Joshua Boswell’s dream was a great marriage with a big family while making tons of money in a home business. Today, Joshua’s copywriting business more than supports his extra-large family while giving him abundant quality time with his wife and 11 children.

In today’s episode, Joshua talks about his journey from barely scraping by to living his dream… and shares steps that you can take to turn writing into your own desired lifestyle, too.

Listen and discover:

  • How to recognize the lies you tell yourself and overcome self-doubt.
  • Why client-focus is your real game-changer.
  • Your untouchable value (no amount of money can ever change this).
  • Why you don’t need many clients to make a lot of money.
  • Joshua’s Endless Profit Matrix (write down this easy way to get more projects from your clients!).
  • The importance of picking and sticking to one marketing direction.

Important Links & Mentions

Joshua Boswell’s Copywriter Marketer Website

Copywriter Marketer Membership
(Formerly CM Secret as mentioned in this interview with Joshua Boswell)

Bob Bly has also been a featured guest on Solopreneur Success and was the first guest trainer for the Solopreneur Success Connections community. Patron members can get the recordings and bonuses from that on the Past Training Recordings page in the Members area.

SSP014 Success as a Freelance Copywriter and Author with Bob Bly

American Writers & Artists Institute (AWAI)

Also be sure to listen to my interview with Katie Yeakle & Rebecca Matter from AWAI in Solopreneur Success episode 20!

SSP020 Copywriting: The Power of Persuasive Writing with Katie Yeakle & Rebecca Matter

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Solopreneur Success™ Transcript

SSP044 Copywriter Marketing with Joshua Boswell

Joshua Boswell:

I had it in my head, at the time, that my value as a husband and a father was totally tied up with the amount of money I made. So, if I made more money, my wife would love me, and my children would love me. If I didn’t make any money, I was a complete failure, and they wouldn’t love me.

Steve Coombes:

You’re listening to Joshua Boswell, whose success story as the loving head of a large family and highly profitable copywriting business personally inspired me to pursue the field of copywriting nearly 15 years ago. Soon after, I met Joshua who became both a friend and business mentor to me. I credit much of my early business success to Joshua so definitely listen up to this episode because Joshua is today’s guest on Solopreneur Success.


Welcome to the Solopreneur Success podcast, where successful business owners gather to share true stories and sound advice to help you start and grow your own solopreneur business. Come soar with us and design the life you love. Now, here’s your host, Steve Coombes.


Hello, solopreneurs. Today, I’m excited to interview my friend and my personal mentor, Joshua Boswell. Now, I’m going to let Joshua share his story in just a minute, but I do want to share a little background so you can understand how Joshua came to be a person that I looked up to as a newbie freelance copywriter, because, like me, Joshua is the dad of a large home-schooled family, he’s a person of faith whose faith is important to him, and when I first learned of Joshua, he was already a full-time writer, providing a great income for his family, just like I wanted to do.

I had read about Joshua’s story, the same way I’m going to ask him to share with you in a moment, and I really, really wanted to meet him. It’s not like I expected to see him at the first live writer’s event I ever attended, that was 2007 AWAI copywriting bootcamp down in Delray Beach, FL. As soon as I spotted Joshua, this guy’s standing innocently in the back of the room with his wife, and I accosted him and introduced myself like a big fanboy, and just said, “Joshua, I’ve got to meet you.” I knew a lot of big names in the industry, but, for me, Joshua Boswell was my writing hero.

Long story short, Joshua very graciously, personally, helped me get started on my own successful writing journey. I’m thrilled to finally have him on as a featured guest of Solopreneur Success™ to share how writers can turn from a starving artist life to living a life that’s fulfilled, well-paying, and a lot of fun. So, Joshua, welcome to the show.


Thank you so very much. I remember that day when you jump on me. I was so pleased to have a fanboy. I just thought, “here’s a fellow soul that I could relate to.” It was a great day, and we’ve got a great friendship ever since. I have got to tell you, I have been just amazed at your journey and what you’ve done, and how you reached out and built your business, and connected the dots, and now you’re doing this show. You just did some great things, so it’s an absolute pleasure to watch you and to see your growth and to see what you’ve done. I’ve got to say one other thing about you.

One of the things that I pride the most about you is your incredible devotion to your family, which, of course, is near and dear to my heart. I just wanted to say hat’s off to you for that. You’ve been able to hold together your family, prioritize them, and still build your business, and make money. A lot of people just can’t do what you’ve done. So, congratulations. That’s really cool.


Well, thank you, Joshua, you are definitely an inspiration to me. You haven’t always had it easy, though. You’ve certainly had your struggles early-on, and you’ve been a businessperson for a long time. A lot of people that I know, in our circle of writers, might know your story, but there’s a lot of people listening to the show right now who have no idea who is Joshua Boswell, what is the story? It’s an amazing story. Could you maybe walk us through what led you into writing, and what were you coming out of when that all started? What took place?


Yeah, that’s a great question. I’m going to start back before I got into business, before I was married, before anything. To understand my story, you really have to go back to 1992/93, when I was in the Netherlands, I lived over there for a couple years as a missionary for my church, and toward the end the two-year service, I’m walking down the road with my buddy and he turned to me and said, “when you go back to the states, where do you want to be when you grow up?” In that moment, I had this flashback to a childhood memory when I was 11 years old, and we were driving this Chrysler LeBaron station wagon. [inaudible] I don’t know if you remember the old Chrysler LeBaron. They had the jump seats on the back, and you could sit back and look out the back window. It’s pretty cool.

My mom pulled over to the side of the road and run into my dad. [inaudible] He’d been hit by a drunk driver and so he was missing one leg, he had one fake leg. He was hauling on the road. About an hour before, they had gotten into a huge fight and my dad stormed out of the house. Eventually, my mom, after crying hysterically for hours, picked herself up off the floor and said, “we’re going to find your father.” So, we all filed into the station wagon, driving around all these neighbourhoods, finally found him down on this busy street. She jumped out of the car, and, for just this brief moment, I thought they were going to kiss and make up, but they didn’t. They just started like hammer and nail, right there on the side of the road.

I just remember, as an eleven-year-old kid in the background, I didn’t understand the parents, I didn’t understand what they were going through, what they were doing as adults, and all the complexities now that I understand so much better, what my dad was going through and my mom was going through. I didn’t understand all that, but in that moment, the one thing that I wanted more than anything else was my dad. I just remember, as an eleven-year-old kid, my head was just screaming over and over again “I just want my daddy.” I said, “dad, just get back in the car. I just want my daddy.” I don’t know how long they sat on the side of the road fighting with each other. Finally, my dad spun on his heels, walk down the street about 150, 200 yards to this T-intersection that was there. He took a right-hand turn. There was a McDonald’s sitting right on that side of the road, and I watched him walk behind McDonald’s and then disappear from view. My mom sat outside for a few minutes, got back in the car, cried for a few more minutes, started the car, we drove down to that intersection, and she took a left-hand turn, and that was the last time I saw my dad for over five years. During a really critical period of time.

I tell you that story because if we fast-forward back to the Netherlands, I’m on the side of the road and my buddy’s asking me where I want to be when I grow up, and I remember that moment in time and I thought to myself, “all I want to be when I grow up is a great husband and a great father.” I just want to be a husband and I want to be a daddy. This formulated this itch inside my mind, inside my heart, this idea that I had about the kind of life that I wanted to live. Basically, it can be summed up like this: I wanted to be able to work from home so I could spend time with my children. Well, first of all, I wanted to find an amazing woman to marry. I wanted to have a whole bunch of children, I wanted to work from home, and I wanted to make enough money and have time to be able spend that money. I wanted that time and money equation.

As I came back from Europe, I tried a lot of things. I jumped into Amway, did multilevel marketing for about five years, and poured my whole heart and soul into that. I dreamed that I was going to be Amway king in all of North America. That didn’t quite work out, but I adjusted from that and started another business, where I tried to do some public speaking and sales training, and that didn’t work out that great.

Then my brother and a friend of mine, three of us started a company where we did technology stuff. We built websites. These are websites in the late 90s that were database-driven which, then, was crazy because all websites were static. These were data driven. It was very innovative. That company collapsed through a series of really odd events that were tied up with September 11.

Then, from there, I went into politics and worked on doing fundraising for political campaigns, and that went okay. Then I went into building a company doing fundraising for non-profits, and this is really where my story of becoming a writer picks up. This is a good ten years into my marriage, so if you notice the pattern – my dream was I really wanted to have a great marriage, I wanted to have a large family, at this point we had six children, but I wanted to work from home, which I had done through all those different iterations of stuff, and I wanted to make a whole bunch of money, which I hadn’t done.

We scraped by for ten years, then we finally had opportunities to do this other project and build these fundraising for non-profit companies across the United States. I put that company together and I borrowed a bunch of money. In fact, I got an investor who gave me a loan, basically an investment, but I signed a personal guarantee that I would pay him back all the money. I remember the day I took the agreement to an attorney, and he said “I would never ever sign this. This is a really bad idea,” because it put me in debt $200,000 of personal liability. When you’re not making that much money, you’re scraping by, and the family system that I came from was, “if you make $50,000 a year, you are rich.” That was the family dynamic that I came from. So, here I was signing away $200,000 to this investor and, I won’t tell you all the details, but that company collapsed.

In the wake of that, it left me a couple hundred thousand dollars in debt, liable to a bunch of employees for their last day, and all kinds of crazy stuff. I went into a pretty heavy tailspin, and it was right about that time, that was in December of 2004. In the spring of 2005, I got a letter from AWAI that said I could retire that year and still make more than most doctors.

Now, I was particularly vulnerable. I was really interested in some opportunity that I can still find or fulfil my dream of living at home or working at home that made me a whole bunch of money and be able to have time and money to spend with my family, and here’s this letter saying I can retire and make more than most doctors. Oh, baby. I did by due diligence, I did my research, but that was the first time I ever heard that there was actually an organized industry called copywriting. Even in all the circles that I had run in before, I’d never even heard of that term before. I heard about writing fundraising letters and some other stuff, but copywriting? Hadn’t heard of it.

We can go back to whatever details you want in here, but the long and the short of it is I fell into that world pretty hard. That was in April. In June of that year, 2005, I went to an event with a guy named Bob Bly. Bob ended up becoming one of my mentors. I was big Bob fanboy. If Bob was writing about this thing, if Bob was doing it, I was there.

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