How to Stop Being Nice and Get What You Really Want : Under30CEO How to Stop Being Nice and Get What You Really Want : Under30CEO
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How to Stop Being Nice and Get What You Really Want

| December 11, 2012 | 29 Comments

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.

About the Author: Matt Wilson

Matt Wilson is co-founder of Under30CEO. After two years traveling and working from his laptop, Matt's official title became Adventurer in Residence, heading up Under30Media's travel company Under30Experiences. If Matt is around he will be easy to spot as his long luxurious hair is generally flowing freely in the breeze.

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Category: Personal Branding, Startup Advice

  • steeve schira

    very helpful! should be a subject for a management class…

  • Ulrico

    I think there’s a positive message in this but I really don’t agree with the bottom line. Our parents’ generation of business operates on these social proofs – be a douche bag to get what you want. Modern business which operates on richer fair value exchanges is more about good people skills, and people WANTING to impress and be lead by you through likeable leadership traits. I do however think that most entrepreneurs, particularly sensitive people, allow themselves to get trodden on which of course affects success rates.

    If I were to re-title the article, it would be “How to be postured and get what you really want”. Certainly wish I learnt that earlier on in life.

  • Jamie L

    Brilliant article, Matt.
    @ Ulrico: He wasn’t advocating that we should turn into douche bags to get what we want. He’s merely saying that there is a correlation between being highly successful, and being a difficult person. Pushovers don’t make good entrepreneurs, they make good employees though.

  • Sushrut

    This is awesome. Great stuff, Matt.

  • MattWilsontv

    Hey Jamie– my sentiments exactly!!! Thanks for expressing.

  • MattWilsontv

    Heu Ulirco– check out Jamie’s comment above.

    I’m not saying be a douche bag, or mislead / be postured. I’m merely suggesting that as a leader you should trust your gut, stand strong for what you believe in, and express that tactfully to others.

  • MattWilsontv

    Thanks Sushrut!

  • MattWilsontv

    … and where you really learn it is outside of the classroom!

  • Rich

    In my experience, people just need a focused direction. They need someone to tell them that what they’re doing is complete BS, and that the way it should be done is ____. I think the “being difficult” part is just a feature of being a great leader, but the real core trait is that you accept no compromise, and execute on your goal no matter what; even if it means pissing some people off in the process.

    Please remember that Steve Jobs was made to quit Apple in 1985 because of his temperament. And Donald Trump, from what I’ve heard, is only a jerk on TV.

    People don’t like being told that what they’re doing is wrong, nor do they want your bad opinion. People are attracted to someone who knows who they are, and will just stick at being that person. What they do want is someone to critique them objectively, and if it means that you’re a dick, then so be it.

  • Jay Weinberg

    Great thoughts Matt. As others have commented, it’s not about being mean or nice. The formula seems to be: Strong Vision + High Standards = Difficult to Work With. It also equates to success more often than not.

  • Jodi Blackwood

    So timely — thank you! As a business etiquette specialist, I emphasize the importance of treating people with respect — and that includes yourself. It is possible to be tactful and courteous to others while asking for what you need; it doesn’t have to be one or the other. It’s a matter of choosing your words, being aware of your facial expression and body language, and as you say, knowing what you want and asking for it.

  • MattWilsontv

    Thanks Jay, I think this is a solid formula.

    What the chart doesn’t entail is DRIVE and DESIRE. I’d like to see where Fred Wilson would put that on the Z Axis… i think that’s more important than anything.

  • Ulrico

    Appreciate the response, Matt. I entirely agree with your last sentence here, my apologies if I’ve misconstrued anything. I just don’t think “dog eat dog” has a place in the modern business world anymore.

  • MattWilsontv

    No problem Ulrico. The last sentence in the article about being like Ari or Arrington was a little exaggerated in order to make a point. When you struggle with this type of thing, as I do, it helps to put yourself into character and think, okay, “what would Ari Gold do?”… He’d ask for what he wanted and be bold.

    Thanks for reading and thanks for not being a douche, haha.

  • MattWilsontv

    Really cool Jodi, if you are interested in writing an article on how to be bold, yet following business etiquette I think it’d be a great followup. Feel free to contact jared @under30ceo .com

  • MattWilsontv

    Hey Rich, I think this is a really good point about the people on television– it obviously makes good television and is exaggerated but make no mistake, these businessmen / women, know what they want, and know how to get it.

  • Josh Newall


    Good stuff. There’s most definitely a strong case to be made for taking on this type of attitude in your professional career. By being much more direct and aggressive, you almost indirectly make a clearer path up the ladder as many people tend to back off from people like, let’s say, Ari Gold. With less people willing to challenge you, the scaling becomes all the easier.

    Only comment I would make is how critical it is to keep in mind that time and refinement are what will make or break this type of attitude adoption. Do it to early and you’ll get crunched. Do it in a way that’s obviously not genuine and you’re mocked. I’d suggest to anyone, in regards to this, to ensure you’re at a level of respect among the office to take on this type of role. And make sure you do it in a way that’s refined to you.

    Sorry guys, but I hate to say, most of us just don’t have it in us to be an Ari Gold. At least not authentically. That takes decades…

  • MattWilsontv

    Hey Josh, i completely agree here. If you are authentic, listen to your gut, tell it like it is, and stand for what you believe in, then you are much more likely to be successful. Do this in an authentic way, and people will catch on every time.

    Thanks for your insights.

  • Homeopath

    Important to distinguish between assertion and aggression. Everyone has a gut response to aggression, but most people in business appreciate assertiveness, it takes strength to lead.

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