185. Late-Bloomer Pilot: Fractional, Regional, or Wait It Out?
21.FIVE - Professional Pilots Podcast
Release Date: 10/07/2025
191. Should You Sign a $75K Contract Just to Chase PIC Time?
21.FIVE - Professional Pilots Podcast
Dylan recaps his brutal post-“ATC meltdown” commute and rants about the GA ban at 12 major airports while Max counters with cub flying and Chicago layover tips (including a dangerously spicy El Chingón). In the mailbag, listeners call the guys out for drifting toward aspiring-pilot advice, recommend MU-2 and airline YouTube channels, drop a credit-card points hack for flight training, and share how they commute to FedEx in their own airplane. Flight Advice closes the show with a regional FO at a United feeder wrestling with whether to jump to a GoJet direct-entry captain gig that requires...
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190. What’s Next for BizAv Pilot Compensation?
21.FIVE - Professional Pilots Podcast
Dr. Chris Broyhill returns to break down the latest Air Comp Calculator data and what it means for 2025 pilot compensation. Dylan and Max dig into the trends, the slowdown in wage growth, and how bizav departments are navigating post-COVID market corrections. They also talk negotiation strategy, job titles that actually matter, and Broyhill’s new 600-page industry textbook, The Business Aviation Book: Leading Operational Excellence. Finally, they wrap up the episode with a discussion on the Go/No Go specialty course Dr. Broyhill used to teach at a large training center. Check out ...
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189. Can You Survive 900 Hours a Year on a One-Hour Callout?
21.FIVE - Professional Pilots Podcast
Max kicks off his annual training rant—breaking down the highs, lows, and downright absurd moments of recurrent at “the training center.” Dylan adds perspective on flight training efficiency and why a great instructor makes all the difference. The mailbag delivers everything from a new layover guide in Portsmouth to a 14-year-old aircraft dealer to a Marine pilot navigating a tricky transition to the airlines, plus a Learjet Pilot with a 1 hour call-out seeks guidance. In Flight Advice, a hard-working pilot is stalled out waiting for the industry to start moving again. Show Notes 0:00...
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188. How Can Pilots Build Wealth Beyond the Flight Deck?
21.FIVE - Professional Pilots Podcast
Tim Pope, CFP® and founder of 360 Aviation Advisors, joins Dylan and Max to talk about how pilots can make smarter financial moves—on and off the line. From variable pay to early retirement and crashpad cash flow, Tim breaks down what makes pilot finances uniquely tricky and how to stay ahead of turbulence. The crew also dives into taxes, scheduling volatility, and the “golden handcuff” problem in today’s airline contracts. Tune in for real-world money talk that every professional pilot should hear before their next recurrent. Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL...
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187. Is turbine PIC in 91/135 the fastest lane to legacy?
21.FIVE - Professional Pilots Podcast
We kick off with Southwest red-eye shenanigans, hot/high GA drama departing PRC in a 150, and Max’s backcountry “mesa strip” adventure (with hard data from the STOL-mate). The Mailbag is full: 2,500-hour 135 pilots debating regionals, cockpit sun-shade gear, commuting to MEM in your own A36, first flights post-PPL, time-building without a CFI, and making that first 91/135 SIC→PIC jump. Flight Advice tackles the big one: take a regional CJO now or accept a 135 upgrade for immediate PIC while a baby’s on the way — we weigh time-to-legacy, family timing, and logbook strategy. Show...
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186. First Officers: How Do You Speak Up Without Getting Shut Down?
21.FIVE - Professional Pilots Podcast
Colin and Mara'D—both airline FOs and cast members from The Rehearsal—join Max and Dylan to dissect the tricky dynamics of speaking up in the right seat. Why is it so hard, and what makes it easier? The crew digs into SOP gaps, CRM training, real-world examples like Asiana 214, and the subtle art of being a chameleon in the cockpit. Plus: bizav vs. 121 culture, and how personality plays a bigger role than you think. Check out Season 2 of The Rehearsal to watch Mara'D (episode 2) and Colin (episode 4) Show Notes 0:00 Intro 2:15 Speaking Up 13:00 Getting Involved in the Show 17:41 Wings of...
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185. Late-Bloomer Pilot: Fractional, Regional, or Wait It Out?
21.FIVE - Professional Pilots Podcast
Dylan opens from an echo chamber (literally) and the guys kick around first impressions of Gulfstream’s newly announced G300 versus the G280—windows, avionics, “longest cabin,” and whether depreciation and warranty keep the new-metal carousel spinning. Mailbag hits everything from those mysterious skid marks on SNA 20R and whether an RJ type helps more than becoming a check instructor, to Phoenix haboobs, GA commuting from the islands, and a listener swag request. Flight Advice: a 40-year-old “late bloomer” with 1,600 TT/500 multi weighs fractionals vs. regionals; Dylan and Max lay...
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184. How Do You Stay Resilient After Career Setbacks? w/ Capt Benny
21.FIVE - Professional Pilots Podcast
Benjamin Bailey (@flybenfly) joins Max and Dylan for an honest, hilarious deep dive into aviation’s influencer world, airline interview faceplants, and the realism gap on pilot social media. For professional pilots, this episode cuts through the curated BS to talk timing, authenticity, and bouncing back after setbacks. From CRM failures to career detours, Ben brings the real talk with a dose of humor. Hit play and subscribe for the stories you're not getting on your For You page. Show Notes 0:00 Intro 2:29 Upgrading to Captain 9:45 It’s All Timing 13:56 The Interview Gauntlet 31:24 Pilot...
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183. Can a Skydiver Pilot Make the Jump to the Big Leagues?
21.FIVE - Professional Pilots Podcast
Max rants about St. Louis still acting like it’s O’Hare, but enjoys the accomodations. The mailbag covers creative GA commuting strategies and whether backcountry camping flights belong on a professional resume. Ted calls in on his drive home from the airport to share some bidding tips. Flight Advice closes with a skydiver pilot wondering if it’s time to trade jumpers for smokejumpers with the USFS—and what that career path really looks like. Show Notes 0:00 Intro 5:19 Max’s Musings 13:24 Reviews & Comments 16:40 Mailbag 31:18 Straight Talk with Ted 45:41 Flight Advice Our...
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182. When the Flight Department’s Broken, Do You Stay or Go?
21.FIVE - Professional Pilots Podcast
A listener asks the question every pro pilot eventually faces: should you stay put and try to fix what’s broken in your flight department, or cut bait and move on? Dylan and Max bring in Jenny Showalter and Jim Lara to explore the real-world tradeoffs. From career coaching to leadership insights, they share what to weigh before pulling the ripcord—or digging in to make change happen. It’s candid talk about loyalty, burnout, and how to navigate tough calls in business aviation. To contact Jenny Showalter, visit To contact Jim Lara, visit Show Notes 0:00 Intro 2: 23 Unprofessional...
info_outlineDylan opens from an echo chamber (literally) and the guys kick around first impressions of Gulfstream’s newly announced G300 versus the G280—windows, avionics, “longest cabin,” and whether depreciation and warranty keep the new-metal carousel spinning.
Mailbag hits everything from those mysterious skid marks on SNA 20R and whether an RJ type helps more than becoming a check instructor, to Phoenix haboobs, GA commuting from the islands, and a listener swag request.
Flight Advice: a 40-year-old “late bloomer” with 1,600 TT/500 multi weighs fractionals vs. regionals; Dylan and Max lay out a strategy heavy on networking, patience, and targeted moves.
Plus: disc golf as the stealth layover hack and a quick ode to SAN’s shiny new terminal vibes.
Show Notes
0:00 Intro
3:34 G300 Thoughts & Musings
27:26 Reviews
30:08 Mailbag
45:14 Flight Advice
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