From Bankruptcy to Realtor® Success: Kris Ramotar's Windsor Story
Bankruptcy feels like the end — but for Kris Ramotar, it was the beginning. In this episode, Scott Dillingham sits down with Kris to hear how he rebuilt his finances, earned his real estate license, and built a successful career in Windsor, and the mindset that made it all possib…
Bankruptcy feels like the end — but for Kris Ramotar, it was the beginning. In this episode, Scott Dillingham sits down with Kris to hear how he rebuilt his finances, earned his real estate license, and built a successful career in Windsor, and the mindset that made it all possible.
He discusses giving back through $500 bursaries for graduating students in Lakeshore and Belle River schools, sponsoring a local cricket team, and building lifelong client relationships—holding hands from pre-approval to post-sale support. Kris explains his switch to RE/MAX for better camaraderie, tools, and brand trust amid Windsor's evolving market. In 2025, Windsor's resilient housing scene saw average prices dip 3-5% (around $550K-$616K) with CMHC forecasting recovery in 2026, making it a buyer-friendly time despite higher renewals—perfect for first-time buyers, Kris's niche. This episode offers motivation for overcoming adversity, real estate tips for Windsor-Essex, and insights on community-driven success in Canada's 2025 market.
Guest Bio
Kris Ramotar is a dedicated Realtor® with RE/MAX Capital Diamond Realty in Windsor, Ontario, specializing in first-time home buyers and family relocations in Windsor-Essex County. Born in Guyana and immigrating to Canada in 1987, Kris overcame significant challenges—including near-bankruptcy—to build a successful career since 2016. Passionate about marketing, community giving (e.g., student bursaries and cricket team sponsorships), and long-term client relationships, he focuses on selling lifestyles and neighborhoods. Connect with Kris at krisramotar.com, on Facebook at facebook.com/KrisRamotarSalesperson, Instagram @krisramotar, or call 519-259-9310 for Windsor real estate needs.
Key Takeaways
- Kris's journey from Guyana immigrant to realtor highlights resilience: Overcame parental losses, job loss, divorce, and $126K debt settlement to buy a home in 10 months on single income.
- Entered real estate in 2016 inspired by a gym conversation; focuses on first-time buyers with pre-approvals, hand-holding from start to ongoing support.
- Marketing edge: Uses pro photos, drones, videos, 3D tours, and targeted ads to sell neighborhoods as lifestyles, not just homes.
- Gives back: Sponsors $500 bursaries for Lakeshore/Belle River graduates and local cricket team, driven by passion without expecting returns.
- Switched to RE/MAX for camaraderie, tools, and brand trust; contrasts with previous brokerages lacking team environment.
- Debt recovery tip: Negotiate settlements by offering what you can afford—reduced Kris's debt from $126K to $40-50K.
- 2025 Windsor market: Resilient with 3-5% price dips (averages $550K-$616K), CMHC predicts 2026 recovery—ideal for buyers with realtors like Kris.
- Life lesson: "Just do it"—hard work and no excuses lead to possibilities; build relationships for lasting success.
- (00:03) - Introduction to Chris Ramatar
- (03:31) - Community Involvement and Giving Back
- (07:56) - Overcoming Bankruptcy
- (11:38) - Lessons Learned from Debt
- (14:02) - Transition to a New Brokerage
- (15:07) - Building Trust in Real Estate
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. Thanks for tuning in today. Today, I have a really special guest for you.
His name is Chris Ramitar. So he is an amazing customer service focused realtor, local in Windsor here, who's big in helping to give back in the community. And he's going to share his story today.
Chris, welcome. Hey, thanks, Scott.
The Core Idea
I really appreciate it. Yeah, no problem.
Thanks for coming on. So I think we should get off or start by letting everybody know a bit about you and your story. Where would you like to start with your story?
I'm Chris Ramitar. I have three daughters.
My wife's name is Melanie. I live in Lakeshire, Ontario. I was born in Guyana, South America.
Deep Dive
Came to Canada in 1987. Lived in Toronto up until 2003.
Then came to Windsor. Drove a truck.
Worked at many different places. And then here I am. Something has always been a passion of mine is helping people. And real estate gave me the opportunity because personally coming as an immigrant from Guyana and not knowing the whole process, how to buy a home.
So I'll share my story, what happened to me personally. But yes, it's something I love doing, helping people. And it's an amazing opportunity if you do it right with the right people.
Practical Steps
Yeah, no, I fully agree. So how did you, because I'm curious, so how did you get started in real estate? When I just came to Canada, my dad had a condo and he sold the condo. So the agent said to me, hey, you should look into this.
And at that point in time, I just came to Canada. I'm like, eh, I don't know real estate.
That's not what I wanted. I always wanted to be like a police officer.
So that was part of my dream. Got to where I wanted to be. And then that avenue opened another door for me.
Key Takeaways
So I was at the gym one day, 2016. And my buddy said, hey, I'm going to become a realtor. I'm going to join, take the course. I'm like, hey, I'll do too.
I'm going to go home. So I signed up and he still hasn't signed up yet.
That's funny. And I'm doing well, I believe, in my eyes and opinion.
And here I am today. Four years later, going on my fifth year.
Resources
Yeah. That's funny. So now that your friend has still not signed up, does he regret it?
Does he wish he did? I really haven't seen him too much since COVID. And he's been busy working, shift working myself.
Yeah. And I'm doing the real estate gig as well. Real estate is very time consuming. A lot of people doesn't realize all the work you have to do.
Not just putting a sign on the lawn and put it on the MLS. I am very big on marketing people property because I feel it's a passion of mine.
Introduction
So I look at your home, it's my home. Your money is my money because that's how I view your probably one of the most valuable assets financially in life.
No, for sure. And you actually said something interesting.
You really focus on marketing. Now, without giving out your secrets, but say somebody listening to this, how would that benefit them? What do you do that goes above and beyond what someone does? I first, I use professional services.
I have a professional photographer. He does a drone picture for me, professional video, 3D virtual tour. And then I just don't put it on MLS. I put it on social media ads.
The Core Idea
So I have laser targeted niche to the perfect avatar or client. So when you're looking to sell your home, I'm looking for that one person that's going to be the ideal person for your home. And I sell a neighborhood, not just a home. A lot of people sell the home.
I don't sell the home alone. I sell a neighborhood. This is a lifestyle you're going to expect when you're buying a home in this neighborhood. That makes sense because, yeah, the house might be great.
But if there's no schools nearby and you have children, like, I agree. I think it makes sense to sell the neighborhood.
That's really smart. Now, another thing that I like about you is that you do like to give back in the community. Would you be able to touch on that, what you do to give back?
Deep Dive
Yeah. So because my daughters go to Lakeshore and Bell River High School. So every time, just two years now I started this, I sponsor one student, whoever is graduating and will be attending post-secondary education. There's a bursary reward of $500.
I would like to do that until forever. That's going to be my little giving back to the community that I live in. As well as I sponsor a local cricket team in Windsor that I played for. Cricket's been, like, my number one sport.
I grew up with that and it's in my blood. So it's something I'm very passionate about. And the least I could do is now I'm probably financially more stable than I was years ago.
I could give that back. And it's not so much the expecting anything in return is something I'm very passionate about.
Practical Steps
No, I love that. Now, just going back to your beginning.
So you came to Canada. And how was that experience when you were young, just coming here? It was, like, culture shock in a way because I had no friends. I left all my friends behind in Guyana.
And then we're here. My dad was here three years before us.
So we were three years without my dad. So coming here and the climate is cold. So that's not one of my favorite things. The weather, the winter is not my favorite.
Key Takeaways
I like summer, give it the heat. But it was different. You needed a car to go everywhere. You had to pretty much bundle up in the wintertime.
The people was always nice because I live in Toronto. It was very diverse. Most of the people living in the buildings who was very, like, was immigrants.
So I didn't feel any differently. So because it's a big hospital in the city.
Yeah. Yeah.
Resources
That's awesome. Yeah. No, Canada is a great place to live.
So welcome. But it's funny because you said it's cool and we live in the warmest parts.
So imagine living other places. It's when I want to.
That's awesome. So now you've been a realtor for how many years? Four years going on my fifth year.
Introduction
Okay. And what is something that's, you know, for just a regular buyer, like what's one of the most common questions that you have and what would your solution be to someone who's getting out there to buy? It seemed to be my niche is first time home buyer. So classic examples, Chris, we don't know what do we do.
I said the first thing I do is get a pre-approval. And when you get a pre-approval, I want to talk to your mortgage agent or your banker. I need a letter of commitment.
Yeah. That letter of commitment.
I'm good to go. Then perfect example. I said, give me a hand.
The Core Idea
I was like, what? I said, give me a hand. This was one of my clients last week. And she gave me a hand.
I said, I'm going to hold your hands from here till this transaction is over. And then when your family's ready, I'm going to still be here to hold your hands. I said, this is just the starting of our relationship.
You're stuck with me. You can't get rid of me. I said, I want to sell your child, your grandchildren, a home down the road if I'm still alive. That's what I want to do.
No, that's awesome. I love you do that. Like, how do you give, so someone buys a home, how do you still help them after the fact?
Deep Dive
So, for example, we put in an offer. Okay, what do I need to do next, Chris?
Okay. First, we're going to, I walked through the whole process. You need to get insurance on a home.
One of your offers accepted. You don't have a home insurance. I tell them, you're going to need a, here's a copy of all my list of people.
You need a plumber. You need an electrician. Whatever you need, here's a list.
Practical Steps
This is your resources. That, and then they will call me for anything. The odd thing, oh, we have some leak.
Who do we call? Hey, I need a mechanic.
Who do I call? A lot of times the relationship, personally.
Yeah. My agent, what I used in the past, he sold me a home and he sold my home and I bought a home from him at Crickets. I never heard back from him. The money is in the follow-up.
Key Takeaways
The money is building that relationship. Over time, not expecting anything. A phone call, touching base and said, hey, Chris, how are you doing?
How's your family? That's it.
Just stay in touch. Keep in touch with your friends and family. And don't ask for anything in return. Treat people like the way you want to be treated.
Yeah. No, it makes sense.
Resources
You're right. I remember one of the first houses I bought, I never heard anything from the realtor again. And I'm an investor, so I have multiple ones. And so the next one I bought, the realtor sent me like a gift basket and he called a year later and just said, how was the property going?
And little things like that. So I think it does make a big difference to continue, which is great. And it made me feel good because I'm like, wow, this person really cares. Because someone who doesn't care is probably not going to do that.
But someone who does will. So I love that. Now, we do have to take a quick break. But when we come back, Chris is going to go into how he was almost bankrupt and then how he bought a home 10 months later.
You're going to want to hear it. All right.
Introduction
Welcome back. Okay. So, Chris, I told everybody before we started the break that you were going to explain how you were pretty much bankrupt and then you bought a home in 10 months.
How does that work? Because I believe if you have the drive and the mental capacity to do anything, it's possible.
And I had support. So back in 2010, I'll back it up to 2007.
Sure. My dad passed away in Toronto the day he was supposed to move. We passed away to come to Windsor or Lakeshore with my family. And then a month later, my mom and my brother moved November in 2007, came to Bell River, four houses away from me.
The Core Idea
And then my mom went to Guyana for the first time ever after 20-something years, came back with an infection. And then a couple months later, Christmas Eve, December 24, 2008, she passed away.
Oh, man. Okay. So that's two tragedies in, I don't know, 14 months. Then four months later, went into work.
Hey, Chris, we don't need you anymore. So this is April 1st, 2009. And then one month later, my ex said, hey, I'm not happy.
And I said, okay. Then she said, I have a boyfriend. I said, all right, what else? And then we had two daughters.
Deep Dive
They were pretty young, like less than five years old together. There was a lot of struggles, things that happened before that. I'm not going to go into detail. And then we had a trucking company, which were going well.
And then three to four months into it, a truck crash, driver quit, people not paying the bills on time. And the money start, what we had to run the business, drive it pretty quick. So at that point in time, my business folded. I got a job at a local company with Ashok Food, Champion Products.
Thanks to them. They helped me and they're still helping my brother today.
They both employ my brothers. Wow.
Practical Steps
Still work there. So I left there and there, my brothers are still there. And then laid off for five months. Got hired by the University of Windsor, thank God.
So it's a great opportunity there for my kids and myself. About a couple months later, I had an opportunity to go back to Toronto, Toronto Police.
And I declined. Yeah. So we owed over $126,000 in collections and debt from the truck and the company and everything.
And the house was sold. There was a $40,000 lien on the property.
Key Takeaways
So $20,000 was given to us. $20,000 was held in my ex-son name. We took the money, split it.
I said, here you go. I took my $10,000 straight to the bank, pay RBC collections.
I caught up everybody. Hey, I have some money. Can we negotiate a release or a deal or some sort of a thing?
And they said, yeah. I said, okay.
Resources
So I made a release letter. This is what I can afford.
And everybody said, yes. So this was back in 2009. 2010, I went to the bank to get a loan. It was tight, but it worked out.
So what I did was I took a credit, a car loan. I had 30% interest, but I knew for me to get where I want to be, I had to make sacrifices. It was not a big loan. It was only $5,000, but I paid it on time.
I took a Capital One credit card and a $500 credit limit. I paid it on time. I had some RSP from FedEx, about $15,000, which helped me. And then working at the University of Windsor, I saved over 20 grand.
Introduction
And so when I went to the bank, I said, hey, listen, this is what I have. I have everything lined up. And yeah, I got a mortgage for $197, bought my total home in East Windsor and never looked back. And I always tell people, if it's meant to be and you work hard, you can get anything in life.
And don't say, oh, make any excuse that, oh, it's not possible. Don't wait.
Just do it. And you'll find a way of getting where you want to be.
Nice. So that would be your best lesson is just do it.
The Core Idea
Do it. Yeah.
Don't wait. Jump in and go.
Yeah. No, I love it. And that's interesting too about the debt that you had. So I think that's valuable for people listening because if they're in the life stage that you're at and you have debt and you just want to get past it and move forward.
So how does that work? So say you have debt and you can't pay it. What did you do to get them to settle or reduce the amounts for you? I just called them and said, this is what I could afford.
Deep Dive
Either yes or no. And for some reason, they say, yeah, we'll do it.
It's hard for that. Maybe God was looking up on me.
Yeah. Very well could be. From 126,000 to 40,000 to 50,000 settlement, I can't complain.
Yeah. No, that's great.
Practical Steps
That's great. That's really cool. So he's saying you just call them up, which is great.
So anybody can do that. I love that. Now, your home that you bought, because one of the things that I thought of when you told me that, was the interest rate really high or was it? I think it was around five or something.
Five. It was pretty low.
It was in 2010, right? Yeah.
Key Takeaways
It wasn't too high. It was pretty low.
Yeah. It was still affordable. I can't remember exactly how much it was.
Okay. Yeah.
Yeah. But I did it by myself on a single income.
Resources
Yeah. A single that.
Yeah. Was it with 5% down or was that with 20?
5%. Wow.
So that's really good. That's really good because I know CMHC is tough.
Introduction
So good for you. That's awesome. So you went from bankrupt to buying a home. And then, so what happened after that?
Obviously, you started the real estate in 2016. What was the middle like there? In between, I was always operating in the red. And it's true, paycheck to paycheck.
Yeah. And the least thing that brought me to my knees. But I took a chance because I said, if I sit at home with my brothers, which we live with my brothers, my two kids, myself and a nanny. So we had pretty much four adults and two kids in that home.
We all got along together. I said, if I take a chance, now I could do it because if I sit here and wait, it's not going to happen.
The Core Idea
Yeah. And I said, if I know where my money's going and I'm broke, that's okay. Whereas if I am broke and I don't know where my money's going, then something's wrong.
Yeah. And I sacrificed and I built equity and it was a great risk.
That's awesome. Great risk.
Good for you. And I know you're doing really well. I see you all the time out there and you're doing a great job. I realized or saw that you had a recent brokerage change.
Deep Dive
What was the benefits of going to the new brokerage? Where I was, this is my Ford brokerage. I went to Tom Thomas, opened the door, was grateful, Century 21. Great things about him, but I wanted to grow.
C. Platinum.
Wanted to grow. And then I saw EXP and the model was awesome.
Tools, technology, training, support. But what I found, and this is from my personal experience, there was no camaraderie and collectively team environment. Everybody pulled their own separate ways.
Practical Steps
Yeah. And what I called, I said, hey, Scott, it's Chris Ramatar from EXP.
You're like, where? Who?
Okay. So I'm trying to sell myself on a brand. You know, right now, it's not a big brand here.
Windsor, SS County, the balloon. Everybody know.
Key Takeaways
It's synonymous. Remax is synonymous with real estate in Windsor, SS County. So you want to go a place where when you say, hey, it's Chris from Remax, and you see my balloon, it's already trusted. I don't have to sell the brand.
Yeah. I just have to sell, show you what I could do.
Yeah. It's only been two months, but the camaraderie, the support to have a physical office, in my opinion, is huge. You become more trusted when somebody says, hey, meet me in my office. You call the staff and, hey, can you do this for me?
Whereas where I was before, who do I call? I had some people on my team, but they were not hungry.
Resources
Yeah. I gave leads out and you call, no, I'm going to call this afternoon. Hey, the lead just came in.
Call now. I'm spending money.
Yeah. But it's not your money, so why are you going to work your...
Yeah. And I'm very passionate about what I do.
Introduction
I love what I do. But the brand, I think by itself, and the staff, and the professionalism, and the camaraderie, and the support, it's second to none. Plus with a big global brand, you couldn't ask so more.
No, that's awesome. Good for you.
I'm excited. Yeah, I saw the post on Facebook.
You go, Chris. Perfect. So we do have to wrap up, but for anyone who's listening today, what would be the best ways to reach you, or how they could find out more about you when they're considering choosing a realtor? I think my biggest place is on Google.
The Core Idea
Just Google Chris Romitar, K-R-I-S-R-A-M-O-T-A-R. And you're probably going to see a hundred stuff pop up over me. So everywhere there's a medium, you're going to find me.
Facebook, YouTube, Instagram, Twitter. Everywhere you can think of this, you'll find me.
Yeah. Okay.
Okay. That's perfect.
Deep Dive
That's awesome. Thanks so much, Chris.
Bye. Have a great day, everyone.
Take care. 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.
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.
Practical Steps
Bye.