In this episode, Tait Duryea and Ryan Gibson sit down with Michael Meylor, a seasoned pilot and self-storage investor who has built an impressive portfolio without raising outside capital. Michael shares how he transitioned from military to commercial flying, how he and his wife started investing in single-family rentals, and why they pivoted to commercial self-storage. The episode covers everything from identifying the right-sized deals to financing with SBA loans, and even touches on family involvement, tax strategies, and the realities of active vs. passive investing.

Michael Meylor is a major airline pilot and former military aviator who has successfully built a self-funded real estate portfolio focused on self-storage facilities. With a background in tech and an MBA, Michael applied his analytical skills to real estate investing, scaling from single-family rentals to large commercial properties. Alongside his wife, he’s built a lean operation and shares practical insights into active investing, SBA loans, and family wealth-building strategies.

Show notes:

(0:00) Intro

(02:32) Overcoming fear of real estate investing

(06:21) Why self-storage and the first deal

(09:36) Adding value and refinancing strategy

(12:35) Learning financial modeling and analysis

(18:06) Where to get educated in self-storage

(23:34) Minimum viable size for self-storage

(27:11) Active investing: The reality check

(35:09) Why go active? The long-term upside

(45:22) Most surprising lesson from investing

(48:18) Outro

Connect with Michael Meylor:

• LinkedIn: https://www.linkedin.com/in/michael-m-4588101a/ 
• Website: https://greenlightstorage.com/ 
• Email: [email protected]

—

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/ 

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

See you on 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.

In this episode, Tait Duryea welcomes Gino Barbaro of Jake & Gino to unpack the mindset and mechanics behind building lasting wealth through multifamily real estate. Gino shares his journey from running a family restaurant to becoming a real estate investor with over 1,800 units. They explore topics like values-based decision-making, creating "happy money," the strategic use of whole life insurance for real estate investing, and how to teach financial stewardship to the next generation. This episode is a must-listen for high-income professionals looking to build freedom and legacy through smart investing.

Gino Barbaro is a multifamily real estate investor, author, and co-founder of Jake & Gino, an education platform focused on apartment investing. With a portfolio of over 1,800 units, Gino teaches others how to build wealth through multifamily real estate, values-based leadership, and financial literacy. He’s the author of Happy Money, Happy Family, Happy Legacy, which integrates money mindset with real estate investing and legacy building.

Show notes:

(0:00) Intro

(01:13) Life lessons from the family restaurant

(05:30) Why real estate is Gino’s chosen asset

(08:54) The philosophy behind "Happy Money"

(13:23) Saving vs. investing mindset

(19:54) Whole life insurance explained

(25:12) Teaching financial values to kids

(29:43) Why new investors struggle

(31:46) Exit strategies in real estate

(36:19) Current real estate market outlook

(42:18) Outro

Links mentioned: 

Optimize Your Policy: A Practical Workshop for Passive Income Pilots: https://youtu.be/higMHZI4Itw 

Schedule a Call with a member of the Money Insights team: https://moneyinsightsgroup.com/#schedule-call 

Connect with Gino Barbaro:

• LinkedIn: https://www.linkedin.com/in/gino-barbaro-03973b4b/ 
• Website: https://noteclubusa.com/ 

—

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/ 

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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 on 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.

In this episode, Tait Duryea and Ryan Gibson sit down with retired airline captain and seasoned investor Tom Force to discuss a real estate strategy many overlook—note investing. They cover tax strategies, risk management, and how to get started in note investing. If you’re tired of tenant headaches and want to invest like a bank, this episode is for you.

Tom Force, a retired airline pilot and real estate investor, found financial freedom through note investing. After years in rentals and development, he shifted to this truly passive strategy. Now, through Note Club USA, he helps pilots and investors build wealth with real estate notes.

Show notes:

(0:00) Intro

(04:46) Getting started in real estate investing

(09:16) Why Tom transitioned to note investing

(11:31) The appeal of note investing for pilots

(20:34) How note investing compares to rental real estate

(24:05) Why banks & investors sell mortgage notes

(28:56) The risk vs. reward of note investing

(35:35) Steps to start investing in notes

(38:09) Seller financing strategies & tax benefits

(45:18) Outro

Connect with Tom Force:

• LinkedIn: https://www.linkedin.com/in/tomforce/ 
• Website: https://noteclubusa.com/ 

—

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

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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 on 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.

Hangar space is in short supply, but Trenton Ray is changing that. In this episode, Tait Duryea and Ryan Gibson chat with Trenton about Hangar Direct, his platform that’s like Airbnb for hangars—making it easier for pilots to find and rent space. They dive into the supply shortage, investment potential, and what to know about leasing, financing, or building a hangar. 

Trenton Ray is a corporate pilot and aviation entrepreneur based in Austin, Texas. With experience flying various private and corporate jets, he saw firsthand the challenges pilots face in securing hangar space. This led him to co-found Hangar Direct, a platform that optimizes available hangar space, making it easier for aircraft owners to find and rent storage.

Show notes:

(0:00) Intro

(04:19) The frustration of finding hangar space

(05:25) Hangar Direct: The Airbnb for hangars

(07:43) Why demand for hangars is skyrocketing

(10:05) Optimizing underutilized hangars for better returns

(15:40) Is hangar ownership a good investment?

(17:23) Understanding land leases and hangar ownership risks

(24:11) How to finance a hangar: Loans vs. cash purchases

(33:09) Monetizing underused aircraft through dry leasing

(40:40) Outro

Connect with Trenton Ray:

• LinkedIn: https://www.linkedin.com/in/trenton-ray-56953812a/
• Website: https://www.hangardirect.com
• Instagram: https://www.instagram.com/HangarDirect 

—

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/

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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 on 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.

In this special 100th episode of Passive Income Pilots, Tait Duryea and Ryan Gibson take listeners behind the scenes of the podcast, sharing how it all started and what goes into creating each episode. They also dive into their personal journeys in aviation, investing, and entrepreneurship. From buying their first rental properties to scaling multi-million-dollar real estate portfolios, they discuss lessons learned, investment strategies, and what’s next for the market. Plus, they break down key economic trends, the impact of inflation, and why 2025 may be one of the best buying opportunities in real estate.

Show notes:

(0:00) Intro

(02:10) How Passive Income Pilots started

(05:12) Behind the scenes

(12:41) Real estate investing while flying

(19:03) Understanding the Cashflow Quadrant

(25:59) How Tait and Ryan got into real estate

(29:55) Inflation, interest rates, and the Fed’s impact

(34:57) Why now is a great time to buy real estate

(42:11) Market trends in multifamily and storage

(46:42) How to invest with Turbine Capital & Spartan Investment Group

(49:28) Outro

Invest with Tait & Ryan:

• Turbine Capital: https://www.turbinecap.com
• Spartan Investment Group: https://www.spartan-investors.com

—

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 on 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.

In this episode, Tait Duryea and Ryan Gibson connect with Zach Lemaster to explore the world of turnkey real estate and build-to-rent properties. They discuss the benefits and challenges of owning physical real estate, the tax advantages of rental properties, and how busy professionals can invest without becoming full-time landlords. Zach shares insights on market trends, the importance of expectation setting, and why new construction rentals might be a better option than traditional rehabs.

Zach Lemaster is the founder and CEO of Rent to Retirement, a leading turnkey real estate investment company. A former Air Force optometrist, Zach transitioned into real estate investing, building a successful portfolio of residential and commercial properties. He specializes in helping busy professionals acquire cash-flowing rental properties in high-growth markets, leveraging tax advantages and strategic financing. Through Rent to Retirement, he provides investors with turnkey opportunities, including build-to-rent properties, that offer passive income potential with minimal hands-on management.

Show notes:

(0:00) Intro

(4:49) Zach’s background: from Air Force to real estate

(7:37) Why real estate is the IDEAL investment

(18:52) What is turnkey real estate? Pros and cons

(28:15) The biggest surprises and challenges for new investors

(32:50) Build-to-rent: a growing investment trend

(40:15) The risks of leverage in real estate

(50:49) Outro

Connect with Zach Lemaster:

• LinkedIn: https://www.linkedin.com/in/zach-lemaster-7b1530238/ 
• Website: https://www.renttoretirement.com 

—

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 on 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.

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Valerie Cusano, an insurance expert with a background in law and decades of experience in commercial and residential insurance. Val dives deep into the critical aspects of real estate insurance, particularly for condo and rental property owners. She explains the difference between condo and homeowners insurance, key policy coverages investors should have, and how to evaluate a building’s financial health before buying in. The conversation also touches on industry trends, the role of insurance brokers, and how global factors impact insurance rates.

Valerie Cusano is a seasoned insurance expert with decades of experience in the industry. Originally a lawyer specializing in insurance defense, she transitioned into brokering and eventually founded her own insurance agency. Val has extensive commercial and residential insurance expertise, including coverage for high-net-worth individuals and real estate investors. In this episode, Val breaks down essential insurance strategies for pilots and investors, covering everything from policy selection to risk management.

Show notes:

(0:00) Intro

(03:09) Val’s background in law & insurance

(04:46) Key insurance considerations for rental properties

(07:18) Condo insurance vs. homeowners insurance

(08:57) Red flags when investing in condos

(12:41) The benefits of condo ownership

(18:48) Understanding global insurance markets & rising rates

(25:40) How to ensure your condo board gets the best rates

(36:29) How to find the right insurance broker

(45:49) Essential insurance coverages every investor needs

(48:55) Outro

Connect with Valerie Cusano:

• LinkedIn: https://www.linkedin.com/in/valerie-cusano-92290717/  
• Website: https://palm.global/canada/people 

—

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 on 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.

In this episode, Tait Duryea and Ryan Gibson dive into creative real estate financing with Chris Prefontaine, founder of Smart Real Estate Coach. Chris shares powerful strategies like seller financing, subject-to deals, and lease purchases, revealing how investors can acquire properties without banks—even in today’s high-interest rate environment. Learn how to find off-market properties, negotiate seller carrybacks, and unlock hidden real estate opportunities.

Chris Prefontaine is the chairman and founder of Smart Real Estate Coach, with over 30 years of experience in the real estate industry. Since 1991, he has built, brokered, and invested in properties across various asset classes. After weathering the 2008 financial crash, he shifted his focus to creative financing strategies, specializing in seller financing, lease purchases, and subject-to deals. Through Smart Real Estate Coach, Chris mentors investors across North America, helping them structure profitable real estate transactions without relying on banks. 

Show notes:

(0:00) Intro

(06:21) What is seller financing?

(10:26) Why sellers agree to carry the note—the hidden tax benefits

(19:41) Seller vs. buyer perspective

(24:19) How to find free-and-clear properties for seller financing

(38:02) The key to negotiating seller financing terms

(44:00) What is a Subject-To (Sub-To) deal?

(49:18) How to invest passively vs. actively in real estate

(52:29) Outro

Connect with Chris Prefontaine:

• LinkedIn: https://www.linkedin.com/in/chrisprefontaine 
• Website: https://wickedsmartbooks.com/PIP 

—

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

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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 on 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.

Have you ever wondered how you could write off an airplane? In this episode, Ryan DeMoor joins hosts Tait Duryea and Ryan Gibson to break down the tax benefits of aircraft ownership. Ryan shares how pilots and business owners can strategically use aircraft purchases for tax deductions, the IRS rules around business use, and why proper record-keeping is critical for audits. Whether you're considering buying a Cessna or a Gulfstream, this episode is packed with insights on bonus depreciation, IRS audits, 1031 exchanges, and passive vs. active use of an aircraft.

Ryan DeMoor is an aviation tax and finance expert specializing in corporate and private aircraft ownership structures. As the head of aviation tax at MySky, a Swiss-based aviation financial technology company, and the Chair of the NBAA Tax Committee, Ryan helps high-net-worth individuals and corporations navigate tax-efficient aircraft ownership, compliance, and financial structuring. A former pilot with over a decade of flying experience, Ryan brings a unique perspective on how aviators can strategically leverage aircraft for business use while staying compliant with IRS regulations.

Show notes:

(0:00) Intro

(06:04) How pilots can buy an airplane tax-efficiently

(08:35) Examples of using an aircraft for business

(13:29) IRS rules for business vs. personal aircraft use

(22:21) Why IRS audits on aircraft ownership are increasing

(28:08) The 25% business use rule and tax recapture risks

(30:42) 1031 exchanges for aircraft—what changed?

(38:40) Passive vs. active aircraft ownership and tax implications

(44:46) The most insane aircraft tax write-off ever

(49:08) Outro

Connect with Ryan DeMoor:

• LinkedIn: https://www.linkedin.com/in/ryan-demoor-cam-mba/details/experience/ 
• Website: https://mysky.com/ 
• Email: [email protected]
• NBAA (National Business Aviation Association): https://nbaa.org
• AOPA (Aircraft Owners and Pilots Association): https://www.aopa.org

—

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

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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 on 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.

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson explore the world of franchise ownership with franchise expert Cliff Nonnenmacher. Cliff brings decades of experience as a franchise consultant and serial entrepreneur, sharing insights into how pilots and professionals can invest in or operate franchises to build wealth. The discussion covers everything from initial franchise fees to evaluating opportunities, scaling businesses, and emerging non-brick-and-mortar trends. Whether you’re considering a side hustle or a full-time business, Cliff provides actionable advice tailored to high-income professionals seeking financial independence.

Cliff Nonnenmacher is a veteran entrepreneur and franchise consultant with over 20 years of experience in franchise ownership, business scaling, and investment strategies. A former investment banker, Cliff has managed multi-million-dollar ventures and specializes in helping professionals transition into franchise ownership. He provides guidance on selecting, funding, and operating franchises that align with personal goals, making him a trusted resource for aspiring business owners.

Show notes:

(0:00) Intro

(3:30) Meet Cliff Nonenmacher: Franchise expert

(9:25) History of franchising and its business models

(15:05) Breaking down franchise fees and royalties

(21:44) What makes a successful franchisee

(26:38) Cliff’s free consulting services explained

(32:40) Buying a franchise: Existing vs. new

(39:51) Non-brick-and-mortar franchise trends

(50:38) Surprising revenue potential of service-based franchises

(53:50) Outro

Connect with Cliff Nonnenmacher:

• LinkedIn: https://www.linkedin.com/in/cliffnonnenmacher 
• Website: http://www.franocity.com 
• Email: [email protected]
• Podcast: Pursuit of Profit (featuring franchise founders)- https://franocity.com/pursuit-of-profit-podcast/

—

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/ 

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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 on 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.