E355: From 9/11 to Special Ops: Flying Secret Missions
Pilot to Pilot
Justin Siems
4.8 • 997 Ratings
🗓️ 3 March 2026
⏱️ 69 minutes
🧾️ Download transcript
Summary
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:
- The unconventional path into Air Force Special Ops
- What it feels like to deploy with barely 250 flight hours
- Flying through Saharan fuel-risk zones and Pacific icing
- The culture differences inside military aviation
- Why humility matters more than ego in elite units
- Building a company after walking away from a “dream job”
This one is raw, honest, and packed with perspective.
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Transcript
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| 0:00.0 | Episode 355 of the Piot to Piot Podcast takes off now. |
| 0:09.7 | The Pilot to Pilot podcast is brought to you by Ground School from the Finer Points, the indispensable training app for new and experienced pilots. |
| 0:17.4 | Visit LearntheFinerpoints.com, backslash Justin Justin to save 10% off your first year. |
| 0:22.5 | Fly with Garmin avionics, then grab your mobile device and make the Garmin pilot app your |
| 0:26.8 | cockpit companion. Get advanced functions you'll use before, during, and after every flight, |
| 0:32.7 | including updating your aircraft's databases and logging engine data, file fly log with garment pilot all pilots need |
| 0:41.8 | the big weather picture and i use serious xm aviation to check the fronts airmets segments turbulence |
| 0:47.5 | pyreps and more while i'm pre-flighting and in route all to give my passengers and me the most |
| 0:52.3 | comfortable flight possible and And now with the |
| 0:54.4 | latest offer from SiriusXM, there's never been a better time to upgrade your next flight with a Garmin |
| 0:59.2 | GDL 52 portable receiver to bring SiriusXM and ADSB weather plus traffic into your cockpit. |
| 1:06.5 | Hey, it's Justin. Quick question for you. Is your portfolio built to handle market swings? |
| 1:10.7 | Because the thing is, volatility doesn't care about your retirement date. All worst planning |
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| 1:19.9 | from smarter diversification and downside protection to tax smart moves and liquidity planning. |
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| 1:28.1 | significant wealth and want to stay ahead of the market shifts, this is time well spent. |
| 1:32.5 | Check it out at allworth airline.com slash Justin. My name is Tyler Flagg. I'm the founder and |
| 1:38.4 | CEO of flying company and it was a special operations pilot in the Air Force for about 14 years |
| 1:43.1 | before moving into corporate aviation |
| 1:45.7 | where I was the chief pilot for a PC 24. |
| 1:47.8 | That's kind of where I started building this company. |
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