A blogger in the niche of finance and career, Penelope Trunk has built a brand based on the unconventional career advice that she gives on her blog and for the consulting work she does for dealing with Generation Y in the workplace. Her company, Brazen Careerist, appears to be successfully completing a third round of funding, and while she is still the public face of the company and has a lot to do with driving traffic to the website, it's not clear how much she is involved with the day-to-day operations of the business.
Penelope Trunk is one of my favorite bloggers because she is just batshit crazy and a great storyteller. She has described her process as being figuring out what she wants to write about and then figuring out a way to make it fit into her genre of career advice. That includes something as disparate as an abortion or a miscarriage, which she managed to find a way to tweet about and convince people it was a topic relevant to her job. She is very controversial and gets a lot of flack for what she writes, and she often claims that her trouble with people stems from her Asperger Syndrome. Her critics claim it stems from the fact that she is a compulsive liar.