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Bootstrapping to $5 Million: Under30Experiences CEO Matt Wilson (Part 2)

Posted on Tuesday, Dec 11th 2018

Sramana Mitra: What did you do when you came out of college? Did you start a company right away?

Matt Wilson: I had a few job offers, but I was just not interested in going in that direction. It just didn’t sound appealing to have to show up somewhere from nine to five just to answer to someone and work to make someone else’s dreams come true when I could make my own dreams come true. I moved back home to this small town I talked about.

With the emergence of Twitter, Facebook, and blogging, we could be surrounded by smart, young, and innovative people online. We started a website called It has been acquired twice since we started it. We started a media site for entrepreneurs. We had meetings with people from publications that had been around for years, like Inc. magazine, who said, “To be honest, we’re scared that a couple of kids from upstate New York can start a website, and it can have just about as much traffic as”

We knew we were on the right track with something there. As you probably know, it becomes very difficult to monetize media sites even if they are getting half a million monthly views. We wanted to continue to deliver value in something more high priced that people would pay for. We started setting up seminars and workshops, which was then how we started Under30Experiences, our travel company.

Sramana Mitra: What were you selling?

Matt Wilson: For Under30CEO, we sold advertising. We had different membership and mentorship programs. Once we decided to go on a retreat with our blog readers. That’s when things changed for us. I went on a trip solo to Iceland because I was getting burnt out after spending 14 to 16 hours a day in front of my computer. It’s hard to build a website that gets that much traffic.

I took off on a random trip to Iceland and I just had one of these epiphanies. I was on top of this volcano that erupted in 2010 and stopped all the air traffic between North America and Europe. It’s 11 PM and I’m sitting there on top of this glacier watching the sunset after a day of full of outdoor activities.

I thought, “What am I doing with my life? Why am I sitting in front of a computer the whole time?” I observed my friends and realized that a lot of them were starting to run themselves into the ground at just 25. I wanted to do something that aligned a little bit more with my values. That’s when I thought of putting a trip together for our blog readers. It turned out that people did want to get away from their desks. People did want to meet other young people who were in business.

We took that first trip. It was an extreme success, meaning that everybody had a great time. Some of my best friends today are from that very first Under30Experiences trip. The main feedback that we got was, “We didn’t need any business program or mentorship. We just want to go and have fun. Let’s go away together and see what happens.” We took that mentality. We ran a couple more.

Other people started asking, “Do we have to be CEO’s? Do we have to be entrepreneurs?” After that, we realized that we were onto something much bigger than just the little market of entrepreneurs. We started running regular adventure trips for young people. Under30Experiences has grown and we’ve run about 250 of these group trips this year.

This segment is part 2 in the series : Bootstrapping to $5 Million: Under30Experiences CEO Matt Wilson
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