Kevin Halbert’s Path to Business Ownership 

EFBC MEMBER SPOTLIGHT

Kevin Halbert built his career in strategy and management consulting, helping large enterprises tackle complex challenges. But he wanted something more—an opportunity to take ownership of decisions and see their impact firsthand. That opportunity came with Winkler Tree, where he transitioned from advising businesses to leading one.  

We are proud to have Kevin as a member of the Entrepreneur and Family Business Council. We reached out to him to gain insights into his path to business ownership, learning how he has navigated the challenges of entrepreneurship while embracing the impact his business has on the urban landscape.

From Consultant to Business Owner 

Kevin spent years solving complex business problems across industries, particularly in mining and chemical production. While he valued the intellectual challenge of consulting, he wanted to take on a role where he could see the long-term impact of his decisions. 

“I enjoyed tackling new problems with new clients, but was often frustrated by the lack of long-term ownership over the results of our work. We would typically make a recommendation, launch the initiative, and then move on to another client or issue,” Kevin shared. “I wanted the chance to be the principal decision maker who would have to live with the pros and cons of my own decisions and actions. Owning and operating my own business has certainly been that!” 

Overcoming the Learning Curve 

Stepping into the tree care industry as an outsider wasn’t easy. Earning trust—from both employees and industry peers—took time, effort, and patience. 

“I understandably faced a lot of skepticism from both employees and industry peers,” Kevin admitted. “The only way to resolve that was through time and effort, but it certainly wasn’t easy to build the experience and trust right out of the gate. I’m grateful to a lot of exceptional teammates and industry peers for giving me a chance to learn and earn their trust.” 

Beyond relationships, the operational side of running a small business also came with challenges. 

“I had a broad background in finance and operations, but had never worked in a small business where people and process issues are just different from those in large enterprises,” he explained. Over time, he built the experience and network needed to make more confident decisions. “You develop a network of ‘go-to’ people for different issues, which makes it a lot easier and faster to make better decisions.” 

Growing a Legacy 

For Kevin, tree care is more than just a business—it’s about making a lasting impact on the environment and the community. The trees Winkler cares for today will shape the urban landscape for generations to come. 

“We’re a team of tree lovers, and the trees themselves are the legacy we hope to leave behind. We’re proud to play our small part in creating and maintaining a healthy urban forest, populated by people who appreciate it,” he said. 

Not everyone sees tree care as a priority—some see it as a task to check off a list. But for those who recognize the beauty and importance of trees, Kevin’s team is eager to help. 

“I think most people subconsciously get a lot of positive benefits from trees, even if they don’t notice or think about them very often. Next time you’re outside, take a moment just to notice the volume of trees in our region. Try to imagine your neighborhood if all of the trees were gone. Their absence would be striking, and they’d be greatly missed.” 

Proud to Have Kevin in Our Community 

At EFBC, we are proud to have Kevin as part of our community of business leaders. His dedication to learning, adapting, and making a meaningful impact—both in his business and in the environment—exemplifies the drive, resilience, and leadership that define great entrepreneurs. We look forward to supporting his continued growth and celebrating the lasting contributions he and Winkler Tree Service are making to our local landscape.

Read Kevin’s full interview:  

Q: What drew you to transition from your previous career to business ownership? 

I spent the previous 10 years as a strategy and management consultant for large enterprises, working across a broad range of industries, though primarily focused on mining and chemical production. I enjoyed tackling new problems with new clients, but I was often frustrated by the lack of long-term ownership over the results of our work. 

We would typically make a recommendation, launch the initiative, and then move on to another client or issue. The role was primarily focused on influencing decision-makers, but I wanted the chance to be the principal decision-maker—someone who had to live with both the pros and cons of my own decisions and actions. Owning and operating my own business has certainly been that! 

 Q: What were some of the challenges you faced during the transition? 

The list is long! As an outsider entering the tree care industry for the first time, I understandably faced a lot of skepticism from both employees and industry peers. The only way to resolve that was through time and effort, but it certainly wasn’t easy to build the experience and trust right out of the gate. I’m grateful to a lot of exceptional teammates and industry peers for giving me a chance to learn and earn their trust. 

 Another big challenge was simply how long it took to solve problems I had never faced before. I had a broad background in finance and operations, but I had never worked in a small business where people and process issues are just different from those in large enterprises. 

Over time, you start to build some pattern recognition, and you also develop a network of “go-to” people for different issues. That has made it a lot easier—and faster—to make better decisions. 

Q: What legacy do you hope to leave as the owner of Winkler Tree? 

We’re a team of tree lovers, and the trees themselves are the legacy we hope to leave behind. We’re proud to play our small part in creating and maintaining a healthy urban forest, surrounded by people who appreciate it. 

 Some people, of course, view tree care as a necessary burden they have to deal with, and we’re happy to help them through that. But it’s especially rewarding to work with clients who truly appreciate trees and care about maintaining them for the broader community and future generations. 

 I think most people subconsciously benefit from trees, even if they don’t often stop to notice them. Next time you’re outside, take a moment just to observe the volume of trees in our region. Now, try to imagine your neighborhood if all of the trees were gone. Their absence would be striking, and they’d be greatly missed.