Double or Nothing: How Two Friends Risked It All to Buy One of Las Vegas' Legendary Casinos
staircase in front of me. One of those steps took me to a seat on Expedia’s board of directors in February of 2002, just as Barry Diller bought a 60 percent share of the company from Microsoft. Suddenly, I found myself preparing to sit at the same conference table to work side by side with the guy who’d screwed Tim and me over when we’d tried to sell him Travelscape!
    â€œIs Tom still mad at me?” Diller wanted to know before I joined the board.
    There are people who would’ve refused to enter a room with Diller if he’d done to them what he’d done to us. Make no mistake about that. But Sumner Redstone, the CEO of Viacom,says he doesn’t let history get in the way of the future. Anyway, that’s just the attitude I took.
    That first board meeting with Diller was a big day in my life—one of those days when you’re up before the alarm clock rings. Say what you want about the guy, but the list of people who’ve worked with Diller over the years grabs your lapels and gets your attention. Michael Eisner, who became the CEO of Disney, mentored under Diller. So did Jeffrey Katzenberg, who started DreamWorks with Steven Spielberg. At one point, they called those guys the Killer Dillers. I simply needed to know if I could hold a seat in the room at that level.
    I was staying in New York at my favorite hotel, the St. Regis. I put on my best suit. My best shirt. My best tie. Maybe I looked like I belonged in a Barry Diller boardroom. But inside I was still the same guy who had a hard time figuring out trigonometry. The same guy who’d been rejected by his high school basketball coach. The same guy whose dad would be deeply wounded if I ever sacrificed my solid Midwestern values for the almighty buck.
    I didn’t go out and buy a fancy house as soon as the money became available. I sent some to my parents, who’d given me those solid values. I sent some to my older brothers, who’d probably stunted my growth with all those Piledrivers and helped create my Charlie Hustle attitude. I sent some to my younger brother, John, who is so close to me that we talk five times a day. I sent some to my old backcourt partner Chris Bednarz for helping me learn how to synthesize. I gave some stock to a school that Andre Agassi and Perry Rogers were establishing for inner city kids in Las Vegas. Let me tell you, it’s a great a thing to be able to give the Nevada Cancer Institute a million bucks. Well, yeah, I also bought a Ferrari—which gave Tim the perfect opportunity to twist in his needle. “No, Tom, you haven’t gottenaway from those humble Midwestern roots. You’re just driving a Ferrari !”
    But there was probably nothing $105 million could buy to make me feel as good as the tape I received in the mail from Chris Bednarz’s dad not long before that board meeting with Diller. It was a recording of that basketball game against Totino-Grace. The Ferrari is long gone. But that win will always be with me. Now, I needed to know if I could seize the moment like that in Barry Diller’s boardroom.
    It was about five months after 9/11, and tension from the destruction of the World Trade Center still hung over the city. I stepped out of the street and into the anxiety of the boardroom. Everybody attached to Microsoft was anxious to find out where he or she would fit in now that Expedia would be under Diller’s control.
    Diller was very cordial. I sat between him and Greg Maffei, the former chief financial officer of Microsoft. I could hear my heart beating as I wondered when to jump into the conversation and how to time my comments so that I didn’t sound as long-winded as Tim would have you believe I am.
    After that three-and-a-half-hour meeting, I was no longer a kid who’d stepped into an amazing opportunity on a frozen lake still trying to find his way in the world. I knew I belonged at that table, and I was deeply aware of how much I’d

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