Want the key to making more money? Stop being so damn nice.

I’ve worked on saying “No” for way too long, and I’m still not good enough. For me, it’s nature and nurture. I’m pretty sure I was born nice… On top of that, I was nurtured by the nicest woman alive—my mother.

Why isn’t my business more profitable and more streamlined? Because all too often I let other people have their way.

Entrepreneurs: Are You Too Nice?

When someone is doing work for me, why am I gentle and kind in my critiques instead of getting what I actually want? It’s a waste of both of our times. Why don’t I demand perfection out of everyone around me? Why don’t I try harder to negotiate terms or ask for discounts more often?

### Sh*t, I just did it again, I’m on a flight to Costa Rica, and I just let the flight attendant pass because she looked busy. Do I care if she thinks I’m over assertive?  No. I’m hungry. ###

Nice Guys Make Less Money

Legendary venture capital investor Fred Wilson explains that Founder’s success and degree of difficulty to get along with are directly proportional.

Instead of saying, “I have to chose my battles carefully,” start saying, “I have to choose more battles.” Start becoming more difficult to work with. Start trusting your gut and demanding that others play by your rules.

It’s no coincidence that the most successful entrepreneurs aren’t very nice. Why do the wealthiest people seem to actually act like the investors on Shark Tank?

Barbara Corcoran enjoys embarrassing people on Shark Tank. Steve Jobs would fire anyone in an instant. Donald Trump is notoriously a jerk. Mark Zuckerberg is villainized on the big screen… As rapper J.Cole says, “No more Mr. Nice Guy, Hello Mr. Nice Watch.”

I’m not saying you need an ego. I’m not saying you have to be a mean person. I’m not saying you need to turn into a capitalist robber barron. I saying that you can make positive impact on the world by being less nice.

How to Ask For What You Want

 Just do it! Ask yourself: Do you want to be liked or do you want to make more money?

You don’t get what you don’t ask for, so stop being sheepish. But here’s the good news: the person whom you asked for what you wanted probably won’t mind. Just learn to do it tactfully. You can ask for your way with a smile.

Be truly decisive in your decision making. Practice answering in “yes” or “no” fashion. Visualize saying exactly what you want. Every skill you have can be practiced. The more you do it, the better you’ll be at it and eventually it will be habit. Can’t do it on your own? Hire a coach and find an accountability partner. Stop sugarcoating things and be direct. It’s a waste of everyone’s time and it takes more energy. Take that energy and put it into something positive.

Next time you need help being bold, get into character and visualize yourself as Techcrunch’s former A**hole CEO Michael Arrington or better yet, Ari Gold from Entourage.

Do you want to go through life as someone who never got what they wanted? Start asking for what you want today.

Matt Wilson is Co-founder of Under30Media.  Join Matt on their newest adventure: Under30Experiences and sign up to hear about their Microfinance Surf Camp to Nicaragua and Startup Iceland Adventure 2013.


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