Gary Cleveland doesn’t just like flying, he loves it. Cleveland is a Federal Aviation Administration (FAA) Certified Flight Instructor (CFI) for Helicopters and owns Cleveland Helicopter Services. Cleveland’s favorite part of flying? “Taking people up. It’s a blast! I’m doing all the flying and they are just having fun.”

Cleveland Helicopter Services is a Helicopter Flight Instruction School that offers flight training, check ride preparation, and a helicopter ferry service. Cleveland loves sharing his passion for helicopter aviation with people of all ages. “If I was a millionaire I would just fill every seat of my helicopter, of course it would be a seven seat helicopter then, and take anybody that ever wanted to go for a ride I’d just take them flying.”

His Story

Cleveland is the son of Gary Cleveland Sr. and Mary. He grew up on Cook Lake and graduated from Plymouth High School. He served in the Air Force for six years as a security policeman; then returned to his hometown and served as a law enforcement officer on the City of Plymouth Police Department. 

A scenic helicopter ride offered as an attraction during the Marshall County Blueberry Festival 2011 ignited a passion in Cleveland for aviation. Cleveland remembers that first ride. “It was with Kenny Keller at the Blueberry Festival. Then he taught me how to fly.”

Under Keller’s instruction, Cleveland went on to achieve his own private rating by 2012. He “picked away” at his commercial rating through personal ownership of two helicopters; and successfully achieved that certification in 2016.

Cleveland launched his instructing career in 2017 after he achieved certification as an FAA CFI. That same year Cleveland retired from his twenty-four (24) years of service on the Plymouth Police Department. 

Cleveland worked for Keller for two years at “Helicopter Online Ground School” which involved flight instruction. When Keller relocated his school to Warsaw, Cleveland opened his own business in 2019. Cleveland Helicopter Services will be celebrating two years on March 2, 2021.

A Different Kind of Flight School: Teaches and Reaches Coast to Coast

Though he can and does provide training for ratings from start to finish, Cleveland specializes in providing students who have already started their training at other larger schools with laser focus training to complete their Checkride Prep prior to testing with a designated FAA examiner. 

Cleveland said, “Being a helicopter instructor, my niche seems to be helping people who have started at other flight schools throughout the nation and they run into a road block of only getting in to their flight school maybe once per week if they are lucky. Big flight schools that are just extremely busy. When a person narrows down to that day, where they have to go see the FAA examiner for what we call a Checkride, they need the confidence of flying several times that week and getting a lot of ground school that week in between the flights. That’s usually where I come in; as a finish-up person for their rating.”

Though most flight schools prefer for students to use a helicopter provided by the institution to offset the cost of insurance, Cleveland can be flexible. “Most flight schools, if you buy your own helicopter, they shun you a little bit. Because they really need to pay for their helicopter insurance by getting people in their helicopter and keeping them flying. So, for the helicopters I have, there is no minimum hours they have to fly on them because they are leased from owners and the owners just get paid when they are flying.” 

Students from coast to coast seek training from Cleveland Helicopter Services. “They’ll fly here and stay at a hotel and we’ll work on finishing what they’ve picked away at for two, three, maybe ten years.”

Cleveland is also willing to travel to provide on-site, daily training for people who own their own helicopter. “I draw my business from a nationwide audience thanks to the internet that we have today. I’m not sure it would have worked twenty (20) years ago this way, because the way marketing worked it would be extremely hard to find people all over.”

Autorotation Aptitude Through Training and Real Time Emergency Experience 

Because of the unique way that Cleveland started out, he has superior autorotation aptitude through training and authentic emergency landings. “Some instructors may not have actually had real autorotations. It’s rare, especially if you start off with quality helicopters like we’re flying now.” 

Cleveland said, “In order to be a commercial pilot you need a lot of pilot-in-command (pic) hours. So you get your private rating at 40 hours if you are good and I got mine right at 40 hours. Then comes the question, how am I going to get 100 hours of pilot-in-command to get my commercial?”

Cleveland purchased a 1958 Hiller Helicopter to build time. He said he paid $74,000 for it in a world where paying less than $150,000 should ignite questions about why the craft is being sold so inexpensively. “It’s an aircraft that sold that should probably be in a museum but I used it to build time until one day it’s transmission exploded and I did what I was taught and landed in the field, no damage. But, I couldn’t afford the repairs to the transmission and it was also going to need an engine rebuild because that same oil that goes through that transmission goes through the engine. So I sold it at at a loss.” 

He persisted and purchased a RotorWay Helicopter for $40,000. “I had several times where that actually caused me to make an emergency landing with no power.” Cleveland laughed, “There again, it’s like the moped of helicopters, but because of it I got my hours.”  

Since Cleveland has owned both a Hiller and a RotorWay, he gets calls from clients who want training. “So I keep on flying in these substandard machines and I’ve had seven (7) real autorotations. One was to a city street in Atlantic Beach, Florida. No damage.” He laughed, “So I have become the ‘go-to-guy’ for autorotations.” 

The ability to handle emergencies is critical for pilots. “I experienced some real emergencies. I know, not only from my law enforcement time, but from flying that I can handle emergencies. Because some people, you may never know - what are they going to do when the emergency happens? Will they panic or do what they are told?”

COVID-19 Precautions: Aviation is Essential

Despite the extra work to offer a safe ride and training during the pandemic, Cleveland Helicopter Services takes all necessary precautions to protect guests and students to prevent the spread of the virus that causes COVID-19. “We do our best to prevent the spread.” 

Cleveland is assisted by two flight instructor partners; Jessica Meiris and Matt Goodrich. “They are both from Colorado. I helped train them both. They needed their start.” Cleveland said it is challenging for newly certified flight instructors to find work in the field.

Discovery Flights

Discovery Flights are recommended for anyone who is interested in the program; those start at $300 an hour for the two-seated helicopter. A larger aircraft would cost $450 to $550 an hour depending on the weight of the student. 

Cleveland said that $300 might sound costly, but industry average starts at $330 and increases from there. People who wanted to share the cost of a Discovery Flight with another party to split the cost might find a flight to be a refreshing getaway from the cares and concerns on land. 

Cleveland said that obtaining a helicopter license is costly. For those who have a strong, natural aptitude for helicopter aviation and catch on quick, it will cost them $15,000 for the private rating. “Whereas they can probably get the airplane rating with $6,000. It just costs so much more to fly a helicopter. The initial cost is more, the hourly rate is more, and the insurance is outrageous making it an expensive thing to do.”

Ferry Service 

Cleveland also provides helicopter ferry services to clients. His longest delivery was an R22 for an attorney in Texas from Puerto Rico to Texas. “It would make it about three (3) hours on a tank of fuel. So I had to go from Puerto Rico to Dominican. Then Dominican to Turks and Caicos. Turks and Caicos to two stops in the Bahamas. Then checked in at Fort Lauderdale. Then another two days getting from south Florida over to Texas. That was the longest.” 

The highest altitude ferry Cleveland flew was two helicopters that he picked up on the West Coast and had to fly them over the Rocky Mountains “The Rockies” to deliver them to the Midwest. “It’s been exciting.” 

Leisure Tours, Special Events & Aerial Photography

In addition to flight training, Cleveland Helicopter Services can be commissioned for leisure tours, helicopter rides, special events including festivals and birthday parties, and aerial photography. 

Contact Information

Cleveland Helicopter Service operates out of the Plymouth Municipal Airport located at 301 Airport Road, Plymouth. 

Facebook @ Cleveland Helicopter Services

Call 574-910-0920

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