From Broke Kid to $1B Mortgage Expert: Scott Dillinghams Story and What This Show Will Do for You

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. 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 separated.

The Core Idea

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 families. 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 times, 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.

Deep Dive

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 kind of lost. My whole family was in Maine. I left them, and then my mom got separated, and she's always working.

So 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, a parent, right? You, they watch TV, they're on the phone with their boyfriend or girlfriend, and they're preoccupied. So I got to get out there and just roam the world and explore things.

Practical Steps

And I quickly discovered I loved exploring. And at that age too, I discovered that I liked being my own boss and doing my own thing. I didn't like 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 in it. So I would explore things. We had a quarry in Amherstburg. We explored that, and we made tree forts, me and my friends.

And it was a lot of fun, but it was a lot of time by ourself because 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 of me and a friend of mine, actually.

Key Takeaways

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.

We played sports and it was just lots of memories that stay with you to the end of times. So I'm really grateful for being held back and working with that new, or being around new kids.

Resources

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 at all these papers in the courtyard and it looked like a big giant 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 principal at the time, he told me, he said, you know what?

You've missed, you got suspended quite a few times. You've missed your reports.

Introduction

You haven't done your schoolwork. He said, I'm going to 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 because I really didn't like school. I found that I needed to be doing, 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 like 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 going to be valuable to me or that I had an interest in. And I just felt school was not that 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.

The Core Idea

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 because he's the last person I want to see. And he's, you know what, Scott?

I look through the attendance and with your last suspension, because 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 out of school because all the things I was doing, it wasn't super bad, but it was annoying to him. And 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.

Deep Dive

And I 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 out of 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 going to show you what I did, how I learned, how I developed, and how I grew and got past all my childhood issues, trials, tribulations, all that stuff.

All right, welcome back. So I got kicked out of high school and then I'm looking at my life and I'm like, what am I going to do? I have friends that are doctors or want to be doctors, veterinarians, teachers, and I'm kicked out of high school. What am I going to do?

So right away, I got into sales because with sales, it was I own my own business because I could write my own paycheck based on my effort and it worked. It worked really well.

Practical Steps

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 going to go wherever it was and move on.

So I met my wife and then I somehow I 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 well 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 the appliances there.

Key Takeaways

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 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 out of 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 in a cash offer give it to him and he'll buy it.

So I'm like okay. So I found this house that was on Ross Avenue in Sarnia and I get the firm offer it's fully accepted I present it to him he's gone.

Resources

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?