According the U.S. Bureau of Labor Statistics, approximately 15% of companies survive to their 25th anniversary. While the average lifespan of family-owned businesses is longer — about 24 years — only about 30% make it to a second generation, which makes the 25-year milestone particularly special.
This year, Leonard’s Express celebrates its 25th anniversary with a series of employee appreciation events and a chapter in a new book that shares stories about industry-leading companies that have demonstrated the vision, values, and culture to stand the test of time.
“Powered by People honors the founders, families, employees, and communities who built the transportation industry through grit, faith, trust, and perseverance,” said Dr. Gina Anderson, who wrote the book as “a tribute and practical leadership framework for the next generation of entrepreneurs who want to build organizations rooted in purpose, culture, and human connection.”
“My family and I are incredibly honored and proud to be included in this special collection of stories,” said Elise Johnson, Director of Organizational Development for Leonard’s Express and a key contributor to Dr. Anderson’s book. “Being able to share a piece of our legacy alongside so many others is truly meaningful.”
As Leonard’s Express celebrates a quarter century as a leading transportation and logistics services provider, a brief review of the company’s history provides a roadmap to their success.
Modest Beginnings
What began as a small freight brokerage firm moving just enough freight to keep the lights on and make rent and payroll has grown into a national transportation and logistics leader — one that’s recognized as an innovator across a variety of business disciplines. Leonard’s Express is a perennial recipient of some of the industry’s most prestigious awards, including Best Fleets to Drive For, Top Companies for Women to Work in Transportation, Top Food Chain Providers, and Top Refrigerated Carriers.
Leonard’s Express was founded in 2001 by a close-knit group of entrepreneurs who had trucking in their blood, led by Kent and Patricia Johnson, and Dick and Vicki Trotta. Each brought a unique skillset to the table, and when they were joined by Kent and Pat’s adult children, Kim (with husband Mike Riccio) in 2001 and Kyle, Ken (with wife Connie), and Kevin Johnson over the next few years, the pillars of a strong new company were firmly set in place.
Starting a new company is much easier when the founders have decades of experience. Kent Johnson had previously built KJ Transportation from the ground up, starting in 1973 and eventually selling it 25 years later in 1998. This is where the family values that endure as a hallmark of Leonards Express were born.
“The culture was definitely family-based,” said Elise, granddaughter of founder Kent Johnson. “They knew every driver’s name, and any of them could go into Kent’s office and have a conversation. If they needed help, he’d tell them everything they did wrong but then hand them a check for whatever they needed. That was just how he was.”
Nothing exemplified the family atmosphere at Leonard’s Express in those early years more than payday. Pat Johnson would patiently wait each week to print paychecks and personally hand them out to each employee, a responsibility she lived for even after direct deposit became common practice.
In 2003, KJ, who missed having trucks and drivers, started adding trucks to Leonard’s Express through his farm, Pleasure Acres. In 2004, Johnson Equipment bought trucks to lease to Leonard’s Express, which kickstarted the company from a brokerage firm to a transportation company.
Operating out of its terminal in Farmington, New York, Leonard’s Express focused on hauling dry goods and produce, especially apples, throughout upstate New York with just 10-15 trucks and about 10 employees. Over the first couple of years, the company expanded to about 25 employees, maintaining its regional footprint while building a reputation for reliability and service.
As an asset-based trucking company that also specializes in brokerage services, Leonard’s Express helped connect small independent carriers with companies that needed freight moved. Building these relationships with companies and drivers created a strong foundation of trust with customers and business partners across the region.
A Turning Point
In 2007, the company that purchased Kent Johnson’s KJ Transportation nearly a decade earlier went out of business, and many former employees returned to the Leonard’s Express family. Almost overnight, the company grew from 11 drivers to 50. Many of the individuals who came onboard during that period are still with the Leonard’s Express today, creating a stabilizing force for the company’s culture and operations.
“When we brought over so many of our core people, that was a huge milestone for us and was extremely important in the development of our business,” explained Elise Johnson.
Around 2010, another major transition took place. Kent Johnson stepped down as CEO, passing the torch to his son, Ken. It marked the beginning of a new era, but not a departure from the company’s roots. Kent and Pat remained actively involved for years, offering guidance to maintain continuity while the next generation of Johnsons “took the wheel.”
National Expansion
The 2010s were defined by strategic growth and geographic expansion. Leonard’s Express methodically extended its footprint beyond the northeastern United States, opening new terminals and unlocking pathways to broader markets and customers.
The Johnsons made their first major move in 2010 with the acquisition of a terminal in Eau Claire, Wisconsin. This expansion allowed the company to establish a presence in the Midwest, giving drivers a home base closer to western freight lanes.
Around the same time, Leonard’s Express opened a terminal in Taylorsville, North Carolina. This location became a critical hub along the eastern corridor, providing drivers with a place to rest, refuel, and maintain their equipment while servicing key routes in the east.
Expansion continued with the purchase of a terminal in New Castle, Delaware. This strategic acquisition provided direct access to one of the country’s largest shipping ports and paved the way to several major partnerships. As a result, Leonard’s began hauling bananas for global produce giants like Dole and Chiquita, significantly elevating its profile in the refrigerated transportation sector.
Each new location helped Leonard’s Express build momentum. Each new partnership helped spread its stellar reputation.
In 2021, Leonard’s Express reached further west with the acquisition of its facility in Caldwell, Idaho, making Leonard’s a truly national operation for the first time. The Caldwell terminal enabled Leonard’s to secure large contracts with shippers such as Driscoll’s, now one of its top customers, and to haul products like tomatoes and potatoes that are not grown as much in the east. Leonard’s Express’ reach now spans from coast to coast, connecting farms, ports, and distribution centers across the country.
As its transportation network grew and nationwide demand ballooned during the COVID-19 pandemic, Leonard’s Express recognized the need to expand its logistics capabilities. In Farmington, New York, the company began developing warehouse space to complement its trucking and brokerage services at corporate headquarters.
In 2022, Leonard’s opened a state-of-the-art refrigerated warehouse, enhancing its ability to move and store perishable goods. The facility allows the company to offer integrated solutions for customers shipping produce and other temperature-sensitive products across the northeast while improving supply chain capacity and bolstering the regional economy.
More recently, Leonard’s Express completed construction of a massive dry warehouse, further diversifying its offerings and strengthening the company’s position as a full-service logistics provider.
Remaining Resilient and Preparing for the Future
Like most transportation and logistics companies, Leonard’s Express has faced its share of challenges due to the freight recession, which has brought unprecedented market volatility, rising costs, and shifting demand to the industry since 2023. Yet the company has remained nimble and resilient, adapting through innovation and strategic investments. By embracing new technologies to improve routing decisions, streamline workflows, and keep drivers and motorists safe, Leonard’s Express is well-positioned for future growth.
“We’ve continued to provide excellent service to our customers and earn industry accolades, even when faced with challenging circumstances,” said Leonard’s Express CEO Kyle Johnson. “We’re always looking to improve, and I’m proud of the work our teams have done to ensure our customers keep coming back for more.”
To mark the 25th anniversary, Kyle Johnson shared a message with all employees, thanking them for their hard work and dedication. Employees will celebrate the milestone with festivities at each terminal over the summer.
What began as a relatively small regional business has grown into a multi-generational enterprise, with sons, daughters, spouses, and now grandchildren all contributing to its success. Today, three generations of Johnsons have worked for the company, and nine Johnson family members (the most ever) work alongside the Leonard’s Express workforce of nearly 1,000 strong.
From a small brokerage moving freight across upstate New York, to a national transportation and logistics leader serving some of North America’s largest brands, Leonard’s Express has built its success on relationships, resilience, and remaining true to their deeply and universally shared sense of family values.
“We have proven to ourselves and our customers that we’re not going anywhere,” said Elise Johnson. “We’ve been here for 25 years and we plan to be here for 25 more.”
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