Episodes
#173 - The Rich Man’s Roth: A Smarter Way to Retire Tax-Free with Brenyn McConell and Blake Brogan
Tait Duryea and Ryan Gibson sit down with Money Insights wealth strategists Brenyn McConnell and Blake Brogan to explore how pilots can create more tax-efficient retirement income beyond a traditional 401(k). They break down how properly structured whole life insurance can provide liquidity, tax-fre...
#172 - Pilot Wealth Q&A: Taxes, Trusts, Real Estate, and Passive Income
Tait Duryea and Ryan Gibson close out the Passive Income Pilots Conference with a rapid-fire Q&A alongside experts Koy Harris, David Vanlandingham, Kurt Harris, and Adam Kintigh. Drawing on their expertise in estate planning, asset protection, business structuring, and tax strategies, the panel answ...
#171 - From STRs to Roth IRAs: A Pilot’s Wealth Playbook
Tait Duryea and Ryan Gibson host a live Q&A with Adam Kintigh, Kurt Harris, and David Vanlandingham covering the financial questions pilots face as their income and investments grow. From short-term rental tax strategies and Roth conversions to self-directed IRAs, 401(k) contributions, real estate l...
#170 - The Get Rich Slow Strategy for Passive Investors with Jeremy Roll
Tait Duryea and Ryan Gibson sit down with veteran passive investor Jeremy Roll to discuss building wealth beyond traditional stocks and 401(k)s. Jeremy shares how more than two decades of alternative investing shaped his approach to market cycles, diversification, liquidity, and passive cash flow. T...
#170 - The Get Rich Slow Strategy for Passive Investors with Jeremy Roll
Tait Duryea and Ryan Gibson sit down with veteran passive investor Jeremy Roll to discuss building wealth beyond traditional stocks and 401(k)s. Jeremy shares how alternative investments helped him leave the corporate world, why he believes investors should pay closer attention to market cycles, and...
#169 - When Passive Real Estate Isn’t Really Passive
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 Tait Duryea and Ryan Gibson examine the side of real estate investing that spreadsheets o...
#168 - How Smart Investors Vet Real Estate Deals Together with Larry Lemer and Mark Goldstein
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 Tait Duryea and Ryan Gibson sit down with Larry Lemer and Mark Goldstein of Foliage to exa...
#167 - From Wall Street to Infinite Banking with Chris Naugle
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 Tait Duryea welcomes Chris Naugle to discuss his unconventional path from professional sno...
#166 - Fly-Inn Rentals for Pilots and Investors with Carollyne Carmichel & Kenya Hodson
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 Tait Duryea and Ryan Gibson sit down with Carollyne Carmichel and Kenya Hodson to discuss ...