Underreported hazards in early-stage startups


It’s Tuesday, which is usually the day for the Twentysomething column. But Ryan announced last week that he’s quitting as a columnist. I’m not surprised. He’s gone through a huge transition – quit his job in Washington, DC, started a company (with me), and moved to Madison, WI – two blocks from me.

It’s a small town, so it’s not like he was ever going to move ten miles from me – I mean, ten miles from me in almost any direction is a corn field. But it’s funny to me to have him so close.

I ended up going over to his house a lot in the first few days, to check in on him and Ryan P without saying so. Almost immediately my kids saw the situation as new neighbors. They refer to “The Ryans” and when we went apple picking, the kids thought of the Ryans immediately.

So we brought over a bag of apples. The kids did not really understand the concept of red all over, so the apples were not ripe. And I couldn’t tell if the Ryans noticed, but they were very grateful, because it was when the Ryans first got here. When they were grateful in general.

Now it’s been six weeks. And Ryan is thinking that maybe his new blog will be about how crazy life is working with me.

I asked for examples. He gave the one about how I invited the Ryans over for dinner. I picked a night when my husband wasn’t home because there is too much tension between us to put the Ryans through it as well. I also picked the night my kids wanted an impromptu Halloween party.

So there was our nanny, who is actually a guy who is a college sophomore taking a year off to establish residency so his University of Wisconsin tuition goes down. And there were fake eyeballs and pumpkin glitter. And it was like a frat party with toddlers instead of girls. To me, that is the weird part. To Ryan, it’s weird that I didn’t cook.

“You ordered burritos!” he says.

I tell him it was better than Batman spaghetti O’s.

He shakes his head in disbelief. He thinks I’m eccentric, which I probably am, but I think this is not the best example.

Other mentioned eccentricities: I have been working out of a coffee shop for a year. Ryan can’t believe it.

The women who own the shop are probably my best friends in Madison – I see them every day. In the summer they noticed me showing up in my obsessive long sleeves and long pants so the sun doesn’t get me, and in the winter they saw me fighting with my husband at the curb when he drops me off. I always imagined I’d have some great post about how the owners let me do radio interviews from their land line (radio producers hate cell phones) and they buy Lean Cuisines especially for me so I don’t have to eat their muffins for lunch. It was a great setup.

Til the Ryans came.

They said everyone in the coffee shop is annoyed by my talking on the phone, which is probably true. So we went to their apartment. Like it’s not eccentric for me to be spending my days in the apartment of two twentysomething guys.

But as we were leaving the coffee shop for good, new art was going up on the wall: Phil Porter. I loved the art. Ryan hated it. So I gave a lecture right before we left, about why good art forces you to see things differently and the Ryans only like art with naked women on it because it doesn’t challenge anything that’s already in their mind. (Yes, they have a painting of a naked woman in the apartment. And yes, it sucks.) Ryan called me a snob.

He is a snob, too. For example, Ryan does not wear black shoes with khaki pants. I have never heard of this rule, but I confess to immediately putting my khakis aside until I got brown shoes, just in case he’s right.

Maybe we get along because we’re both snobs. Or maybe our excessive judgementalism, which probably makes for good blog posts, gives us a sort of detente.

I went out to dinner with Ryan P’s parents. I can’t ever recall going out to dinner with a co-worker’s parent. But here’s a tip. You know how when you go out to dinner with a boyfriend and his parents, you end up liking him even more? I am not sure why, but this always happens. And I have to say that the same thing happened in this situation: I liked him better. He has the same odd speech cadence as his dad, the same bright smile as his mom. It was nice to see.

Nice as long as I could squash my jealously; I don’t recall a time when my parents drove across state lines to dote on me.

Now I wake the Ryans in the morning. They are not morning people. I know you expected this post to be about starting a company, and this sort of is, because the first part of starting a company is learning boundaries.

A startup is inherently intense. Founders are so dependent on each other, and there are almost always only two or three people involved. I have two close friends who have startups: The woman’s company is three women and the man’s company is three men. I think that most startups with a both genders involve sex, and/or marriage, and those that don’t require navigation of a difficult and dicey new language of boundaries, (which I have touched on before).

There is a lot written about work spouses. That is, people who feel like they spend so much time together that they’re married. But they are not. The context for these relationships is usually a big company, where there is safety in numbers, and there are office conventions to keep boundaries in place.

A startup usually has none of these safeguards, and a startup usually entails longer hours at the office. Maybe this is why so many startup teams are all men or all women, but not mixed. And maybe this is why my friend, who has a startup team of three guys and will not consider hiring a woman as the fourth, is making a smart decision.

Meanwhile, we continue to draw boundaries at our own startup. For example:

Ryan P comes to the dining room table that is also our office and says, I have a rash.

I start thinking about my kids.

Where is it?

On my leg.

Can I see?


Why not?

It’s too early. Ask in twenty minutes.

Tyeptyeptyep type

Can I see it ?


While Ryan P is typing a blog post about how he would rather work for man than a woman (yes really: he says men bond better with men) I look under the table. I don’t see the rash, but the light is not that good.

What are you doing?

I need to see it.

It’s not on my leg. It’s on my groin.

And this is the moment. The boundary moment. I look away because some boundaries are clear. But I also think of my kids – some boundaries are murky — and I navigate the best way I know how as CEO of a startup:

Does it itch?

42 replies
  1. Queercents
    Queercents says:


    It's fun to read about you starting a business with a couple of Gen Y guys. In my career, I've noticed men tend to build teams for specific functions while women build them for community. Perhaps that's why the women at the coffee shop keep the freezer stocked with Lean Cuisine and Ryan P will not be baring his rash anytime soon.

    • Jessica S
      Jessica S says:

      Are you for real? Posting about your supposed miscarriage? You seem to want to bring people to your blog pretty desperately.
      7:34 am in a board meeting having a miscarriage? Hmm you would not have made it to any meeting let alone walk around having a miscarriage & if you were which I call bull*hit then you have very little respect for yourself & your children. Miscarriage is painful both emotionally & physically & to broadcast it as if you were taking your mornung dump is
      not a professional nor respectful thing to do.
      Taking something serious & making a joke if it is pretty
      immature & any advice you have to offer is F**ked up &
      you simply are a desperate attention seeking selfish person.
      You owe an apology to women who have experienced loss & losing a baby to a miscarriage is not a relief & abortion is not birth control!
      Get a grip & think how lame your twitter is.
      You are like a child – negative attention is better than no attention.
      Why not do something good & focus on gaining respect & attracting
      people who will respect you & your “business”
      Grow up!

      • Janine
        Janine says:

        I really despise comments like this for the following reasons:

        1. At least post it in the relevant section, on a relevant post on a current date.

        2. The comment is completely hysterical in that disturbing Freudian sort of way when psychiatrists talk of hysterical women.

        3. The snobery of thinking that some mediums are appropriate to express this kind of throught and some for that kind of throught.
        Whatever your opinion is you cannot control (nor should you have the right to) who uses what medium to say whatever they have to say.

        4. Last but not least: The overwhelming intolerance of the comment. i.e Everyone must feel the same way I feel. Good people do what I do, bad people disagree.

        This kind of comment implies that if you have any feelings that are non-prescribed about periods, babies, abortions or miscarriages whatever, then they must never be expressed in case they shake the commentors own fragile pre-concieved ideas.

        Its ridiculous.

        ps- Penelope, I’ve gotten trapped in this blog. I ought to be working but I’ve been surfing through the many related posts and internal links for about 2 days and now I’m in a nightmare maze of multiple tabs. I’m having a nice time though. This is a good blog.

  2. Dale
    Dale says:


    This was a great blog! I think that you folks have a unique opportunity to benefit from your interaction, in ways that regular startups cannot. The differences you observed provide meat for your blog; it makes us (your subscribers) more like voyeurs in that we can’t look away for fear of missing something (akin to soap opera addiction); and it also helps you better understand the dynamics of nontraditional career situations in general.
    Go BCT!!
    Brazen Careerist Team:)

  3. Megan
    Megan says:

    I’m sure Ryan’s glad you just shared that he has a rash on his groin with all your readers… ha ha Honestly though, I love your posts. Even if I don’t always agree, they always make me think. I’m working on a startup with a gay man (and I’m a woman), so it’s kind of the best of both worlds. Best of luck to you and the Ryans.

  4. Chris Yeh
    Chris Yeh says:

    It’s okay to wear a black belt with khaki pants. The key is to match the belt color with your shoe color. So black belt is fine, as long as you don’t wear brown shoes.

    Another little tidbit–ideally the socks match the pants, not the shoes.

    Sounds like quite an adventure you and the Ryans are having!

  5. Jonathan
    Jonathan says:

    As long as you keep breaking these social mores and so-called rules I will keep reading. It is inspiring to read about someone who deosn’t let this stuff hold her back. More power to you Penelope!

    Your confidence and ability to get beyond these rules of mixed gender etc are an inspiration.

    As for your friend and his startup team, well “smart” is what works for you.

    All the best.

  6. t h rive
    t h rive says:

    Funny post, P. It gives (kinda like your last post too) a feeling of stress and reality to the startup – though I’m sure you know how to be patient given the experience you have. It’s as if I’m right there with you for the ‘office’ experience.

    I wish you the best with the work! Maybe someday Ryan’ll let you apply ointment to that blogged-about rash. Good luck with that too!

  7. melanie gao
    melanie gao says:

    Wow, you’ve gotta motivate Ryan somehow. Is this blog post going to help or hurt? I don’t know him so I can’t say.

    FWIW I think burritos are a perfectly good dinner if your guest is a good friend, and brown shoes are better than black for khakis. But that’s just me…

    * * **

    Thanks for the comment, Melanie. I love a girl who can comment on managment and fashion in the same breadth.


  8. Karen
    Karen says:

    Great post. Looking forward to reading more and checking out the Ryans!

    BTW–I’m also in Madison, but am getting into business with someone in San Francisco which will probably lead to a move West.

    I’m taking notes from you on male/female partnerships (he’s male, I’m not). You’ve already hit a few things on the head, at least in this partnership.

    Keep on posting!

  9. Caitlin
    Caitlin says:

    I’m with Ryan – the fact that you had small children doing Halloween activities throughout dinner is fine (it’s keeping it real), but the fact that you ordered burritos instead of cooking is a little odd. Burritos are not exactly difficult to make either. But hey, not everyone’s a cook, and it’s not the end of the world.

    Remind me never to tell you something personal like that I have a rash on my groin. It was a funny blog post but he would have to be amazingly well adjusted and impossible to embarrass for that to simply slide off his back.

  10. sarahd
    sarahd says:

    oh come on guys!! Ryan announced he had a RASH… on his GROIN… to PENELOPE TRUNK!!! Anything those guys say or do are fodder for posts, and they know it :)

    And anyway, who announces that kind of thing to their boss?! There’s the boundary issue, if you ask me!

    LOVED the post Penelope, insights into tensions like these give us great perspective on your working relationship with these guys and makes me want to check back for more. I agree with Dale’s soap opera theory!


  11. Scott
    Scott says:

    Very well written post. I really liked the narrative!

    I do feel sorry for ‘The Ryans’ though. It’s like they inadvertently got themselves into the reality show version of a start-up.

  12. Stephanie
    Stephanie says:

    Are you going to put out a “call” for a new Twentysomething columnist?

    * * * * * *

    That’s a good idea. It’s actually a very hard column to write, although it might not look hard. But if anyone would like to take a shot at it, send a topic suggestion my way. Requirements: You must take have a solid opinion on a controversial topic.


  13. Vincent
    Vincent says:

    I’m having a tense week after a tense week last week. This post made me laugh. “The Ryans” should be a sitcom. Or maybe a show on the CW. Do “The Ryans” look good in tight clothing? :-)

    Good Luck with feeling (literally not figuratively) out each others’ boundaries. :-)

  14. Karen
    Karen says:

    Penelope has talked about the ‘love connections’ made through partnering with someone on a start up, why do you think that is? Because when you’ve partnered with someone, there has to be a deep level of honesty, right? When you get honest with someone, your level of intimacy deepens with them, right?

    Makes perfect sense when you break it down. However, a decision has to be made before you get to that point about what to do next. What’s more important…the company or the relationship?

    I have a theory about all of this, as I’m going through it now with my partner, but my lips are sealed, at least to the public. Penelope, I might be interested in sharing with you and getting your feedback. =)

    * * * * * * *

    I think this is a thoughtful comment, which is why I”m responding to it. But I’m going to give a pissy answer.

    Here’s another way to look at it. The vast, vast majority of people who found startups are men. What does it mean if every time a woman joins this group she has to ask herself “what’s more importnat the company or the relationship?”

    I often ask people why they think so few women do startups. People say it has to do with who has computer science degrees. But maybe it also has to do with that when a man does a startup its him having a blast with friends and when a woman does one someone writes that you have to choose between a marriage and a startup.


  15. Dale
    Dale says:


    Double standards and urban myths abound in life.
    In the same way that women are implicitly considered as having to adhere to different rules of engagement in business relationships, asians are implicitly considered to be inherently technically oriented; black men are implicitly considered to be good athletes but poor swimmers; and black women are implicitly considered to be good HR reps.
    The battle to overcome stereotypes is historically documented and ongoing and I see not ceasation in the hostilities any time soon:(

    Fight the good fight.

  16. Jennifer
    Jennifer says:

    I think you may have misinterpreted Karen’s comment (or I did). I think she was talking about choosing between the company or the relationship with the start-up partner, not the company and a seperate marital relationship.

  17. Phil
    Phil says:

    At first I thought the Ryan(s) were a gay couple. I was hoping they were, because that would at least give you somewhat of an excuse, no matter if it is a bad one, for wanting to see the groin rash (regardless of your motherly inquisitiveness). It is very clear though, that you obviously have a crush on the main Ryan and that this new “business relationship” excites you.

    You definitely do not refrain from mentioning your crumbling marriage on your blogs, and this post of your new “partners” makes it very clear that your marriage is not the number one priority in your life. The fact that you won’t even invite your husband to dinner with them speaks volumes on how your value your “business” over your relationship…and you wonder why the marriage has failed? You put yourself above everything and everyone. Your world rules and everything else is secondary. I am sure your husband feels great about himself, especially after reading your blogs, which I honestly hope he does not. If you truly valued your husband and marriage, you never once would have mentioned marital problems.

    This is not a personal blog that you rant thoughts on, this is a professional page that is linked by all of your articles. You have no boundaries between your personal and work life. Your many name changes should have been the first clue to yourself that you have deeper rooted problems that need to be addressed (i.e. you are very self centered and only see your point of view). I truly do feel bad for your husband because from everything on here I have read, you have made it clear that you are the bread winner and the one with the real career. Also, your self promotion is more vital to you instead of actually taking care of the marriage. Everything for you seems to be about a quick “rational” fix. You really need to step back and look at things if you do really value your family over your career, whatever that may be.

    You definitely are going down a rocky road with your new partner because it is all too clear that you have an interest. Whether it is just a simple crush or something more deep rooted, you are the one skewing the boundaries. You got them to move to your town and then you write a blog entry about how you essentially have been flirting with them since they moved here. I suggest you get it over with and divorce your husband so he doesn’t have to endure the coming infidelity and further humiliation of having your dirty laundry aired and linked to all throughout the internet. I am sure your sheep will be apalled by this post, but since you are so free with detailing your love in all aspects, I find no reason not to hold back on my comments. Good luck to your husband.

  18. Karen
    Karen says:

    Wow! I’m a new reader and all, but I think this may be a bit out of hand.

    Phil, how is it ‘obviously clear’ that there’s a crush? Yes, Penelope has blogged about her personal life, but I doubt any of us know 100% what she or her husband is thinking, feeling or has discussed about what’s going on, so who are we to pass judgement? What if he doesn’t support her in what she’s doing? Is marriage not a two-way street or is it just that the woman has to support what the man is doing?

    I’m sure Penelope knows that by posting about such personal things she’s almost guaranteed to have negative feedback, but do you not think what was just said is a bit harsh?

    Let’s talk about ‘the Ryans’ for a second. I’m sure they are brainless, twentysomething guys who can’t think for themselves and had to rely on Penelope to trick them into moving to WI. Seriously??!! Come on! I’m in the same situation as I’m planning a move, but I made the decision. Yes, I’m moving so it will be easier to work with my partner, but I’m the one who’s decided to move. I wasn’t lured by my partner. And if things don’t work out with the business, I’ll have learned from the experience and expect nothing from my business partner. Sorry, Penelope, but I doubt you have that much power over the Ryans to MAKE THEM move to WI.

    All in all…great to hear everyone’s opinions…and that’s just what they are!

  19. Pam W.
    Pam W. says:

    Karen, you need to do some reading on PT. With her marital situation and her ego combined, she will jump at the first male that shows her any attention especially one that strokes her ego!

  20. Jen S.
    Jen S. says:

    I thought this was hilariously funny and so close to what I would do in the same situation that I found myself laughing out loud. I identified so closely with YOU!!. Thank you! Thank you! Thank you! BTW, I think the black shoes dress up the khakis a bit and since khakis are a more casual Friday kind of thing, I would stick to brown shoes and matching belt.

  21. Anirban
    Anirban says:

    This blog crosses over from career advice to a well written literary piece. I found it very original. Perhaps you should try your hand at script writing too.

    PS: Penelope, the way you write about your husband reminds me of my sister ten years ago when she was working and her husband was not, the marriage was hanging by a single thread, and she had a lot of latent anger that was visible in her emails. The good news is that they are still together and he’s got his act together.

  22. Dale
    Dale says:

    My, my, the moral minority have spoken! Pam W. assumes that Penny is an unstable nympho with an ego the size of Madison.
    Phil thinks that her comments are too personal, and that she is a romantic vamp with exhibitionist leanings and a sadistic streak where her husband is concerned.
    Anirban, there’s your screen play:)
    Hey, I wish the world were really so entertaining. But, truth be told, their comments and those of the “sheep” speak volumes about the writers rather than the subject. For one thing, what we see of Penny is what we are allowed to see. Her life is undoubtedly different from anything that we are privy to, and as I alluded to in the past, the deviations into its personal aspects tend to hold us riveted to this blog in a sort of soap opera like addiction. All the literary components for good drama are here, and so too is the emotional audience.
    People, lets just focus on the purpose of this blog and learn vicariously from its creator. She is putting herself on the line to create an authentic arena for discourse and learning, and also is like any one of us, human and therefore fallible. Don’t magnify her bad or good points beyond what they are or we fall into the trap of becoming illogical and judgemental. Also, given the fact that we share our experiences with each other for the common good, we are more like a community of friends than anything else, so lets not fall into the common online trap of being unduly harsh, rude or undiplomatic to each other because we cannot see each other.

    Now, having been the voice of reason, I must say the juiciness potential of the gossip factor here has me spellbound!!!!!!!

  23. Jackie
    Jackie says:

    Let’s assume that Penelope’s career is more important to her than her marriage. To my knowledge she hasn’t stated that, but I’ll agree it could be reasonably inferred. With that assumption entered, I say “so what?” I would bet the vast majority of people with hard-earned, high profile careers have that same attitude. If that makes her a despicable person, then she has a lot of company. Her husband is an adult, presumably capable of taking care of himself.

  24. Pam W.
    Pam W. says:

    And where do PT’s children fall in that hierarchy? Work, marriage, children? Work, children, marriage? Unfortunately, the state of the marriage affects the children.

  25. robsalk
    robsalk says:

    Serious TMI going on here! I’m curious about what this business is actually going to do. With such colorful personalities and dynamics, I’m sure it will be interesting.

  26. Sifi M
    Sifi M says:

    Wow. This is as good as reality TV. I think I will stick to the khakis. Not only are black shoes OK, they are better than brown! You wear the khakis with the black shoes and a black belt and a nice white shirt. Wear your BEST black loafers and they will “pop” as they say on the design shows. This is a timeless look in LA but may not go over in Madison, except on a muggy yet bright summer day. Try it!

  27. mark
    mark says:

    It must be really gratifying to see that the only time you get a significant amount of blog response anymore is when you play the flirty, sexual-on-the-edge card. Keep it up – just a matter of time of time before even that loses its edge. Your are in your 40s, aren’t you?

  28. Jamie R Lentzner
    Jamie R Lentzner says:

    Oh my god – too funny. When I started my company it was only my husband and me, which was okay but not great. Then he continued with his full-time job and I hired women, one after another – at one point there were 8 of including me – not good with that many women – oh ya in my studio/used to be a garage. Now I am going to have to go back and read every single post – great blog!

  29. Mark W.
    Mark W. says:

    I remember this very funny post (e.g. – … better than Batman spaghetti O’s.) I’ll update this post for posterity with today’s tweet.

    Me: “Ryan Healy has hydrocortisone on his desk.” Ryan Paugh: “You should write about his rash like you did mine.” http://tinyurl.com/ypk5sq

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