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New Medium, Old Partners
This is not the first time Calacanis and Alvey have collaborated. They attended the same Brooklyn high school and started their first venture, a magazine about online services called Cyber Surfer, in 1994. Two years later they launched Silicon Alley Reporter, a magazine that covered Internet startups and served as an East Coast foil to the better-known California-based tech tomes of the late 1990s, such as Red Herring and the Industry Standard.

Silicon Alley Reporter prospered in the days of profligate advertising budgets, and it launched additional businesses, such as an events-planning division, e-mail newsletters, a website, and a radio show. Calacanis established himself as a familiar pundit of the East Coast tech boom. He served as CEO of the company, while Alvey, who built TV Guide’s website in 1995 and was a member of the team that built the first BusinessWeek site later that year, was chief technology officer.

When the market crashed in 2000, and other Internet-focused media companies went out of business, Calacanis retooled Silicon Alley Reporter to focus on venture capital. In 2001, he changed the name to Venture Reporter, ditched the advertising-based business model, and increased the price of the magazine, turning it into a high-end business-information offering. Venture Reporter charged up to $1,000 for research reports and from $1,000 to $5,000 for access to a proprietary database of information about venture capital investment and mergers-and-acquisitions activity. The makeover narrowly rescued the company from oblivion. After Venture Reporter was acquired, first by Wicks Business Media and then by Dow Jones, Alvey, and eventually Calacanis (who stuck around until 2004), decided to move on.

In early 2003, Calacanis and Alvey began to discuss new business ideas in the media sector. They’d followed the blogging exploits of two former Silicon Alley Reporter employees: Xeni Jardin, who is a contributor to the popular collaborative blog Boing Boing, and Rafat Ali, who publishes PaidContent.org, a blog about emerging new-media business models. Calacanis saw the validity of one of those models as he observed the immediacy of Jardin’s and Ali’s postings, the value of their information, and the loyalty of their readerships. “It wasn’t hard to see that there was this new model emerging where writers are unfiltered and readers actually like it as much as, or perhaps even more than, they like magazines,” he says. “And they certainly appreciate that the content is available on a more regular basis.”

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