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.

75 replies
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  1. elysa
    elysa says:

    I read about the new business via Ryan & Ryan earlier but yours had much more detail. This sounds like a great thing, I look forward to seeing your new business develop.

  2. Carol Quovadis
    Carol Quovadis says:

    Hi Penelope,
    Best of luck with the new company- looking forward to hearing more about it. Tend to agree with the other commentators re Ryan though. You can see other’s perspective. Ryan does not yet have this skill, and his posts do not allow for the fact that people might have different views of the world. e.g the post on a regular pay cheque assumes every one has no need for security. For some of my clients this is their biggest requirement at this stage of their lives and no way would I tell them this is boring! Every one must follow their own path. Best of luck

  3. Richard Telofski
    Richard Telofski says:

    From your 9/17/07 post – “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.”

    I often agree with you, Penelope. But this one I can’t go for.

    Yes, employees are largely in charge of their own fates; at least to a larger degree than most workers realize. But your assertion that companies need to “cater” to employees to keep them is unqualified. This claim is only accurate in times of low unemployment. Your perspective, and assertion, is limited due to your experience. You haven’t lived through periods of high unemployment.

    In times of high unemployment (7% to 10%), catering is certainly not needed nor is it managerially prudent. I’ve lived during periods of high and low unemployment and I’ve seen companies react by catering and not catering, and everything in between.

    Supply and demand is what it’s all about; and each side must know when they are in a favorable environment before they demand to be “catered” to.

  4. Jaerid
    Jaerid says:

    Hey all (Penelope, Ryan, and Ryan that is)-

    Congrats! I am happy to see that you have found a way to bring it all together. I am very excited for you all. Best of luck and I look forward to reading all the great thoughts on Brazen Careerist!

  5. Pam Bockman
    Pam Bockman says:

    Are you SURE this is what you want to do??? Penelope you are quite capable of runing our own company!!!! I think its a mistake and its going to be difficult for you to manage. Why make your life more complicated than it already is. Believe in yourself and run your own company. I’ve personally seen way too many “partnerships” end in ugly legal battles and companies ruined. He should be a contracter for you and write for your blog!!!!!!!!!!! Stay in the driver’ve earned it.

  6. Cindy
    Cindy says:

    Shouldn’t you have a business idea before you start a company. I mean you say that you don’t know what you will come up with. A “company” is called a company for a reason, it is a group of people who have a joint venture in a certain area and a plan for that venture. You seem to be saying “I want to work with people who have an interest in ‘something’ and we will work on ‘something'”. Maybe the ‘something’ is the blog which seems to be geared towards ‘things’. Hope your ‘things’ can pay three people full time. Hope that this company brings increased traffic to your blog and that you have the webserver and site master to handle it. Good Luck.

  7. Alfred
    Alfred says:

    i love your blog. I have recently linked to you in my recent post the ten Blogmandments. I am not asking you to link back or anything (it would be nice if you could) i would like your thoghts on my latest post when you have the time. Thank you.

  8. Daniel Schildt
    Daniel Schildt says:

    Interesting story to read because it tells much about problems with starting something new and how different people react to things that aren’t done in ways they are used to. Anyways, all good to company.

  9. Mark W.
    Mark W. says:

    I read the post and all the comments and there’s one red flag that would bother me that I didn’t see anyone else comment upon. It was – “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, …
    I’m on the outside looking in and knowing only what I read here and none of the details. Maybe this is just part of the negociation process or just an attempt on both of your parts to get a better handle on the scope and direction of the new company and then maybe not. I don’t know but this post doesn’t make it sound like there is a real connection between two business partners even though the goal may be the same. You have much more experience and knowledge Penelope in business and life compared to Ryan so it is my advice to you that you never lose sight of that fact. That’s just my honest opinion.

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