Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success.
Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life.
Whether you're a seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.
#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 how diversification can protect long-term retirement income. They also cover compounding passive cash flow, syndications, tax advantages, K-1 management, and why Jeremy is currently keeping substantial liquidity available while waiting for better investment opportunities.
Jeremy Roll is the Founder and President of Roll Investment Group and a longtime passive investor in real estate and private businesses. Before becoming a full-time investor, he spent more than a decade in the corporate world, including roles at Disney and Toyota, and earned his MBA from The Wharton School. Jeremy is also a co-founder of For Investors By Investors (FIBI), a nonprofit investor education and networking community. Known for his disciplined, research-driven approach, he has participated in more than 200 managed investments over his investing career.
Show notes:
(0:00) Intro
(4:38) Jeremy Roll’s investing background
(6:31) Investing through market cycles
(9:31) Preparing for a market correction
(13:53) Market concentration and margin debt
(18:44) Diversifying beyond the 401(k)
(21:09) Building life-changing passive income
(25:48) The get rich slow strategy
(28:40) Tax advantages of alternatives
(32:54) Where Jeremy is investing today
(35:45) Managing multiple K-1s
(39:28) Outro
Connect with Jeremy Roll:
Email: jroll@rollinvestments.com (mailto:jroll@rollinvestments.com)
LinkedIn: linkedin.com/in/jeremy-roll-655107 (http://linkedin.com/in/jeremy-roll-655107)
If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ (https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/)
—
You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry.
Remember to subscribe for more insights at PassiveIncomePilots.com (https://passiveincomepilots.com/)! https://passiveincomepilots.com/ (https://passiveincomepilots.com/)
Join our growing community on Facebook (https://www.facebook.com/groups/passivepilots): https://www.facebook.com/groups/passivepilots
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Get our updates on LinkedIn (https://www.linkedin.com/company/passive-income-pilots/): https://www.linkedin.com/company/passive-income-pilots/
Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com (https://dashboard.cohostpodcasting.com/shows/b8533308-b73a-4c43-b53a-208f10249eff/episodes/4b9b4b83-858d-4e44-86c4-a3accf1c6fdc/ask@passiveincomepilots.com)
See you at the next one!
*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.
30 Sept 2026
#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 (https://www.passiveincomepilots.com/pip-conference)
Tait Duryea and Ryan Gibson examine the side of real estate investing that spreadsheets often miss, the return on life. Drawing from their own experiences with rental properties, they discuss when active ownership is worth the time, why so-called passive investments can start to feel like another job, and how pilots should think about short-term rentals beyond the tax benefits. They also cover cost segregation, bonus depreciation, depreciation recapture, 1031 exchanges, and why buying assets you are comfortable holding long term can matter. For pilots focused on tax efficiency and financial independence, this episode offers a practical look at what real estate ownership can actually require.
Show notes:
(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference (https://www.passiveincomepilots.com/pip-conference)
(0:54) Reality of active real estate investing
(2:24) Measuring your return on life
(6:50) Tait’s costly multifamily lesson
(11:10) Moving from active to passive investing
(13:24) Short-term rentals and tax benefits
(14:51) Grade the deal and lifestyle
(19:56) Short-term rentals are hospitality businesses
(24:28) Cost segregation and CPA planning
(28:43) Depreciation recapture when selling
(32:37) Buying assets for long-term wealth
(37:54) Outro
Related Episodes:
#32 - Tax Savvy Investing: The Power of Cost Segregation with Yonah Weiss (https://podcasts.apple.com/us/podcast/32-tax-savvy-investing-the-power-of-cost/id1675913577?i=1000624538776)
#85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver (https://podcasts.apple.com/us/podcast/85-cost-segregation-the-tax-strategy-you-cant-afford/id1675913577?i=1000677510087)
#144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall (https://podcasts.apple.com/us/podcast/144-depreciation-cost-segs-and-the-irs-rules-pilots/id1675913577?i=1000747026348)
#145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia (https://podcasts.apple.com/us/podcast/145-bonus-depreciation-cost-seg-the-tax-strategy/id1675913577?i=1000748224707)
Book Reference:
Optimize YOUR Bnb (https://www.amazon.com/dp/099971550X?lv=shuf&channelId=500&plpRedirect=mhFallback)
If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ (https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/)
—
You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry.
Remember to subscribe for more insights at PassiveIncomePilots.com (https://passiveincomepilots.com/)! https://passiveincomepilots.com/ (https://passiveincomepilots.com/)
Join our growing community on Facebook (https://www.facebook.com/groups/passivepilots): https://www.facebook.com/groups/passivepilots
Check us out on Instagram @PassiveIncomePilots (https://www.instagram.com/passiveincomepilots/): https://www.instagram.com/passiveincomepilots/
Follow us on X @IncomePilots (https://twitter.com/IncomePilots): https://twitter.com/IncomePilots
Get our updates on LinkedIn (https://www.linkedin.com/company/passive-income-pilots/): https://www.linkedin.com/company/passive-income-pilots/
Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com (https://dashboard.cohostpodcasting.com/shows/b8533308-b73a-4c43-b53a-208f10249eff/episodes/4b9b4b83-858d-4e44-86c4-a3accf1c6fdc/ask@passiveincomepilots.com)
See you at the next one!
*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.
25 Sept 2026
#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 (https://www.passiveincomepilots.com/pip-conference)
Tait Duryea and Ryan Gibson sit down with Larry Lemer and Mark Goldstein of Foliage to examine how a community of accredited investors approaches commercial real estate together without pooling money or making investment recommendations. They cover Foliage’s syndicator vetting process, its extensive due diligence questions, operator trust and execution, portfolio diversification, and lessons learned from deals that did not go as planned. For pilots and high-income professionals considering alternative investments, the conversation shows how surrounding yourself with experienced investors can bring additional perspectives to your own decision-making.
Larry Lemer and Mark E. Goldstein are co-founders of Foliage, a private investor education group that brings together accredited investors, including airline pilots, to evaluate commercial real estate opportunities. Larry brings roughly 20 years of real estate investing experience, while Mark draws on his corporate leadership and private equity background. Together, they emphasize rigorous due diligence, trusted operators, and the value of learning from a network of experienced investors.
Show notes:
(0:00) Passive Income Pilots Conference announcement: https://www.passiveincomepilots.com/pip-conference (https://www.passiveincomepilots.com/pip-conference)
(1:03) How Foliage vets syndicators
(5:23) How the group started
(9:11) Value of diverse investor perspectives
(14:05) Foliage is not a fund
(18:10) Education through the syndication playbook
(18:47) Case for alternative assets
(22:19) Lessons from investing mistakes
(25:01) Understanding deals and trusting operators
(30:38) Red flags when vetting syndicators
(40:44) Outro
Connect with Larry Lemer and Mark Goldstein:
Website: https://www.foliageig.com/ (https://www.foliageig.com/)
Larry’s email: larry@foliageig.com (mailto:larry@foliageig.com)
Larry’s LinkedIn: https://www.linkedin.com/in/larry-lemer-0503aa5/ (https://www.linkedin.com/in/larry-lemer-0503aa5/)
Mark’s LinkedIn: https://www.linkedin.com/in/mark-goldstein/ (https://www.linkedin.com/in/mark-goldstein/)
Link to their Book: https://amzn.to/4rxzrn9 (https://amzn.to/4rxzrn9)
If you’re interested in participating, the latest institutional-quality self-storage portfolio is available for investment now at: https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/ (https://turbinecap.investnext.com/portal/offerings/8449/houston-storage/)
—
You've found the number one resource for financial education for aviators! Please consider leaving a rating and sharing this podcast with your colleagues in the aviation community, as it can serve as a valuable resource for all those involved in the industry.
Remember to subscribe for more insights at PassiveIncomePilots.com (https://passiveincomepilots.com/)! https://passiveincomepilots.com/ (https://passiveincomepilots.com/)
Join our growing community on Facebook (https://www.facebook.com/groups/passivepilots): https://www.facebook.com/groups/passivepilots
Check us out on Instagram @PassiveIncomePilots (https://www.instagram.com/passiveincomepilots/): https://www.instagram.com/passiveincomepilots/
Follow us on X @IncomePilots (https://twitter.com/IncomePilots): https://twitter.com/IncomePilots
Get our updates on LinkedIn (https://www.linkedin.com/company/passive-income-pilots/): https://www.linkedin.com/company/passive-income-pilots/
Do you have questions or want to discuss this episode? Contact us at ask@passiveincomepilots.com (https://dashboard.cohostpodcasting.com/shows/b8533308-b73a-4c43-b53a-208f10249eff/episodes/4b9b4b83-858d-4e44-86c4-a3accf1c6fdc/ask@passiveincomepilots.com)
See you at the next one!
*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.
Who has been a guest on Passive Income Pilots
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Dan Monlux
Amanda Wynalda
Dr Peter Linneman
Thomas Castelli
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