About Penelope Trunk
Born 1966. Penelope Trunk is an American writer, businessperson and author.
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. She was included on TechCrunch's list of "30 Women Who Have Revolutionized A Male-Dominated Industry" in 2015. On the Women's Professional Beach Volleyball Tour she was ranked 17th in the US.
Career
Hypertext 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. 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. Her blog posts were syndicated to more than 200 newspapers. The novel was republished by Emily Books in 2012.
Trunk's second book, Brazen Careerist: The New Rules for Success, was published by Warner Books. now called Brazen Technologies.
Since moving to Darlington, Wisconsin, Trunk co-founded Quistic, an online learning company.
Personal life Trunk has been married twice and has two children.
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's tweets about her divorce in a 2008 article about the airing of "dirty laundry" on social media.
In 2009, Trunk was preparing to have an abortion, but suffered a miscarriage during a company board meeting.
Trunk describes herself as having Asperger syndrome.
Name changes
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."
In a 2010 interview with Magazine 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."
She claims that her name change to Penelope Trunk was prompted by Time Warner when she was hired to write for them. She later adopted it in her personal life. She also told Magazine Electronique du CIAC that her original first name, Adrienne, causes her emotional discomfort and reminds her of negative experiences during her childhood.
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Important facts
People in Penelope Trunk's life
Named in this biography and alive at the same time
Contemporaries
People whose lives overlapped Penelope Trunk's
Frequently asked questions
Who is Penelope Trunk?
American writer
When was Penelope Trunk born?
Penelope Trunk was born on 10 December 1966 in Wilmette.
What is Penelope Trunk's occupation?
Penelope Trunk is a writer, businessperson and author.
What nationality is Penelope Trunk?
Penelope Trunk is American.
Sources & further reading
Cite this page
APA: Biography.guide. (2026). Penelope Trunk. https://biography.guide/penelope-trunk/
MLA: "Penelope Trunk." Biography.guide, https://biography.guide/penelope-trunk/.
Chicago: "Penelope Trunk." Biography.guide. https://biography.guide/penelope-trunk/.
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