When you've got so much cash that you can, for example, have your wedding reception—not even your actual wedding—at the Palace of Versailles, something amazing can happen: you can use that money to make even more money in the tech game. (Cue Dr. Evil laugh.)

But it's not as easy as simply putting a $100 bill into a machine and having it spit back out even more Benjamins—you have to invest it, and then pray to the Geek Gods that it comes back to you, either in its full amount or more. If you've watched The Social Network or Jobs, they show how important financing was to Facebook and Apple's development, and the riches that can be made when things go successfully. Investing in anything comes with a risk—the bigger the gamble, the bigger the potential payoff—and investors can always end up losing money when the idea, timing, and eventual product just don't add up. But when it all comes together, boy oh boy is the payoff sweet. 

There's a group of celebrities that have tried their hand at investing in apps and startups, joining the game of strategic gambling that gave Silicon Valley its cutthroat rep. Investing in startups gives celebrities the chance to build something to fall back on when they're done with whatever made them that extra money in the first place—like, say, if they're an athlete with just a few more years left in the tank, or battling through injuries that can end their career at any moment. Staking a claim in a company that could potentially net them cash down the road gives them a safety net. There's a good amount of celebs who've launched or invested in startups (there were nearly 17 of them during the launch of the streaming service, Tidal), and some have been surprisingly successful (we're not counting Dr. Dre and Jimmy Iovine here, since Beats partnered with a larger company, Monster, when it started), while others had their investments flop harder than a floppy disk.

So here they are: the stars who have taken the biggest plunges into the tech world.