Why I Fired My Best Friend : Under30CEO Why I Fired My Best Friend : Under30CEO
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Why I Fired My Best Friend

| December 21, 2011 | 32 Comments

“Matt, you just aren’t the type of person that makes those around you better,” I was once told…. while I don’t like to swear, all I can think is “f*ck that guy”.  I’ve never been more insulted in my life.

That’s Bulletin Board Material

I should pin that quote up in the locker room, or frame it in my office, because every time I think of that, it motivates me. Our Under30CEO speaker Alexis Ohanian, co-founder of Reddit.com recently told our crowd in New York to make themselves a “wall of negative reinforcement.” While it’s not everybody’s style to pin up their competition’s face and throw darts at it, it certainly works for me.

Demand More from the People Around You

Think of the five people who you spend the most time with. Like it or not, that’s who you are most like. If you aren’t spending your time with quality people, the quality of your own life is going to suffer. Take a good look around you and ask yourself if your friends are holding you back and if so, how you are going to fix that. In fact, forget holding you back, are your friends the type who will make you better at everything you do?

I’m not saying that all my friend’s are at the top of their game in every single category. Yes, I’ll be your friend if you are down on your luck, but the people I am closest with have a mutual understanding that we are in this together, and we’re going to make each other better.

Don’t Be Afraid to Fire Your Friends

If someone who you have respect for is not living up to your expectations as a friend, or does something detrimental to themselves or others, let them know. I’m very non confrontational by nature, but my friends know, and especially my best friends, that I will tell them how I feel if they are letting me down, for the good of everyone around.

This fall I fired my gym partner. Plain and simple, he was holding me back. If I have to give you a Vince Lombardi speech every time we go to the gym, you aren’t holding up your end of the bargain. That’s weak.

I Want To Be Surrounded by the Best

I want to be the best at everything I do. I don’t talk about it much, because I don’t want people to think I’m pompous or holier than thou, but I think it all the time. I want a gym partner who’s going to motivate me, put me through the ringer, teach me about new methods of training and push me to be the best. I aspire to perform like a world class athlete because I think it’ll make me better at all aspects of life, including business.

By the way, since firing my gym partner, I’ve absolutely crushed all my old plateaus. It’s opened me up to a whole new world of training, I’ve learned tons from working with people with Olympic level knowledge and I am not slowing down anytime soon.

If You Are Going to Do Something, Do It All Out

One of the biggest compliments I’ve ever received was that I was the only person in the world that gets pumped before every single thing I do…even to play Madden… I was thrilled. Whether you are working out, doing business, answering emails, partying or going surfing, you might as well go at it 100%. Exuding this type of energy makes life that much better and people feed off of that.

Audit Your Friends

I realized that I had a huge problem taking care of my personal finances. I used to hate paying bills, never used to properly budget and would get charged fees because of my own carelessness all the time. That’s pathetic for a businessman and I decided to make a change. To master this area of my life for good, I called my best friend, and at the time, gym partner. We agreed to sit down once a month, scrutinize each other’s finances and hold each other accountable. Now, I have to make a formal presentation and show him where every cent of my money went. When he runs up his AMEX bill, I know about it; when I go over my minutes on my phone bill, he’s there to yell at me. It takes a tremendous amount of trust, but having a commitment to an accountability partner has created incredible results.

I Fired Him For That Too

December came around and it was time to audit each other before the holidays. I took care of all my deliverables, budgeted properly, saved a ton of money and completely owned that area of my life…Unfortunately, it looks like my personal finance partner isn’t living up to expectations…

“The holidays are a terrible time to start budgeting and work on your finances,” said his text message canceling our monthly audit session.

Is this the type of person I want to hold me accountable? I don’t think so. My tongue in cheek reply… “We need a break. We can still be best friends, but this year I’ll be asking Santa for a new personal finance partner.”

Brutal? Yes. Because we have the type of friendship where I have to be? Absolutely. I want my friends to be committed to what they say they are going to do.

New Year’s Resolutions are a Fallacy

Everyone knows that. If you are going to make a resolution, make it now. If you are going to get your finances and fitness in order, don’t waste your money / get fat this holiday season. Have some sense about yourself. Have some self control.

I love the kid and he’s an amazing friend, just not the person to get me to the next level in these two areas of life. I hope that by writing this post, you’ll take a look at the people around you and be honest, with them and with yourself.  Ask them the tough questions. Urge your friends to want more out of themselves and make your friends ask more of you… As for my friend, maybe this will be his bulletin board material, because he’s not making me better right now.

Matt Wilson is co-founder of Under30CEO and for those of you wondering, this friend is not @JaredOToole, nor did he fire him.  Connect with Matt on Twitter @MattWilsontv.

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: Startup Advice

  • Maria Joyner

    This is the best article you have ever written. THANK YOU for the brutal honesty and sharing this article. Separating oneself from a best friend is one of the hardest things for young entrepreneurs to learn. I went through it too. It sucked but I am so much better off for it.

  • http://twitter.com/ColorTheGlobe .com Seeks Investors

    Somehow I feel sad when reading this story.

    anyways go to color the globe.com, add us on facebook, and see our first speech this tuesday!

  • http://spiritsentient.com JasonFonceca

    I agree with Maria!  I cheered for this story!

    Society has become numb to so much for the sake of “keeping our same circles” and “not rocking the boat”

    Good for you Matt! Good! For! You!


    I write about this often because I’m like the friendliest, most popular guy in the world. Or I was most of my past, and I went through what you did.

    To build on what you’ve offered, I have a series called Rocketships Or Cars: The Art Of Friends ( http://spiritsentient.com/rocketships-or-cars-the-art-of-friends )  which helps people make some of the ‘tough’ decisions you made.

    Thanks for being awesome.

  • http://WhoIsRicardo.Com Ricardo M Rodriguez

    They do say…

    If you hang out with 4 broke people, who do you think the 5th one is going to be?

    This is something I’m in the process of doing. I find myself going to networking events, joining a toastmasters club, attendting workshops, reading more and more books, etc Then look to my friends and they’re definitely not in the same page as me. Even if we have been friends since high school, it’s time to upgrade. Your network is absolutely correlated to your networth.
    Great post Matt, thanks for sharing.

  • http://www.freedomvoice.com/ PRHales

    This is an absolutely great article. So many entrepreneurs get started with a friend, but once the partnership becomes one-sided it’s very difficult to bring it up.

    If possible, I think it’s best to keep close friends and family out of your business life for the sake of everyone involved. It’s easier to tell a friend you can’t hire them than it is to fire them.

  • Nicholas Tart

    I’ve been thinking about this a lot lately, Matt. The thought of firing your friends also brings up the argument that you’re putting business before relationships. I’m not a fan of that, but I recognize the value of surrounding yourself with like-minded people. Have a Merry Christmas and I wish you the best in 2012!

    P.S. Ray Land told me great things about your events in NYC. Can’t wait to come to one someday. 

  • Atlas


    I’ve fired a few people over my young life, I think what I need now is to surround myself with more people who have the same level of intensity and ambition to be and do something real and amazing.

    I’m terrible with my finances, I’m surprised I’ve made it this far in my business, I’m a culprit of late bills to then I get surprised when I get hit with extra charges. O well.

    This made me laugh – it was like reading my own story.

    At the end of the day changes need to made, may as well go all out with everything right – bring my (A) game to every dynamic of my life.

    My foot is on the gas. Period.

  • Neely Raffellini

    Every successful entrepreneur or those who don’t want to live by the status quo have been told some of the same things that your “friend” said to you. Aren’t they awesome motivators?

  • http://twitter.com/MichaelEFear Michael Fear

    Easily one of the best articles ever posted on Under30CEO. 

  • Huntfour Anarnia

    So my question is, how to know when to separate oneself? I often feel like I am in constant need of an upgrade, change, makeover or just to simply reinvent, yet I remain with the same crew because trying to create a new one just seems so not genuine.

  • http://revplace.com/ Aaron Wright

    This subject has been on my mind a lot lately. It seems like many of my friends would rather sit around and mope about not having a job than to take action and do something about it. It has gotten to the point where I would rather not hang out with them anymore. Funny thing is that they are also the ones who tell me to find a different job if I want to be happier. My response is usually along the lines of “How’s that job searching thing working out for you?”. You can’t have people holding you back from your own success in life. You need to take action.

    Great post. Thanks for sharing.

  • http://under30ceo.com MattWilsontv

    Hey Aaron, glad you liked–don’t forget that when you are friends with someone you should add value to each other’s lives.  It doesn’t have to be anything big, like I talk about this in an article, even if you enjoy someone else’s companionship, that’s often enough value.

    Hope you can lend a hand to your friends and help them out in some way, even if it’s just by setting a good example. 

  • http://under30ceo.com MattWilsontv

    Hey Atlas, glad you you could relate.  Think about teaming up with a friend to stay accountable for your finances!  

    Hope you have a big 2012.

  • http://under30ceo.com MattWilsontv

    Hey Nick, great to hear from you.  I like to separate business and pleasure very much….even though I have this crazy “I want to train with the best” mentality, it’s an escape from business.  I just need people around me who can get me to the next level. 

    As far as my friend–he know’s hes my best friend and knows the minute he opened his mouth and said he wanted to get in shape and take control of his finances with me, I was going to bind him to it.  

    Jared and I (who this article is not about) have actually been best friends since the fourth grade… We know that we’ve been through way more than just Under30CEO which has only been around for the last three years.  Sometimes it’s like a marriage, but we always know that we’re friends first, business partners second.  Plus we have an exit strategy, designed so we can both cleanly walk away and save our friendship…all this of course is can go wrong, but hopefully as friends we can always keep that mutual respect for one another.

    Thanks for reading–see you in NYC someday soon.

  • http://under30ceo.com MattWilsontv

    Thanks Maria, really glad you enjoyed.  It’s why I have three main groups of friends… my friends from home who I grew up with, my friends from college and my entrepreneur friends.  Everyone goes through these transitions, and there are value in the relationships with each of these different people.  It’s important to remember not to be a snob when it comes to making friends, there is a lot that you can learn from everyone.

    Happy holidays.

  • http://under30ceo.com MattWilsontv

    Hi Huntfour, think about these few things…
    Are your friends still getting into trouble and dragging you in? You know… partying, gambling, or committing crimes?  If it’s affecting you–distance yourself!

    But really, this article isn’t about cleaning house.  It’s about holding your friends to what they say they’ll do, having a basic code that you hold people that you trust to, keeping that mutual respect, and most of all–making new friends!

    The guy in this article is the man, he’s just not adding value in those two specific ares of my life, so I came up with alternative solutions by meeting new people.  When it comes to my social life, he’s still my right hand man and we have a blast when we hang out.  

    Just remember, the 5 people who you spend the most time with are the 5 people you are most like, so focus on that! 

  • Anonymous

    “I think what I need now is to surround myself with more people who have the same level of intensity and ambition to be and do something real and amazing.”
    I relate to this so much (which is why I love this article, am feeling super convicted right now, and will be probably thinking about it for weeks to come ESPECIALLY at my 9-to-5), and have been struggling with the issue since middle school.

    My problem is that it always ends up that people are waiting for me to make the best move or they say “I wish I could be like you” but they never want to join me. I would love to have a partner-in-crime or some archnemeses to get something real going and to be keep me accountable. Matt, any ideas on how to find and surround yourself with the right people?

  • http://under30ceo.com MattWilsontv

    I hear ya on the “I wish I could be like you” friends… we all have them.  If you are looking to find the friends who you look at and say “whoa, I wish I could be more like them” here are a few quick ideas…BTW these are beyond just “meeting” people b/c everyone should be able to figure that out, to me the real trick is the followup and making them become partner in crime status…

    Get good at texting–get peoples number and start texting.  It’s personal, you seem like your friends; email is generally annoying
    Throw parties–meet people, invite them all over and have them bring their coolest friends
    Invite them places–going to another event next week?  Invite 5 of your new friends and roll with an entourage… it creates an environment where it’s not just coffee or one on one time, your becoming that superconnector
    Start a mastermind–bring people together to actually solve problems.  Once a month get a bunch of cool people together and brainstorm on how to solve each other’s problems in your business
    Create shared experiences–don’t just sit around and talk business, go and do something…organize a ski trip or a camping trip or a weekend at the beach… it’s these types of things that really create bonds!!Also, check out this post I wrote this month http://under30ceo.com/how-to-create-an-amazing-network-of-people-around-the-globe/

    Hope that helps!

  • Anonymous

    It does. Greatly. Thank you. Will keep you updated…

  • Rajashekhar

    Good one, I too fired one of my bad company, because he told me that, “you never gonna make it happen” for that i told him “you are my fisrt and last problem for that to happen” said Goodbye!!!!

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  • http://twitter.com/gibsondm Alexandra Gibson

    Matt- way to go.  There’s enough of the world that’s going to try to get you down.  Good reminder that who we choose to surround ourselves with directly influence our own happiness and success.

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  • Yura Bryant

    It is often hard for people to take the personal out of a commitment that requires a lot of them. For this reason I barely include friends or family in my business endeavors because they do not understand it’s not personal it’s just business.


  • Arnold


  • Philip

    so true

  • Gill

    i can’t believe a respectable person could make something like this

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  • Glennus

    I like the idea of auditing friends in your life to see if, to a degree, they are adding value, but being friends with someone isn’t always about what they can do for you.  In that entire exchange I have to wonder what Matt was doing for his friend.  It was always about how someone can challenge him, how someone can motivate him, how someone can improve him.  If you’re the type of friend who throws someone under the bus because they’re having a bad month or because YOU can’t motivate THEM, then maybe it’s not them that has the problem.

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