40 Under 40 Class of 2025

Janessa Weiland, 39

  • By Janet Leiser
  • | 5:00 p.m. October 9, 2025
  • | 0 Free Articles Remaining!
  • Class of 2025
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Janessa Weiland took a leap of faith in 2009 when she left her job as sales director of a Naples boutique hotel to join brother-in-law Brian Chapman’s startup — 75 miles north in Port Charlotte.

“I knew nothing about insurance,” says Weiland, who studied hospitality management in college.

Janessa Weiland with her mentor, her mother Janet Stedcke.
Photo by Mark Wemple

 

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