of Companies: 25 years of growth and innovation
By David Gargaro
How they met
Vanessa: Roy, I understand your journey started off in university… you were watching a hockey game with your girlfriend, her roommate, and her boyfriend. Tell me about that day.
R. Jason Ashdown: Yeah, just to make things confusing, Jay and I both have the same name, and our girlfriends both had the same name as well. Our girlfriends lived together, and that’s my first memory of meeting JC. We hit it off right away. And then starting to learn he was into real estate. I had always been a young entrepreneur. I was always looking for a way to make extra money, just to be able to get the things I wanted. And whether it was… hosting parties or scavenger hunts or building things and selling picnic tables, building decks for my teachers… Meeting Jay and seeing somebody with similar spirit was pretty cool. I didn’t realize at the time I would marry my wife and we would have a long relationship. I’m still married to her today, but I’m also married to him.
Vanessa: Wayne, you also knew Roy in university, but your paths with the others didn’t cross right away. And you went an independent route when it came to business. Tell me about that.
Wayne Byrd: I had met Roy in my first year of university, through mutual acquaintances, at a party at the residence I was living in. And then a few years later, living off residence in house, I met Jason, and we didn’t realize we had met each other until many years after that. It’s interesting how things intertwine and where we meet back again. Unlike most kids in grade six, I knew I was going to be an accountant. I don’t know why. I was good at math. Numbers seemed interesting. And the floor hockey coach, who I got along well with, was an accountant. So that must be what I need to do. I enjoyed it and stayed focused in accounting and working the numbers.
Vanessa: It sounds like university was a start for all of you. I know, Marty, you had an entrepreneurial spirit from the beginning. Where did that come from? Who was your mentor?
Martin Castellan: I went to the University of Guelph and I was taking the economics program. We had dinner at my Uncle Rick's and he was always interested in our lives and education. He was a chartered accountant in the private sector, and I was about midway through university at the time, not knowing what I would do with my career. And I [asked], “Where’s the money?” And Uncle Rick said, “The money’s in sales.” And I’m thinking, “Okay, sales and houses.” I got my real estate license my last year of university… And we sold houses for a while. When we bought our own houses, we could earn commission on them. It was working well for us. It was those times we realized there’s a real passion, call it an addiction, for income-producing assets. And in that time during university we learned a lot, even outside of the classroom.
Vanessa: [Jason,] what ignited the passion that you had for business? Where did this all start?
Jason Castellan: I think we’re all from humble upbringings. We weren’t allowed to miss school. When we had jobs before we were 16, our mother made sure we got to our jobs and got home from our jobs. That was as integral as going to school. I was working and making money and paying our way. And then our dad helped us buy a student rental later on we could rent out. We lived in the basement and we rented the rooms upstairs, and that covered the place. Then going across the street and buying the next one and buying the next one and getting our real estate licenses. It was very addictive. One thing led to another to another. And then meeting Roy, it was just the evolution. I don’t think any of us thought it would be what it is today, but it was certainly something we could keep doing and could scale and grow indefinitely.
Dealing with challenges
Vanessa: You have been in this industry for 20 plus years now. I’m sure you’ve seen your fair share of challenges. Marty, what has been the biggest challenge for you in business?
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left to right, Jason Castellan, Martin Castellan, R. Jason Ashdown
left to right, Andy Coutts, R. Jason Ashdown, Jason Castellan, Martin Castellan
Martin Castellan: We started off in property maintenance, like fixing stuff, and then we were the property managers, and then we were managing the property managers. Every time we replaced ourselves with people who thought [they] could do it better… Actually adapting to that transition with the needs of the company where, as we grew the company, it was very challenging at times because it wasn’t a perfect trajectory. I found that a challenge to continue to evolve as we grew the company.
Vanessa: I know there are some challenges you guys have had personally as well. Roy, I know you lost your father at a very young age and that was difficult for you. Tell me a little bit about your father and how that experience sort of helped shape you into the man you are today.
R. Jason Ashdown: My dad was, from what I understand, a very handy guy. Strangely, he was into real estate throughout his short life. He passed away when I was nine. At the time, I didn’t realize it as a challenge, but as you grow older, that situation probably made me very selfsufficient. I had to learn how to do things early on if I wanted those extra things out of life. I needed to find a way to get them, and I had to be creative. My mom was very blue collar. She worked at Goodyear Tire when she was 14 years old, born during the Depression. She was a hard worker. I saw it, so anytime there was an opportunity to leverage either making a deal or making a trade or building something and selling it, I was in there. I feel that challenge of growing up with just a mom who was awesome gave me a lot of the tools I needed to succeed in business.
Vanessa: Absolutely. It’s nice to see you’ve taken those challenges and the things you’ve learned and turned it into something so wonderful. I understand a few of you have also had some serious health issues. Tell me a little bit about that experience and how that affected you.
Jason Castellan: I was diagnosed with throat cancer and dealt with that in 2016. The guys were great supporting me as I dealt with that. My family rallied around me. It was a very trying time. It’s a shadow that hangs over you for the rest of your life, and you wonder all the time. It changes the way you think and your outlook on life. Being in a business where you have investors, where we’re trying to please them and trying to do that, it’s time to take a break from that from time to time because your health, both mentally and physically, is important if we want to be around for a long time.
Vanessa: Wayne, you also had a health challenge, it happened to you in the way of a stroke. How did that experience help shape your perspective on things going forward in life?
Wayne Byrd: For me, it was right after Jason got back from surgery in Philadelphia. April 5th, 2016. It’s around this time of year where I get a little reflective. I was home alone when it happened. My wife had dropped off our son at school, found me on the floor, and from there I was rushed to the hospital in Guelph. [There is a] critical four-hour window to get TPA, the blood clot buster… It made me be a little more reflective on the things that I have, I had, and what I need to spend a little more time on. I spent a little more time with the family, a little more time traveling. I’ll just say work-life balance... It did give me a bit of a different view on myself and on what was important.
Staying motivated
Vanessa: You have been business partners now for 20 odd years. What keeps you motivated? What keeps you going?
R. Jason Ashdown: I’m built in such a way that I need to get stuff done. I need to have productivity in my day to day. That keeps me motivated. I used to resist it and wonder why I was that way, but I found wrapping my arms around it and being productive I’m just happier. And in that, I’m a helper. I like to fix things. I like to get involved with situations when things go wrong.
Vanessa: Jason, what about you? What keeps you motivated in all this?
Jason Castellan: With these guys, we have a similar mindset, we have a similar motivation, and we can get through it together. If we can put our resources together, we can have a compounding effect on the outcomes of what we’re trying to achieve. That’s very motivating to pull together and do that kind of stuff. I’m also motivated by people who say, “You can’t.” If you tell me I can’t do something, I will go out of my way to prove you wrong. Not on silly things, but on the way business is done, on the way we raise our capital, on the way we own our real estate and the way we manage our things. We do things a little bit different. It’s a pretty basic business what we do. If we can tweak it, we do it a little bit different than what’s the norm and the standard that’s out there. I think that’s been a huge part of our success.
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left to right, Jason Castellan, Martin Castellan, R. Jason Ashdown, Wayne Byrd,
Looking to the future
Vanessa: Wayne, you had mentioned you’d love to see Skyline a household name. How are you going to get there? What steps are you guys going to take to achieve that?
Wayne Byrd: From our humble beginnings, we didn’t think we would get to this size. We still meet weekly and talk about goals and ambitions and try to create strategies. We want to be the household name. We want to be the Advil, the Tylenol, the Coke, the Kleenex. If somebody wants to reach for an investment, Skyline has to be the investment they want. We want to differentiate ourselves. And in 25 years from now, I hope that all of the stakeholders, investors, suppliers, tenants, banks, they understand that Skyline will be first of mind as we continue to grow and push the envelope.
Vanessa: Marty, I know 25 years [is] hard to imagine. What would you say would be the ideal setup for Skyline in that time?
Martin Castellan: I have no problem imagining it. It’s how accurate we are. Starting today, we have a responsibility to build ourselves to be generation proof. That’s a goal here. I want to look and say, “Look what we’ve built.” We’ve built something here that is set up for success for the next generation and have it strong and stable and solve a problem for people that want to invest with us.
Advice for others
Vanessa: What do you think would be the best advice for somebody who’s thinking of getting into this industry? And why would that be the best advice?
Jason Castellan: An early investor I look up to told me once when we were walking together to shoot for the stars, and if you get the moon, that’s pretty good. Set your goals far. But I caution anybody
who wants to get in business for themselves. If you’re going to shoot for the stars, be prepared for the journey. Be prepared for the toughness. It’s not always going to be fun. There’s been tough days that we’ve all had to deal with. Your wins are great, but the losses hurt, and you have to lick your wounds and get on with things. But if you’re going to shoot for the stars, go for it and go for it hard... You learn more from your mistakes than you do from your wins, and we’ve done lots of learning.
Wayne Byrd: Be humble and stay humble. Humility has been a key to our success. We are real people and we are going to make our share of mistakes. We’re going to make some missteps. Augment, grow from it, and just pivot and own them. Just be right up front. We made that mistake, own it and have that strength of humility.
Vanessa: Your lasting business relationship is a testament to you. You are definitely an inspiration for a lot of people looking into business. I want to thank you again for sitting down and sharing your points of view with us.
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Skyline celebrates its 10,000 suite milestone in Stratford, Ontario, in 2014.
left to right, R. Jason Ashdown, Wayne Byrd, Martin Castellan, Jason Castellan
Jason Castellan, Chief Executive Officer
R. Jason Ashdown, Chief Sustainability Officer
Martin Castellan, Chief Administrative Officer
Wayne Byrd, Chief Financial Officer
