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Best of Bootstrapping: How Under30Experiences Bootstrapped to $5 Million

Posted on Friday, Apr 5th 2019

Under30Experiences CEO Matt Wilson has built a fan business using content marketing to sell travel experiences to a millennial demographic. Very cool!

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where did you grow up and in what kind of background?

Matt Wilson: I grew up in upstate New York. I grew up in a little tiny town called Stormville, New York. It’s about 60 minutes outside of New York City. It’s not really that close to the city, but it wasn’t extremely rural. I just started being an enterprising young man whether it was by mowing lawns or picking golf balls out of the local ponds. Selling the golf balls on eBay was my first online business. That really ignited the passion for entrepreneurship. Baseball cards would probably be the other thing that I was really passionate about when I was younger.

Sramana Mitra: How did that lead to where we are today?

Matt Wilson: I went to business school. I sold my landscaping business before I went to college. I went to Bryant University. I realized when I got there that there weren’t a lot of resources for entrepreneurs because the school was very focused on corporate finance and accounting. Startup communities hadn’t really taken off. There weren’t a lot of resources online at that time, so I started asking around.

Why aren’t there any classes on entrepreneurship? What if I don’t want to wear a suit for the rest of my life? Jack Welch came and spoke, and I got up and said, “You have touched on entrepreneurship three or four times in your presentation. What do you think of Bryant University having a major or minor in entrepreneurship?” The response that I got was you should have gone to Babson.

As an entrepreneur and an innovator and as someone who doesn’t take no for an answer, we started the Collegiate Entrepreneurs Organization on campus and ended up establishing the degree. We won a lot of national awards through the Collegiate Entrepreneurs Organization. We brought in many other famous speakers. We were able to change the culture of the university in a way that was so profound that people, all of a sudden, showed a lot of interest in entrepreneurship.

As investment banking has gone out of style a little bit, entrepreneurship and startups have really taken over as the way that young people can make something of themselves. In five years’ time, we went from absolutely no major and minor in entrepreneurship to having the number one major in the entire university. It was pretty cool to see an institution completely change its culture. It was really fun.

Sramana Mitra: Just a little detail, where is Bryant University geographically?

Matt Wilson: Rhode Island.

Sramana Mitra: What time period are we talking?

Matt Wilson: This was between 2004 and 2008. That’s when I graduated, during the economic downturn.

Our conversation continues here.


This segment is a part in the series : Best of Bootstrapping

. Bootstrapping to an Exit
. Why is Bootstrapping Important?
. How Can You Play this Low-Probability Game Intelligently?
. Do NOT Go to VCs as Beggars - Go as Kings
. Excess is NOT Required for Success
. Bootstrap First and Raise Money Later
. Some Bootstrapping to Exit Case Studies
. The Buy Side of Bootstrapping to an Exit
. Blitzscaling vs. Bootstrapping
. Bootstrapping to Unicorns
. Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million
. Mailchimp Bootstraps to $600M Revenue
. Bootstrapping from Arizona to $10 Million
. Bootstrapped Basecamp Executes a No Nonsense Strategy
. How Under30Experiences Bootstrapped to $5 Million
. Bootstrapping with a Paycheck
. How CEO Amjad Hussain Bootstrapped using Services from Michigan
. Seed Investors Who Like Bootstrapped Businesses
. How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million
. Bootstrapping with Services
. How The Intern Group CEO David Lloyd Bootstrapped to $13 Million
. How Passageways CEO Paroon Chadha Bootstrapped from Indiana
. How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million
. Death by Overfunding
. How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+
. How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck
. TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage
. The VC-Entrepreneur Compensation Disbalance
. BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering
. Tremend CEO Marius Hanganu Bootstraps from Romania
. Gesture CEO Jim Alvarez Bootstraps to $10 Million
. SproutLoud CEO Bootstraps to $30 Million from Florida
. Tuft & Needle CEO Bootstraps to Over $100 Million
. Co-founders Bootstrap Linguamatics to Over $10M from the UK

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