Joe Conlon Team: Windsor Real Estate Tips & Stories
The Joe Conlon team is one of Windsor most active in real estate — and in this episode, team members join Scott Dillingham to share insights from the local market and what buyers and investors should know right now. The team (six agents, four admins) promotes fun dynamics, social…
The Joe Conlon team is one of Windsor most active in real estate — and in this episode, team members join Scott Dillingham to share insights from the local market and what buyers and investors should know right now.
The team (six agents, four admins) promotes fun dynamics, social media contests (e.g., Nintendo Switch, Cedar Point tickets), and proactive tips: avoid overbidding, pre-inspections. Amid 2025's Windsor outlook (CMHC forecasts modest growth with averages ~$600K, border reopening/hospital boosting affordability post-BoC cuts to 2.25%), they highlight Windsor's value (most affordable city) and opportunities (e.g., Walkerville office in historic house). Funny anecdotes include Joe's back-flip fail/head crack. This episode offers relatable insights for buyers/sellers navigating 2025's competitive scene (rents up 4-6% YoY per Rentals.ca), motivating with stories of teamwork and market savvy.
Guest Bio
Jill Wingler and Steve Popovich are agents with the Joe Conlon Real Estate Team at Royal LePage Binder Real Estate in Windsor, Ontario—a top 1% team nationally. Jill, a former teacher, specializes in families/east end areas (Tecumseh/Lakeshore/Belle River), drawing from her Windsor upbringing. Steve, a former musician (Canadian Idol top 40), focuses on first-time buyers/downsizers, leveraging people skills from touring/bartending. The team emphasizes education, speed, and fun marketing. Connect at realtorsforlife.ca, on Facebook at facebook.com/joeconlonrealtor, Instagram @joeconlonrealtor, or call 519-735-7222 for Windsor-Essex services.
Key Takeaways
- Jill's path: From teaching in London to joining Joe (sister's ex, funny clover car stories)—highlights family focus, market education to avoid emotional overbidding.
- Steve's background: Saskatchewan musician to Windsor realtor—recruited by Joe's "door kick" for hustle; enjoys buyer/downsizer niches.
- Team structure: Six agents (jacks-of-all-trades), four admins—fun dynamic, social contests (Switch/Cedar Point), Walkerville office nod to Joe's roots.
- Market tips: Speed essential in 2025's fast sales (3-4 days)—pre-inspections, level-headed offers; Windsor remains affordable amid border reopening/hospital growth.
- Funny moments: Joe's back-flip hotel fail/head crack—team trips build bonds.
- 2025 outlook: CMHC predicts stability (averages ~$600K), BoC cuts (2.25%) easing—opportunities in east end/Walkerville.
- Advice: Buyers—education first; sellers—leverage team for wins in bids.
- Universal: Relationships key; proactive planning beats reactive regrets.
- (00:09) - Welcome and Introduction
- (03:17) - Jill's Journey to Real Estate
- (07:11) - Transition to Steve
- (11:17) - Steve's Musical Background
- (12:54) - Naked News Experience
- (16:12) - Tips for Buyers in a Competitive Market
- (16:55) - Conclusion and Contact Information
Transcript
Introduction
Welcome to the Wisdom Lifestyle Money Show. I'm your host, Scott Dillingham. The show is designed to help Canadians invest better in Canada and the United States. We are the North America-based mortgage financing lender and provide education to both countries.
Discover how you can become a better investor and access the financing you need. Okay, welcome back to the show.
Today, I'm really excited. I have Jill and Steve from the Joe Conlon Real Estate Team who were top 1% in Canada with Royal LePage. So today we have Jill who's going to chat first.
So welcome, Joe. Thank you.
The Core Idea
Yeah, no worries. So how's it going today?
Good. Very good. Well, I'm so glad you came. And I know before the show, we were talking about some of your story and how you got started into real estate.
And I'd like to hear, tell me about your childhood. How was it when you were a child? You wanted to be a realtor or what were your dreams when you were little? Growing up, I grew up in Windsor.
My family moved almost every two to three years. So I really have lived across Windsor-Essex. But no, I did not always want to be a real estate agent. In fact, I wanted to be a teacher.
Deep Dive
Okay. So I did go to the University of Windsor to become a teacher and taught for about seven years. Moved out to Vancouver, taught at a private school in Vancouver, moved to London and taught there for about six years.
That's awesome. Did you teach?
Kindergarten. Okay.
Grade four, grade six primarily. That's awesome.
Practical Steps
Good for you. Yeah, yeah. It was great until we decided that we were going to move back home. My husband and my two children and I, which was fantastic.
I'm loving being back in the Windsor-Essex area. No, that's awesome. So then from teaching, how did you get into being a realtor? Something that I think I always really enjoyed.
Just everything about home and the different styles of homes and just predominantly helping people. So yeah, I decided to start taking my real estate courses while I was on mat leave with my daughter and contacted Joe because I knew him back when he was 18 years old.
Okay. So how did you know Joe when you were 18?
Key Takeaways
That's cool. Can you tell me about that? He dated my middle sister, Jeff.
Nice. So I ended up giving him a shout just to pick his brain about the industry and where to get started and help along the way.
No, that's incredible. That's funny. So then you must know some embarrassing stories about him.
A few. Would you be able to share one without getting into trouble?
Resources
Would you go back? Joe. He often showed up to our house in a green car with a four-leaf clover on the hood wearing a poncho.
Nice. So that was his lucky car, I'm sure. His lucky car and somehow the luck stuck.
There you go. What did your sister say when he would come to the house in this green?
Oh, she didn't mind. I think my dad cared more.
Introduction
No, that's cool. So from the lucky car, you're now on his team.
So how did that happen? Yeah. When I got into real estate and moved back, obviously I'd been talking to Joe along the way, knowing somebody in the industry was helpful. And that was right around the time that his workload became greater and he needed the help.
So that's when he decided to start the team and asked me to be a part of it. Oh, that's awesome. So what do you do for the team specifically? Basically anything from showing houses, selling real estate, team meetings, helping with marketing and...
Nice. That's awesome. Do you guys have like dedicated positions or does everybody like do the same thing?
The Core Idea
Just... Most of us all do the same thing, I would say.
Yep. Yep.
Okay. No, that's cool. And then how is he to work with?
We see him. He's a friendly guy.
Deep Dive
Good looking. How is he to work for?
Same friendly guy. Very easy going.
Yeah. We have a really great dynamic. Our team is a lot of fun.
No, that's great. So then with real estate, it's a crazy market.
Practical Steps
You have to be aggressive. There's bidding wars and things like that. And I know you guys are really good at winning those.
So what do you do? What are the tips that you would share with some clients when they're putting in offers? Not to get too over your head. Try to stay level-headed throughout the whole process.
Making sure that you find the right house that's for you. We... You might lose some, but we'd rather see our clients lose than overbid and get too emotional in the process.
No, that's true. So is there some preferred areas that you guys like in this city that someone listening might be up and coming that maybe they want to purchase in or?
Key Takeaways
Walkerville. Walkerville's at...
Right where our office is. Yeah.
So that is true. You guys have a house right in Walkerville.
It's a beautiful place. How did that come to be? Joe was thinking about buying a place and kind of stumbled across this cute house in Walkerville and he's following in his mom's footsteps.
Resources
That's awesome. So his mom used to live in Walkerville? His mom still lives in Walkerville and owns a business in Walkerville as well.
Nice. No, that's so cool. Can you tell me something that I wouldn't know about the Windsor market or something that's interesting or rewarding on your end? You know, someone, a client or myself listening would not be aware of.
Still, that we, even though it seems like our prices have been skyrocketing over the last couple of years, that we're still the most affordable city to live in. And all of these great things that are happening. And hopefully once the border opens up next month, we'll be able to use the Detroit amenities again and the new hospital coming. I think there's big things happening here in Windsor.
I agree. Now, do you find like the border being closed, do you find that has affected real estate at all?
Introduction
No. No?
I haven't personally noticed that. Okay.
No, that's good. For me, I can't say that I have noticed it so much, but I know because the people that work there can still travel. So I find that has Buzz Curious on your end.
No, that's cool. So I see you guys are very active on social media and you guys often have contests, really cool contests and giveaways. Who usually picks up those prizes?
The Core Idea
Our admin staff. Yeah. What was the craziest prize you guys gave away so far?
Guys, craziest prize? Cedar Point ticket? Nintendo Switch was a big one. A lot of people love that one.
Okay. That is a big one.
Yeah. Give away your hood.
Deep Dive
Yeah. Give away. But it's got to be a green car.
He's got the hood. He took the hood right off the car.
That's awesome. So you still have it in the basement of the house.
That's so funny. So Jill, if you had to say your niche, like your number one focus for when you're working with buyers or sellers, what would that be?
Practical Steps
I would say predominantly families. I feel like I can relate best to families, understanding what it's like to move with two young children.
Yeah. And they're done that. So yeah, I would say that and the East End. I grew up, a big chunk of my life was in Bell River.
I went to Bell River High School. I had a lot of friends in Tecumseh.
I live in Tecumseh now. So I feel like that East End, Lakeshore area is what I know best.
Key Takeaways
Oh, that's awesome. Now, this is a random question. But so you mentioned you when you were little, you moved every two years. Do you do the same thing with your family?
I haven't. We bought our first house. I lived in it for five years. And we're coming on four years in our current home.
Okay. So you're breaking.
I am. Good for you. Now, do you have any tips for any buyers or sellers that are out there that you share when someone first calls you? What's something you usually tell them?
Resources
A market education. Okay. Making sure that we sit down and give them a good indication of where the market's at, what their expectations are.
Okay. Just to set the page, the tone for what's to come.
Yeah. It is a bit of a rollercoaster ride. And that helps a lot to pave the way.
Yeah. No, I can see that.
Introduction
Absolutely. Because I know when someone's first buying, they're absolutely looking for that help.
That's awesome. We do have to take a quick pause. Then when we come back, it's going to be Steve. Steve will join us from the Joe Collin real estate team.
And we're going to dive into his story and also how he was a star guest on the Naked News. All right.
Welcome back. So now we have Steve.
The Core Idea
So welcome, Steve. Thank you so much for having me.
Yeah. No problem.
It's been fun for sure. So Steve, how did you start?
How was your childhood? Yeah.
Deep Dive
A little different from Jill. Jill grew up here in the Windsor area. I'm born and bred in Saskatchewan.
Okay. Now. Very different area of the country. And I moved around a lot and went through a lot of different things in my life.
I've been a musician my whole life. Awesome. And that took me all over Canada for years.
Yeah. What did you play or sing?
Practical Steps
Yeah. I started singing and playing guitar at a young age with some piano thrown in there as well. Piano is what I primarily learned on. But yeah, I sang all over the place.
I ended up in Canadian Idol. Awesome. Made it to the top 40 two times, 2005 and 2007.
That's so cool. Yeah. Did you get recognized from that? Did any labels or anything want you to do anything for them?
Yeah. There was little things here and there. I was in a group called Hoja for about three and a half years that toured the country and mixed with the Canadian Idol stuff. The music community, even though Canada is a big country, it's very tight knit.
Key Takeaways
Your name gets tossed around when you're out there doing things like that. No, that's incredible. And then so from there, what happened? Did you dive into real estate right away or was there something in the middle?
Yeah, no. My life has taken a lot of twists and turns, but one of the common threads has always been working with people. And even I can say when you're a musician and you're on stage and you're touring and you're connecting the whole, the whole shtick of that industry is connecting with people. And in between that, I bartended and I served tables for a lot of years.
That's like a musician's job basically. And I managed some retail stores and the common thread is working with people, helping people. And then obviously there's a bit of a sales background there already. So when I transitioned into this job a few years ago, it was a more natural transition, I think, than people would think right off the top.
But when you really look into it, it wasn't that big of a step. Now, did you meet Joe first or were you a realtor somewhere else and then you met Joe?
Resources
How did that work? No, I was living in Toronto with my wife for about seven years and this is her hometown, Windsor. So we moved back here after we were married and we bought a home and I had a friend working at Royal LePage and I had just taken my courses. I got a job at Royal LePage and I actually was on my own in the business for about eight or nine months first, but I was in the same office that the team was running out of.
I think they'd been going for about a year at that point. Yeah. And then Joe kicked in my office door one day and sat down and I think the relationship was born in that moment.
That's awesome. So he literally kicked the door?
Basically, yeah. He basically came in and slammed the door and sat down and I think he had just, what he said is that he saw me hustling around the office and he saw that I always looked busy and I was always, you know, stepping in to help people. And that was an image and a type of character that he wanted as he was looking to expand his team. So he offered mentorship for me first and I'd be a fool not to take that and looking into what things Joe has accomplished in his career over the last decade.
Introduction
It was something that I was really keen to be a part of. No, that's awesome. So just for fun, because I'm curious, but do you have any funny or unique stories, embarrassing stories about Joe that you can share with us? In the last few years that I've known him?
No. I can't say there's tons of embarrassing things. We've gone on some team trips where I just remember one where he's, we were in a hotel room and he decided he wanted to show us that he could do a back flip off from one bed to the other. And he ended up slipping and cracking the back of his head on the frame of the bed.
We're all a little silly sometimes, but that, that should have turned a little bit more dark if he hadn't been a couple of inches to the left. Yeah.
That's crazy. That's funny. So then working on his team, do you have a specific role or same thing?
The Core Idea
You just. Yeah. The way that our team is structured is there's six agents, including Joe himself. And then we've got four administrative roles that we have going in the office.
So the six agents typically, we aren't specifically assigned to a role. We are there to service clients and sell real estate and promote the team. And then the administrative assistants are there to keep the cogs in the machine moving. Each of us probably has our own niche that we enjoy working with and that we tend to help, but we're all kind of jacks of all trades when it comes to helping clients.
No, and that's awesome. So what would your niche be? I tend to work at opposite ends of the spectrum. I really like working with first-time homebuyers.
I like taking first-time homebuyers through that process. I feel like you can add a lot of value as I talk to young couples or young singles trying to get into this market. But then I also really enjoy working with older people that are looking to downsize and maybe move from a really big house that they're empty nesting in now.
Deep Dive
Yeah. And I've really created some great relationships with some of the older sellers and buyers as well.
No, that's respectful. Not a lot of people say that they like to work with the downsizers, right?
Yeah. So that's really cool.
Awesome. Now, so I'm really curious about this, right? How do you audition for the Naked News? And maybe for those that have never heard of it or seen it, maybe you could describe what it is.
Practical Steps
Yeah. So I was in a touring band in Toronto called The Modern Hearts. And we were a part of a small label at the time. And it wasn't so much an audition as your management and your team behind you starts to put your name out there and ask around and see what kind of media they can dig up for you.
And The Naked News just happened to be one of them. What's funny to this day, I still have a copy of this interview. For those of you that don't know what The Naked News is, it's literally a program just like this, but it's filmed.
It's not on the radio. And everything, the interview is conducted fantastically. It's still one of the best pieces of media we ever ended up with. But the catch, the niche here is that the people interviewing you are completely naked.
It's a great keepsake for me to have this interview of, it was me and the drummer in our band and sitting there with a completely nude woman, giving us very poignant questions about music. That's awesome. So now I understand when you asked me, when I said, we got to do this show and you asked, do we have to wear clothes?
Key Takeaways
Like, I get it. I get it.
Yeah, exactly. I'm naked right now.
That's awesome. So now back to real estate, but that's incredible.
That's so awesome. So for any buyers, do you have general tips that you give to someone like a standard set of tips or is it random for the person? Yeah, I think the main thing that's really been difficult for people is how quickly this real estate market has changed in the last five years. People in Windsor-Essex County were really used to really affordable market and that's skyrocketed in these five years.
Resources
And the main tip is that we really need to be on top of things quickly. It's all about speed because, you know, these listings go up and sometimes they're only listed for three, four days and someone's snapping it up. We can't take our time like people used to. We got to see these listings the day they go up.
If we want to get an inspection done, we need to do that ahead of the offers. We need to be making sure that we're working with professionals in the mortgage industry like you guys, because I know you guys are all about speed here as well. And we've talked about that in the past and that's really important. And sometimes it takes people a little bit of time to understand that they've got to lose a few houses before they realize just how quickly this market moves.
And I think that's the benefit that you get from a team like you. And I think that's the benefit you get from a team like us. When you got six agents, if you're working with me, you're not just getting me, you're getting me and you're getting the support of the team behind me.
For sure. So if I'm not available in that one moment, I've got someone else who can be available to you.
Introduction
And that's really important. I don't think people quite grasp that when they first get into this market. They think they've got a little bit more time to check things out and then the houses go and then you got to get on to the next one.
No, that's it. That's very true. In this market, speed is everything. When we're looking at lenders, if they have a three to five day turnaround time, that's not acceptable.
You need so much faster. So then we just won't even work with them until they pick it up because it's seasonal. Sometimes they're busier, sometimes they're faster.
No, that's a great point. So awesome. So we have to wrap up for the day, but how does someone who's buying or selling that would be interested in working with either of you two, how would they reach out to you guys? Yeah, we've got, we're all over the socials and that's important in this industry now too is the marketing through social media.
The Core Idea
You can basically find us at our tagline's Realtors for Life, Your Realtors for Life. And we're on Facebook, we're on Instagram.
ca. Okay. And yeah, if you guys need any help out there, anything at all, we are always available. We're always ready to jump in and help and you can reach us at any of those socials.
I think it's the easiest way. That's awesome. Well, I really appreciate everybody coming and thanks for your time today.
Thank you. Thank you so much for tuning into the show today. If you found value, please follow the show and rate it five stars. It would mean the world to me.
Deep Dive
And lastly, all the resources that we spoke about are at the bottom of the show notes. Looking forward to seeing you in the next episode.