In this episode of The Huge Transformations Podcast, host Sid Graef sits down with Dan Gibbons, co-founder of Shine Window Cleaning in Toronto, Canada. Dan shares his journey from a college student in a painting program to bootstrapping Shine with his partner and growing it from zero to $6 million in under seven years.

The conversation explores Dan’s entrepreneurial roots—from shoveling driveways as a teenager to knocking doors in the freezing Canadian winter—and how those lessons shaped his approach to growth. Dan reveals the systems, partnerships, and mindset shifts that fueled Shine’s rapid rise, including a strong reliance on door-to-door sales early on, transitioning into digital advertising, and focusing on dense local market penetration rather than premature expansion.

Listeners will gain insight into the realities of scaling a service business, including the importance of delegation (not abdication), the role of mentorship, why belief and resilience matter more than “hacks,” and how to prepare for the leap from owner-operator to true business leader.

Resources:

Transcript:

got it — here’s your transcript split by speaker, fully unabridged (no edits to wording or punctuation).

SID:

Hello everyone. Welcome to the Huge Transformations podcast. I’m Sid Graff outta Montana.

GABE:

I’m Gabe Torres here in Nashville, Tennessee.

SHEILA:

And I’m Sheila Smeltzer from North Carolina, we are your hosts and guides through the landscape of growing a successful home service business. We do this by interviewing the best home service business builders in the industry, folks that have already built seven and eight figure businesses, and they want to help you succeed.

HOST:

Yep. No fake gurus on this show. Just real life owners that have been in the trenches and can help show you the way to grow profitably. We get insights and truths from successful business builders, and every episode is 100% experience, 0% theory. We are going to dig deep and reveal the good, the bad, and the ugly.

HOST:

Our guests will share with you the pitfalls to avoid and the keys to winning. In short, our guest will show you how to transform your home service business into a masterpiece. Thanks for joining us on the wild. Journey of entrepreneurship. Let’s dive in.

SID:

Hey my friend. Welcome back to the Huge Transformations podcast. This is Sy, and today’s episode is gonna be a ton of fun, and here’s why. My friend Dan Gibbons. Whom I met at the huge convention last year, introduced us to our keynote speaker this year. But he’s got a really interesting backstory from a college kid that worked with a painting company to getting a wild haired idea with he and his girlfriend said, we should start our own window cleaning company in Toronto.

SID:

So. Normally when someone starts their own window cleaning company, they struggle and stress and they grow nice and slow, and it takes a few years to get to a half a million or whatever. They did a half a million their first year, a million their second year, and then they’ve continued the growth of a million dollars additional revenue every single year they’ve been in business.

SID:

So they went from zero to 6 million in under seven years, and I want you to listen in on this conversation and find out and understand how they did it. Because it’s not normal. Dan’s very generous. He’s got a lot of energy and we kind of bounce around all over the place. I hope you enjoyed this conversation as much as I did, and I hope you learn as much from it as I did.

SID:

Also, thanks for joining us on the Huge Transformation Show. Please meet Dan given and thanks for joining us at Sid g Graff and this is a huge transformation podcast and it’s rare when we get to do it live and in person. Usually it’s on Zoom, all stuff. But today we’ve got Dan given with this Dan. Check out the hat, look at that camera over there.

SID:

Shine window cleaning in Canada. And, uh, Dan, you’ve got a, you’ve got a fast growing window cleaning operation in Toronto, right?

DAN:

Yep.

SID:

Yeah. Tell, tell us a little bit about like, well, when did you start?

DAN:

Um, I started Shine, uh, we started shine seven years ago, so this is year seven. Uh, but I’ve been in, in the game, so to speak, for about just over a decade now.

DAN:

I started in, in university doing like a student painting program, and then I realized I could go out on my own. And here we are.

SID:

Do you know anybody else that start with you in that student painting thing? Did they go out on their own? Do you know anybody else that started their own painting?

DAN:

Um, it’s an interesting program because, uh, when you go into it, you’re, you’re a bunch of students.

DAN:

There’s like 200 students across Canada doing it. And, um, you’re in the program and you’re all hyping each other up and you’re in school, so nobody’s doing anything. And so you guys are like, doing something. Yeah. And, and you’re, you’re convinced you’re all like these crazy entrepreneurs and everybody puts like entrepreneur in their, in their Instagram buyout.

DAN:

Um, and then you realize when you leave that maybe like 5% of people actually go out on their own. Most of them end up going for like really high performing jobs. ‘cause now they’re, they understand systems and they’re very capable. Um, a lot, some, I would say. Maybe 10% try to do something on their own, then they realize it’s not for them, and then a small percentage actually end up doing it.

DAN:

And um, I mean I think that’s just a testament to like most of life, which is, you know, you gotta figure out what what you want by doing it. But yeah, I have a few friends, I would say a couple that like are very successful from it and a bunch that just kind of went out and realized it wasn’t for that.

SID:

Right. Was there a time, like when you were a kid, what was your first kind of. A real thing or sell some things. Did you like sell cookies or any of the stuff?

DAN:

Um, I, what was my first thing? My first thing was probably, uh, shoveling driveways. That was like my first independent thing, and I would always try to, before that when I was like six, I would always tried to harass my dad and be like, how much can I make to take out the trash?

DAN:

You live here, take out. He’s like, you get to continue sleeping. So, yeah, right. I said, alright. Um, and so, and so my first thing was I was probably like 15 and I convinced my neighbor to go knock on doors with me, uh, and shovel driveways. And, uh, that was my first lesson in, in partnerships because, um, I got very discouraged when he didn’t want to go out with me.

DAN:

So after like two nights of knocking on doors, he, um. He would, he would just keep saying, yeah, I don’t want to go tonight. I don’t wanna go tomorrow night. And, and then I wouldn’t go out. And so I was dependent on him to go out. ‘cause in my mind I was like, I’m not gonna do this thing alone. And then I stopped knocking on doors.

DAN:

And later in life I realized, oh, that was not, it wasn’t that I should have stopped it was that I stopped because I was relying on someone else who I shouldn’t have been. Like, who wasn’t driven to do that with me. Yeah. And. Um, you know, if I could go back and talk to my yourself, I’d be like, no, you need to go do this because you’re alone and that’ll make you better.

DAN:

So that was, that was the first thing. And then there had been a bunch of, like, I like sold weed to my friends. Um, and then I started student painting and I realized that it was much more legal and profitable. Um, and, and then that was when I got hooked. I became, I, I changed my whole life when I, uh, I started becoming addicted to, um, to realizing that I could put in work.

DAN:

And get a direct correlation of results for that work. And I went from sleeping in until 10 o’clock in the morning and smoking weed all day and, and staying up late to just being up at six in the morning and working all day till 10, 11 o’clock at night and not taking days off. Um, which ended up being a hard habit to break later.

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