Bill Draper On His $20 Bet with Fidel Castro

It surprised me when I saw [Fidel]’s not tall, but he came into the room and seemed bigger than life, because he’s got the uniform and that presence.

Danielle Sacks

Interview by

Spring 2012. Silicon Valley
Digital recorder

Read her Bill Draper profile in Fast Company magazine




Danielle Sacks: Typically when I’m doing a profile I always try and get the subject in their natural element. Usually you want something that is a window into who they are.

David Gerlach: That’s Danielle Sacks. She’s a senior writer for Fast Company magazine.

Danielle Sacks: So in the case of Bill Draper, I went to his office in San Francisco and his mahogany bookshelves were just–the thing that struck me–they were just filled with photograph after photograph of Bill Draper with famous person after famous person. Before we sit down and get comfortable and get into formal interviewing mood, I’ve got to prompt him to tell me about some of these photographs.

Danielle Sacks: Do you want to take me through some highlights? I see several Presidents of the United States here….

Danielle Sacks: So I quickly fumble in my purse and get my tape recorder out.

Bill Draper: That’s me telling them what to do. I’m telling him what to do, and he didn’t do it.

Danielle Sacks:  Bill Draper is considered the godfather of venture capital and he’s one of the few patriarchs of a dynasty in Silicon Valley.

Danielle Sacks: So why did you meet President Obama?

Bill Draper: I met him because my daughter is a strong Democrat and she worked for Obama. These guys are Jeb Bush, and that’s Mitt Romney, and Meg Whitman and John McCain.

Danielle Sacks: Where was that?

Bill Draper: Palo Alto. We got the Pope; he blessed the UN programs for me. And Sandra Day O’Connor. She’s a good friend of ours.

Danielle Sacks: Then I see Bill Draper and his wife in a photograph next to a gentleman with a long grizzly beard in army fatigues, and I suddenly realize Bill is standing next to Fidel Castro. [Music: ]

Bill Draper: He’s a charming guy. We spent five hours together. It surprised me when I saw he’s not tall, but he came into the room and seemed bigger than life because he’s got the uniform and that presence, that stage presence.

[Sound clip of Fidel Castro giving a speech]

Bill Draper: Now he’s quite sick, I think.

[Music:] David Gerlach: So just how did a venture capitalist end up at a dinner with Fidel Castro? Well after more than 20 years investing in technology, President Reagan named Draper the head of the Export-Import Bank in 1981. Five years later he was tapped for a big position at the United Nations.

Bill Draper:  I was with the UN. I ran this large aide program, the UN Development Program. I went down to Cuba. We had a resident representative in each country. And anyway, he gave a dinner at his house in my honor and Castro came.

David Gerlach: So men began talking and it wasn’t long before Draper let Castro know exactly what he thought about the state of Cuba.

Bill Draper: In the exchange, I said, “It’s honestly the worst economy.” I was really truthful. “This is the worst economy that I ever encountered.” And I’ve seen lots and lots of developing countries. And he immediately shot back, “It wouldn’t be so bad if your country didn’t have these sanctions and embargoes.” After saying that, I shot back, “Hey, the US wouldn’t have those sanctions if it weren’t for your human rights record.” And all these people are listening. I’m a pretty direct guy. And he said, “Human rights record? Carlos, do we have a human rights problem? “No, no, Fidel.” “And what about New York, all that poverty there? I was just there.” He had just been there. He brought his own chickens to eat. Live chickens. I said, “It’s true in New York we have a lot of poverty, but still there’s no military presence like there is here in Havana.” And he said, “Military presence? Carlos, do we have military presence?”

And then I said, “Maybe we ought to talk about something less controversial.” And he said, “No, I’m having fun.” So I then I said, “Okay, I’ll bet you on the Nicaragua election.”

David Gerlach: Now just to provide historical background here: Draper and Castro met in 1990. It was just months before the stunning election of Violeta Chamorro over Daniel Ortega. Let’s put this in perspective: Chamorro was favored by the United States and Bill Draper while Ortega was backed by the Soviet Union and Castro’s cuba.

Bill Draper: “Ortega 2-1,” he said. And then I said, “I’ll bet you $20.” And he said, “Okay, Carlos give me 20 pesos.” And he knew and I knew but I didn’t say anything. I pulled out my wallet, and he got the 20 pesos, the two 10 peso notes.  And before handing them over, he pulled out his pen and he signed both of them and they went way up beyond $20, and he winked. Not wanting to be outdone, I pulled out my pen and signed my money, which stayed exactly the same value. And we traded.  I still have those two 10 peso bills on display in our living room at the house.

David Gerlach: That’s Bill Draper on his $20 bet with Fidel Castro. I want to thank Danielle Sacks for bringing us this interview. And I guess I’ll let the cat out of the bag: Danielle is my lovely wife. She’s also a great journalist. And what we’ve been listening to is an outtake from her latest article in the July/August issue of Fast Company magazine. It’s a profile called “The Drapers of Silicon Valley.” Check it out. Thanks as well to Amy Drozdowska for producing this Blank on Blank with me. Our sound logo comes to us from Jeffrey Alan Jones. And for all the journalists, interviewers, authors and documentary filmmakers listening: we want to hear your lost interviews. So drop us a line to interviews@blankonblank.org. Blank on Blank is distributed by the Public Radio Exchange, PRX.org.  That’s all for now. I’m David Gerlach. Keep listening.

PhotoLas Razones de Cuba via Flickr

Music: Ellen Allien “Zauber” | Belle and Sebastian  “Consuelo” | Goran Bregovic “Lullaby” | John Clarke “Revolution”