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Show Summary:

This Episode starts with Scott Dillingham sharing personal details about his background and upbringing. Scott mentions being born in the same hospital as Stephen King's car accident and growing up in Maine. Scott's parents separated, and his stepfather worked as a broadcaster. His family was sponsored to move to a new place for their stepfather's job as an announcer for the Raceway.

Scott discusses their childhood, being troubled and often left alone with babysitters who didn't provide much guidance. Scott expresses a preference for exploring and being his own boss rather than following authority. Scott mentions struggling in school, receiving bad grades, and facing negative remarks from teachers. Scott failed grade Six but appreciated the experience as it allowed them to make good friends. Scott continued to misbehave in high school, leading to multiple suspensions and eventually expulsion.

After being expelled, Scott entered the sales field and excelled in various positions. Scott worked at Sears and a call center selling high-speed internet and TV services, consistently ranking among the top sales reps. Inspired by the book "Rich Dad Poor Dad," Scott became interested in real estate investing and attended courses to learn more. Scott began wholesaling properties and had an unfortunate experience with a dishonest partner, which resulted in him accidentally purchasing a property.

This experience led Scott to become a real estate investor. Scott continued to grow their portfolio, eventually owning eight residential properties with a total of 12 units. Scott also worked for a major bank in the mortgage department, becoming the second-highest performer in the country. With Scott's knowledge and skills, he started his company, LendCity, specializing in residential and commercial lending. LendCity now has a large team and engages in marketing activities.

Overall, the podcast show follows Scott's journey from a troubled childhood to a successful real estate investor and business owner, highlighting their experiences, challenges, and growth along the way.

Thanks for tuning in today. I really wanted to get this show started with a bit about me, how I grew up, where I came from, and what led me to get to where I am today. It was actually a mistake that led me to where I am today, but it was the best mistake ever. So I'll touch on that. I grew up and was born in Lewiston, Maine.

I was actually born in the same hospital that Stephen King, when he had his really bad car accident. It was in the same hospital that I was born at. A cool background there, but I lived in the States until I was four or five. And at that time, my mom and dad, they, they separated. So she remarried. So my new stepfather he was like a broadcaster.

He did like wrestling events and he would always narrate and speak on TV for different things. So Tom Joy of the Windsor Raceway, they sponsored our family to come here, and they wanted my stepdad to work as an announcer for the Raceway. So that's how we got started. So they sponsored us. Very nice family.

They've passed away now, but we're here because of them. So when we grew up, it wasn't always easy. My mom and my new stepdad, they ended up splitting up. There was things that happened and so they were no longer together. So my mom worked multiple jobs to give us food, give us shelter, and she was always gone.

So we always had babysitters watching us. And I was a little troubled child. So the babysitters, they wouldn't last long all the time. We got a new one this week or a new one next week, and we were like those kids on TV where. The parents are calling all the babysitters and no one wants to watch them like Dennis the Menace where nobody wanted to watch Dennis and the neighbors did.

So that's what happened with us, right? Nobody wanted to watch us. I don't think I was bad criminally or on purpose. I didn't necessarily hurt people. I just, I was kinda lost from my. Whole family was in Maine. I left them and then my mom got separated and she's always working. So it was, I was by myself and I got bored and to entertain I would do bad things, nothing too crazy.

It was there. Anyways, with the babysitters, you don't get direction from a babysitter like you would a parent, right? You, they watch tv. They're on the phone with their boyfriend or girlfriend. They're preoccupied. So I got to get out there. And just roam the world and explore things. And I quickly discovered I, I loved exploring and at that age too, I discovered that I liked being my own boss and kept doing my own thing.

I didn't like I. Being told what to do. I always had a problem with authority, not in a super negative way. I just always saw the world as what can I do with it? Not how can somebody tell me what to do with it? So I would explore things. We had a Corey in Amburg. We explored that and we mill made tree forts, me and my friends and it was a lot of fun.

But it, it was a lot of time by ourself cuz we, we missed. Our parents, again, my mom always working, my dad living in another country, so it was a bit of a struggle. So when I was in school, I was getting bad grades. I was told from the teachers that I remember my grade seven teacher telling me that I was not worth the skin I was in.

He said that if me and a friend of mine actually, and little things like that, It bothered me, but not too much. Like I knew that he was wrong. I knew he was really wrong. You shouldn't be telling that to anybody. Anyways, he said it to me and I knew he was wrong and I had to do something about it, but at the time, I wasn't ready to do something about it, so I ended up failing grade six, not from lack of intelligence at all, just from.

Lack of doing my work. I would get homework, I'd get assignments, but my mom was gone working and the babysitter was not, she was not gonna help me do my homework. It didn't get done, so I just got, I failed from not applying myself, but I'm actually, when I look back, I'm thankful I failed because the crowd I grew up with in that younger grade was amazing.

I made so many good friends that we played sports, and it was just lots of memories that stay with you to. To the end of times. So I'm really grateful for being held back and working with that, that new, or being around new kids. So then we get to high school, so same thing, high school. Now you have more workload.

But I didn't apply myself. And I would do like silly little things. Like the one time I brought an air horn into class and I let it go off and obviously that got me suspended and we had a substitute teacher and we were in the courtyard and it was a really windy day and I was bored in class, so I ripped up all these little pieces of paper and the teacher was writing something on the board and in our classroom the screen was broken.

So I threw out all these papers in the courtyard and it looked like a big giant. Like snowstorm, like it was, they were everywhere and the wind was blowing around and stupid. Little things like that I would do just to get a good laugh. And so anyways, I kept getting suspended for all of these little things like that over and over again.

So the principle at the time, he told me, he said, you know what? You've missed, you've got suspended quite a few times. You've missed your reports, you haven't done your schoolwork. He said, I'm gonna suspend you to the end of the school year and then you can come in and you can write your final exam and then be done.

So this was grade 12. So I'm great. I get a vacation and then I can come and do my exams and I'm done school. Cause I really didn't like school. I found that I needed to be doing, I. Not that I didn't like school, but I didn't like being forced to take classes that I didn't want to do. Back to my story, when I said like I discovered at a young age where I liked to be my own boss and do my own thing, it was the same thing with my learning.

I liked to learn, but I wanted to learn things that I thought were gonna be valuable to me or that I had an interest in, and I just felt school was not that it for me. I always had the entrepreneurial mindset from when I was six or seven. I just always wanted a business. I always wanted to do something like that.

So anyways, back to the school story. So I go in the last day there to write my exams and the principal, he's outside waiting for me and I go up, I'm trying to walk by him cuz he's the last person I wanna see. And he's, you know what Scott? I looked through the attendance and with your last suspension, cuz it was about three weeks he suspended me until the end of school.

He said with the three week suspension and the previous ones, you've missed too much school. So you're expelled. You can't even finish your exams because you're no longer a student. And I was actually quite upset at the time because I feel like. He knew that like he did that on purpose. He didn't want me to be in school and that was his sort of slimy way of getting me kicked outta school.

Cuz all the things I was doing, it wasn't super bad, but it was annoying to him. I'm sure it was silly, funny things, but that was his way of kicking me out. So I was upset, but I took that as a learning point and I did quickly discovered that you can't really trust. People, even people of authority, because I had trusted that I'd be able to go back into school and do it.

But really, I discovered he set me up so I was kicked outta school at that young age. I discovered quickly that you can't always trust people, not to see people can't be trusted, but you just have to be careful with trust. Now we have to take a quick break, but when we come back, I'm gonna show you what I did, how I learned, how I developed, and how I grew.

I. And got past all my childhood issues, trials, tribulations, all that stuff. All right, welcome back. So I got kicked outta high school, and then I'm looking at my life and I'm like, what am I gonna do? I have friends that are doctors or want to be doctors, veterinarians, teachers, and I'm kicked outta high school.

What am I gonna do? So right away I got into sales because with sales it was outta my own business. Cause I could write my own paycheck based on my effort. And it worked. It worked really well. I worked at Sears. It was like a dealer store which sold all appliances, tractors, beds, TVs, all that stuff.

So I sold that. I was there for a couple of years, and then I got a job in Windsor at a call center selling high speed internet TV services, that type of thing. And I quickly became one of the top sales reps there. And then I had this crazy idea that I was going to apply for jobs all across Canada.

I didn't care where I got a job, but I just wanted something new I wanted to apply and I was just gonna go wherever it was and move on. So I met my wife, and then I, somehow I can convinced her to come with me in such a brand new relationship. She agreed and we moved. The job was in Sarnia, so it was only two hours away, which was great.

So I got the job there. It was at Future Shop and quickly I did exceptionally while there, they invited me to, whenever they opened up a new store, I got to go and help sell out those things. Whenever they did the home shows in Toronto, they invited me on behalf of Future Shop to go and sell their appliances there.

So quickly, like every sales job I ever had I was always the top. I even won awards there with the most improved store and the best appliance sales department. So then I. With that extra money and the extra savings coming in. I started reading a book called Rich Dad Poor Dad, which gave me the idea of investing in real estate.

I got creative and I signed up for a couple of their courses. They had some courses in Canada. It was. 10 grand for a wholesaling course and a rent to own course. So I went and I did those courses. And in the wholesaling course, ultimately you find a property that's at or below market value and you present it to investors and they buy it and you make a little bit of money and you didn't have to do much.

You just find the property and get paid. So I started off my investing doing that. So I met this guy outta Toronto and he said, listen, Scott, you find me the place. And I'll buy it and I'll share the profits with you, which is even better than an assignment fee. If I find the home and I assign it to someone else, they pay you a fee.

So he's willing to split the profits with me, which is even better. So I felt like I struck gold. He tells me, find the house, put it in a cash offer, give it to him, and he'll buy it. So I'm like, okay. So I found this house. I was on Ross Avenue in Sarnia. And I get the firm offer. It's fully accepted. I present it to him.

He's gone. Crickets. He won't reply to me anymore, nothing. So I'm sweating bullets because I put in a firm offer on this house. I'm a young guy, right? I wasn't even pre-approved for a mortgage. I didn't even have great credit at the time. I was just building things up. And so I went to the bank and actually I was surprised, but I was able to get approved for the mortgage.

That was the mistake that changed my life because I was not anticipating buying this property on my own. I only got it. Because this guy said that he would buy it. So anyways, overnight we were forced to turn into real estate investors. The home needed everything. It had a gravity, furnace, knob, and tube wiring holes in the roof.

It had plaster mortar, and it was damaged everywhere. It really needed everything. Like we had to do flooring. Bathroom. The weirdest thing was the kitchen cupboards were brand new. That was the only thing in the house that was brand new. Everything else needed to be done. So it was a great project for us because not only was it our first accidental investment, but we needed to do everything.

So thereafter, all the future investing that we did, we were not worried about how the property looked or what happened. Long story short, I ended up. Doing really well with future shop that they wanted me to transfer to Windsor. So we got pregnant as well at around the same time. So we moved to Windsor and once we moved to Windsor we had to buy a home to move into and we got a duplex.

So we started then growing a real estate investment portfolio. We kept the home in Sarnia and we grew. So we got up to eight residential properties. I believe it was 12 units combined. And at the time I was working for a major bank doing mortgages. So there I quickly got to be number two in the country.

So I took that skill and the knowledge and the understanding of doing mortgages and I started my own company cuz that was my goal ever since I was little. I always had to have my own company and working at the bank was great. But there was a lot of restrictions. They wouldn't allow me to do some of the creative things I needed to do to grow my business.

They also, it was hard to get approvals for client, whereas a brokerage, now we have access to banks. But we have all the other lenders as well. So the clients have so many more options now. So anyways, started Lend City. So that was the first entry into commercial lending, or sorry, commercial invest. We've got that going on now.

We've got a large team supporting us and we do a lot of marketing and things like that. Along the way to, with what I learned at the bank was I got to see the bank required that every investor. Supply their assets. So if you own three or more rentals, you had to show them that you had a hundred thousand of liquid funds, which was assets, really, assets or savings.

So by being at the bank, I got to quickly see what investments clients owned, what ones worked good, what ones were bad. I got to learn the strategies and the tricks. That investors were doing to grow their portfolio and make more money. And I took the best of that and I applied it to my own investing portfolio.

So this is outside of real estate. I purchased stocks. I know I'm gonna have episodes about this, but I've discovered there was a way that you can purchase stocks direct through many of the companies without a trading fee, and you even get a discount. On the stock when it's a dividend that gets reinvested.

So I'll show you how to get discounts on stocks when you buy direct through the companies. There's many different products and platforms that I used to grow my net worth really quickly with really low fees that were much better than what the bank products could offer. No, I'm not a financial advisor.

I'm just gonna share from experience, but I will be bringing my financial. Advisor, friends on to talk to you about what they do to help grow their client's portfolios. But also I believe in personal development. So this whole time I've been reading books, think and Grow Rich Dare to Lead. There's all kinds of different books that I've read that have helped me to grow and develop into who I am.

Better productivity, better sleeping. All of these things we're gonna be diving into when I interview experts in these fields. We're also gonna have people that you can meet that had a similar story to me, but different that grew up, had a plan, developed and accomplished their goals. So we're gonna have a slew of people on here, but I wanted you to know where I came from.

Everybody was counting on me to fail. I learned, I saw people grow and develop. I wanted it. I moved forward with it. And everything that I've ever wanted, or everything that I've ever wanted to accomplish, I've done. So now my goal is to be the biggest online mortgage brokerage in Canada. And we're gonna be, we are local here in Windsor, but we cover.

All of Canada through our partners, and so that is our very next goal and what we're working towards. But we're here to help you grow. Make sure you tune in to next week's show because we're gonna be diving into leverage what it is. What it means to you to leverage and how most wealthy people got to where they are by leveraging.

So we're gonna show you how to take the risk out of leveraging and use what I like to call calculated leverage, and that's gonna be the foundation. Of the show going forward. And once you learn those ins and outs, it's really not tricky and it's really not really risky. It's incredible how much risk gets taken out of the equation when you use calculated leverage.

So we'll discuss that more on the next show.