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Many teens get a job in high school, but most don’t actually start their own business. When a knee injury left Winston Pillsbury with a lot more time on his hands, that’s exactly what he did.

In September 2023, Pillsbury was injured in a soccer game when Vail Mountain School was in the playoffs. He tore his anterior cruciate ligament and had knee surgery in October and had many months of recovery ahead of him.

“So, basketball and lacrosse were out, and so was skiing and that was really tough on me because my whole life up to that moment was sports. Sports were a huge part of my identity and then all at once, that was taken away from me,” Pillsbury said.

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Pillsbury decided to get a job to fill some hours after school. He worked at Vista Bahn ߣÏÈÉú Rentals in Vail Village but still had some extra time on his hands while everyone else was out skiing.

“I decided to stop feeling sad for myself and hop back on the horse and I would say that the knee injury was a major factor in really wanting to start working hard again,” Pillsbury said. “I’ve always thought of myself to be an entrepreneur and felt like I could make something out of nothing and build something on my own.”

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The wheels started turning in Pillsbury’s mind and one area of interest was putting together digital solutions to help businesses with online presence through website design, search engine optimization, client relationship management and marketing.

“I’ve always thought that’s a fascinating topic and super cool, and researching it really helped me keep my mind off my injury,” Pillsbury said.

Like most teens, Pillsbury took to social media and the internet to seek more information.

“I was immersing myself in TikTok and YouTube videos, anything I could get my hands on. Different ideas, different ways to change the industry in terms of what things I could do differently. And then apply that to the Vail Valley, which is made up of small businesses. That’s our economy. And small businesses are why people love coming here,” Pillsbury said. From there, was born and Pillsbury reached out to his good friend, John Slevin, to help him out.

“I was thinking it would be a one-man show, just me. But then I brought the idea up to John. And that’s really where I saw his mindset and my mindset come to fruition and light and since then, it’s been me and John as one team,” Pillsbury said.

“I think we were at a soccer game or something and Winston brought up this idea and I was super excited to come on board to work on this,” Slevin said. “Two summers ago, I worked with my buddy, and we tried to run a social media marketing company. And so, I had experience with the cold calls and the sales aspect of things and kind of just grew a better understanding in that field. We had a couple of meetings and then we started Astrosoft.”

Pillsbury is a junior at Vail Mountain School, and Slevin is a junior at Battle Mountain High School. Pillsbury is 17 and Slevin is 15.

“John moved up a grade, he’s my smart friend,” Pillsbury added.

Being young has its pros and cons.

“Well, since I’m 15, I can’t even drive anywhere, and we did have to have our parents sign off on our LLC, and school and sports are big a commitment, but we love working on our business. It’s exciting and fun to learn how to help our customers,” Slevin said. “We’ve got class and then practice and homework and then we’ll call each other at 9:30 p.m. and talk business.”

Their young age is eclipsed by the fact that they are eager to serve their clients and make a difference.

“If John and I look professional, act professional and can genuinely help someone or a small business and connect with them on a personal level, in their eyes, they should see that we are young, committed, dedicated kids who want to help them reach their goals,” Pillsbury said. “A huge connection we share is our mindset and that’s contributed to our business and how we grew success together and we’re still growing success. And we want to strive for the moon and that’s why we’re a great team,” Pillsbury said.

One advantage they do have is they are so knowledgeable about social media and can help out their clients who might not have the time or skill to use it properly. They also see social media differently now that they are in a business that uses it as a tool.

“My perspective on social media has completely changed from a way to kind of procrastinate things and having it be more of a negative. But now, I see is as a very beautiful tool to help small businesses grow their business,” Pillsbury said.

“I agree that it was something I would use to just distract myself. I understand now that it’s a platform to push a message and it can be beneficial for businesses and just anybody that has something to sell. It’s a great tool for businesses to show off their hard work and show off their amazing business with cool, unique things,” Slevin said.

The young entrepreneurs are also learning a valuable business lesson that it’s sometimes not what you know but who you know. Their first client was the father of a friend of theirs.

“Our families were on beach vacation together and he was talking about his business and some of the problems they were having, and my wheels started turning and I knew we could help him. And then from there, we got our first client. I called John the second it happened, and we were jumping up and down. We were really excited. It was a great feeling,” Pillsbury said.

Justin Roach is the CEO of Performance Outdoors and Astrosoft’s first client and is impressed by the work Pillsbury and Slevin do.  

“Astrosoft used today’s technology and AI enhancement to completely reconstruct Performance Outdoors’ website and lead generation strategy,” Roach said. “As an entrepreneur who has started and sold multiple companies, it’s great to see young entrepreneurs put their necks on the line and strive for excellence.”

“Since Justin was our first client, we were still learning a lot. But John and I were willing to do it and we knew that we needed to get this done for someone that we respected and someone that we knew,” Pillsbury said. “And thank God for Justin, he allowed us to have that learning curve and really let this whole thing happen for us.”

Astrosoft has since taken on more clients, and the teens are learning to balance and prioritize tasks and school work. Creating Astrosoft has sparked a new enthusiasm at school, too.

“I’m in an economics class right now, and I definitely see how supply and demand type principles apply in a business world, and it’s definitely been helpful,” Slevin said.

“I’m a co-leader of business club at school and since I’m an upperclassman, a big part of the club is being a mentor to a freshman or sophomore, which is really cool for me because I’ve always had a mentor and I think that mentorship is the most important thing and it’s caring for someone more than you care about yourself,” Pillsbury said.

What’s next for Astrosoft?

“Big things!” Pillsbury said. “I think doing the little things right, staying true to ourselves, not becoming complacent, still coming into each meeting with a little bit of nervousness because that shows that we care, those are the things we need to keep doing and then just get better at each thing that we do and grow it.”

“Keep growing the tree and let’s take it as far as we can and help as many people as possible and learn along the way,” Slevin said. “If we stay focused and stay positive, we can go a long way.”

“We have this drive to create something for ourselves, and that can be overwhelming, but we have a whole life to live, and we want to get started now and we want to create something for ourselves,” Pillsbury said. “It’s hard to believe that my knee injury and surgeries that were so debilitating have lead us to this, but I’m glad it did.”