Neal Dempsey, venture capitalist and expedition leader, let out an easy, good-natured laugh, his eyes alight with a little gleam of mischief. We, his climbers, were sitting at the end of a long table beneath the thick cedar beams of the Paradise Inn dining hall at Mount Rainier National Park, picking the last bits of bourbon buffalo meat loaf off our dinner plates.
"We don't have a set agenda," Dempsey told us. "We just thought summiting Rainier would be something fun to do. Venture firms tend to do all this traditional crap, like golf, tennis, dinners, plush resorts, blah, blah, blah. Our idea was, why don't we do something different? Something hard, but not so hard that you hate it, but that really gets you out there."
Fair enough. I was here chasing down one of the more tenacious trends whelped by the ever-expanding adventure-travel beast--in this case, the trend to appropriate arduous and sometimes extreme activities as a self-improvement regimen for rudderless (but bullish!) corporate desk jockeys across America. I'd been asking Dempsey if there was any other agenda for the weekend ahead besides getting our crew of 12--most of them business executives, all here at his invitation--to the top of Washington's 14,410-foot, no-bullshit volcano. Were there new associates to haze, deals to be struck? Was this a motivational exercise, or just a big PR stunt? No, not really, he maintained in his charming way.
Dempsey may have grown up poor in Tacoma, but now, at 60, a married father of two grown kids and a principal at Bay Partners, a Silicon Valley venture-capital firm, he needn't fear going without. Bay Partners isn't a marquee rainmaker the way Kleiner, Perkins, Caufield & Byers is, but the 26-year-old firm has done quite well for itself and its investors. It manages five investment funds together worth more than a billion dollars, and unlike many of its rivals, during the market run-up of 1998-99, it remained focused on high-tech infrastructure rather than dotcoms. As a result, since the digital bubble began to deflate back in early 2000, Bay Partners has suffered less than most of its VC brethren.
A lean, six-foot-tall man with runner's legs and genetically mussed gray-brown hair, Dempsey reflects the firm's anti-glam yet adrenalized approach. He's a good listener, likes to kid ya, and has the winning habit of inserting [Your Name Here] as he's making a point. In a business that demands upbeat charisma, he's an admired player-coach, a wily veteran who's still got game.
True, lots of other moguls are known for their high-adventure hobbies: Daredevil pilot and Oracle CEO Larry Ellison races sailboats against Hasso Plattner, cofounder of the German software giant SAP. Martin Brauns, head of Interwoven, the self-
described "fastest-growing software company in Silicon Valley," competes in Hawaii's Ultraman World Championship (triple the Ironman distance). Jim Clark, the serial entrepreneur lionized in Michael Lewis's best-seller The New New Thing, is a sailor, a pilot, and a scuba diver who uses a rebreather to commune with whale sharks. Yet even in this elite company, Dempsey's got impressive bona fides. He's finished more than 50 marathons since he began running in 1981. He went on his first "CEO climb"--summiting Rainier with the president of Rainier National Bank and other execs as part of a fund-raiser for the American Lung Association--back in 1988. He's been weathered off Aconcagua and Mount McKinley, only to summit both later, and has topped out on six of the Seven Summits--all but Everest.
Sitting in the dim light of the Paradise Inn, it was dawning on me how Dempsey had managed to help guide Bay Partners with such a steady hand. A far more agile thinker than your average sports metaphorslinging financier, he knows intuitively when and how to buy into (and out of) the hype. And right now, he was keeping me guessing. Not a fan of ropes courses and other New-Age-meets-boot-camp "off-sites" favored by Fortune 500 companies trying to "forge" business teams ("I never thought those things were worth a shit"), Dempsey may have devised a fresh twist on the corporate-retreat-as-adventure-vacation. His partner in the firm, Bob Williams, who was also along for this summit attempt, calls it "purposeful indirectness"--
assembling a heterogeneous group and seeing what connections emerge. Or, as Dempsey told me later, "I liked the idea of Rainier for the challenge of it, but also the bonding of these people who didn't really have a previous relationship other than that some of them knew me. Well, all of them knew me--except you."