We recently connected with Lorinda Van Newkirk and have shared our conversation below.

Lorinda, appreciate you joining us today. Can you tell us a story about a time you failed?

You never truly grow without experiencing failure. As painful as it may feel, failure is often the best teacher, revealing what needs to change and how one must evolve, whether personally or in business. In 2015, I faced the unexpected: I was fired from my own company, which I had built over the course of 13 years. As my business partner and the last seven employees stood there, we listened to the HR representative read through some legal jargon. Frankly, I don’t think I absorbed a single word.

Eighteen months prior, we had sold 60% of our company to a prominent clothing brand within the western industry. Little did we know that, a few months later, we would become just another acquisition destined for the chopping block. After 13 years filled with blood, sweat, stress, and tears, nothing could have prepared me for the exhilaration of having a high-profile CEO walk in and praise our brand. He envisioned it as the next big name in women’s western wear. Were there red flags? Perhaps. Was I overlooking certain signs? Maybe. Yet, I genuinely believed in this person and the team he brought on board—until the six-month mark, when my gut instinct whispered that this was not going to end the way I had hoped.

Would I go through it all again? I’m not entirely sure, but I would likely say yes; I am, after all, a risk-taker. Would I ask different questions? Absolutely. Would I perceive things differently? Without a doubt. I cherished our brand, Gypsy Soule. I loved what we had built together, what the brand represented, and the deep connection we had with our customers—they adored us just as much.

Gypsy Soule went out on top, and it will forever hold a special place in my heart. I firmly believe that God orchestrates events for a reason. While I cannot predict what Gypsy Soule might be today, I know that those who bought, wore, and supported our movement understand the emotion and passion behind the brand.

I can view this as one of my greatest failures, believing that others cared about what our brand stood for and the choices I made to nurture our small company. Alternatively, I can see it as one of the most profound journeys God has led me through. I have learned that I can build more brands, and customers will always light up when they hear the name Gypsy Soule. Nothing lasts forever, so I am grateful that I chose to confront failure head-on and say, “Bring it on.”

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I grew up surrounded by horses and the entrepreneurial spirit of my parents. My mom has always been a horse lover, while my dad is a cattleman, auctioneer, and hay broker. They’ve owned their own businesses for as long as I can remember, and they taught me the importance of grit and hustle. I was just eight years old when I started my first venture—a concession stand at my family’s arena.

Fashion has always been a huge part of my life. I used to collect every fashion magazine I could get my hands on. Looking back, I realize I was building a bridge between the Western world and mainstream fashion. I loved working in retail, especially in Western stores, and I really enjoyed the merchandising aspect. While the fashion side excited me, I found the thrill of sales just as captivating.

All of that experience led me to my current venture, Lucky Chuck Brand. With my sock company, I get to combine everything I love about entrepreneurship. I adore starting businesses, and fashion is a huge passion of mine, so Lucky Chuck is the perfect project for me. Everyone needs socks, and they’re such an affordable and accessible product. Plus, they can totally make a fashion statement! Being a true cowgirl I was so tired of BAD SOCKS so I decided I was going to make the perfect cowboy boot sock! Lucky Chuck Performance Boots Socks are the BEST!

My advice to anyone looking to follow their dreams is simple: identify what you love and hustle to make it happen. Grit and determination can take you anywhere you want to go. Building a network is also critical. The cowgirl network is something truly unique; once you experience it, you realize just how special it is. I genuinely care about the other women in our community, and that connection has helped me create a fantastic network.

We’d appreciate any insights you can share with us about selling a business.

Over my 30 years in the industry, I have successfully sold three companies. I have to say, finding the right buyers has never been an easy task, especially since I wasn’t actively putting my businesses on the market. Times were quite different back then. When I consult with brand and company owners, I always pose this critical question: “What is your endgame?” I want to know what they envision for their brand or company years down the line. Even if they have no intention of selling, I emphasize the importance of building a business with that possibility in mind. You never know what life may throw at you, and creating a brand or company that is ready for sale inherently encourages you to run your business more effectively.

One crucial piece of advice I always share in selling your company is to never owner-finance unless you’re prepared to take the business back—because nine times out of ten, you will end up doing just that. I also approach each aspect of a brand or company as a separate entity. For example, I break down the trademark, inventory, social media assets, and so on, allowing potential buyers to purchase all or parts of the business. This strategy offers multiple avenues for selling.

For me, every company and brand I create is always for sale. It’s business, not personal, but rest assured that the passion of my personality is infused into every venture I build.

We’d love to hear your thoughts about selling platforms like Amazon/Etsy vs selling on your own site.

Sell, sell, and sell anywhere you can!

When I started Lucky Chuck Brand in 2020, the landscape had changed significantly since Gypsy Soule ended in 2015. Coming from the retail and wholesale sides of the business, I remember a time when you had to choose one path and stick with it. Those days are behind us. Now, it’s the Wild West out there, especially with platforms like Amazon, where consumers expect instant access and the ability to return anything they want.

I sell Lucky Chuck Performance Socks to over 150 retail stores, on my own Lucky Chuck website, and on various other platforms. I always ensure that I never sell my products for less than my dealers or retailers do. They are my priority, and I want them to have the first opportunity to sell my products before I do.

Contact Info:

• Website: https://www.luckychuck.com
• Instagram: https://www.instagram.com/luckychuckbrand/
• Facebook: https://www.facebook.com/luckychuckbrand
• Youtube: https://www.youtube.com/@Luckychuckbrand
• Other: https://www.tiktok.com/@luckychuckbrand

Image Credits

Kiese & Co
https://www.kieseandco.com/