An Open Letter to Frustrated Entrepreneurs (A Response) : Under30CEO An Open Letter to Frustrated Entrepreneurs (A Response) : Under30CEO
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An Open Letter to Frustrated Entrepreneurs (A Response)

| May 22, 2013 | 45 Comments

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

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.

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…

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.

Break out of your comfort zone: Enter to win a Trip of a Lifetime to Costa Rica via Under30Experiences.

Matt Wilson is Co-founder of Under30Media and Adventurer in Residence at Under30Experiences.  

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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Under30Experiences curates awesome experiences around the world for young travelers.

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Category: Entrepreneurship, Travel

  • brent

    great article, thanks for sharing

  • MattWilsontv

    Hey Brent, thank you– hope you enjoyed the story and are out there making it happen yourself.

  • Liz Dean

    Sounds like you all are moving in the direction of the “Summit Series”. They recently bought out Powder Mountain and will eventually take over Eden, UT (unfortunately). Congrats.

  • Rich Peck

    Thanks for the inspiration buddy! You never did tell when the “tipping point” came though. When did you know the time was right to move forward?

  • MattWilsontv

    Hey Liz– I’ve been to Summit Series, and really admire how the guys have brought amazing young thought leaders together year after year.

    Under30Experiences is focused on curating boutique experiences, internationally, 30 people at a time, and becoming a real travel company for young professionals.

    We don’t see ourselves as a competitor to Summit, as their events are normally large domestic conferences, but if that means one day we buy a mountain, or an island, or something cool– we’ll certainly take the comparison :) Thanks for reading.

  • Harry Alford3

    Great article. Thanks!

  • Lizbeth Cardozo

    Ha! I love how authentic and honest you were in this article. Thanks for sharing, Matt. :)

  • MattWilsontv

    Hey Rich– there were a few different tipping points along the way… We hustled to get Under30CEO’s readerbase pretty big, and people started hiring us to teach them how to grow the followings for their startup. That allowed us to move out from our parents, quit digging ditches, etc. We soon realized that consulting isn’t very scalable because you are trading time for money, and you’re building someone else’s dream instead of your own…

    We eventually hustled hard enough where the advertising, custom content, events, and clients that we have for Under30CEO paid us enough where we could stop trading time for money, and focus on scaling a non-service based business model.

    If you’re looking for a true “tipping point” there isn’t any HUGE “ah-ha” moment, but this article that was written in Entrepreneur Magazine, drove us huge exposure, thousands upon thousands of readers who stayed on the site for hours, and new clients:

    A word of warning though, don’t look for that one big PR break that is going to get you there– no article written about us since then has ever impacted us like that one did. Making a quality product is what we really credit the success to.

  • MattWilsontv

    Hey Lizbeth, thanks for noticing. Under30CEO and now Under30Experiences is all about creating communities of open / transparent people who want to help each other get to the next level. I couldn’t think of anything I’d rather be doing.

  • MattWilsontv

    Thanks Harry, glad you enjoyed. Keep hustling!

  • Muts

    Can’t wait for this travel idea to become a reality!

  • MattWilsontv

    Hey Muts– it’s a reality my friend. We’ve run four trips already, but now it’s time to make it a separate business from Under30CEO and are going to be running a trip each month this winter. Check it out– we’re giving a way a free trip to Costa Rica also. Glad to hear you are excited.

  • Daniel DiPiazza

    Matt, I love this. And guess what? It’s all BECAUSE of people like Jared and yourself that I had the courage to step out on my own and actually make the difficult, difficult leap. You’re no stranger to adversity (ditch digging..really??!!)…but I don’t think many people realize how hard it is in the beginning phase. If you can get through that, though you’re opening yourself up to a world most people don’t even know exists. There’s a game being played all around us, and if you’re smart, you can tap into it and be free.

    Thanks for the support and the inspirational post. Can’t wait to contribute more, my friend.

  • Daniel DiPiazza

    Yeah. I’m going to be at one of those.

  • Daniel DiPiazza

    Agreed. Really good stuff.

  • Shaq Abid

    No pain no gain!

  • MattWilsontv

    you know it Shaq.

  • MattWilsontv

    Hey Daniel– really appreciate people like yourself writing in from all over the world to tell us what you’re going through trying to make it. We get such a huge benefit surrounding ourselves with people like yourself, you have no idea. We’re just the facilitators– 99% of the content Under30Media is produced by you guys.

    Posts like yours inspire us to keep on doing what we’re doing. Thanks again my man. See you abroad.

  • Jay Weinberg

    Great article, Matt and congrats on the new company! Let me know if you need any “adult supervision” on any of your trips! Keep up the great work. You make the entire Bryant University community proud.

  • Patrick Sargent

    Congrats on all the success Matt. I remember when you and Jared were just getting this up and running as a Ustream show. You’ve come a long way! Keep up all the good work! Hopefully I’ll see you on one of your trips in the near future.

  • cesar romero

    sometimes we all get overwhelmed by things and events that happen in our own lives and we seem to think that there’s no way out and that we are doomed but it is real-life stories, like the one you just wrote, about how you have worked hard and overcome obstacles throughout your journey that really inspires me and reassures that it is all about resourcefulness. Thinking about what you do have and how you can work with it to get to where you want to be. Your story is inspiring, and I know we talked about it but not like this. You really put yourself out there in this post and the best part is that is an honest story with the sole purpose to inspire and educate our audience to take action and do whatever it takes to be successful. Cheers Mateo and always wishing you awesomeness.

  • MattWilsontv

    Pat, awesome to hear from you. Hilarious actually– our Community Manager @twitter-377774048:disqus just dug up your interview with me circa 2008. Good stuff, haha.

    Thanks for the support, and let me know if there is anything I can ever do to help!

  • MattWilsontv

    Hey Jay– haha thanks for the support. Will certainly let you know. Love the Bryant alumni chiming in on this article!

  • MattWilsontv

    Thanks Cesar– you’re the man, was really awesome to meet you in Nicaragua, and glad you are now officially part of the team. Keep doing what you’re doing– like the name of your blog says, you are writing “Cesar’s Journey”!!

  • Amber J. Adams

    Matt, I’m so glad you wrote this. There is so much value in showing the behind the scenes of Entrepreneurship. I never dug a ditch, but I did telemarketing for State Farm. At least you got some bangin’ arms out of the deal.

  • MattWilsontv

    Hey Amber– hahaha– digging ditches has it’s benefits I guess. Thanks for reading– happy to share the behind the scenes story.

  • Cara Murphy

    Daniel, you have to! It’s a truly incredible experience!

  • Cara Murphy

    Matt, this is both inspiring and challenging- it makes me realize that hard work does pay off, but you will have to persevere and earn really it! My family and most of my friends think that I’m crazy for working so much, but this validates my dedication and desire to be productive. I can’t help but be energized by people making a difference and building communities that will change the world. Can’t wait to see where you and Jared go next!

  • Bell Summers

    Well, who else succeed that have never experienced failure first? It’s part of the start up process. You get to encounter problems and eventually learn how to solve them. That’s where success happens when we are already molded by rejection, failure and frustration. Quite a positive mindset Matt. Thanks for sharing this. :)

  • MattWilsontv

    Hey Bell, thanks for the positive feedback– it rejection, failure, and frustration are all part of the journey… not necessarily my favorite part, but the stuff that motivates me the most.

  • MattWilsontv

    Thanks Cara–seeing how hard you work, and how focused you are is an inspiration to all of us. We’re building a platform that everyone in the Under30Media ecosystem can use for their personal and professional growth– and that includes our Editorial team. Your hard work is very much appreciated. Nobody can ever take away that drive. Thanks again.

  • Belinda Summers

    Same thing with me. It motivates me well to try harder and try new strategies. :)

  • Andres Robelo

    Matt, this is incredible. Stories like these have to spread like wildfire they are an inspiration for the world. Congratulations on your new venture. You now have family and friends in Nicaragua. I would like to add and emphasize the positive impact trips like these bring to the local community in the countries you are visiting. I invite you to please share your story when you are in Nicaragua this will only inspire others to follow and see the possibilities that are beyond what we imagine. I have no doubt that slowly we can bring prosperity and development one trip at time, one story at a time encouraging and facilitating an entrepreneurial driven society.

  • Martin P.

    Matt, want an extra “Gold Nugget?” If you really want to succeed in any home based business, career or job you need to get plugged-in with Dani Johnson ( She’s a Success Coach/Motivational Speaker among many other things and loves to help frustrated entrepreneurs succeed in their businesses whatever it may be. She’s really good. Check her out.

  • MattWilsontv

    Hey Andres, great to hear from you. Really happy to hear about the positive impact we’re making. It’s awesome to hear from local entrepreneurs, and share stories from unique places like Nicaragua. You guys really have an interesting perspective and insights on business, it was a pleasure to meet with you all at the US Embassy. Let’s keep in touch– we’re running a December and February trip back to Nicaragua with Under30Experiences.

  • Apeyros

    Very inspiring words. Keep up the good work guys!

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  • Rich Peck

    Thanks for the comprehensive reply!!!

    I guess you could sum it up with the term “momentum”, which is to say that you’re going to have several major goals along the way (1: get something going; 2: invest energy to grow it; 3: keep moving momentum forward)

    Thanks for the great updates!

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  • aklam

    Sounds amazing. Good on you guys!

  • Finance and Me

    Hello guys, I know this might be a bit off-topic, but I am from and organization called Child and Youth Finance International and our aim is to provide access to financial services and financial education to youth around the world. We have now developed a survey for people under the age of 25 in order to help us achieve our aim. If anyone would be willing to fill it out (if it applies to you), or take it to someone who could, it would be of great help. I leave you the links to our website and the survey. Thank you very much.


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