Interview with a Barefoot Writer: Joshua Boswell

“I get to dictate every minute of every day. I decide what I do. Nobody puts anything on my schedule unless I’m asking for it to be there. I’m complete master over my time and circumstances.”
— Joshua Boswell, Six-Figure Copywriter and Marketing Consultant


Joshua Boswell

Ten years ago, Joshua Boswell was in a tough spot. Dead broke and with six young kids to feed, he’d tried and failed at a string of businesses that didn’t pan out.
He’s also a talented marketer, best-selling au­thor, business-launcher, word-innovator, and for­mer journalist.

Then one day, he got a letter from AWAI about something called copywriting. That moment was a turning point in his life. As he tells it, he knew something great was getting ready to happen … and boy, did it ever.

These days, Joshua’s professional writing busi­ness earns him a multi-six-figure income. His cli­ent list is peppered with Fortune 500 companies and includes esteemed names like Corel, Sony, Google, Microsoft, Verizon, Nightingale-Conant, and St. Jude Children’s Research Hospital.

Not only has he established himself as a go-to direct-response copywriter, he’s also a respected speaker, marketing consultant, and coach.

Joshua’s enthusiasm for the writer’s life is topped only by his great love for his family, including his wife Margie and their 11 children. Read on to learn how Joshua took his copywriting business from nothing to six-figures in his very first year, and how this lifestyle has made it possible for him to build his dream life.

You were bankrupt and had six children be­fore you found copywriting. How did you have the courage to start this new venture when you had so much at stake?

Here’s the thing … from a very young age, my whole focus and goal in life was to be a great hus­band and a great dad. That’s all I ever aspired to do.

Making money is just the fuel to reach that dream. It’s just a means to an end, not an ending of itself. So when I was completely broke, I woke up one day, and I realized I was really hurting my family and I was limiting opportunities.

It was no fun. It’s a situation where you can’t just randomly go play and do cool stuff with your kids, especially when they’re worried about what’s for dinner next and whether the power is going to get shut off. Those were dampers on the party, right?

So I realized that my main purpose and goal in life was not being fulfilled and money was the pre­dominant problem stopping me from being able to live that dream.

Back up for a second. You’re a smart guy. How did you get to that point in the first place?

The primary reason I was in that mess was be­cause I tried lots of other things to fulfill that goal. The main goal was always the same. I wanted a big family. I wanted to be able to work from home so I could spend time with my family, and I wanted to make a lot of money so I could have the flexibility to do lots of cool stuff and give my kids opportunities so they could become amaz­ing adults.

That led to a bunch of different businesses, and I did not succeed at most of those. When copy­writing came along, it was like, oh, wait a minute. Here’s an opportunity that’s just stellar. I can work from home, I can have big clients, I can get paid a lot, I can do stuff in a short amount of time so I can spend time with family. It just fit all of my criteria.

Did it take a lot of courage to dive in and study to become a copywriter?

It was more than courage to get out and do it. It was, “Here is finally the vehicle that is actually go­ing to make this happen for me, make my dream become reality.” So I was super excited to just dive in and tackle it because I really believed it was the solution I had been looking for.

You went on to build a valuable client list with some really big names. How’d you do it?

When I first got started, I approached clients that were small. They paid low, they didn’t treat me with a lot of respect. I realized that if I kept pursu­ing that path, I was going to end up spending a ton of time making very little money and always being slightly aggravated that I wasn’t getting the respect and income I wanted.

So I made a decision. I said it’s got to be just as easy or hard, however you want to look at it, to close big clients as it is to close small clients, and I literally one day just flipped the switch and said, “Okay, I’m not going to even approach smaller cli­ents anymore. I’m just going to go after industry giants.”

I started marketing myself to different people, and the result was that it was true. It took just as much effort and strategy to land projects with Google and Verizon and Sony and General Mo­tors, as it did to land projects with small clients.

One of the reasons is because with the bigger clients, you don’t actually do stuff for the bigger clients. You do stuff for small divisions within the bigger clients. So I found out it’s the same thing working for a big client as a little client; the only difference is, the bigger client is attached to a huge organization with the pockets to pay you much better and give you a lot more respect.

How do you land these bigger clients?

It might sound like a trite thing, but really, I just ask. A lot of it was lucky breaks. But I was also just very persistent.

For example, my first big client was Corel. They were the first major Fortune 500 company that I did projects for. This might scare some people off, but it took me seven months of calling and following up and sending emails and touching base with them to finally get to the right decision maker, and when I did, they gave me a trial proj­ect. They loved that, and then they hired me for multiple other projects after that.

It’s a great lesson on the payoff in patience.

Sure. I used that contact with Corel to leverage a lot of the other clients I landed. Sony was also worth the wait. When I originally contacted Sony, they said they really wanted to work with me, but they run on a different fiscal year. The fiscal year started, at the time, in April.

So the marketing guru is like, “I spent my budget for this year, but when the new budget comes out, I’ve got allocations for a freelance writer and we’ll do it.” That was in November, so I waited from November to April to write for Sony. But it was worth the wait, because over the next 18 months, I collected over $100,000 in fees for mul­tiple projects from Sony.

Why have you pursued speaking opportuni­ties on top of all the great copywriting proj­ects you get?

There are three answers there. First of all, I love people. I love being around people. So when I get to go speak, then I get to spend time with people. I get to look in their eyes, shake their hands, hear their stories. I like that speaking helps create instant change and long-term results.

I also love helping peo­ple change their lives and get results right away, and I love setting them up for a long-term win. That’s the second thing.

The third thing is not quite as romantic, but it really comes down to finances. When I speak, it sets me up as an expert. People recognize me as an expert, and I land clients quicker and easier that way because I’m recognized as somebody who knows what they’re talking about and en­dorsed by the organizations I speak for. It’s just an awesome positioning tool.

Not everybody has the ability to speak or to speak well. It happens to be one of the skill sets I have, so I leverage it.

When you’re not off speaking, what are the pros and cons of working from home?

For me, the vast majority of it are pros. I’ve learned how to manage it effectively. Meaning my fam­ily knows there are certain non-negotiable work times.

This is really, really important. There has to be a period during the day when you can be pro­ductive and get stuff done. Especially writing or when I create speeches or do my video or what­ever, there is absolutely a rhythm and a zone that needs to be gotten into in order to produce and deliver.

Distractions and phone calls and children coming in are an interruption to that and it throws me off. That’s one of the cons to working from home, is that you potentially have somebody who can just feel okay about stepping into your office at any time and throwing you off track.

The pros are that there’s an enormously awesome lifestyle to it. There’s a great amount of flexibil­ity in terms of my schedule. I get to dictate every minute of every day. I decide what I do. Nobody puts anything on my schedule unless I’m asking for it to be there. I’m complete master over my time and circumstances.

You said you have nonnegotiable working stretches. What does your basic work sched­ule look like?

I average between 20 and 30 hours a week of work in my office. I’m an early riser, so I get up between 4:30 and 5:30 every day, depending on how late I went to bed.

The first hour or two of my morning usually con­sists of scripture study, devotional, journal writ­ing, and planning. Just all of the deep thinking that’s really important to me when the house is totally quiet and I am restful and at my best.

Then I have breakfast with the family. We do a morning devotional scripture study as a family, and then by 8:00 or 9:00, I dive into whatever projects I’ve got going.

How do you keep all your projects organized?

Each day, I have a list of six things, and there’s a strategy there. I usually make the list the night be­fore — things I’m going to get done. I come into my office, look at project number one, and I get hammering on it.

Usually I’ll do that between 9:00 and noon or so. At around noon-ish — and again, I’m saying a lot of ish-es because it’s not super structured. It’s one of the things I love about working at home. It doesn’t have to be structured. I’m not a super structured guy and I love the flexibility.

There’s a pool here close by. That’s my way to work out and exercise and play with the kids, so usually the whole family goes over there around noon-ish. We’ll swim for an hour or so.

If there are afternoon things to do, I’ll check some emails, follow up on a few phone calls, maybe do some coaching calls for another hour or two.

Then by 3:00 or 4:00, I’m done. It’s time to go play with the family some more. I do a lot of volunteer stuff for church, so in the evenings, we’ll do some project together or run off somewhere in the community and do service projects.

How often do you take a day off work?

Thursdays, all day Thursday, I basically take off work. We’ve got a number of family activities and church activities we schedule and that pretty much consumes Thursdays.

Usually my afternoons on Friday are off-limits. What I mean by off-limits is usually we get back from the pool around 1:00 or so and I may do a half-hour of tinkering around and clearing the radar and checking email and setting my priority list for the weekend and then it’s time with family and then date night.

Margie and I go out on a date every week and it’s not a “Let’s go out for an hour” kind of date, it’s usually more like “Let’s go spend the evening to­gether somewhere for three or four or five hours.” We like it that way, and the kids get to play, and we get some romance time and it’s pretty cool.

Sounds lovely. Do you travel much as a family?

That’s a major part of our family DNA. Traveling together is one of my dreams. I always wanted to travel a lot as a family. We consistently, at least once a month for at least two or three days, go somewhere as a family.

Sometimes there’s a regional travel trip so we’re flying somewhere. We went to see the capitol building. Our one son’s been super excited about astronomy lately. There are some big observato­ries here in the Midwest, so we might go hit one of those.

Whatever it is, we just consistently go do that. And then at least once a quarter, Margie and I, just the two of us, will go take off and go do something and that’s usually anywhere from three days to 10 days.

Then three, four times a year we’ll do a bigger family trip. Last year, we spent a week in Florida with another week before that in Georgia. We also, as a family, went back West. Earlier that year, we did a U.S. history tour. We went all up and down the East Coast and looked at U.S. his­tory sites and did some cool home school stuff with the family. We’ve been to Mexico. Some of us went to Europe together. We’ve been down through the Caribbean and Bahamas, up through Canada. I think we are currently at 41 of the 50 states we’ve been to as a family.

Incredible. Do you work while you’re on vaca­tion or stay far away from email?

Most of the time, I send my clients blackout dates. We have a lot of loose structure in day-to-day liv­ing, but on the macro scale, the calendar scale, there’s a lot of structure.

For example, we’re planning a big mission service trip out to Central America this year, and I already told all my clients, look, I’m going to be gone for three weeks, so just don’t even think about giving me anything then. We’re just gone, sorry.

I will typically do that at the beginning of each year and I’ll signal them that these weeks and this time frame are all blackout times. They like the advance notice, and if projects come up last min­ute and there’s something there that I can do on the road, then I will. It doesn’t bother me at all to crank out an email or project or do a conference call or whatever. I’m cool with it, the family is cool with it.

I hear you speak Dutch. How did that come about?

I’m fluent in it. I’m mostly fluent in writing, totally fluent in conversation. That came about when I was 19, I went to serve a mission for my church. I was assigned to the Netherlands, so I lived there for two years.

Since then, over the years, I’ve had a number of clients that are in the Netherlands or in Germany, where they have some connection to the Neth­erlands, so I’ve done a bunch of translation work. I’ve done projects over there. I’ve done a lot of consulting, both onsite and from home here.

It’s not like an extremely widely spoken language, but it has given us a great opportunity to go over there on occasion. I’ve taken Margie and some of the kids. Lot of fun.

Great example of leveraging something from your past.

There’s a big market for Americanizing stuff. A lot of European companies and Asian companies, they want to break into the U.S. market, and the problem is that a lot of the materials are trans­lated directly, which always comes out screwy. I mean it’s English, but it’s not. They missed all the cultural innuendos and the tone and what’s cur­rent and all that stuff. So I’ve done tons of transla­tion projects.

I’ve done projects for British companies where I’ve Americanized their copy so it sells well in the U.S. I’ve done it for German companies, I’ve done it for Dutch companies. That’s a cool market. I don’t talk about it much, but it’s made me a lot of money.

Let’s talk about the other ways you’ve made money. What’s your favorite self-marketing method?

I have a standard answer on any marketing meth­ods. I’ll talk about specifically what I’ve done, but before I talk about that, I don’t want the answer to be skewed to imply “That’s what Joshua did so that’s what’s right for me,” because that’s not the case.

The best marketing method for anybody who wants to be a copywriter is the marketing meth­od they will consistently do.

There’s an unlimited number of marketing meth­ods out there, and I can point out to you million­aires and people that made hundreds of thou­sands of dollars in each of those by focusing on them. I know people who’ve done it in social media, I know people who’ve done it with cold-calling, I know people who’ve done it with emails, and the list goes on.

But the best marketing method is the one you’ll actually do.

Which marketing method works best for you?

When I started out, the very first thing I did to mar­ket myself is I approached my known network, so people that I already knew, and I told them that I was in copywriting and was a copywriter and looking for companies to provide services for.

That immediately netted me my first client. My very first client was a PR firm out of Washington, D.C. They put me on a very modest retainer to do a lot of writing for them, but it was a start. That came from just a word-of-mouth connection from some people I knew.

The second thing I did to get started was I used Bob Bly’s self-marketing letter and referral cards and I mailed those out. That probably would have been really effective for me if I would have stuck with it, but I ran out of money for postage and printing.

That’s where cold-calling comes in?

Social media basically didn’t exist 10 years ago and I didn’t have an email list, and I needed mon­ey right away, so I didn’t have time to build myself into an expert.

My solution was to suck it up, and you might be surprised at this, but I was completely terrified of getting on the phone and making cold calls. I don’t think I’m any different from anybody else out there. The prospect of it was not enjoyable to me at all.

As extroverted as I am, it scared me to death. I spent the first three days practicing to the wall, just trying to get myself to say the words because I was so nervous. That’s how I got started.

For the first year, really for the first 18 months, my entire marketing program consisted of doing one- to three-hours of cold calls a day. That was it. I just picked up the phone, called, and did it over and over and over again.

But it was totally worth it, right?

Within the first year and a half, I’d landed some really big clients. At that point, the second part of the equation kicked in: I had an awesome client list. I had a great reputation.

Basically from the eight-and-a-half years since, I’ve ridden on the coattails of that fundamen­tal establishment where I got clients and I go to meetings and I’ll do coaching and I’ll just make connections. Essentially, I’m a known expert in a couple of different fields, so I get contacts and re­ferrals and that’s the method that I teach.

There’s a very systematic way to do that. I hap­pened to come about it through cold-calling, but there are other ways to build yourself as an expert and have the project flow just keep continuing.

You keep the ball rolling.

Totally. Yeah, we go from one project to another to another. Now that doesn’t last forever with all of them, but some of them it does and has, so it’s a great marketing method.

And it saves a lot of time since you know your clients’ needs and they know your process.

They’re just people, and as people, they’re sus­ceptible to the persuasion tactics that we use to sell people when we write. They’re all people. Build the relationship, develop the rapport. It’s very important.

Who inspires you?

I have a whole world of speakers that inspire me from a motivational perspective. Some of the more popular ones: Anthony Robbins and Zig Zi­glar and Bob Proctor and Dennis Whaley. Dennis Whaley was one of the first motivational speak­ers I heard that totally transformed how I thought about life.

Bob Bly obviously has been a mentor and a hero to me for just many, many years. Another speaker that super inspires me, that I love spending time with is Rebecca Matter of AWAI. She’s great.

What about books that have influenced you?

By far my single favorite set of books is the scrip­tures. Far and away my faith, my religion, my connection to God and to spiritual powers and unseen things in life has been very real and very important to me. It’s a huge driver to who I am and what I do. Nobody can really understand my story and who I am without understanding that connection.

Outside of that there are three books that have been incredibly impactful to me and provided guiding principles for me.

The first one is a book called As a Man Thinketh by James Allen. It’s short, it’s a quick read, it’s incred­ibly powerful. The second book is a book called Leadership and Self-Perception. The author of it is the Arbinger Institute. Amazing book. Transfor­mational. The third one is Think and Grow Rich, which has also had a transformational impact in my life.

What’s your favorite ice cream flavor?

Oh, man, I’m a huge fan of stuff with caramel and nuts, especially if it’s got caramel laced through it. I’m also a big, big berry fan. Anything with mul­tiple berries, strawberries, blueberries, blackber­ries, raspberries. I’m a big berry fan.

Conversely, most people don’t know and think I’m really weird, but I am not a chocolate fan. So the chocolate ice cream, chocolate bars, choco­late candy … meh. Give me a berry any day, I’m much happier.

Healthier, too. Are you an animal person?

Another thing where I get booed by the crowd is I’m not a big home-pet kind of a person. We don’t have dogs or cats. I really love eagles for lots of different reasons. I’m a big fan of eagles in terms of an animal.

Interestingly enough, and this will sound funny, I’m also big goat fan. I love goats. There’s a reason behind it. My connection with goats is connected to my family. When our son Hiram was young, he had enormous reflux and allergy problems, and we couldn’t find anything that he could keep down.

He had thrive issues. Somebody recommended goat milk, so we bought goat milk, $10 a gallon, and gave it to him. He loved it and it settled well and it was great. Then I found out that I could feed a goat and milk a goat for about $8 a month.

No kidding?

I can get a gallon a day out of a good nanny, so we went into the goat business and I found out later that it is also awesome at teaching kids how to work. They had to take care of the animal and they had to go out and do the milking, so it played into my whole role as a father. So I have a fond place in my heart for goats.

This lunar year is the Year of Goat. It’s your year.

It is my year. Eagles and goats, there you go.

Let’s say at the next AWAI event you have to dress up in a costume. What would you come as?

Well, you can’t really dress up as a daddy and a husband, but that would be my first pick. My sec­ond pick would be an astronaut. I have always had an intense passion for space and galaxy and the physics that are associated with it and always dreamed of going to outer space, so I’d show up as an astronaut.

I’ll expect that at the next Bootcamp.

I’m going to NASA to ask if I can pick up a suit.

What kinds of Glicken have you gotten from clients?

One of the very first major Glicken things I did is I wrote a bunch of stuff for a client and then they asked me to speak. I talked to them about coming to speak and I said, “Can I bring my family?”

The event was in Florida and I’d always dreamed — going back to my love affair with space — of going to the Kennedy Space Center and getting as close to the shuttle launch pad as I could and taking my family there.

So as part of the deal, we had an all-expense-paid trip to Florida and we flew down there. We went on a cruise as a family. We got off the cruise boat. We spent several days at Kennedy Space Center. We did all the cool up close, personal tours and behind-the-scene tours.

Then we rented a van. We drove all over Florida. We went to the Everglades. We went to a place called Lion Country Safari.

Then we chartered a boat and went snorkeling. And, all except for the chartered boat, all of it was covered by the client as a note of appreciation for some of the things I had done.

For me, that was awesome, and that’s really started a trend. Any time I travel for consulting or speaking, part of my deal is that Margie comes with me and the client pays for it, or Margie or some of the children. Sometimes it’s the whole family.

Talk about some great insight into the possi­bilities of professional writing!

These are the kind of perks you just don’t get in Corporate America, not that I know of. So it’s a to­tal fulfillment of some of my dreams and desires, and it’s just been an awesome experience.

The trips to Europe have all been paid for by a cli­ent. Every one of them.

What would we find in your refrigerator right now?

You would find a lot of leftovers. I’m terrible at making too much food. Right now you’d find a big thing of stir fry, some chow mien noodles. You’d find a lot of fruit and berries. Not surprising, right? We make a lot of shakes around here, a lot of smoothies.

You’d find leftover pancakes, because we love pancakes. We make all of our pancakes fresh. We grind the flour. Love that. We’re big fish people, so you’d find lots of salmon and cod and other kinds of fish and shrimp in there. You’d find lots of fruits and vegetables because we try to eat re­ally healthy.

Lots of brain food.

If you open up the freezer, of course you’d find an ample supply of ice cream.

With caramel, right?

Chocolate for the rest of the family; berries and caramel stuff for me.

You’re living the good life.

We like ice cream.

In the news story of your life, what would the headline say?

The headline would say “World’s Happiest Father and Husband Achieves His Dreams.”

Beautiful. Let’s wrap up with your top advice for aspiring writers.

I’m a big believer in the law of the harvest. I think the thing about nature is it reveals to us a lot of secrets about success. One of the things I’ve noticed is that in nature, things don’t happen overnight, but when they do happen, they happen in great abundance.

So if I go out into my garden and I plant cucumber plants or tomato plants, it takes a while. It’s going to require some work to get that plant to grow. I’ve got to nurture it and make sure it has plenty of water.

It’s a little bit of work to get it there, but over time, gradu­ally, a little bit every day, bit by bit, cell by cell, the chloroform starts to form, the leaf starts to grow, the stem starts to grow, all that stuff.

At some point, it starts to produce fruit. Anybody that’s growing cucumbers or to­matoes knows that as long as the weather stays warm, those vine plants will just keep producing over and over and over again.

It’s like, me, I did an hour to three hours of phone calls every day for a year and a half, and it’s pro­duced eight-and-a-half years of six-figure income with my income going up every year.

Well, I had to put the work in at the beginning. Essentially, I planted the orchard, right? I planted the fruit trees. Whatever analogy you want to use, I planted something that’s produced over and over again for me, but I had to be patient to get to that harvest point.

The story repeats itself, that when you consis­tently do the right things, even if it’s a little bit, eventually it produces a harvest for you.

This interview was previously published in the March, 2015 issue of Barefoot Writer. To read more interviews from fellow Barefoot Writers be sure to checkout The Barefoot Writer's Club.

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Published: December 25, 2017

1 Response to “Interview with a Barefoot Writer: Joshua Boswell”

  1. Great interview... Thank you for the motivation and insight. And the humor.

    ***possible edit error. The first section appears to switch from 'he' to 'she' - - it doesn't seem to make sense.

    AnneWindsorDecember 29, 2017 at 12:11 pm


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