glass for dinnerElon Musk must love the taste of broken glass.

He is either the Job of the technology world, or he’s a masochist. Whether it’s self-inflicted or he’s the victim of circumstances, he just never seems to do this entrepreneurship thing the easy way. Even as a small personal fortune, past successes and frothy times should have made that possible.

Consider his first big hit, PayPal. It was founded at a time when you could get away with a half-assed business model on a napkin and take a company public. PayPal picked something incredibly hard, shoved together two companies with very domineering founders, and spent money faster than if they’d been standing on the roof throwing rolls of $100 bills over the edge, according to our PandoMonthly interview with Reid Hoffman. PayPal went public at the worst possible time: Some six months after the crash and September 11. And it was one of the only ones that made it out.

Musk followed that up, not with another easy company in the Internet space or trotting off to a venture firm. Instead, he decided to pick a trifecta of near-impossible spaces to build companies: Solar energy, electric cars, and rockets. Between them, these have had epic struggles, fights with investors, harrowing product failures, and near deaths. Musk’s personal life was dragged through the ValleyWag gutter. The one-time centi-millionaire had to borrow money from friends to make rent because he’d bet so heavily on these near-crazy ideas. Tesla was even unfairly and wrongly slammed and called a “loser” by Mitt Romney in national political debates.

Tesla almost brought Musk to his knees back in 2008, and even since going public in 2010, it hasn’t been an easy road. SpaceX failed on multiple launches before it finally succeeded. Of the three, SolarCity may have been the smoothest — until the last few days.

The company was finally going public, but at the last minute was forced to slash its price to $8 a share, much lower than the $13 to $15 it’d hoped to get. And it carries with it all the pressures of being the new bellwether for the maligned cleantech industry. For a capital intensive company in a growing but uncertain industry, that means it gets way less cash for growth.

But Musk is rapidly becoming a living legend for a reason. In each case, his gritty, steel-eyed determination and deep understanding of all these spaces seems to win out. Not to mention, he always invests with his own cash. He said before Solar City’s IPO he’d buy $15 million in shares personally at the public price. That’s in stark contrast to entrepreneurs and investors who can’t even wait for the IPO to sell shares. Tesla is undoutably on top now after the Tesla Model S was named “Car of the Year” by both Motor Trend and Automobile Magazine. And Musk has doubled down with an audacious plan to dot the country with a network of supercharger stations. Financially, Tesla has returned some 14 percent to investors year-to-date and is almost double its opening price. Yeah, total “loser,” guy who actually lost the Presidency.

SpaceX is still private, but its multi-billion NASA contracts and successful missions to the space station have given people a whole new reason to hope for America’s future in space. And Musk has intimated that eventually that one will go public too.

And even SolarCity ended the day up some 47 percent — cold comfort, given the cash it left on the table by pricing low. But it’s something.

As I’ve noted several times, Musk is only the second person in Valley history to build three companies that exited north of $1 billion each. (I’m counting SpaceX in that since it has billions in revenues already.) The first was Jim Clark who deserves props for Silicon Graphics and Netscape, but clearly benefitted from the bubble with Healtheon.

Not only does Musk — modestly — refuse to take credit as a co-founder of SolarCity and aim to up that number to four big wins as the company grows, but he’s achieved this in absurdly hard and varied industries.

It’s no wonder creating an entirely new form of transportation is on his mind next. It’s hard to imagine how he could challenge himself after all of this.

[For our hour-long PandoMonthly talk with Musk, go here.]

[Illustration by Hallie Bateman]