Big announcement: I’m starting a company!

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Before I tell you about my company, I want to tell you that ever since I started spending eight hours a day on my blog – which was about two months after I started blogging – I have always thought of the blog as a business.

People would marvel that I could spend so much time on something that is making no money, but I always knew that I was building something bigger. I just didn’t know what it was. So while I’ve been blogging this whole time, I’ve been studying business models, and watching other people turn blogs into businesses and media conglomerates, and I’ve been thinking about what I can do with my blog.

In October I will officially launch the site Brazen Careerist, at the URL BUT WAIT! Don’t click there! Because I’m in arbitration with the guy who is squatting on it, and it’s already killing me how much money he’s making from running ads on the domain. Fortunately my lawyer swears to me that the URL is rightfully mine.

Brazen Careerist will be a network of bloggers talking about the intersection of work and life, and it will be a resource for young people who understand that they are in the driver’s seat when it comes to employment. What does being in the driver’s seat mean? It means first that you are responsible for your own career – your personal growth, your personal brand, and your personal fulfillment. But it also means that you understand that you are in the driver’s seat when it comes to employers; companies need to cater to employees if they want to get the good ones.

To get things rolling, the first thing I did was join forces with Employee Evolution. It’s a great community blog for young people talking about work, and their traffic is growing quickly. To create this partnership I had to negotiate with Ryan Healy, who has a guest column on this blog titled Twentysomething.

Background: I met Ryan online when he asked me to check out his blog, Employee Evolution. He had only posted twice, but I loved both posts, and I hated thinking that such great posts about my topic area were not on my blog, so I invited him to guest blog.

He has been doing that for about six months, instigating ire among many commenters. But I love his posts. Well, I love most of them. Some of them I have thought were sort of stupid, but I didn’t say anything, and often those turned out to be really popular. I liked that I could trust him to know what would be a good post.

One of his posts made me want to kill him. It was when he wrote that his Baby Boomer dad was talking with him about how companies need to teach Baby Boomers how to “pass the torch to Generation Y”. LIKE THERE ARE NO GEN-XERS IN CORPORATE AMERICA???!??!

But it is actually true that the Baby Boomers and Millennials think Gen-X does not exist. So I liked that Ryan is able to capture that situation; now I have somewhere to link to when I want to bitch about it.

I quickly realized that his posts were very popular and his blog was growing very quickly. I thought of paying him per post, but I didn’t think that would actually matter to him. I mean, Ryan had a good job at a brand-name company and his boss loved him. I remembered when I had a big job and I wrote weekly columns for Business 2.0 magazine; the money was so un-motivating to me that I often forgot to send an invoice. I thought about what did motivate me — personal growth, the excitement of learning about what I can do, and learning how publishing works.

I knew I had to do this for Ryan. And this is the ultimate question for corporate America. Right? How to retain Generation Y when their primary motivator is not money.

I focused on being a really good mentor to him and helping him open doors. But I couldn’t figure out what doors to help him open until I knew what he wanted. So I tried stuff. Like I told him I could help him get a book deal, and he said, “I don’t really see what doing a book will get me.” He had a point. I’m the first person to say don’t do a book unless you have a plan for leveraging it to do something else in your career.

After a while, I realized that he wanted to start a company. This was great news to me because I wanted to start a company too, but I needed to find the right people to do it with.

A lot of people come to me with company ideas – some want me to join them, some want to buy Brazen Careerist – lots of ideas, none of them right for me. After all, I’ve got two young kids. So I can’t relocate to New York City (yes, someone offered, just ten months after I left New York City) and I can’t keep crazy startup hours because I want to be with my kids.

Ryan and his partner, Ryan Paugh, seemed great for me. There is a reason that Silicon Valley is full of startups run by twentysomething guys. Sure, there is the technology issue – that more guys take computer science courses so more guys start technology companies. But it’s more than that. Guys in their twenties don’t have kids — they don’t even hear the tick of a biological clock – and they have the ability to focus almost solely on work. In fact, Ryan told me that he had a fling with a 26-year-old, but it made him uncomfortable because “every woman over 25 is just looking to get married.”

So Ryan and Ryan are moving to Madison to do the company, which should be very fun. But if you think generation Y’s sense of entitlement is bad at your office when you are trying to get work out of them, you should see what their sense of entitlement looks like when you’re negotiating equity.

Ryan Healy and I negotiated for two months. During that time he was in Business Week one week, the New York Times the next week. Once he put me on hold to take a call form 60 Minutes. It was crazy. He is twenty-three and had only been blogging six months, working less than a year, and he was quoted everywhere as an expert.

The final crushing blow was when the Wall Street Journal interviewed both of us about tips for young grads, and then quoted us both saying basically the same thing: Get a mentor. Hilarious, right? Since I started out as his mentor? But, like any good mentee, he started catching up to me very quickly.

So by the time I was negotiating equity with Ryan, he was asking for 50% of the company.

Every night we went back and forth about equity, and what things will look like, and what he will do, and we sort of had a sort of agreement.

And then he went back on stuff I thought we agreed on, and also stuff I thought was moronic to even question me on. So I said, “You know what? Go get some advice from an adult. Go ask someone with some experience, because this is totally ridiculous and I’m right. ”

I was so pissed off that I had to pull the car over to the side of the road in order to properly leverage my angry voice.

He said, “I can go ask someone now, but eventually you have to let me make my own decisions. We can’t work with each other if you don’t trust me to make my own decisions.”

It was a turning point. Because he was, in that moment, so much wiser than I was. I knew I was right about the business issue, but he was right about the interpersonal issue.

I have told very few people about the company because I wanted to know it was really going ahead before there was online chatter. The few friends I did tell are people who don’t read blogs. They would ask four or five times, “How old is he?!?” They were incredulous.

I tried to explain that my audience is young people so I need to go into business with young people.

I do not choose my friends for their knowledge of generational issues at work. So my discussion of the importance of working with people in other generations fell on deaf ears. Eventually each friend, trying to make sense of things, asked if Ryan and I are hooking up.

When I was in my twenties, I started a company with a guy who was much older than I was. Men asked him all the time if we were a couple. And, at the time, I thought it was an incredibly ridiculous assumption. But now that I’m the one who is older, and people are still asking the question, I am comforted by what appears to be nice gender equality when it comes to trashy assumptions about startups.

So now there’s a new company, and I’ll be blogging about it here. I’m not sure what it’ll be like, but I have an idea of what’s to come:

When I signed up for Facebook, and Recruiting Animal created my Facebook page, Ryan was the one who noticed that I had no idea how to actually use Facebook, so he gave me a tutorial.

He used his page as an example, and then, after I made sure that you can’t tell how many times someone looks at your Facebook page, I spent three nights checking out all 300 photos he had of himself and his friends. Finally, after I couldn’t take it anymore, I sent him an email about how he needs to take down some photos. I know: This after I published a post about how the photos don’t matter.

He said the photos are fine.

I said, “What about the one of you straddling that girl’s face?”

Ryan: That’s not me. It’s my friend.

Penelope: Well other people might think it’s you.

Ryan: They won’t. And no one cares.

Penelope: I cared.

Ryan: It’s because you’re so old. It’s not that big a deal. They have clothes on.

I told him he should take down the photo.

I don’t know if he did. And that’s the beauty of our relationship: I tell him my Gen -X perspective, he tells me his Gen-Y perspective, and then we each see what we can get away with.

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  1. Sam Davidson
    Sam Davidson says:

    Congrats for you all. I think the blend of an X and a Y will be great for this kind of venture. After all, most of the time, great partnerships are what make great businesses.

  2. Rahul
    Rahul says:

    Awesome post. Even though you didn’t really say much, just reading your rants is entertaining (sometimes — other times it’s boring). Good luck with the whole thing.

  3. Rob
    Rob says:

    Congrats on the company.

    Not sure if the “taking photos down” is an X / Y thing… I mean, I’m pretty firmly in X, and the very idea of “inappropriate” photos make me laugh.

    Kudos, again.

  4. Anne Zelenka
    Anne Zelenka says:

    Congratulations! What exciting news! Can’t wait to see what you guys come up with.

    But why would Ryan and Ryan need to relocate? What about web workerhood and virtual teams? ;)

    Of course when you’re in your twenties, why not relocate. And I’m sure Madison is a terrific place to live.

    That’s so true that baby boomers and millennials act like we gen Xers don’t exist. What’s up with that? Please keep bitching about it. And everything else. I’m looking forward to lots more brazenness.

  5. melanie gao
    melanie gao says:

    I just checked out and found myself helplessly following a link for some gorgeous Carlos Santana shoes, which I almost bought but came to my senses at the last minute, realizing I shouldn’t give my e-business to the guy who’s squatting on your URL.

    OK, back to the topic. Congrats on the new business! I’ve never been too fond of Ryan’s content so I’m skeptical but will reserve judgment until I see your new site. I wish you both all the best!

  6. Joseph Beckman
    Joseph Beckman says:

    Looks like was registered in Jan ’06. If you don’t have a registered trademark, I hope you had developed TM rights by that point because I suspect the question will be whether you had TM rights as of the time he first registered and not at this later time. A lot of my clients will register domain names before even considering a trademark. IIRC, you don’t have the option of an ICANN action without a registered trademark, so off to federal court. Good luck with your case.

  7. Brian Acord
    Brian Acord says:


    Thanks for sharing your story. I love to hear about different startups, especially where they got their ideas and what struggles they had early on. I teach entrepreneurship and have started several companies of my own and am currently blogging about entrepreneurship on several sites. I’d love to hear your follow up stories that are focused on entrepreneurship if you’d ever care to drop by.

  8. Alex K
    Alex K says:


    Congrats on starting a business, and good luck!

    I am also starting a company with a partner. I’m in my 20’s, and he is in his early 40’s. Fortunately for me, he treats me with utmost respect and does not automatically assume that he knows better just because he’s older (even though most of the time he knows better indeed;-) )

  9. Dean
    Dean says:

    If you really wanted to get perspective on the intergenerational thing and how it affects the “youth” of the work force, you really need to get a “Boomer” perspective. How otherwise will you be able to offer a balanced perspective and work out some of the challenges that everyone in this stew called life faces?

  10. Graceless
    Graceless says:

    Oh this is a fabulous post!

    Congrats on the new venture!! I can’t wait to see things up and running and in full swing.

    And I just want to say thanks for having this blog and thanks for coming to BarCamp Nashville. Hearing you speak there, and reading you here has been incredibly motivating. The past year and a half has been a long uphill journey trying to find my Professional Self and my place in the business world, and your insights have really been an incredible help and source of strength.

    Okay, enough of the sappy-ass fan-mail stuff. Is that Ryan boy cute????

  11. Heath
    Heath says:

    Congrats on the startup,

    Glad to here your staying in Madison. I love this place. I started reading you blog back when you said you moved here from NY. My favorite blog of yours is from yahoo finance. “My So-Called Financial Life” I thought you right on with that. I normally don’t read blog’s but I sent that one to alot of people.

    Good luck with the startup!
    Heath – A computer network geek in Madison

  12. Sheila at Family Travel
    Sheila at Family Travel says:

    You know, anyone who says that you have to keep blog posts short because “no one reads long posts” is full of horse manure. People WILL read long posts when they’re good, and this one is!

    I was the same way when I started blogging — I didn’t know where it was going, and Mom said “But you’re not making any money from it!” yet I knew that it was going somewhere great, and it is.

    You guys will do something groundbreaking and important and buzzy, and I can’t wait to hear about it.

  13. ex-msft
    ex-msft says:

    Fantastic news, congratulations. (Although I have to mention that the only offensive thing I’ve ever read on here is Ryan’s horrific statement that “every woman over 25 is just looking to get married”. Um, Ryan? Some advice. Every woman YOU’VE TRIED TO DATE OVER 25 might be looking to get married, but I assure you with 100% certainty that your statement patently false. There are plenty of women over 25 who are more concerned with success and achievement and either aren’t concerned with finding a partner right now, or don’t feel the need to have the unnecessary appendage of a needy man, who can’t stand when he’s not the center of attention when her career is, holding them back.

    But, that’s just me.

  14. Carol
    Carol says:

    Best of luck to both of you! Looking forward to reading about it.

    And BTW – not all your readers are young… I’m almost 40 and have got a lot of value from your blog.

  15. Chuck
    Chuck says:

    My respect level for Ryan Healy just went way up, and here’s why:

    "I can go ask someone now, but eventually you have to let me make my own decisions. We can't work with each other if you don't trust me to make my own decisions."

    Most important lesson to any young person looking to partner with someone older. Once you enter into business together, you become peers for the most part. The mentor aspect has to fade quickly or there will be no give and take.

  16. David B. Bohl at
    David B. Bohl at says:


    Congrats on forming the new company. The way you described it on your blog, I first had thoughts of envy – €“ and I still do. When I moved beyond that, I forwarded your post to a client of mine to start a discussion about what more we could be doing with each other in business.

    Thank you for getting my juices flowing and for bringing out my creativity.

    I wish you fond regards in this new endeavor.


  17. Rob Salkowitz
    Rob Salkowitz says:

    Congratulations. I love reading both of your blogs – should be an exciting project. Your story reminds me of negotiations I had with a prospective (Boomer) business partner when I was 24. He was all about vision and leadership and was dumbfounded at how goddamned pragmatic and transactional and, well, X-ish I was about everything.

  18. Matt Bingham
    Matt Bingham says:

    Hey Penelope – Great job on the startup. How exciting for all of you. I enjoy both blogs so the combination of both will be a readers delight. Thanks for the post.


  19. Tim
    Tim says:

    “He is twenty-three and had only been blogging six months, working less than a year, and he was quoted everywhere as an expert.”

    He may be quoted as an expert, but seriously, if you read Employee Evolution you know that neither he, nor the other Ryan, have a clue to what’s going on in the world.

    How can you take anyone seriously who says things like: "every woman over 25 is just looking to get married." Maybe he should blog for Maxim.

    Penelope, keep the two Ryans as entertainment, but try to get real experts as well.

  20. Flying Squirrel
    Flying Squirrel says:

    I enjoy reading this blog less and less the more Ryan there is. It seems as though Ryan tries to mimic Penelope’s attitude, but he has no substance or expertise to back it up. I enjoy Penelope’s frankness because she has a great track record to back it up.

    FYI — I’m a 26 year old woman. I am not looking to get married.

    Ryan’s writing would be interesting to me if he was only a “case study” on Generation Y — not doling out unwanted advice and making sweeping generalizations.

  21. viasenzanome
    viasenzanome says:

    Congrats for the new company!

    It’s my first comment on your great blog and as an italian twentysomething, I wish to thank you for so many invaluable insights in the corporate world.

    Good luck!

  22. Dale
    Dale says:


    If you guys really do get this all sorted out, you will eventually rule the world.

    Be careful though. Everything comes at a cost.

    Always the wet rag of reason.

  23. Ryan Geist
    Ryan Geist says:


    Congratulations! You are brilliant and clearly a WONDERFUL MENTOR!! I think I talked with you for 20 minutes, and you opened up a whole new world to me. The EE Ryans are fortunate to have you in their court.

    I’m so excited for your business, and I look forward to chatting with all of you sooner rather than later.

    Now, do me two favors:

    1. GET TRASHED TONIGHT!! (It’s a celebration, bitches!)
    2. Take inappropriate photos and post them on Facebook

  24. Recruiting Animal
    Recruiting Animal says:

    Good luck P. I assume that the 50-50 split is between you and EE as a whole(which consists of two people). It wasn’t clear if it is purely financial or if it defines the decision-making power as well. I look forward to transcripts of your coffee shop (or kitchen table) conversations. (And thanks for the nod).

  25. klein
    klein says:

    The photos don’t matter until the wrong person looks at them a year from now, 10 years from now and he doesn’t get the job he wanted because of them. Or when he’s trying to be taken seriously in a certain arena where this will bring down his credibility.

  26. Stephanie
    Stephanie says:

    You do what not many bloggers can – captivate the reader. I keep reading line after line. Even when your posts are very long and even when there are no corresponding photos. You’re just that good of a writer.

    I look forward to hearing more about the new business venture…

  27. Jan D
    Jan D says:

    I hope the two of you figure out what you want to do together. I agree that he should take some of the uncomfortable pictures down. As a person who does employment hiring, I would wonder about hiring a person with such bad judgment.

    I do not think Ryan has lived long enough to be an expert in anything. He has a dreamy way of viewing the world. Anyone who thinks living in abject poverty would be character building needs to live a while longer.

    Reading both of you gives me some insight into the X and Y generations I have to deal with at work. I wish you well with the new company, I hope you can both dedicate yourselves to working together.

  28. Penelope Trunk
    Penelope Trunk says:

    Thank you so much for the comments! I really appreciate all the good wishes. I’m so excited, and it’s so nice to have a community to share the news with.


  29. d
    d says:

    The value that Penelope brings to the table is that–although her own track record is kind of marginal–she’s got some extremely worthwhile life experiences. So you can at least argue that she’s worth listening to with an open mind.

    By contrast, I can’t imagine what on G-d’s green earth Ryan has to offer. Perhaps there’s this latent market I’m unaware of, where people clamor for career advice from a spoiled, rich kid who “wishes” he could scrounge to make rent, and whose career advice amounts to “live with your parents and use their business contacts.”

    On a separate note, another Ryan writes:

    “it’s a celebration, bitches”

    Is there a Ryan who has anything adult or insightful to say? Anywhere? Is this just something that comes with the name?

  30. Shefaly
    Shefaly says:

    Good luck, Penelope.

    What a full spectrum of emotions are expressed in these comments here! From envy to genuine best wishes, to downright nay-saying.

    It makes a great case study in how entrepreneurship is seen, how generations see each other, how biases and prejudices know no specific parameters.

    And in how on the web, people with positive comments are happy to leave their identifying information behind, while those making negative comments sign off with pseudonyms, without any links or even their full names.

  31. Ken
    Ken says:

    Good luck to you and R&R. Being a fiftysomething boomer I love your zestful spirit and contagious energy. Being a bruised downsized boomer I appreciate your independent entrepreneurial direction with loyalty to yourself and not a corporation.
    As far as the generational quibbling I think each group has the opportunity to lift the next one higher. My family took this route: Coal miner -> Factory Worker -> Engineer -> ????.

  32. Cam
    Cam says:

    Offering my best wishes, too, Penelope, but like others have noted, I honestly don’t find Ryan’s posts insightful (and I’m in my 20s myself), nor are they well-written, and I’m surprised by your decision. I’d be prone to spend a lot less time on this blog if there was more of him (I’ve already cut back because of his frequent posts, and a few of my colleagues have mentioned to me that they have, too, for the same reason). I’d love to see you pair up with someone who’s at least 25 with a solid work track record (there are SO many insightful trailblazing 20-somethings who have much more to offer!) and more respect for women, frankly. On the other hand, love reading what AJ Jacobs has to say-good choice on that one.

  33. Joselle
    Joselle says:

    That’s exciting news, Penelope. Congratulation. I’m eager to see what the new site will be like. But, I do have to say, as a 20-something myself, I’m less than thrilled with most of Ryan’s post. In fact, they are my least favorite part of the blog. His comment about wishing he could scrounge for rent just smacked of so much entitlement and cluelessness about people for whom scrounging is not a cool rite of passage but a way of life. I suppose I was that short-sighted at 23 too and I find Ryan’s excitement and ambition really encouraging. But I would have love to see what a collaboration or guest column from someone like Carmen Van Kerckhove (who I first of through your blog) of Racialicious ( and Race in the Workplace ( would have bring about. I’m guessing that you plan on having a greater variety of voices–from women, from people of color, from people of the various generations we all work with now–with this new venture and, if so, I do look forward to that.

    Best of luck!

  34. Joselle
    Joselle says:

    I normally don’t double comment but the typos were too numerous to leave so here’s a bit of a clean up:

    But I would love to see what a collaboration or guest column from someone like Carmen Van Kerckhove (who I first heard of through your blog) of Racialicious ( and Race in the Workplace ( would bring about. I'm guessing that you plan on having a greater variety of voices – €“from women, from people of color, from people of the various generations we all work with now – €“with this new venture and, if so, I do look forward to that.

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