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Yep, I am a real guy – James Dale. For 20 years, I tended bar in Westchester Country, New York. Over the last few, I developed a pub trivia where I wear my signature Captain’s Hat, blast yacht rock and ask “not an intelligence test” questions to local restaurant-goers.


Oddly enough, it developed a following. Two of the best compliments I ever got were:


“Your trivia is a real escape. I forget about what’s going on for 90 minutes and I really need that.”




“I am super competitive normally, but, for some reason, I don’t care whether I finish first or last here.”


There is just something about Christopher Cross, Kenny Loggins, the Bee Gees, Boz Scaggs and trivia that works. I thought maybe I was onto something.


I started to bring my trivia ship online, to use it as a way to bring people together for conferences, HR events, fundraisers and parties – a real reward for hardworking people to escape. In just the first few months, Fortune 500 companies, PTA’s, birthday parties and conferences all booked CJT.


I continue to be a real guy. All the trivia is handcrafted. You will hear me talk about my new tattoo or ear piercing, what is going on in the world of sports, being a father and starting my own business right before my 50th birthday, or my rock band, the Lords of Hawthorne. You will certainly hear a lot of gratitude.


Mostly, though, you will see my focus on the people playing, making sure the game has those yacht rock vibes. It’s not just about the music. It’s about the smiles, the collaboration, the bonding, the “escape,” where it doesn’t matter too much whether you finish first or last.


Like so much of the Captain's Crew, CD Caroline met Jim at one of his regular trivia nights. Her effect on the game was instant -- she is principally credited with making sure that female rockers and celebrities are regular fixtures in Rounds 2 - 4. In so many ways, she has had trivia host written all over her from square one:

  • She has 17 years in TV Production for ABC, VH1, Animal Planet TruTV, Lifetime, HGTV and TLC

  • Nationally syndicated weekly radio talk show host of Radio with a Twist

  • Contributor to Fashion Police in Us Weekly Magazine, as well as essays in Scary Mommy and Romper

  • An Aca-Awesome Yale grad raised in Westchester like so much of the crew

There's very little about pop culture that gets past the Cruise Director. She is the founding host of the Sunday Brunch League and regular host of Pocket Protector Wednesdays.