Sisyphus For Startups

Posted on December 29, 2009
Filed Under Blogs, Business |

sisyphusPush the rock. If I had to sum up my advice to entrepreneurs in one sentence, that would be as good as any.

Backupify is my 17th business idea, if we define ideas not as flippant spur of the moment thoughts, but as something I seriously considered for more than a few weeks. Of those 17, at least 9 of them went to a stage where they took significant time or money. No home runs yet. Maybe this one will be. Maybe not. I can’t predict the future, so all I can really do is keep pushing the rock.

The question is, after 8 ideas that didn’t get off the ground, 4 that were seriously researched or prototyped but ultimately passed on, 2 that lost good chunks of money, 1 that made a little money, and 1 that sort of just hung around barely profitable and eventually faded out, why go for number 17 at all? Why not give up? The answer is that I’ve grown to love pushing the rock.

Sisyphus is somewhat of an idol for me. Maybe it is because he is such a spiteful bastard. The best thing that came out of my college philosophy class was the requirement to study Albert Camus. While I didn’t take to his ideas in general, I’m grateful for his work because he was the first one to expose me to the Greek myth of Sisyphus.

In case you aren’t familiar with the story, Sisyphus was a guy who did some bad stuff, and as a result, he was sentenced to forever push a big rock up a hill. Each time he approached the top of the hill, the rock would roll back down and he had to start over. I’m sure it was frustrating for him. But at the same time, I like to think that each time he started over, Sisyphus was a little bit stronger from the last push.

No one enjoys failure, but every single successful entrepreneur I know has failed at some point. Like Sisyphus though, they don’t give up when the rock rolls back down the hill. They start the push over. Some VCs have even written that persistence is the #1 trait they look for in entrepreneurs.

As I’ve come to know more entrepreneurs over the last few years, it is obvious that persistence is one of the few traits they have in common. They pursue idea after idea, day after day, doing the things others aren’t willing to do. I don’t buy this idea that you have to be extroverted or introverted or good at sales or tech savvy or rich or poor or young or old or smart or well educated. Some of those things help, but what really matters is whether or not you want to push that rock come hell or high water. What really matters is what you do when the rock rolls back down the hill and everyone is asking what the hell is wrong with you that you keep pushing that stupid rock when you are never going to get it to the top.

Those people don’t understand that once you push the rock for a while, you start to kind of like it. That’s why there are so many entrepreneurs who, after finally getting their rock to the top of the hill, decide to start over with a new rock to see if they can push it up a bigger hill, or do it faster this time.

So if you really want to be a successful entrepreneur, maybe instead of trying to be as smart as Bill Gates, as good a presenter as Steve Jobs, or as lucky as that Plenty-Of-Fish dude that so many startup gurus tell you emulate, you should really try first and foremost to be as persistent as Sisyphus. Push that rock, but don’t just push it when you feel like it. Push it when you are tired, push it when you feel bad, push it when other people tell you that you are wasting your time. Don’t expect pushing the rock to be easy. If it was, everyone would do it.

An entrepreneur friend of mine once wrote that you need to be a little crazy if you want to start a business. I think Sisyphus was crazy for pushing that rock, but I also think that, despite what the myth says, he eventually gets it to the top of that hill.


10 Responses to “Sisyphus For Startups”

  1. Tweets that mention Sisyphus For Startups : Coconut Headsets -- on December 29th, 2009 3:57 pm

    [...] This post was mentioned on Twitter by Rob May, Thomas Powell. Thomas Powell said: RT @robmay: Sisyphus for startups [...]

  2. Twitted by marsyk on December 29th, 2009 5:32 pm

    [...] This post was Twitted by marsyk [...]

  3. uberVU - social comments on December 29th, 2009 5:36 pm

    Social comments and analytics for this post…

    This post was mentioned on Twitter by robmay: Sisyphus for startups

  4. James E on December 29th, 2009 8:31 pm

    Funny - sisyphus_of_it is my hotmail account. I chose it because of the repetitive nature of the business…

  5. mebigfatguy on December 29th, 2009 10:36 pm

    Or perhaps, the moral of the story is how excessive torture can warp the mind — ala stockholm syndrome.

  6. Stephan Wehner on December 30th, 2009 10:31 pm

    Your backupify service looks like a nice idea, but I think the details will be difficult.

    I would think many bloggers will like the ability to back up their own blogs.

    (The “more” link under “Services We Support” doesn’t give you “more” however, it goes to the “sign up” page)

    Good luck,


  7. Cory Levy on December 30th, 2009 11:27 pm

    Wow! I have never thought of this comparison, but this totally makes sense. Great post!

    Cory Levy

  8. Mark Mawhinney on December 31st, 2009 1:02 am

    My first business was a success. My second business was a failure and just barely returned my investment. I’m working on my third now.

    Your reference is terrific and true.

    Barry’s book is excellent - great reference.

  9. nick huhn on December 31st, 2009 6:40 am

    as one who has spent too much time pushing other people’s rocks on hills in which i have no interest, i admire your tenacity and resolve. as such, i’d go to battle with or for you any day. keep pushing!

  10. Carnival of the Capitalists for 2010-01-04 | Carnival of the Capitalists on January 4th, 2010 12:03 pm
  • About Rob

    Rob is co-founder of He likes value investing, the Rolling Stones, college basketball, artificial intelligence, economic history and people who think independently.