Pilot to Pilot

Most pilots dream of smooth 10,000-foot runways.

Tyler Flagg trained to land a 30,000-pound aircraft on a 25-foot dirt strip… in total darkness.

After 9/11 changed his life trajectory, Tyler went from zero aviation background to flying Special Operations missions around the globe. With minimal information and maximum responsibility, he deployed into multiple combat theaters — moving elite teams into places most people will never see on a map.

In this episode:

1. The unconventional path into Air Force Special Ops
2. What it feels like to deploy with barely 250 flight hours
3. Flying through Saharan fuel-risk zones and Pacific icing
4. The culture differences inside military aviation
5. Why humility matters more than ego in elite units
6. Building a company after walking away from a “dream job”

This one is raw, honest, and packed with perspective.

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He's the most-requested guest in Pilot to Pilot history — and the wait was worth it. Trent Palmer, recreational bush pilot and one of aviation's most recognized YouTube creators, finally sits down with Justin for a raw, unfiltered conversation about the highs and lows of a life built around flying and filmmaking.

Trent opens up about his journey from RC helicopters and drone cinematography in Hollywood to becoming a full-time content creator — including how FAA regulations ironically pushed him into getting his pilot's license in the first place. But this episode goes far deeper than flying cool places and making beautiful videos.

Trent shares the gut-wrenching details of his engine failure in the Nevada backcountry, what it actually feels like when the prop stops and you have 45 seconds to find a field, and why the flight home may have been scarier than the emergency itself. He talks candidly about watching a close friend crash — and somehow survive — and how each close call reshapes your relationship with risk.

Then there's the FAA battle that nearly broke him. Trent walks through both investigations, the $50,000 in legal fees, the four-year court fight that went all the way to the Ninth Circuit, the license suspension he wishes he'd just accepted, and the personal toll of having your character questioned publicly.

This one is honest, emotional, and packed with lessons — whether you're a pilot, a content creator, or just someone who loves a great story.

What you'll hear:

1. From drones on Hollywood sets to bush pilot YouTuber
2. Engine failure over remote Nevada — the full story
3. Watching a friend crash and survive a "unsurvivable" impact
4. Two FAA investigations, $50K in legal fees, and hard lessons learned
5. How YouTube became his full-time career (and why he almost walked away)
6. Advice for pilots who want to start creating content
7. What's next: floats, new adventures, and maybe finally starting that podcast

Ever wonder what it's like to fly slower than freeway traffic — on purpose? Chancy Arnold is a banner tow pilot flying a Super Cub up and down the San Diego beaches, and in this episode he breaks down everything about the job. From the dive-and-hook pickup technique to four-hour flights strapped into a tiny seat with no breaks, Chancy gives an honest look at one of aviation's most unique time-building gigs. We talk about what it's really like flying at 50 knots indicated (and 15 knots ground speed in a headwind), how he built connections on the FBO ramp that got him the job, the territory system between banner towing companies, and flying over Padres games, golf tournaments, and gender reveals. Chancy also shares why he skipped the CFI route, why IFR was actually his favorite phase of training, and how he's stacking hours toward the airlines. Plus — look for Chancy in Volume 2 of the Pilot to Pilot Magazine with a full spread on building your time through banner towing.

What does it take to run one of the world's largest aviation events? Gene Conrad, President and CEO of the Aerospace Center for Excellence and Sun 'n Fun Aerospace Expo, pulls back the curtain on Florida's premier aviation gathering. Growing up in Oshkosh as the son of an airport director, Gene counted aircraft at EAA AirVenture as a teenager to see who had more planes. Now, he's running Sun 'n Fun—a six-day event that costs $7 million to produce, attracts over 60,000 attendees, and requires coordination with everyone from the U.S. Navy Blue Angels to Amazon Air operations. In this episode, you'll discover: - The real costs of running a major aviation event ($700K just for tents!) - How Sun 'n Fun coordinates with Amazon's massive Lakeland hub - Why they're making major schedule changes for 2025 - The difference between running an airport vs. running an air show - Future expansion plans including new 40,000 sq ft air-conditioned exhibit buildings - What makes Gene happiest: closing the airport because there's no more parking space - Behind-the-scenes secrets like the Island, the Swamp, and Chick-fil-A coming to the event Gene also shares candid insights about working with 3,000+ volunteers, learning from his biggest mistakes (like the WiFi disaster), and why his ultimate measure of success isn't attendance or revenue—it's making sure everyone goes home safe. Whether you're planning to attend Sun 'n Fun, curious about aviation event management, or just love air shows, this episode delivers insider knowledge you won't find anywhere else.

In Episode 351, Justin sits down with Ariel Johnson (@whiskeyflies on Instagram), a North Carolina-based flight instructor who earned her Citation type rating at just 800 hours. At not even 21 years old, Arielle shares her accelerated journey from discovering aviation at Sun ’n Fun to teaching students and flying corporate jets—all while completing her aviation degree.

This conversation explores the realities of flight training, the power of networking in aviation, and what it takes to break into corporate flying. Ariel discusses her experience getting typed in a Citation, the differences between Part 91 and 135 operations, and her approach to building a career through genuine relationships and hard work. She also offers candid advice for aspiring pilots on making the most of every rating, avoiding common pitfalls, and maintaining passion throughout the journey.

Whether you’re a student pilot wondering about your path forward, a CFI building time, or someone curious about corporate aviation opportunities, this episode delivers practical insights from someone who’s living proof that age is just a number when you combine dedication with smart networking.

Topics covered:

∙ Transitioning from private pilot to corporate jet operations

∙ The value of mentorship and networking in aviation

∙ Part 91 vs Part 135 flying: what to expect

∙ Getting a jet type rating early in your career

∙ Building flight time efficiently as a CFI

∙ Social media’s role in aviation careers

∙ North Carolina flying destinations (Wilmington, Oak Island, and more)