Penelope Trunk
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Penelope Trunk

Penelope Trunk (born Adrienne Roston, December 10, 1966; legal name Adrienne Greenheart) is an American writer and entrepreneur. Trunk published literary works including electronic literature in the 1990s and early 2000s under the pen name Adrienne Eisen and later under the name Penelope Trunk, a name she adopted in her public life.

Trunk founded several startup companies and provides career advice through her blog penelopetrunk.com. She has written columns about the workplace and the job market for several publications, including the syndicated column, "Brazen Careerist", featured on Yahoo! Finance, and "The Climb," which ran in The Boston Globe. She has also appeared on news programs such as 20/20 and in segments for CNN and NPR.

Inc. magazine referred to her as "arguably the world's most influential guidance counselor" in 2011. She was included on TechCrunch's list of "30 Women Who Have Revolutionized A Male-Dominated Industry" in 2015.

Trunk was born in Wilmette, Illinois, and graduated from Brandeis University in 1990, before moving to Los Angeles to pursue a career as a professional beach volleyball player. On the Women's Professional Beach Volleyball Tour she was ranked 17th in the US.

In the early-90s, Trunk was introduced to hypertext by a boyfriend who curated content for use in CD-i format. Once the internet became public domain, her boyfriend taught her HTML and in 1993 Trunk created her own website where she posted her hypertext works.

In 1996 she published the hypertext fiction Six Sex Scenes as Adrienne Greenheart, and was credited under her pen name, Adrienne Eisen, from 2000 onward. Written in the first-person, the semi-autobiographical story focuses on the love life of a young Jewish woman, interspersed with flashbacks to her childhood, both of which are fraught with dysfunction. The reader starts the story in a section titled "Therapy", and is presented with a series of options at the end of the section in the form of hyperlinks that lead to other sections of the story, similar to a Choose Your Own Adventure book.

Trunk has written articles related to career advice, entrepreneurship and the evolution of the workplace for publications and news agencies such as The Boston Globe, The Wall Street Journal, Business Week, Glamour, Marie Claire, Business 2.0, BNET and Yahoo! Finance. Her blog posts were syndicated to more than 200 newspapers. She has also appeared as a guest commentator on 20/20, CNN, and NPR.

Trunk blogs and provides career advice through her personal website, penelopetrunk.com.

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