Penelope Trunk: How to Transform Your Life Experiences Into Profitable Businesses

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Penelope Trunk: How to Transform Your Life Experiences Into Profitable Businesses

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Penelope Trunk

Penelope Trunk is a career advice expert and entrepreneur who embodies the start-up story of the Internets' early adopters. She offers her advice on her website and has also been featured in the Boston Globe, Fortune Magazine,, Business 2.0 Magazine and Yahoo Finance. Her tell it like it is approach and tonality is easily digestible and incredibly intriguing.

As an entrepreneur Penelope has launched four start-ups, each of which have been developed by focusing first on building a community.

Penelope's approach to work and life and the intersection of the two is truly inspirational. In her interview with us, she provides some true golden nuggets of wisdom. As you read through her responses to our questions, be sure to read and re-read them over and over again to truly grasp the context of what she's saying. Her thoughts are truly legendary, giving the reader simple, succinct no-nonsense advice.

Q: What inspired you to become an entrepreneur and what is it about Career Advice that you're so passionate about?

A: I wanted to be a sex writer, and went to graduate school after filling my application with stories about sex. But I was running out of money and wrote a book proposal for career advice, and I got six-figures for the book. So then I was a career writer.

Q: Your businesses all seem to have been developed based on a particular experience you were going through in your life at the time. Would you agree? If so, how do you decide if a life experience will be a lucrative business idea?

A: I think of new business ideas every day. Most of them are not fundable. I come up with a fundable idea about once every three years. For the most part, we only know about our own lives - not other peoples' lives - so successful startup ideas begin with your own life.

Q: I read that you've built every business of yours first with a focus on building a community. Could you elaborate on what you mean by that?

A: I am good at gathering people together and then leveraging the fact that they are all doing the same thing, together.

Q: As a writer and blogger you've developed a loyal following. Some people say that blogging is dead. Do you agree or disagree, and what challenges and advantages do you think bloggers, content creators and community builders have today vs. when you began?

A: It probably takes way too much time and money to launch a blog today that will become big. Bloggers today work full time. And they have to be very smart about product development and marketing in order to make money from their community.

Q: Are there moments as an entrepreneur when you want to quit? If so, how do you persevere?

A: Inability to do anything else. No one should be an entrepreneur. It's unstable, leads to divorce, anxiety, financial ruin. People who do it long-term are a little bit crazy.

Q: What do you think has been the biggest contributing factor to your success?

A: My kids will starve if I don't earn money. If I married a bazillionaire I think I'd just go to Pilates classes all day.

Q: Any advice for entrepreneurs or dream chasers looking to pursue their passion and earn a living doing it?

A: You don't need to get paid to do what you love. We all love sex and eating and we don't get paid for it. Find something you can get paid for. Do what you love for free, just like everyone else.

Q: What do you consider your greatest accomplishment thus far and why?

A: Having the patience to do written interviews. I should be writing for my own blog and I hate written interviews but I am trying hard to be a likable person, and a generous person, so I'm doing it.

Q: Tell us about your latest start-up Quistic

A: Online classes. My favorite one is about personality type. It's totally amazing to me that the Fortune 500 companies all use it for hiring and promotions yet most people don't know their type. Knowing your type transforms how you approach your career and your relationships.

Q: Any exciting plans for the future?

A: Bed.


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