William Draper III’s book, THE STARTUP GAME, comes out today, and for those of you who haven’t already pre-ordered it on Amazon, order it now. This book is a must-read for anyone who wants to understand the inner-workings of Silicon Valley business. As one of the forefathers of Silicon Valley venture capital, Draper’s early stage investments speak for themselves: Skype, Apollo Computer, Hotmail, OpenTable… But the book is more than your typical business “how to succeed” testimonial.
The book recounts the early history of Silicon Valley (when it was mostly fruit orchards, apparently), examines the philosophy behind Draper’s business dealings, and delves into his adventures as the administrator of the UNDP, when he was the highest-ranking American member of the U.N. during George H.W. Bush’s administration. Don’t worry: there are also plenty of first-hand war stories from behind-the-scenes at Yahoo, Zappos, Tesla Motors, Activision, and many other high-profile companies. Ultimately, the book examines what it takes to succeed in the high-pace, highly-competitive, high-tech startup world. And trust me, when it comes to playing the startup game, Draper knows what he’s talking about. You don’t have to take my word for it, though. Check out the book’s endorsements here. Everyone from Christopher Buckley to President George H.W. Bush has something to say about it. Eric Schmidt, CEO of Google, wrote the book’s Forward for God’s sake.
A few FUN FACTS about Draper:
- Draper’s family has venture capital in their blood: Draper’s father, General William H. Draper Jr., was a venture capitalist, and his son, Tim Draper is a venture capitalist and a founding partner of DFJ.
- Draper’s face is on the $2 stamp in Somoa.
- Draper ran for congress against Shirley Temple (and lost).
- Draper proposed to his wife 3 days after meeting her and while she had a ring on her finger.
- Draper has hung out with Fidel Castro (who apparently still owes him $20) and just about every other prominent political leader you could name.
- Draper recently joined Twitter @WilliamHDraper
This exclusive excerpt from the book discusses Draper’s efforts to bring the best practices of the venture capital world to an unlikely place: Cuba. Who knew that Castro had a sense of humor?
If you want to win an autographed copy of the book, retweet and post a comment below to enter the drawing.
PASSAGE FROM The Startup Game
During our conversation, I felt compelled to take full advantage of the fact that Fidel Castro was going to be with me all evening long. I momentarily stepped out of my role as the head of the UNDP, and in an attempt to liven up the conversation, I said, “To be honest, I’ve been to about sixty developing countries, but I’ve never seen an economy in worse shape than yours.” He shot back, “Our economy wouldn’t be so bad if your country lifted the embargo.”
The Cuban government’s human rights abuses, including torture, unfair trials, arbitrary imprisonment, and extrajudicial executions, came to mind. So I continued to prod: “The United States placed the embargo because of the human rights violations here in Cuba.”
He called down the table to his yes-man: “Carlos, do we have any human rights problems here?”
Carlos, the official who had arranged the dinner, had earnestly had us try to have us meet in a cooperative and cordial way, yet I was testing the waters to see how far I could swim. Carlos, visibly shaken, hastily replied, “No, no, Fidel, no.”
Castro continued, “By the way, if you want to talk about human rights problems, what about New York City and all of those poor people there?” He had visited New York City in 1959, at a time when he was still received as an up-and-coming leader, lunching with bankers on Wall Street, speaking to an audience of 30,000 in Central Park, and even feeding a Bengal tiger at the Bronx Zoo.
I said, “Well, we do have some poverty in New York, but our free-enterprise system encourages entrepreneurship and economic development, and has led to enormous wealth and a higher standard of living for the vast majority of Americans.” Castro’s reaction was a heated denial that free enterprise was needed for a healthy economy.
Thinking that this had gone as far as I should test it, I said, “Fidel, maybe we should talk about something less controversial, like UNDP programs here.”
“No, I’m having fun! Aren’t you having fun? he asked. I really was, so I continued. “Who do you think will win the Nicaraguan elections?” I asked him.
“Ortega, two to one,” he confidently replied.
Daniel Ortega was the leader of the Sandinista National Liberation Front-the ideology of which was in line with that of the communist party- but he faced a strong challenger in Violeta Chamorro of the anti-Sandinista alliance. “Well, I think that Chamorro’s going to win,” I said. Castro paused for a moment to savor a bite of meat that had been approved by his official food taster. “Ortega, 53 percent,” he said flatly.
I reached for my wallet, pulled out a bill, and said, “I’ll bet you $20 even that Chamorro wins.”
Castro snapped his fingers at his assistant. “Carlos, give me 20 pesos.”
After the bills were passed to him, we eyed each other again. We both knew what the other was thinking: twenty dollars is worth a whole lot more than twenty pesos. I chose not to point that out. But Castro pulled out a pen, and-with a hint of smile-signed and dated each of his bills. Instantaneously their value skyrocketed.
In diplomacy, positioning is everything. With a wink, I took out my pen and signed my bill as well, but of course, its value remained grounded at $20. We exchanged bills and sealed out bet with a handshake.
I’m pleased that Ortega’s Sandinistas ended up suffering a stunning defeat, with Chamorro winning 55 percent of the vote. I never did get my $20 back, but the Cuban representative to the United Nations approached me a few times over the next few years to say, “By the way, Fidel knows that he still owes you $20.”






