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Family Ties Inside the Fleet Families Building Careers Across Generations

Three fleet families share what it really takes to work together, learn across generations, and keep business from following them home.

September 15, 2026

What happens when the people shaping your fleet career are also the people sitting across from you at Thanksgiving?

In this episode of Shades of Fleet, Lauren Fletcher talks with three very different fleet families about working together across generations. Identical twin sisters Diana Holland and Laura Bloom bring complementary perspectives to the industry, the Dunton-Jackson family shares lessons from three generations in fleet, and Bob and Sam Adamsky reflect on a father-daughter connection built through automotive and fleet work.

Their conversations get into the realities of family business, including work ethic, technology, changing perspectives, disagreements, work-life boundaries, and the lessons that move both up and down the generational ladder. It is a look at how family can shape a career without requiring every generation to approach the work the same way.

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