Response to: “So, You Want to Be an Entrepreneur –”

Kelly Spors’ at the Wall Street Journal recycles the ‘Questions to Ask Before You Become an Entrepreneur’ article that one can find every few months in the pages of Inc., Fortune, the WSJ and so on.   It’s here: So, You Want to Be an Entrepreneur –  (Update May 6, 2009, today ReadWriteweb’s Bernard Lunn posts an article hereUpdate on May 7, 2009, Bernard had another article, which I had further thoughts on here. )

Spors offers 10 questions—things like “are you a self-starter?”, “are you comfortable making decisions no the fly with no playbook?”—as a way to get started in this assessment.

This approach, these questions, are very cookie-cutter—they don’t get at the interesting and most fundamental questions that someone needs to ask him/herself.  As an entrepreneur who’s lived through this shift, I think I’ve got some useful perspective.

I’m going to provide what I think are the top few issues to consider.

How viscerally important is making meaning through creating this company to you?  I start by asking this question as entrepreneurship is a *HUGE* step into the unknown, To apply a paraphrase of Donald Rumsfeld, there are a big set of known unknowns (will you succeed?  can you and your family handle the stress of risk?  etc.) and there’s an equally or even larger set of unknown unknowns.  You can only know so much about what you are getting into; as a result, you had better have a pretty visceral need to go do this in order to take the step.  This isn’t about making more money, controlling your schedule, or whatever—the odds are stacked against you on all fronts there.  It had better be about you not being able to go to your deathbed without having gone for it.  I think its basically that stark.  I also think that even with this desire, it can still be a hugely difficult decision.

How persistent are you?  Persistence is not just about ‘don’t give up’ or ‘don’t take no for an answer.’ Its’ about staying positive, staying calm, staying on task.  My model for persistence is Dustin Hoffman’s Stanley Motss from Wag the Dog, and his standard answer to any crisis: “THIS is not a problem.”

His is a great model for anyone to hold onto as they go forth.   Nothing phases him, nothing can phase you.

Can you handle rejection?  This is related to persistence, but is so important that I think its useful to state twice.  Keeping persistence is of course vital, but hand in hand, you will need to be able to handle a lot of good, smart, well-meaning people telling you “NO” they won’t buy your product, they won’t invest, give you a loan, whatever.  This stinks.  You need a way to stay not only focused but optimistic in the face of this.

The late Proferssor Randy Pausch, author of the Last Lecture, has a great quote here:

The brick walls are not there to keep us out. The brick walls are there to give us a chance to show how badly we want something. Because the brick walls are there to stop the people who don’t want it badly enough.

For me, there are very specific things I do, almost like a checklist whenever I hear a firm “NO”.  These help minimize downtime I may have from the pain of rejection and keep me focused on the go forward.

How important and eager are you to learn new things—things you’ve never done before? This probably sounds the easiest to answer—”sure I want to learn new things!”  Maybe it is, but a word of caution.  Embarking as an entrepreneur means you’ll get pulled in new directions, stretched in new ways.  If you scare or frustrate easily at having to learn how to handle some totally different way of operating—if wearing all kinds of different hats (many none too glamorous), then this will be difficult.  You had better hunger for new adventures, new skills, disciplines and so on.  If you are someone who’s relatively happy with what you know and finds developing new taxing, then entrepreneurship will be a drag.

Now all that said, I’ve been an entrepreneur now for 18 months.  It has had moments of sheer terror.  It’s also had amazingly gratifying moments, with the opportunity (I hope)of more to come.   As one would expect, it’s far more volatile than my prior work at Microsoft.  At the end of the day, as much as I enjoyed Microsoft and think it remains an awesome company, the entrepreneurial route is one that’s been a great fit for me.  I’m passionate about what we’re building.  I’m learning and having fun.  And if we do our jobs well, we’ll have a great impact on our customers and our community.



Filed under business, entrepreneurship

2 responses to “Response to: “So, You Want to Be an Entrepreneur –”

  1. Leslie

    Thanks for the thoughtful article. You said “For me, there are very specific things I do, almost like a checklist whenever I hear a firm “NO”.”

    Can you elaborate on what those things are?


    • @leslie. Here’s my checklist of things that I do when I hear a firm “NO.”

      (1) if it came through email, get it into a folder that’s not my inbox, I don’t want it staring at me everytime I have to do email.
      (2) do not do email or take phone calls for roughly 2 hours
      (3) go to the gym, and get some exercise. for me, 45 minutes of cardio-work is a great cleansing agent.

      if the “NO” was harsh or degrading–and this happens–then I add that name to a list of people whom I wouldn’t invite to the yacht party i’d someday host when post successful exit 🙂 or whatever.

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