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21.FIVE - Professional Pilots Podcast

21Five Podcast
21.FIVE - Professional Pilots Podcast
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  • 185. Late-Bloomer Pilot: Fractional, Regional, or Wait It Out?
    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 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 Our Sponsors Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast. Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more. Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you’re a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more. The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more. Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program. Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline’s plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more. VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more. ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.     Feedback & Contact Have feedback, suggestions, or a great aviation story to share? Email us at [email protected]. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates). The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.
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  • 184. How Do You Stay Resilient After Career Setbacks? w/ Capt Benny
    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. Follow Ben on Instagram @flybenfly Ben's WWII Aircraft Engine Youtube Channel @flightdojo Show Notes 0:00 Intro 2:29 Upgrading to Captain 9:45 It’s All Timing 13:56 The Interview Gauntlet 31:24 Pilot Career Stories 48:38 YouTube Deep Dive 56:38 Spirit Story Our Sponsors Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast. Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more. Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you’re a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more. The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more. Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program. Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline’s plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more. VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more. ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.     Feedback & Contact Have feedback, suggestions, or a great aviation story to share? Email us at [email protected]. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates). The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.
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  • 183. Can a Skydiver Pilot Make the Jump to the Big Leagues?
    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 Sponsors Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast. Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more. Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you’re a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more. The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more. Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program. Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline’s plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more. VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more. ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.     Feedback & Contact Have feedback, suggestions, or a great aviation story to share? Email us at [email protected]. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates). The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.
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  • 182. When the Flight Department’s Broken, Do You Stay or Go?
    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 showalter.com To contact Jim Lara, visit graystoneadvisors.com Show Notes 0:00 Intro 2: 23 Unprofessional Operations 14:59 Structure, Culture, Excellence 28:01 Plan B 33:38 Investigation Red Flags Our Sponsors Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast. Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more. Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you’re a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more. The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more. Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program. Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline’s plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more. VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more. ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.     Feedback & Contact Have feedback, suggestions, or a great aviation story to share? Email us at [email protected]. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates). The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.  
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  • 181. How Many Things Can Go Wrong on in the Idaho Backcountry?
    Max returns from the Idaho backcountry with a Cub full of stories—starter failures, in-flight repairs, surprise rafting, wildlife rescues, and nearly becoming the emergency contact for a hiker with a head injury. This standalone episode is a wild tale of aviation adventure, mechanical mayhem, and resourceful fixes. No mailbag or flight advice this time—just pure story time from the sticks. Strap in and enjoy the highs (and literal downdrafts) of off-the-grid bush flying. Show Notes 0:00 Intro 3:35 The Adventure Begins… 14:41 Darkness Falls 28:47 Heading Out 40:36 TL;DR Highs and Lows Our Sponsors Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast. Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more. Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you’re a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more. The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds. Click here to learn more. Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program. Harvey Watt — Offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline’s plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Click here to learn more. VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more. ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.     Feedback & Contact Have feedback, suggestions, or a great aviation story to share? Email us at [email protected]. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates). The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.  
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Sobre 21.FIVE - Professional Pilots Podcast

A podcast for Professional Pilots, by Professional Pilots. Join hosts Dylan and Max, both professional pilots with backgrounds in Flight Instructing, Airlines, and Business Aviation, on their quest to improve as travelers, pilots, and professionals. Expect to find interesting conversations with industry experts in a variety of aviation fields, thought-provoking discussions on hot topics, and hilarious stories from the (sometimes) wild aviation industry. Whether you’re corporate, airline, charter, or anywhere in between, you’ll love our fresh and often funny take on all things aviation. Come find us online at 21fivepodcast.com and connect with us via Insta/Facebook/Twitter: @21fivepodcast
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