James Bowersox of Pindrop Clothing: 5 Things I Wish Someone Told Me When I First Became An Artist

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How tricky it is to identify your audience. Trying to identify who buys children’s clothing, and what audience will be receptive to your design was a very interesting task. Given the world-wide audience of the internet, the reach is wide, but we recognized the importance of niching down and doing targeting marketing.

As a part of our series about “5 Things I Wish Someone Told Me When I First Became An Artist” I had the pleasure of interviewing James Bowersox.

James Bowersox, founder of Pindrop Clothing, is a multifaceted and eccentric artist. James sought to bring art and a new dimension to kids’ fashion, so James and his children created Pindrop. He and his son design appeal straight from their home easel on the North Shore of Maui.

A lifelong drummer, music and art has always been prominent in his life. In addition to touring internationally and nationally for his own bands, he’s opened for Willy Nelson, Chicago, Steven Tyler, Taj Mahal, Mick Fleetwood, and so many more artists.

Thank you so much for doing this with us! Can you tell us the story of how you grew up?

I grew up in New Milford, CT and started playing drums at eight years old. I started working at The Texas Taco in Patterson, NY when I was 13 years old. It was a very eccentric Tex-Mex restaurant with an artist owner. Working there was a combination between serving tacos and art. That, along with my musical endeavors, created a very musical and artist environment in my teenage years. I was either playing music or working constantly, surrounded by art.

Can you share a story with us about what brought you to this specific career path?

I’ve always been an artist — a drummer, creator, producer, but recently took it to the easel. What started as creative passion turned to a conventional business.

All parents know this scene too well, days before the first day of school, we’re scrabbling to find new clothes that are affordable, fit properly, are season-appropriate…and most importantly, kids love. We’d spent the whole day shopping store to store, everything was either too babyish or the styles they liked were way too big. From style to size — kid’s clothes are lacking! I wanted to bang my head against the wall. I came home with a few basic t-shirts and shorts from Target and very disappointed kids. It was a massive failure.

So, my kids and I decided to start designing our own clothing. We took it upon ourselves to create fun, elevated, cool, and unique clothing for kids.

Can you tell us the most interesting story that happened to you since you began your career?

My children and I visited The Mint Museum in Charlotte NC. They gave free art kits to the children and on the way home, she drew a cat design. That design is now sold as “Kitty Cat Meow” on our website. I’m thrilled to see this passion for art come so naturally to my kids. I know the feeling well.

What are some of the most interesting or exciting projects you are working on now?

We’re currently working with Sean Michael Hower, Maui’s top videographer and photographer for many years to set up some lifestyle shoots at some pretty dope places in Hawaii.

Most importantly, we’re focusing on family art time to create more inspiration for new appeal designs.

Who are some of the most interesting people you have interacted with? What was that like? Do you have any stories?

As being a lifelong artist (musician), I’ve met many people and have had many interactions that have been greatly impactful in my development as an artist.

A great friend that comes to mind immediately is artist Eric Ernst. Being friends with Eric inspires me to become a better artist. He takes forms, shapes, and colors, mixed with musical and harmonic elements to conjure art. He plays with elements of representational imagery which inspires me to “think outside the box.”

Bill Kreutzmann played drums at my house in Hawaii. Getting to meet him and talk to him about his drumming experience with the Grateful Dead was enlightening and brought a new appreciation to their music.

Where do you draw inspiration from? Can you share a story about that?

My inspiration comes from a lifetime of creativity and imagination. Part of inspiration for me is constantly learning along with adventuring to new places and meeting new people. For example, I took my RV cross-country and stopped in Vegas along the way. I was taking the trash out when and this guy walked by and started talking. We both realized we were musicians and as we were talking, he told me he played trombone in Buddy Rich’s big band. My jaw dropped as Buddy Rich is one of my biggest musical inspirations. It’s these kinds of experiences that bring inspiration — not knowing what’s around the corner.

How have you used your success to bring goodness to the world?

Pindrop is a family-business. This brings so much goodness to our family, community and those who know our story. My son and daughter are very involved in the company-from design to photoshoot arrangements. Our mission is to create something for kids, by kids. Their friends are involved too, like modeling for skatepark photo shoots. Our kid-inclusive business model is what our brand is all about. Having fun and being able to learn with our kids along the way.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. How tricky it is to identify your audience. Trying to identify who buys children’s clothing, and what audience will be receptive to your design was a very interesting task. Given the world-wide audience of the internet, the reach is wide, but we recognized the importance of niching down and doing targeting marketing.
  2. Secondly, and playing off the first question, how hard it is to find your audience. Strategically putting your marketing dollars in the right place so you’re not burning through your money, is key. It’s very easy to want to try all sorts of different avenues, but you really must narrow it down to what is going to work for your audience.
  3. Sourcing the best materials and gauging price points that will make you profitable. Another part of knowing your audience, is knowing what their willing to spend and what quality they’re looking for. With anything, there’s a high-end, a low-end and everything in the middle. You have to find the sweet spot of what your audience is willing to spend.
  4. The amount of knowledge of technology you need to have in today’s marketplace. Moreso, how to navigate it (or find someone that can.) There are so many different programs, software, and strategy, you have to have a team to help guide you in the right direction as well as understand the other software and applications.
  5. The importance of PR and SEO. Getting your name out there is a very difficult thing every artist faces. I firsthand have seen the value of public relations and know that is a key ingredient. SEO is new to me but showing up on a search is everything.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would inspire a movement of creativity in youth. Art and creativity is all in us, especially kids. Kids are creative. They have out-of-the box ideas. To take these bold ideas and form a business would be powerful. I would love to see a movement of entrepreneurship and investment in the next generation. Why wait?

We have been blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she just might see this.

Tony Robbins. What he teaches has taught me to think and dream “bigger.” To meet him in person would be an incredible opportunity.

What is the best way our readers can follow you on social media?

IG @pindropclothing

This was very inspiring. Thank you so much for joining us!


James Bowersox of Pindrop Clothing: 5 Things I Wish Someone Told Me When I First Became An Artist was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.