Serial Entrepreneurs and What Motivates Them

The WSJ has an excellent article titled The Secrets of Serial Success.  The “serial entrepreneur” is a mysterious beast and entrepreneurship sociologists have been poking and prodding at it for some time.  Most articles I read about the “motivation of serial entrepreneurs” falls short – this one nails a lot of the things I’ve observed and experienced.

My friends Tim Miller and Ryan Martens from Rally Software both have parts in the article.  Tim and Ryan had a nice success with their previous company (Avitek – acquired by BEA) and are now working hard at their next company.  They typify the “serial entrepreneur species” (of the “entrepreneur genus”.)

  • good to see brunonian entrepreneurs tom&tom leading the article!

    i would also be remiss if i didn’t mention andy sack and the amie street guys while on the topic – great people!

  • We’ve been looking at this as well in the context of performance.

  • Dave

    Does the term “serial entrepreneur” still apply if you keep doing it because you haven’t succeeded yet? Obviously the motivations there are quite different.

    Also, a species is a subset of a genus, not the other way around.

    • Sam


      I actually think there is no difference. Serial entrepreneurs start businesses not because they want one successful one, but rather just because they love the act of starting up. I think as a serial entrepreneur, whether a company we start succeeds or not is secondary to the feeling of turning an idea into reality.

  • The mythology of the serial entrepreneur is valid, but there’s another, darker point of view.

    What if these entrepreneurs, myself included, just couldn’t get hired to do anything else? What if the only way we have a reason to get out of the house every day is to start another company?

    More on that here:

  • One of the reasons we go back into another business is that you learn so much from each one that it’s hard to resist applying that experience, to greater affect, again to a different problem.
    Plus there is the allure of a truly creative occupation which isn’t a bad description of what drives entrepreneurs (and what often makes them poor managers of ongoing businesses!).
    And finally, my last start-up was during the latter period of the dot bomb. Today we have a completely different environment with amazingly powerful and inexpensive resources available. You really don’t need a lot of cash until you’re ready to scale. It’s really exciting.

  • @Dave – thanks for the biology correction. I really did get a 5 on my AP Biology test – 24 years ago. Think of it as biological dyslexia.

  • biggest point of the article: “it’s not about money”

  • Chuck
  • Anagha

    The bottomline : they do it for creativity and the risk associated with it. Also, the challenge of doing it. It is something akin to solving math problems when in school. You learn a new math principle, do one problem, solve it correctly and you want to do more ; you want to learn more and again apply that learning. The cycle goes on.

    No correction was required regarding the species-genus thing. Brad, you were right the first time.

  • it was a great segment. i liked the reinforcement on:
    -do what you like vs what you are good at
    -serial success can be a trend but not guaranteed
    -create–create, it isnt nec about the business, but we do know that is a bit naive
    -‘herd tigers’—build the right team of young turks who can execute.

    nice exposure for rally too!