On a Roll: A Q&A With Chris Graen of Hassle Free Roll-Offs

When it comes to tackling a big project — whether it’s a home renovation, a spring cleanout or a construction job — keeping discarded or waste material under control can quickly become overwhelming. That’s where Chris Graen, owner of Hassle Free Roll-Offs comes in, offering a convenient and efficient solution for getting rid of large amounts of debris. His company’s portable containers are designed to be easily delivered and picked up, making them ideal for homeowners, contractors and businesses needing a quick and effective waste removal solution.

In this exclusive Q&A session, we sit down with Chris to learn about the ins and outs of running a local roll-off dumpster company and what it takes to keep things rolling.

Q: Who, or what, led you to start your own business?

Chris: I wanted to own a small business for quite some time. I was at my last job for 10 years working for a stone manufacturing company, which was a great experience. But, when my wife and I moved to the Iowa Great Lakes area, I decided it was time to try something new. I researched business ideas online and used my previous experience to form Hassle Free Roll-Offs in early 2023. We provide waste management services, including roll-off services for new construction sites, commercial/residential remodels and demolitions, house clean-outs and general trash.

I started with three dumpsters and grew it to 36 in the past year, so business is booming. I am constantly purchasing additional dumpsters to meet the need in the area, between the influx of construction projects and a growing customer base.

Q. What are a few key factors that have contributed to your company's success?

Chris: A lot of dedication, hard work and networking have contributed to my business’s success. In the beginning I was showing up on job sites and doing a lot of cold-calling to market my business. I received a lot of “nos,” but eventually many of those “nos” turned to “yeses.” That’s very rewarding. 

And I focus heavily on customer service. I try to make sure my customers are satisfied with the service. And if they aren’t, I try to do everything I can to make it right. 

Q. What is the most rewarding part of business ownership?

Chris: It’s being able to say I started something from scratch and have succeeded. I’m proud to see the growth that has happened and I’m looking forward to continuing to build my business. I’d like to get to 50–60 dumpsters, a full-time employee and owning another truck or two.

Q. What is the biggest challenge you've faced, and how did you overcome it?

Chris: One of the biggest challenges I faced was when our area was hit with a major flood. I tried to do as much as I could to give customers and the community access to dumpsters to help with clean-up efforts. For two months, I worked until midnight helping get dumpsters to those who needed them.

Q. Why did you decide to partner with Northwest Bank?

Chris: My father had a relationship with Northwest Bank for years and knew Nicole Evans. He got me in touch with her when I first had the idea to start my roll-off dumpster business. She’s been very important to my success. Nicole is one of the first people I call when I have questions about how to expand my business or need financial advice. For instance, I gave her a call on a Saturday after the flood hit. I wanted to get more dumpsters to help my customers and the community. I don’t know many bankers who would answer their phones on a weekend, so that shows she goes above and beyond for me and my business.

Q. Who are the mentors that have encouraged you along the way?

Chris: My wife, mom and dad have supported my business journey and played a big part. I also look to the local businesses and contractors for advice. We’re a close-knit community and they’re always willing to answer my questions. I also learned a lot from my previous employer at the stone company, where I was able to work on a variety of jobs from budgeting to project manager. 

Q. How do you achieve work-life balance?

Chris: I’m still working on a work-life balance. My business has grown a lot this year, which is great, but it does mean a lot of working hours. There are days I’m up at 4:30 a.m. and I don’t get home until 7 p.m.

I also work as a volunteer firefighter. Another interest of mine is snow removal. I clear snow for about 30 customers during the winter.

My wife and I recently welcomed our first child, so I’ve been making sure I have sustainable working hours to be home with my family. My goal for next year is to hire an employee full-time to help me offload some of the work.

Q. What advice do you have for aspiring entrepreneurs looking to start their own business?

Chris: Make sure to have an idea of a business plan in place before starting your company. I jotted mine down on an Excel spreadsheet and then I met with Northwest Bank to talk through it with them. They helped me expand on my plan, including adding in my financial projections and goals. Now that I have a solid plan in place, I’m constantly looking at it to see what goals I can hit next. 

Connect with Northwest Bank

If you’re looking to start a small business like Chris did, it’s important to have the right partners in place. By teaming up with a community bank, like Northwest Bank, you gain access to personalized financial support, valuable advice and local connections that can help your business thrive. Whether you're securing a loan for equipment, managing cash flow or navigating the ups and downs of entrepreneurship, a strong partnership with a community bank gives you the stability and confidence to grow your business. Reach out to our commercial bankers today.