Penelope Trunk (bornAdrienne Roston,^[1] December 10, 1966;^[2][3][4] legal nameAdrienne Greenheart) is an American writer and entrepreneur. Trunk published works in the early 2000s under thepen nameAdrienne Eisen and later under the name Penelope Trunk, a name she adopted in her public life.

Trunk founded severalstartup companies and provides career advice through her blog penelopetrunk.com.^[5][6] She has written columns about the workplace and the job market for several publications, including the syndicated column, "Brazen Careerist", featured onYahoo! Finance, and "The Climb," which ran inThe Boston Globe.^[7] She has also appeared on news programs such as20/20 and in segments forCNN andNPR.^[6]

Inc. magazine referred to her as "arguably the world's most influential guidance counselor" in 2011.^[8] She was included onTechCrunch's list of "30 Women Who Have Revolutionized A Male-Dominated Industry" in 2015.^[5]

Trunk was born inWilmette, Illinois and graduated fromBrandeis University in 1990, before moving toLos Angeles to pursue a career as a professional beach volleyball player.^[9][10][11] On the Women's Professional Beach Volleyball Tour she was ranked 17th in the US.^[12]

In the early-90s, Trunk was introduced tohypertext by a boyfriend who curated content for use inCD-i format.^[13][14] Once the internet became public domain, her boyfriend taught herHTML and in 1993 Trunk created her own website where she posted herhypertext works.^[14]

In 1996 she published the hypertext novel,Six Sex Scenes as Adrienne Greenheart, and was credited under her pen name, Adrienne Eisen, from 2000 onward.^{[15][16][17][18]} Written in thefirst-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.^[19][20] 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 aChoose Your Own Adventure book.^[19]

Trunk has written articles related to career advice, entrepreneurship and the evolution of the workplace for publications and news agencies such asThe Boston Globe,The Wall Street Journal,Business Week,Glamour,Marie Claire,Business 2.0,BNET andYahoo! Finance.^[6][7][21] Her blog posts were syndicated to more than 200 newspapers.^[6] She has also appeared as a guest commentator on20/20,CNN, andNPR.^[6]

Trunk blogs and provides career advice through her personal website, penelopetrunk.com.^[6]

In 2001 Trunk publishedMaking Scenes withAlt-X (a subsidiary ofUniversity of Colorado), which is a book based on pages previously published on her website.^[22] The novel was republished byEmily Books in 2012.^[23]

Trunk's second book,Brazen Careerist: The New Rules for Success, was published byWarner Books.^[1]

Trunk founded the companies math.com and eCityDeals.^[5] She co-founded Brazen Careerist, a social networking site aimed atmillennials entering the job market,^[24][25] now called Brazen Technologies.^[26]

Since moving toDarlington, Wisconsin, Trunk co-founded Quistic, an online learning company.^[27][28]

Trunk has been married twice and has two children.^[10] She moved with her family from New York City toMadison, Wisconsin in 2006, before relocating to a farm nearDarlington, Wisconsin.^[1][29]

Trunk is very open about her life and has received media attention for tweets about her divorce and miscarriage.The New York Times included Trunk'stweets about her divorce in a 2008 article about the airing of "dirty laundry" on social media.^[30]

In 2009, Trunk was preparing to have anabortion, but suffered amiscarriage during a company board meeting.^[2] She tweeted about the incident, which received widespread media attention.^[2] She was also interviewed onCNN about the incident.^[2] It was around this time, Marin Cogan recalled in an article forThe Cut, that Trunk's blog began to take on a darker tone, less appealing than the one that had made her the "Sheryl Sandberg long before Sandberg wroteLean In". Cogan came to feel she and other early career women had been "mistaken in assuming that Trunk’s brazen careerism was a feminist project in any meaningful sense."^[31]

Trunk describes herself as havingAsperger syndrome.^[32]

Trunk's name at birth was Adrienne Roston. She posted to her blog in 2007 that she legally changed her last name to Greenheart (which at times she spelled GreenHeart) because she "[didn't] want to be associated with patriarchal naming conventions."^[33]

In a 2010 interview withMagazine Electronique du CIAC (a publication by Centre International d'Art Contemporain de Montreal), she said she changed her last name from Greenheart to Eisen because she "had a big job and my company just forced me to change the name on the hypertexts."^[14]

She claims that her name change to Penelope Trunk was prompted byTime Warner when she was hired to write for them. She later adopted it in her personal life.^[14] She also toldMagazine Electronique du CIAC that her original first name, Adrienne, causes her emotional discomfort and reminds her of negative experiences during her childhood.^[14]

• Six Sex Scenes (as Adrienne Greenheart, later Adrienne Eisen) (Alt-X, 1996)

• "Making Scenes" (as Adrienne Eisen) (Broadvision, April 2001,ISBN 978-0970351708)
• Brazen Careerist: The New Rules for Success (Warner, May 2007,ISBN 0-446-57864-9)
• The New American Dream: A Blueprint for a New Path to Success (Hyperink, July 2012,ISBN 1614649928)
• The Power of Mentors: The Guide to Finding and Learning from Your Ideal Mentor (Hyperink, October 2012)

• Official personal website