Steve Ballmer

"Steve Ballmer has similarly demonstrated the difference between billionaire-style risk taking and owning a diversified stock portfolio. In March 1989, Microsoft received an unfavorable ruling in its ongoing liti¬ gation with Apple Computer. The software company’s stock plummeted as investors fretted that Microsoft would be blocked from using certain Macintosh-like features in future versions of its Windows operating sys¬ tem. Sales chief Ballmer, who correctly foresaw that Apple would not ulti¬ mately prevail, shelled out $46 million to add to his existing large holdings of Microsoft stock. Three years later, he followed Bill Gates and Paul Allen into the billionaire ranks. By then, the Microsoft shares that Ballmer had purchased for $46 million at a low point in the company’s fortunes were worth more than $350 million."

"Some of our ventures led, some fizzled. But the ones that led were blockbusters. One that still leads is Expedia. I thought travel was the perfect business to be colonized by the internet. We found and bought a fast-growing but still small company called Hotel Reservations Network based in Dallas. It owned the name Hotels.com, and it was our first foray into online travel. Microsoft had also started an online travel service called Expedia, which by 2001 was getting some traction. After the dot-com bubble burst, I went to see Steve Ballmer, then CEO of Microsoft, on a mission to persuade him to sell it to us. It was still losing money and Steve felt Microsoft shouldn’t be in these internet verticals anyway and quickly agreed to let us have it in exchange for $1 billion of our stock. We were set to close the deal in October 2001 when you-know-what happened on September 11 and travel ceased to exist. We had an out clause in our deal for a “material adverse change,” and 9/11 was certainly that. We thrashed around for weeks asking ourselves how we could pay $1 billion for a travel service when there was no traveling. One day, as we were stewing around, someone in the room said, “If there’s life, there’s travel.” That rang loud enough for me to say, “That’s it—we’re betting on *life,*” and we closed the deal."