Serial Entrepreneurs: Why Keep Coming Back?

I have a certain friend. Maybe you know him, or perhaps you know someone like him.

My friend and I were talking yesterday. We were talking startups. In his 20's, he launched two different startups, and about a year or two in, he either ran out of money, got tired of the hustle, or both. Two times he tried, and two times he failed. 0–2.

Today, my friend’s in a different position. He’s working at an established company, he has a particular role to fill, he gets his paycheck every other week, and by all accounts, he’s happy with his situation. As he put it, he doesn’t have any plans to leave “this good thing I got now”— especially not for the extremely rough and rugged waters of entrepreneurship.

And this friend of mine, he’s absolutely flabbergasted that anyone who’s ever tried to build a startup and failed, could even seriously consider going back for more. As he put it, “I think these serial entrepreneurs get some sort of enjoyment out of inflicting pain on themselves. Working for the man is so much easier, stable, and certain. I’m much happier now,” he says.

By all accounts, it’s clear that my friend does not miss his life as a startup founder — like not one bit. He truly believes more entrepreneurs should give the “normal, nine-to-five” a try, and swears they may actually like it.

This conversation with my friend got me thinking…

Why do some entrepreneurs, whose businesses fail, come back and try again?

I mean failing a startup isn’t the same as failing a project at work, or failing a class at school. Building a successful startup requires a critical combination of inexhaustible work, spot-on strategy, endless sacrifices, and perseverance, perseverance, perseverance…did I mention perseverance? A failed startup can mean the layoffs of tens or hundreds of employees, the loss of thousands or millions of dollars, and the embarrassment of having to let your investors, advisors, family, friends, and even that pesky Techcrunch reporter know that your company didn’t make. You won’t, as you once boasted, be making it into the Elite 8 afterall.

Failing to make your company successful can deal a brutal blow to one’s ego and spirit (not to mention bank account). Not everyone can bounce back from an experience like this, so I’m really fascinated to learn more about those who do come back to give it another try.

To all the serial entrepreneurs out there, Why do you keep coming back? I’ve started a list here, but I’m hoping you can help fill in the gaps and blind spots. So, let’s get to it, shall we…

My startup(s) failed, but I’m doing another one because:

  1. Failure is relative. I didn’t fail; I just didn’t succeed according to your definition.
  2. I’m wiser now and can apply what I know to building a better company.
  3. Other people may not see it, but I do. I truly do see a better way this could be done, and I actually believe I can be the one to do it.
  4. I’m just as smart and capable as anyone. If they can do it, so can I.
  5. I don’t have a choice. There aren’t enough jobs; I have to create my own work.
  6. I don’t want anyone else telling me what to do. I want the freedom to decide what I do and when I do it. I want to be my own boss.
  7. I want to be rich. Sure, the odds are against me going this route, but if I make it, the payout will be out of this world.
  8. I want to be famous. I want to be remembered. I want to leave a legacy.
  9. I’d rather spend my life building my own dreams, than help someone else build theirs.
  10. I want meaning in my life, and building something I believe in gives me meaning.
  11. I want to be the best. Anyone who’s ever become the best in anything fell down at times. The key was, they didn’t stay there.

See anything that resonates with you? Have a different reason for building your startup? Share in the comments section below.


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