Bootstrapping to $5 Million: Under30Experiences CEO Matt Wilson (Part 4)

Sramana Mitra: How has you blog content strategy changed as you morphed from writing about entrepreneurship to travel?

Matt Wilson: We ended up selling Under30CEO.com. We then decided to completely break off into a new content strategy and into a completely separate business. It was time for us to move on. I was running Under30Experiences and Jared O’Toole, my partner, was running Under30CEO.

We had to make a decision. Do we want to have two smaller companies or do we want to do one thing really well? We were able to sell one company and invest the money into the second company. We struggled for a long time, we were just two guys who were running a website and living at home with their parents. Luckily, our website has lots of things to buy now.

Sramana Mitra: If you’re good with content and if you can use content marketing to market something that you’re actually 

selling on your website, you can do wonders with it. Without that, the website in itself just with content doesn’t make money.

Matt Wilson: Yes and to fully answer your question, our content strategy has shifted over the years from just being about blog, Twitter, and Facebook. That was where things were in 2008 through 2012 when we were working on Under30CEO. Now, most experiences with content don’t start on your web browser. They start in apps. It may be Facebook. It’s probably Instagram. It may be Snapchat. It is, at times, YouTube.

We do have our blog as well, because it’s very powerful for search engine optimization. People are searching for things to do in these countries, like itineraries and places to visit. We want to rank highly for these things. Our content strategy has changed over the years mainly to get the people who have been on our trips to spread the word about us and to use our hashtags.

It’s the coolest thing that people are going to do all year. They’re once-in-a-lifetime trips. We do them very well. When they go home for Thanksgiving, they’re going to tell all of their friends. They’re going to show off their pictures. Pictures and videos have come a long way since we were just writing blog content. The places sell themselves. When you see them, people want to go there.

Sramana Mitra: Very good. How far along are you? How are you doing revenue-wise?

Matt Wilson: We’ve just hit $5 million in revenue for the year. We’re looking to grow to $8 million or $10 million in 2019. We’ll have a real good idea of how well we will do that by the end of this week. I don’t know when this is going to be published, but we’re speaking right before Thanksgiving. Black Friday is the biggest day of the year for travel sales. We put on a huge sale. These are all for 2019 sales.

Sramana Mitra: Terrific. I love to travel. I put in enormous amount of energy into planning our trips. I completely understand that most people don’t have the energy or interest to work out the details. We are headed for two weeks of travelling around Andalusia. It’s an incredibly complicated trip to plan. We are going to 14 different places. Detailing out every single place and every experience is an incredible amount of work.

Matt Wilson: I’ve not been there.

Sramana Mitra: It’s a wonderful trip. I did it in 1995. It was beautiful. This time, we’re doing a more comprehensive trip. It turns out that I will be seeing places that I’ve not seen on that first trip. I was a much less experienced traveler in 1995 than I am today.

Matt Wilson: Excellent.

Sramana Mitra: It was very nice talking to you.

This segment is part 4 in the series : Bootstrapping to $5 Million: Under30Experiences CEO Matt Wilson
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