Nobody Likes You When You Break The Rules

by / ⠀Startup Advice / January 10, 2013

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.

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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?

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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.

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Life is more fun when you break the rules.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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