⚠️ Uncensored excitement: this video contains some strong language from real life experience ⚠️
Greg LaVecchia woke up on a 160-foot yacht somewhere in the Greek islands, walked past four or five decks, and went straight to the gym. His wife was still asleep. His childhood best friend Leo Walter, president of their company Bloom, was somewhere on board with his own family. The boat, a charter called the Gecko, was worth close to $30 million. Ten years earlier, Greg was on his second academic suspension and had no idea how to build a website. The distance between those two mornings is the whole story.
Four years of looking like complete losers
The first phase of Bloom was not a pivot or a stumble. It was a prolonged stretch of public awkwardness that Greg describes without softening. ‘Do you know how embarrassing the first four years of this entire entrepreneurial journey was?’ he says on the trip. ‘We literally didn’t even know how to make a website. Everyone around us said, what the hell are they doing?’ The product at that point was instant-download PDFs sold through social media. Greg was wearing Halloween costumes in YouTube thumbnails to get clicks. Seven days a week, every week, creating content and hoping something connected.
The thing that kept it moving was not a strategy. It was refusal. The read Greg and Leo settled on early was simple: 99 percent of people quit after the first, second, or third attempt. Their only job was to not be in that group and let the days stack.
Leo Walter, who has known Greg since they were neighbors in high school, put his own framing on the discipline question when asked about it on the yacht. ‘You have to have a goal and you have to be willing to spend the time working on that goal,’ he said. ‘It may take you 10 hours of studying whereas it might take your friend 2 hours of studying. But the 10 hours is your reality. And so if you want the goal, you need to spend the time it takes you as an individual to get the goal.’
The Starlink, the slide, and why guilt does not factor in
By the time the Gecko was anchored off Santorini, Greg had reframed what balance actually looks like for him. The yacht had a Starlink connection providing enough bandwidth for all 15 people on board to stream simultaneously. He was on Zoom calls, using Claude for Bloom work, and watching Netflix with his wife in the evenings. At dinner the night before, the table conversation turned to Bloom business. The next morning, before breakfast, he and Leo were already mapping out which emerging influencers they wanted to sign. Then they went down the slide off the helicopter pad.
He refuses to call that a problem. ‘Why because I am here can I not talk about business? Why do I need to feel guilty about that?’ The trip started in England, where he dropped into London for a Bloom launch before the Greece leg began. Their travel agent handled everything from private flights out of Tuscany to staffing the yacht, which required a crew of at least ten and a full hour-long operation just to dock the boat, with multiple support vessels pulling ropes alongside.
Greg and his wife Mari had been to Santorini once before, on the cheapest midnight flights they could find, taking a ferry over with camera gear and staying every night except one at a hundred-dollar Airbnb. He is precise about why that history matters. ‘If I was sitting in Santorini right now at 31 years old and had all of this already built, I would be depressed.’
The helicopter pad at the end of a decade
The helicopter landing pad on the top deck of the Gecko served no operational purpose on this trip. Greg identifies it anyway as one of his favorite spots on the whole boat.
At 31, with Bloom scaled to the point where a portion of its customer base does not even know he owns it, Greg is not declaring victory. The framing he keeps returning to is the ten-year window: one generational run, fully committed, with the jagged and non-linear road accepted as the cost of admission. He reached 100,000 followers on this platform during the trip and marked it on deck with the crew. He said he still has no idea what he is doing on it.
The first time Greg and Mari found each other, it was a Halloween night in Greek life in college. Six months later, she was 90 pounds overweight and working through it, and he was on academic suspension with no employment path visible. They are both on the yacht now. That is the version of the story he wanted to put on record.
