Having overseen approximately 500 companies, Branson, who is known for his charisma and eccentric behaviors, has an estimated net worth of $5 billion.
Ever the savvy businessman, Branson has spent some of his billions indulgently, but only to make money in return - like renting out real estate he owns (think Necker Island). When it comes down to it, Branson is rather frugal, opting not to own objects of pure luxury. He also donates much of his time and money to philanthropic efforts.
Below, see how the eccentric leader spends his billions.
Richard Branson launched his first business at age 15. In 1972, he founded Virgin Records and went on to launch the Virgin Group conglomerate. Through this, he's built an estimated $5 billion net worth.
Branson is well-known for his jet-setting adventures and eccentricity, such as dressing as a butterfly to run a marathon.
Virgin Media, Virgin Australia, and Virgin Atlantic are some of the biggest companies under Virgin Group.
Overall, Branson is frugal when it comes to luxury items, largely because he grew up in a middle-class family. "The idea of having a possession that is there just as pure luxury, and is not actually paying its bills is something which I'd be embarrassed about," he told The Guardian in 2002.
He does have a history of luxury purchases, but they're often more an investment than a personal indulgence.
Case in point: Branson once hired a plane for $3,000 when passengers were bumped off his flight to the Virgin Islands. He advertised the flight going one-way at $39 per person and made $69. It was his first ever flight, he said.
Also take for example the island Branson owns. In 1978, he purchased Necker Island in the British Virgin Islands for $180,000.
Five years and $10 million later, Branson built a resort on the island, which doubles as a home for him. It's welcomed many celebrity guests, from Kate Winslet and Kate Moss to Princess Diana and Larry Page. The Obamas have even vacationed there.
In 2006, he estimated the island's value increased to $60 million — a 33,233% increase from his purchase price. He previously called it "the best financial move" he ever made.
In 2009, Branson bought a 32-meter catamaran, which he named Necker Belle for around $6 million. Branson chartered her at Necker Island starting at $60,000 a week and recently sold her for $3 million.
He also bought a mini-submarine, which he named the Necker Nymph, for a reported $547,482. Starting prices to rent her begin at $25,000 for seven nights at Necker Island.
But Necker Island is only one of Branson's luxury real estate holdings, which are known collectively as Virgin Limited Edition. He also owns Son Bunyola; located in northwest Mallorca, the estate offers three luxury villas for guests.
Elsewhere in Europe, Branson purchased The Lodge, a ski resort in the Swiss Alps. One room rentals are around $945 a night and exclusive use in the winter for a week is $89,916.
The rest of Branson's properties are located in Africa — like Mont Rochelle, a hotel and vineyard near Cape Town in South Africa.
Branson also owns a resort in Morocco called Kasbah Tamadot. There's no word on how much he purchased it for, but the 28 rooms each run for $717 a night.
Branson has a thing for safaris. He owns Mahali Mzuri, a tented safari camp in Kenya's Maasai Nara National Reserve with a 40-foot infinity pool. Rooms are around $590 a night.
And Ulusaba, his fourth African property, located in the Sabi Sand Game Reserve, also offers safari experiences.
Before taking up residence on Necker Island, Branson lived in his Oxfordshire mansion in Kidlington, London. It's unknown how much he paid for it, but he did sell it to his children for $1.78 million.
He also owned a home in Holland Park, London. He bought it for $3.3 million and later listed it for $23.12 million.
In 2002, Branson still paid a mortgage. "It makes economical sense to me to have a mortgage," he told The Guardian. "I don't have a specially arranged discount, only because it might be embarrassing to have a special rate."
You wouldn't find a lot of expensive artwork hanging in any of his homes. He prefers to buy watercolors at a reasonable price, he told The Guardian.
He still owns a refurbished houseboat in London that he purchased for around $2,600, which is available to rent for a little more than $1,000 a week. He said never plans to sell it.
To jet around from place to place, Branson owns his own private plane — a Falcon 50EX, which costs around $21 million brand new.
Branson also drives a Range Rover, but it's gifted to him every year from the brand.
He also told The Guardian he doesn't spend much on clothes.
Branson previously said people won't let him pay for things. "I'll be in a restaurant and the manager will say: 'Oh no, it's on the house,'" he once said in an interview.
But he tips big when someone deserves it. "I certainly tip larger if I feel that people have done their work with a smile. But I don't splash out because I think that's embarrassing," he said.
He also tips generously when he has a special request — he once offered a London cab driver two first class plane tickets, worth around $5,276.
One thing Branson doesn't spend his money on: Gambling. He once took his two kids to Las Vegas and gave them each $40 in casino chips to teach them the perils of gambling.
However, the lesson failed because they accidentally left a few chips behind — which tripled into a small fortune.
Branson is big on philanthropy. He devotes 80% of his time to Virgin Unite, the charitable arm of the Virgin Group. Branson and The Virgin Group fund overheads and costs to the non-profit.
The charity has founded and supported a variety of projects including The B Team, The Carbon Room, The Elders, and Oceans Unite.
Branson has also signed The Giving Pledge, in which he promised to give away more than half of his wealth during his lifetime.
Branson puts time and money toward the environment. In 2007, he offered $25 million to scientists who could discover ways to save the planet from climate change as part of the Earth Challenge.
He also pledged $3 billion over the course of a decade to develop low carbon fuel and alleviate global warming.
And with more than 60 companies in Virgin's portfolio, Branson continues to invest money in expanding and growing Virgin with new ideas.
To Branson, the biggest luxury isn't money: "If we're talking about personal luxuries — and the luxury of being your own boss — the biggest reward is the amount of time one can find for family and friends."