In Silicon Valley, Jim Swartz is the consummate entrepreneur, a 30-year venture capital veteran who's taken dozens of high-tech companies public. When it comes to grand prix racing, however, the former Harvard University football player is a greenhorn. His first big raceboat-the Swan 601 Moneypenny-hit the water last July for the Rolex Swan American Regatta. But those hoping to take advantage of Swartz's naivete were sorely disappointed. The Pittsburgh native-who now splits his time between San Francisco, Park City, Utah, and Martha's Vineyard-knows how to do his homework. Under the tutelage of Kimo Worthington and Dee Smith, Swartz, 62, sailed a Mumm 30 in four events last winter and spring. When he finally got his hands on the wheel of his 601, he was ready for just about anything the opposition and Mother Nature could throw his way. On the opening day of the regatta, Swartz and his crew handled the 30-knot gusts with aplomb, winning the race easily. Moneypenny won five of eight races and the Class A overall title.What attracted you to racing?I sailed a little on a Sunfish, a Hobie Cat in Long Beach Island, N.J.-we had a summer home there for 20 years. Then we moved to our summer home to Edgartown. A friend got me on a 12-Meter for a weekend thing and I loved what I saw. I love teams and I love people. So I started looking into it more. I always admired the classic beauty of the Swans. I looked hard at 12-Meters and actually ended up the partial owner of Onawa.Was a competitive team atmosphere something you missed as an adult?Not really. I'm competitive, but I'm a low-key competitor. For me it's about the challenge of doing something really well; putting everything together and succeeding. One of the good things about sailing is that you know very quickly when you've done it wrong; it can really bite you and at the end of the day you can look back and analyze what went wrong.How did you decide on the Swan 601?I got hooked up with Kenny Keith, the Swan dealer in San Francisco. I wanted a sexy raceboat, but I was also conscious of resale value. I want to daysail around Martha's Vineyard and maybe do some cruising. The whole concept of the 601 was very appealing. Kenny has been instrumental in introducing me to some very fine guys: Kimo Worthington and Dee Smith. It all flowed from there. I put the order in and the coaches said, "You know, Jim, it might be good if you had some practice before you go to the 601." So that's where the Mumm comes in?We did four regattas with it. I had a fantastic time. I think the best I did was a third in one of the regattas. I learned a ton from it. We named that boat Q because he was the head of R&D for James Bond. Was there anything that surprised you about the sport?The Mumm was really challenging because I'm not as athletic as I used to be. [In Key West] it was blowing 30 to 35 when we practiced and 30 to 32 when the first race started. But I'm a pilot also; I've done a lot of instrument flying so I'm pretty comfortable with scanning and keeping things on track. I think the most surprising thing to me was how sensitive everything is and how tiny adjustments can make a big difference. So the first race at Key West, it's blowing 30 knots and you're on the line with 13 other boats . . . It was one of the scariest things I've done. The second race I hit a boat because I got confused with Dee. He told me to duck a boat and I started down, and then he realized we weren't going to make it so he told me to come up again and I said, "Oh, hell, I can make that." I just kept going, and of course he didn't let the main out so we T-boned the guy, which was pretty unfortunate.But it didn't scare you off ?No, we hung our heads, but came back the next day. The guys were able to repair the boat and it all worked out.The 601 is a big racing machine; is it too much for an owner/driver to handle?Well, here I am, clearly an amateur driver. I think you need an above average crew. But I think it's well within the realm of the Swan sailors I've seen.Is Moneypenny customized for racing or cruising?We optimized based for racing. So we kept out the AC, for example, and some other things which are easy to put back in. But I didn't go hard over. For example it has two heads and the guys tried to talk me into taking one out, but I drew the line there. And they wanted me to take out the hot water heater, but I kept it in. Do you hope to be racing against other 601s in the future?The reason I bought it is to do one-class racing. I'm very hopeful that we can get some more here in the U.S. There are five in Europe. Some of them are coming here for Key West and Miami, and we are going to go to Europe next summer.Where do you see this program going?I've committed to the guys who run the program until next October after Porto Cervo and the Swan Cup. We'll see how we do and how much fun we're having. At that point we'll have a few options: Sell the boat and get another one, sell the boat and not do anything, convert it into a cruiser, or keep doing what I'm doing.Tell us about the name? Are you a big James Bond fan?The hull number is 61007. So that dropped in my lap and I said, "Gee, this might be fun. Let's try to do something with 007." Obviously you want a woman's name for a boat name. There were several that were ruled out on the homefront. But then I saw Miss Moneypenny. The guys came up with Odd Job for the tender and Q for the Mumm.And there's no shortage of names if you want to add to your fleet.Exactly.