KGCI: Real Estate on Air - From Farmer to Top Agent: Ted Cawkwell's Journey to Success

Episode Date: December 25, 2025

Summary:In this episode, guest Ted Cawkwell shares his inspiring journey from farming to building a highly successful real estate business. The discussion focuses on the critical skills and mindset that translated from his farming background, including an unwavering work ethic, resilience, and a deep understanding of local relationships. Ted emphasizes the importance of consistency, long-term vision, and a commitment to hard work as the true foundations of success, regardless of your professional background. This is a powerful, motivational episode that provides a blueprint for any agent looking to build a career based on grit and determination.

Welcome back to the Return on Life podcast. My name is Randy Dick, and I have an exceptional, exceptional, I mean really exceptional guest today. I've only known this individual for less than a year, but what we've put together accomplished and connected on and collaborated on is been phenomenal. His name is Ted Cockwell. Ted is out of Saskatoon, Saskatchewan, and we're going to dive deep into his past, his present, his future, because we're talking about you. We're talking about you as agents and what you need to do to really create an incredible life.

And incredible doesn't mean just money. I mean, that's a big part of it. Money makes everything go around. But we're going to talk about how to structure your life as a realtor and how to get the most out of it and how to create wealth. And I don't mean just financial wealth. I mean wealth that is beyond just money.

So, Ted, I welcome you. and I'm so excited to have you and really excited about this podcast. Yeah, thanks for having me, Randy. I'm super excited about this as well. Building wealth and building a better life is something that really fires me up. And I love sharing tips and tricks that I've found work for me with others so they can have that glorious life as well. Yeah.

And by the way, listeners, if you are enjoying these podcasts and you enjoy these guests or just myself shooting from the hip, please subscribe. We would love to have you on our platform. But, you know, this podcast is called Return on Life, and yet so many of us as agents and entrepreneurs in general just can't find that special spot where they just really feel that there's a return on their life and it's not just another groundhog day.

Ted, take us back, take us back because, you know, we don't all just land here. we've come from somewhere. How did you arrive here? Maybe give us a bit of a journey of your story. Oh, well, I'll give you, I guess, sort of my life business story. And if you wanted me to tap into a different story about how I got here of working less and earning more, that's a slightly different story.

But, you know, I've been a serial entrepreneur. I had my first business at 23 years old. and that was a grain farm in northeast Saskatchewan. I'm a fourth generation farmer on both my mother's and my father's side of my family. So come by the farming honestly, it's literally in my blood and started to learn a lot about that industry in particular, but also business. And, you know, within a few years, I had multiple businesses. I bought a high clearance sprayer when they were a brand new technology. so I did custom spraying for other clients.

And then I got into tourism businesses. I started doing, you know, guided snowmobile tours in the Boreal Forest and started renting out ice fishing equipment. And that whole thing evolved into me building one of the most luxurious and most remote fishing resorts in Canada. And at that time, I exited from farming, went into that. One time, had four fishing resorts. Wow.

At different price points. and then I moved on from that into doing like a little bit of consulting for other businesses, helping them with strategic planning, business planning, marketing was probably my specialty. And after that, I landed in real estate. And I've been a realtor for about 13 and a half years. And, you know, I've found success in this business because I had a PhD in it when I arrived. All my accumulative knowledge from the other business. gave me the skills and acumen I needed to do really well here.

So I know people were looking at me as a real term going like, what are you doing? And I didn't know for the first couple years. And then I finally figured it out. It's like, I've done all this before. I've done the hard work. I've put the pieces in the puzzle. I've failed enough times that I know what to avoid. I've succeeded enough times that I know what works.

And a lot of those things were applicable to real estate. Absolutely. well, Ph.D. in my world means piled higher and deeper. I don't know what your PhD was, but piled higher and deeper. Interesting, you know, I need to go back to the fishing lodges. You had different price points, which is really interesting because what you had learned from each different client at different price points probably really has served you well in real estate. And, of course, in real estate, so many agents charge different fee structures, and I think they attract different people because of their fee structure. Is that correct? Is that how you would

sum up your lodges? Yeah, you know, well, our flagship lodge was an ultra-luxury lodge. So we had clients flying to the flow plane base and private jets. You know, we had NASCAR drivers. We had all these, you know, TV celebrities and really high-profile clientele. And so I learned how to how to speak to them, how to communicate with those type of people. And, you know, now in Saskatchew, to farmland, I work with some of the largest clients. So some of my clients are billionaires, you know, and running large scales at farms. So I learned from those high profile clients how to, you just live in that world, navigate, communicate, I guess is the biggest thing. And back to your commission question, the one thing I did learn is for me, and I have maybe a unique model,

but you never drop your price. You just create more value. And so I learned that with the high end lodge is they don't really care what the price is. You just have to create value for them. These are business people. You know, if they're back then, it was like, you know, $1,000 a day, but in today's world with inflation, you know, double or triple that. So those type of people value their time highly and they just want quality.

So in farmland real estate, when I started, almost everyone was 5%, a flat 5. And over the past, you know, decade, most of them have dropped to half of that or less. And I'm still at 5. But I have team members. I have all these things. We add value. We keep adding more and more and more value. So we charge more, but we put more money in their jeans.

And that was my takeaway on the commission structure moving over. You just don't drop your price. Well, in the absence of value, then people start questioning, you know, the charge, whatever that charge is, whether it's in retail or real estate, it's always about the value that you're adding. And the experience that you're giving the person across the table or across the counter. Yeah, so important. I want to maybe just pause here and say, listen, folks, do you realize who you have in front of you? This is an agent that performs at such a high level. Many years, like not one, not two, not three, not four million dollars.

I mean, we're talking a lot of GCI and a lot of commitment to his clients and to his craft. So when we're talking about building wealth, and I've done a little bit of building wealth as well, you've got to take note here. You know, so many agents just struggle, struggle through this thing called. called real estate, and they're really not quite making it. In fact, so many don't make it. So listen in, lean in, and hear what Ted is sharing with you. Because this is gold.

This is absolute gold. Ted, if you could think of agents. So when you think of an agent who's building a business that they love at 60, are they just surviving? So are agents building something that they're going to love? And maybe I should preface this, because in the last year that we've connected, you've been to Vancouver twice to see me. You've been to Italy to drive supercars all over Tuscany.

You've been to Panagonia to catch some of the most amazing fish that I've ever seen. And you just returned back from a safari in Africa where you saw the big five, and you shared all these experiences. Like, this isn't normal for agents. So agents, listen up. Are most agents building that kind of a business? Are they just surviving? Yeah, most of them are just surviving.

I think it comes down to a belief system, right? You either believe you're worthy or you believe you're not worthy of that commission, of that life, you know? and you have to believe to receive. And I get it. That's not easy. So you have to fake it till you make it. And I do a bit of coaching of some agents. And I was speaking to one the other day.

And she was like, well, I want to do this holiday and I want to do this. And I said, you just have to book it. Like just book it. Well, I don't have the money. Well, I don't have the time. I'm just like, get your credit card out. Book that trip. and then take radical action to do whatever it takes to pay for it.

And so what I try and teach agents in my coaching is when we're talking about time blocking in your calendar, time block your own personal time first, book the kids soccer game in there, book the date night with your wife or husband, book that Safari to Africa, whatever's on your bucket list, life is short, build it in, find a way, and then you build the work in between that stuff. And that's how I make sure that I get to go do all of those epic adventures because they're in the calendar first. I have trips booked in 2028.

Like I just keep stacking them in there. So they're happening. I love that. I love that. I would sit down with my team every January. Actually, we would do it in December. We would plan our holidays before the year started. And everybody on the team has.

to, like, slot their holidays in. That was for scheduling, but also the commitment to do it. And then I would say, okay, now get your credit cards out, like you said, and pay for that trip so you actually go away. And there's a great quote, Be rich now. If you can't be rich now, you can't be rich. It's a state of mind.

So it's really a state of mind in how you believe in yourself. So book those trips, book that time off. Think that you're rich enough to go and do it, and you will go and earn. earn it. You will definitely go and earn it. Let's say you're at the starting line. You're an agent. You just banked 50K. You haven't saved up. You haven't created any legacy of wealth, literally nothing. And you just earned a $50,000 commission check for the first time. What would you tell that agent to do, Ted? Pretty easy. I don't have to go too far back in time to being at that place.

you know, where I had absolutely nothing. Like I had a negative net worth when I came into real estate. I had less than zero. Me too. You know, right? And so what I learned was I got into a percentage game, right? And I was going to put X percent back into my business. And at that time, on day one, it was marketing because I didn't have a team or anything.

So I was going to spend X percent of that 50K on marketing. And then I was going to, you know, put X percent of that 50K away, invest it, right? And so if you work off a percentages, it doesn't matter if it's a $5,000 check or a $500 check or a $500,000 check or a $500,000 check. You build out your percentages. And for the investing part, I think the important part is you just have a certain amount of money come off each check or out of your bank account each month. And it just goes and you don't have to transact. Love that. You know, and here's where I see a lot of agents struggling.

They don't pay their taxes. They're delinquent on taxes. And that's the first thing that I tell agents to, you know, take 30% of your check and just put it in another bank account, a sub-account, or give it to CRA right away. So, like, just get it out of your world because it's going to screw your, future. And so that's so important. I do automatic payments to CRA monthly. So I know how much I'm going to have to pay them this year based on last year. And of course, there'll be an adjustment at the end of the year. And I set it up one time for all 12 months automatic to come out of my

account, just like the investing money. And it's just, it's done. It takes 15 minutes and it's done for the year. And you don't even notice it. It comes in. It goes out. And then at the end of the year there's no terrible surprises you know it's just common sense business just like we're we're prospecting or whatever it is it's just another one of those habitual tasks that you do on a weekly monthly basis and i know that some of us really struggle with it but you have to just really treat your business like a business and if you can't do it you know like some of us are just wired differently then go and find people that can do that for you. Like the numbers side of my world is, I'm just not,

that's just not who I am. I just don't live there much. But I have the most amazing accountant that just keeps me on track and make sure that there's nothing missed when it comes to taxation, because that can be a scary, scary place to be. For all you listeners, please subscribe, hit that subscribe button right now because Ted's just dropping absolute gold nuggets here for you today. What is a wealth-building opportunity that's hiding in plain sight for us as entrepreneurs and realtors?

Well, I'd probably start with like the simplest of simple because I don't think that every realtor is a savvy investor. I don't think every realtor is going to go, you know, build up 20 rental houses. houses and manage that or built up a commercial portfolio or farmland portfolio. There's certain few. Like I have a lot of my wealth is in farmland and I love that space. But I think for the average realtor, it's just taking, like I said earlier, having a set amount of money come out of your account every month and just put it in an index fund, like an S&P 500.

It grows at like 7%. It's not amazing, but it's not terrible. And then there's only two equations that you have to calculate. How much you're putting in and how long you're leaving it in for. So you can work this backwards from your goal. If your goal is, I need a million dollars by the time I'm 60, or if it's 5 million or whatever the number is, then you work it backwards. How much a month do I have to put in? and how long is it in there? And then that just magically happens. Like compound interest is magic. And you just have to have it just taken out.

Like if your average income as a realtor is $100,000 a year, you average your last three years and you decide you're going to do, you know, 10%, then you just go $10,000, divide by 12, and that's $800 and some odd dollars every month, go out of your account into this fund and you can calculate how long you have to work. And hey, and if you raise your income to $200,000, like, kick that up. Keep that 10% number. And it's absolutely phenomenal.

If you grab your calculator, your phone and you go out over 20, 30 years, it is going to blow your mind how much money you have in there. I love that. Keep it simple. Like you don't have to be picking stocks and buying dips and following the charts. Just put it in something safe, like, and just or hire a broker, right? And just tell them if you want low risk, medium risk or high risk, and they'll do it for you. Like you're doing with your accountant, hire someone that has that skill and don't spend any time on it. Like, this might be a hour or two a year to set it up.

You don't ever think about this. It doesn't matter if the stock market's going up or down. You just walk away. You're not touching it for 30 years. Yeah. There's a great quote about that. You're either creating your future or living in the past. And if your past has not been so rosy, start thinking about the future and start putting

some money away. So important. You know, one of the things I think a lot of us struggle with is, actually treating ourselves like we're clients and I remember I would see these fantastic deals and I'd automatically think okay who can I sell this to because there is a commission waiting for me if I sell it to somebody but guess what there's still a commission waiting for me if I sell it to myself and here's the thing treat yourself like a buyer actually physically block off days of your month to say I is

a bona fide client today to myself and get deep into the market i mean you want to talk about safe real estate is the safest greatest investment that you can make and you're in the game and you're not buying it yourself come on so i know you've done this many many times do you actually set aside time to say i'm going to treat myself as a as a bona fide client today or do you just see the deal and go, I need that. So I block off time in my calendar to work on the business, not in the business. And so, I mean, that's kind of a cliche, but I actually block off time. And in that time, I'll do a myriad of different things, right?

So it might be doing a deep dive into the market. It might be looking at an opportunity. And, you know, you and I were talking before the camera got rolling about intuition. And, you know, I have a really strong intuitive sense. So I typically just know if something's the right deal to go into or not. I always do my homework and look at the numbers, but I trust my gut pretty good. So maybe that's not a skill that everyone's home, but all of my business decisions are basically made by my gut. You know, it's interesting.

We don't all have all the gifts. We're not gifted in all areas, and you talk about this gift that you have, gosh, if you're a real estate agent and you're not feeling that intuition, find a real estate agent that's in your office or in your town and say, can you help me with this and get out of the way, let them earn the commission if they're going to serve and help you. I have literally bought property from somebody else and had them help me by the property because it wasn't my area of expertise. yet I wanted to have that in my portfolio. Like, don't think that you can't reach out to somebody else in your office in your town to have you or help you with that. I'm sure you've helped a few agents along the way as well. Oh, yeah.

I'm constantly helping agents. That's something I'm passionate about it. And I don't buy my own properties. I use other agents. And I just, I believe in realtors, right? Like, so I think that there's, this is just my own belief. So I believe there's a bit of a conflict of interest sometimes.

And so I just step aside. And when I'm buying my farmland properties for my investment portfolio, I'll use another agent to buy that for me. And hey, I'm a bit of a control freak. So I'll sometimes guide them on how the offer should look. And maybe you give them, maybe tell them this thing or this thing. But I'm not the agent. Right.

And same thing when I'm, you know, I've sold. I used to be involved in residential real estate where I owned rental properties, and I used other agents to buy and sell them. Yes. And one of the things that really can mess up a deal is emotion. And of course, when we're serving and helping others, we see how emotion creates a rollercoaster of highs and lows. Well, why would that do that for yourself as well?

So I always seek advice of others when I'm buying or selling property because it's my emotion that is clouding my sight, my vision, my mental intuition. So I often reach out to others for support on that, and everyone should do that. And this is what you're basically saying you do as well, Ted. Anything you want to add to that? Well, the only other thing is I love what you say. said about emotion. It's so true because even when I have another agent, I still have that emotion. I just have a buffer because we get emotional about these things. It's hard not to be. You're passionate. You're excited. You're fired up. And so whenever I get in that state,

I always tell myself, give yourself the advice you'd give your client. Right. So I have to sit myself down and go, well, what would you tell your client? Well, just tell them to walk away from the table right now or just tell them to like pay the price and get it done or whatever the advice is that I'd give to my client. I give to myself and I try and follow that and not let my emotions run me differently than the advice I'd give. Love that. Love that. Yeah. I'm going to pipe in here again and just encourage everybody to subscribe to this incredible podcast, Return on Life podcast. My name is Randy Dick and I've got a great guest Ted Cockwell with me today. Ted, have you read the book Die with Zero?

I have not. Not, okay. It's amazing, though. It is pretty amazing, and it really reminded me about the conflict between freedom and responsibility. And so, you know, one of the things, especially for somebody like yourself and myself, we want the responsibility, we want to hold that responsibility of creating something really incredible legacy you know financial legacy family legacy all of those pieces and so sometimes i think we can hold onto that money a little too tight and this this author walks me through or walks you through that you know you have to live you have to have this sense of freedom and i know you live that way maybe share that concept of how you feel so free to be able to go and do all these incredible trips and visit here, there, and

everywhere, yet still have the financial literacy and legacy to be able to do that and not worry about the future, because very few people have the freedom and the financial wherewith all that you do. Yeah, it's a good question. I mean, it probably looks a little better from the outside than it feels from the inside sometimes to be to be totally honest um like i do feel free i know i'm free and and that's powerful uh but i'm human so when i one of the things that i've been working on and i've made pretty massive success on it uh or massive growth is when i leave for a holiday i do feel anxiety

right because my business is my baby it's my heart and my soul. I've put thousands and thousands of hours into this, like late nights, early mornings, all these things that I used to do. I don't do much of that anymore. So it does play with my mind a bit. But I've gotten rid of probably 60% of that in the past year or two through some work I've been doing. But like I said, I just book those things. I know that life is short. And so I want to spend time with my friends and my family and do the vacation. So I just, I just book them and do them. Like if you want freedom, be free.

It's that simple. I'm not sure if I'm answering your question. Well, you are. Yeah, you are. And one of the things I think is that you found that place, but it didn't come because of a free ride. I mean, you worked extremely hard. And I think we need to let our listeners know that, that you have to put a lot of energy.

You have to be a bit obsessed by creating this to get there. It just doesn't come, you know, with ease. It comes with a struggle and an obsession, which I know you've had, but you get there eventually. So you can live in, you know, have a mediocre life, a mediocre financial life, not do many things. or you can press on the gas pedal and go hard to create something for the future. And I think that's what you've done throughout your life in many, many ways. Anything you want to share to that before I ask the next question? I've got a really good question here for you.

Yeah, I will comment on that. I mean, you know, the first 25 years in my working career, I worked about an average of about 80 hours a week for 25 years. There you go. I mean, it wasn't what the average person's doing. in an hour like I was on it like wide open redlining 80 hours a week getting massive amounts of things done and I had that much to show for it nothing Randy like all moments of massive success a massive failure and it was up down up down up down at the end of the 25 years when I was coming

into real estate I had nothing and so you have to be obsessed like who would do that like who would work 80 hours a week for one week, two weeks, three weeks, four weeks, a year, a decade, multiple decades. So when people look at the freedom I have now, and I just choose not to work evenings and weekends anymore, most of the year. Now, I just did have some busy weeks. I worked about 13 hours a day for the past three or four weeks, but I was away for a couple weeks in safari. So I chose to level up. So I think in today's world, so many people are used to scroll. and looking at things and they want the quick instant dopamine hit they want the quick fix there is no quick fix what you put into life is what you get out of life and it's a mathematical

equation like you have to put in so much to get so much out and and you just you have to commit and so you're right i do go in these vacations i do these amazing things but when i'm here I'm here and I'm here every day early and like I just I'm here and I'm executing tasks I'm not going for lunch with friends I'm not doing anything else but a hundred percent focus so that that's all I have to say there's there's no easy ride you you have to commit fully there is no easy ride which makes me the question of is there a belief or a money belief or a success belief that you had to kill in yourself to grow. 100%.

In 2016, I had a real estate coach and he hosted something called the Millionaire Summit. And it was in Newport Beach, California. And I went down. There were 70 people at the event. And I made $1.3 million that year. You had to make a million to be invited to the Millionaire Summit. And I figured out pretty quickly from top income to bottom. I was the bottom in the room.

There was people 5, 10, 15 million in income that year. And that's back when I was still working 80 hours a week. And I got talking to these people late at night, early in the morning, going into breakfast early. What are you doing? What's your secret? They were all working 40 to 50 hours a week. And I left that thing frustrated mad. I was angry for weeks.

I didn't know why, but it was because it was breaking down my belief system that my parents, that my aunts and my uncles, my work. family have told me you have to work hard to get ahead you have to work hard for your self-worth your self-worth comes from your work that's how you define yourself and i i left that with all those agents i respected so much i could just see they were winners and they weren't doing that and so and so i came home and i changed my life and it took a few years and i still work on it because i can easily fall back into that trap, but I don't work weekends and evenings very much anymore, just on occasion when it's needed. And I take time off and I have a different belief system. I don't

believe that my self-worth comes from my hard work. I have a mantra, work less, earn more. I still want to earn more and grow my business, but I'm not, I don't have to do the things I used to do because I don't believe that anymore. You know, it's interesting. I, and I still would say that I have that belief in me, the hardworking nice guy, you know, the harder I work and the nicer I am, the more money I will make. And it's a bit of that underdog mentality where you like being on the bottom. You like adversity almost.

You almost, you know, have an addiction with that because it becomes so ingrained in you. and I really appreciate that response. And, yeah, you don't always have to be the hardest working guy. You do need to be a nice guy and a good guy and build a lot of trust of people. But, yeah, what a great way to unpack that for me. Thank you for that, Ted. Anything that you want to share before we go into a speed round? I know you probably have processed this a little bit.

Anything that you really think we should be bringing to the surface? I well I'm just going to reiterate what I said earlier about building wealth I know so many realtors that are making 200 300 300 500 500 thousand dollars a year and their net worth is a little bit equity in their house that's it they're not saving for a rainy day and they're living a glorious lifestyle now they have a nice house their kids are all in sports they've got nice clothes they have nice cars but how are you going to retire when the money stop And so I just want to tell people, please, please, please, please, please, start taking a percentage of your check. If it's 5%, 10%, somewhere in that range, putting it aside, getting someone else to look after that for you.

Because at the end of the day, when you go to step off and you don't want to sell real estate anymore, you'll be able to live that same glorious life with the cars, the houses, all the things for your kids, all the stuff you want. because you've planned ahead and you only get so much runway so you need to start doing that now I wish someone would have told me this earlier in life so I'm telling you please if you do anything this week just get this done this week and do this for yourself please well shared well shared well let's go into speed round here all right here subscribers subscribe to that button right now let's go but here's our speed round so one book that rewired how you think think about money, one book that you... Buy back your time, Dan Martel.

Great book, great book, yeah. One daily habit that compounds your wealth mindset. One habit that really helps your wealth mindset. When I get to my desk, I lock in. I don't do anything else. I just execute the tasks on my to-do list from high priority down. Okay. Now, not everything is always unicorns,

and rainbows so what's a what's a bad decision a financial bad decision you made uh well i mean even currently i own a couple of rental properties in costa rica and there's lawsuits and lawyers involved and uh you know i've had some made some bad decisions with partners and businesses i've lost a whole business once i've lost about a million dollars in another business recently so i've made lots of bad decisions i just make exponentially more good decisions if you're in business and you're taking risks, which I encourage you to do, just make educated risks and just make few mistakes. Yes.

You're not going to hit a home run every time. No. You're going to strike out sometimes, but you could still be the best hitter in the whole league. They strike out too. Absolutely. Absolutely. Finish this sentence. Most agents would be wealthier if they just took a percentage of their check and

invested it. Love that. Love that. Ted, you lose it all today. What's your first move tomorrow? Back in real estate. Just top-notch client service, just one, one amazing client at a time. Just get back on the horse and get going.

I've done it many times before. That is awesome. Folks, that was gold. If you are an entrepreneur, if you're a real state agent and you have not created financial legacy. It is on you, but you can still change that. You can turn that around today. Take what Ted shared with you. In fact, Ted, how could they reach out to you and you could give them some really tangible things they could do today? Are you available to do that? 100%. I'll even give you my email address and my phone number even,

you know. Well, go ahead and share that right now. Share your contact information. 306-986-725 is my office line. Ted at Cockwell Group.com is my email. And just call me. I'd love to help you. It's a passion of mine to help others work less and earn more. Awesome, Ted. You've been a fantastic guest.

Everybody, this is Randy Dick here on the Return on Life podcast. Appreciate you. Have a fantastic day.