Long-time friend and employee, Jen Burton, reflects on Kris Oaks and his amazing journey as an entrepreneur

There is a lot you can say about Kris Oaks, but one of the best words I can use to describe him is fearless. I’ve known Kris for over 25 years now and never would have guessed we would all be on this journey together.  Kris and I met when he was fresh out of college. He joined my team as a management trainee. It was apparent from day one that Kris was smart and could easily progress through the company. It was also apparent that this job may have been a bit too formal and stuffy for him. The “corporate” world wasn’t something that was natural or comfortable for him. He took advantage of the things he could learn there and the connections he would make. Those connections have lasted and are stronger than ever to this day.

Kris has taught me and so many others through the years to take chances and use your words to ask questions and ask for what you want. He is an outstanding example of a guy that built his company from scratch, with his boots on the ground, buckled up, climbing on roofs, in dumpster trucks, and to this day he is still closing deals to get more work. Kris started this company from humble beginnings, working on roofs by himself. When he started his business, I hired him to replace a portion of my roof in Cheektowaga. I can still remember looking out the window and feeling bad that he was on my roof in the blazing sun. I’m sure he made very little money off that job, but he didn’t tell me no. He probably figured someday it would all work out in the end.

Kris grew up watching and helping his dad, Tom, with his siding company. His Dad told me how Kris has always been an active learner and eager to make money. He had his first job when he was 4 years old. Tom took him to his worksite and Kris was paid to be the “particle pick-up associate”. Kris had the task of making sure every bit of debris was cleared from the lawn and bushes, so they left the homes in pristine condition. Kris was an expert at this, and we know this because Tom inspected his work. It was in those early days that Kris developed a love for making money and learning things. When Tom realized Kris was money motivated, he taught him to count his money and suggested ways he could earn more. In his early teens, he went to a job with his dad on the lake and brought his fishing pole and planned to fish for the day. When he saw there was a cutter tool there, he said, “I think I can do that,” and that is when he started to actively work on the jobs with his dad. 

He went on to college to pursue a degree in business and graduated from the University of Buffalo in the early 2000’s. He continued to shadow his dad through college when his dad would take time off from his new county job, they would do a few side jobs when Kris was home from school. Right out of college, he took a full-time position for a large national company that continued to teach him to run a business, perfect the art of managing chaos, hire great people, pay attention to the bottom line, how to grow a business and take risks when it makes sense.

In 2003, Kris left that company to start his own business as a roofing contractor, which was the introduction of Kris Oaks Construction, Inc. Kris began closing jobs on his own and doing the work himself, he quickly grew the business enough to hire a crew and eventually office help. During his first few years, he realized that there was a hole in the roofing process for the dumpsters that were needed on his job sites. They were never readily available, or they weren’t placed or picked up as requested so he decided to buy his own. One thing about Kris is that when he thinks he can do it better than you, he will, and he will always be right! Kris purchased a used dumpster truck and a few containers and began servicing his job sites the way he wanted to be serviced. This is the beginning of Kris’ story of continuing to grow based on the demands that he encounters and in a way that will tie everything together.

A few years after his dumpster hobby was presented, he was approached by a few community members with an interest in finding business partners for their already established businesses and he bought into Woodeez Tree Service and Four Seasons Collision.

These businesses continued to operate independently, and Kris was mostly a silent partner then.

In 2017, early 2018, Kris found himself in an impromptu conversation with Charlie Graves, the owner of an established roofing and home improvement company in Rochester. This casual conversation turned into a conversation about Charlie and his interest in retiring soon and they unexpectedly came to an agreement for Kris to purchase Graves Brothers. This is when the expansion of the Oaks companies really started to take off. With that addition, he was able to inherit some great employees and a high-quality brand in the area. This means he needed the dumpster company to be more than a hobby and to run efficiently. Shortly after he hired me to operate the dumpster company as a standalone separate business which resulted in Oaks Dumpster Rental in 2018. From there several other opportunities presented themselves to Kris and he continued to find continuity in the new businesses to synergize with each other. From these opportunities, we welcomed the addition of KO Marketing (our internal marketing company) and Kitchens by Oaks (Formerly known as Kitchens by Countryside).

A few other colleagues in the industry decided to retire and their businesses fit nicely into the portfolio, so Oaks acquired Quality Homes, Abest Construction, Vekton, and 4 Points Remodeling.

There are several things that motivate and intrigue Kris, and real estate is certainly one of them.

Early on in his young adult days, he purchased a few properties which have now turned into a robust portfolio of properties that are used for short-term and long-term rentals.

We also had the addition of our “Entertainment division in 2019 with the purchase of the Senator’s Mansion in Churchville, now called Oaks Manor, and then Arrowhead Golf Course and eventually Twin Hills Golf Course.

In 2018, the total company was approximately twenty people, last count in June of 2023 we are well over two hundred employees.

Kris’s courage and vision have led the company to experience tremendous growth. The team that Kris has surrounded himself with is quite loyal and passionate about the growth and the mission.  We are having a ton of fun and love to celebrate our success together. Kris has always told us that he will have no problem finding us work, we just need to make sure we have the right employees available to do the work. We continue to hire talented individuals that believe in the future of our company. It has been such an exciting time for us all, I’m proud to be here for it and can’t wait to see what we do next.

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