A wise investor’s train of thought typically isn’t, “Hey, let’s start a hot-air-balloon company!” Sir Richard Branson is an exception. The Virgin mogul’s multi-billion dollar empire reflects his personal interests and eclectic hobbies, from luxury air travel, to luxury ocean travel . . . and most recently, luxury space travel (read William Langewiesche’s report on Virgin Galactic, which suffered a fatal test-crash last year, in the April issue).

But out of Virgin Group’s roughly 400 companies, the handful that really stand out are the ones that reflect Branson’s independent streak. So for posterity’s sake, here’s a rundown of the most memorable Branson side projects and risky investments—Virgin Cola, anyone?

Virgin Balloon Flights

Virgin Balloon Flights was born out of Branson’s love of hot-air balloons, an affair fueled by his adrenaline junkie ways (transatlantic crossings, skydiving, kite-surfing, and the like). Branson accomplished several balloon-related feats, including crossing the Atlantic and Pacific Oceans. Although he failed several times to circumnavigate the globe, the publicity undoubtedly helped to bolster business. Virgin’s expanding balloon fleet currently operates more than 100 launch sites throughout Great Britain and Italy, with flights starting at £79 ($117) per person.

Virgin Drinks

Virgin’s liquid venture began in 1994 with a line of soft drinks and spirits that included Virgin Cola and Virgin Vodka. The business never could grab a foothold in the beverage market due to the overwhelming dominance of Coca-Cola. Now the world will never again get to savor the taste of Virgin Cloudy Lemon.

Virgin Oceanic

While Virgin Galactic toils away with conquering commercial space flight, Virgin Oceanic has its eyes set on the deepest parts of the ocean. The company fares well enough at sea level, chartering private yacht excursions and shallow submersibles. The end goal is to begin operating deep-sea dives that could ultimately reach a depth of six to seven miles (price per dive ticket: $500,000), but various technological setbacks forced Branson to put the project on hold.

Virgin Limited Collection

While your friends and neighbors rake in cash thanks to Airbnb, Branson began renting out a selection of his private residences, because who doesn’t want to live like a billionaire? Virgin Limited Collection, a high-end vacation rental boutique of sorts, includes The Lodge in Switzerland, Necker Island (private, of course) in the British Virgin Islands, and Ulusaba, a game reserve in South Africa. Necker Island goes for $42,000 per night (or $27,000 per week, for you penny pinchers), while a room at Ulusaba starts at a mere $482.

The Virgin Voucher

Apart from ballooning and boating, Branson's most beloved hobby is making money. He is a businessman, after all. No other venture reflects this quite like The Virgin Voucher, a monetary system akin to gift cards. Customers can purchase vouchers in £5, £10, £20, and £50 increments for such services as Virgin Wines, Virgin Holidays, and the aforementioned Virgin Balloon flights. It’s the perfect gift for anyone who wants to live life like a Virgin.

Virgin Brides

Branson shaved his signature goatee and wore a wedding dress to unveil his lacey new venture in 1996, but Branson still couldn’t survive the cutthroat world of bridal wear. “Why did Virgin Brides fail?” Branson pondered in a recent blog post. “Because we soon realized there weren’t any!”

In Memoriam

Virgin Brides, Virgin Cola, Virgin Cars, Virgin Cinemas, Virgin Digital, Virgin Energy, Virgin Express, Virgin Films, Virgin Limousines, Radio Free Virgin, Virgin Sun, Virgin Vie, Virgin Vodka.