Our Team
Ross Kinkade (Co-Founder)
Ross Kinkade doesn’t just work in aviation — he rethinks it. Born in Washington and raised across Massachusetts and Illinois, his passion for flight took off early, boarding his first plane at just five days old. After graduating from the University of Illinois - Chicago with a degree in Urban Planning, Ross began his career in community development, helping cities grow smarter and stronger from the ground up. But it wasn’t long before his passion for aviation pushed him toward a different kind of infrastructure: the global network of air travel.
A hobby airline strategy game sparked the next chapter: a career pivot into aviation consulting. At Ricondo, Ross worked alongside industry veterans from Continental, United, and Qantas, gaining mentorship from global leaders in network planning, operations, and air service development. He supported major clients like Los Angeles World Airports (LAWA), the Chicago Department of Aviation, San Antonio International, and Munich Airport. He helped carriers including American, United, Qatar, China Southern, Air Berlin, and WOW Air rethink their networks, launch new routes, and unlock market opportunities others overlooked. His work ranged from passenger demand forecasting to strategic route development, giving him a front-row seat to the complexities of modern aviation.
Never one to settle for conventional wisdom, Ross blended aviation strategy with data analytics, sales, and software development, spending eight years in the Salesforce ecosystem and founding his own consulting firm. Inspired by the restless innovation of figures like Howard Hughes, Ross approaches aviation with a mindset of bold disruption — challenging assumptions, breaking through limitations, and designing smarter, faster, more resilient solutions for a changing industry. Ross isn’t here to follow industry blueprints — he’s here to rip them up, redraw the map, and build the future of aviation from scratch.
Today, Ross applies advanced technologies like AI, machine learning, and predictive analytics to aviation consulting, believing that the best strategies combine real-world expertise with forward-looking innovation. His work is defined by unconventional ideas, data-driven insights, and a commitment to bold, transformational thinking that pushes clients ahead of the curve.
Ross knows that every venture starts with a spark — and that the right idea, at the right time, can rewrite the future. He brings a unique lens to aviation consulting, fusing traditional industry knowledge with creative, technology-powered strategies built for the next generation of aviation leaders.
When he’s not working, Ross lives in the Grand Rapids area with his wife and infant son — usually sketching out new airline route maps or plotting the next big move long after bedtime.
Jonathan Rupp (Co- Founder)
Jonathan doesn’t just fly planes — he understands the entire aviation ecosystem from the ground up. Born in Iowa and raised in Minnesota, he graduated from Embry-Riddle Aeronautical University’s Daytona Beach campus with a degree in Aeronautical Science and minors in Business and Aviation Weather. From the beginning, Jonathan’s career blended leadership and hands-on aviation experience: serving as President, Chief Pilot, and Safety Officer of the Eagles Flight Team, supporting two FBOs during school, and earning deep operational insight early on.
After graduation, Jonathan spent nearly three years in airport operations at major hubs like Phoenix Sky Harbor and Atlanta International, where he gained firsthand experience managing the complex logistics of large-scale airport environments. Driven by a passion for flight, he transitioned into the cockpit, building over 4,000 hours of flight time since 2009 across aircraft like Challengers, Hawkers, King Airs, Citations, Pilatus, and Cirrus. His flying career has taken him across the Atlantic and Pacific Oceans, into more than a dozen countries, all 50 states, several Canadian provinces, Puerto Rico, and the Virgin Islands — spanning corporate charter, air ambulance, and fleet operations.
In addition to flying, Jonathan has served as a Fleet Chief Pilot, leading aircraft recoveries, developing operational strategies, managing pilot teams, and advising on growth initiatives. His leadership extended beyond the cockpit — shaping operational standards, improving fleet readiness, and helping organizations build stronger, more resilient aviation businesses. Jonathan doesn't just know aviation — he’s lived it from every angle, blending pilot-in-command experience with operational leadership to help clients build stronger, safer, smarter aviation businesses.
Jonathan’s wide range of experiences has given him deep, real-world insight into aviation regulations, aircraft capabilities, operational scaling, and evolving industry trends — blending technical expertise with practical leadership. He understands what it takes to run smarter aviation operations today, and what it will take to thrive in tomorrow’s rapidly evolving aviation environment.
Jonathan believes that strong aviation operations are built by those who understand both the regulations and the realities on the ground. Today, he helps aviation businesses design smarter, more resilient operations rooted in real-world experience, forward-thinking strategy, and a commitment to continuous improvement.
When he’s not flying or consulting, Jonathan lives on a horse farm he runs with his wife — an accomplished and decorated equestrian — raising their two daughters (ages 4 and 7 months) and staying just as competitive outside the cockpit.