Paul Allen and Larry Ellison were the Cain and Abel of the silicon set. They had a storied rivalry that sailed past the boardroom and into yachting. The Microsoft and Oracle Corporation cofounders’ race to build boats—Allen’s Lürssen-built Octopus in 2003 and Ellison’s Bannenberg-designed Rising Sun in 2004—kicked off a crazy billionaire boys club that saw other tech titans, such as Apple’s Steve Jobs and Google’s Sergey Brin (whose Dragonfly was for sale at the Monaco Yacht Show in September) also build custom yachts.

But the latest generation of tech billionaires, Jeff Bezos, Mark Zuckerberg, and Bill Gates, have upped the ownership ante by creating new style parameters and technologies that have pushed superyacht design forward. Bezos and Zuckerberg also have two of the coolest shadow vessels on the water.

Of course, superyacht ownership might not be all it’s cracked up to be for some of these owners. Besides being spotted everywhere they go, there could be safety concerns. Last weekend, a Florida man jumped on board the tender for Zuckerberg’s support vessel, Wingman, at a marina in San Diego. It’s not clear what his intent was, but he may have been headed for Wingman, or even Zuckerberg’s main vessel, Launchpad, before he was arrested at gunpoint.

In terms of owning a shadow vessel, video mogul Gabe Newell was one of the first to see the benefits, referring to it as an “external hard drive” of the main yacht to house extra staff, crew and a wonderland of toys.

Newell sold his 220-foot Damen support yacht, Dapple, last year to none other than Zuckerberg in preparation for his next big delivery, Project Y722. Newell’s Oceanco new build will go a long way to furthering his investment into ocean exploration. His 2022 purchase of the deep-sea Hadal Exploration System included a Triton 36000/2—the world’s first and only manned-submersible certified for dives to 36,000 feet.

Project Y722 will be Oceanco’s third-largest yacht to date following Jeff Bezos’s $500 million sailing yacht Koru. The 417-foot vessel is both the largest and tallest sailing yacht in the world (Sailing Yacht A is only sail-assisted). Bezos took delivery of his behemoth in April 2023, though it turns out a three-masted schooner is the one thing Amazon can’t deliver without a hitch.

Bezos came under fire for plans to partially demolish the famous De Hef bridge in Rotterdam, the Netherlands, to allow the yacht’s three 230-foot-tall masts to pass underneath. Crisis and controversy were averted when the yacht was instead shipped out of Oceanco’s Alblasserdam facilities in two pieces, before final assembly. Taking delivery of the largest Dutch-built yacht in the world whet Bezos’s appetite, and he twinned the purchase with Abeona, the largest support vessel built by Damen that same year.

Abeona’s $75 million build cost and 246-foot length are nothing compared to Koru, yet it’s still a serious asset. It sleeps 45 guests and 20 crew, including medical personnel. The large aft deck has a helipad and hangar for a D14 value helicopter, as well as marine gear, tenders, and toys.

Zuckerberg’s Wingman is also packed with amenities, though it’s not the only secondhand yacht that came from his 2023 shopping spree. The centi-billionaire scooped up the 387-foot Launchpad (formerly Project 1010), an Espen Øino–designed Feadship originally commissioned by (now sanctioned) Russian oligarch Vladimir Potanin. Zuckerberg is estimated to have paid a whopping $330 million for both yachts combined.

But that’s just over half of the $600 million that Microsoft cofounder Bill Gates is thought to have spent on his custom Feadship Project 821—the world’s first hydrogen-powered superyacht, which began tests recently. It’s no surprise that Gates, whose Breakthrough Energy Ventures fund has put more than $2 billion into companies that help reduce greenhouse gas emissions, should be the one to break ground on hydrogen-fuel-cell technology within yachting.

Project 821 can’t perform entire crossings on hydrogen, but it can cruise at 10 knots or run hotel functions at anchor for a full week on hydrogen. It also has a nifty sensor-packed smart A/C system and advanced heat recovery system, alongside more luxurious features, such as multiple pools, a wellness area, and a hospital.

What is surprising is the fact that Gates listed the yacht for sale prior to its delivery this year. He also sold his smaller 224-foot Incat Crowther-designed Shadowcat called Wayfinder in February, which after three years of private use recently entered the charter market. It’s characterized by a blue certified helipad that doubles as a pickleball court.

With most tech moguls already sorted on the yachting front, only Elon Musk remains in the market to take a custom hydrogen gigayacht off Gates’s hands. Judging by his vocal condemnation of the renewable fuel, referring to hydrogen as “the stupidest way” he could imagine for energy storage, it’s an unlikely match. Instead, the world awaits the arrival of the Tesla boss’s $700 million self-sustaining electric concept Model Y yacht, which he unveiled in 2021.

Despite being an avid charterer (Musk was spotted aboard a yacht in Mykonos in 2022), his comments on X—that he “prefers to work” than have fun on yachts—suggest it could be a very long wait.