Rick Hamilton: Parallel Careers in Aviation & Tech

Rick Hamilton's passion for aviation and technology has shaped his unique career path. While his dream was to become an airline pilot, his proficiency in computer programming led him to a successful career in the tech industry.

Today, Rick's journey showcases the intersection of his two passions. He became a flight instructor, software developer, and eventually a jet owner. And throughout his experiences, he emphasizes the value of aviation as a business tool while discussing the future of technology in the aviation industry.

In the late 1980s and early 1990s, when the aviation industry faced significant challenges, Rick found himself writing basic software code for various companies. As technology was still predominantly mainframe-based, his expertise in computer programming provided him with a competitive advantage.

Rick's career in tech progressed rapidly as he became a software engineering manager and later pursued an MBA. Despite his success in the tech industry, though, he continued teaching people to fly while building his own flight hours as a cargo pilot.

Discovering Airplanes as Practical Business Tools

In the early 2000s, Rick purchased a quarter share in a Piper Comanche 260B which, recognizing the economic benefits of aviation and its potential as a competitive advantage, he used for business trips as well as visiting family across the country.

“With airplanes you juggle expense, carbon footprint and utility – that's how I like to look at it,” he says. “And, you know, I always found that I had some competitive advantage because I could get places faster and on my own schedule.

“There are businesses all over the place that use aviation for a competitive advantage within the economy. It's a strong business tool if used appropriately.

“It's also proven in the US that General Aviation provides communities with strong economic benefits, and I've always believed in that.”

Rick's involvement as a contract pilot for a real estate developer in Michigan highlighted the advantages of private aviation for business purposes. He stresses that owning an aircraft can significantly impact how a person or business operates in the market, enabling faster execution and expanded reach.

Although some still perceive private jets as being a luxury rather than a practical business tool, Rick believes that acquiring an aircraft earlier in the entrepreneurial journey can provide substantial value.

Rick’s Journey in Aircraft Ownership

He has owned and flown several airplanes over the years, including the Beechcraft Duchess, Cirrus SR22, Piper Meridian, and Cessna Citation Mustang, and while each aircraft has held sentimental value for him, he does have a favorite...

“There's no question about it. The Duchess was just a beautiful thing,” he reflects. “It was not very fast, but it was reliable and it didn't consume a lot of fuel. It was just an absolute joy to fly. I loved it.”

It was when Rick moved to Europe to work for a big tech firm for ten years that he bought a Cirrus SR22 to use both for leisure and business. He moved to Belgium and flew throughout Western and Eastern Europe, making weekly trips between Antwerp and London Biggin Hill. Indeed, it was in Europe that Rick had the opportunity to fly a Pilatus PC-12, and then moved on to own his first jet, a Cessna Citation Mustang.

Moving back to Texas initially, then Michigan, he owned a Piper Meridian before selling it and buying another Citation Mustang (which he lists as his second favorite plane, highlighting its suitability for frequent business travel across Florida, Texas and Michigan).

According to Rick, the Mustang's capabilities and efficiency made it an ideal choice for his missions at the time. But recently he upsized to a Cessna Citation M2, praising Cessna's engineering achievements. Since becoming familiar with the flight deck in the Cirrus SR22, Gamin’s avionics suites have been key factors in his choices of aircraft since then.

Rick Achieves the Unattainable with His Private Aircraft

With his parallel careers in technology and aviation, Rick finds fulfilment in achieving what he once thought was unattainable.

Though currently transitioning between executive positions and flying contracts, he aspires to someday retire and spend the next phase of his life fulfilling his childhood dream of flying for the airlines.

With his background in technology, Rick expresses concern about the aviation industry's cybersecurity vulnerability as airplanes become ever more connected, and he emphasizes the urgent need for [improved] cybersecurity measures and proactive strategies to protect aircraft systems.

Although the industry has made progress in accident analysis and safety, he believes that cybersecurity demands a different posture due to its far-reaching implications. 

Meanwhile, and in relation to his longed-for career with an airline, Rick sees a day coming when technology will push its way into the cockpit enough for there to be single pilot airline operations.

“I think the challenge, just like it is with AI today – and the transformation that it brings in our personal lives - is where you draw the line,” he moots. “Where do I feel safe as a person and where do I not?

“Do we want machines taking over the world, for example, making decisions for all of us? Of course not. And do we want an empty cockpit? I don't believe we'll ever put several people aboard an airplane and fly it like we do a drone because things go wrong. I do think single pilot...airline operations is a part of the very, very near future,” he predicts.

Rick typically flies single pilot when flying for himself, but he does fly multi-crew, too, as a volunteer for the US Coast Guard in a Cessna Citation M2 and Dassault Falcon jet. Once again, he highlights the Garmin avionics system as being excellent for reducing the workload and helping make single-pilot operations smooth.