AdBrite’s Adventures in Sequoia-land

I somehow missed this cheerfully strange article from the WSJ back in January. No subscription is required, and this piece, on Philip “Fucked Company” Kaplan’s adventures in venture capital via his AdBrite outfit, is fun reading:

The $4 million investment by Sequoia [in Kaplan’s AdBrite] brings together a venture firm that backed high-profile dot-com busts such as Webvan Group Inc. and eToys Inc. with a voluble critic of those firms. Sequoia also backed both Yahoo and Google, both AdBrite competitors, and still holds a multibillion-dollar stake in Google.
Mark Kvamme, a Sequoia partner who has joined AdBrite’s board, says neither issue proved an impediment to investing in AdBrite — even after Mr. Kaplan cracked a Webvan joke at a meeting with Sequoia’s partners. “I hate to say it, but he was right” about many dot-coms, Mr. Kvamme says of Mr. Kaplan. Mr. Kvamme calls Mr. Kaplan a “world-class entrepreneur” who combines a good business head with computer-programming skills . “We like working with the irreverent guy,” he says.
… AdBrite and Sequoia are strange bedfellows. F — edCompany’s home page contains links to nude “FC girls,” and its message boards host sexually explicit exchanges. Mr. Kaplan runs another Web site ( that hosts photos, many sexually explicit, taken with cellphone cameras. Mr. Kaplan brags about his arrest for breaking a window with a slingshot as a high-schooler and the $3,000 fine he received for playing drums too loudly in his apartment in New York, where he lived until last year.
Mr. Kaplan says he’s wearing pants in the office these days, but laughs about running a growing company. When a newly hired saleswoman asked when her training would start, his response was “Training?” After an airline lost his AdBrite sign as he was traveling to an ad-industry conference in November, Mr. Kaplan spent the night creating a replacement from Kinko’s photocopies and a supermarket-purchased painting set for kids.
Mr. Kaplan spent three months last year working out of Sequoia’s offices until he secured office space for AdBrite. Mr. Kvamme jokes that his colleagues were eager to see Mr. Kaplan leave. “He ate a lot of our food,” says Mr. Kvamme. “The guy is a high-octane guy.”

At the risk of drawing a moral here, I love the flexibility shown by Kvamme and the partners at Sequoia. They looked past how much of an irritation Kaplan had been (and was being?), and they saw a business that worked run by a guy with high-energy, good ideas, and, yes, irreverence. Where many venture firms would have run and hid, Sequoia invested. Now there is useful contrarianism for you.