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Calculated Risk is an investment company with an equity position in six Harley-Davidson dealerships and two Lucky Penny Cycles pre-owned motorcycle dealerships, real estate and other interests. Calculated Risk also offers comprehensive dealership consulting, real estate development expertise and business investment services. ​

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Adam Smith was born and raised in the DFW area and joined the Harley-Davidson motorcycle business in 1991. In 1996, Smith opened his first Harley-Davidson dealership in Grand Prairie, Texas, making him the youngest person to own and operate a Harley-Davidson dealership at the age of 22. Eventually, he became one of very few Harley-Davidson dealership group owners in the country. 


As an established and respected resource in the powersports arena, Adam evolved the Calculated Risk brand from dealer ownership/management to an investment business offering services that also include real estate development and consulting, and dealership loans.

In May 2022, Adam sold the eight Calculated Risk dealerships, including Texas’ largest Harley-Davidson dealership, to Navigant Oak, LLC, a private holding company.


The sale to Navigant Oak represents one of the first dealership acquisitions by a financial buyer in the Harley-Davidson arena. Previously, the parent company typically prevented family offices and private equity investors from acquiring dealership franchises. However, in Smith’s role as 2018 president of Harley-Davidson’s Dealer Advisory Council, he was instrumental in working toward relaxing ownership restrictions to facilitate growth for all dealer owners. The Calculated Risk sale to Navigant Oak allows Smith to retain 20% ownership of his dealerships as well as a seat on the board of directors.


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