We’re excited to introduce you to the always interesting and insightful Kenny Sutherland. We hope you’ll enjoy our conversation with Kenny below.
Kenny , looking forward to hearing all of your stories today. We’d love for you to start by sharing your thoughts about the pros and cons of family businesses.
Family businesses can be a mixed bag. It can bind you in ways that a lot of other activities can’t. Overcoming hurdles on projects in real time teaches you a lot about real world problem solving. Seeing how your parents handle a job that went sideways or how they still treat an irrational customer with respect teaches integrity, honor, and grit in a way that just talking about can’t convey.
There are also pitfalls, disagreements can certainly turn into hurt feelings and shouting matches. You can feel trapped by the responsibility to the family that you otherwise wouldn’t feel at a “normal job”. Sometimes it can feel like the only thing you talk about is work. That can be exciting if things are going well and you get to dream together about where the business is going. It can also feel overwhelming if things aren’t going so well. The important thing is to communicate how you’re feeling before it becomes a wedge in your relationships.
I do hope to pass our business down to our children. I already see talents they are developing that I think would flourish in this kind of environment. But we’ll have to see when they are older if they have an interest. I certainly won’t force it on them.
My only advice based on my experiences, is have grace, remember they are still family, not just employees. Have an agreed upon exit strategy up front in case things don’t go as expected. Never do a straight 50/50 partnership. There needs to be a clear leader or a third person to provide a tie breaker. Be ready to forgive and make sure you still spend time together away from work.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
My name is Kenneth Sutherland, I am a second generation business owner of Highway Man Signs. My parents started the company in a box truck doing decals and small signs for events such as rodeos and flea markets. One day Dad put HighwayMan on the side of the truck. After a short time we decided to start a brick and mortar store and pulled the cutter and computer out of the truck and into an office. I suggested we call it Highway Man Signs and designed our first sign for the building.
Funny enough I had been drawing and designing race cars since I was 10 in a paint shop program in a popular nascar racing game series and those skills prepared me to design auto wraps and signage in my current career.
At Highway Man, we print and manufacture signage for all types of businesses, organizations, churches and schools. If you need a sign we can provide it! We started small with banners and yard signs, but are now a full service sign company providing commercial signage such as lighted pole signs, channel letters, and full custom auto wraps. We just built a replica Las Vegas sign for our main office in Bartlesville.
We specialize in helping small businesses take their businesses to the next level by providing them with professional logo design and signage that sets them apart from the crowd. It is our goal to literally make their vision come to life and help them feel confident. When you look good, you feel good and that feeling can help our customers use that confidence to sell more and be more successful than having substandard graphics and signage.
The thing I am most proud of is the satisfaction I get from seeing an entrepreneurs face when they see their logo or sign or wrap and they are realizing their dream for the first time in real life.

Can you share a story from your journey that illustrates your resilience?
Not a specific story per se, but there are so many things that can kill a business. There are seasons where things can’t be any better. But there are seasons where just deciding not to quit is a win. Employees will come and go. Jobs may not go how you would like. Treat every “loss” as a learning opportunity. How can I grow through this? what can I learn from this? Don’t make the same mistakes over and over. Get help. Hire a business coach or find a mentor who has been through it and are on the other side.

Can you tell us about what’s worked well for you in terms of growing your clientele?
3 things have helped us continuously grow year over year.
1. Integrity. This is the foundation. Without it you will not be successful. Admitting when you are wrong. Take responsibility when a deadline is missed. Keep your promises. Under promise and over deliver. This is the cornerstone of good business practices. Your customers will tell others how you treated them especially when something doesn’t go as expected.
2. Great physical marketing. Of course we are a sign company but you will not grow without good signage. Auto wraps are a great investment for any business. And if you have a store, don’t skimp on the signage. It will set the tone for what to expect from you.
3. Google. Face it we live in the Information Age. Most people will google what they are looking for first. And they generally call whoever has the highest number of good reviews. This is the “new” word of mouth. Get over yourself and ask for reviews. Find out who has the most reviews in your area and make it a goal to get more than they have. But you have to do a good job! This goes back to integrity, if you’re not doing a good job this step will not help you. Also if you have website, invest in SEO. Hire someone to write articles and build out your website so it ranks hire and people can find you! If they can’t find you, you’re doing yourself and your business a disservice.
Contact Info:
- Website: https://Highwaymansigns.com
- Facebook: /highwaymansigns
- Youtube: @highwaymansigns5177





