Schiff, who in fact does have a business plan, is angling for $5 million from "angel" or venture investors to turn invest-o-rama, described as a "personal finance portal," into "the leading Internet directory for investors."
Starting Thursday, New York City native Schiff goes live with a $20,000 billboard on Highway 101 north of the Ralston Avenue interchange in Belmont, not far from the headquarters of Oracle.
"I'm building investorama.com into the Yahoo of personal finance," the billboard boasts brashly. "VCs & angels email: firstname.lastname@example.org."
"We wanted to announce it in a big way so everyone knows how serious we are about it, how boldly we think about doing it," said Schiff, who in January amicably left iVillage, where he worked on the Armchair Millionaire investing section. That area is a joint venture of iVillage and personal finance firm Intuit.
"Maybe invest-o-rama is an iVillage of money," he muses.
Schiff, 29, hopes the billboard will make him a fixture in Silicon Valley "at least for 20 days," according to an aptly named corner of the site, invest-o-rama.com/hype.
Schiff says he's looking not just for capital but for partners, particularly the large Internet media companies that might make flesh out invest-o-rama's content, send visitors, or make strategic investments.
Schiff is paying for the 14-foot by 48-foot billboard with some of the cash he pocketed in iVillage's recent IPO.
As CEO, Schiff is fronting for Douglas Gerlach, who has quietly run Invest-o-rama in his spare time for four years. They have big plans for expanding it beyond pointers to thousands of sites for individual investors, promising chat rooms and "tools for entry-point investors." It's a growth opportunity, they argue, because few investors are online today.
Invest-o-rama founder Gerlach, who has written two books about online investing, describes himself as "an investing hobbyist for almost a decade."
Schiff balks at the suggestion that plastering his face on a billboard is a New York kind of thing to do.
"Highway 101 gave me the idea," he said, noting the proliferation of techie billboards along the Bay Area's Bayshore Freeway. "They're very personal billboards. They're fun. One of the things I discovered was that business should have an element of fun to it. But I realize it's very 'out there.'"
In fact, the stretch of 101 between San Jose and San Francisco sports plenty of tech-oriented billboards to grab the attention of commuters--fast Internet service, cell phones, getaway ads from airlines.
One location near Oracle's headquarters regularly displays ads from Oracle competitors trying to hire its employees, and Excite has done a series of billboards just north of San Francisco International Airport. When a high-tech trade show hits San Francisco, the billboard locations between SFO and the city fill up with technology vendors' ads targeting convention-goers.
Invest-o-rama imagines that its strategy, and not just the billboard, "will marry the best of the East Coast with the Internet powerhouses and venture capital talents of the West Coast."
If only the money people read billboards?.