Nothing ventured, nothing gained is often the philosophy of very successful entrepreneurs. Calculated risk takes courage and intelligence, but it also requires an ability to welcome the uncertainty that comes along with it.

Risks often don’t pay off and almost always don’t work out the way you might have originally imagined, so being able to flow with the way your business is changing is an important skill to master. There might be failures along the way, but as this group of entrepreneurs has proven, there are also huge rewards.

Here are five entrepreneurs who are embracing and dominating risk today:

Elon Musk is the co-founder of PayPal, which for many entrepreneurs may have been enough for a successful career in itself, but it was just the jumping off point for him. Musk has since gone on to create Tesla Motors, the electric car company whose stock was up 625 percent in 2013 over 2012; and Space X, the first private company to send and dock a space shuttle at the International Space Station. He is also co-founder of Solar City, a national residential solar panel provider.

Related: 5 Takeaways From Michael Dell and Elon Musk's Power Pow-Wow

With so many literally out-of-this-world achievements, there are even infographics circulating that he’s the real Tony Stark. So what’s the trick? Tons of hard work, calculated risks and being okay with failing are the tools needed. Elon summed this up best in a January 2005 interview, “There's a silly notion that failure's not an option at NASA. Failure is an option here. If things are not failing, you are not innovating enough."

Richard Branson is one of the best-known entrepreneurial risk-takers in the game. The famous founder of Virgin has tackled everything from starting his own phone service with Virgin Mobile, to disrupting the airline industry with Virgin Atlantic and Virgin America. Ever since Sir Richard was a young lad, he has been hustling up plenty of business ideas that involved loving and learning from risk.

With that kind of a successful career, comes plenty of failure, too. Branson however claims that’s the secret sauce to his success. He recently shared in his Entrepreneur.com column, “Few first ventures work out. It is how a beginning entrepreneur deals with failure that sets that person apart. In fact, failure is one of the secrets to success, since some of the best ideas arise from the ashes of a shuttered business.”

Don’t be daunted by the risks ahead -- challenge yourself and see what comes!

Related: Richard Branson on the Secret to Success: Failure.

Brian Armstrong and Fred Ehrsam. If you don’t recognize their names yet, you will definitely know their company, Coinbase. Taking on the digital alternative currency market by creating their own digital wallet, Brian and Fred are perhaps the ballsiest risk takers in the game today.

Creating a secure, global digital wallet for users to buy, use and accept bitcoin is no easy feat. Just like the early days of banking in the west, digital currency is in its “frontier” stage and still highly susceptible to the threats of hacking and cyber-security breaches. However, at two years old and more than one million digital wallets downloaded, Coinbase is leading the way for a bitcoin-friendly global economy.  

Drew Houston. If you’re one of the over 175 million users who use Dropbox, you can thank Drew Houston for taking some big-time risks to see his company through to today. Drew was an MIT student tired of hauling around USB sticks and emailing himself documents to ferry information across computers. He co-founded the idea for Dropbox and started it in 2007 to allow file access through any computer via what we now call “the cloud.”

This wasn’t a straightforward climb to the billionaire list, however. Houston had to search for a co-founder before finally finding and gaining the support of fellow MIT student, Arash Ferdowsi. Then there was that whole epic head-to-head battle in 2011 with none other than Steve Jobs himself, who let Houston know personally that he was coming to take over the Dropbox market with his iCloud service. Risk may mean a bumpy ride, but in the end, Houston would tell you it has been worth it.

Related: Put Yourself on the Road to Success With These 5 Principles