REAL ESTATE Strategies with RE/MAX Hallmark
Real Estate Strategies with RE/MAX Hallmark is the go-to podcast for real estate professionals who are serious about growth, impact, and staying at the forefront of the industry. Designed for top-producing agents and those driven to become one, this podcast offers a smart, high-level look at what’s shaping the real estate landscape today. Hosted by Jessica Ragimov, it offers practical tools & market insights. Real Estate Strategies delivers real value you can apply immediately.
Each episode dives into the latest real estate news, business-building tactics, and timeless principles that define successful agents. Whether you’re navigating interest rate changes, shifting inventory, or client expectations in a post-digital world, we keep you informed and inspired. What’s more, you’re hearing it all from within one of Canada’s most respected brands—RE/MAX Hallmark.
You’ll learn how to interpret the real estate news that matters, understand buyer and seller trends, and develop habits that build long-term client trust. From marketing strategies that actually convert to leadership skills that retain top team members, Real Estate Strategies is where great agents come to sharpen their edge.
As a flagship production of RE/MAX Hallmark, the podcast is also a reflection of the brokerage's mission: to equip agents with the tools, mindset, and community they need to thrive. Powered by RE/MAX
REAL ESTATE Strategies with RE/MAX Hallmark
What If Your Community Was Your Marketing Strategy?
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
What if the secret to a 14-year award-winning real estate career had nothing to do with marketing spend?
Johnder Perez sits down with Kevin Cahill, a Pickering-based RE/MAX Hallmark agent who built his entire book of business on community roots, authentic relationships, and zero dollars in advertising.
Before entering real estate at 49, Kevin spent 38 years as a civil engineering technician with the City of Pickering, organized the local Terry Fox Run for over two decades, and ran golf tournaments for the food bank… all without ever self-promoting.
His story is a masterclass in how values, consistency, and community service can become the most powerful real estate business strategy of all.
Now, Kevin is launching Cahill Co. alongside his children, growing a family legacy built on service.
Listen For:
:50 What inspired Kevin Cahill's 38-year commitment to community service before real estate?
5:27 How does a civil engineering career with the City of Pickering translate into real estate expertise?
10:39 How did Kevin build a successful realtor business without spending a single dollar on marketing?
17:16 What does Kevin's journey tell us about when agents should enter the real estate business?
27:36 What advice does Kevin Cahill have for agents struggling to stay consistent in a challenging market?
Connect with Kevin Cahill, Chief Operating Officer/Owner | Broker/Owner at RE/MAX Hallmark®
Connect with Johnder Perez, Director of Innovation & Business Development | RE/MAX Hallmark®
Kevin Cahill (00:00):
For anyone volunteering, it is just do it. It makes you feel fantastic about yourself. And I think if you feel really good about yourself and that you're helping out in your community, I think that will translate, maybe not right away, but down the road to potentially some clients and a better business for you.
Johnder Perez (00:22):
All right. Welcome everybody to this episode of Real Estate Strategies with RE/MAX Hallmark. And today we have a great guest. His name is Kevin Cahill. And Kevin, welcome to our podcast today. You ready to have a conversation about you, your life and real estate?
Kevin Cahill (00:40):
Sure. All new to me, this stuff, but certainly kind of honored and real happy that you've asked me to come and have a chat.
Johnder Perez (00:50):
Well, absolutely, because it's going to be your foray into podcasting as well. It's interesting that this conversation between me and Kevin and me coaxing him and trying to get him on this show was because of a website that he is going to be launching with Sky, with his team, his family, and his real estate brand. But Kevin, we're going to start today at the age of 18 years old. And this was a story you shared with me, so you brought this up. 18 years old, you're 18, and this significant Canadian figure named Terry Fox was running by. And this was pickering, right? And this was pickering. Correct. Correct. And you had missed out an opportunity and it pains me to remind you of this time, but why don't you take us back for your life and real estate journey to that specific moment and tell us why we're starting our conversation at that point today?
Kevin Cahill (01:42):
Yeah. It's one of those things if I could take something back, relive something, I certainly would. I think I was maybe a little young, maybe a little immature, of course, at that age, thinking about yourself. And I just have a phrase that I just didn't get off the couch and go see Terry go by on Kingston Road in Pickering, July 11th, 1980. And before I forget, pretty special day today. Terry Fox would've been 68 years old today. So happy birthday, Terry Fox, as you can see it. He's certainly a big idol of mine. Since I missed that big day going through, certainly I thought long and hard about things and thankfully. And I volunteered back in 1980 some 38 years ago with our first Pickering Terry Fox run out of the then Pickering Recreation Complex. It's the Chestnut Hill Rec Complex now. And since then, I've been volunteering.
(02:46):
And I'm guessing the last 25 years I've been the organizer of Set Run every year for cancer research, which is of course near and dear to many of us, but what an idol, what a just tenacity Terry Fox. And that's just a big word that we use and a hero of mine.
Johnder Perez (03:07):
That's amazing because I mean, a story like that, it couldn't happen any other way. And as painful as the memory is, and of course to pause and reflect to it, it's what actually invigorated you to be involved with the family of Terry Fox for so many years. And so Kevin, we're going to take this journey through a conversation, not just about real estate because you were and still are an active figure of the Pickering community. Your roots is in Pickering. You served for the city of Pickering. So why don't you take us back before you were in real estate, in your journey being involved in the community, your work with Pickering, before your transition. So take us back through that time period first.
Kevin Cahill (03:50):
Certainly got to always thank your parents' work ethics. And my dad, story, he worked in the bank, you didn't get paid. You had to go work in a factory. Well, he just had to go work because he had four kids and that's what you do. And I was able to get through a college course of civil engineering, and I would guess I was the first co-op student back in 1980 for the then town of Pickering, now the city of Pickering. And 38 years later, I stayed with them my whole career, like you were saying, quite involved in the community, certainly with our local food bank as well. 20 years of running golf tournaments for them and certainly with a fantastic committee, just like the Terry Fox. You can't get anything done. You have to have true volunteers that are quite involved as well. But my pickering career was just fantastic.
(04:51):
I can't say enough. Moved up the ranks. And I like to think that I served the community for 38 years giving service, but customer service. And it translated at 49. I guess I went and got my license 14 years ago. And that same customer service is what I like to think that I bring to any of my clients now. So yeah, where did that 38 years go? I don't know. Where did the 14 years go in my real estate career here? So it goes quick.
Johnder Perez (05:27):
Well, as I say, time flies when you're having fun and 38 years serving for the city, then town of pickering, evolving into the city of pickering, and then 14 years award-winning realtor, RE/MAX Hallmark. So Kevin, what have you seen? I mean, it is fitting that you're a civil engineer. And I would presume, I guess, with your job with the city or town of Pickering at the time, was it related more or less to the city, the development? What kind of work were you in when you were working with the city or the town of Pickering?
Kevin Cahill (05:56):
So again, I went to college, so I was actually a civil engineering technician. I didn't go to university and get my ring, but I guess I first started, I was a construction inspector. So in all the new subdivisions back then, in the '80s, I would go in with my white hard hat on and trying to learn all the tricks of the trade and things with different coworkers and contractors. And kind of oversaw all the infrastructure development, everything but the house
(06:35):
That I would get involved in. That has kind of laid the groundwork. A lot of times I can tell my clients, your house was built by Jerry Coghlan or by Sanbury Homes or by the Land for Dixie Group, what have you, because I was there putting sewers in and watching the development go on. I then transitioned over to the capital side, and that's essentially where the City of Pickering work. It's all tax dollars going to that bridge or to those road reconstructions or stormwater management ponds, et cetera. So I found that was much more important because that was 100% tax dollars. In the development side, it's all the developer paying for all the costs. And I was just the eyes to make sure we got the product so that when it was assumed that subdivision, the city would have a nice, clean, working subdivision and no further repairs for other than maintenance down the road.
(07:39):
But on the capital side, it was 100% dollars. So I found that more up my alley where I could oversee and really do what I really liked doing at Pickering. So I did that for a long, long time. And you know what? At 49, I was like, "Boy, at 55, I can go full pension. I've been here. I better think of something." So I thought about going with a consultant engineer or builders or developers and talked to a few other local companies and I got talked into going to the real estate. And I like to say I was worried about that five years. Well, again, 14 years has gone since then. And wow, time flies when you're having fun, like you said. So very rewarding. I can't say enough about the City of Pickering. Cliche, I bleed Pickering, but I just feel, I use the word, it is incumbent on me, Kevin Cahill.
(08:43):
I was given so much, so, so, so very much from the City of Pickering. My kids all through university, all successful grandchildren. That's why I give back and have given back to our community so, so much. It's so, so important. And my family name and for my dear father, I'm going to start crying in a minute, but for my name's sake. So thank
Johnder Perez (09:08):
You. Yeah. Well, I mean, it's amazing to see that journey because from town of Pickerings, being involved in the development, seeing the development, knowing the builders by name, knowing which subdivisions are built. And then today, of course, servicing Pickering in Durham area, you're driving up and down these streets and you know where these subdivisions are, you know when they were built, all of these things. So you transitioned into real estate after 38 years of serving for Pickering, knowing full well all of the different intricacies of neighborhood subdivisions. When you were starting out, because now you're 14 years, you're award-winning realtor, but when you were starting out, what were some of the challenges you faced during the transition? And I'm going to go into some of the things that we talked about because for everybody listening and watching our show, Kevin is very humble. The meeting that we just had, and I hope you don't mind me talking about this, the meeting we had when I first got introduced to what Kevin was trying to do with a website, I'm like, how does a successful award-winning realtor do so much without even promoting themselves?
(10:17):
Because Kevin, you're not even big even till now about promoting yourself, even to get you to speak about what your accomplishments are hard. But when you were starting out in real estate, real estate being a sales-related business, what struggles did you encounter and how did you overcome and succeed to get your first clientele ahead of the 14 years of an amazing career that you've built?
Kevin Cahill (10:39):
I was wondering if you were going to ask something like that. I think, I don't know, I'm quite a laid back. I don't want to be one of these individuals who chase and would pester or whatever. I'm very, very fortunate. I have a very large network and I think I'm an okay guy. I think people entrust in me and certainly not going to talk anyone into something that they shouldn't be doing, of course. None of us realtors would. But I don't know what it is or what has transpired. I don't want to say any luck or whatever, but I think it's just staying the course and just being the way I have been and not changing just because I now have a realtor hat on or whatever. I just think people trust what I say and know that they'll be looked after. And I hope I've been doing that for all my clients.
Johnder Perez (11:38):
Well, in our conversation, when we first casually started talking about this, you had mentioned something along the lines of exactly what you just said right now is you weren't salesy in the sense of just let's say the prototype or the stereotypical person we would see when we listen to or hear the word salesperson. But you spent a lot in terms of marketing, getting people to call you, the relationships that you built. So having built a successful career, we have real estate agents that are just starting out now. I mean, we have real estate agents that have been successful, but maybe they've hit a rut or a challenge or they're trying to get out of. What forms of marketing or advertising or connecting with clients? I mean, mind you, after 38 years of working with the city, I'm pretty sure you've developed a big network. How much of that was your foray into a successful book of business, building a successful book of business versus did you spend money on marketing, advertising back 14 years ago to develop?
Kevin Cahill (12:39):
Yeah. So I haven't spent one nickel on marketing. It was my kids who talked me into, "Oh dad, we got to do a website and this." And I finally said, "Okay, we can do that." And again, I'm not. Because you do something in the community, Terry Fox, a food bank, or whatever you choose to do, we don't do it or you shouldn't be doing it for accolades. So it's very hard to talk about yourself. I'll go back to the. I had 20 years did a dol tournament for a local food bank with our picker and squash club. And a few people would say like, "Oh, come on, Kevin, you're making some money in real estate. You should be sponsoring the whole and have your sign and all that." And I'm the opposite. I'm like, "No, I'm organizing this. We're making my food bank. I cannot self-promote myself.
(13:35):
Sorry. That just would be, to me, orally, ethically wrong." So for anyone coming in new, I guess is the question. Certainly there's nothing better in life, in my opinion, than the gratification. I'll go buy our food bank and I'll see the sidewalk is just lined with hundreds of people knowing that I've done a little part to help with the food insecurity there. So for anyone volunteering, it is just do it. It makes you feel fantastic about yourself. And I think if you feel really good about yourself and that you're helping out in your community, I think that will translate, maybe not right away, but down the road to a larger network and potentially some clients and a better business for you.
Johnder Perez (14:28):
Which is great because I mean, in terms of your philosophies, being very humble as you are, real estate being sales, marketing, promotion type of a business, you kind of went against the grain and didn't do that. And yet have seen a successful real estate business and career develop because of just who you are, the values you stand for, and community. So I mean, sponsoring a hole in golf, yeah, of course.This is your event. You put yourself out there guaranteed you're going to get recognition, but you chose not to do that. And yet the rewards that you've reaped from building community and just maintaining truth to your philosophy is abundant. So in terms of over the years of you trading in real estate to Kevin, what would you say were some of the biggest, I guess, some of the impacts? And over 14 years, you must have bought and sold multi-generation of families at this point beyond just the first move.
(15:25):
Because if people are moving every three to five years, some of your moves are like two to three times now in terms of working with you. So what kind of impact do you feel you've made on families having started just 14 years ago after a very successful career with the city?
Kevin Cahill (15:43):
Yeah. So what's happened is certainly my vintage, friends of ours, I guess well into the '60s, done a lot of work with a lot of our friends and clients. And one or two deals say they pick up the new, pick up, move, but then they're children and then they're friends. And you know what? Again, I think they like, I guess, the way my nature and that has translated into certainly some good business ties. And I guess it's not a bad thing. I've always been in anything I did and do being respectfully, but quite competitive. There's nothing like getting when you've got the buyer hat on, there's not a better turn on than getting that deal for your guy or whoever. It's just what? You worked your tail off and you just. I just had one the other day and I bet my friend Trevor that within 24 hours I'd get a call from the agent.
(16:54):
I lost the bet. It was 48 hours and we were able to get it for the price that we initially put in. And then the same thing when you flip and put the seller's hat on to try to maximize. So I do have a little bit of a nature in me, but it's of course for the client.
Johnder Perez (17:16):
Right. Well, I think that's inherent because if you want to fight for your client and to fight for what they want and what they deserve, you've got to have that spirit in you. And it's interesting, Kevin, so I'm going to go into sort of a mind exercise now because these days we have real estate agents starting out as early as 18 and some real estate agents start out while they're younger. They haven't had an established career. They haven't built a network yet. Real estate traditionally, or at least when I guess the proliferation of real estate as a business career came out, you usually would have somebody who has had work experience similar to how you discovered it. Seeing how you've unfolded with your real estate career and knowing everything you know today, I know that's why this is a though exercise. I know we can't go back in time.
(18:03):
Knowing everything that you know, going through all the challenges that you've gone through and building up over all the things that you've built up, if you were to go back in time, would you have done real estate first or would you still have gone through and say, look, you know what? I'm going to do something career-wise that contributes to this or something in my background.What would you do now? Do you ever think back and say, "Hey, if only I had started 14 plus 38 years ago?"
Kevin Cahill (18:29):
Yeah. Well, the quick and firm answer would be no. I'm very conservative in nature. Real estate, of course, is commission-based. I'm quite conservative in that regard. So no, I would've always looked for the for sure thing. And of course, certainly if I'm going way back to marriage and kids and all that, you got to have that steady, or at least in my opinion. But certainly those can get in it and it's quite lucrative, but I'm not sure what the equation is now, but about 20% of the agents making 80% of the money or what have you, whatever that scenario might be ratio. But I think it would be a tough slug. And I just think for those who are maybe just getting out of university, if you don't have the network, you got to have network and somehow obtain that to get your client base.
(19:31):
But of course there's individuals out there who could probably just start out fresh and do it. But I would dare say the majority of the people, it would be quite tough on them. But it's been quite rewarding and fun. But to start all over doing commission-based, a little story, my brother-in-law years ago, I guess I was maybe in college or whatever, I had a friend. He said, "Geez, he's looking for a guy. He's with Clare or one of these shampoo places." I wouldn't have been a good spokesperson for shampoo product at the end of the day. And it was all commission-based. I said, "No, Rick. No, no commission-based for me." I recall that some 40 odd, 50 years ago.
Johnder Perez (20:16):
Which is interesting because I mean, in real estate, we meet all types, all risk appetite levels. And because it is commission-based, it is literally your performance is based on how well you do. Mind you, a big part of that is the network as Kevin has established here. But it also shows that these days, it would be fair to say it's a bit of a challenging market filled with opportunities at the same time. There are people that are from all walks of life that are looking at, you know what? Maybe I've got to transition careers, maybe I've got to move on to this. But the blessing of starting after a successful several decades of a career is you've got the network, you've got the maturity, you've got the financial stability. Yet on the flip side, you do get the younger agents starting out with, maybe they have friend networks, but how many university graduates are buying houses or condos unless they've got money somewhere?
(21:06):
Which brings me to this as well. So you mentioned earlier that in as much as you don't like self-promotion as much, which is very good because I mean you take more of a humble approach to the way you market real estate, you're at the same time competitive. You've got that competitive fire and nature in you, Kevin. So what would you say, what gets Kevin up in the morning and say, "You know what? I'm going to do something for my client today, or I'm going to build this relationship today, or I'm going to make a sale today." What gets you excited about real estate on a daily basis?
Kevin Cahill (21:36):
Short answer. I like to win. Short answer. But no, it's just very gratifying. I've met so many blessed to meet so many fantastic agents even outside of RE/MAX Hallmark. Honestly, call them friends, called others for advice and things, and it should be just wide open and we're all in the pool together, so to speak. So my mother used to say, "You've got St. Vitas Dance." And I think that's a slang phrase or the real phrase for you have ants in your pants, Saint Vitas dance. So I just am not one of those type of guys to sit and wait till, oh, I can cut the grass again.
(22:24):
I've got a couple listings now that are getting a little gray hair in them. Just vowing that I got to get rid of these for my client. So I'm trying to think of any way and any other marketing that I can do. So I've really tried to roll up my sleeves on that and then hopefully move on to the next one. So especially with my. We have three children. Two of them are now going to get involved and help me. They'll eventually get their licenses and that. And you know what? I said, "Let's do it. Let's form this." One of my daughters came up with the Cahill Co tagline and Ko being really what says to me is not company, but community.That's what I really take from that. And let's see what we can do together and maybe expand what we've done so far.
Johnder Perez (23:27):
Yeah, dancing your pants thing. You just got to feel busy. And I feel you. I
Kevin Cahill (23:33):
Do. It's very important I think for anybody. I was quite worried at 49, what the heck am I going to do? And I ended up talking with another RE/MAX agent, my good friend, Jim Kelly, who we've known each other a long time. And I transitioned and went with Jim. Back then I was still working and who the heck was going to go with Kevin Cahilll, full-time City of Pickering, part-time realtor. So it was a blessing. And Jim is just quite, quite excellent, wealth of knowledge. So kudos to Jim. And you know what? It's been a fantastic 14 years and I want to keep it going and get my kids involved and see where we go.
Johnder Perez (24:23):
So Kevin, now you've got family. I got to meet Sky because we were talking about the website and you're launching a website for the first time and now you've got marketing rolling. What's your vision to have your family involved in real estate, building up the Co in Cahill, which is the community? So what's your overall vision and how do you see it playing out with family and with the community you're building?
Kevin Cahill (24:50):
Yeah, so long time coming. I've talked about it for a little bit. My kids, "Dad, you got to get into the year 2000 here at least." And so anyways, I was away last winter for a little bit and Sky said, "We're doing it." And so we started putting that together and I guess other social media platforms. To be quite honest, I said, "Have at it. You get organized and we'll work together on it and I'm sure it will be helpful down the road." I think it's fantastic, not only my eldest daughter, Sky, Guy Stewart, and our son Jordan Cahilll. And so it's Sky, then Jordan, and then a younger sister Sarah. And I think it should be just a work in progress. I just say, let's just slow go. Finally, after 14 years, I'm going to do something. And us collectively, let's just do it slow, but do it right.
(25:57):
And you know what? Put things in there that are very useful to people. Hopefully we get some traction. And then hopefully we earn the trust of potential clients and we can move things forward as a little team and bring my kids involved to learn and hopefully follow in their daddy's footsteps and continue to serve in our community.
Johnder Perez (26:29):
Well, that's the greatest thing about building a legacy brand, right? I mean, affiliating yourself, of course, with RE/MAX Hallmark, building up a brand for yourself and now your family getting involved and continuing the legacy of community service, being involved, making a difference in people's lives. So that's just an amazing thing to wake up to every single day. So Kevin, before we finish up, and this was a fantastic conversation, I appreciate you sharing the stories with me. No, thank you.
Kevin Cahill (26:54):
Thank you.
Johnder Perez (26:55):
It's our pleasure. So just one final piece of advice for you before we wrap up. And then of course we're going to share your contact information. So anybody looking to send business to Pickering, Ontario, Durham region in Ontario, Canada, Kevin, they'll be able to reach out to you. But before we get to that, there are real estate agents starting out today, and this we briefly alluded to earlier. Some are starting out, brand new, completely new to the field, whether they're fresh out of university or whether it's a second or even a third career for them. There are those who may have been in the business for decades now, but are struggling. If you were to give a piece of advice to them watching and listening right now about how to overcome any challenges or hardship that they're experiencing right now, what would that be, Kevin?
Kevin Cahill (27:36):
I guess you just got to stay the course. Don't change who you are. Be very upfront, truthful, moral, ethical, and just stay that on that track. Consistency, consistency, consistency. I think if you can stay with that and then just make sure that your potential clients see that consistency and that grit determination for them, it will come your way. May take a little bit while, but you know what the old saying, you got to roll your sleeves up. And if you knock on a door and it doesn't answer, you know what? You got to knock another door. And nobody said it was going to be easy. Everyone before us did the same thing. And you know what? Kind of comes down to that winning attitude. Do you really want or do you really, really, really want it? You know what? If you're starting out, you got to be really, really, really wanting it.
(28:38):
I mean, I have an expression, if you jump into something, I jump in with all three feet, meaning 110%. There's only one way to do it. And that way you can then look back and go, okay, well, I tried my damnedest. Or you can look back and go, "Well, I really only gave it 50%." So you're not expecting much. But it's a tough gig, especially with this market right now. But you know what? Stay the course. You should do okay.
Johnder Perez (29:12):
Words of wisdom from Kevin Cahill. Grit determination. You got to have that fire, the competitive nature. The way he said consistency multiple times, because in real estate, that's one of the biggest failure points is just failing to do something consistently. But one of the things that's got to be taken away is are you 110% versus 50%? Are you just dabbling in this business or are you all in? And are you building a legacy out of it? So Kevin, thank you so much. Kevin, what's your phone number? Because I know the website is coming up soon. We'll put the website up when it's ready, but what's your phone number, email address, any contact information? Anybody listening, watching to this can send business to you and to your team?
Kevin Cahill (29:49):
Yep. So phone number 905-706-1216. KevinCahill96@gmail.com. Our website is Cahilllco. But I guess more importantly, if I may make a couple plugs, the 46th annual Terry Fox run in your local community is this Sunday, September 20th, terryfoxrun.org and/or in your local community, please. Ours is st.paulsondehillfoodbank.ca. Anything you can do or give or come out to support, we'd really, really like that. And you know what? I really appreciate, quite humbled. Thank you for asking me to come out and have a chat. I love what I do. I love RE/MAX Hallmark. Everything's been fantastic and just thank everybody involved.
Johnder Perez (30:43):
It was our pleasure to have this conversation and your words of wisdom, Kevin, because one of the things that rings true, and you can feel it, whether you're watching or listening to this, you can just feel it from Kevin, is that real estate is one of those things you do in life that you've got a major impact, not only on the individuals you serve, but on the communities. How many opportunities you have that you're working in real estate, yet at the same time, you're making a positive impact. And Kevin, I mean, it's amazing just to the degree of how committed you are to serving, pickering, to serving your community. And that's just fantastic to see. So we thank you.
Kevin Cahill (31:18):
Oh, thank you.
Johnder Perez (31:19):
Absolutely. Thank you everybody for listening and watching to Real Estate Strategies with RE/MAX Hallmark. Depending on where you're joining us, make sure you like, subscribe, rate us, all that good stuff. Share this episode. I know Kevin and his family's going to be sharing this episode with all his clients, so go ahead and make an impact today, volunteer, do something for your community. I know Terry Fox would be proud seeing this, right? And that was such an amazing story that you shared with us, Kevin. Thanks everybody. We'll see you next time.
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