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Ryan Wheeler – From High School Dropout to Serial Entrepreneur



Ryan Wheeler - From High School Dropout to Serial Entrepreneur

Recently, I had the chance to sit down with Ryan Wheeler for an interview. Ryan is a serial entrepreneur with an amazing story of success. I asked him about his past, his future, and for his best tips for young entrepreneurs.

Hey Ryan, give a brief introduction of yourself?

I’m 34 years old, living in Hudson, Wisconsin. I own and operate a commercial construction company that I started almost 6 years ago. I have an amazing wife and 2 crazy kids.


Did you go to college?

I dropped out of high school in 11th grade, and never once had the urge to go to college. I was actually a very good kid in school, I just didn’t go very often. The school was boring to me, and I never saw it be necessary.


What motivated you to be an entrepreneur?

Honestly, when I dropped out of high school I had never even heard of an “entrepreneur”, the buzz words back then were “rapper” and “dope-man”. I went straight from dropping out into commercial roofing, which at that time I swore would only be a summer job until I got into a “real” career. Little did I know, 17 years later I’m still doing it. It wasn’t until about 11 years into union roofing and also operating crane that I decided I had to get out of the toxic environment that I was working in. Commercial roofing is littered with alcohol, drugs, gambling, and anything else that you can think of to negatively affect your life. But that was all I knew, that was my life. When I quit roofing (at $36/hour) I went and partnered with a neighbor in a landscaping company. I did this for almost 2 seasons and it was NOT for me. I had to get back to what I knew how to do better than almost anyone. That’s when the real hustle started and I went out on my own in the commercial roofing industry.


What does your average day look like?

I wake up around 5:30 am and help get my kids and wife off to school, daycare, and work. Then I make sure my job sites are setup and ready for the day with staff in place. This usually takes a while and often leads to me making a trip with anything needed to the job sites. I then catch up on any paperwork needed to get done and any emails needing responses.

My day isn’t littered with unnecessary tasks, I do what needs to be done. I’ve found many business owners are more worried about being busy then they are about being productive.


What are your 3 core principles?

  • Be a good human. Plain and simple, treat others the way YOU want to be treated.
  • Stay true to your word.
  • Stay humble.


What would you tell an aspiring entrepreneur in high school right now?

I’d tell them to stop listening to people who are telling them the decisions they need to make about college and future degrees. I would tell them to not take any advice from someone they aren’t willing to trade places with. I’d also tell them to quit watching Instagram stories! They can be very inspirational, but true success is hard as hell. Never settle, and DON’T STOP.


What are your future plans?

I plan to continue to grow my construction company but to step away from the day to day operations. I plan to focus on growing my personal brand and relationships and mentoring with children and adults. I’ll also be continuing to pursue my passion for exotic cars and using them as tools. Commercial real estate is where I will be investing next.

John Danes is a 19 Year Old Entrepreneur from Nashville, Tennessee. After being expelled from high school, John went on to start reselling rare sneakers and clothing. Not only did he see success in business, but he learned many lessons along the way. Now, he is the CEO of 99Media, which is a top digital marketing company in Nashville. He is also the host of The No Excuses Show, where he has interviewed millionaires and influencers all over the world.