The Wealthy Barber Podcast - #15 — Gerry Dee: Lessons Learned From Comedy, Athletics and “Mr. D” (15ish Minute Money)

Episode Date: April 22, 2025

Our guest this episode is the legendary Canadian comedian Gerry Dee! You know him as the creator and star of “Mr. D” and the host of “Family Feud Canada”—but did you know “The Wealthy Barber” is one of the five books he’s ever read? In this 15ish minute episode, Gerry sits down with Dave to talk about the lessons he learned during his early career as a teacher, his leap into stand-up comedy, his big break with “Mr. D” and how all of those experiences shaped how he thinks about money. Tune in for laughs, insights and a fun dose of nostalgia!    Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Gerry Dee (02:14) Gerry’s Early Life (04:20) Gerry’s Career as a Comedian & Entrepreneur (07:56) Lessons Learned From Gerry’s Athletic Background (12:16) When Gerry’s Career Took Off (13:43) The Story of Mr. D (14:33) Gerry’s Investing Approach (17:41) The Best Investment Gerry Ever Made (18:17)  Does Gerry Follow The Wealthy Barber Principles? (20:08) Conclusion

Hey, it's Dave Chilton, the wealthy barber and former dragon on Dragon's Den. Welcome to the Wealthy Barber Podcast, where we'll be hosting some of the top minds in the world of personal finance. Yes, that's to balance me out. The podcast is about making the subject not just easy to understand, but dare I say, even fun. Honest. Whether you're trying to fund your retirement retirement figure out how to build a down payment

Save for your kids education manage debts, whatever will be here to help you do it Before we jump in a quick but important note. Nothing. We discuss here should be taken as investment advice We don't know you and your personal financial situation. So we're not here to tell you where specifically to put your investment dollars we're here to educate get you thinking and we hope entertain but please do your own research and or consult with your financial advisor before taking any action hey it's dave chilton with the wealthy barber podcast to say i'm excited it's an understatement one of my favorite people is on the show today jerry d i think the funniest guy I know. I mean, very few people can make me laugh like he can.

I'll tell you a quick story about Jerry to start it. I bumped into him in Ottawa 12 years ago. We're checking into a hotel. I'm giving a speech. He's doing an event that night. He says, drop by. I said, no, I wouldn't want to walk in late. That'd be rude.

I'd have to walk in 10, 15 minutes into your act. He goes, no, no, no problem. I walk in 10, 15 minutes late in his act, he picks on me the entire time. How rude of you to walk in and disrupt this, you're throwing off the crowd, you're throwing me off. What a horrible person. I thought we could do that, I just don't remember. Horrible, horrible person.

I'm happy to be running into you because, you know, wealthy, I didn't read a lot of books. I mean, I've talked about this, you know, before. I'm not a big book reader. I could tell you the books I read. I read the Life Story of Jim Carrey. I read Michael J. Fox, Lucky Man. I read Tuesdays with Morrie, which is not a very funny book. I read Gretzky's Life Story and I read The Wealthy Barber.

And that's the truth. Those are the five books I've read. I've tried to read others but man, it just takes, you got to get me quick like right away. But always had an interest in, you know, I talked about this in my book. My parents, my dad was a bus driver. My mom was a state home mom slash dental assistant kind of back and forth.

And money wasn't something we had to talk about in an investing sense. My dad and mom lived paycheck to paycheck and we had a great life and great parents and everything was great. So I got into a golf club called Baby Country Club when I was 14. And you know, as you know, these private clubs are very expensive.

But it was a sponsored program. It was $150 for the summer to golf. All you could golf. And I think I ended up playing 130 rounds every summer. Wow. What it did was it opened my eyes to a world of wealth, to be honest. And I didn't know about, you know, and anyone that's grown up in a, you know, a world I did, you know, lower socioeconomics, it's things you don't see. And I was seeing these things and it motivated me for some reason. I didn't

know what I didn't think much of it. But fast forward to 30 28 29 30. I'm a teacher. I'm very happy. I'm making my 40 50 60,000 a year. But again, I keep running into these people that had a lot of money and it some way you know you you you think how could I get that so it was kind of just a 30 years old I thought I want to trust it like I thought what can I do to kind of be more successful so you know but I was very proud as a teacher to buy my first condo and put a deposit down a lot of the information from your book that stuck with me and like investing, take 10% and the compounding interest, all

the things I... You should learn in school. We don't do enough financial literacy in grade school and high school. We really don't. That was kind of start. And then the comedy, for some strange reason, I thought I could go into comedy and that'd be the way to make money. And I mean, I got lucky, but it's really not something to think about. You know what I want to do to make money? I want to be a comedian.

It's really not the angle, but it worked, luckily. Yeah, I don't think it's luck though. I mean, A, you're very funny, but the other thing people don't know about you is you're an outstanding entrepreneur. Like you control most of the projects you're involved with, whether you're the producer of Mr. D, whether you're running your own events, like you are very hands on in terms of taking advantage of your brand, spreading the word, etc. Talk a little bit about why you've been more involved than some of the other comedians

and some of the other artists out there. There's comics in Canada a lot funnier than me. It's just not a star system here that we have. But I found right out of the gate, I was very business oriented for some reason. I'd stand at the back of the clubs and we called it, I would whore myself. I don't know if that's politically correct. We'll leave it in. We'll leave it in.

And I would hand out flyers and here's my next show and I'm gonna give you the financial of it. When I was, you know, my first gig I got $10 and two drink tickets. But there was nothing like getting paid to do something you love. And it was like, it was a moment of, as stupid as it sounds, it was a moment of I'm a paid comedian.

And it was $10. You know, and then I'd get gigs. I started at Yuck Yucks and I'd get gigs for $150. So for me, David, I was teaching all week. I was also running a hockey school, which that helped too, but I was teaching all week. I was also running a hockey school, which I, I, that helped too, but I was teaching all week and, um, then I had another three gigs, another four 50. Right.

I'm like, this was like found money to me and I loved it. And then that number just so motivated me. If I get better, I'll get more and everything goes up, you know, everything goes up, but then I called up Mark Breslin. I said like, you know, how about instead of paying me, you know, $300 to headline a show, which, you know, was for me, I was doing seven shows on a weekend. Yeah, that's very good. 100 plus I was teaching. Yeah, I was doing okay.

I was like, absolutely. I was doing okay. I was like, but for me, I said, how about if the ticket $17 because I wasn't getting behind the shows at yuck yucks, right? It wasn't I was but it wasn't the motivation was like, why am I getting anymore? And market businessman and I and he said, I said, I'll tell you what, how about we charge 22? I take the five and I'll push the crap out of it. I'll help. He was smart. He's like, that's a win for me. You know, get my 17, you're getting another five plus your 300.

So now he's getting, you know, 80, 90, 200 people at a show. And it started to just take off a bit. And I always try to stay clean. I think that that helped when I would, because I would help with corporate work. And it was easy to book me. For Yuck Yucks, it was easy to book me. Because they could send me anywhere and there was gonna be no worries.

You know, I could do any type of group. And they were like, he's not gonna talk dirty, he's not gonna swear. So I got a lot of gigs. Which- That's where I first met you, is the corporate work. You were huge on that and you're right. You stayed clean.

It was a great business idea. And I mean, Mark is an entrepreneur, obviously. He probably loved the fact that you were willing to go out and push it. Hey, I want to go back to something. You talked about the hockey school. A lot of people don't know that you're a very good athlete. You played university hockey, which is outstanding hockey. You're a very good dancer, kidding aside. Like I've seen you dance. You're very good at that. Did your athleticism

tie into this at all in terms of competitiveness and those types of things? That's a great question. When I was a walk on at St. Effects, I said same thing. I want to play university hockey and I had no business thinking that. I had done my degree at York so I was a bit older and I had been sort of tearing up this intramural league which was full contact. And I said I'm going to go and do my teaching degree at St. effects and I walked on. I made the team and I was like first line, first game I'm standing at the center of ice and I got four points and I was like what's going on here?

But it caught up quick like you quickly realized that I probably wasn't good enough to stay up there and I eventually moved to the fourth line. But what it taught me about the business I'm in is I got cut. I got cut my whole life from teams. I learned failure quickly. I played a high level golf as a junior. Golf's the most, it's the toughest thing on you every day. So

when I entered this world, I found a couple things. I learned this from my mom too. I was thanked people at the end of gigs. I was like, I would send them an email and I knew that could lead to more work. And it was also just the way I was raised. Like, thank you for having me, and the meal was great, whatever, simple things that take two seconds. And in sports, I learned that there's a lot of failure. And in comedy and entertainment, there's a lot of failure. And you have to handle it well. And I've seen people in my business pitch a show,

not get it, kick up a tantrum. You don't know what you're taught, they never work again. And I think one of the things I'm most proud of is, sure there's people that don't like me in the business or whatever, and I don't really care, but I know I've maintained good relationships with good people, and especially the executives

in the networks, and that's people that I know don't have a problem working with me because I've always been professional. I've pitched a bunch of shows since Mr. D and they don't get greenlit. But I don't kick up ruptions. I get the business. I get how hard it is for CBC and Netflix and these companies. I know how hard it is for them. So to be a baby, you know?

And when I got cut from St. Effects, I was 23 years old. I thought it was the worst day of my life, because all your teams, my roommates were all hockey players. I was going nowhere with hockey. But the coach of the team was my roommate's father. My roommate was one of the best players. He was the son of the coach. And all the father. My roommate was one of the best players. He was the son of the coach. And all the other guys that got cut,

all the veterans are like, this guy, he didn't know what he was doing, which is what we typically tend to do when we're fired, when an agent drops us. For sure. And I walked up to his house. I said, look, I'm, you know, that I agree with it or I'm happy about it,

but you've treated me well. I'm great friends with your son. I've been in your house for dinner. I don't want that to change. I knew it was hard for him. We often look at the person firing and think of us. That's right. And I think of when my agent in LA dropped me,

I did the same thing. I said, look, I know that's not how it turned. We planned it, but appreciate your time and effort. He wrote me back. He goes, wow, that was classy. I don't think people do that. And it wasn't to kiss ass, it was just like, this guy's not happy he had to fire me.

So we always think of what treats us. I think of, I don't think that person enjoyed it either. I'm gonna take a little bit of the burden off them. We're good. And you know what, often you run into them again. And they remember that. So it's just, I think I've been good at managing that side of it.

And I've had to fire people and no one likes that and people hate you and you know, it's the same when I discipline kids teaching. You gotta send kids to the office. They don't like you. There's kids out there that go, I hated them. Yeah, cause I probably disciplined you. Right? Or it's kind of the way it is. They don't like you. There's kids out there that go, I hated them. Yeah, because I probably disciplined you.

It's kind of the way it is. And a lot of jealousy in the world. So you have to maneuver your way through who's jealous and who's happy for you. And now, before we get to talking a little bit more about investing in money, one quick question. How big was Last Man Standing for you? Did it elevate your profile a lot and led to the Mr. D's of the world? Yeah, Last Comic. I know what you mean. Yeah, Last Comic Standing. Last Man Standing for you? Did it elevate your profile a lot and led to the Mr. D's of the world? Yeah, last comic. I know what you mean.

Yeah, last comic standing. Yeah, that changed. It was a game changer. And there's another example. I auditioned season two. I didn't make it. I kept in touch with the producers. Not in an annoying way because I've seen people do that. Season 3 was a celebrity one they redid. Season 4 I auditioned again. I got a little further, didn't make it. I just kept going back to the drawing board. I wasn't like screw you guys. You know I went back season 5 and I came third. It changed my life because sadly the Canadian Air Term entertainment industry often likes you more

when you've done something in the US. It's very true. It's kind of like, oh, you're on dragons and if you were on shark tank, well, it's like, whoa, it's just the way it is, right? The big entertainment industry there is just bigger. It's not better, it's just bigger. So it helped a lot. And then I went from that to the score, which they gave me a great chance there and did

that, my sports interviews. And then Mr. D was the big break. Again, people know, and then Mr. D was, you know, the big break that, again, people know the story of Mr. D. It was turned down. And I called up the CEO, the president of CBC, and she said, you know what? Okay, let's give it another shot. And that got turned down again, and I just kept kind of fighting for it. But to go away and sulk in the business world doesn't get you very far. Well we're all glad you kept fighting because Mr. D is truly a legendary show. I mean I remember so many of the scenes there. I was saying to you off air that I just went away with a bunch

of retired teachers on a golf trip and they can quote your show chapter and verse. They loved it. My son loves it. It was so many funny moments. So thanks for that. You had a great cast. I know you had great writers but you you had a great cast. I know you had great writers, but you also had a great cast. And nice people. A lot of your cast members are very involved in the charity events I attended out in the community.

Okay, let's move on to investing. You once casually mentioned to me, we were chatting years and years ago, probably 12 years ago, that instead of using an ETF or index funds, you tended to use fairly concentrated portfolios for stocks for your equity exposure. Have you stuck with that and what drew you to that approach in the first place?

Well, I didn't know what I was doing to be honest. I had two, the smart thing I did was I got a proper financial planner. Then I said, I'm going to do some of my own because I'm pretty good at this. I think that portfolio is down like 85%. So his is up probably 85%. I've got all these duds. He did it the right way and I just went, my buddy called, you should buy this mining stock. Really?

Okay, fear of missing out. I'm going to buy it because I knew a little bit about the stock market, which is the worst to know a little. That's so true. You're better to know nothing. Then Bre-X was happening back in no one ever and I remember is like and I knew a guy That bought anything got out but he didn't understand private private. He had the dad fun It was all bunch of things, but I was always waiting for that next Brix. I remember Blackberry my brother-in-law stopped me

I was like this he goes Jerry right now the Blackberry stock. I Don't know how he phrased it. He's in the banking business. He said the BlackBerry stock right now, when it was so high, would mean everybody has 12 BlackBerrys. It was way over and then it tanked, obviously. So … Jare, I still use BlackBerry. You do, eh?

I still use it. I'm the only man. You kind of have to, right? Because it's all telecrypted or whatever. Yeah, and it's all Waterloo, baby. I'm loyal to the hometown. Oh, right, right. I'm speaking of Waterloo, I just announced I'm in Kitchener October 18th, so I have to

get you tickets. Yeah, you're in the center of the square? Good, I'll come over for sure. I think it comes out today, actually. I don't know when this airs. So for me, to your question, the best thing I found was real estate. Like you buy the equity on our first house, and then that allows us to buy this house and now this house is probably doubled.

I got a good life insurance policy. My dad used to work for Standard Life and he always said, get a life insurance, get a life insurance. So I've set my family up that when something happens, I think that's the most comforting thing. I'm proud that I did this without my parents. Like I've helped my parents, it's been reversed. They never had this opportunity. So I'm happy that it's kind of a, you know, if I look at it objectively, it's like, I still can't believe some of

the things that kind of, how my life evolved financially. But I made some, I thought, IPO, everybody calls me with an IPO, and I'm, yep, yep, yep, yep. And one worked. One worked, and thankfully it worked. What's the best investment you've ever made outside of your house? Well, outside of my house, yeah, it was a buddy of mine out east called me and offered me this. They were startup and I did it and it did extremely well and I got, you know, they got bought out and

you know, I think you call it like a 10-bagger something. That would be, a 10 bagger would be my best. And it balanced out the six I was wrong on. So I live in a net world of zero. Now do you do all the common sense wealthy barber things like you max your TFSA as does your spouse, your RRSP, you had RESPs for the kids. Have you done all those things through your planner? RESP, I'm going through that withdrawal right now. RSP is the smartest thing,

easiest smartest thing you can do if you can because it's free money. Free money. TFSA, I did it, I had to take it out because I bought a property and I took that out but that's another no brainer. RSPs, a little different because I'm corporated. I don't know how that works.

I have a great accountant in my buddy Dwayne that I played hockey with, but for the most part, the land, the properties, I know, is what I, you know, my parents, we bought my parents a condo So when my dad moves out of that my mom passed away or when whenever that happens, there's a bit of investment there So I've kind of got future investments. So I think that's kind of them You know, is it true that you charged your father dramatically above market rent because that is the rumor. Yeah, there's no rumor There is now. I just started it.

I'll tell you a really funny story about my dad. Well, I'll leave it. So I think property for me has been the best other than just getting that and just kind of having things that are liquid. If I liquidate them, I'll be okay. So I never worried about money. I saw my parents do it their whole life. And I thought, you know, I remember once saying it's only money, like it's only money.

I remember just thinking that it was, you know, I'm not gonna sit and worry about money every day. These days it happens. Sure, obviously. I always feel like I can find a way to generate revenue. Now you're going to keep working, right? Like you're not the type to retire, why would you? You love what you do, you're enjoying doing family food.

Family food's a great gig, eh? I mean, I'm sure you don't even tape over a long stretch. Love it. It's just, I love it. The family's everything about it. Well, you do a wonderful job. I mean, your dry humor. Sometimes your humor really catches the people off guard. You could tell they weren't quite ready for it. Well you do a wonderful job I mean you're dry humor sometimes your

humor really catches the people off guard you could tell they weren't quite ready for it. I think you're fantastic on that show. It's a lot of fun. Look I'm really blessed in a lot of ways with you know how great CBC has been to me and how great you know the friends I've met along the way and Mike Volpe my partner on Mr. D just became you know one of, the friends I've met along the way. And Mike Volpe, my partner on Mr. D, just became, you know, one of my best friends. And I met great people. When you work with great people,

you, great things can happen. I've been doing that. Well, you're a very nice guy. You're a very classy guy. I think you've got good relationships, but you've also got a great reputation. Everybody I know who knows you, likes you, speaks highly of you, should be proud of that.

I'm one of your biggest fans, as you know. Oh, thank you. I come and see you speak a lot, love highly of you, should be proud of that. I'm one of your biggest fans as you know. I come and see you speak a lot and love it. I love what you do and you know, it's, no, I'm glad we could do, I don't do a lot of podcasts but when you asked I'm like for sure. Well thanks again and we'll make sure we get you back on. Bye bye. Thanks guys.