Interview - Jeffrey Shaw

Leading National Authority of Self-Employment

Full Interview-


Below is a summary of my interview with self-employment expert, Jeffrey Shaw.  As a speaker, Jeffrey offers keynote presentations as well as personal coaching to help self-employed entrepreneurs reach their potential.  For the full interview, please enjoy the video.

Jeffrey Shaw was one of the preeminent portrait photographers in the United States, he had this fantastic on-location style and fine craftsmanship that made him the go-to photographer for families of C suite executives Anheuser Busch, Twitter, many others. He worked with supermodels, Stephanie Seymour, news anchors, Jim Nantz, David Bloom, sports icons like Tom Seaver. He’s worked with Wall Street executives, too many for me to mention, and his portraits have appeared on the Oprah show CBS News in People and O magazine, and they hang on the walls of Harvard University, and the Norman Vincent Peale center.
After 35 years of this exclusive clientele, Jeffrey decided to share his knowledge of business and branding and marketing to self employed people because here’s the big reveal. Jeffrey has never collected a paycheck in his life, he has always been self employed, and he has been teaching since then. He started the podcast creative warriors, which is now rebranded as a self employed life, but he is amongst the top 15% of all podcasts, and his TEDx Lincoln Square talk was later moved to, which I learned is about as rare as being hurt by your own toilet in your house. Pretty rare and unlikely.
I was great to have Jeffrey join me and share his wisdom. Being self-employed can feel like being in the bottom of a well. Jeffrey Shaw provided structure and direction.
Jeffrey’s entrepreneurial start was pretty basic. He sold eggs door to door. He grew up in is, what was then a small country town, a classic, farm land and party lines (sharing a phone number with five other families.) He had a very humble upbringing. His father was one of the first 90 employees of what was to become a new startup Computer Company, which became IBM. It was really weird situation of complete farm upbringing selling eggs door to door, but his father would bring home this technology and computers that was just unheard of at the time and talk about someday they wouldn’t need cash and it would be bars on merchandise. Meanwhile Jeffrey’s selling eggs door to door at 14 years old to make money, driving his mother’s Oldsmobile Cutlass Supreme, barely able to reach the gas pedal and see over the steering wheel the same time. His mom also owned a beauty parlor in town, a beauty parlor straight out of Steel Magnolias. Jeffrey would pack up cartons of eggs and the little old ladies would buy these eggs, so it was a thriving business.
Jeffrey’s early egg years helped him face his paralyzing shyness. Eventually he found that being in the spotlight on the stage is actually no different than being in a crowd at a cocktail party. You learn to manage the emotions of what that feels like. Jeffrey was an introverted person who actually craved the spotlight.
Ironically, Jeffrey chose being a photographer to pursue his life as a shy person, because back in the day, everything was done in a darkroom and behind the lens his shyness paid off because he was a masterful observer. His first “real” job as a photographer, was working for the FDR Roosevelt estate, printing images of their show horses. Next, in high school, he was winning national awards and traveling and then went off to photography school to pursue photography as a career. Ironically, photography, which he had chosen as a profession to hide, got Jeffrey into public speaking. He was nominated by the student body to be the student representative at graduation and speak in front of the entire graduating class, and their parents and their families. He didn’t know it at the time, but he was destined for the stage.
Along the way, Jeffrey also learned about connecting with audiences and customers. He wanted to be a highfalutin photographer, producing a really high value, and wanted to charge a lot of money for it. Unfortunately, the community was not willing to pay for it. Fundamentally he’d always understood that if you want to connect with someone, if you want to serve an audience, you have to understand them. It’s not about you. So he went to a store in New York City called Bergdorf Goodman which is super high end to learn about his target customer. He was a, completely out of place, 23 year old kid, wearing a then-cool Members Only jacket with 20 bucks in his pocket. Determined, he purchased the only thing in the store he could afford, a tiny votive candle. He asked for it to be gift wrapped because what was already obvious to him was presentation, had a lot to do with the lingo of this type of shopper.
The gift wrap woman supplied Jeffrey with the foundation of his customer education. She wrapped the candle in wads of tissue paper wads and wads of tissue paper. And then before she put it in the box, she stopped and said to Jeffrey, “don’t use any tape.” She went on to explain exactly the mindset of the Bergdorf Goodman customer. “They’re very particular before they give this as a gift, they’re going to untie the ribbon take off the box top unfold the tissue paper to make sure the candles are in perfect shape before they give it as a gift, refold the tissue paper, put the box back on or retie the ribbon. If you use tape, you would tear the tissue paper. And then it would be revealed that you had peeked in the package before you gave it.”
For young Jeffrey, this was mind blowing. He immediately knew that not price, but intrinsic value and product placement were even more important than what was actually being sold.
You have to understand how your ideal customers see themselves in the world, and match their lane. It’s all perception.
That became the root of what Jeffrey teaches. Jeffrey makes himself relatable and teaches small businesses to do the same. Good brands strategically actively connect with their market.
Jeffrey most enjoys speaking to self-employed people because that’s been his journey all along. Speaking at trade associations helps him reach professionals who are people who own their own business. He really understands their journey.
Self employment is different than any other connection with business because it’s personal. Whether your name is attached to the business or the force behind the business, it’s yours. Jeffrey has found that there is a direct correlation between personal development and level of success for the self employed. Owners actually have to first increase their own capacity. They have to believe they’re capable of more, remove blocks and limited thinking and think, in bigger ways. The self-employed can’t be limited by the humbleness of what they think they deserve. They also have to increase their capacity. Thinking bigger to prepare for business growth is the essence of Jeffrey’s new book The Self Employed Life, He talks about setting up systems up for the business to come, not the current business. Regarding mindset, Jeffrey says the self employed should “strive to be bored”. That thinking feels backwards for most entrepreneurs and self employed business owners. But striving to be bored actually helps create more time and space to bring more in. Like the old adage, then they’re working on the business instead of in the business. Spend time outside the business and see through your customers eyes.
Quick fire with Jeffrey Shaw:
LI: What’s your favorite word?
JEFFREY: Empathy. For all the reasons we’ve spoken about today.
LI: Do you have a favorite sound the sound?
JEFFREY: It’s so cliche but the sound of birds. I used to own a lot of canaries and I live in Miami now and we don’t have a lot of pretty birds like you’re not going to northeast. We have parrots that squawk, but. So to me it just, I’m so I just love the sound of a singing bird.
LI: Is there a movie character TV character that you can identify with?
JEFFREY: I have to go with Winnie the Pooh. He’s such an old soul that I love Winnie the Pooh quotes like I love Winnie the Pooh quotes. He’s such an old soul, and an innocent being, I actually think that’s who I am, I’m not quite as chunky yet. But and I do, I do wear pants.
LI: If you could take the play or be anyone or anything, what would you be for a day.
JEFFREY: , I’m going to be a dolphin for a day. Oh my gosh, it just looks like so much fun and freeing and, you know, being your mind I get to see dolphins swimming and playing and so for me it’s a dolphin
LI: What are you doing one year from today, right now?
JEFFREY: You know, I’m grateful for every moment I feel like I live in paradise and grateful for my life. But I do hope a year from now I’m enjoying a fruity alcoholic beverage somewhere. Feeling infinitely proud of the success of the Self Employed Life.