Growth heroes: Building a family business & having a life

This article is a part of our Risk + Reward series. Capital One Business and Inc. partnered to survey 314 business leaders in November of 2024 to explore the factors that affect how they weigh business risks and rewards in navigating modern business landscapes. View our key findings and other articles in this series.

Entrepreneurs and leaders of fast-growing companies aren’t always known for having the best work-life balance. Sometimes, it takes a little patience and intentionality, says Kyle Dennis, president of 5Boys Apparel, a family-owned and operated screen printing and embroidery company. Dennis says they may need to “grind it out” for a few years to build a business that can keep growing without constant attention.

Kyle is lucky. Even when the business is demanding, he has his family nearby. His mom, Robin Dennis, started 5Boys Apparel in Madison, Alabama, in 2010 after embroidering her sons’ travel sports team’s uniforms. “I honestly never dreamed how big it would get, after starting in our garage, and that it would be our boys’ livelihood,” Robin says.

For four years, 5Boys has grown 100 percent year-over-year, earning three Inc. 5000 honors. The best part is how the family built the business together. “I am so proud of our boys and how they have grown the business,” Robin says.

Four of her five sons now work at the company. Gary Dennis, Robin’s husband and the boys’ father, joined the operations team full-time in 2024. “We get to spend a lot more time together than most families do. Fortunately for us, we enjoy each other’s company,” Kyle says. And while it’s not easy, he has found some ways to promote better work-life balance.

Kyle says boundaries are important. So, when the family’s together watching the Super Bowl, for example, they avoid talking about work. “We try to separate the two as best we can. But at the end of the day, this business is, I wouldn’t say our life, but it is our livelihood,” he says.

Now that Kyle has children of his own, he is more conscientious about stepping away from the office. “I am less focused on making as much money as humanly possible and more focused on creating freedom,” he explains. He suggests business leaders define their version of success, thinking beyond revenue targets. Even in times of pure hustle, Kyle cautions against working around the clock. If you burn out, you may slow down your business and jeopardize your health, he warns.

Working smarter through automation and efficiency is important to the Dennis family. Paid digital advertising campaigns are critical for 5Boys, generating leads faster than other marketing avenues. The platforms they use have built-in automation capabilities which make managing advertising campaigns simple and fast. However, Kyle adds that you can’t fake a good product and must be ready to deliver whatever you are advertising.

Another time-saving strategy is to look to your business partners, including your banker, attorney, vendors, and mentors for advice and guidance. Their counsel can improve and speed up decision making, so you have more time for the people you love.

Even in planning spending, the 5Boys team tries to work efficiently. Kyle and his team put their advertising expenditures on a Capital One Business Spark Cash Select card, which earns unlimited 1.5X cash back. They use that cash back to offset their credit card purchases.

“Capital One Business has been instrumental in our growth overall. We’re family-owned, family operated; we don’t have any outside investors,” he says. Kyle credits the access to capital the company has received through Capital One with helping 5Boys to grow from a garage-based business to a 35,000-square-foot warehouse with 10 automatic presses.

For this family-owned business, striking the balance between the business that supports them and living their lives is a constant balancing act. By embracing boundaries and being thoughtful about everything from the tools they use to how they spend, they find time for both.