Hi, I'm Gregg
I grew up in a small rural town in west central Illinois, living in an 800 square foot apartment beneath my family’s nursing home. It was a true mom and pop operation — my father handled the business and the trades, and my mother ran the care side as a nurse.
From an early age, I was absorbing both worlds: business conversations at the kitchen table, HVAC and plumbing lessons in the maintenance shop, and a work ethic shaped by helping keep the facility running. That upbringing taught me responsibility, grit, and the value of showing up.
The Journey
Chapters of a Life Driven by Purpose
CHAPTER ONE
Growing Up
The nursing home wasn't just a business; it was an education in humanity. I learned that every job matters, from the CEO to the janitor. The early mornings and late nights taught me that nothing is handed to you. It was a solid upbringing, one that valued practical skills over theory.
Chasing Golf Dreams
Like many kids raised in a family business, I wanted to see what else the world had to offer. I headed to college in North Carolina with dreams of college and playing professional golf. While I didn’t make the PGA Tour, I earned a degree in Business Administration with a concentration in golf management. Telling people that I have a degree in golf is a fun fact that always gets a smile.
CHAPTER TWO
Finding Trucking
After a setback with my first business venture after college, I found myself back home, regrouping and figuring out my next steps. That’s when trucking first entered my life. A friend of my father’s owned a small LTL company, and after two days riding with a driver and a quick driving test, I had my CDL. I didn’t drive full time then, but it planted a seed.
Building Businesses
I eventually moved to Savannah, Georgia, where I built a successful contracting company. It wasn’t glamorous work, but it met a real need, and the business grew quickly. Then in 2007, my father called: the nursing home was struggling. He asked me to come home to help. My six month plan has now turned into 18 years. We stabilized the business, strengthened operations, and ultimately sold the nursing home in 2015.
CHAPTER THREE
Leadership During COVID
With that chapter closed, I finally hit the road. I bought my first semi truck, got my authority, and began my driving career. Around the same time, I joined the board of our local hospital and started a serious relationship with a local girl. Then in 2021, life took another unexpected turn. At 45, I became a first time father — and the CEO of our community hospital during the depths of COVID. I didn’t even have a résumé. I intended to stay six months. I stayed nearly five years, helping stabilize the organization and build a strong team for the future.
Building a Lifestyle
When I stepped away, I didn't just return to trucking—I created a new way of life.
Today, Semi Retired Trucking combines meaningful work, travel, and freedom. I choose the loads I want, explore new places, spend more time with family, and even help rescue organizations transport pets to their forever homes.
This isn't just a business—it's a lifestyle built on balance, purpose, and the freedom to live life on my own terms. And I'm just getting started.
More Than a Trucking Business
Defining success through the positive impact we leave on the road and in the
communities we touch.
Travel
Exploring the hidden gems and vast landscapes of North America with a professional lens.
Meaningful Work
Delivering more than just goods—delivering reliability, expertise, and trust.
Rescue Animals
Leveraging our routes to help transport and support rescued animals to their forever homes.
Knowledge
Sharing wisdom from a lifetime of business and the unique perspective of the road.
The Journey Is Just
Beginning
Join me as I navigate the beauty of the open road and share the lessons learned along the way.