Andrew Rasiej
Who
A political candidate (he ran for public advocate), campaign advisor (he's worked with Hillary Clinton and Howard Dean), online entrepreneur (he founded a music dotcom), and nightlife impresario (he founded Irving Plaza), Rasiej's worn many hats over the years.
Backstory
Raised by Polish immigrant parents in New Jersey, Rasiej says he felt so guilty that his parents paid for his private high school education that he insisted on going to college at tuition-free Cooper Union. After graduating, he founded a consulting firm that advised non-profits on real estate matters. When he noticed a client's theater a block from Union Square and realized the space would be perfect for concerts, he launched the rock venue Irving Plaza in 1990. (He's since sold his stake in the venue.) Rasiej turned his attention to the web during the dotcom boom of the late '90s and launched the Digital Club Network to record and sell music from live shows. (The company was later sold to eMusic.)
Since then, Rasiej has dedicated his time to various political, non-profit, and technology projects. During Howard Dean's 2004 presidential bid, Rasiej acted as the chairman of the Dean's Technology Advisory Council. In 2005, he jumped into politics himself, mounting a bid for public advocate and losing in the Democratic primary to Betsy Gotbaum. (One of his campaign platforms: He said he'd wire the city with free/low-cost WiFi.) He's also launched a two-day annual event known as the Personal Democracy Forum, and founded the political group blog techpresident.com with editor and writer Micah Sifry.
On the side
When Rasiej was running Irving Plaza, he founded the New York Nightlife Association to represent the city's bars and clubs. (The group is currently headed up by David Rabin.) In the late '90s, he started MOUSE, a non-profit group that provides technology assistance to public schools.
Personal
Rasiej and his girlfriend live in a loft at 225 Lafayette Street; his neighbors in the building include Tyra Banks and Stephen Gan. In 2004, he listed his previous place, a four-story townhouse on Leroy Street, for $8.95 million. (He had paid $2 million for it just two years earlier.) The house featured a Zen garden, koi pond, roof-top lawn, two-car garage, and elevator.