Nobody Likes You When You Break The Rules : Under30CEO Nobody Likes You When You Break The Rules : Under30CEO
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Nobody Likes You When You Break The Rules

| January 10, 2013 | 24 Comments

Costa Rica Surfing

“You need to figure out how to close up shop Matt…”
“It’s about time you moved on and worked for someone else…”
“That site actually pays your bills?”

Quotes from my motivation board.  At an Under30CEO event, Alexis Ohanian, Co-Founder of Reddit told us to make a negative reinforcement board with all the things anyone has ever said bad about ourselves… as motivational as it is, sometimes that sh*t gets to you.

When you are bootstrapping nobody takes you seriously.

Everybody thinks I’m a f*cking hippie.

I’ve lived in Breckenridge, Colorado at the base of the gondola, and I just signed my lease on a condo in Tamarindo, Costa Rica, a 2 minute walk from one of the most famous surf spots in the world.

But seriously, Under30Media is a real business, and yes, to my friends from high school, I do have a real job.

Actually… this article should be called:

Nobody Likes You When You’re Awesome.

Our business actually has positive cashflow, pays us full-time salaries, and the real gem is that it allows us to live anywhere in the world.  BTW, to my friends and family who think I’m out here “finding myself”, I know what I’m doing with my life, I’m 27, and I’ve known I wanted to be an entrepreneur since I was 4.  We’ve built a business that we think is awesome, and I couldn’t be happier.  Nobody can ever take that away from us.  Coming soon on Under30CEO: I’m Not Finding Myself, Bro.

Even during the first draft of this article, my Co-founder @JaredOToole said, “Advertisers are not going to take us seriously if they think we’re surfing half the day.”  Coming soon on Under30CEO: Lifestyle Businesses: Why We Should Ban This Term and Why You’re Totally Wrong.

We could raise money for our business if we wanted to.  Under30Media is the real deal.  We have proof of concept in our business model with our first site Under30CEO, and now we’re rolling out sites with bigger markets, and greater monetization opportunities like Under30Careers and Under30Finance.

Why Shouldn’t You Raise Venture Capital?

Venture Capitalists are looking for a exits of over 8 figures, in 5-7 years.  Founder’s equity will be diluted, your investor will be involved in the decision making of your company, and you’ll be spending a ton of money, hiring a bunch of people, probably without proof that your business model works (if you have one).

I’m Not Down With That

Well, guess what.  Neither were Mike Arrington of Techcrunch ($40M sale to AOL), Pete Cashmore of Mashable (valuation estimated between $40M and $200M) and Nick Denton of Gawker (valuation estimated around $100M).  They bootstrapped their content businesses themselves and did it the hard way.

Even Lerer Ventures, investors in Huffington Post and Thrillist content businesses told me they weren’t interested in investing, but we could still make a “shitload of cash doing it”.

“But It’s Not Big Enough”

Under30Media is only a 6 figure business right now.  I know we have the potential to work on a hardcore consumer web startup that will scale much faster.  But is it worth my happiness?

Hm, let me think… working from paradise, doing something that makes impact, and on the weekends surfing, learning Spanish, and exploring a new part of the world… I think I’ve made my decision.

Dear VC Backed Founders: You Have a Boss

Let’s break it down to it’s simplest form.  Why did we start a business?  So we could live life on our own terms.

When you are backed by serious investors, you are on a tight leash.  Don’t think that you are going off to Central America for the winter.  READ: I’M NOT ON VACATION, I’M WORKING.  If your VC doesn’t like you, they will try to replace you and your team.  By the way, if you have to answer to someone, guess what, you have a boss.  Think CEO’s of publically traded companies like investor relations calls?

Be The Best in the World

I’m a firm believer that if you are going to do something, you should do it 100%.  So take this to the extreme and ask yourself right now: “What can I be best in the world at?”

Do that.

If you really need money to execute your business model, then raise it.

The Plan

There are two main ways Under30Media can make money in the content business.  Advertising and events.  If we create the best content in the world for young entrepreneurs and create the best events possible, our business will be a success.

Yes, we’ve rolled out new sites: Under30Careers and Under30Finance.

Yes, we’re running amazing experiences in exotic places in the world like our Microfinance Surf Camp to Nicaragua.

And yes, we’re planning on being best in the world.  Why not right?

Live Different

Just because “the cools kids” are doing it, doesn’t mean your life has to be a scene out of reality television’s Bravo: Silicon Valley.  Wow, entrepreneurship has really lost it’s flair.  It used to be about going against the grain, innovating, and doing something that nobody ever thought possible.  Now, everyone just follows the crowd, sells some angel investor the dream, drives up valuations… oh, and then tries figure out their business model.

I really hope this bubble bursts.

I hope this article gives you some things to think about as you are designing your own entrepreneurial journey called life.  The world of entrepreneurship needs more leaders and less followers.  The world needs people who can think for themselves.

Life is more fun when you break the rules.

If you are truly interested in living different, please join us in Nicaragua on our Microfinance Surf Camp April 17-21 or on our Startup Iceland Adventure this spring.  Our events are designed to inspire you, get you to think differently, and when all is said and done, you’ll be part of a lifelong community that can say you lived life your way.

Life is all about the experience.

Matt Wilson is the Co-founder of Under30Media.  Travel with him to Nicaragua this April for Under30Experiences: Microfinance Surf Camp.

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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Awesome People + Awesome Places
Travel around the world while making new friends

Under30Experiences curates awesome experiences around the world for young travelers.

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Category: Startup Advice

  • Fernando Guzmán Cárdenas

    What will happen when you are 30+?
    Because “Over30CEO” is much more like: “LikeAnyOtherCEO”

  • MattWilsontv

    Hey Fernando, thanks for the question– I probably have heard this more times than any other question in my life… the simple answer is that Under30Media will always have a target market, even when we’re dead and gone… luckily for us, people will always age into our demographic.

    We also like to simply say Under30Media is about attitude, not age. Or my personal favorite, that @JaredOToole coined, is that hopefully we’ll be smoking cigars and drinking scotch by the time that happens…

    In all seriousness, we are recruiting young talent for our team, so if you know anyone who wants to carry the torch and be part of something awesome, please let us know! matt (at) Thanks Fernando.

  • Luan

    I am over 30 (just) but you keep inspiring me! I lived according to the rules for too long and am doing things differently now. Never been so happy before.

  • MattWilsontv

    Hey Luan, I think what you’ve done in Nicaragua as a Kiva Fellow is really awesome. I’m really happy we had a chance to meet and surf together. Surrounding myself with people like yourself is what inspires me…

    I’ll be in touch soon, lots to update you on about the trip in April. Thanks for reading!

  • Larry B

    I’m over 40 and still enjoy reading your articles. I forward them to ALL my under 30 salespeople and managers. Keep up the good work !

  • MattWilsontv

    Thanks Larry, really appreciate you being part of the community. You’re always welcome! Thanks for dropping a comment–makes writing even more fulfilling.

  • tory Ansuwan

    Thank you for posting this. I hear all of these quotes daily and sometimes I wonder if I’m in over my head. But then I hear about others being told the same things and it makes me feel like I might actually be on the right track. I may not respond very often…but when I do, it means it’s really had an impact.

  • MattWilsontv

    Hey Tory, I really appreciate you responding, and I’m glad to hear that these words have resonated with you. The books we read and the quotes we hear have been written and said because someone figured out how to be successful and they’ve shared their lessons. While there is no magic formula, I hope you keep trying, and go against the grain when you can… It’s all we can do. Best of luck.

  • Tory Ansuwan

    P.S. I lived in Thailand for over 3 years (and now make occasional trips back) and commend you for living the life you want. I printed your article and posted it on my mirror. You are a true inspiration Matt.

  • MattWilsontv

    Hey Tory, really honored to hear. Keep breaking the rules. Looking forward to you dropping some comments and keeping me in the loop on how you are doing. Thanks!

  • Lisa Lotte

    Hej Matt, thanks a lot for this inspiring article! In these days I seldomly read something provocative and in my entrepreneurship studies at university I am missing more people like you seem to be. How can I stay informed about the Startup Iceland Adventure? The link did not really work and I could not submit my email. Cheers, Lisa

  • nayda

    Omg, thank you for writing this, that’s exactly what I needed to read today. Would like to see more info about the event in nicaragua: programm, pricee, and so on

  • MattWilsontv

    Hey Lisa, glad you liked the article. I wish I had more time to come lecture in the States. I really enjoy doing it. Check out The last page should let you submit. If it’s not working PLEASE let me know matt at :) Thanks!

  • Cheryl W.

    I think I love you. I have never in my life heard someone sum up true entrepreneurship so poignantly. The VC “this is cool lets build now and figure out if we can make money later” crowd are so en vogue right now, but they are founders. Entrepreneurs are a different breed. Thank you, Matt.

  • Lisa Lotte

    Hej Matt, thanks for your reply. Now the link works and I could submit my email. Best wishes from Sweden! :)

  • Sushrut Munje

    Thumbs up :)

  • MattWilsontv

    Hi Cheryl, haha, this ranks up there as one of the best comments I’ve ever received. I hope people get back to growing real businesses, instead of just cool music and photo sharing apps. What the world needs is smart people solving really tough problems… not more angry birds!

  • MattWilsontv

    Hi Nayda, glad you enjoyed. Please check out and scroll the last page. Join the list, and make sure your emails don’t go to spam. You should get a little more info today! Hope to see you in Nica.

  • MattWilsontv

    Hey Lisa, awesome. Would be great to have you in ISK from another Nordic country. It’s awesome up there. Cheers!

  • Maria Joyner

    As I am commenting on this, Money came on Songza. Awesome.
    So this is awesome. Totally dig how you are leading by example. Entrepreneurship is not all about taking VC money and building a company that exits in 5 years. It’s a hell of a lot easier to build a fast growth company that exits than to keep a company innovative and relevant for 10, 20, 50 years. The great entrepreneurs in American history built dynasties that impacted how the country was founded. The American Dream wasn’t about getting a job and working so you could eventually retire and “be happy”. It was about building something that made a difference and allowed you to live the dream.
    Matt, you are doing so much more than simply saying “Stop Doing Shit You Hate”… you are showing people it can be done, successfully, enjoyable, and at a young age. Your journey the past year has inspired me to DO instead of SAY. To let actions tell the story. See you in Costa Rica!

  • Pingback: Why I Hate Term “Lifestyle Business” & Why It Should Die

  • Melissa Krivachek

    I love the sincerity and obvious (or not so obvious in some people’s eyes) adventures of being a real entrepreneur. It’s not about the money although don’t get me wrong it’s great, it’s about the people, the experiences, the opportunities, and most importantly the impact. I’d rather be bootstrapping it then bootlegging it ;) Matt, you Jared, & Cara do a phenomenal job of creating an amazing experience and content for the reader. I have to mention I had someone read one of my articles on this site & tell me about how it wasn’t their style. My response to that was I have nothing to prove to you because what I accomplish in my life will not compare to what you have accomplished in the already 58 years you’ve been alive. Which just goes to show “Nobody likes it when you’re awesome!”

  • Danny-J

    Love it!! haha I have an online business too… friends and family think I do nothing.. you get paid to do that? yup! and I can travel whenever/wherever.. keep it up guys!

  • Julie Dawn Harris

    Inspiring! ‘The world needs more leaders, than followers’. Great thoughts Matt. I have never read as motivating as this blog. :)