Today we’d like to introduce you to Cliff Lunsford.
Hi Cliff, please kick things off for us with an introduction to yourself and your story.
Nearly 30 years ago, at just 18 years old, I started my first business out of my parents’ garage. It was an outdoor camping & outdoor supply internet business where I stocked products and also drop shipped from suppliers. The business grew to over a million dollars in sales and taught me a lot about e-commerce and business, but like many others, it was hit hard during the 2008 market crash.
Since then, I’ve started multiple businesses and side hustles, experiencing both successes and failures along the way. One quote that has always stuck with me comes from Michael Jordan:
“I’ve failed over and over and over again in my life. And that is why I succeed.”
That quote resonates deeply with me because no matter what life or business has thrown my way, I’ve always gotten back up, dusted myself off, and kept pushing forward.
That mindset still holds true today. Even in success, there are difficult days in business that can knock you down. Wins, losses, and lessons happen almost every single day. Entrepreneurship is a grind, but it’s one that’s absolutely worth it.
In 2024, we started Ole Boy, an outdoor lifestyle apparel brand, and the growth has been incredible. In a short time, we’ve grown to serve more than 30,000 retail customers and partnered with over 300 retail locations across the country.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Anything worthwhile comes with a cost — usually blood, sweat, and tears. Literally.
When building a startup, especially in the early days, you do most of the heavy lifting yourself or with a very small team. That’s exactly how we built Ole Boy. It was built through long hours, sacrifice, love, support, and a willingness to do whatever needed to be done — no matter the time of day or the day of the week.
Like any business, we face daily, weekly, and monthly challenges. Some days test you more than others. But through it all, we persevere. We keep showing up, keep pushing forward, and keep believing in what we’re building.
That grit, determination, and passion are what continue to drive Ole Boy forward every single day. And we’re successful at that.
Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Ole Boy is more than just an apparel brand — it’s a lifestyle brand built around the outdoors, family, faith, hard work, and southern roots. We created Ole Boy for people who love hunting, fishing, time outdoors, and the simple things in life. Our goal has always been to build a brand that people are proud to wear and truly connect with.
What sets us apart is that Ole Boy was built from the ground up by a small team with a hands-on mentality. We’ve poured countless hours into every aspect of the business, from product design and customer service to packing orders and building relationships with our retail partners. Everything we do comes from a genuine passion for the outdoor lifestyle and the people who live it every day.
We specialize in high-quality outdoor-inspired apparel and accessories that combine comfort, style, and authenticity. From our graphic tees and performance fishing shirts to our hats and seasonal collections, we focus on creating products that feel premium while still representing the everyday outdoorsman and outdoorswoman.
One thing we’re especially proud of is the community and loyalty we’ve built around the brand in such a short period of time. Since launching in 2024, Ole Boy has grown to serve more than 30,000 customers and expanded into over 300 retail partner locations across the country. That kind of growth doesn’t happen without amazing customers, strong relationships, and a brand people believe in.
Above all, we want people to know that Ole Boy is built on perseverance, passion, and authenticity. We’re not a giant corporate company — we’re real people building something we care deeply about. We believe in treating customers right, standing behind our products, and continuing to grow a brand that reflects the values and lifestyle we love.
What quality or characteristic do you feel is most important to your success?
I believe the most important quality behind our success has been perseverance. No matter how difficult things get, we continue to push forward. Business is full of highs and lows, wins and losses, and unexpected challenges. The people who succeed are usually the ones who refuse to quit when things get hard.
I’ve learned over the years that success rarely happens overnight. It comes from consistency, hard work, sacrifice, and showing up every single day even when you don’t feel like it. There have been plenty of setbacks, failures, and difficult seasons throughout my entrepreneurial journey, but each one taught valuable lessons and helped shape the next opportunity.
Another huge part of our success has been authenticity. We built Ole Boy around who we truly are and what we genuinely love — the outdoors, family, faith, and hard work. We’re not trying to be something we’re not, and I think customers connect with that. People appreciate brands that feel real, relatable, and passionate about what they do.
At the end of the day, grit, determination, and staying true to our values have been the foundation of everything we’ve built.
Contact Info:
- Website: https://oleboy.com/
- Instagram: https://www.instagram.com/oleboybrand
- Facebook: https://www.facebook.com/oleboybrand
