The Entrepreneur’s Chip on the Shoulder

I’ve always had an entrepreneur’s chip on my shoulder — a sense of inferiority to other tech entrepreneurs.

I’m not based in Silicon Valley.

I failed at raising venture capital.

I was rejected by the prominent tech center in town.

Only, the constant rejection by the “superior way” fueled my motivation even more.

It can be done anywhere.

It doesn’t require venture capital.

It doesn’t need approval by the community.

Entrepreneurship is hard. The failure rate is high. Yet, success happened.

Perhaps it was the team. Perhaps it was the market. Perhaps it was timing. Likely, it was all three.

In reality, we’re all making it up as we go. The best we can do is look to learnings from those that have gone before us. We learn, we grow, we encounter new challenges — the cycle never stops.

Use the chip as fuel. Find the inner motivation. Make it happen.

6 thoughts on “The Entrepreneur’s Chip on the Shoulder

  1. David, totally understand and agree. While we did raise venture capital – it was all outside of Atlanta. We too were rejected by the local tech incubator. We had a myriad of unbelievable situations here:

    (a) a local investor fell asleep during our presentation.
    (b) another personally insulted me and my co-founders non-stop for an hour.
    (c) another local VC not only didn’t invest in Kabbage, but actually had a call with a west coast VC who was ready to issue us a term sheet and talk them out of the investment based on their belief we would fail.

    I had friends and family tell others that I was unemployed, instead of saying that I was starting a business even though they knew that was the case.

    I’ve been trying to knock this chip off my shoulder for a while but the meter still hasn’t run to empty on it. Maybe one day.

    But reality is that these are just some of the multitude of challenging things that happen when you’re trying to build something from scratch. Perhaps they’re necessary hurdles to separate those who will ultimately make it and those who might not. Thick skin is an absolute necessity.

    Great post.


  2. Being a successful entrepreneur is hard. You have to have the right product, the market conditions, the right team, the right technology, the right mentors, the right IP, the right attitude, the right spouse…. and, a little bit of luck.

    Everyone once in a while I see an entrepreneur who has all this and more; I call it good “mojo”. David- you have always had good “mojo”. Thanks for all you do for the entrepreneurial ecosystem. You make us all better. -Make it Happen!

  3. I would love to discus this more. I’ve built my past businesses somewhat relying on the same chip on my shoulder.

    But as I reflect, there must be another way. This chip on the shoulder requires a deformed view of ones self… deep insecurity… the fundamental identity of the founder being on the line and at risk at all times. In my case this got to a point where my identity and the identity of my business were fused – ie. failure of business would invalidate my self worth.

    We are valuable independent of the success or failure of our businesses but it seems this deformed view of personal value and the need for others to affirm and value us based on “success” is the main engine you are claiming will produce against all odds results. I believe that you are right, this is a powerful motivator, but there must be a better way, a psychologically more healthy way. As I embark on my next ventures, I hope to find a better path. This time around I am finding intrinsic motivation in my calling to build and create and insatiable desire to find world changing solutions to compelling problems.

  4. Great/true post and comments — you have to power thru the many failures you encounter somehow by believing you know better than the naysayers out there. Not that you shouldn’t listen to their concerns, questions your beliefs, or make sure you’re not just obstinately wearing rose-colored glasses. The chip on the shoulder comes from a weird mix of insecurity and self-confidence, with some self-righteousness thrown in, all leading to a desire to prove that you are right and this project or model can succeed.

    If/when you do have success, VC’s and other investors believe you more — everyone tends to be backwards looking, but you have to stay looking forward. Success can also lead to not enough questioning of your assumptions/plan (by them or yourself) or dampen motivation, both of which can also be a problems, it’s why you never want to totally lose that chip either! But most people have more failures than successes, it’s why you need to get up to bat often, keep failures small and let the successes run.

    As you say, the cycle never stops, until you decide to stop playing the game or focus on coaching others how to play it. Or as John is exploring, get outside your ego to try to solve deeper problems benefitting society. But still seems you’d try to prove to naysayers that your beliefs are correct and you can make impact.

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