What to do About that Chip on Your Shoulder?

Posted on May 17, 2012 | 60 comments

What to do About that Chip on Your Shoulder?

I’m fond of saying that I look for entrepreneurs that have a chip on their shoulder. That they have something to prove. That they’re not afraid to stick their noses up to the establishment.

I have always felt this way. It’s something I kind of seek out. I guess my thoughts are that if you’re part of the country club you have a vested interest in protecting the existing order and that disruption happens more from those that are on the outside wanting to change the rules.

I’m ok with founders who have “father issues.” I like people to have a healthy bit of motivation derived from wanting to stick their middle finger up at somebody who once dissed them or held them back.

It’s a certain edginess that I like. Grit.

In fact, I think those around me must tire of my repetitive advice,

“Be careful of wanting to be liked too much. It leads to bad decisions. It’s your job to be polite and inquisitive but skeptical. To be liked? To fit in? That’s herd mentality.”

I’ve written about similar topics:

1. Entrepreneurs Should be Respected, Not Loved
2. Why I Give Direct Feedback

I have a healthy appetite for working with immigrants or children of immigrants. I am a product of one so maybe there’s resonance there. But they’re seldom country club kids. [relax, I mean “country club” as a metaphor, I’m not hating on you just cuz you were good at tennis & golf.]

I’m looking for the Visigoths, not the Roman.


And this is the point of this post – be careful about your chip.

Edgy “change the world and eff the establishment” chip is different than “all you haters suck and why won’t anyone back me wah wah wah” chip.

Here’s a story.

I was at a conference 18 monts ago or so. I met an entrepreneur. He sought me out in the hallways. He has the “perfect business for me” given my blog commentary. Would I hear him out?


Well – he had this awesome platform that was super technical – great IP. He was from Harvard. Smart – check. He had raised a few million dollars – social proof. But the more he spoke the more he kept complaining about his existing investor. They were unsupportive. They were terrible bordering on unethical. He has so much negative energy it was draining.

I had no doubt he was telling the truth and was probably right. But he seemed so beat up and bitter that I doubt he will ever attract more capital. The chip was misplaced. Was on the wrong people. Investors screwed you a bit? Yes, that does suck. So either leave and start fresh or bite your lip. Nobody wants to get excited about spending time evaluating a company with a miserable CEO. I told him as much.

And usually it’s much more subtle.

I recently was with a group of investors and watched an entrepreneur try to pitch his concept. The investors asked some cynical questions. It would be easy for the entrepreneurs to say, “What a dumb freaking question. Why are you guys all the same?” But I guess that wouldn’t get very far.

But his body language and tone said it all for him. Exasperation. Frustration. He clearly didn’t want to be doing this. Yet it’s his job. And it’s his job to do it with a smile on his face.

Another friend of mine has been out raising his first institutional money. He has tried to go down the angel route, too. He has been turned down a lot. It’s starting to show in how he talks about his company. He seems despondent. When he pitches he seems like a dog ready to be kicked. When he responds he isn’t earnest – he seems frustrated because you asked the same questions as the last 5 guys who turned him down.

I told him,

“Trust me. Every great entrepreneur has been turned down dozens of times. Laugh it off! Wear it like a badge of honor! Hell, most entrepreneurs who were funded by VCs were probably told ‘no’ by that exact same VC one time before!

That’s what motivates them – turning a ‘no’ into a ‘yes’

You ain’t gonna do that with your negative energy.

So [prominent angel] said ‘no’ and was a dick. Get over it. The best revenge will be to be successful so you can be smug around him for the rest of your life!”

It sucks but trust me if you have a chip on your shoulder that says, “How could you guys fund yet another Pinterest competitor and you won’t even give my original concept a chance?” it will show. People will know. You will either give off frustration or lack of confidence. Neither is good.

I don’t mean to go all New Age on you. But trust me – before the meeting force yourself to smile and laugh out loud. Get yourself in the right mental mindframe. Remind yourself, “This is going to be a great meeting. Even if he says ‘no” I know it’s his job and I’m going to be thankful.”

When you start thinking positive and confident thoughts you start showing it non-verbally. When I meet with somebody I don’t really like and when they’re speaking I literally sometimes think out loud in my thoughts, “He’s not so bad. He’s a good guy. It will all be good.” Or whatever. And I hope that this avoids me openly showing disdain.

So remember:

– chip on your shoulder, “I’m going to change the world, just try and stop me” = good.
– chip on your shoulder, “Investors are all lemmings and I’ll prove it”  = not so good. Even when you don’t say it out loud – it shows.

Image courtesy of BlakeSpot on Flickr

p.s. No. I didn’t spell check this. Get over it. I’ll fix it later when I have time. Right now it’s midnight. I’m at a hotel. I need some sleep. Feel free to ping me with corrections but please don’t be annoyed.

p.p.s. Yes. I do get people who occasionally show a big frustration with me that I don’t edit my posts more carefully. C’est la vie.

  • http://petegrif.tumblr.com/ Pete Griffiths

    Very true.

  • http://wildirishguy.com Damon Oldcorn

    Just so you know I am perfectly balanced ……

    I have a chip on both shoulders…….

  • http://www.Chain-Cable.com/ Allan @ Aircraft Cables

    The fact that you added the PS and PPS into the post means you had the chance to spellcheck and edit and you chose not to. Way to go. Stickin it to the man! Hypocrit. Just kidding. Great post.

  • Toby

    Really good post—I heard recently that one thing that makes a good entrepreneur is to have had trauma in their childhood–a drunk for a father—a broken home etc.  Early trauma will forge that desire or need to succeed.  It breeds an early reliance on self.  That is why people who grew up dirt poor often become more successful than their moneyed classmates.

  • http://www.incentivibe.com/ Adeel vanthaliwala

    Thanks for the great read.  It frustrates me to see how many Founders forget that raising funds and running a company is not an event or an ambition to reach an event … it’s a process in which tenacity, perseverance and “Grit” gets you through.  So, a few people turned you down – that was an event.  Turn it into a process whereby you strive to turn some of them into a yes over a span of a few weeks/months.  That in-and-of-itself is an amazing journey. 

  • http://www.incentivibe.com/ Adeel vanthaliwala

    Exactly – once you see this as a process then it is very easy to set your mind.  “I may get rejected this time, I will learn why, go home and figure out a way to get yes the next time with the new information.”

  • Brooklean

    Turning down a good opportunity is a bad idea. Turning it down just because the opportunity provider was frustrated is even worse. 

    You meet a hot girl. She is a little bit frustrated. Do not miss the chance. It would be more difficult to get a date if she were content.

    You meet a potential customer. He is a little bit frustrated with his current vendor. Do not miss the chance. It would be more difficult to acquire him if he were content. 

    You meet a product owner. He is a little bit frustrated with his current investors. Do not miss the chance. It would be more difficult to partner with him if he were content. 

    Can we blame the “there are other fish in the sea” mind set for the irrationality? 

  • Kamal Shah

    Thanks Mark.  Great post.  I’d like to add a few thoughts.  I think if an entrepreneur’s chip comes from passion, confidence in their idea and drive to see it through it will be seen in a positive light by others and not as an F! U.  Also, being an entrepreneur is hard and negativity and whining don’t show others that you have the ability to be adaptable to change, take charge of situations you can control and deal with situtions you can’t and keep ploughing forward – hopefully with some humor and grace.  

    p.s in support of you not spell checking I intentionally left a typo in here!

  • http://jocelynauco.in/ Jocelyn Aucoin

    What about “mother issues?”  Talk about a chip on the shoulder!! 

  • http://twitter.com/brian_sirkia Brian Sirkia

    I recently drafted an email to an investor I felt was taking a bit longer to close than was necessary and had an advisor read over it first. He said that even if you feel you’ve been treated poorly or without due respect, you should never be annoyed or be indignant around them. Even if this deal isn’t going well, you never know when you may deal with them in the future. My approach for the raise now is to always try and interact in an irreproachable manner. For example, instead of saying “I’m going to NYC to do a roadshow next week, get in now or I won’t come back to you because we’ve been talking for months already”, say “I’m going to NYC to do a roadshow next week and wanted to see if you would like to meet beforehand.”