Career Guru Penelope Trunk: Founder of Brazen Careerist

Penelope at Work Penelope Trunk of the Brazen Careerist is a startling combination of entrepreneur, career guru and bare-to-the-bone personal blogger. Her writing does not draw a clear line between business and personal issues. For Penelope, it's all just part of the messy business of life. TheNextWomen talked to her about "jet money", bad career advice and why you should want to have sex with your business partner.

Why do you think everyone wants to be an entrepreneur these days?

You can make your own hours. It's impossible, as a woman, to have a family and a good job in corporate America. This is why most small businesses are started by women. I notice a lull in email from 2:30pm to 8pm. That's when people are spending time with their kids.

Women are actually very well constituted to run companies especially before they have children, e.g. they can do multiple projects at the same time. But it is a fact that only 8% of venture backed business are started by women. Venture-based startups are very high-pressure which may be part of the reason that fewer women do it.

Start a small business when you still have a corporate job and a safety net. It gives you room to fail without too much risk.

One of my favourite posts on your blog is on career advice that women should ignore. What advice do you think aspiring entrepreneurs should ignore?

Ignore all the stuff about how hard it is. This is mainly propagated by men who have a particular vision of why they want a company. They want the big exit and "the jet money". Women don't talk about the jet money.

There is also a lot of bullshit talked about what women are doing with the kids when they are running a company. Women who start companies tend to be unconventional. If they were happy to be full-time mothers they would find a man who earned enough to let them stay home full time. My advice is to get all the household help that you need. I have no furniture in my living room because I'd rather pay for a nanny. I have 50 different people who help run my life.

One post on your blog is on women who are not your role models. Are there any that you do admire?


Sheryl Sandberg from Facebook. Nothing is over the top if Sheryl does it. The truth is that most women at top of their field have a house husband. Meg Whitman (former CEO of eBay) is a prime example.

I admire women who have unconventional systems at home to support their work life. The problem is that most of them don't talk about it.

What career mistakes do you wish you had avoided?

I wish I had owned who I was earlier, e.g. I did a great job in my 20s and didn't realise it at the time. Don't reflect the standards that are held up to you or to women in general. It's a cliché but it's hard to be your true self.

One piece of advice you give is on finding a mentor by being annoying. How important is it to have a mentor when setting up a business?


All the research show that mentors are crucial to success. Entrepreneurs need to find people who compensate for their faults. The relationship doesn't have to be structured and your mentor doesn't have to have more power than you. He just needs to be someone from whom you can learn.

One of your negotiation tips is that you should not ask directly for what you want. "If you want to go into business with someone, ask them on a date. And if you want to date someone, go into business with them!" Can you elaborate?


Everyone I go out with wants to do business with me. I talk about it a lot and I'm good at it. In fact there is research which shows that people who work together and are attracted to each other but don't act on it are more in tune. They just make a better team.

My first company was actually founded via a blind date. We were obviously not a match so what was there to talk about except business?

Final question, you say that men are better at negotiation, explain?

Did I say that? I actually don't think that's true. Men have all the money so they are more used to it and to having more power in negotiation. That doesn't mean they have the innate skills to be better at it. I mean if you can persuade someone to marry you, then you can negotiate.

Penelope is the founder of 3 startups -- most recently, Brazen Careerist, a web service to help companies find candidates. Her career advice appears in more than 200 newspapers and magazines including Time magazine, San Francisco Chronicle and Boston Globe. In a review of this blog, Business Week called Penelope's writing "poetic."

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