20 Questions with Cherisse Ponraj

Ponraj is owner and operator of GirlsSailing.com.

Cherisse Ponraj began her career at a market research firm in her native upstate New York, embarking on a professional journey that has spanned 30 years. She is now based in Pinellas County. 

At 24, Cherisse discovered a new passion: sailing. She enrolled in an American Sailing Association class, igniting an enduring interest. As her skills advanced, she progressed from crewing on racing vessels to captaining larger boats, accumulating several ASA certifications along the way.

Her enthusiasm for sailing extended beyond personal enjoyment. She began organizing women’s weekend sailing retreats, fostering an environment of support and empowerment. This initiative led to the creation of GirlsSailing.com, a charter program designed to encourage more women to experience the adventure, and freedom, of sailing.

1. College alma mater? St. Petersburg College.

2. Favorite TV show of all time? Lost.

3. Preferred place for a business meeting? My sailboat.

4. Most used phone app? Navionics.

5. What time do you wake up on workdays? 5:30 a.m.

6. What’s a life hack you swear by? It might sound cliché, but practicing hot yoga covers so many essential life hacks that I can’t help but consider it the most valuable one I have.

7. First album/cassette tape/CD you remember buying? U2.

8. Favorite local restaurant? Shiso Crispy, in St. Pete.

9. Last book you read? The Nightingale, by Kristin Hannah.

10. Biggest business failure? Thinking I can do more than I’m able to and not asking for the right help.

11. What was your first cell phone? All I remember is that it was a bag phone, circa 1994!

12. Something you cook really well? Brazilian shrimp soup.

13. Most famous person you’ve ever met? Julia Roberts.

14. What is the last thing that made you laugh really hard? My 7-year-old daughter recounting the vibrant conversations, and social dynamics, that emerge in her second-grade classroom. Very amusing!

15. What is a movie you will NEVER watch again? The Blair Witch Project.

16. Last place you traveled for fun? Disney World.

17. What was your first car? A powder blue Plymouth Tourismo.

18. Charity you support? St. Francis Rescue.

19. What is something silly you got in trouble for as a child? Shaving my legs.

20. Best advice ever received? Be kind to yourself and to others, while living every day with courage.

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