Josh has been a golf caddie for nearly 20 years at the greatest course in the United States, Pebble Beach Golf Links. He is also a fine artist with an extensive portfolio of paintings. @caddie_whisperer

Known as Mossin' Annie, Annie Martin is the author of The Magical World of Moss Gardening, the definitive guide on the subject. The owner of Mountain Moss Enterprises, Annie creates innovative landscaping alternatives using mosses.
www.mountainmoss.com

Mike runs four Mister Softee ice cream trucks, two hot dog trucks, a Nathan's/Mister Softee store, and four summer concession stands. He's made over one million ice cream cones, and counting. Mike is a retired detective with the Westchester County Police, where he was also a member of the bomb squad. *This episode was recorded on location.

Avi Loeb is an astrophysicist and professor of astronomy. He is the head of the Galileo Project, founding director of Harvard University’s Black Hole Initiative, and the former chair of the Harvard astronomy department from 2011–2020. He is the bestselling author of the books "Interstellar," and "Extraterrestrial." *This episode was recorded on location.

Author of the recently released memoir "The Blonde with the Balls," Patty has been a fixture in the art world in New York and Los Angeles for 50 years. She has worked as a curator, dealer, artist's agent, and opened her own gallery at 25-years-old: the Hamilton Gallery of Contemporary Art in New York.

(Diners) George Psarofagis is a restaurateur and owner of the Holiday Diner. The second-generation of his family in the business, George has worked in diners since he was seven years old. *This episode was recorded on location in booth #3.

(Entertainment lawyer) Nina is an attorney representing creatives and influencers for over 20 years. She is the founder of Ameri Law, with entertainment industry clients across the United States.

(Commercial fishing/shipwrecked) Rory is the author of "Down at the Docks," on the characters and community of the largest fishing port in the United States. Rory has sailed solo across the Atlantic four ½ times. He’s written books on the Democratic Republic of the Congo, journeys the Himalayas, and meeting with Osama Bin Laden in Sudan. *This episode was recorded on location.