Spotlight

Ryan Quigley

Trust Spotlights

Ryan Quigley

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Ryan Quigley is a former Punter who played five seasons in the NFL. Quigley was a part of the New York Jets, Jacksonville Jaguars, Arizona Cardinals, and Minnesota Vikings before becoming an entrepreneur.

Q
What was your Wraparound experience with The Trust like? Why did you come in for a Wraparound?
A

Nobody wants to really put their mind in the space of, ‘Oh, I'm not playing football,' but when The Trust reached out to me, I was very interested in coming in for a Wraparound. It was one of those things where you’re told about all of these benefits while you’re playing and you think you have a good understanding of them, but after going through the Wraparound I realized that I was unaware of about 70 percent that was new to me.

The best part was getting to meet everyone in-person and being able to put faces to names. It was helpful because now I know who to call for different needs. It helps you know who to call. That part was big for me. It was definitely worth the trip — I feel like now I have a full understanding of what’s available to me as I continue my life outside of football. Wraparounds are definitely something every player should try to attend whenever they have the opportunity to.

I feel like now I have a full understanding of what’s available to me as I continue my life outside of football.

Q
What was the process of getting set up with a Trust Program Manager like?
A

My Program Manager, Nicole Jordan, is awesome. Having the opportunity to meet in person is huge. It helps to be in a setting where you're able to get everything off your chest. It gives you the opportunity to ask something that maybe you weren't comfortable asking in a group setting.

Nicole was able to walk me through everything step-by-step so I had a better understanding of how The Trust could help me.

Having the opportunity to meet in person is huge. It helps to be in a setting where you're able to get everything off your chest.

Q
When you began your transition, what was your support network like?
A

I’m fortunate enough to have a great support network. My fiancée, Morgan, was excited to see me experience the Wraparound.

A lot of single guys or guys that aren't married yet don't really think about or realize how this could affect their future families. But for the guys with families and guys like me, who are just starting their families, it’s so important to understand the benefits that are out there and how they can help starting right now.

... it’s so important to understand the benefits that are out there and how they can help starting right now.

Q
Tell us about the company you Co-Founded, Playeasy? How did it get started?
A

My college roommate, Sean Flaherty, and I used to run kicking camps in the summer, and one of the main issues we would have was finding fields. We would basically go on Google and look for football fields to use — it was a very painful process.

We then connected with some of our former classmates — Kerri Shields, who played basketball at Boston College, and Brian Hamor, who was a point guard at Stone Hill College in Massachusetts.

We did some research and realized the process to rent a field was old-fashioned and there was no modern technology that helps handle renting out spaces — especially from the renter's perspective. So, we started Playeasy.

Q
What is Playeasy?
A

Playeasy is a platform that helps schools and facilities manage their facility rentals – starting from how renters find and request their spaces, to automating and tracking their payments and billing process.

We work primarily with colleges and high schools that currently rent out their spaces or ones that are looking into it but don’t know how to get started. Unlike traditional software, it takes a few minutes to get started on Playeasy. In a few minutes, you can go from an unorganized process of back and forth emails, calls, paperwork, to having it streamlined and automated all in one place.

Q
What is your role in the organization?
A

I’m currently heavily involved in the sales and business development side of the business, but I've been a part of everything that has been involved in building Playeasy from an idea to a functioning company.

With such a small company, everyone has to wear many different hats. From my end, one of the things I stressed about the most when starting with the business was that my primary skillset was punting and that I did not have a lot of experience with the skillsets required to work for a startup. I thought about that often ... ‘Am I going to be able to excel in business? Will I be able to perform and to lead in a role I am not experienced in?’ However, building Playeasy from the ground up with my colleagues has served as an amazing education for me and I feel almost caught up to my Boston College classmates who have worked in traditional office jobs since we graduated.

I thought about that often ... 'Am I going to be able to excel in business? Will I be able to perform and to lead in a role I am not experienced in?'

I thought about that often. ‘Am I going to be able to excel in business? Will I be able to perform and to lead in a role I am not experienced in?’ It builds confidence for me. As former football players, we have to understand that even though we may not all be caught up with various industry jargon or technical skills, we all have invaluable experience and are fully capable of jumping in to a business setting. I have grown professionally through Playeasy, and I now get a front row seat in business meetings and don’t hesitate to participate in when I have something to say.

Q
What advice would you give another former player who may be going through a similar transition and wanting to pursue a career in business?
A

It’s OK to worry. It's OK to stress. But you have to go out and make things happen. For me the biggest hurdle when I started was my hesitation to just call people. My role used to involve a great deal of cold calling — I had to call as many facilities and organizations as possible but used to be nervous of not sounding knowledgeable or professional enough. However, through that experience I realized I was fully capable and that with practice I would grow to be confident when I pick up the phone to call a potential customer.

The biggest confidence booster was just going for it and doing it — similar to with football. One of the things that makes a lot of guys so good at football is that they never hesitate because they are confident in their skill and abilities. They just go out on the field and perform. With business, if you just go out and give it your all, you will learn through experience. Don’t be afraid to step out there. You have more skills than you could ever imagine.

Don’t be afraid to step out there. You have more skills than you could ever imagine.

Q
Why would you encourage other former players to get involved with The Trust?
A

As football players, we all have similar mindsets where we feel like we can do it all on our own, but it's nice to know we don’t have to. I would encourage players to get involved with The Trust because it will help them optimize and get the most value from the benefits they earned through their hard work playing football.

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