Steve, it’s been fantastic having you on THE BLOG CHRONICLES today!

Where can people connect with you on social media?

Steve Roller: Three places.

  • My website is – Cafewriter Dot Com

  • On Facebook I have a lively, helpful, friendly group for writers, freelancers and copywriters, called – The Copywriter Cafe

  • On Amazon you can find my author page Steve Roller, look for the book, or The Freelancer Manifesto.

Matthew K Loomis: You can find all the links to the places you just mentioned in THE SHOW NOTES.

Steve, I saw your book, that you already have your second book underway, so when that book comes out, I’d like to have you back on THE BLOG CHRONICLES.

Steve Roller: I’d love to be back.

It’s started, it’s not very far but I always have the next one in mind so, I’ll love to come back.

Thank you for having me and I hope that everyone listening has got some good ideas from this today and if there’s anything that I can help you with Matt in the future let me know.

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The Show Notes

Steve Roller – Cafe Writer

Steve Roller – Cafe Writer – Blog

The Freelancer Manifesto: 11 Big Ideas to Stand Out and Thrive in the New Economy

Steve Roller – Big Ideas Retreat – Cafe Writer

Steve Roller – Facebook

Steve Roller – Twitter

Steve Roller – Linkedin

Jon Acuff – ACUFF.ME

U.S Patent and Trade Mark Office

Desislava Dobreva – Badass Branding For Online Entrepreneurs

Desislava Dobreva – Badass Brand Squad

Desislava Dobreva – My Exclusive Branding Community – Facebook

Donald Miller – StoryBrand Marketing Workshop

Level Eleven – This Is SpinalTap – YouTube

Be sure to stay tuned for the next informative episode of  THE BLOG CHRONICLES!

Image result for Images of Matthew Kaboomis Loomis

Matthew Kaboomis Loomis is the owner of Build Your Own Blog.

Follow him on Facebook and Twitter.


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  1. Ryan Biddulph says:    •   2 years Author

    Hi Matthew and Steve,

    Amen to this. Love your takes on freelancing.

    Yes Matthew could make a wonderful Darth Vader, voice over wise. Melodic, deep voice. I sound like a bratty church mouse with a Northern NJ accent on podcasts LOL.

    I go so in depth to sharing practical tips and blogging tips to show folks whether freelancing or selling eBooks or doing anything online; if you want to Blog From Paradise and have home office views of the South Pacific – yes, as I do this split second in Opotiki New Zealand it is a jaw-dropping view – give years of your life to freelancing or blogging or…both.

    I did not say to work hard for years. I said to give your life to blogging for years. Beyond finding spiritual nourishment and of course, taking care of your body and being with fam, most of your time will be spent writing, building bonds and plum giving your life to freelancing. No other way exists. If you want to live a life with some stunning home office views.

    If someone appears to be getting a bunch, goodness knows they gave a bunch for many years to reach that place.

    Thanks guys 🙂


  2. Steve Roller says:    •   2 years

    Great perspective, Ryan. I agree wholeheartedly.

    The people who seemingly have it all almost always have an underlying story of years of perseverance.

    I’d love to see your view in Opotiki. New Zealand is on my list.

    Thanks for listening. Hope to connect with you somewhere, online or Down Under or perhaps in my second home office neighborhood of Quito, Ecuador someday.

    Until then, best wishes with everything you’re doing, Ryan. Cheers.

  3. Annamarie says:    •   2 years

    I agree, with Ryan and I bet a million other people do. Every man should have such a sopportive and calm voice. I wish you could do the voice over on my books, Mathew, you should consiidder it. 😊.
    I loved your interview and am certainly getting this book from Amazon.
    With school holidays starting on the weekend, internet access will be down or hard to get and I’llI have time to read and write.
    After Doing all that needs doing this week, of course.
    love and Blessings ❤️😊

    1. Matthew Loomis says:    •   2 years Author

      I’ll email you, Annamarie! 🙂

      Talk soon,


    2. Steve Roller says:    •   2 years

      Thanks for listening, Annamarie, and thanks for getting my book! If you have any questions as you’re reading it, or if there’s anything I can help you with, feel free to reach out anytime.

      Best wishes with everything you’re doing.

  4. Jerry Huckfeldt says:    •   2 years

    Hi, I listened to your interview with Steve Roller.

    First, he seems like a humble man and that is good. I liked how he talked about regular jobs being ok. It was actually kind of refreshing to hear about the negative or the reality of working online.

    It takes time and work. Too many adds say about all you have to do is sign up and watch the money roll in. The idea of wanting to have a job you like and not work for the weekend is great if you are able to achieve it. But it won’t turn out that way for everyone.

    Talking about not concentrating on one niche was interesting too.

    Thanks for your emails,


    1. Matthew Loomis says:    •   2 years Author

      Hi Jerry,

      Thanks for letting me know how much you enjoyed this one.

      Yep, regular jobs are okay. I’m backing away from that marketing approach. I did a little of that myself a few years ago. Not everyone is meant to be a business owner. I’m done putting jobs down because most businesses need a few employees.

      The topic of niches is one I could spend a whole episode talking about. Hmmm, maybe I should do that? 🙂

      Thanks again for dropping by, Jerry, and I hope you will join the conversation again.


    2. Steve Roller says:    •   2 years


      Thanks for your comments, I appreciate it.

      Let me know if there’s ever anything I can help you with.

  5. Mandy says:    •   2 years

    Hi Steve and Matt,
    Thank you for the intelligent input here 🙂
    Steve, I love the way you sound, like you have no stress and you put the listeners at ease because you made that dark side literally sound like there was definitely a light at the end of the tunnel, for whoever thought there was no hope.
    Freelancing is wonderful because it’s really like a hobby that you can use your skills and talent for, at the same time as making money and getting even better at what you do.

    Matt I love your voice, you would make a wonderfully exciting storyteller and it’s such a pleasure to listen to you.
    Thank you for your service to people like me.


    1. Matthew Loomis says:    •   2 years Author

      Awe, thank you, Mandy, you are the best. 🙂 You’re a wonderful transcriptionist.

      Steve is definitely a light out there people should “run to.” 🙂

      I’m really happy with this interview. More freelancers need to hear it.


  6. Mandy van Zyl says:    •   2 years Author

    Thank you Matt,
    I love doing these transcriptions, I have learnt so much from all your wonderful guests, most of all I love the fact that I get to use my creative side to compliment their stories.

    Thank God for the wonderful people out there that each have a talent to help others, what I have learnt is most certainly this, that each person has something that we need and we have something that they need. In a big way we are all connected and we can all relate to each other, no one is excluded in the telling of the stories that make us human and make us humble and through this we can share our experiences and help those in need.

    This is a wonderful Show and I know that you will reach a lot of people with The Blog Chronicles stories, which will aide people in helping them get that confidence to blog and tell their stories which in turn will build hope for others.

    God bless!

  7. Steve Roller says:    •   2 years

    Thanks, Mandy! It was great to do a show, and I know Matt appreciates the work you do on the transcriptions. On this one, I do, too. 🙂

    Yes, we’re all connected in a strange, wonderful way on the internet, especially through blogs and podcasts like this. I love it.

    Hope you’re doing well. If there’s ever anything I can help you with, let me know.

  8. Mandy van Zyl says:    •   2 years Author

    Thanks Steve, all the best in everything you do!

  9. Henry Smith says:    •   2 years

    Thank you, Steve and Matthew, for this informative article about Freelancer. I have agreed with you that every day many newcomers entered and make changing for us to maintain our position.

  10. Patti Smith says:    •   1 year

    Wow! That really boosted my morale today. It’s been a rough couple of weeks getting my blog designed. My BIG take-away: Be Real!! Thank you, Matthew and Steve!!. The Blog Chronicles are the BEST!!