Passive Income Pilots

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 answers real-world questions about self-storage investing, tax withholding, privacy trusts, cost segregation, retirement conversions, and depreciation recapture. Pilots and high-income professionals will gain a clearer understanding of how to structure investments, protect real estate assets, avoid costly tax mistakes, and evaluate opportunities to generate passive income without adding unnecessary responsibilities to their already demanding careers.

Show notes:

(0:00) Intro

(3:27) Self-storage market outlook

(6:56) House hacking and privacy trusts

(7:34) Managing tax withholding strategically

(12:20) Replacing captain pay passively

(13:16) Homestead and privacy trusts

(16:10) Cost segregation on older rentals

(17:00) Investing without active real estate

(17:49) Naming trusts for asset privacy

(21:41) Leveraging paid-off rental properties

(27:28) Using real estate professional status

(32:28) Outro

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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 leverage, and estate planning, the panel examines how different pieces of a wealth plan fit together. Pilots will leave with practical guidance on deploying capital more efficiently while balancing tax savings, liquidity, retirement planning, and long-term financial freedom.

Show notes:

(0:00) Intro

(1:56) Where to hold investment cash

(3:26) STR depreciation recapture strategies

(5:57) Moving beyond a scarcity mindset

(8:18) Short-term rental tax qualification

(11:58) When passive income becomes enough

(14:49) Traditional-to-Roth conversion strategies

(18:45) Choosing cash versus retirement funds

(23:12) Optimizing pilot 401(k) contributions

(32:28) Financing short-term rental properties

(36:43) Avoiding major estate planning mistakes

(45:31) Outro

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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. They also discuss preparing for market corrections, creating life-changing income through a “get rich slow” strategy, tax advantages of alternative investments, and managing dozens of K-1s. For pilots looking to build additional income without relying entirely on the stock market, this episode offers a long-term investor’s perspective.

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

(2:28) Jeremy Roll’s investing background

(4:21) Investing through market cycles

(7:21) Preparing for a market correction

(11:43) Market concentration and margin debt

(16:34) Diversifying beyond the 401(k)

(18:59) Building life-changing passive income

(23:38) The get rich slow strategy

(26:30) Tax advantages of alternatives

(30:44) Where Jeremy is investing today

(33:35) Managing multiple K-1s

(37:18) Outro

Connect with Jeremy Roll:

• Email: [email protected] 
• LinkedIn: 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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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 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 

(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
• #85 - Cost Segregation: The Tax Strategy You Can’t Afford to Ignore with Erik Oliver
• #144 - Depreciation, Cost Segs, and the IRS Rules Pilots Miss with Brandon Hall
• #145 - Bonus Depreciation & Cost Seg: The Tax Strategy Pilots Can’t Ignore with Gian Pazzia

Book Reference:

• Optimize YOUR Bnb

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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 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 

(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/ 
• Larry’s email: [email protected] 
• Larry’s LinkedIn: https://www.linkedin.com/in/larry-lemer-0503aa5/  
• Mark’s LinkedIn: https://www.linkedin.com/in/mark-goldstein/ 
• Link to their Book: 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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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 snowboarding and Wall Street to real estate and privatized banking. Chris shares lessons from building businesses, surviving financial setbacks, owning dozens of rental units, and completing hundreds of flips before discovering the Infinite Banking Concept. They examine how specially designed whole life policies can support private lending, real estate investing, debt strategies, and greater control over capital while highlighting the discipline required to make the strategy work.

Chris Naugle is a wealth educator, entrepreneur, real estate investor, and former registered investment advisor specializing in privatized banking and the Infinite Banking Concept. A former professional snowboarder, Chris built multiple businesses before moving into financial services, real estate investing, and private lending. His experience includes managing investment assets, completing hundreds of house flips, appearing on HGTV’s Risky Builders, and building systems designed to help investors take greater control of their capital. 

Show notes:

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

(8:00) Chris Naugle’s wealth-building journey

(13:54) Building a business at seventeen

(18:31) Transition from retail to Wall Street

(26:32) Building a financial advisory career

(29:24) First lessons in real estate

(36:20) Hitting the real estate debt wall

(41:51) From house flipping to HGTV

(44:05) Discovering privatized banking

(49:06) Rethinking traditional money strategies

(51:30) Infinite banking versus securities-backed credit

(57:25) Outro

Connect with Chris Naugle:

• Website: https://www.chrisnaugle.com/ 
• LinkedIn: https://www.linkedin.com/in/thechrisnaugle/ 
• YouTube: https://www.youtube.com/thechrisnaugle 

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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 how a booking platform is changing the way pilots plan their getaways and owners market airport-adjacent properties. They share why general aviation travelers need more than a runway, what makes a stay truly pilot-friendly, and how Fly-Inn bridges the gap between landing and enjoying the destination. The conversation also considers the opportunity for pilots with short-term rentals, from meeting core hosting requirements to serving a highly specific guest base.

Carollyne Carmichel and Kenya Hodson are the mother-daughter founders of Fly-Inn, a short-term rental platform created for general aviation travelers. Built around pilot-friendly lodging, Fly-Inn connects guests with properties that offer nearby landing access, aircraft security, and ground transportation. Carollyne is a passionate general aviation pilot and property owner, while Kenya helps grow the platform through operations and technology.

Show notes:

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

(7:30) Fly-Inn’s pilot-first booking platform

(9:30) From boring destinations to business

(13:18) Private strips and nearby airports

(19:43) How hosts and Fly-Inn earn

(24:15) Landing permission at private strips

(26:14) Five promises for every host

(28:05) Short-term rental considerations

(31:03) What makes destinations perform

(33:28) Referring pilot-friendly properties

(38:24) Sync calendars across booking platforms

(39:02) Outro

Connect with Carollyne and Kenya:

• Website: https://www.fly-inn.com/
• Carollyne's LinkedIn: https://www.linkedin.com/in/carollyne-b-carmichel-833-i-fly-inn/ 
• Kenya’s IG: https://www.instagram.com/kenyahodsont/ 

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

Join us on October 8–9, 2026, at the M Resort and Casino in Las Vegas 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 Adam Kintigh of Nevada Corporate Headquarters to explain how pilots and investors can use LLCs, trusts, and business entities more effectively. They discuss why forming an LLC is only the first step, the risks of commingling funds and poor recordkeeping, and when separate entities may make sense for rentals, investments, and active businesses. Adam also shares practical ways to keep compliance simple while building stronger asset protection.

Adam Kintigh is a Senior Coach at Nevada Corporate Headquarters, where he helps business owners and investors structure entities, protect assets, and maintain proper compliance. With 25 years of experience, including more than 18 years with NCH, Adam works alongside legal, tax, estate-planning, and business-credit professionals to help clients build practical entity strategies.

Show notes:

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

(3:54) A costly corporate recordkeeping mistake

(6:34) Corporate formalities and LLC structures

(9:31) Why DIY LLCs create risk

(12:34) What an LLC actually protects

(14:23) LLCs versus S-corps for investors

(23:25) Records, resolutions, and meeting minutes

(25:34) Keeping multiple entities manageable

(28:30) Compliance for S-corps and C-corps

(32:29) Asset protection for three investor levels

(40:08) Partnerships, short-term rentals, and K-1s

(48:13) Outro

Connect with Adam Kintigh:

• Website: https://nchinc.com 
• Email Adam at: [email protected] and mention Passive Income Pilots to get started.
• NCH Consultation Phone: 1-800-508-1729 

Learn more about: 

NCH Consultation for Passive Income Pilots Investors: https://calendly.com/nchconsultation/nch-consultation-for-pipp?month=2025-12

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/

—

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/ 

Join our growing community on Facebook: https://www.facebook.com/groups/passivepilots

Check us out on Instagram @PassiveIncomePilots: https://www.instagram.com/passiveincomepilots/

Follow us on X @IncomePilots: https://twitter.com/IncomePilots

Get our updates on LinkedIn: https://www.linkedin.com/company/passive-income-pilots/

Do you have questions or want to discuss this episode? Contact us at [email protected] 

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.

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

A practical path to business ownership. Tait Duryea and Ryan Gibson sit down with Brenda Gage, a pilot spouse who turned a long-time goal of business ownership into a growing café portfolio. Brenda shares how she found established, cash-flowing businesses, evaluated opportunities on BizBuySell, used SBA financing, and pushed through lender rejections. She also explains why culture, employee retention, and a respectful seller transition matter just as much as the numbers. This episode offers a grounded look at acquiring a business beyond franchises or real estate.

Brenda Gage is the owner of a growing chain of Washington cafés and Larson’s Bakery. Married to an Alaska Airlines pilot, she built a flexible career around family life before acquiring eight cafés through SBA financing. In three years, she helped grow annual revenue from approximately $16.7 million to $21 million. Brenda shares practical insights on finding established businesses, securing the right lending partner, leading employees through ownership transitions, and preserving the legacy of family-owned companies.

Show notes:

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

(3:54) Brenda’s path to business ownership

(6:46) Finding cash-flowing businesses online

(8:35) Growing the café business

(12:57) How BizBuySell works

(17:07) Criteria for legacy businesses

(21:07) Leading without industry expertise

(26:03) Funding an acquisition with SBA loans

(32:32) Finding the right SBA lender

(40:35) How a business purchase closes

(42:46) Leading staff through ownership change

(48:46) Outro

Connect with Brenda Gage:

• Website: https://www.cafesinc.com/ 
• LinkedIn: https://www.linkedin.com/in/brenda-gage-12796592/ 

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/

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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.