Boisterous Below Deck Sailing Yacht season 4 Primary Charter Guest John Cerasani definitely made some sort of strong first impression taking his his shirt off right at the start of his charter. The entrepreneur and business influencer, his family, and friends kept Chief Stew Daisy Kelliher and the rest of the interior crew busy as a group of highly demanding charter guests, according to Bravo’s previews. Viewers will have to wait for episodes five and six to air before finding out just how rude John, TJ, girlfriend Natalia, Lauren, his son Jacob, and daughter Anastasia behaved on their trip aboard Parsifal III sailing in stunning Sardinia, Italy.

BDSY season 4 Primary Charter Guest John sailing in Italy with friends and family (Bravo).
Hopefully John and company don’t match the obnoxiousness of some of BDSY season 3’s charter guests. Below Deck fans won’t soon forget Primary Dr. Kim Nichols, her husband Chris and friend Dino firing orders and swearing and drinking like sailors on BDSY season 3. And who could forget Erica Rose and her ungrateful husband Charles? It turns out Primary John Cerasani, friends, and kids were pretty tame in comparison.
Who Is Primary Charter Guest John Cerasani On Below Deck Sailing Yacht Season 4

John with girlfriend Natalia and his son Jacob in Sardinia (Instagram).
Self-made millionaire and entrepreneur John Cerasani is a successful venture capitalist investing in companies in the entertainment, sports, gaming, leisure and hospitality industries. John founded Glencrest Global, based in Chicago, where he’s the managing partner. The investment fund John runs gives seed money to startup business looking for $100,000 to $3.5 million investment. Before that, John sold his insurance company back in 2015 for tens of millions.
Besides running his investment fund, John’s Instagram and TikTok posts make it looks like he’s auditioning to be the next shark on Shark Tank. The business influencer with nearly 100,000 followers swears constantly in his posts where he trashes his detractors. He also has a podcast and book called 2000 Percent Raise available on Amazon, which teaches fellow entrepreneurs how to pursue their dreams by telling his success story. His abrasive and aggressive style may have some viewers thinking of mobster John Cerasini, but Primary John’s much younger being in his mid 40s, and is a legit businessman, however gruff, and his last name is spelled Cerasani.
John played football in college, and was supposed to be the starting tight end at the University of Notre Dame, playing for renowned football coach Lou Holtz. Unfortunately he got in an off-season fight with a teammate which resulted in him getting suspended. Instead of serving his time, he transferred to Northwestern University in Illinois for his studies and to pursue his dream of being a professional football player. After getting a career-ending injury, Cerasani went into sales, eventually starting his own business.

John’s friends checking out his book (Instagram).
On Below Deck Sailing Yacht, John isn’t toning down his domineering demeanor in the slightest. Despite Daisy stressing out from all the demands and lack of help from exterior, she shared John’s stories on Instagram recently. So there’s no hard feelings.
John’s Friend TJ, Other Friends & Family Who Were Also Charter Guests On BDSY Season 4

Below Deck Sailing Yacht season 4 charter guest Natalia (Instagram).
John’s daughter Anastasia and son Jacob joined him and his friends on the luxurious sailing yacht charter. His girlfriend Natalia Miller also joined him. Despite his dad’s lack of decorum, Jacob showed better manners in asking for a cookies and cream milkshake. Jacob was using an electric hydrofoil when he collided with John’s friend TJ, who ended up with a nasty gash on his head where he was bleeding. He ended up needing stitches. Fans were not impressed by Jacob staying in the water after causing the collision, even though he claimed he didn’t know TJ was injured.

Natalia enjoying Paris around the time she went yachting in Sardinia, Italy (Instagram).
Hopefully the electric foil or hydrofoil (essentially a hover board on water) wasn’t damaged. Electric hydrofoils cost from $959 for a cheap model upwards of $13,812 on Amazon. (That explains why First Officer Gary King chastised deckhand Chase Lemacks for not cleaning it up properly in a previous charter.)
Lauren Watters also joined the group, but she keeps her Instagram private.
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