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From Digging Ditches to Advising Young Entrepreneurs

The 24-year-old founder of Under30CEO.com on creating an online resource for budding business owners.

Name: Matt Wilson, 24
Founded: Under30CEO.com, 2008
Business: Website offering young entrepreneurs the tools and resources to succeed.
Location: New York City

Matt Wilson
Matt Wilson, co-founder of Under30CEO.com

As an ambitious young hopeful, Matt Wilson started to act on his entrepreneurial aspirations while many were still figuring out what to major in at college. As a business management student at Bryant University in Smithfield, R.I., Wilson founded the Collegiate Entrepreneur’s Organization, a network of fellow college students who shared his disdain for working for a monolithic, corporate company. Growing to about 150 students, the group hosted networking events, workshops, an elevator pitch competition and a CEO speaker's series with keynotes from powerhouses like media mogul Ted Turner and JetBlue founder David Neeleman. (Bryant University has since made the pitching competition a requirement for all freshmen entering the program.)

After graduating in 2008, however, Wilson’s life changed dramatically. He moved back home to East Fishkill, N.Y., with his mother, who was struggling to maintain her real estate business during the height of the economic recession. Wilson was even forced to accept a job digging ditches to help pay the bills. There wasn’t much time, or energy, to develop his own venture.

Then, after a conversation with a childhood friend, Jared O'Toole, the pair decided to partner in rebuilding the entrepreneur network Wilson created in college. Under30CEO.com was born, starting as a social network for entrepreneurs and evolving into a content-rich site. Wilson and O'Toole draw on their own experiences to provide educational resources, as well as mentor, other young entrepreneurs. Based on a subscription, advertising and consulting services revenue model, Wilson says the site attracts roughly 150,000 page views and 75,000 unique visitors per month.

Launching Under30CEO.com didn’t come without its own obstacles. Here, Wilson shares his top three startup challenges and how he overcame them.

Challenge No. 1: Make ends meet.
When my mother told me we were losing our home -- the home I grew up in -- I knew I needed to start bringing in some income, and fast.

Solution: We sold everything and moved into a small apartment. I searched for a job online and accepted a position driving an 18-foot trailer for a commercial landscaping crew. I later found out that I’d also be a member of the ditch-digging crew. Being the youngest and least experienced among them, I started at the bottom, which meant I was doing a lot of digging.

After digging ditches 12 hours a day, at night I’d work on launching Under30CEO.com. My strategy was to stay up all night, every night, until the website brought in enough revenue for me to quit the landscaping job. I beat myself up mentally, physically and emotionally for about six months until Under30CEO began to take off with subscriptions and consulting clients. This was simultaneously the most miserable and gratifying time of my life.

Challenge No. 2: Build a professional website with no programming experience.
My partner and I had no coding or website development experience and we were broke. We tried unsuccessfully to find another partner who was willing to work for equity.

Solution: We started out with a site that was self-hosted on Wordpress, which is widely considered flexible and easy to use. For customization, we turned to online marketplace Elance.com where freelancers can bid on projects. We outsourced the web design overseas for $175. However, we ended up going in circles with the developer who didn't really speak or understand English. We eventually found a friend who was desperate enough to make the website changes in exchange for beers and a lifetime of client referrals.

Challenge No. 3: Balance work and life.
Living in a small apartment with your mom in a boring suburb, digging holes in the dead of winter and getting minimal sleep can make a person go crazy.

Solution: First, my business partner and I had been friends since grade school. We kept each other grounded and sane. Secondly, part of the goal with launching Under30CEO was to reconnect and rebuild my network, while providing would-be entrepreneurs the tools for success. Once the site was live, I inherently became more connected, virtually at least, by people with similar goals and challenges. It was inspiring. Ultimately, achieving work/life balance was the reason I went into business for myself. I decided to live like others won't for a few years so that I could live like others couldn't for the rest of my life.

The Young Entrepreneur Council is an advocacy group dedicated to fighting youth unemployment and underemployment by helping young people build successful businesses and offering alternatives to traditional career paths. Its members include successful young entrepreneurs, business owners and thought leaders. It was founded in New York in 2010 by serial entrepreneur Scott Gerber, author of the forthcoming book, Never Get a 'Real' Job.

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