Legal Gray Areas For Pilots, with Mark Kolber

By John Zimmerman
Apr 7, 2026
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Pilot's Discretion Podcast, episode 127

Too many pilots miss out on fun and rewarding flying experiences because they’re afraid of legal gray areas, according to aviation lawyer and flight instructor Mark Kolber. He shares the facts about cost sharing, ramp checks, and medical applications, with practical advice for staying out of trouble with the FAA. Mark is also a longtime CFI, so he also offers tips for learning to fly later in life and transitioning to new airplanes. In the Ready to Copy segment, you’ll hear about flying in Colorado, Carolina barbecue, and lawyer jokes.

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Quotes:

What the FAA does care about right now: “it's an enforcement priority to be looking at illegal charters.”
How often do FAA enforcement actions happen? “Very rarely.”
Will cost-sharing apps ever be legal? “I think the chances are pretty slim to none.”
FAA powers on a ramp check: “they can't board an aircraft without the pilot or the operator’s or the owner's permission. They can't detain people. They don't have any arrest powers.”
Critical advice: “the one thing you never ever want to do is be dishonest with the inspector. For some reason, they always know.”
What to do if the FAA calls: “when the FAA or a FSDO shows up on your phone, don't answer it… let them leave a message and then call them back at your leisure.”
How aviation attorneys can help: “in most cases, I would say the FAA doesn't even know that I'm involved. I'm in the background, just advising.”
What to do if ATC says to call the tower: “you want to listen more than you talk”
Tips for CFIs working with older pilots: “you have to accept that it's not their full-time job to learn how to fly.”
What really counts for transition training: “get out there and get the stalls, get the steep turns, learn how the aircraft performs at its edges.”
The best advice for new CFIs: “Talk to your students and listen. Find out how they learn rather than how you teach.”