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Penelope Trunk Interview – Author and Founder of Brazen Careerist

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Todays interview is with a very successful female Internet entrepreneur. In this interview you will see not all entrepreneurs think the same, Penelope works very hard and is building up a huge website. A great interview offering some good advise although I do have the feeling she is slightly madder then Dean Hunt, if thats possible!

Could you describe what you do and how you earn your living Penelope?

I’m CEO of Brazen Careerist.

Tell us about your main startup Brazen Careerist and where do you want to go with it?

Main startup? That’s hilarious. It’s like ten full time jobs. I don’t think I could have any not-main startups. I want it to be a community where people can control their online brand and build their lives and their careerst through conversations.

I understand that back in 2007 you sold equity in your blog to start Brazen Careerist, this is something I haven’t heard of before. Why did you decide to do this and looking back do you think it was a good decision?

I sold equity so that I could build something bigger than just my blog by leveraging the brand name Brazen Careerist. I saw that I was able to use the name to build traffic and community for other bloggers and I wanted to do that on a larger scale.

Your career advice has appeared in more than 200 newspapers and magazines including Time magazine, San Francisco Chronicle and Boston Globe what’s your secret to getting lots of press coverage?

It’s not press coverag  per se, but a weekly column that has been running for eight years. It’s nearly impossible to get a column in newspapers, and I don’t recommend that anyone try. I wrote for about four years without pay, and even with a widely published column, it’s not that much income: flipping burgers at McDonald’s would probably be more reliable.

As well as having three startups you also run a very successful blog with over 30,000 subscribers, what would you say was the key to your success?

The key to getting 30,000 subscribers is to write good content and care a lot about community. The key to having three startups is being insane. Venture-backed companies are very high-risk and very stressful and if you can handle working for someone else’s company, you should do that. Your life will be more stable. I have the fortune and misfortune of a nonstop stream of ideas for companies and an insatiable excitement for trying them out to see what happens. It makes for a very exciting but unstable life.

So many people in our industry are two faced and for lack of a better word, scam artists. I recently read a post you did on your blog where you called out an A list Internet entrepreneur which I enjoyed reading. Do you think its important to be honest with your readers and when you see something bad happening, to call people out on it?

Bad stuff happens every day. I think mostly we should concentrate on ourselves and try to be our best selves. I mean, I lie all the time. Last month I lied to someone about my past sexual history so that I wouldn’t have to have a drawn out conversation about it. I bet you have scammed people, too. So for the most part I try to just be honest about myself, and that’s hard enough.

I wrote the post aobut Tim Ferriss because I’m so incredibly sick of how he interacts with me. In general, though, I don’t mind people being scammers — I just stay away.

Please Note: I am a huge believer in Karma and so I haven’t scammed any of you 😉

Typically we see a lot more men become a success with online business, what would you say to the women out their who want to give Internet business a go?

Find true meaning in using SEO tricks to sell guitar lessons to people who don’t need them.


Really, though. Most of the people who make money online are doing things that don’t interest women. So what? Women are making a ton of money as mommy bloggers, and men are not making a lot of money wriiting about parenting. So fine. Men and women make money online doing different stuff. It’s true offline, too: Men aren’t strippers.

Running a Internet Business gives you choices and freedom to do what you want, when you want. What would you say the Internet Lifestyle is for you?

That is total bullshit. If you are really running an Internet business then you are running a startup — I mean, if you are really supporting yourself and a family. And if you are not doing that then you are doing something else that you’re tied to, right? So if you are running a startup, then you are in the most high-risk category of any profession for divorce. Because the life is so stressful.

Working with the end in mind is something I think about every day, where do you see yourself in a few years time? Do you have an exit plan in mind?

Sleep. I would like to sleep more. And I’d like enough money to take a private pilates class twice a day so that I have perfect spine alignment all day and abs that make people reach out and touch.

What would you say is the biggest single reason for your success?

Hard work. I work way more than most people. I’m not sure if this is good or not, but it’s true.

If you could go back in a time machine to the time when you were just getting started, what advice would you give yourself regarding making money online?

I never set out to make money online. I try to figure out what I’m great at and what I can get paid for, and if I happen to need the Intenet to meet my life goals, I use the Internet. Find your true best self before you decide you need to be making money online.

What is the best advice you have ever been given?

Trust yourself.

Check out Penelope’s blog here if you want to learn more about her.


  1. Quality interview man! Keep up the great posts! 🙂

  2. Stuart Wooster says:

    She is not one to beat around the bush, she tells it like it is!
    She is right, hard work is the single reason for anyone’s success! You only get out what you put in!

    I like her no bullshit attitude Hahaha!

  3. Ben vernon says:

    Another Quality interview mate lets keep up the good work

  4. James Cunningham says:

    Another Great Interview Micheal, was very interesting to read.

  5. I love this interview!! Penelope tells it like it is and is totally hilarious in her blunt honesty! As a working woman, blogger and single mom of 4, I can relate to much of what Penelope says on her blog. (goes to show ya that not all your readers are under 21!!) She’s great and has inspired me to be just as authentic…because that’s what really makes people come back.

    Thanks for posting this interview, Michael. You have just made me a lifetime reader of Penelope’s blog! =)

    • Michael says:

      Glad you enjoyed it Coree, she sure gave it to us real. Hard work does mean better results. Heck if I was working as hard as her I would be a millionaire by now.

  6. Barry Dunlop says:

    Love the honesty – love the humor

    Great interview with a very clever lady – well done

  7. Jackie says:

    Thanks or that interview with Penelope. That would be more encouraging and helpful to women though. But I enjoyed the reading and our of this interview I just had good idea on what to blog about. Thank you!!!!

  8. Shane - Inspiring your Success says:

    HAHAHAHA!!!!! Amazing personality, I want to meet that woman!

  9. gabybali says:

    Woww…Penelope is truly a role model and inspiration for me…Thanks for the post! Cheers from Bali,Indonesia!

  10. daniel_m says:

    hmmm… interesting.

    Not quite sure what to make of this?!

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