Serial Entrepreneur - Ryan Corry


Ryan’s entrepreneurial portfolio career began while he was playing NCAA hockey for Plattsburgh State University in New York State. As a project during his senior year in university, he had to create an event to generate income. “I organized a large American Pie style party and hosted it at an open-air pub with about 700 people in attendance. I made a profit and crushed everyone in my class!” He said with a smile. This was the beginning of Ryan’s entrepreneurial juggling act.

I met Ryan at a Career Development Mix and Mingle hosted by our mutual connection, Joy Ulrich. Ryan was at the mix and mingle to pitch his second startup business called Skillpics, an online platform that visually connects job seekers and employers. Ryan had hit the pavement with his concept and was actively connecting with different organizations in Calgary. I later ran into him again at a conference in Edmonton where he was marketing his platform to career coaches from across Alberta. I was impressed with the product and curious about Ryan’s entrepreneurial portfolio career. Ryan was kind enough to later meet me in a café in Bridgeland in Calgary where I sipped a latte and quickly tapped notes on my laptop as the story of his career effortlessly poured out.

After playing for Plattsburgh State University, Ryan moved to Pensacola, Florida to play hockey in the Southern Professional Hockey League with the Ice Flyers and continued juggling hockey and event planning. He planned the same American Pie style event again, had a successful return and realized he could make a profit in the industry. His hockey career then took him to Europe where he played with the Lyon Lions in Lyon, France. He again juggled hockey and events planning, organizing another event called Fall Fest, but this time across continents in New York State. “I learned that playing hockey and coordinating events from another continent was definitely challenging. But I made it happen because I loved working with performers and discovering talent.”

While playing in France, Ryan decided to hang up his skates and return to Canada. He had achieved his goals of playing hockey in the U.S. and Europe and he wanted to get back into the community and try out different things. Prior to returning to Canada, he decided to take a detour and travelled to Thailand. He said, “I needed to reset and gain perspective. I wanted a clear head for the decisions that were to come.”

A career change is never easy and for professional athletes, it can be an adjustment. Upon returning to Calgary, he said reality kicked in and he started to look for a "real" job. He had a good work ethic, had graduated at the top of his class and didn’t think it would be hard to find work. But, it was. “I had to try different ways to get noticed. I created my first cover letter, which was a storyboard of my travels and volunteer work. It was a visual representation of my skills designed to capture the attention of employers,” he explains. “I did all this work but it didn’t match up with how employers were looking for talent. I had been away from Calgary for six years and I was finding it challenging to connect with employers.”


His Skillpics concept was evolving in his efforts to connect with employers. However, while continuing to find work, Ryan decided to use his skills to help in the community. “I took over responsibility for and re-incorporated a non-profit organization that executed a charity formal event. The event preceded a Christmas Classic hockey game with friends who were just starting to play, right up to professionals. I used my hockey background and event planning experience to help raise money. I wasn’t paying myself with this, but I needed to create work for myself. It was rewarding to be doing something worthwhile."

He continued planning charity events while simultaneously looking for paid work. In addition, he had also been on the lookout for a well-made onesie for his girlfriend. The adult onesie craze had hit both Europe and Canada, and Ryan’s former Swedish roommate had purchased a high quality, European-made onesie for 250 Euros. While in Calgary, Ryan couldn’t find a product with the same quality, so he decided to get one made, “In the spring of 2014, I actually got my first onesie sample and spent about $300 for three rather than ordering one for 250 Euros from Europe.”

Ryan had an interest in fashion and creating a brand. “When I created the onesie, I chose the name UNI which was slang for uniform in the hockey world. By chance, UNI also means one in Spanish. I built on the name with UNI chillwear.” He ordered three and wore a sample onesie to the bar to show his friends. It was a well-made product so he decided to make 50 more. “I took out a loan, made more, sold them all and started to realize this might be a business opportunity.”

Ryan’s former teammate, Jeff, who was doing his MBA, thought he could apply his learning directly to this new potential startup. This helped Ryan get motivated to complete the business. He adds, “We went from 3 units to 50 to 125 then 250 to 400 and we are now at 650 units and getting better margins. We completed our second winter and we have done $140,000 in gross revenue. We wanted to create a brand so we branched out to sweaters, t-shirts, hats and sunglasses. We have mostly done word of mouth marketing and through good customer service, we have built client relationships on-line. We also market at trade shows, festivals and events.”

While building UNI chillwear, Ryan networked with graphic designers, models, and photographers and found that finding talent was inefficient. “I was wasting time going through Facebook and Kijiji, asking for coffee meetings to see portfolios of work. If they weren’t the right fit, I would start looking for someone else. It was a waste of my time to try to hire someone this way, so I started conceptualizing an online platform where I could easily go to a portfolio of work. I drew my first platform for the on-line concept Skillpics. I thought the platform would help jobseekers connect to companies that needed people.”

While working on both startups, Ryan landed a job with Bust Loose managing events, travel experiences and basic operations of the business.  He worked with Bust Loose for a period of time before he decided to quit to focus on UNI.  Once the business started to grow, Ryan reentered the workforce and with his event planning background, he landed a job with the Alberta Ballet. “They hired me to do their biggest event.  Shortly after the event was pulled, my boss was laid off and I found myself doing a plethora of jobs around the office. My title was changed to Project Specialist. I did anything from writing RFPs to connecting with key people in Calgary. It was a great learning opportunity, but I ended up getting laid off in the recession. I then turned my attention back to Skillpics.”

Ryan knows how to adapt, and juggle multiple ventures, key skill sets for entrepreneurs and portfolio careerists.  Skillpics had sat on the back burner while he was working with the Alberta Ballet.  Ironically, once laid off, he had time to work on the platform that was to easily connect job seekers and employers. “I strategized, invested from UNI chillwear and hired Vog Calgary App Developers, a solid mix of people with an energetic, honest work ethic.” Skillpics had started from a cover letter he had created years before as a job seeker. He further refined his idea as he became an employer frustrated with trying to find talent for UNI chillwear. Ryan had started his portfolio career as a hockey player/event planner and was quickly becoming an entrepreneur/business owner juggling a growing business and a new startup.

Ryan’s career has met some challenges since he returned to Calgary.  However, he seems to have an innate determination to succeed and a will to keep working towards his goals regardless of setbacks.  When I asked him if he could pinpoint some advantages of currently being an entrepreneurial portfolio careerist, he didn’t hesitate when he answered, “I like to be able to make money and be successful, but I want to make money doing what I love.  The amount of money I make helps me keep track of how successful I am.  Whether it is for myself or for a charity.  It is a measure of success because if you are creative, efficient and strategic and you do these things well, then you’ll have a large degree of financial reward. The fruits of your labor will be reciprocated. Money can be like a trophy.”

When it comes to disadvantages, Ryan believes time management, the energy that goes into a startup and the lack of capital are the tough parts of starting a business. “I had to mix in two professional jobs because we aren’t going to make money overnight.” He continued, “At times, skepticism creeps in. I wonder whether or not all of this work will pay off in the end. However, I counter skepticism with the idea that I’m making an investment. I’m investing into a business and taking a risk like every person who pours money into getting an education. When they come out of university, they have to find a job and pay their investment back.” He then added, “We are all investing into our future in a different way.”

Although the road ahead may be challenging, I believe Ryan’s tireless work ethic, his ability to see gaps in markets and his determination to solve problems will continue to turn his investments into a successful entrepreneurial future.

For more information on Ryan's businesses, tap on the following links: