Entrepreneurs Need Gumption To Succeed

Gumption is the ability to continue to try new things with confidence, in spite of past failures. Entrepreneurs need this to debug problems and build things that don’t exist–yet.

Entrepreneurs Have Confidence, Inspire Teamwork, Plan for Iteration, and Focus on Impact

We’ve recently gone through a mid-year re-planning exercise and one of the questions we asked ourselves was what were some key characteristics of the successful teams that we have had the good fortune to work with over the last five years. We came up with a short list as it related to how they approached bootstrapping.

  • They believe that they can create something of value. They proceed with a quiet confidence.
  • They are part of a team because they value effective collaboration and believe that they can accomplish more in the team they are in than on their own.
  • They don’t assume that a new initiative or product will succeed on the first try, so they plan for iterations. This means spending a small amount of time planning, keeping careful notes and/or developing a checklist or two, and updating them in response to new failures.
  • They don’t keep trying the same thing if it didn’t work, they make small changes and see if they have an impact.

This is not a horoscope, here are some examples of the opposites:

  • Most people that want to make a lot of money in a hurry, don’t.
  • If you are committed to succeeding entirely on your own you probably won’t. As one of our clients remarked “it takes a village to raise a start-up, I am calling in favors and asking so many folks for help and advice that I would never have anticipated reaching out to.”
  • Most entrepreneurs who stake everything on a new business idea working perfectly, keeping no funds or mental energy in reserve, don’t have the ability to maneuver around obstacles or recover from errors.
  • If you take the same product/idea/demo to two or three dozen people and nobody gets it, there may not be smarter prospects. It’s probably your product, your presentation, or your idea of who should be interested that need adjustment.

Obviously there are many other factors, but as I reflected on our list, I realized that the successful entrepreneurs had gumption, which is a mix of initiative, resourcefulness, and common sense.

Zen and The Art of Motorcycle Maintenance on the Value of Gumption

Robert Pirsig devotes chapter 26 of “Zen and the Art of Motorcycle Maintenance” to a discussion of gumption. I re-read this chapter over the weekend and found some excerpts that are particularly on point (links added):

I like the word “gumption” because it’s so homely and so forlorn and so out of style it looks as if it needs a friend and isn’t likely to reject anyone who comes along. It’s an old Scottish word, once used a lot by pioneers, but which, like “kin,” seems to have all but dropped out of use. I like it also because it describes exactly what happens to someone who connects with Quality. He gets filled with gumption.The Greeks called it enthousiasmos, the root of “enthusiasm.” which means literally “filled with theos,” or God, or Quality. See how that fits?

A person filled with gumption doesn’t sit around dissipating and stewing about things. He’s at the front of the train of his own awareness, watching to see what’s up the track and meeting it when it comes. That’s gumption.


The gumption-filling process occurs when one is quiet long enough to see and hear and feel the real universe, not just one’s own stale opinions about it. But it’s nothing exotic. That’s why I like the word.

You see it often in people who return from long, quiet fishing trips. Often they’re a little defensive about having put so much time to “no account” because there’s no intellectual justification for what they’ve been doing. But the returned fisherman usually has a peculiar abundance of gumption, usually for the very same things he was sick to death of a few weeks before. He hasn’t been wasting time. It’s only our limited cultural viewpoint that makes it seem so.

If you’re going to repair a motorcycle, an adequate supply of gumption is the first and most important tool. If you haven’t got that you might as well gather up all the other tools and put them away, because they won’t do you any good.

Gumption is the psychic gasoline that keeps the whole thing going. If you haven’t got it there’s no way the motorcycle can possibly be fixed. But if you have got it and know how to keep it there’s absolutely no way in this whole world that motorcycle can keep from getting fixed. It’s bound to happen. Therefore the thing that must be monitored at all times and preserved before anything else is the gumption.

Robert Pirsig outlines several techniques for maintaining gumption in the balance of the chapter. I took away three key habits appropriate for entrepreneurs:

  1. Keep a careful log of decisions.
  2. Avoid premature diagnosis: continue to correlate all of the facts against whatever hypothesis you are relying on.
  3. Re-evaluate priorities based on events and new information

He gives a memorable description of the “South Indian Monkey Trap” that’s worth adding to your “perhaps I have mis-assessed” checklist:

[T]he most striking example of value rigidity I can think of is the old South Indian Monkey Trap, which depends on value rigidity for its effectiveness. The trap consists of a hollowed-out coconut chained to a stake. The coconut has some rice inside which can be grabbed through a small hole. The hole is big enough so that the monkey’s hand can go in, but too small for his fist with rice in it to come out. The monkey reaches in and is suddenly trapped…by nothing more than his own value rigidity. He can’t revalue the rice. He cannot see that freedom without rice is more valuable than capture with it. The villagers are coming to get him and take him away. They’re coming closer—closer! — now!

Can you let go of what you have to allow yourself the freedom to become what you want to be?

That takes gumption as well I suppose.

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