The Team
Penelope Trunk
Penelope Trunk has been building online communities since the mid 1990s. She climbed corporate ladders in the software marketing industry and then founded three companies of her own.
Penelope began writing business advice when Fortune magazine published an open call for a woman to write about her own life as an executive. Penelope auditioned with a piece about her brother’s lame business ideas, and a piece about her boss’s sex appeal, and she won the job. Today, she is a columnist at Boston Globe, and her syndicated column runs in more than 200 publications worldwide.
Penelope has spent roughly ten years each in Chicago, Boston, Los Angeles and New York City. Recently, taking her own advice about how to leverage scientific research to choose a job and a place to live, she landed in Madison, Wisconsin. She spends a lot of time digging her car out of snow.
Penelope is dedicated to helping people find success at the intersection of work and life, because that’s what she wants for herself. She thinks of career advice as a group effort, so please email her. Or at least check out her blog, where she posts daily tips for making work life and personal life one happy, synchronized adventure.
Ryan Healy
After graduating from Penn State’s Smeal College of Business, Ryan Healy spent a year working as a consultant with IBM Global Business Services. During that time he developed an interest in Human Resources and Recruiting issues, specifically as they related to Generation Y.
After six months on the job he decided to make his voice heard and founded the Generation Y career blog, Employee Evolution, along with Ryan Paugh. The blog has appeared in numerous publications, including The Wall Street Journal, The New York Times and Business Week. Healy has also been featured as a spokesperson for Generation Y on CBS’s 60 Minutes.
In September 2007, Healy left IBM and moved to Madison, Wisconsin to start Brazen Careerist. He speaks with companies, organizations and non-profits on a variety of career and generational specific topics.
Outside of technology, blogging, and new media, Healy has a passion for family, friends, jogging, reading, Chipotle burritos, and all things Boston Sports.


Ryan Paugh
Ryan Paugh graduated from Penn State University in 2006 with a Bachelor’s in Journalism. He joined Merck & Co, Inc. in the corporate communications field, where he became interested in workplace issues facing Generation Y. He also took an interest in how social media can impact the way we approach our careers. He founded Employee Evolution with Ryan Healy, where he found an outlet for his curiosities.
Paugh currently lives in Madison, WI and is a co-founder of Brazen Careerist, Inc. His passion is making Brazen Careerist into a community for young professionals to make their voices heard.
Paugh has been featured in The Wall Street Journal and The Associated Press. He speaks to companies, organizations and students about issues affecting Generation Y and how to leverage social media to better your personal and professional lives.


Monica O’Brien
Monica O’Brien was born in Germany and spent her childhood jet-setting around the world with her Air Force parents. Her travels include most of the US, Europe, Guam, Japan, South Korea, Australia, and the Philippines.
Monica graduated from Truman State University in 2006 with a BS in Computer Science. After graduation, she spent 16 months at Caterpillar, Inc, where she consulted the manufacturing management team to implement technology solutions throughout the Joliet, IL facility. Later, she moved to Trading Technologies, a fast-paced software company, as a software quality engineer on futures trading software. She currently commutes between the Brazen Careerist office in Madison, WI and Chicago, IL, where she lives and attends the University of Chicago Graduate School of Business as an MBA candidate.
Monica writes about personal and professional development at her blog Twenty Set and contributes regularly to other popular blogs in her niche. She has a passion for helping young people deal with the difficult transition to adulthood, and often writes candidly about the hard-hitting life decisions everyone must face eventually. In her spare time, she also enjoys running, photography, fashion, and spending time with friends.


Photis Patriotis
Born in Bulgaria, Photis Patriotis moved to Philadelphia with his parents, scientists who came to the United States for its opportunities. From them he learned the importance of risk taking and always reaching for his goals. The tough crowd and tight-knit social atmosphere of Philadelphia taught Photis how to fight for what he wanted and maintain strong, life-long relationships, both personally and professionally.
Photis enjoys fast-paced, exciting work environments in a variety of fields. He has worked with cancer researchers at Fox Chase Cancer Center and at Columbia University to develop high-tech software. After graduating from college he spent three years working for Toll Brothers, Inc. in the home construction & manufacturing industry where, by the time of his exit, he was leading million dollar engineering projects.
Photis loves to travel. He has toured the United States with a punk rock band, and often travels back to his home countries of Bulgaria and Cyprus. Some of his other passions include motorcycling, quality seafood, and feverous argument and conversation.

Dan Healy
Dan graduated from The Ohio State University with a BS in Business Administration, and a specialization in Marketing. In 2005 Dan started his first company called Sloopy Holdings Unlimited where he oversaw sales and new business development. Dan also gave guest speeches to business and entrepreneurship classes at Ohio State.
Dan recently moved to Madison, WI to join the Brazen Careerist team, and is dealing specifically with customer relations and advertising.
Dan’s personal interests include travelling, golf, reading and family.


Jay Wigley
Jay Wigley is the old guy in the office–well, he’s older than everyone else–well, probably. Not sure.
Jay began his career at the Naval Academy, where he learned lots of history and literature and just a little engineering. And when he graduated, he knew that left up to him, he’d spend his days reading and writing, and just be all about the written word, all the time. And then he took an almost-twenty-year detour through various engineering jobs, working with really boring products like plastic tubes, and really interesting stuff like positron emission tomography scanners, and rockets. Really, rockets. One day he found some interesting career advice, followed it, and now he’s back on track, working with writers and readers, and having fun figuring out how online media can make everyone’s life a little better.
Jay has lived lots of places–mostly on both coasts of course–but lives now in Knoxville, Tennessee, where his children are training to compete gymnastics in the Olympic Games. In 2016. Seriously.




