Jeffrey Shaw, widely recognized as an authoritative figure and champion for self-employed business owners, is highly regarded for his practical and hands-on approach to attaining success in both business and life. He has authored the books LINGO and The Self-Employed Life, hosts The Self-Employed Life podcast, and serves as the founder of the Self-Employed Business Institute.

Mark Struczewski 
You started selling eggs, door to door, at age 14. When I read that, I thought, How do you sell eggs door to door? And what happens if you break any eggs? Did it come out of your pocket?

Jeffrey Shaw  

Well, I’ll tell you what, it turns out it was the best beginning of entrepreneurship one could have because it there were so many learning lessons in it. 

For one, it was the bravest thing I could imagine doing because I was incredibly shy at that point in my life, like paralyzing shyness. So lesson number one for me, which I think holds true for me today and so many business owners, is that the benefits were greater than the fear. And the benefits were not the money but how I was growing. 

The best part about being self-employed is it’s like personal development on steroids. What I loved about the experience, despite the fear, was how I saw myself grow, how I saw myself stretching out of my comfort zone, and how I learned valuable business lessons.


As a solopreneur, I have a lot of freedom non-solopreneurs don’t understand. For example, I’m a huge English soccer fan. We call it soccer in the US, football to the rest of the world. When my team is on in the middle of the day in the middle of the week, I’m watching the game. It’s only two hours. So many people don’t understand how I can you do that. Well, I work before the game, and I work after the game. 

I don’t care if you’re in the corporate world, you’re self-employed, or you’re a solopreneur entrepreneur, everything’s got pros and cons. I believe that as a solopreneur or self-employed business person, you are unemployed every day you wake up. You agree with that?


Yeah. And it’s and that’s also the most satisfying part of it. Because I started selling eggs at such an early age, I’ve never had a traditional job. I’ve never received a paycheck. And believe me, many times through those 40 years, I had this fantasy that the grass was greener on the other side. And maybe I should get a traditional job too. My son once said to me, “Dad, you’re completely unemployable.” And he’s not wrong. I would be a horrible employee.


When we went through COVID, I kept working. I kept doing podcasts, training on Zoom, among other things, and people would ask me, “How are you adapting?” Well, I’ve been remote since 2005 so I didn’t miss a beat. People who were used to going into an office, they had to learn a new skill. But I think a lot of us who are already remote, we just kept on rockin’.


100%. I didn’t realize how challenging working remotely would be for so many people. How challenging it would be for people to not have the structure when they work remotely when it’s been my life all along. 


I actually read your book, LINGO: Discover Your Ideal Customer’s Secret Language and Make Your Business Irresistible, long before I knew you. But don’t give me a test because I probably would fail. (Laughing)


The concept of lingo is to learn to speak your ideal customer’s secret language.  Everyone has a secret language. And that lesson comes from the fact that while I ended up being a family portrait photographer for very affluent families, I didn’t come from Africa. I came from a lower middle class, at best in a small town in upstate New York where you would sell eggs. But how did I become then the go-to photographer for affluent families in the US? I did that because I took the time to understand their lingo. I understood clearly that I needed to work with an affluent clientele, not because I thought the roads were paved with gold.

If you’d asked me when I was 20 years old what a lot of money was, I don’t know that I could have defined it because I didn’t come from money. What was a lot of money when your family brought in just enough money to cover the bills that month? I don’t know; maybe $100,000 would have seemed like millions to me at that time. So I didn’t really have a reference point; I just knew that I needed to work with people who had discretionary income because I was struggling to get my business off the ground as a photographer, trying to serve people who didn’t have discretionary income because it’s a luxury item. 

So I realized I needed to find people who had discretionary income, who had the affordability to invest in photographs because it was important to them to have photographs as a memory and to hand down from generation to generation. So that to me meant affluent people. Well, how do you do that? Well, I took it upon myself to understand what made them tick. I started studying the behavior of affluent people in high-end stores in New York City. I would go to these high-end stores and high-end restaurants and I would study the customers, I would study what got their attention, I would study the structure of the stores. I wasn’t really interested in mimicking the brand. But I was interested in the psychology, the psychographic of affluent people, what made them tick what triggered them emotionally, and then replicated that in my photography business, so that as a principle, applies even more so today, that it’s the old adage or what’s become an old adage that people need to know like and trust you, it’s not even enough today. In order for you to penetrate a market, people have to feel like you get them. And after genuinely feeling like you get them, get their lifestyle, get their values, and that there’s an emotional connection, that will hold up and always has what made me stand out. It’s what enabled me to create a business in a world that I didn’t come from, and it’s what will always work best in business. 

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