In the early 1980s Rappaport was senior editor of EDN Magazine, which covers new technologies and electronic component products. He was also a research physicist with Panametrics, Inc.
In 1984 Rappaport founded the Technology Research Group (TRG), a Boston-based strategy-consulting firm that worked with such companies as Alcatel, AT&T, IBM and Intel. He served as TRG’s president until 1997.
From 1985 to 1996, Rappaport invested in a number of start-up technology companies such as Actel, Atheros Communications, Genoa Corp, MMC Networks, Silicon Architects, Silicon Image, Transmeta, and Viewlogic. He also founded the Massachusetts Center for Technology Growth, a private economic-development organization. And he served as director of the Massachusetts Microelectronics Center.
In 1996 Rappaport joined August Capital, an information-technology venture-capital firm based in Menlo Park, California. He remains affiliated with the company to this day. Over the course of his professional career, Rappaport has served on the boards of more than 40 public and private companies.
A committed Democrat and a socialist, Rappaport has established himself (along with his wife, the philanthropist and political activist Deborah Rappaport) as one of the largest donors to Democratic Party candidates and causes. Between 1999 and 2008, he contributed $340,139 to candidates and political action committees at the national level. In addition, he and his wife have given millions of dollars to organizations that promote Democrat objectives and policies. In 2004 alone, the Rappaports gave at least $2.66 million to Democratic causes, including $1.1 million to the New Democratic Network, a leftist think tank and advocacy organization.
Andrew Rappaport is secretary of the Rappaport Family Foundation (RFF), which he and his wife established in 2002 as a vehicle by which to administer their charitable donations. Between 2004 and 2008, RFF gave $850,000 to People for the American Way, $700,000 to the Center for American Progress, and $323,000 to the anti-war group Project Billboard. In 2006 RFF sent $100,000 to the Tides Center, which in turn (on instructions from RFF) funneled the money to Allied Media Projects, an anti-corporate community-media organization where ACORN founder Wade Rathke sits on the board of directors. As of 2006, RFF’s assets totaled $7.6 million.
In 2003 the Rappaports created a political venture-capital firm called Skyline Public Works (SPW), which provides office space, financial advice, and capital for start-up activist organizations. Traditional venture capital firms furnish seed money for start-up businesses in hopes of eventually earning a significant return on their investments when the companies grow bigger and more profitable. By contrast, the Rappaports measure their SPW-related “profits” not in monetary terms, but rather by the degree of political influence the start-ups are able to acquire.
During the 2004 election season, the Rappaports worked hard to persuade 18-to-30-year-olds to become politically active and to support Democrat presidential candidate John Kerry. Through Skyline Public Works, the couple contributed at least $5 million to the groups Music for America and Punkvoter.com, which targeted young voters. In addition, the Rappaports gave $600,000 to the 21st Century Democrats to support efforts (in four states) to register young voters and persuade them to vote Democratic.
Also in 2004, the Rappaports gave $1 million to fund a series of Spanish-language ads — created by the New Democratic Network — promoting the Democratic Party. Moreover, the couple helped finance that year’s national convention of the Daily Kos.
In October 2004 the Rappaports announced that they were “deeply outraged” over Sinclair Broadcast Group’s (SBG) decision to air the film Stolen Honor, which was highly critical of John Kerry. In an effort to counter that film’s message, the Rappaports purchased the rights to the pro-Kerry film Going Upriver: The Long War of John Kerry, and offered SBG more than $1 million to air the latter without commercial interruption.
After Kerry was defeated in the 2004 presidential election, the Rappaports were contacted by New Democratic Network president Simon Rosenberg, who urged them to meet with Democrat political operative Rob Stein. Not long thereafter, the Rosenbergs attended a PowerPoint presentation where Stein explained how the Left could create a “message machine” that would help rebuild and energize the liberal/left movement. The proper course of action, he counseled, would be to emulate the tactics of conservatives, who were allegedly spending $300 million per year on think tanks, advocacy groups, and media organizations designed to influence public opinion. Andrew Rappaport’s immediate response to Stein’s revelation, as later reported in The New York Times, was: “Man, that’s all it took to buy the country.”
Influenced by Stein’s presentation, the Rappaports decided to focus less on contributing to Democratic Party candidates during subsequent election seasons, and more on financing leftist issue- and grassroots-advocacy groups that would work to shape public opinion on key issues every day of every year, not just during election cycles. Toward that end, in October 2005 the Rappaports used Skyline Public Works as the funding vehicle to establish the New Progressive Coalition. “At the end of the day,” Mrs. Rappaport said, “we’re trying to get away from the election-to-election mentality, because we’ve been there, done that, and it doesn’t work. Instead, the key as we see it will be building long-term capacity on the local level and incubating more and more broad-based organizations to take the progressive movement to the next step.”
Over the years, Andrew Rappaport has given money to the political campaigns of many Democrat candidates, most notably Barbara Boxer, Sherrod Brown, Tom Daschle, Howard Dean, John Edwards, Al Franken, John Kerry, Barack Obama, and Harry Reid.
The Rappaports are financial sponsors of the Huffington Post. They also gave $70,000 to ActBlue, a PAC that collects donations and then distributes the money to Democratic political candidates, sometime prior to January 2008.