Win Cramer recently traded his boardroom view for ocean blues, appearing on Bravo’s Below Deck Down Under with his wife Lori and a group of friends. The destination? The Seychelles. The vibe? High-energy, full-send fun.
And yes, the “Say what? Seychelles!” line was all Win. “I came up with it at dinner one of the nights before we boarded,” he said. “It just rolled off the tongue.” While Lori was initially hesitant to go on the show, she later said it was the most fun she’s ever had—and that she was glad Win pushed her to do it.
Rocking the Yacht Life
The group boarded the luxury yacht Katina and were met with full Below Deck fanfare, Captain Jason, Chief Stew Lara, and Chef Tzarina rolled out the red carpet. The food? Top-tier. “All amazing,” Win said, “but the crab benedict she made in the morning was my personal favorite for sure.”
Of course, it wouldn’t be Below Deck without a little chaos. The seas were rough, really rough. “The boat rocking was BAD,” Win said. “And it was hot. You put the two together and you’ve got some sick guests.” While Lori handed out her stash of Dramamine on the first night, Win stayed steady. “Lucky for me, I don’t get seasick.”
Pirates, Pranks & Picture-Perfect Views
One of the highlights of the trip was the pirate-themed scavenger hunt on a remote beach. “The beach day was a ton of fun,” Win said. “The water was amazing, warm, and SOOOO blue. And I love blue.”
Off camera, there were still plenty of laughs. “Lori, Cristal, and I stayed up late one night and made up a story about going to a party off the boat,” Win said. “The crew played along with it. Everyone (but one) believed us and had some serious FOMO.”
Win also connected quickly with one of the crew members. “Harry knew JLab, he used to work for one of our retail partners in Australia and had sold our products for a while,” he said. “Honestly, I’d hire just about any of them. They all had something unique that made the trip special, and I could see that gift working at JLab too.”
From Bravo to Business
Even amid the drama, waves, and tropical heat, Win kept his CEO mindset intact. “We were all very aware that we run companies and needed to act the part,” he said. “That said, there were definitely a few moments where we looked at each other like, ‘Did he/she really just say that?!’”
Reflecting on his experience watching the crew in action, Win noted a few leadership parallels. “Captain Jason was calm, decisive, and always put his crew first, something I try to emulate every day,” he said. “You could see how much they respected him because of that.”
When it came to navigating challenges, whether choppy seas or tight timelines, Win said it actually felt familiar. “The unexpected always happens, whether you're at sea or running a business. You just have to stay focused, support your team, and roll with it.”
And while he hadn’t yet watched the episode when we spoke, he was ready for anything. “We’re watching it as a group,” he said. “Should be fun to relive it all together.”
Catch Win on TV
You can watch Win Cramer’s nautical adventure on Season 3, Episode 16 of Below Deck Down Under, titled Come Swell or High Water, available now on Bravo.