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June 29, 2025

Talbot Spy

Nonpartisan Education-based News for Talbot County Community

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1 Homepage Slider 3 Top Story

Maryland 2.0: A Chat with Father-Son Wilson and the Preston Motors Success Story

March 23, 2020 by Dave Wheelan

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Perhaps it is a coincidence that our conversation with David Wilson, and his son, David Jr, will be broadcasted during one of the most significant economic downturns in American history. But the story of Preston Motors, and its unprecedented rise to being one of the top 33 Ford dealerships in the country out of 3,400, it a tale of a father and son team that rose from the ashes of the last great recession we had in 2008.

While David Wilson had started selling cars right after high school, and within four years had purchased his first dealership several decades before, 2008 marked a landmark year when his son joined the family business. After completing Ford’s own four-year college, David Jr. returned full time, and the father-son built their very own internal marketing team. Within a few years, Preston had become so sophisticated in marketing their dealerships through the web that they climbed to the top 50 list using their beloved Frog branding and sticking by their community. They also created a national marketing firm to help other dealers using many of those same techniques under the ifrog banner.

In the Spy’s ongoing series of documenting some of the Eastern Shore’s most entrepreneur businesses and their founders, it was not hard to ignore the Wilson family and their committed associates for building an extraordinary success story from downtown Preston, Maryland with its population of 718 residents. Thus becoming a mouse, or frog if you will, that continues to roar from the middle of Caroline County.

This video is approximately seven minutes in length. For more information about Preston Motors and Ifrog marketing, please go here.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 1 Homepage Slider, 3 Top Story Tagged With: Caroline County, David Wilson, Jr., Preston Motors, Talbot Spy

About Dave Wheelan

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