Episode 41 Encore: From NHL Prospect to Community Leader | Ryan Donally

🎙️ Encore Episode: Ryan Donally | From NHL Prospect to Community Leader

Some conversations are worth revisiting.

In this encore episode of Cracking the Success Vault, Sean Penhale sits down with Ryan Donally, President & CEO of the Windsor-Essex Regional Chamber of Commerce and former NHL draft pick, to discuss resilience, reinvention, leadership, and finding purpose after unexpected setbacks.

Ryan shares his journey from competitive swimming and professional hockey aspirations to becoming one of the region's most respected business leaders. Along the way, he opens up about the difficult transition that followed career-ending concussions, the lessons he learned from sports, and how those experiences continue to shape his leadership style today.

Whether you're an entrepreneur, professional, athlete, or someone navigating a major life transition, this conversation offers practical lessons on adapting, evolving, and creating impact.

🔑 In this episode:

• Pursuing elite-level athletics and the sacrifices required
• How adversity can create unexpected opportunities
• Leadership lessons learned as a role player and team member
• The influence of family, work ethic, and accountability
• Why sales is a skill everyone needs
• Building a career after a major setback
• The importance of aligning your work with purpose
• Why success is ultimately measured by impact

⏱️ Timestamps

00:39 – Ryan's sports background and competitive mindset

02:43 – Choosing hockey over swimming

05:28 – Career-ending concussions and reinventing himself

09:38 – Leadership lessons from being a role player

20:25 – Family influence and developing a strong work ethic

25:26 – Entering the business world and supporting entrepreneurs

33:01 – Leading the Windsor-Essex Regional Chamber of Commerce

39:35 – Why everything in life is sales

46:40 – Reinvention, growth, and embracing change

49:31 – Defining success through impact and contribution

🎧 Whether you're building a business, changing careers, or pursuing your next chapter, Ryan's story is a powerful reminder that setbacks don't define your future—your response to them does.

Learn more:

https://spectrefinancial.ca

https://spectregroup.ca

Transcript

SPEAKER_00 0:01

I've told people, like, my talent is swimming, my passion was hockey.

SPEAKER_03 0:04

I remember seeing the name, and I never really put it two and two together until I met you a couple months ago.

SPEAKER_00 0:09

Yeah, and you're like, He looked different. Yeah. I probably had long blonde curly hair because like hair dye was a thing at that age. And then uh it was probably also about 70 pounds ago. So if people ever ask me like how long ago I played hockey, I say 50 to 60 pounds ago. There's still wins and losses, they're just different wins and losses. Ambiguities, I love ambiguity though. Like that to me, that's important. Like I don't want to wake up in the morning and know exactly how the day is gonna go.

SPEAKER_03 0:39

Uh so welcome to the uh Success Vault Podcast. Um, we're really excited to have you here, Ryan. Um for those of you, I don't know too, too much about you. Uh so normally I'd have a little intro. I know uh Ryan Donnelly as um, you know, the president and CEO of the Chamber of Commerce here in Windsor. Yep. Um, I know you were drafted by the Flames. I'm a big Flames fan. So that's uh this is gonna be really exciting for me. Um and like we mentioned before the podcast, we're gonna talk about a lot of different things. Um, and so I'm excited to kind of get into it. Cool. So let's start with um where you grew up, uh, how you grew up, and sort of what led you to sort of where you are today.

SPEAKER_00 1:15

Yeah, so I um I was born in London, Ontario, uh 1985, February, cold day, uh snowstorm. Actually, I have no idea. Um, but I was born in London, Ontario, and then my family moved down here to Tecumseh uh when I was two. So I grew up in Tecumseh, went to, you know, people always ask, and like, you're not from here, but like they're like, what high school did you go to? What grade school? So I went to A.V. Graham, went to Victoria Public, went to Bell River High School, um, you know, grew up in the mean streets of Tecumseh, just down the street from St. Greg's and Zare's Plaza and all that stuff. So rode my bike around and ate subway as much as I could. Um, and then um, yeah, I played sports growing up. Uh, have a younger sister. So my parents gave me the opportunity to, you know, explore sports, explore kind of whatever I wanted to do. Um, kind of like most kids grew up playing hockey, ball hockey, and then that turned on on ice and also uh found when I was really young, I had a love for swimming. So I played a little bit of baseball, played a year of soccer, but really started getting serious about two sports, swimming and hockey by the time I was probably nine or 10. Okay. Um, so swimming and hockey were my two kind of passions, and those don't really line up as far as timeline because they're both, you know, winter sports. All year rounds. All year round. It never stops. So um swimming as hockey is where I kind of chased my dreams. And then um as I was going into high school, grade nine was the year that I knew, like going into grade eight to nine that summer, I kind of had that decision of like, okay, what do you want to chase as far as a career? Because I've told people, like, my talent is swimming, my passion was hockey. So despite being a you know top national swimmer and you know, having a whole bunch of club records for the Windsor Aquatic Club, um, I chose hockey. And and hockey was what I focused on from grade nine on. And uh yeah, it got me far enough that you think it's cool that I got draft for the flames. Right. Yeah, I'm sorry.

SPEAKER_03 3:10

Hey man, it's it's exciting. I remember like seeing the draft, I remember seeing the name, and I never really put it two and two together until I met you a couple months ago.

SPEAKER_00 3:19

Yeah, and you're like, he looked different. Yeah, I probably had long blonde curly hair because like hair dye was a thing at that age, and then uh it was probably also about 70 pounds ago. So if people ever ask me like how long ago I played hockey, I say 50 to 60 pounds ago.

SPEAKER_03 3:32

Yeah, it's a weight thing, not a time thing anymore.

SPEAKER_00 3:35

Weight, not time, yeah. That's that's funny.

SPEAKER_03 3:37

Um, it's funny you say that though, because I was very similar. Yeah, um, I grew up playing a lot of different things, hockey, uh a little bit of ball hockey, never got into ice hockey, yeah. Um, soccer, swimming as well, which was my main sport, uh, volleyball, which is where my parents played. And I had the same thing. Um, I would say my passion was volleyball. Yeah, I was never going to be the six foot five that they're looking for.

SPEAKER_02 3:59

Yeah.

SPEAKER_03 4:00

Um, and I was extremely good at swimming. And same thing around that grade nine, grade 10, it's kind of you got to make that choice. Um, for me, I actually hated uh other people's mistakes making me lose uh on the volleyball court. Yeah. Um I was very fortunate that because my parents played, I played volleyball from like three or four. Like the moment I could stand, my sisters and I were peppering back and forth. And so when I got into high school, I was already really good at volleyball.

SPEAKER_00 4:27

And was a libero, was that a thing at that point? No, okay.

SPEAKER_03 4:30

No, it like when I was a new rule, right? Yeah, when I stopped playing volleyball, that's kind of when that came in. Um I would have been really good at that. It would have been your skill, yeah. I would have been great at that. Um, I love diving all over the place and reading plays and all that kind of stuff. So when I when I play now, I that's what I love doing is defense because I don't really jump or hit very hard. Um but yeah, um, so I ended up choosing the the swimming route because that's just the thing that made the most sense.

SPEAKER_00 4:56

Yeah. Right. So and made it national level. And I heard that your listeners are interested in seeing us swim against each other in a race. I guess so. Yeah. I don't know.

SPEAKER_03 5:06

Yeah. Everybody says I should get back in the pool. Um, it's actually been a long time. You and I talked about this uh a couple, a couple maybe a couple weeks ago. Um, I just haven't got back into it. I feel like every time I get in the pool, I start feeling good, getting back in the rhythm, and I say, you know what, let's see how good I am now compared to what I was before, and then I hurt myself and I have to take time off again.

SPEAKER_00 5:27

Yeah, it's and I don't know how to stop that. Yeah, it's funny you say that. Like I uh people are always like, Oh, how much do you play hockey these days? I'm like, I don't. Two things. Like, I I have my knee is a wreck, so like I can't play hockey. But I remember especially when I retired, um, it took me a couple years to go like, I can actually enjoy men's league hockey because you know, you you get to this level that you think is, you know, I was as close as you could possibly be to be full blown NHL or full career, right? And um when that ended, and it was, you know, injuries that ended my career. It wasn't that I just got too old, fat, tired, whatever it might be. So you get back on the ice the next year, but you're not practiced, you're not trained. So it took me a couple years to realize I'm like, I'm never gonna be as good as I could be, right? And I'm never gonna get to that ever level again. So if I if I know that, I can go have fun. I can go just go play hockey with my buddies and have beers and like, you know, just do all the things that adult men's league hockey is about and camaraderie and you know, just enjoying that time. Um, but it took me some time to get to that point, and then my knee just kind of kept deteriorating. So I don't play at all anymore. I put I I coach seven-year-old kids hockey. Yeah, it's great.

SPEAKER_03 6:33

And are you coaching at the university still?

SPEAKER_00 6:35

No, it's been a few years. So I I did um so when I stopped playing hockey, um, I was actually telling a story today. Um, so I had three concussions my last year in pro, and that's the reason why I retired. But at the end of that year, uh, because I was in the ECHL at the time. So NHL, AHL, ECHL, that's kind of the three levels. Um, concussion in the NHL, start of that year, concussion in the American Hockey League, middle of that year, and then Anaheim Ducks, who I was employed by the time, they said, okay, Ryan, go back down to the ECHL, East Coast Hockey League. Don't do anything dumb, don't fight, don't just be just play, just get healthy, right? And uh, you know, next year we'll bring you back up and we'll we've got plans for you with the ducks and see where it goes. And if you make it, you make it. But um, so, anyways, at the time there was only one coach in the American the ECHL, um, which, you know, ECHL has smaller budgets, you know, not a ton of fans. I was in Bakersfield, California. So when my career ended from uh the playing perspective, or my season ended from playing perspective, three concussions, they said, Ryan, do you want to start coaching? And that's actually how I got into coaching, is my my knew my hockey year was done, right? But they needed another guy on the bench. So I started coaching the defense and um loved it. And then I started coaching U Windsor men's hockey when I retired over the season, uh the summer, sorry. And then uh coached junior B. Thought I was gonna chase the pro hockey dream as far as like a lifestyle and career, and then um, you know, had the opportunity and I just said, you know what, it's not for me. I'm gonna, I'm gonna get married, I'm gonna settle in Windsor, Essex here. I'm gonna you know get married to my girlfriend who is now my wife, who is now my mother of my children, and uh and life went a different direction, and I'm very thankful for it.

SPEAKER_03 8:17

Yeah, it's interesting you say that because I think, and you bring up a very good point that you retired from hockey because of injuries, yeah. And you kind of came to the realization that you just weren't going to be able to play at that level anymore. Maybe, and I don't know. This is I'm I'm spitballing this. Maybe so I chose to retire because I was just done.

SPEAKER_02 8:39

Yeah.

SPEAKER_03 8:40

I it wasn't an injury, it wasn't, I was just lost the love of it. I'm I'm over it. I was tired of spinning my wheels. I was tired of trying to make the Olympics and not getting there. And I came close, um, but I chose to retire. And so maybe that's why whenever I get back in the pool, I'm like, maybe I can still do this. Because it wasn't like it was just a choice, and maybe I just haven't come to the realization that uh I'll never be that swimmer. Uh, I don't know.

SPEAKER_00 9:05

And um I think the cool thing about swimming that taught me is like how far you can actually push yourself and like when you think you're tired, you're actually not. And like, how far can lactic acid threshold take you? Yeah, and and it was fascinating because you know, I I didn't know what I was learning at that time and like how far you can push your body until I'm now training to be an Olympic like a world-class hockey player, and I'm training the bike or I'm training in the offseason. And before you know it, like I'm with Calgary, like destroying VO2 records, yeah, and like crushing the wind gate on the bike. So VO2 is uh blood oxygen level. So I had that record. I I may well still have it. I don't know. Um, but I destroyed hockey players on VO2, and I assume it's because either I grew it growing up, my long capacity, or just the fact that you know that was how I was built and I could lots of swimmers push my bike farming.

SPEAKER_03 9:58

Yeah, I don't know if it's just that we have to hold our breath and then we have to whatever, but we all have pretty high VO2s.

SPEAKER_00 10:04

Yeah, high VO2, and then you know that translate great to the bike. So I was a really good cyclist, and who knows? Maybe that's my next thing, right? Yeah, um, I don't have to run around on my knee blowing that thing up. So yeah, maybe I'll try to race people on bikes.

SPEAKER_03 10:16

It's interesting you say that because I'm I'm very I would say I'm very similar in the sense is like uh volleyball is that thing. I absolutely love it. It's a game. Um, you can control things, you can't control some things, but swimming is like I control everything, right? Yeah. Uh so did you learn that hyper competitiveness from your parents?

SPEAKER_00 10:36

I assume so. Um, I I don't know if it's one of those things that you you go, your, you know, your mom or your dad or parents or whatever will go, you need to be more competitive. Like I think they, as a parent, especially with me, I've got a five and ten-year-old boys, you put them in situations where they can learn and try and you know, you shape them however you can. Um it's funny, about three weeks ago, my son was just kind of lollygagging on the soccer field, and this was like multiple weeks in a row, and he loves soccer. He's just walking around and I got really frustrated with him. This is my seven-year-old. I said, like, I don't care if you score, I don't care if you I want you to have fun, but like it's more fun when you're running and you're competing and you're going out there and you're trying, and and honestly, the last three weeks he's been outstanding. Like, he's running hard. And I'm like, see, this is like, I don't know if that's what my parents did to me right to make me competitive, but like, um yeah, maybe the little words of wisdom that help him part like life goal life lessons on your kids.

SPEAKER_03 11:34

So did you learn, did you know that you wanted to do uh be a high-level hockey player as a kid? Or it wasn't something until you're like, okay, I'm really tall, I'm really good. Yeah, uh, this could be something for me.

SPEAKER_00 11:49

I was never really good. Like I was good, but I was far from a prodigy. Like there were kids out there that you're like, that kid scored 50 goals a year. Like I was always the second or third best player on the team. Okay. Um, but I had a good all-around game. Like I was never the kid that scored hat trick after hat trick, but uh I would play lots of minutes, I could play every situation, I could be tough. Like, I mean, and that kind of translated my career. Um, there's a lot of things I could do to help the team. I was a good leader, I was always a captain. Like um, being becoming a professional hockey player is different than being a really good 12-year-old hockey player.

SPEAKER_02 12:24

Right.

SPEAKER_00 12:25

Right? Like it's just it's so much different because um there's only a couple, uh like if you look at the NHL, there's only six guys that try to score goals. I mean, they all try to score, but like there's six guys that are like really good, elite OV. The best hockey players you've ever seen in your life. David, OV, Sidney. Yeah. Those guys, right?

SPEAKER_01 12:42

Yeah.

SPEAKER_00 12:43

And I learned that when I was 18. I watched Jerome Ginla shoot pucks after practice, and he was hitting one timers, like this, my first NHL camp. And he's hitting one timers, and he's going, you know, coaches yelling, short side, bar down. Sure enough, slap shot, hard as you've ever seen in your life, short side, bar down, uh, passing it in front of him, behind him, off his back foot, like as hard as you can make a shot on the player to shoot it, the coach was doing that to him, and he every single time. And at that point, I'm like, I'm never gonna be that guy. Like, I'm I'm never gonna be that good. The skill of those guys, McDavids, or at the time it was, you know, um Corey Perry's like those guys so much better than you could ever imagine. Yeah, so what is a third line guy? What does that guy do? Um, you know, what does Sean Horkoff do? Like that was a guy that I looked at. And what about the, you know, the third line left winger for the Edmonton Oilers? Like, how am I that guy that wears an assistant captain but is not the guy that scores 50 a year?

SPEAKER_02 13:42

Right.

SPEAKER_00 13:42

And he's got a 12 or 15 year career, and he's the captain wherever he goes. Like, who's that guy? Yeah, because that's who I could be. Um, and that's what I tried to become. And you know, I never scored, I was never the leading scorer on my triple A team. I mean, I played triple A all the way growing up, so like, yeah, that was I was a good hockey player, but I was never like, oh my god, you gotta come watch his play. Whereas swimming was, I mean, I could win any race I was in anytime, no matter what, without training. Yeah, like I'd be on the ice five times a week and I'd go in the pool three times a week, and 12-year-olds at that age are swimming seven or eight times a week. Um, I just had that. Yeah. Yeah. So that's really, yeah.

SPEAKER_03 14:21

Yeah. I mean, I was super athletic. Um, I mean, you know, learning, learning golf, learning whatever as a young kid. But I was I was slightly different. I I watched Donovan Bailey win his gold medal in '96 from my living room floor. Uh, and I was like, Olymp Olympics is something I want to do, that's what I want to do. And I didn't know what sport I wanted to do. I didn't know I was still swimming at the time. Obviously, I started when I was six, so I'd been maybe a year or two. Yeah. And I was like, man, that would be really cool. But I didn't know if it would happen, what sport it would happen in. But I was just really athletic, very gifted athletically. And you teach me the rules of a sport, yeah, I'll be good at it. Even as like an adult learning something, teach me how to play tennis. I'll be pretty good for you know a washed up 35-year-old swimmer. So yeah.

SPEAKER_00 15:12

Uh, but um Do you want to hear something crazy about being competitive and like uh practicing and like the ultra competitiveness? I am ultra competitive. Like I think you can ask any of my friends, my wife, I am ultra competitive. I love golf. Like I absolutely love golf. Okay. I will not let myself practice head golf.

SPEAKER_03 15:30

You won't.

SPEAKER_00 15:31

I will never practice, I will not practice golf. I will not go to the drive range, I will not work on my wedge because the minute that I start saying I'm gonna try to be better at this, then I have expectations. And then I will not live up to those expectations of the golf course, and the frustration will come in.

SPEAKER_02 15:46

Right.

SPEAKER_00 15:46

So if I know that I go out there and I'm like, I'm gonna go play with my buddies, I'm you know, good enough, I can play any course, but I'm not gonna work on my game. Yeah, because if I work on the game, then I expect to be better.

SPEAKER_02 15:58

Yep.

SPEAKER_00 15:59

And golf is the most infuriating game in the world if you've played it. Uh, and I could see myself just hating the game because I'm trying to get better at it. So now I just enjoy it.

SPEAKER_03 16:08

It's funny you say that. Uh, literally two weeks ago, I play in like an old, you know, father's, you know, no drinking league. Yeah. Um, every other Sunday. And I shot my best round of my life. Uh, I went shot 76. Great scores. Fantastic. Eight better than I've ever done in my life. Don't know where it came from. I just uh approached shots, just happened to always be on the green and not long or short or left or right. It was it was one of those days. One of those days. And uh I was like, man, before uh before I hit 40, I want to shoot under par. And I've taken the opposite where I'm like, now I need to practice. Now I want to like achieve this thing. But and we were just talking earlier. Um I find it very difficult because I find that business has become that competitive thing for me. Um, I for the longest time after I retired from swimming, I couldn't compete. I didn't know how to compete in the business world. Um it took some like I I don't know what it was. I had some mentors that had to like help me through it, but like I just business is one of those things where there's there's no rules, there's no, you know, other than doing right or wrong, right? There's morally, but there's no rules, there's no start, there's no finish, there's no end game, there's no winner, loser, like it's an infinite game, as Simon Sinek would say. Um, and I just I didn't know how to compete. And then when I learned, okay, this is how I'm gonna compete in business, yeah. I have not worked out. I it's so hard for me to get back into the workout thing because I just want to spend all my time in the office. And as someone who literally just had a child, you know, it's two months old, it's fantastic. I want to be around when, you know, and I want to, like we were talking about, I want to be able to compete with my kids and I want to be able to stay in shape. And but trying to make that like mental shift from from business back to sports is it's been really interesting and challenging.

SPEAKER_00 18:03

Yeah, I I I I agree. Um, my business is different than yours in some ways because um I mean, yours is more of a competitive business. Like you're getting client, you're not getting client. You're you know, you've got to generate revenue. And and I do too. I mean, we've got wins and losses, like the chamber definitely has that. But um I think for me, it's a lot about collegiality and team building. And I mean, for me, winning, I think the chamber winning, yes, of course, membership is great and great events is important, but like overall the the collegiality of how Windsor Essex is uh doing is really, really important to me. Um, so for me, it's kind of like I'm the team player, like I'm the team captain. That's how kind of that's kind of the feeling that I have. Yeah, and our team is trying to compete. Like this is very much a hockey.

SPEAKER_03 18:52

I was gonna say it's very similar to what you're doing.

SPEAKER_00 18:54

As opposed to a swimming analogy.

SPEAKER_03 18:55

It's very similar to what you were trying to do as the NHL or something.

SPEAKER_00 18:58

You got it, right? Like, I'm not going to be the star player, and I don't know the star players in our community. Maybe that's the mayor. I mean, you know, maybe that's our elected official. I don't know, whoever that is, but like it takes a bunch of people working together for a hockey team to win, just like I think it takes a lot of people working together for a region and economy to win. And if I'm one of the leaders of that economy, that's where I'm proud to be, and I think that's my role right now. Um, and that makes me I want to win for the region, right? Like I think that's important. Whereas swimming was I want to win. Like as much as swimming is said to be a team sport, it's not, it's an individual sport, right? Like it's you win, other people lose, go as fast as you possibly can, and everybody else deal with it. Right. Um business for me in my role is not that at all. It's how do we win? And I don't know who we're competing against, but I do know that um, you know, again, this is probably just my upbringing, growing up in the community, my dad having a business, and like, you know, just all of the things that have gone into making me who I am. Yeah, that's kind of shaped what my driving force is now is how do we like the competitive thing is how do we win? Right. And being a letterer or assistant captain or captain on the team.

SPEAKER_03 20:11

Okay, so you say you're so uh let's talk a little bit about um because I think it'll come full circle, but so your dad had a business. Did yeah. So let's talk a little bit about what business it was. Sure. Um, what lessons he maybe instilled from you growing up with a father who was very entrepreneurial, obviously. Yeah. Um, and then how you came to get into the role you are in today as president of the chamber.

SPEAKER_00 20:39

Yeah. Um, so my dad, uh, when we moved down here, he opened a business called Crossings Menswear. So it was at the mall. So it was part of a chain uh kind of throughout Ontario, but he had a menswear store in the mall. And um like a lot of hours, worked a lot of hours, right? Because just like all of our folks that are members or people you know, like the hour that you're spending working on the floor is an hour you're not spending paying somebody else. Yeah, right. So that really is important for him because at the end of the day, his bonus and his salary and all this stuff was tied to profitability, right? So um I think what I learned from him as it relates to being a small business owner uh is you know how deaf uh life-defining challenging it is, right? It it he wasn't at all the events, and every boxing day when our family got together at Christmas, like that's when he was at the mall, right? So um the commitment to allowing, and this is what I want to do for my family is I never hurt for anything. Did we always have the most money? No, like but there was never a question whether or not I could play triple A hockey or be a swimmer, or like I had every single opportunity. Um and I realized that it was at the expense of maybe not going to watch my hockey game, but maybe he was at work so I could go to that hockey game or that tournament out of town, right? So So that was that was um you know pretty important life reflection at this point, uh especially now as I have five and seven-year-old boys. So what can I do now to allow them to have the same opportunity, opportunities that I have?

SPEAKER_02 22:13

Yeah.

SPEAKER_00 22:14

And you know, my gig I'm not gonna get rich in. Like it's it, I'm a leader of a not-for-profit in our community. It's it's not, you know, it's got more status than it does dollars coming in, and and that's fine because that's the life I signed up for, and I absolutely love it. And again, that's not my win, and that's not what I compete at. Um, so that that's that's kind of one of life lessons I learned. But but also, you know, my mom was in sales. So my mom worked for Morton Wholesale, and my mom worked um for um Hershey's, so it's a sales rep.

SPEAKER_02 22:44

Okay.

SPEAKER_00 22:44

So we were the we were the family that always had chocolate. So, like, if people are like, hey, do you like chocolate or like Easter? You know, you know those Easter eggs of like um I don't know what they're called, but they're like eggies, I think they're called. So the minute that Easter was done, eggies would not sell. Like they'd pull them off the shelf. So the day after Easter, I would have a wall of cases of eggies at my house. And I hate the things now because for me, they were just they're everywhere all the time. So I don't know how the heck this goes back to the question you asked, but uh but maybe that's I mean, I know my my mom was very competitive, my dad was very competitive, played high-level sports. But um, how does that segue into what I'm doing now? Um, well, I played for the Spitfires, the captain of Spitfires here, uh, met a girl from Bell River, we got married, I wanted to settle here. This is my home. I I love Windsor Essex. Um, went to school here, did both my undergrad, my grad school here, um, started working for the university, started promoting the business school because I was working for the business of the NBA program at the time. So I was promoting Windsor Essex as a place to live, do business, you know, especially young professionals. So that's kind of how I got into that. I was part of the Windsor National Film Festival. So I was in the arts community a little bit. I of course had the sports background. And then uh it was it was kind of interesting. I've actually said it publicly before, but um, Drew Dilkins was talking about how in 2018 the General Motors plant was leaving in Oshawa, like that was basically disbanding. And uh, he called out for economic diversification in our community and and what that meant and how it you know made sure that our our community and economy would still moving forward. And I remember listening to that speech. I'm like, I've sold this region on a whole bunch of different platforms for a lot of years, whether it's recruiting for sports or recruiting for hockey or the NBA or I said, I can do this. Like I know I love this community, I know everything about it, like or a lot of things about it. Yeah, and I want to tell everybody else how great it is. And I want businesses to come here because that's that they should do well and Windsor should do. And I'm going back to this whole thing winning as a team. Um, so I did uh investment attraction for Invest Windsor Essex. So I foreign direct investment, traveled the world, said, Hey, come to Windsor. This is a great place to be. So I did that for a couple of years and then um had the opportunity to go and work at the municipal level for Lakeshore, municipality of Lakeshore. And uh, I'd like to say I learned how the sausage is made from the development side of things. Like municipal government has such an impact on our daily lives, and people don't understand that. Yeah, like it really does. It impacts much more than your the provincial or federal levels. Yeah. Um, so it was wonderful to learn what that was like. So I did that for four years, built some profile through there, learned planning, learned economic development, learned, you know, the challenges of building, starting, doing a business, working with solo entrepreneurs, small businesses, just development in general. And then uh this this opportunity came up uh with the chamber. And I said, you know, I've been doing it in a whole bunch of different capacities, and now I get the opportunity to represent our region and our businesses, business community, um, and try to win as a collective because I do believe that, you know, especially as it relates to Windsor, is we have to do well together. Like all tides uh raise all boats, as opposed to us working against each other. So I, you know, I'll call myself a coach or a captain or you know, a general manager of of the business community here, and trying to make sure that our team, and I say team, like our regional economy is winning. And that's kind of what I feel my task is these days. Right.

SPEAKER_03 26:22

That's super interesting. Um, and it man, our our lives are almost they're very similar, maybe different sports, different regions. But I mean, you know, my dad had me at 40, yours was you said 39, you know, grew up very similar, um, never had to worry about money. But I so a couple things that you said there. So did you always feel that your dad was working so that you could do things, or was there a period of time where you felt a little left out that he wasn't at those things? Because I had that experience. I don't think it was until I was probably I think from maybe 15 to 17, I was always like, man, my mom's always there, my dad's not there, my dad's never there, my dad's never there. And until I was probably 17 or 18, I never made the correlation of like, man, my dad's in sales. Yeah, he's always at boxing day sales, he's always at holiday sales, and that's where most families got their holidays, and my dad was always the guy working.

SPEAKER_00 27:23

Yeah. Um, yeah, I've you know, I didn't really try to make that connection. Um if I think of like who drove me to practices and was at games, you know, my dad made it absolutely as much as possible, and especially as I was, you know, now playing pro and like he would be the guy that would drive up to Oshawa if we were playing on a Thursday night. Like, so um he made the effort as much as he possibly could. Um, so I'd say in that capacity, like, did I feel that he was working and wasn't there? No, not at all, honestly. Like, I I think it was um, you know, he was the one that drove me to swimming practice before school, right? Like he would sleep in the van or watch me, whatever. I mean, I was in the pool, so it didn't really matter, but yeah, um it's it's fascinating to put it like that. But no, you know what? And the other thing, like, did I ever um I never had to worry about money because I always had the opportunity to do what I needed to do. Right. Did my parents? I'm sure they did. Yeah, you know, like it wasn't like a thriving business that went multinational. It was a you know, you gotta you gotta work hard every single day. Yeah, so um I probably learned a lot of skills and um work ethic and determination through that. So what did your what did your parents do?

SPEAKER_03 28:39

So my dad was in sales, yeah. Uh he worked for uh the Alberta government for a period of time when I was a kid, and then it went from whatever, it went from um, you know, Ford. He sold cars for probably six or seven years. He was at Leon's doing furniture and everything for a few more years, um, Staples for a long time. Uh he ended his career at um um sleep country, okay. Uh, which is actually uh I so I had I did seven years in financial services. I took a one-year hiatus to work at Sleep Country. Um so what ended up happening was my um the the guy who was teaching me financial services had moved here to Windsor. Uh, and so I felt like the guy that was mentoring me was kind of gone. I wasn't sure if this was for me. Yeah. Financial services is really the only thing I've ever known. I've had some tiny little jobs for here and there, but as a swimmer in our swim schedules, you know that like you can't have a job for three hours in the middle of the day. Like it's just not gonna happen, right? So um financial services is really all I've known.

SPEAKER_00 29:42

Yeah.

SPEAKER_03 29:42

Um, and I just wasn't I loved helping people, I loved solving problems. I just didn't know if it was the career for me. Yeah.

SPEAKER_00 29:50

Um which is tough because financial services, like if you're getting into it, you're not getting into it to make rich, to be rich immediately. No, like I mean it's a long-term game, it's a long game, yeah, relationships and and keeping people with you and building credibility and trust and like um you know, life planning with people. Like that's it's not something that you can do and walk in year one and make bank and just say thanks, that was great. Like, yeah, you gotta be invested for long haul.

SPEAKER_03 30:17

Big time and people, and some of your yeah, and some of your clients become some of your best friends because you have have had them for so long and you've their kid, if your kids are playing with their kids, and it's actually amazing the relationships that come from it. Um, but I was living with my uncle who um ended up uh committing suicide. Uh sorry to hear that. I was one who found them, so it was a pretty tough uh couple months there. Sorry. Uh I decided that I was just gonna pack up my life and and move. I wanted to change, get out of Calgary, um, and I got back into financial services here. Um, which How'd you pick Windsor? Uh so the gentleman that was teaching me the business had moved here. So he came here, I want to say, to uh I want to say mid-2015. Okay. Um his spouse is originally from Kingsville, so they came out here to like, you know, see family, whatever. And he was like, man, like Detroit's across the river. Uh at that time, real estate prices were really fantastic, especially coming from Calgary, extremely low. Um, and so he ended up settling here and he started growing the office. And he's like, Man, I got so many people, I don't know what to do with them, I can't train them all. So we were having conversations for like eight or nine months before my uncle took his life. And once he took his life, I, you know, kind of disconnected for a few weeks and just kind of got my stuff right. And I'm like, okay, do I love what I'm doing at Sleep Country right now? You know, I spent seven years helping people put money back in their pocket. And now I've been basically trying to sell something and take money out of their pocket. And I just couldn't, I couldn't see myself doing that for the rest of my life. Yeah. And I was like, man, I do love financial services. I do want to help people, I do want to give back, I do want to do all these things. And if I was gonna do it, I wanted to do it with the person that taught me the business. Yeah. So I literally just, you know, I worked as much as I could for three months, uh, saved up as much money as I physically could and literally packed up my car and drove, drove here. I was here within like 34 hours or something like that. I started work the next day. Like I went right to the office and I was at the work the next day. And and it's funny that you so coming back to what you said earlier about Windsor, it's amazing to me since I've been here. So I've been here since October 1st of 2017. Yeah. So call it almost eight years.

SPEAKER_02 32:33

So yeah.

SPEAKER_03 32:34

Uh, how many people don't know the amazing things that are going on in Windsor? Like so many people think I I've heard the joke that you know, Windsor's the armpit of Ontario or whatever. Um, but so many people ask me why I move here and they just don't know how great it is. It's amazing. It's amazing.

SPEAKER_00 32:54

It's amazing.

SPEAKER_03 32:55

Best weather, Detroit's right there. Yeah, growing businesses, um, you know, small town feel. Yeah, if you really want the big city, you can go across the river. You can do anything you want here. Except climb a mountain. Travel's great, can't climb a mountain. You can't climb a mountain. It's if you want to climb a mountain, I guess. Um, I never actually did too much of that, but my wife and I went out, our first trip together was out to Alberta to see my family, and we went to Banff, and she that's all she wanted to do was hike. Yeah, and I had never hiked them, so it was it was neat.

SPEAKER_00 33:21

It was kind of cool. Yeah, yeah. You can't climb mountains, you can't down hill ski. Yeah. Pretty much the rest. I wasn't a winter sport guy, so skipping is not my thing. Yeah, we were indoors, swimming in pools. Yeah. I think the thing that you hit on there that that I I teach at the university a little bit too, and you know, I love mentoring, and it's a huge thing and part of my life. But I mean, sales are extremely important. Stay everything is sales. You're selling something at any time. But the thing that you have to understand is you have to love the product that you're selling. And for me, and this is you know, no disrespect to my first job out of school, is I was working for Stellantis, um, and I was in the marketing team. So at the end of the day, like I'm selling vehicles, like I'm broadly selling vehicles to the public, right? I didn't care. Like I didn't care about selling that product. And then my next job, I went and worked back at the Odette MBA program at the University of Windsor, and I had the opportunity to sell a program that I absolutely loved and changed my life. Right. So at that point, I'm like, oh, I love sales. I didn't realize I loved it, but I love selling things that I believe in. And it sounds like you have to sell things you believe in. And I think that is an extremely important message to anybody that's out there. Um if you're gonna sell something, you gotta believe in what you're selling. And that's helped guide me in my decision making as my career progressed because I know the things that I'm working on or the organizations I'm with or leading now, I can sell what we're doing, and I believe in it. And then you can sell with conviction and you can, and then it doesn't become selling, it's just talking about the things that you're doing and you're inviting people to be part of it. So I think that's extremely important.

SPEAKER_03 34:54

Yeah, I mean, I would I would agree, uh, especially the fact that like everything is selling. Everything's selling, right? Whether it's you're selling an idea, you're selling an idea, selling yourself, selling your friends to go to a movie with you, selling that girl as to why she should go on a date with you. Like everything in life is selling. Terrible salesperson. I can't I just I can't understand. And I guess it's maybe just my brain's broken, but just you know, like so many people, they they hate selling, but it's in everything we do. Everything you do.

SPEAKER_00 35:22

And I I I tell my MBA students that I'm like, look, this is not a sales class, like this corporate consulting. But I'm like, you're selling something every single day. Yeah, like you're going to go to your boss and you say, I think we should do this. Well, you have to convince that person why you should do that, or you know, a direction you want to take the company. Like, okay, great, but why? Like understand what the the value proposition is on whatever you're pitching, and then make sure that you've refine that ask and then make that ask, and you'll either succeed or not.

SPEAKER_03 35:53

Right.

SPEAKER_00 35:53

Right. And that's that's to me like that's where my competition comes in. Like there's still wins and losses, they're just different wins and losses, and they're maybe not quite as measurable quantitatively, but there's wins and losses every single day for me. And I love that. That's important to me. Right.

SPEAKER_03 36:08

Yeah, because you're in a whole different sector of things, right? You're dealing with companies and you're dealing with uh, you know, international businesses coming into the city, you're dealing with a little bit with everything, right?

SPEAKER_00 36:21

Government officials, politics, not for profits, committees, stakeholders. Like it's it's kind of this mix mash of like where my job is. Um, and I'm learning what it is and where it where I need to take it and what I need to focus more on and less on. And um, but it's fascinating. I'm I'm now about six months in, and um, it's been a roller coaster. Yeah, that throw tariffs in the mix too. And before you know it, I've had like 90 media interviews from outlets all over the globe.

SPEAKER_03 36:50

Um, so it's it's been yeah, we're in we're in a really weird time right now with with Trump at the helm in the US and just the constant, you know, tweet here, tweet there, change, change this day, next day it's different. And there's very, you know, in our business we say volatility. It's just very unknown what's gonna happen. Um, and you're most people are typically used to having just a consistent message, constantly the same all the time. And now it's like every day is different.

SPEAKER_00 37:19

Every day is different. Um, you know, I I learned very early that I should always have a suit and tie in my office because I don't know what's gonna be said and I don't know what I'm gonna get a call from media on or which interview I've got to do or who which person that I need to go speak with.

SPEAKER_03 37:34

So um that just gotta be an interesting ambiguity is I I love ambiguity though.

SPEAKER_00 37:41

Like that to me, that's important. Like, um, I don't want to wake up in the morning and know exactly how the day's gonna go. I get that. I I can't like to like I know where I'm supposed to be and what I'm supposed to do, but yeah.

SPEAKER_03 37:52

That's what I love about my job being the fact that whether you're taking somebody out for lunch or meeting somebody for the first time or meeting somebody you've had as a client for 10 years or whatever, like every day is different. I don't know if I'm gonna be on calls all day or in business meetings, developing our our systems and processes. Like every day is different, um, which brings a lot of like fun into the mix.

SPEAKER_00 38:16

Yeah. And and at some point you probably sat down and said, Is this something that I want to do for the rest of my life? Like I knew that I would never be able to go sit in a padded room.

SPEAKER_03 38:24

Um which we're in right now.

SPEAKER_00 38:26

Which we're in right now. Um, and like pound on a keyboard all day long or data entry, or like I just I knew that I needed to be out doing things active in the community. Um, and yes, I do I actually I love doing data. Like I love sitting and doing Excel spreadsheets and figuring, like it's kind of weird that I've learned that I love that, but I do, but um, it can't be my day. Yeah. So it's gotta be this, it's gotta have conversations.

SPEAKER_03 38:52

Okay, so let's um let's pivot a little. Sure. What do you think? I asked uh I asked somebody earlier about this. What do you think are two lessons that you uh wish you would have learned sooner in the business slash mentality slash whatever, you know, um getting through life. What do you wish you could have learned sooner that maybe the people watching could take and learn from and implement in their life before it's too late?

SPEAKER_00 39:27

Two lessons that I've learned over my years that I can translate to other people or have I mean, I think we've talked about one already, and that's sales is everything. You will be selling something, whether it's an idea or like a a product or like and endorsing that and loving that and not being afraid of selling things, like I think is extremely important because it will it's part of business, it's part of life. Like so I know I'm going back to something, so definitely sales. Um the other thing that I think I mean I've always kind of known, but is really um really been important to where I'm at now is how important relationships are and um making sure that you're approachable, easy to get along with. Um, I mean, maybe it's just the nature of where I'm at and who I am, but like don't be afraid to put yourself out there and share your opinions, but also be respectful of the person's opinion you're getting back, and they're not always gonna align, right? Yeah.

SPEAKER_03 40:35

Um, but it's I think is missing a lot in today, right now. It's like if you have an opinion that differs, one of us has to be right, one of us has to be wrong. And I'm a very big believer, I'm assuming you're gonna say this is that there is no right or wrong. I tell my clients. Anytime somebody comes to me and says it's about perspective. Any yeah, anytime my clients come to me or somebody at prospect comes to me and says, Well, like what's the right thing to do? There is no right thing to do. It's what are your goals? What are you trying to achieve? What things are gonna get you to that point, yeah, and what works for you. There is no right or wrong, it's what's the thing for me, yeah.

SPEAKER_00 41:16

And um I mean, when you think about right or wrong, and this kind of ties back to our whole conversation today, is like it's kind of weird where you try to place competitiveness in that mix too, because we're both competitive people and we both like to win and lose. And if you think about your perspective or your idea versus my idea, it doesn't have to be against each other. Like your idea can't win and my can't lose. Um, there can be both wins, right? Like, and I think it's it's kind of this weird life lesson that you're gonna have to learn at some point, especially if you're an ultra competitive young kid like we were. Like you're not always gonna win, they're not always gonna win, but you try to find situations where you can both win, right? Right, and that's where I think I found this career path and journey for me is I'm trying to make everybody win. Like that that is the cool thing, and the losses are group losses, and it's like it's it's a collective loss as opposed to a individual loss. Um, yeah, we might have a key member decide that they want to work with us anymore, and that'll be a loss for the business or the organization. But um, if we're continuing to push the collective good up, then I think it can be communal wins. And and and I don't know how this exact ties back to the whole, you know, relationships matter, but I think they do. And I think if you understand the perspective of what you're looking for or, you know, other folks around here are looking for, I think that's when we can figure out ways that we can all collectively win. And I think that's part of the role of where the chamber fits. Kind of that nexus of like business. What does business need to win? What does government need to win? What does the not-for-profit space need to win? And then how does the chamber, my job, kind of bring all these together as the nexus between those and say, well, business needs this, municipalities need this, not for profit space needs this. How do we all kind of do this?

SPEAKER_03 43:16

Right, right.

SPEAKER_00 43:16

And I think that's where I want to take the chamber. Okay, and I think that's where it's been, but I think that's where I'm gonna try to elevate it.

SPEAKER_03 43:23

Yeah.

SPEAKER_00 43:23

Because if we're all doing well, the whole region's winning. You got more money in your pocket. Yeah, I got more money. Well, I don't, but people have more money than I'm an offer profit space, right? We'll help you with that.

SPEAKER_03 43:36

Don't worry about it.

SPEAKER_00 43:36

There you go. Uh, they've got more money in their pockets. Um, the whole region's doing better, and like, you know, we're we're changing, we're shifting perspectives and mentalities, right? And you know, do I think two years, five years, ten years that people go and look, oh my god, look at Windsor, Essex. That is the place to live in the world. No, maybe not, but convinced I mean, for you, you love it.

SPEAKER_03 43:58

And before you know it, I would never have thought. Of it. No, to be honest. No. And it's been amazing. I mean, you know, met my wife obviously, met great clients, my business partner, like everything has just continued to flourish. It's it's just amazing. I think the area is fantastic. It really is. Everybody wants to help everybody. I do feel, you know, this is a very, you know, it's it's a sizable community, let's say, but you know, it's got that very small town feel. Everybody's trying to help everybody win. It really is.

SPEAKER_00 44:28

You get 500,000 people in Windsor Essex. Yeah. Right. And like we're on this little peninsula down here. And um, it's gonna be interesting to see where this all goes, especially as um, you know, what we thought was our best friend across the border, um, that relationship changing potentially permanently, who knows?

SPEAKER_01 44:44

Yep.

SPEAKER_00 44:45

Um, you know, and you said it earlier, some of the best parts about Windsor is the fact that we do have relationships with Detroit, and you can go do those things. So, you know, that's the other element of of what my job is. I I want to keep those relationships going, right? We have to maintain that we can't sell our house. Like Windsor's here, Detroit's there. We're not selling our property. Like this is where we're gonna be. So how do we make sure that that relationship, even if it's just Windsor, Essex and Detroit, how do those stay together? I think is a pretty important thing.

SPEAKER_03 45:14

Right. Okay. Uh last two questions. Sure. First one being we talked about two things uh two two lessons people could learn. What are what what would you say is one or two things outside of the sales and the relationship that you learned that got you to where you are today? Things that got me to where um like without those things, without learning those lessons, you wouldn't be the Ryan Donnelly of today.

SPEAKER_00 45:51

Yeah, I think the uh one of the things that I learned is not everything's in your control, right? Like you can't control everything. That's a good one. Um and I and I say that because like my hockey career was ended. I made the decision at the end of the day to walk away from it. I could have come back and risk my life potentially. Um, but that was a little outside my control. And then as a result, it's important that you can um you don't have to be pigeonholed into one thing, right? And you can change and you can grow and you can evolve and you need to. So I think that is extremely important. Like if you look at, I mean, the the the best decision that I made was going do my MBA program at U at Windsor. And and I say that for a couple reasons. It's not because I went and learned business more. Up until that point in my life, I had always been, you know, from 12 years old on when I said I'm gonna be a hockey player. I was a hockey player, yeah. That like everybody knew me. I looked like a hockey player, I wore I had hockey hair, like I was a hockey player, right? Um, and then I recreated myself that year, even doing my undergrad. I was a hockey coach. I was doing everything was hockey, and business was secondary. So I made a conscious shift that I'm gonna evolve, I'm gonna change, and I'm gonna be a business person that used to play hockey. Right. As opposed to a hockey player that's learning business. And that mindset shift changed the traject trajectory of life. And to the point now that a lot of people have no idea that I played hockey. Some do, like the the amount of people that I come across and they go, like, you look familiar, and like with the Chamber of Commerce.

SPEAKER_01 47:26

Yeah.

SPEAKER_00 47:27

And they're I'm like, I know why they're saying you look familiar. Yeah, because they're used to watch me playing with Spitfires. Like, and I know that, but I don't lead with that. That's the last thing I do.

SPEAKER_02 47:35

Right.

SPEAKER_00 47:36

I mean, I was at a meeting this morning with uh person I'd never met before, and up until 10 minutes before the conversation ended, he had no idea that I played for the Spitzer as the captain. And that's great because that's former Ryan. Like, yeah, so the I mean the life lesson helped me get to where I am is um, you know, life is full of like inflection points where you're either going to change or it's gonna be forced for you to change. And then how are you gonna endorse and adapt to that? Yeah, because if I would have said at 25 years old when my hockey career was done that I'm hockey Ryan, I will always be hockey Ryan. Right now, I would probably be an assistant coach in some league in the middle of America and probably not. Oh, I wouldn't have married my wife, I wouldn't have these kids, and life would have been completely different, and I would have been bouncing around every two to three years for the rest of my life. Yeah, and that's great if that's the direction that I want it to be. Yeah, but I pulled myself out of that and said, that can't be me forever. Right. And I think that's one of the things that, you know, going back to my parents at the beginning is my mom always said, Ryan, I don't care if you make the NHL, like I don't care if you make $50 million. Like you have to get a degree at some point or diploma. She said, but did it get a degree? Because she knew that if if I I was only ever that person, I would have missed out on a lot of parts of life.

SPEAKER_02 48:54

Yeah.

SPEAKER_00 48:54

Right?

unknown 48:55

Yeah.

SPEAKER_00 48:56

Like hockey's different because you could have made a financial career that I would have never had to work again. Sure. But then I would never have the opportunity to live a full life that is beyond the hockey rank and beyond that. Right. So I think that's extremely important.

SPEAKER_03 49:09

It's and it's really funny you tell that story because I had seen you andor, you know, talked in passing a few times at different chamber events. And it wasn't until we started launching the charity poker tournament next year that I reached out to one of my friends and I was like, hey, Adam, like, you know, who can you introduce me to? And he reached out to you. Yeah. And your response was, yeah, I'm actually, I've I know them. And I'm like, I did not put the two and two together. And and it's funny because I yeah, I was a Flames fan and I watched the whole draft. Like, and I didn't even put the two and two together, right? So it's pretty funny.

SPEAKER_00 49:46

So yeah, me and Dion Finuef, uh Tim Ramholt was that year.

SPEAKER_03 49:50

Man, Finuf. I went to school Finuf. Oh, yeah? Yeah, Hunting Hills High School, Red Deer. He was a Red Deer Rebel. Yeah, we can chat about him after. Off off camera. Sure. Um, yeah, opinions might differ after off camera, maybe. Um last question. Sure. Uh we end the podcast uh with the same question to everybody. Okay. What does success mean to Ryan Donnelly?

SPEAKER_00 50:14

Ooh.

SPEAKER_03 50:15

Like what like any any parameters around that? No. Some people say it's relationship, some people have said it's yeah, money, some whatever.

SPEAKER_00 50:24

It's not money. Um I mean, money, money matters, of course. Like, I I want to have the opportunity for my family to live the life that they want to live, but that's not they don't want to live on yachts, like they don't want birkenbags, like that's not my family. Um success. I want to live in a community and I want like I'd say impact is more important than for me. Um like at the end of the at the end when it's all said and done, um, what are you remembered for? Right? And that's that to me, like if I think of that lens, I don't know what that'll be, and I don't know what I'll be remembered for. But to me, I think, especially now in my current career, is what positive impact have I left and you know, what does that mean for my family and future generations in our community? Because I I'd love for it to be this community. Like, I'm not saying I want to put my names on buildings, but I want people to think about oh, he did this, or you know, his family did this or his organization did this, and this is what it resulted in. Right. Um, so I guess you know, legacy to a degree, um you know, a combination of legacy, impact, um, and and collegiality and fun and enjoying myself. Like, for folks that know me, like I'm a serious guy, but I'm laughing all day long. So I need to smile every single day. And I think that's extremely important. So um, if I can smile every day and get the people around me smiling every day, that's a that's pretty impactful and that's successful for me. That's a win. Yeah.

SPEAKER_03 52:06

That's awesome.

SPEAKER_00 52:07

It's a win.

SPEAKER_03 52:08

Cool. Well, Ryan, thanks for taking the time uh to chat on the success uh podcast here. And hopefully we'll get you on another time. Thank you. That was great. Thanks.