We asked nine local businessmen to share the hardest lessons they’ve had to learn — and how those experiences changed the way they show up as leaders today.
Shawn Doss
The Cigar Box | www.thecigarboxalabama.com
The biggest hurdle for me to overcome was recognizing the value of employees. In the beginning, I was a one-man operation. It was not until we began hiring employees that we started seeing real growth. Currently, we have 10 employees across our three businesses (The Cigar Box - Cullman and Jasper, and GoTees Screen Printing - www.shopgotees.com). Our employees are what keep the "machine" running!
Josh Phillips
Pin High Cullman | www.pinhighcullman.com
Maven Mortgage | www.mavenmortgagegroup.com
The hardest lessons are the ones that take the longest to learn. For me, it’s been surrendering control and trusting God with the outcome. I’ve learned that’s not only more peaceful, but more effective. The work is still the work, but results don’t dictate my attitude or effort when serving people. I choose faith over fear, trusting the right opportunities come in God’s timing.
Justin Self
CrossFit the Vault | www.crossfitthevault.com
The hardest lesson I learned as a business owner at the beginning was that I thought it was all about cash flow and paying the bills, but that is not what solves all your issues. People join a gym for the equipment and the "work," but they stay for the people. I quickly realized that without a loyal culture, you're just a commodity fighting a price war. We have focused on the community first and the business second. This shaped us into a gym that values connection over conversion, ensuring long-term loyalty and a brand that has a purpose.
Raymond Young
Mary Carter Store | www.facebook.com/marycarterstore
As a senior in high school, I entered the business world delivering Birmingham newspapers, driving 92 miles daily, seven days a week. This built my discipline and commitment. After college, I taught at St. Bernard while saving to buy a Mary Carter Paint Store franchise. For seven years, I balanced teaching and running the store before committing fully to the business for over 50 years. The greatest lesson I learned was how to be self-sufficient – providing for my family while ensuring the business remained financially stable. I developed many skills in my role as a business owner, ultimately passing this knowledge on to my sons, who now run the store.
Jeffrey Young
Mary Carter Store | www.facebook.com/marycarterstore
One of the hardest lessons I’ve learned in managing our second-generation family business is not getting lost in the small details. I work every day with my two brothers to carry on the legacy our father built, and focusing on the big picture serves our purpose much better. At first, I thought being involved in every little thing meant I was protecting the business. In reality, that often slowed us down and created more stress. I’ve learnt that delegating and empowering others is the better approach, but I’m still working on it. I continue to push myself to step back, share responsibility and grow into a better leader. Learning that perfection should never be the goal has been my most important lesson.
Rob Henshaw
Henshaw’s Healthy Habits, LLC | coach.optavia.com/priscillaandrobhenshaw
The hardest lesson I’ve learned is this: you cannot outwork poor health. I tried. Long hours, low energy, scattered focus and diminishing returns. Getting healthy changed everything. I lost over 80 pounds, reversed serious health issues and gained the energy and clarity I was missing. Now I operate at a higher level across everything I do. Better decisions. Better consistency. Better results. It also reshaped my purpose. I am passionate about helping other businessmen take back their health, especially those who feel stuck, because when that clicks everything else starts to level up.
Jeremy Mize
Mize Electric | www.mizeelectric.com
One of the hardest lessons I’ve learned as a business owner is that not every customer is the right fit, and that’s okay. Early on, it was tempting to take on any project, but I’ve come to realize that not everyone values the same things we do. Some customers are simply looking for something that works well enough, regardless of the level of craftsmanship or long-term quality. While there’s nothing wrong with that, it doesn’t align with how we approach our work. This experience has shaped me to be more intentional about who we work with. Our ideal customers are those who appreciate quality craftsmanship and want the job done right the first time. Focusing on those relationships has allowed us to maintain higher standards, take more pride in our work and ultimately deliver better results.
Chris Branham
Branham Tire & Auto | www.Branhamtire.com
With 26 years in business, I have learned to navigate the pressures of managing employees, serving customers, meeting deadlines and maintaining financial stability. I have come to enjoy these pressures because they help me stay focused and motivated. Balancing these demands with my personal life requires attention to my spiritual and physical well-being. I follow a simple principle: “WAYFO” — What Are You Focused On — believing that what you focus on will expand. I also believe that when we run toward challenges instead of away from them, they often lead to positive outcomes. My priorities remain: God, family, then business. Philippians 4:13 "I can do all things through Christ who strengthens me.”
Zac Yow
Nomadic Threads / Roam & Remember | www.nomadicthreadscullman.com
Thomas Edison once said, “I have not failed. I’ve just found 10,000 ways that won’t work.” That quote captures the hardest lesson I’ve learned in business. Some days feel like both wins and losses. It’s important to find ways to improve in the wins while keeping a positive perspective on the losses. Mindset is everything! As a business owner, you decide what defines a win or a loss. The success or failure of your business is directly tied to how you think, act and talk about it.