John Doerr has three familiar investing personas: the naive enthusiast who backs gee-whiz toys such as the Segway; the Sand Hill Road messiah who's saving the planet with green technology; and the prescient genius who made a fortune for himself and his investors by spotting technology phenomena such as Google. The Kleiner Perkins partner is endearing, saintly and brilliant in roughly equal measure. Which makes all the more jarring the reminder today, in an investigative piece by the Wall Street Journal, of Doerr's involvement in one of Silicon Valley's sleazier ventures, myCFO. The piece is long, but the key quote from Doerr's is below.

Here's a quick recap. myCFO, largely forgotten now, provided financial services to the wealthy; it was backed by Kleiner Perkins; the board included the legendary Jim Clark, Cisco's John Chambers, and, in a particularly active role, John Doerr. After the bust, the dream of a modern private bank — catering to a modern executive's financial needs, conveniently, online — gave way to a more prosaic business model. myCFO main source of revenue came from fees for a tax dodge which created artificial losses which the venture's wealthy clients could offset gains, for instance, on stock sales.

There's no indication that the continuing investigation, by the Internal Revenue Service and the Manhattan District Attorney, will touch John Doerr himself. But the Journal, which puts the story on its front page, has obtained email correspondence which will at the very least tarnish Doerr's carefully burnished reputation. Even the IRS signalled it was clamping down on obvious tax dodges, Doerr was still encouraging myCFO's own schemes.

Mr. Doerr was a booster for the firm's tax strategists. In response to Mr. Doerr's 2001 email lauding the tax team for its performance — which he sent on Sept. 11, 31 minutes before the first plane struck the World Trade Center — the tax team's leader reported landing $4.5 million more in fees. Five days after 9/11, Mr. Doerr replied: "This is AWESOME news, particularly during a week marred by national tragedy.... Please keep me posted." [Fling with tax shelters haunts Silicon Valley, in the Wall Street Journal.]