The harder part is carrying nearly 100 years of family history on his shoulders while figuring out how to keep the operation alive through hurricanes, federal regulators and a rapidly changing Florida tourism industry.CLICK HERE FOR MORE COVERAGE FROM OUTKICKHubbard is the fourth generation of his family to run Hubbard's Marina in Madeira Beach, Fla.The business traces its roots to 1928, when his grandfather started with five rowboats and 40 cane poles.Today, John's Pass in Madeira Beach is a popular tourist destination for water recreation, shopping and dining.
(Photo courtesy of Dylan Hubbard / Hubbard's Marina)Today, Hubbard is vice president of the company and has begun the process of purchasing it from his father.But stepping into the family business was never as simple as inheriting a title."Oh, you have no idea," Hubbard told OutKick Outdoors when asked whether he had to earn his place before calling himself captain.His grandfather, Wilson, originally ran the operation before leaving to serve during World War II.
Hubbard's great-grandfather stepped in during that time, which is why the family considers it a fourth-generation business.His father later purchased the company from the family in 2004.
Now, Dylan is preparing to carry it forward."It's also really cool to have that layer of: it's a family business.I'm fourth generation," Hubbard said.
"Not only am I working, but also it's that legacy.So it's just an added layer of maybe responsibility or honor or blessing — whatever you want to call it — that really makes it even that much more special."Watch Dylan Hubbard's full interview with OutKick Outdoors here:That responsibility means knowing when to hold onto tradition and when to embrace change.Hubbard's Marina began in Pass-a-Grille, back when Florida's barrier islands looked very different.
But as new bridges changed traffic patterns and Pass-a-Grille became increasingly residential, Hubbard's grandfather recognized that the business needed a new...