Our Roots Run Deeper Than Our Name.
A family history rooted in craftsmanship, dedication, and the lessons that continue to shape a new generation.
The Work Came First. The Lessons Stayed.
From the grounds and landscapes of the Twin Cities to a new owner-operated business, this is the history behind the Olson Outdoor Services name.
More Than Just an About Us Page
Most businesses have a story. Ours begins long before Olson Outdoor Services LLC was established.
You'll notice this page is a little longer than the typical About Us page, and that's intentional.
This isn't simply an introduction to a company. It's also a dedication to the people whose hard work, guidance, encouragement, and belief in me helped make Olson Outdoor Services possible.
It's a story about my parents, the different paths they traveled, and the lessons they passed down. It's about family, friendships, personal growth, and the people who stood beside me while I worked toward building something of my own.
Every chapter connects back to OOS in some way. From the craftsmanship and attention to detail I learned growing up, to the importance of treating people with respect, keeping your word, and taking pride in what you do.
Olson Outdoor Services LLC is a new business, but the values behind it have been a lifetime in the making.
So if you have a few minutes, I invite you to read beyond the services we offer and get to know the people, experiences, and principles behind the name.
Because to me, Olson Outdoor Services is more than a business. It's an opportunity to put a lifetime of lessons into practice and build something worth being proud of.
Where It All Began
The story behind Olson Outdoor Services begins long before the company itself.
Its roots reach back to the early 1970s, when Lyle Olson was building a career in grounds maintenance and working with property management companies around the Twin Cities.
Among his early positions was serving as Grounds Maintenance Supervisor at the Colony of Richfield.
During those years, landscaping became much more than an occupation. Lyle developed a genuine interest in the landscape itself: how plants grew, what different varieties needed, and the skill required to care for them properly.
In 1974, he enrolled at Anoka Technical College to pursue further education in horticulture.
He completed its two-year landscaping program, earning his diploma and combining his formal education with the experience he had already acquired on the job.
With growing expertise, a determined work ethic, and the desire to be independent, Lyle began building a business of his own.
An Old Pickup Truck and a Few Shovels
Lyle Olson Landscapes began modestly, with determination and the willingness to work hard.
With an aging pickup truck, a few shovels, and an eagerness to find work, Lyle began establishing his company one job at a time.
The early work was varied, including general landscaping, grounds maintenance, and even repairs to parking lot asphalt.
As the business developed, he increasingly concentrated on landscape design, plant maintenance, and the skilled work of trimming and shaping shrubs.
In 1989, Lyle broadened his horticultural knowledge further by earning his Master Gardener certification through the University of Minnesota.
His detailed and meticulous approach to trimming shrubs became one of the qualities for which customers remembered him.
He knew that shrubs were not all the same. Each variety needed its own consideration, and proper shaping required knowledge of the plant's natural growth and characteristics.
Lyle believed good landscape maintenance was about far more than having the right equipment or putting in the hours. It required patience, an educated eye, and genuine attention to detail.
Those beliefs shaped the way he worked and the reputation he earned.
Property management companies and homeowners associations returned to him because they recognized the craftsmanship and care he brought to their grounds.
For Lyle, workmanship and reputation were inseparable. Each completed property was a reflection of his standards and his name.
The Woman Working Beside Him
But the story of Lyle Olson Landscapes wouldn't be complete without recognizing the contributions of my mother, Debra Jones.
My mother spent many years working right alongside my father. She wasn't simply helping from behind the scenes. She was doing the same demanding, hands-on work that came with building and maintaining landscapes.
She shoveled rock, laid sod, planted shrubs, and handled cleanup while my father worked on the detailed trimming he was known for.
And she contributed something else that complemented his talents.
My father could envision how he wanted a landscape to look, but putting those ideas onto paper wasn't his strongest skill. My mother could draw and paint, and she used that artistic ability to illustrate the landscape designs he envisioned.
In that way, she helped take the ideas in his mind and make them visible to others.
They brought different abilities to the work, and both contributed to the business in ways that mattered.
Those years of working together became part of the family history that would eventually influence my own approach to Olson Outdoor Services.
Pride in workmanship is the best boss you will ever have.
Three Sons and a Family Education
Lyle Olson Landscapes was an independently owned business, but its influence went far beyond the properties it maintained.
It was also where Lyle's three sons first learned about landscaping, working hard, and taking responsibility for a job.
Their earliest experiences weren't always exciting. Sometimes they involved waking up much earlier than they wanted to, getting into the work truck, and spending the day accompanying their father to properties around the Twin Cities.
For one of the boys, the bicycle his father brought along in the truck was an especially important part of those days.
While the crew worked, there were neighborhood friends to meet and little adventures to discover.
Occasionally, his father would hand him five dollars and send him off on his bicycle to a nearby gas station to buy cold drinks for everyone.
Lyle even came up with a rather memorable way of paying his young helper.
He offered two dollars a day: one dollar for helping with the work and another dollar for staying out of his hair.
That arrangement worked out quite nicely for a young boy.
After saving fourteen dollars, he was finally able to buy a remote-controlled car from a thrift store during a stop on the way home.
Those ordinary days would become some of the most memorable parts of growing up around his father's business.
As the boys grew older, their involvement in the actual work became more substantial.
Lyle's teaching style balanced patience with old-fashioned firmness. His sons were expected to pay attention, recognize different shrubs, and understand the reasons behind the care each plant required.
He was especially particular about doing the work correctly.
He wanted his sons to understand that every job carried his name, and that his reputation depended on the work they performed.
It was an education in the trade, but also in accountability and personal character.
Looking back, I realize those days were about more than learning a trade. They helped form an appreciation for the care and effort that goes into doing a job well — something both of my parents demonstrated throughout my childhood.
The Lessons of Two Parents
My father's landscaping career is an important part of my story. But to understand the person I became, you also have to know about my mother, Debra Jones.
My mother was a hardworking woman with many different talents.
She could work alongside my father shoveling rock and planting shrubs. She could turn his landscape ideas into drawings. She could create beautiful quilts with remarkable attention to detail.
And she would eventually introduce me to a completely different world — the world of professional trucking.
Debra Jones
My mother taught me something that has remained important throughout my life.
Love isn't just a word. It's something we demonstrate through our actions.
Her example showed me that caring for people is about being there for them, putting in the effort, and demonstrating that love through what we do.
The Artist Behind the Designs
My mother had a creative ability that complemented my father's knowledge of landscaping.
He understood plants, their needs, and how to envision a finished landscape. She had the artistic skill to draw those ideas onto paper.
She didn't spend much of her personal time drawing or painting, but she used those abilities to help my father's business.
Her own favorite form of creativity was something different.
She loved quilting.
My mother made some of the most beautiful quilts. I remember falling asleep on so many nights as a child to the familiar sound of her sewing machine.
At the time, it was simply one of the sounds of home. Today, it's one of the memories of her that has stayed with me.
There's one quilt in particular that I still have.
It's a floral design made up of individual square sections. Inside each square are flower-shaped pieces of fabric, carefully stitched together with precision.
It has cream-colored buttons, with little heart-shaped buttons layered over round ones, and a deep forest-green backing.
I don't remember whether she made it specifically for me or whether it simply became mine over time. What I do know is that it became my favorite.
It's worn and torn now from years of use, and I've carefully packed it away in hopes of someday having it repaired.
To me, that quilt is more than fabric and thread.
It's a piece of my mother's love and craftsmanship that I want to preserve.
I see a connection between the precision my mother put into her quilting and the attention my father gave to the shrubs and landscapes he maintained.
They practiced different crafts, but both taught me that details matter.
And today, that shared appreciation for quality workmanship is part of what I want Olson Outdoor Services to stand for.
Those Cold Minnesota Mornings
While my mother spent years helping my father with landscaping, her primary job during much of my childhood was driving a school bus.
She drove for the bus company that serviced the school I attended.
Some of my earliest memories of her working involve getting up in the wee hours of the morning on bitterly cold Minnesota days so I could ride along with her.
I would climb onto the bus and ride the entire morning route, from the very first pickup until she eventually dropped me off at school.
Looking back, those mornings were another example of how much of my childhood was spent accompanying my parents while they worked.
With my father, I spent days traveling between landscaping properties. With my mother, I spent early mornings riding her school bus.
And before long, her driving career would take us much farther than the neighborhoods around my school.
A Childhood Spent on the Road
When I was about fifteen or sixteen, my mother's driving career took another direction.
She became a semi-truck driver, traveling across the country, and I began accompanying her on some of those trips.
Sometimes I would spend weeks out on the road with her. We traveled from one corner of the country to another, even making trips into Canada.
Some of my most vivid memories aren't necessarily of the places we visited, but of the sights, sounds, and smells that came with life on the road.
The unmistakable smell of diesel in the morning.
The quiet, steady rumble of semi-trucks idling through the night in truck-stop parking lots.
Sleeping in the top bunk of my mother's semi, surrounded by those familiar sounds.
Those experiences became a part of me.
What began as riding along with my mom eventually became an interest in trucking that stayed with me as I grew older.
In 2013, I attended commercial driving school and obtained my CDL, beginning a professional driving career inspired by the years I spent alongside her.
And today, I still drive a semi-truck professionally.
Every time I think about how that career began, I come back to those mornings on her school bus and the weeks I spent traveling the country with her.
Just as my father introduced me to the world of landscaping, my mother introduced me to the world of trucking.
Neither path was simply something I learned about from a distance.
I grew up experiencing both of them beside the people who inspired me most.
Lessons That Stayed
My mother and father both instilled in me the importance of craftsmanship, attention to detail, and taking pride in good work.
From my father, I learned about landscaping, horticulture, responsibility, and the value of establishing a reputation through the work you do.
From my mother, I learned through her hard work, her creativity, her love, and the determination she brought to the different paths she pursued.
But neither parent taught those values alone.
Both showed me the importance of making an effort, paying attention to the details, and doing something well.
They helped shape the person who would one day establish Olson Outdoor Services LLC.
My father retired from his landscaping business around 2010, ending a professional career shaped by decades of dedication to his trade.
He passed away in 2019.
The lessons he taught, along with the lessons my mother passed down through her own work and example, are still part of my life today.
A New Chapter — Olson Outdoor Services LLC
Growing up around my father's landscaping business gave me years of hands-on experience and knowledge that I didn't fully appreciate until much later in life.
But the lessons that stayed with me went beyond knowing how to maintain a landscape.
I remembered the relationships my father developed with property managers and homeowners associations.
His customers knew who he was. They trusted his experience, appreciated his judgment, and understood the effort he put into their properties.
Over time, I came to value those relationships and the workmanship that supported them.
I also came to recognize how special my father's knowledge was.
He understood different plants, their individual needs, and the importance of doing quality work instead of simply finishing a task.
Those were skills I wanted to carry forward, and I began imagining how I could build something meaningful myself.
That realization helped inspire the creation of Olson Outdoor Services LLC.
The road to this point hasn't always been easy or straightforward.
Life has brought difficult experiences, unexpected changes, and periods when I wasn't sure where I was headed.
But along the way, I began to understand that the values my parents taught me had remained with me.
They were still there.
My father's insistence on quality work and the importance of protecting your name and reputation.
My mother's example of showing genuine love through actions, her creativity and determination, and the dedication she brought to her work.
And both parents' attention to detail, willingness to work hard, and pride in what they created.
I may have needed time to recognize the depth of those lessons, but they are now an important part of the life and business I'm building.
Following Two Paths
Today, there's something particularly meaningful about the direction my life has taken.
I drive a semi-truck professionally, following the career path my mother introduced me to years ago.
And I own and operate Olson Outdoor Services LLC, working in the trade my father first introduced me to as a child.
In many ways, I have followed two different paths that helped shape my childhood.
Sometimes I find myself feeling pulled between those two worlds.
When I'm driving truck, I think about my mother's influence. When I'm working on OOS, I think about the business my father built and the knowledge he passed down.
But I've come to recognize that their influences aren't limited to the type of work I'm doing on any particular day.
Both are part of who I am, and both have helped shape the standards I want to carry into my own business.
I hold onto a personal hope that someday those two paths might come together in an even more meaningful way.
For now, I'm proud to keep building something of my own while carrying forward the lessons both parents taught me.
What OOS Means to Me
Olson Outdoor Services is not a business I inherited, nor is it a continuation of Lyle Olson Landscapes.
It is a new and independently owned company influenced by the experiences, principles, and family history that preceded it.
I want to develop lasting professional relationships with the people who trust me with their properties.
Whether I'm working with a property manager, an HOA, or an individual homeowner, I want my customers to know who they're dealing with.
I want them to feel comfortable reaching out with questions and to know that their concerns matter to me.
My father's belief in craftsmanship influences the way I approach property maintenance.
My mother's hard work, creativity, and example of showing care through actions remind me that the way we treat people matters just as much.
And the attention to detail I learned from both of them is something I want reflected in the work OOS performs.
I don't measure success simply by the number of properties under contract.
I measure it through the trust, professional relationships, and reputation I build over time.
To me, that's how Olson Outdoor Services becomes more than just another property maintenance company.
The People Who Stood Beside Me
A special acknowledgment to the family, friends, and loved ones who have helped make this new chapter possible.
While Olson Outdoor Services carries my family name, the journey of building this business has never been mine alone.
I want to take a moment to recognize some of the people who have believed in me, encouraged me, and stood beside me throughout my journey.
To my brother, Darin Olson, thank you for your continued support and encouragement. Family means a great deal to me, and knowing I have your support is something I genuinely appreciate.
To my good friends Brad S., Mark W., Chandler H., Miles J., and Brenda E. , I want to personally thank each of you. Your friendship, encouragement, and support have meant more to me than you may realize.
And to my other close friends who have stood beside me along the way, please know that your support hasn't gone unnoticed.
To My Son, Daena
And to my son, Daena, if there's one thing I hope you learn from watching my journey, it's that where you find yourself in life doesn't have to determine where you end up.
Life isn't always going to be easy. You're going to face challenges, make mistakes, and experience moments that test everything you've got.
But no matter how far life knocks you down, you can always find the strength to get back up, dust yourself off, and build something better.
I hope that as you watch me work toward building Olson Outdoor Services, you'll understand that success isn't about never falling. It's about refusing to let your lowest moments define the rest of your life.
And if my journey teaches you even a little of that, then I'll have accomplished something far more meaningful than simply building a business.
To Samantha
And to my girlfriend, Samantha, I want to give a particularly heartfelt thank-you.
For the past two years, you've continued to encourage me, challenge me, and push me to become a better person every single day.
You've believed in my potential and encouraged me to keep moving forward, even when the road hasn't always been easy.
Your support has played an important part in the person I'm working to become, and I am deeply grateful to have you beside me.
Starting Olson Outdoor Services is about more than building a business. It's about personal growth, purpose, and creating something that I can genuinely be proud of.
The Roots That Remain
Sometimes the influence of people we love feels especially close, even when they can no longer stand beside us.
For me, a monarch butterfly is a meaningful reminder of my father.
Seeing one brings back memories of him, the years we spent together, and everything he tried to teach me.
A dragonfly carries similar meaning when I think of my mother.
It reminds me of her strength, her love, and the comfort she has given me.
I also carry very different, everyday memories of both my parents.
My father carefully shaping shrubs, explaining the difference between plants, and reminding his sons to take pride in their work.
My mother at her sewing machine, creating quilts one careful stitch at a time.
The cold mornings riding her school bus and the distant rumble of diesel engines as I slept in the top bunk of her semi.
Those memories may seem ordinary to someone else. To me, they are reminders of the experiences that made me who I am.
I sometimes think about how my father would feel seeing the company I'm building today.
I hope that he would recognize his influence in the way I work, even if my journey here was far from a straight path.
And when I think of my mother, I recognize how much of her influence continues through my own working life.
My parents each taught me valuable lessons, and together they gave me a foundation that reaches far beyond either profession.
I'm not trying to recreate my father's landscaping business or claim that I do everything perfectly.
Instead, I'm trying to put the values both of my parents taught me into practice in my own life.
My father started with an old pickup truck and a few shovels, believing that honest work and craftsmanship could establish a respected name.
My mother showed me that determination, creativity, and care could take many forms, whether through physical work, something carefully made by hand, or a career spent traveling the road.
Today, I carry pieces of both those stories into my own.
And while I don't know exactly where the future will lead, I hold onto a hope that the paths they helped me discover may someday come together in an even more meaningful way.
Until then, every property I maintain, every professional relationship I build, and every opportunity to do something well is another chance to honor what they taught me.
That's the foundation I'm building Olson Outdoor Services LLC upon.
The Olson name is on the work I do today. But behind that name are the lessons, love, and craftsmanship of both my parents.
And I intend to honor them.
Let's Talk About Your Property.
Whether you manage a homeowners association, commercial property, or your own home, Olson Outdoor Services welcomes the opportunity to discuss your outdoor maintenance needs.
Request an estimate online or contact OOS directly by phone, text, or email.