To be a part of his exclusive investment club you had to have a minimum net worth of at least a million dollars, or have a famous name, according to Rivlin. Countless of the Internet's rising stars joined Angel Investors and its successor companies. Cobbled from myriad business journals is a small list from among many of Conway's chosen: Dean Morton of Hewlett Packard, golfer Tiger Woods, Stanford University Engineering Dean Jim Gibbons, Twitter CEO Biz Stone, entertainer MC Hammer, venture capitalist Frank Quattrone, and Salesforce CEO Marc Benioff.
For a man who made his fortune investing in the hottest names in tech, Conway is often described as a bit of an anti-tech Luddite. Not relying on product knowledge, his strategy boils down to this: Conway trusts his first impression of a startup's CEO. He goes with his gut, as he explains in a free Stanford YouTube class featuring Conway.
And though sometimes his companies would fail, the successes more than made up for those failures — so much so, that he had to expand. Conway started new LLCs to handle his expanding investments. Angel Investors II started with $150 million, according to Rivlin. SV Angel III and IV were no slouches either, starting with investments of $40 million apiece, according to SEC filings for the companies.
The number of investments from Angel Investors at the time of Rivlin's 2001 book was already well over the hundreds. And the most recent numbers for SVAngel, from 2011, list the number of startups they've invested in at 290 companies.
Conway disciple David Lee officially took over as head of the Angels last year, according to California business filings, but several sources indicate Conway is still the largest investor in the various "Angel" branded companies.
Conway is also the head of a long list of other shadowy businesses, all incorporated in Delaware for its lax tax and regulatory policies. Among the more than a dozen companies just in San Francisco that list Conway as president, partner, founder, or agent-of-service — for which most have little information publicly available — are SV Angel Management Holding, RC Chirp Fund LLC, RC Chirp Management LLC, 2000 Washington Street, 2006 Washington Street, Conway Family Foundation, and Magillicutty LLC.
What separates Angel Investors, though, from the usual investment angels, is Conway's unique way of leveraging his network, known as his "Rontourage." Hundreds of tech luminaries and celebrities tied to Conway's Angel companies have an understanding that they will trade favors, according to Rivlin's book.
"The only caveat, whether you joined a side fund, an advisory board, or Angel Investors, was that you should lend a hand when you could," Rivlin wrote. "If you're in the club, you can do someone a favor and trust that somehow you're going to get repaid for that favor," tech entrepreneur Jad Duwaik told Rivlin.
That strategy goes a long way towards explaining what Conway is doing in San Francisco.
CEO OF SAN FRANCISCO
Mayor Lee nows seems to be getting the royal Conway treatment, and the companies Conway invests in are getting strong support from the Mayor's Office at City Hall, from the tax breaks that Twitter and Zynga received last year to this year's unsuccessful effort to maintain Ainbnb's exemption from the transient occupancy tax (a decision made by the Treasurer/ Tax Collector's Office, which defied Lee's public lobbying on the issue).
SV Angel has investments or equity in over 103 total San Francisco startups, according to SV Angel documents leaked to Fortune last year, including Airbnb, Digg, Formspring, Wikia, EventBrite, Zynga, StumbleUpon, Justin.TV, and a little company called Twitter.