Penelope Trunk is co-founder of Brazen Careerist, a career management tool for next-generation professionals. This is her third startup. Each company Penelope built was focused on a community. Her own career path has had twists and turns and in a world where straight, safe career paths are nowhere to be had, Penelope appreciates the power of managing oneself through community.

Penelope’s career began in Los Angeles, where she played professional beach volleyball. She then went to graduate school for English. During that time she learned HTML which allowed her to get a job in the marketing department at Ingram Micro.

After a stint in the Fortune 500, she went to a few smaller software companies and then started her own company, Math.com, a math-tools resource for the teaching community funded by Encore Software. She sold that company for a small sum, and founded eCitydeals, an online auction service for city governments, which was funded by Shelter Ventures, and was shut down in the dot-com bust.

During this time, Penelope wrote a column for Business 2.0 magazine about her experiences as a startup founder. She relocated to New York City and after only a few months at her next startup, she found herself a block from the World Trade Center when it fell.

She decided to be a full-time writer so she did not have to leave her apartment. And she focused on giving career advice instead of writing about herself. At that point, generation Y was entering the workforce and they were looking for advice to tell them how to steer a career that accommodates their lives: old career advice was irrelevant to them.

Penelope started writing career advice for a new generation of workers. Today Penelope is the author of a bestselling career advice book for generation y and the number one career blog.

Penelope spent three years publishing research about how to figure out where to live. After delving into reams of research on economic development and positive psychology, Penelope moved to Madison, WI, where she did not fit in well, but she fell in love with a farmer.

Now she lives on a farm in southwest Wisconsin. The closest town is Darlington, which has 2000 people in it. She is acclimating to rural life, a process which probably will include homeschooling, if she can get enough guts to do it.