
#42 - Real Estate Investing: Tax-Saving Strategies and Best Practices with Billy Withers
10/24/23 • 54 min
On this episode of Passive Income Pilots, Tait and Ryan interview Billy Withers. Billy Withers, EA, MT, is a financial expert and the owner of Summit Advanced Tax Strategy. He has helped hundreds of real estate investors and business owners organize their financial systems and reduce tax liabilities. With his expertise and the flexibility of a virtual firm, he provides prompt and effective service to ensure the growth and needs of his clients are met. Billy's experience in the field has made him an invaluable asset to those looking to maximize their profits while minimizing their tax liabilities. Billy talks about the intersection of taxes and real estate investments. He discusses optimizing tax situations, qualifying as a real estate professional, tracking deductions, and dealing with late filings. Billy emphasizes treating real estate investments as a business, gathering necessary documents, and working with a tax professional experienced in real estate matters to avoid problems and stay on top of taxes. Enjoy the show!
Timestamped Show Notes
(00:00) Intro
(04:08) Billy's career journey and specialization in real estate taxes
(05:52) The advantages of working with a tax strategist
(07:51) Tax efficiency: planning for taxable events in real estate
(11:31) What a tax strategist does
(13:25) Advisory service fee structure and getting started
(15:40) Quick hit opportunities, tax-advantaged strategies, and changes
(22:42) Qualifying as a real estate professional and hour requirements
(26:16) Keeping track of time spent as a real estate professional
(28:38) Collaboration between spouses to qualify as real estate professionals
(30:54) Caution against taking risks with material participation claims
(32:04) Structuring LLCs for earned and passive income
(34:13) Importance of tracking expenses and using dedicated accounts for real estate
(40:45) The complexity and individuality of tax matters in real estate
(43:57) Concerns about extending tax returns and K-1 forms
(52:46) What is an enrolled agent
(54:30) Outro
Resources Mentioned
#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
---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!
Join our growing community on Facebook
Check us out on Instagram @PassiveIncomePilots
Follow us on X @IncomePilots
Get our updates on LinkedIn
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. The hosts, Tait Duryea and Ryan Gibson, do not necessarily endorse the views of the guests featured on the podcast, nor have the guests been comprehensively vetted by the hosts. Under no circumstances sh...
On this episode of Passive Income Pilots, Tait and Ryan interview Billy Withers. Billy Withers, EA, MT, is a financial expert and the owner of Summit Advanced Tax Strategy. He has helped hundreds of real estate investors and business owners organize their financial systems and reduce tax liabilities. With his expertise and the flexibility of a virtual firm, he provides prompt and effective service to ensure the growth and needs of his clients are met. Billy's experience in the field has made him an invaluable asset to those looking to maximize their profits while minimizing their tax liabilities. Billy talks about the intersection of taxes and real estate investments. He discusses optimizing tax situations, qualifying as a real estate professional, tracking deductions, and dealing with late filings. Billy emphasizes treating real estate investments as a business, gathering necessary documents, and working with a tax professional experienced in real estate matters to avoid problems and stay on top of taxes. Enjoy the show!
Timestamped Show Notes
(00:00) Intro
(04:08) Billy's career journey and specialization in real estate taxes
(05:52) The advantages of working with a tax strategist
(07:51) Tax efficiency: planning for taxable events in real estate
(11:31) What a tax strategist does
(13:25) Advisory service fee structure and getting started
(15:40) Quick hit opportunities, tax-advantaged strategies, and changes
(22:42) Qualifying as a real estate professional and hour requirements
(26:16) Keeping track of time spent as a real estate professional
(28:38) Collaboration between spouses to qualify as real estate professionals
(30:54) Caution against taking risks with material participation claims
(32:04) Structuring LLCs for earned and passive income
(34:13) Importance of tracking expenses and using dedicated accounts for real estate
(40:45) The complexity and individuality of tax matters in real estate
(43:57) Concerns about extending tax returns and K-1 forms
(52:46) What is an enrolled agent
(54:30) Outro
Resources Mentioned
#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
---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!
Join our growing community on Facebook
Check us out on Instagram @PassiveIncomePilots
Follow us on X @IncomePilots
Get our updates on LinkedIn
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. The hosts, Tait Duryea and Ryan Gibson, do not necessarily endorse the views of the guests featured on the podcast, nor have the guests been comprehensively vetted by the hosts. Under no circumstances sh...
Previous Episode

#41 - Short-Term Rental Strategies To Maximize Your Passive Income with Dan Templin
On this episode of Passive Income Pilots, Tait and Ryan interview Dan Templin. Dan Templin is a real estate investor and coach in addition to being the owner of different small businesses. He manages real estate investments from top to bottom for his busy clients. Dan possesses an unwavering dedication to assisting investors in successfully establishing and operating their first Airbnb venture. Dan shares his journey into the short-term rental industry. He discusses his experience with rental arbitrage, building relationships with landlords, and the potential of short-term rentals. Dan also provides software recommendations and insights on managing rental units and automating the processes. He dives into these strategies and their impact on a successful short-term rental business. Enjoy the show!
Timestamped Show Notes
(00:00) Intro
(02:53) Flipping houses and owning a bar
(04:38) Profitability of short-term rentals (SRT) and learning from online courses
(07:28) Furnishing and equipping short-term rentals
(09:05) Potential lease violations and building a good landlord relationship
(12:18) Market for short-term rentals beyond vacation rentals
(15:03) AirDNA and Price Labs: Tools for pricing and market analysis
(17:58) How to increase occupancy on SRTs
(22:32) The challenges and benefits of direct booking
(26:17) Streamlining guest communications with Hospitable
(29:11) Ensuring guest safety with automated locks and security cameras
(36:04) Cost-segregation
(37:38) Building a team for property management
(39:48) Writing booklets for business improvement
(41:59) Automating and delegating tasks for efficiency
(44:30) Setting rental duration based on property and market type
(46:53) How to find out more about Dan
(47:00) Outro
Resources Mentioned
#14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis
---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!
Join our growing community on Facebook
Check us out on Instagram @PassiveIncomePilots
Follow us on X @IncomePilots
Get our updates on LinkedIn
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. The hosts, Tait Duryea and Ryan Gibson, do not necessarily endorse the views of the guests featured on the podcast, nor have the guests been comprehensively vetted by the hosts. Under no circumstances should any material presented in this podcast be used or considered as an offer to sell, or a solicitation of any offer to buy, an interest in any investment. Any potential offer or solicitation will be made exclusively through a Confidential Private Offering Memorandum related to the specific investment. Access to detailed information about the investments discussed is restricted to individuals who qualify as accredited investors under the Securities Act of 1933, as amended.
Next Episode

#43 - Exploring the Boom of Self-Storage and Its Investment Potential
Welcome back to another episode! Tait and Ryan talk about the lucrative world of commercial real estate investments, with a special focus on self-storage, a rising asset class rapidly gaining traction among investors. They discuss cap rates, why building is better than buying in the current market, underwriting self-storage, and rent growth. Enjoy the show!
Timestamped Show Notes
(00:00) Intro
(03:34) What is a cap rate, and why does it matter
(07:26) Real estate vs. stocks
(08:54) Why invest in a ground-up development project
(10:44) Why building is better than buying in the current market
(12:47) Renters vs. buyers of self-storage
(16:51) Market research before building self-storage
(19:19) Why everybody wants storage
(21:17) Why did Spartan Investor choose self-storage
(26:18) Underwriting self-storage and rent growth
(30:26) Challenges and opportunities in commercial real estate investments
(36:15) Risks in ground-up development
(39:19) Investment opportunities
(43:24) Outro
---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!
Join our growing community on Facebook
Check us out on Instagram @PassiveIncomePilots
Follow us on X @IncomePilots
Get our updates on LinkedIn
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. The hosts, Tait Duryea and Ryan Gibson, do not necessarily endorse the views of the guests featured on the podcast, nor have the guests been comprehensively vetted by the hosts. Under no circumstances should any material presented in this podcast be used or considered as an offer to sell, or a solicitation of any offer to buy, an interest in any investment. Any potential offer or solicitation will be made exclusively through a Confidential Private Offering Memorandum related to the specific investment. Access to detailed information about the investments discussed is restricted to individuals who qualify as accredited investors under the Securities Act of 1933, as amended. Listeners are responsible for their own investment decisions and are encouraged to seek professional advice before investing.
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