#165 - Flight Decks, Financial Freedom, and the Pilot Community with Dylan and Max of 21.Five

Join us on October 8–9, 2026, in Las Vegas, Nevada for the first-ever Passive Income Pilots Conference. Learn how to build smarter wealth beyond the cockpit: https://www.passiveincomepilots.com/pip-conference

The path beyond the cockpit can change everything. Tait Duryea and Ryan Gibson sit down with Dylan and Max for a crossover conversation on aviation careers, financial education, and building a platform that serves pilots. They discuss corporate versus airline flying, the realities of side gigs, and why pilots need reliable guidance on taxes, real estate, passive investing, and estate planning. The conversation also highlights how both podcasts help aviators make more informed decisions with their careers, time, and growing income.

Dylan and Max are the hosts of the 21.5 Podcast, a show for professional pilots covering aviation careers, training, industry updates, and unique flying stories. Both began their careers as flight instructors after attending Embry-Riddle, then built experience in regional and corporate aviation. Through more than 200 episodes, they offer practical perspective and help fellow pilots ask better questions about their careers and the industry.

Show notes:

(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference 

(3:00) Max’s airline and corporate path

(7:12) Dylan on corporate flying careers

(10:46) Finding a corporate side gig

(14:29) Why the 21.5 Podcast began

(20:13) Financial education for high-income pilots

(27:01) Building a pilot-focused wealth strategy

(31:12) Why high earners need planning

(41:07) Active versus passive real estate

(53:14) Creating unbiased pilot financial education

(59:37) Outro

Connect with Dylan and Max:

• Website: https://www.21fivepodcast.com/

Related Episode: 

• #10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis
• #14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis

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*Legal Disclaimer*

The content of this podcast is provided solely for educational and informational purposes. The views and opinions expressed are those of the hosts, Tait Duryea and Ryan Gibson, and do not reflect those of any organization they are associated with, including Turbine Capital or Spartan Investment Group. The opinions of our guests are their own and should not be construed as financial advice. This podcast does not offer tax, legal, or investment advice. Listeners are advised to consult with their own legal or financial counsel and to conduct their own due diligence before making any financial decisions.