Starting a Business is Like Dating a Hot But Needy Girlfriend

She’s the object of your obsession. You’ve always wanted to date her. Like since middle school. But you must be committed to her though. She’s demands it because she’s hot, remember?!

She’s emotionally unstable and insecure. You must give her all the emotional energy and time you have and then some more. Even when you don’t have any more to give. It’s never enough. Oh, and she can’t ever look fat in that dress. So constantly shower attention and affection her way.

She requires all of your attention. You can’t be looking at other girls, I mean, startups or jobs. She’ll wander off as fast as you can blink. Or worse, she’ll throw your crap out on the curb, or sell it on Craigslist.Β She knows when your spotlight isn’t on her.

She needs your singular focus. Hobbies and other things (like your silly workout routine) get cut because she takes all your time. Maybe some friends too who just don’t understand your relationship. She’ll also wake you up in the middle of the night with superficial needs like reminding her why she’s the only one for you. You will need to talk it out until the sun rises and you need to be at the office.

She gets super jealous.Β Like going from zen to nuclear war in 5 seconds. Seriously, don’t even think about looking elsewhere, or else she’s gone! And every other relationship will be looked on with skepticism and envy,

OH … if you make it a couple of years together … in some kind of miracle … she’s going to want kids, a new house, new clothes, a new car. And you get to start over with a whole new set of demands. πŸ™‚


UPDATE: Brad shared with me this video on the Hot/Crazy Scale from How I Met Your Mother. It cracked me up so I thought I’d share.

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14 thoughts on “Starting a Business is Like Dating a Hot But Needy Girlfriend”

  1. You are dead on n this post Cory! I recently left a good paying job that I loved for a small start-up being ran by a few casual friends. They had been trying to get me for about a year, and I had acted as a consultant for a few of their key product development stages. They took most of my advice and changed their business focus to my suggestions, so I thought they respected my input, right. After less than 2 weeks of me being on the job I had to quit. They were smoking the green stuff and getting in the hot tub during work hours. Seriously. Then asking ME why the process was slow-going. I looked them dead in the eye and told them that they needed to focus and get dedication, not just rely on me to do all the work. After all, in a five man video production team.. you need ALL FIVE! Haha! I take it as a lesson learned NOT to trust the promises but to trust the real dedication shown, even if they are sort of friends. Anyhow, sorry for the rant and great blog post. I look forward to gaining your insights often!

    • Joshua, ouch! I’ve told many people that I’ve had a great working relationship with my partners for the last 4.5 years, but I think it is increasingly rare to find that. Thanks for taking the time to comment! I got a good laugh doing the post. πŸ™‚

  2. Cory,
    No ‘flames’ here. πŸ˜€
    Thanks for adding a good laugh to my day!
    My startup is proving your post is a good comparison.
    Although whatever do you mean by “zen and zero to nuclear war in 5 seconds” ? πŸ˜‰

  3. Great post, Cory.

    There’s a fair amount of truth to this.

    The *real* fun begins when you have a startup business and then add a real-life girlfriend to that mix. Oh, did I mention I’m still stuck in the day job?

    I’m not so sure I’m looking forward to the responsibility end of your analogy with the kids (employees), clothes (new office space), and new car (I’m not sure what the business equivalent is).

  4. Cory, I can’t tell you how disappointed I am in this post. It promotes stereotypes, is mysogynistic and does nothing to endear yourself to the many female business owners who up until this point have supported iThemes and Startup Sofa.

    When I saw the title of your post delivered by e-mail, I thought – Oh, surely not? This must be some joke, right? Alas, no. You have shown a lack of respect for women and promoted the stereotype of women as needy, unpredictable, money-grabbing, vain, disloyal airheads. Is this the culture you have in your workplace?

    This phrase in particular – “she’s going to want kids, a new house, new clothes, a new car. And you get to start over with a whole new set of demands.”

    Come on! This is highly offensive! Women have had to put up with sexist and outdated attitudes in the workplace for decades, and it seems that you are intent on promulgating that attitude.

    Shame on you – can’t you find anything better to write about?

    • Vanessa, I’m sorry you took offense as it wasn’t intended to be offensive. This ENTIRE post can also be EQUALLY applied to a jealous boyfriend (but suffice to say, I haven’t dated any guys so I can’t really write to that).

      Having said that, my wife who I love, cherish, respect with all my being is a hard-core, smart, funny, beautiful feminist. I had her read over it to make sure before I posted. She’ll also be the first to say that you’ve got the wrong impression.

      And I’ll say directly you’ve taken this WAY too far yourself suggesting this is the culture in our workplace or lumping ME into those stereotypes?

      WOW! Wow! Wow!

      I would never intend to demean women in any way. I was merely trying to say that startups are the equivalent of a demanding, super jealous significant other. If that was missed on you, then I can’t help that.

      OK – back to happy blogging and other fun stuff! πŸ™‚

      • Cory, if you would never intend to demean women in any way, you have a funny way of going about it.

        And for the record, I didn’t suggest that this was the culture in your workplace, but merely asked you whether it was? Given the post you’ve just made, it seems a reasonable question, no?

        Nowhere in your post do you give the impression that these stereotypes could equally be applied to men, so no, I don’t think your message was missed on me.

        I’ve voiced my disappointment. I don’t intend to comment any further.

  5. Thanks for an awesome, honest post. Anyone that gets offended by this has totally missed the point. This isn’t about stereotypes about women, it’s about the demands of owning your own business.

    Until you’ve owned a very successful global company like iThemes, dealt with the incredible challenges and the difficult decisions that go along with that, I suppose it’s quite possible to miss the strong analogy being drawn here.

    Surely it must be hard work that could be easy to resent, but it’s worth it. And Cory can say whatever he wants about it.

  6. SO funny…and so true. I just spent the last two nights working past 1 am to take care of my “needy girlfriend”. Keeping the end goal in site and having a vision is getting me through it though. And knowing that there are others in my shoes…

    It would be great if you had sharing on this post…I’d love to share it with my social networks with the click of a button πŸ™‚

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