An Open Letter to Frustrated Entrepreneurs (A Response)

by / ⠀Entrepreneurship Travel / May 22, 2013

Edison Failure
Last week Daniel DiPiazza wrote “An Open Letter to Frustrated 20 Somethings” on Under30CEO.  It blew up.  The article had over 100 comments on the first day.  Daniel’s premise:

If it was up to him, why would he make a “job” or “work” the center of his life?  When someone asks him “what he does”, why should he have to respond and narrowly define himself by the skills he uses to make money?

I’d spend my life traveling, learning languages, practicing martial arts, reading, programming, eating good food and (eventually) raising smart, open-eyed children. All the other shit can suck it.

Touché Daniel, and I agree: there is a better way.  Now let me break it down for those on a quest to “do what you love” from someone who’s been through all the ups and downs…

I graduated from Bryant University having built what the Collegiate Entrepreneurs’ Organization named the best chapter in the world, four out of five years.  I was leading a team of 150 smart, young, innovative, passionate people.  No way I was getting a f*cking job.

I pass up job offers galore, to “start my empire” from my mom’s basement outside of Poughkeepsie.  Pitching VC’s, writing business plans, sending money to India for web development, I was still, without a clue on how to actually make money from my lawnchair.  I call Jared O’Toole to drink some Miller Lite’s on the front porch and we realize there have to be lots of other young people trying to start businesses just like us.  We co-found

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Without a clue, and no revenue in sight, it’s now the dead of winter, and Poughkeepsie is getting depressing.  Then the Global Financial Crisis hits, and now we’re really screwed.  My mom comes to me shortly after Christmas to tell me that we will be losing our house.  The home I grew up in.

Lesson 1: At least be able to tell your mom how your business plans to make money.

Sh*t, those $65k+ salaries I turned down could be coming in handy right now.  It was time to hustle.  I accept the first job I can find on Craigslist–a position for a driver and show up at 6AM… wheeling and dealing can’t be so bad.  It’ll be my mobile office…

Wrong.  I show up and am given the keys to a dump truck.  With an 18 foot trailer.  WTF.  I guess it’s time to learn to drive a dump truck…

I get us to the job site, and I’m quickly informed that the crew of Mexican laborers I’m driving around aren’t going to appreciate it if I sit in the truck… It’s time for me to dig ditches 12 hours a day for the next six months…

Lesson 2: When you put your back against the wall, you make sh*t happen.

Sure, I could have chalked up my entrepreneurial dreams and got a cushy desk job.  But instead, I put myself in the most uncomfortable situation possible.  Digging ditches with guys who could work me under the table, AND THEN going home to moonlight Under30CEO until 2AM was absolutely miserable.  I was making $15/hour, living in a tiny apartment with my mom.  I love you Mom, but that’s not exactly what I thought my “empire” would entail.

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Shout out to Jared O’Toole who represented Andersen Windows at the Wappingers Town Fair that year.

Lesson 3:  Test everything.

We’ve tried everything on this damn site.  We don’t talk about it much, but Under30CEO was once just a Ustream show, then a Ning Network, a Meetup, and a membership site, we’ve offered daily deals, affiliate offers, consulted startups, hosted workshops on social media, done dealflow for VCs, you name it, we’ve tested it.  It’s been the smartest thing we’ve ever done.  Make little tests, if they make money, run with them, if not, see ya later…

Lesson 4: You don’t test stuff very long when you’re broke.

While throwing stuff against the wall and seeing what sticks is great, when you’re bootstrapping on a ditch-digger’s wage, you don’t have the money or the patience to test things for very long.  You’re trying to get cashflow positive as fast as possible.  Any of the business models listed above are solid ideas and could be turned into million dollar businesses.  Looking back at it, it was probably our biggest curse.  We were looking to get hit the jackpot, and we were quick to give up.  Young and impatient?  Yes… But smart.  Here’s why:

Lesson 5: Never do anything you are going to hate.

Call me a pretentious, formerly-frustrated 20-something, but we stuck to our core value of doing something we loved.  We love being in the business of inspiring young entrepreneurs.  Many of those other business models were not that, and we knew we would eventually grow to hate them.  We listened to our gut, and as corny as it sounds, we followed our dream…

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But don’t think for a moment that it was easy.  

Guts, grit, determination, yeah, all of that, and then some.  It’s way harder than anyone will ever tell you.  But worth it?  Oh, hell yes.

Now we’re officially spinning off a new company, based on something we’re even more insanely passionate and excited about… A travel company for ambitious young professionals.  The best part?  I got to spend seven months around the world, working from this very laptop, plotting world domination.

No wait, ACTUALLY, the best part is that this travel company is designed to be the launching pad for young people who want to see the world, and go out and do big things.  This isn’t a course and there is no curriculum.  We simply curate experiences in places like Costa Rica and Nicaragua with other amazing people and inspire the creative environment to let you guys figure out your next big moves.

An Open Letter to Frustrated 20-Somethings?  Yes Daniel, you’re spot on.  It is possible to make money doing what you love.  And when it helps other people figure out their dreams?  It’s game on.

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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