Mike McKay
January 1, 2025

In this podcast, Rich Hewitt shares his journey into entrepreneurship and his experience with Dumpster Dudez, a franchise he joined after a career in the security industry. Growing up with a passion for business, he always dreamed of owning his own company. After researching different franchise models, he was drawn to Dumpster Dudez due to its service-oriented approach and simple business model. Rich highlights the company’s commitment to residential customers by offering dumpsters that fit easily in driveways, providing personalized service, and using smaller trucks that can access tighter spaces. He emphasizes the importance of problem-solving, from managing truck maintenance to addressing customer needs, which has been crucial in his growth as a business owner.
Rich also discusses the value of networking and building relationships with other small business owners. He recalls how referrals from strangers and collaboration with businesses like Junk It With J played a key role in growing his business. He offers advice to new entrepreneurs, encouraging them to take action and engage with potential clients consistently. Looking ahead, Rich is focused on scaling his business, balancing investments in equipment and personnel, and ensuring his company can meet growing demand. With steady growth and careful planning, he is excited about the future and the opportunities that lie ahead.
Podcast Transcript:
Mike McKay: Hello, everybody. This is Coach Mike, and I’m excited to have Rich Hewitt from Dumpster Dudez with me today. Rich has hobbies that include cycling, spending time with his dogs, and recently taking up target shooting. He’s also been exploring the zen of cleaning weapons, which I’m sure we’ll touch on. Rich is a fairly new entrepreneur, so he’s learning the ropes of how to balance giving up hobbies while also finding ways to get back to them. I’m really looking forward to our chat today. Thanks for being here, Rich!
Rich Hewitt: Thanks, Coach Mike! I really appreciate the opportunity. I’ve enjoyed our conversations so far and I’m excited for what’s to come today.
Mike: Alright, let’s dive in. Tell us a bit about your personal story—where you’re from, where you live, and anything else that shapes who you are today.
Rich: I grew up in Whitefish Bay and went to school at Whitewater. After college, I worked for ADT Security in the electronic security industry. After that, I got married (I’ve been married for a long time), and we have a couple of kids. My daughter just graduated from college, and my son is still in college. We also have a seven-month-old German Shepherd puppy, which has been a bit more work than we expected, but we’re managing. As my wife says, the dog is smarter than us!
Mike: It’s surprising how much effort our dog requires—almost as much as our kids used to! And we just have a little ankle-biter of a dog. Anyway, what’s a funny story that your family loves to tell about you?
Rich: There are probably more stories than I can remember! My family likes to poke fun at me for being known as “Mr. Safety and Security.” I think that comes from my background in the security industry. I’ve always been focused on safety, and I try to pass on those lessons to my kids. The funny part is that these stories often pop up at family gatherings, especially during the holidays, and they’re usually ones I don’t even remember. But everyone gets a good laugh out of it!
Mike: That’s great! Now, let’s talk about your journey to becoming part of Dumpster Dudez. What inspired you to think you could run your own business?
Rich: I’ve always wanted to own my own business. As a kid, I had a lawn business with a friend, doing lawn care, snow blowing, paper routes—just the usual. By high school, I was cutting 14 lawns a week on top of a full-time job. In college, I studied franchises, even doing two independent studies in economics where I focused on franchises and business. It was actually a really cool experience. My professor let me follow my own path, and I learned a lot. After college, I knew I wanted to run my own business one day.
Fast forward to last February, I told my wife, “It’s time. I need to do something.” I didn’t know exactly what that something was, but I knew it had to be a franchise. I spent time narrowing it down and decided on a franchise model because of my background in sales, leadership, security, design engineering, and operations. I knew the importance of good marketing, processes, and standards, and I didn’t want to spend years figuring all that out on my own. So, I reached out to franchise consultants and started my research.
At that point, I was fully focused on this new path. I had a great career, but I knew it was time for something new. As I researched, I came across Dumpster Dudez while watching YouTube videos about dumpster companies. The business model fascinated me. I’d heard someone on YouTube talk about how there’s money in “boring” businesses, and that stuck with me. When I found Dumpster Dudez, I was sold. I reached out to them, and one Sunday afternoon, we were having a conversation. I told my wife about it, and she was surprised at first, asking, “Are you sure?” But once I explained the concept, she understood. And that’s when we decided to move forward.
The key for me was knowing I wanted to get into a service-based business that was easy to understand—something I could replicate. I came from a very complex industry, so I wanted something straightforward. Also, the dumpster industry wasn’t known for great service, and Dumpster Dudez had a model built around providing excellent service. The company was founded by someone with a trucking background who stumbled into the business, and it just took off. What I liked even more was that these guys weren’t big corporate types, and they were supportive of entrepreneurs. That’s how Dumpster Dudez came into my life.
Mike: Can you say a bit more about the unique aspects of your service model that you mentioned?
Rich: Sure! Our model is heavily focused on service. People can reach us anytime by phone or text, and we always respond promptly. We make the process very easy for our customers.
A key part of our uniqueness is that our dumpsters are perfectly sized for residential driveways. Most of our business comes from homeowners who are doing remodeling projects, cleanouts, or estate clearances, or contractors working on residential jobs like bathroom or kitchen remodels. The dumpster sizes we offer are well-suited for residential driveways.
Our trucks are dually, meaning six wheels instead of the larger 10- or 12-wheel semis that other companies use. This means less weight on the driveway and allows us to fit into narrower spaces, especially in areas like the North Shore, West Allis, and Wauwatosa. We can also place dumpsters off alleys where larger trucks can’t go.
It’s a neat niche, and it’s under-served since many smaller companies have been bought by larger ones. Plus, we’re under CDL (commercial driver’s license), so you don’t need a CDL to operate our trucks.
Another detail is that we put down boards under the dumpster’s wheels to protect the driveway, which homeowners really appreciate. We’re careful about where we place the dumpsters, ensuring minimal impact on the driveway. This all helps us serve residential customers in ways that other companies can’t.
Mike: I love that you’re embracing the idea that boring businesses make money. One thing we always tell people is that no matter what business you’re in, it should get boring. Constantly running around like a chicken with its head cut off is expensive in both time and money. The best businesses often thrive in the mundane.
Rich: Yeah, I dug deeper into that idea when I heard it, and it really clicked. A lot of people, especially those I worked with in the security industry, always ask me, “How did you go from security to dumpsters?”
Mike: The attractive part of business is making money. The rest of it is interesting, but the main purpose of a business is to support your life.
Rich: You know, as I was getting the Dumpster Dudez business going, I was bouncing ideas off my wife. She made an interesting comment: “All your experience has led you to this point, where you’re really ready to take on this challenge.” When you’re young, like in your 20s, you think you know everything, but you don’t. You need to go through highs and lows and face challenges before you’re truly ready.
Mike: That’s right. One of our sons is about to turn 30, and I remember 12 years ago, I seemed like the dumbest person on the planet to him. He wanted to know things right then, but as his challenges have grown and he’s become a parent, suddenly, we have something to offer again. It’s super interesting.
Rich: It’s true. I remember, when I was in my late 20s or early 30s, going to my dad and saying, “You were right about some things. Even though I didn’t listen at the time, I appreciate the guidance.” We had a good laugh about that.
Mike: What’s been your biggest learning so far as a business owner?
Rich: I’ve realized that business is all about solving problems. At Dumpster Dudez, we solve problems for our customers, whether it’s for a homeowner dealing with a remodel or a family going through a tough time, like after a fire or the death of a loved one. It can be very emotional, especially with projects like hoarder cleanups. I’ve always wanted to help people, and I think that’s a big part of my success.
But as a business owner, you’re solving problems constantly. The more I anticipate issues, the better I can manage them. For example, with our trucks, keeping them running is crucial, so we have to stay on top of maintenance. If a truck breaks down, we have a problem.
Last week, I had a hydraulic leak on a new truck, which was unexpected. I called a friend, and within an hour, I was back on the road. Anticipating problems and preparing for them, whether it’s maintenance or flat tires, has been key. You can’t avoid problems, but you can plan for them. Being able to quickly solve issues without panicking has been one of my biggest lessons.
Mike: It sounds like you’ve really embraced the concept of building a reliable team of people to help you handle those challenges. That’s been crucial for your business, right?
Rich: Absolutely. The support I’ve received from other small business owners has been incredible. I’ve had complete strangers offer help and referrals through social media, or even honk and wave when they see our truck, saying, “Hey, I saw you online! I have a referral for you.” It’s blown me away how much help people are willing to offer.
There’s a junk removal company I reached out to, called Junk It With J, run by a guy named Jason. When I started out, I didn’t know what to do. I just had a truck and a yard full of dumpsters. At first, Jason thought we were competitors, but I explained that if people asked me for junk removal, I could refer them to him. And he jumped in right away, offering help. He’s now a great friend, and we probably talk every day. We’ve helped each other out on jobs, and he’s made key introductions for me. In the beginning, referrals were everything. To go from zero sales to growing because of referrals from strangers was amazing. It continues to happen. We’ve developed informal groups for referrals, and the support has been invaluable.
Mike: What advice would you give to new business owners who are afraid of reaching out to people and growing their network? How do they get over that hurdle?
Rich: You just go. It’s not fancy, but you just go. For example, Jason from Junk It With J started his business a few years ago, and he’s always on the move. He doesn’t overthink it; he just goes. He’s been incredibly successful with a great business model. I’ve learned a lot from him. My advice is to just go. That’s what I did.
If I’m filling up with diesel and I see a contractor, I walk up, introduce myself, hand them a card, and ask if they rent roll-off dumpsters. When you have everything on the line in a business, all I knew was to just go. If I hit a wall, I didn’t care. I had to keep going to grow the business.
I was talking to my son the other day about how I have one shot at making this work, and I’m giving it everything I’ve got. Some people are hesitant to do this, but for me, it was out of necessity. I have a sales and business development background, so I’m used to it. The alternative—failure—is terrifying.
You’d be surprised how welcoming people are, especially when they realize you’re a local, family-owned business. People want to do business with you and help you succeed. It’s a phenomenon of its own.
Mike: If people really understood that business is about solving problems and that we’re simply talking to people about whether they have a problem, it would be easier to be brave.
Rich: Exactly. I’ve had people reach out to me months after we met at places like QuikTrip. They remember me and want to do business with me. It’s amazing. I just keep thinking, “I need to do more of this—it works.”
Mike: Consistency is key. It sounds like you’re doing this all the time. So, what’s next for you and your business in the next one to three years? What’s your top growth area or development challenge?
Rich: It’s about balancing buying more equipment and hiring more people. In the last six weeks, I’ve gone from being the only employee to having three employees. Our fourth starts on Wednesday. We’ve purchased a second truck, which we put into service recently, and we’ve ordered more dumpsters, which arrived a few weeks ago. We kept running out of dumpsters, so we bought more yesterday.
The challenge is timing these investments—both capital expenditure and resources. Our business has seasonality; December and January are slower than the rest of the year. But we’ve had models in place for years to help us know when to make investments in people and assets. We know how far in advance we need to order things. For instance, a custom truck can take 45 to 90 days, and dumpsters might take anywhere from four to eight weeks, depending on the season.
Sometimes, you have to make decisions before you’re fully comfortable, but you need to time them with growth. Over the last four months, we’ve seen anywhere from 21% to 43% growth per month. So, as we ramp up personnel and equipment, it’s interesting to see how that unfolds. The key is having the equipment and resources to meet the demand; otherwise, you’ll miss out on opportunities.
We’ve spent a lot of time planning before even purchasing this franchise, and I’m lucky to have a business partner who’s a financial expert. It’s like having an in-house CFO. His help has been invaluable in creating models to guide us. When we face challenges, we check the model and see if we’re on track.
For example, after we bought the last set of dumpsters and got them delivered, my partner said, “We’ll need more.” At first, I thought, “What are you talking about? We just got these.” Six weeks later, here we are buying more.
For the rest of this year, we’re focused on executing what we have and planning for next spring, when we’ll need another truck and three to four semi-loads of dumpsters.
Mike: Fast growth is exciting, but as you’re discovering, it’s also expensive. Paying attention to that balance is important, but it’s definitely an exciting place to be.
Rich: Oh, definitely. It’s much better than the alternative. It’s great to have business partners to bounce ideas off of, though, because you can’t just spend recklessly. The investments have to match the business’s growth. Overall, we’ve been well-received in the market. Our online business is doing exceptionally well and continues to grow. It’s another tech and marketing element that’s helped us. Who would’ve thought we’d be getting dumpster orders online? Now, we do more online sales in a month than we used to do!
Mike: The new generation of buyers doesn’t want to talk to anyone; they just want to go online and get what they need.
Rich: Exactly. It fits perfectly with the Dumpster Dudez brand, making it easy to do business with us. Some customers prefer to talk, so we make sure they can reach us by phone, email, or text. We always return calls and messages. We interact with customers through all kinds of platforms—social media, online, phone, text, email. It’s important to meet customers where they’re at and communicate the way they prefer.
Mike: That’s right. Well, Rich, I appreciate your time. If anyone needs dumpsters, they can get in touch with you anytime through dumpsterdudez.com, right?
Rich: Yes, that’s right. Dumpster Dudez, with a “Z” at the end. You can visit us at dumpsterdudez.com. We’re Dumpster Dudez of Greater Milwaukee. Coach Mike, I really enjoyed our conversation. Thanks for having me, and it’s been great to meet you.
Mike: Great to meet you too, Rich.