Find people who compensate for your weakness

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The update on my company is that Ryan Healy and I are not talking to each other. Well, he is talking to me, but I am giving him the silent treatment.

Still, I am confident that things are going well. First, because I am bad at the silent treatment—I have too much to say all the time. Second, there is very good research about what makes a good entrepreneur. And the answer is that there is no single personality, but rather it is the type of person who can see their weaknesses and get a partner to compensate for that.

Ryan and I have done that with each other. And during my short stint of silence, I thought about how in fact, we are doing a lot of things right. Here are six things that entrepreneurs must do in order to have successful partnerships, and I think Ryan and I are doing them:

1. Make time for arguments because they are inevitable. You must consider this part of your job, in order to have constructive conflict.
We fight like we are married. Which says a lot, since I am in the middle of a divorce and he has never had a girlfriend for more than fifteen seconds.

So I call him from my kids’ soccer practice to tell him I am not calling him for a week. And I am the parent at soccer who is on my phone instead of cheering every good kick. This is my way of bringing diversity to Madison: if it were not for me, only men would do this at soccer.

To be annoying, Ryan calls me at 5pm, which is death hour to all parents who have hungry kids who are a half-hour from food, and he says he can’t manage cash flow because any question he has must wait 24 hours if it comes up at 2pm, which is when I stop working.

I want to be like, Duh! If I stopped working at 2pm then I would not have any time to fight with you from the soccer field. But I stay quiet because I am trying to be a more reasonable person to work with.

2. Remind yourself why you picked that person. You probably still need him for that reason.
I remember when Ryan and I were first thinking of going into business together. And we spent two months arguing over equity. There was the day I got so angry that I had to pull the car over to fight with him. And neither of us walked away from negotiations. Someone who really hates fighting would have called off the partnership right there. It was a sign that this is what our partnership would be, and we both signed on the dotted line.

In that fight, Ryan was more mature than I was. I was definitely right on the business issue we were arguing about, but he handled himself better. He was very calm. And that only made me more hysterical. (I hesitate to use the word hysterical, by the way, because I know that it validates Ryan’s propensity to call all women he ever comes into contact with “crazy” but whatever. Now he and his friends can have a four-syllable word they can use for variety.)

So, anyway, that’s how it is now. I envy Ryan’s ability to be even-keeled. I am not an even-keeled person.

3. Give each other feedback on strengths and weaknesses.
I’m also going to tell you the worst thing he said. He has no idea that this even bothered me. So right now is the part in the paragraph where he will jump ahead, amazed that I didn’t tell him something that was offensive. Because believe me, he hears about it every single time he is rude to me.

So, anyway, it was a day when we both got dumped. We had each had about four dates with people from Madison, which is, in itself, a miracle, because we are both fish out of water here, and neither of us really expects to find a long-term relationship.

But miracles happen. And we were both smitten. And then we were both dumped. Ryan is the great analyzer of our social lives because he thinks I am a social mutant and only know how to talk if CNN is interviewing me.

So, he says that he was dumped because she was a college girl and didn’t want the structured dating life that a recent grad wants. Then he tells me that I got dumped because I don’t dress like a girl. “You don’t even try!” he says, with his patented combination of exasperation and incredulity.

I’ve been around Ryan long enough to know what this means. He thinks I look like those moms who throw on designer jeans and a Calvin Klein T-shirt and think they have stepped up their game. And they have, for a going to a preschool play date.

So I wore that and I thought I was dressing up, and Ryan thinks I look like I’m in preschool-play-date mode.

4. Use the other person's expertise to improve yourself.
Really, Ryan gave good information about my wardrobe because there have been many times that I have not dressed quite right for television appearances and people have been largely unimpressed.

Also, I am good at taking criticism (lucky, since Ryan is good at dishing it out). So I implemented his recommendation to be girly in Austin, while everyone was Twittering at SXSW about how Mark Zuckerburg's interview sucked. I was down the street at Nordstrom buying accessories.

(There is no Nordstrom in Madison. I plan all my shopping trips at the intersection of the Nordstrom store finder and my speaking engagement itineraries. And, by the way, the next time I use scientific data to choose where to live I will never move farther than 15 miles from a Nordstrom. Nordstrom customers have good taste and Nordstrom opens stores near their customers. )

5. Be aware of generational differences, and don't assume you're above them.
We know we are a shining example of the generational train wreck in corporate America. And it’s not for nothing that Ryan just wrote a post about how the biggest problem in work life for Gen Y is not the Baby boomers but Gen X.

Sometimes we find ourselves laughing about what a stereotype we are. For example, Ryan always wants to collaborate and I want to be alone and answer emails.

He wants to socialize with everyone at work, and I am all about picking up my kids at school.

I asked him to fax something to a client, and he said, “Fax? Do I look like I’m forty years old? I don’t even know how to use a fax. Can’t they take a PDF?”

Ryan and I have parents who are roughly the same age, yet his parents call all the time because they think the company is so cool, and I don’t even think my parents could tell you the name of my company.

6. Startups are difficult for everyone. So don't get hung up on hierarchy. Or anything else.
I was going to tell Ryan today that his problem is that he doesn’t manage up. I was going to say, “Look at the sidebar on my blog. I write about managing up all the time. How about brown-nosing once in a while?”

But he would not take that criticism well. And anyway, he’d tell me he managed up the only night maybe in my whole life that I was drunk: at TechCocktail in Chicago, which I promised I would blog about, so thank goodness I’m getting it in now.

Ryan took off my nametag in an attempt to gain some anonymity while I was totally drunk and probably inappropriate. For us, that qualifies as managing up, probably. But then again, that was the night he told me I am the most socially eccentric person he has ever met, and I’ll never get a date.

I told him that men like socially eccentric because in bed it’s not about being social, so there’s just eccentric left, and men think that means a likely possibility of anal sex.

Ryan was silent. He was driving. But I don’t think he was silent because he was driving.

I said, “See. I told you I’ll get dates.”

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  1. Yvette
    Yvette says:

    I can not believe she wrote that. I am laughing my head off. Eccentric sex? Yup, that’ll work. I predict she will get dates … eventually. Maybe even a few from that post!

    Of course you have to have some attraction first (i.e. you have to dress like you’re ready for sex). The problem with being a mom and looking for dates is that they are two entirely different mind-sets, and that’s more a problem for Gen Y (who have kids) than Gen X, who is just thinking about having a fun date … with eccentric sex.

    My two cents: go for friendship, flirting, and having fun. Love will follow. Really, it will.

  2. Tracy
    Tracy says:

    Hilarious post…I loved it.

    However, regarding #5, I think some of this stuff is more about where your generation is in its lifecycle than about intrinsic qualities of the generation.

    I’m GenX, and when I was 24 I loved socializing with my coworkers. We had parties, went out for drinks, etc. Now I simply don’t have time for that…I have a 2 year old who needs her dinner by 6, so I shoot out of the office like a bat out of heck come 5 o’clock.

    I haven’t changed all that much (I’d still love to go have drinks with coworkers), but my life has changed a lot.

    * * * * * *

    I think the best way to compare generations is to compare what each did at the same age. (Warning to whiners: Generalizations coming:) For example, Baby Boomers protested so much in their twenties, and Millenniels are generally rule followers. Baby boomer went out for drinks after work even when they had kids, and Gen Xers do not. Gen Yers expect good things to come to them when they graduate college, Gen Xers expected very little from the world at that time in their lives.


  3. Ken
    Ken says:

    Sounds like the stars have lined up for you and Ryan to start dating.

    You have already laid the foundation for future arguments, which normally comes later in the dating process.

    Ever the think-outside-the-box person, you just flipped the relationship around. Fight first, then start dating.


    All that’s left is that you may as well have some of the post-fight fun.

  4. Leonard Klaatu
    Leonard Klaatu says:

    I know people who embrace lots of conflict in their life and perform well only when conflict is ever present. When there is no conflict, they’ll create it. Can’t say I understand it because I’m not wired that way (although I do enjoy lively debates that can remain on subject and not lean toward personal attacks).

    Do you think of yourself as a person who performs best when there’s conflict?

  5. J
    J says:

    Didn’t see the anal sex coming, but then isn’t that usually the case? ;-) Hilarious post though I do have to agree with Tracy- a lot of the ‘generational differences’ you write about I would attribute to life stage as well. Guess we’ll know for sure as Gen Y gets older.

  6. Joselle Palacios
    Joselle Palacios says:

    Oh my god. Excellent comedic timing on this one. The anal sex statement wasn’t nearly as funny as your description of Ryan’s reaction. Classic.

    I was going to judge Ryan for calling all women crazy until I remembered I always said that about all guys when I was his age. Then I realized, I was getting off on crazy and I was crazy too. It’s fun. You’re totally right that there is a certain kind of man who loves the crazyweird girl on fire act.

  7. Chris Yeh
    Chris Yeh says:

    I’ve never understood the common male obsession with anal sex. What’s the appeal?

    P.S. Remind me to send you a copy of my “Beat The Dating Market” ebook.

  8. Dr. Lois Frankel
    Dr. Lois Frankel says:

    Hi, Penelope! I couldn’t agree with you more. When I coach people having conflicts at work I often use the Myers Briggs Type Indicator (MBTI) to help them understand differences. Once you get that someone isn’t actually TRYING to make your life miserable, you can see the value added by complementarity.

  9. Yasmin
    Yasmin says:

    Funny & shocking! Classic Penelope!

    BTW, you have some code showing at the end of #4 & the end of your post.

  10. andy
    andy says:


    It’s interesting how you used the term “managing up” when talking to Ryan. Of course he is going to take exception to that, because it implies you are his boss, rather than equal business partners. Also, how does he feel about you airing all of your private dealings with him in a public forum? It’s not surprising you’re having problems with him. To be frank, while your blog is very entertaining (which is why I read it), you appear to be a difficult person to work with.

  11. Hutchie
    Hutchie says:

    HAAAAAAAAAAAAAA! Omigod! I love you, dude.

    And a question – what about the other Ryan? What’s going on?

  12. Neil C
    Neil C says:


    Conflict can be good as long as ideas flow freely, people do not get offended easy, people come to the table with solutions rather than whining and follow the chain of command. That’s my rule in my office & it seems to work well with the guys but the girls tend to be more sensitive.

    My favorite example of conflict producing great creative work is the Eagles. They were able to write & perform some of the best music of their time but fought like cats & dogs along the way. The key was that the creativity was not stifled, everyone involved was extremely talented & issues were settled. The band broke up when the egos got too big.

  13. Michael Henreckson
    Michael Henreckson says:

    Umm, that was interesting. Personally I tend to try and avoid conflict. Not that doing everything the same way is necessarily the only option, it just doesn’t help to get openly hostile any more than you have to.

  14. Robert W.
    Robert W. says:

    I don’t know if your decision to post this was a post-April Fools joke, Penelope, but talking publicly about a man’s dating prowess (or lack thereof) is pretty much akin to the Seinfeld “shrinkage” episode.

    Some things are unforgivable and you may have just permanently severed your working relationship with Monsieur Ryan.

  15. Mark W.
    Mark W. says:

    I think you’ve been to Ireland more than once and kissed the Blarney Stone multiple times.
    I agree with Ryan’s assessment of the Fax technology. I would rather use voicemail. I would NOT use scientific data to choose where to live. I believe the best research can be had the old fashioned way by going to an area and experiencing the people and community firsthand.

  16. Matt Bingham
    Matt Bingham says:

    You know, the best stories about Microsoft starting are stories of Bill and Paul yelling at each other for hours until one finally gave, not because the other was right but because after 10 hours of yelling you just run out of steam. They seemed to have handled it well and I think this is just a dynamic of a partnership when you both are passionate about the success of the company.

    * * * * * *

    Oh I like hearing that Bill and Paul spent lots of time yelling at each other. I will look for some stuff written about this… I actually think it’s just what happens when smart, passionate people are running a business together. They just want to get things right.


  17. Andrea
    Andrea says:

    I predict you and Ryan will eventually (if you don’t already) want to date. Whether or not you will is up to you both, but judging as to how you both seem to enjoy flying in the face of convention, I would say there’s a good chance that you’ll at least have sex. (However, that would probably be suicide for your working relationship, as you know, unless you ended up staying “together.”) Either way, the sexual tension that comes through this post is obvious to me, and quite enjoyable. Am I imagining the flirtation? I would love to know.

  18. GenerationXpert
    GenerationXpert says:


    I think you are correct that our Millennials can’t take criticism that well. However, was it really fair to bring up anal sex? I’m kind of thinking that’s bringing out the big guns. Of course, I’d probably say it too. I also like to win.


  19. Jeremiah
    Jeremiah says:

    You know this was a great post. I remember reading alot of helpful stuff. Unfortuanately all i can remember is anal sex LOL!!!! Wow, i just don’t know what to say.

    Keep up the good work!!!

  20. lucilla
    lucilla says:

    Relationships with people are about complimenting each others strengths and weakness. When I start arguing with my business partner, he reminds me that we are on the same team. It is reciprocal constructive criticism. I loved this article. Thanks for sharing your views on things that make us say, “Hum.”

  21. 40  - €“ - €“ Now What?
    40 - €“ - €“ Now What? says:

    Your post had me rolling in the aisles. I love the comedy, I love that you’re so honest about what’s going on, but best of all, I love the way you hit the generational thing dead on the head. Gen Xer here, I know how to fax!!!

  22. Marsha
    Marsha says:

    OK, I just had a laugh that cleaned out my lungs all the way down to my waist – that felt great. It’s a breath of fresh air the way you just blurt it all out – love it and just keep going. You rock, Penelope!

  23. Dale
    Dale says:

    I hate fighting.
    How do you not bear a grudge after all is said and done?

    This type of interaction is very interesting to me. At my current level of emotional development, I could never work with someone that I always fought with.

    I guess the keys must be either the personalities involved, or the presence of other extenuating or mitigating environmental factors. The question is how will I know that the fighting isn't the result of bad partnership dynamics as opposed to a healthy difference of opinion? Also, how do I mediate fighting with a partner for the best possible outcome? I'm sort of confused here. How do you and the Ryans do it?

    Finally, this is a very valuable post, but Penny, I think it's gravity for the entrepreneurial careerist is lessened by the funny sexual content. I hope you're ready for the backlash.

    Ramblings of an old prude:)

  24. Hutchie
    Hutchie says:

    That’s what I asked! No answer! Hmmmm…

    Okay, okay. I thought the first comment was rhetorical. Sorry about that. Here’s the answer to the mystery of Ryan Paugh: He can’t stand being around me and Ryan Healy when we are arguing. So RP is never around when RH and I are arguing.


  25. eric m.
    eric m. says:

    holy crap, did you just say “anal sex” in your post. hmmm. as a gay man, I’m nonplussed, but still surprised to see it here…

  26. bilbo
    bilbo says:

    I guess since I’m an INTJ we’re not destined for each other. But I’m willing to pretend I’m an INTP for at least a week, just to find out about that eccentric nature.
    Anyway I’m still interested in the Blackberry job.

  27. William Mitchell, CPRW
    William Mitchell, CPRW says:

    I am a sole proprietor and as such, have to live with my weaknesses. But at least I know what they are. For me, it is difficult to act on long-range goals becausde I am such a “task master”. If I do not schedule activities that have only long-term benefits, they never get done.

    I was an Operations Manager before starting my own resume writing service and “To-Do” lists dominated my day. Putting out fires and handling weekly tasks was what I did best. Now, as a business owner, I have to ensure that I dedicate time everyday to activities that have long-term effects, even at the expense of today’s task items. It has been a difficult adjustment for me’ but I am slowly morphing …

  28. Andrea
    Andrea says:

    Well, it does say “brazen” right at the top…missionary won’t really fit the bill I reckon.

    I <3 eccentric smart women… Then I know where the crazy is directly, because isn’t everyone crazy if you get to know them enough? I find it refreshing how weird people put it right out there. And if you’re with them, you get to be the only one in the world to watch them look up and imitate warblers in a public place…sigh…

    (by the way, I’m stoking up for a jerb interview tomorrow…your archives are great. Spank you, I mean, thank you very much.)

  29. tom
    tom says:

    Anal sex one week…”learn from Gov. Spitzer’s ho” the week before…

    What on earth is going on here?!

  30. Mark W.
    Mark W. says:

    I will admit it is difficult to stay focused on your six points in this post when there’s so much personal input included. However the six points are on spot when I look them over again. Also the comments start to (and sometimes actually do) rival the post when the post leaves so much open to interpretation and imagination.

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