About the Guest: Caden Gunnell
Caden is a Junior Partner at Strategic Associates, where he specializes in proactive tax planning and solution implementation for high-income earners, real estate investors, and successful entrepreneurs. With a background in business strategies and tax planning, Caden has been instrumental in connecting clients with innovative tax-saving solutions, such as leveraged charitable giving. His expertise ensures clients are well-positioned to maximize their tax benefits while contributing to worthy causes.

Episode Summary:

Welcome to episode 101 of the Teaching TaxFlow podcast where hosts John and Chris dive deep into the world of leveraged charitable giving with expert guest Caden Gunnell from Strategic Associates. This episode uncovers how leveraging charitable donations can significantly enhance tax deductions for high-income earners, making it a must-listen for anyone looking to optimize their tax strategies.

Leveraged charitable giving is a powerful tool for individuals, especially those with high W-2 incomes, to increase their tax efficiency and charitable impact.

Throughout the episode, Caden explains how individuals can turn a simple donation into a multi-fold tax deduction through strategic planning. Chris and Caden delve into the mechanics of this tax strategy, its benefits, the documentation required, and the types of clients who can benefit most from it. They emphasize the importance of having substantiation to avoid IRS scrutiny and explore how this strategy can fit into a broader tax optimization plan.

Key Takeaways:

• Leveraged Charitable Giving: This strategy involves using a certain amount of cash to create a larger donation value, effectively multiplying the tax deduction.
• Documentation and Compliance: Proper substantiation through official appraisals and gift receipts is critical to ensure compliance and maximize tax benefits.
• Eligibility and Benefits: Best suited for individuals with taxable incomes of $250,000 or more, this strategy is highly beneficial for those with a charitable inclination.
• Yearly Flexibility: Unlike some long-term commitments, leveraged charitable giving can be assessed and implemented on a year-by-year basis.
• Stacking Strategies: Leveraged charitable giving can be combined with other tax strategies to further reduce taxable income, especially for business owners.

Notable Quotes:

1. "We're taking a certain dollar amount and creating a one to three, one to four, and sometimes as high as one to five donation." — Caden Gunnell
2. "This isn't being done just to help someone save money in taxes. Anytime we're doing anything to save money in taxes, if that's our only goal, we're probably not doing the right things." — Caden Gunnell
3. "Your tax insurance return shouldn't be a sprint; it should be a half marathon and something you think about all year round." — Chris Picciurro
4. "The IR's is getting extremely more sophisticated and they are using AI and they are using technology to find anomalies." — Chris Picciurro

Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23

Hear more about how you can leverage your charitable donations to maximize your tax deductions by tuning into the full episode. Stay tuned for more insightful tips and strategies on the Teaching TaxFlow podcast!

• (00:03) - Leveraged Charitable Giving and Tax Strategies for high-earners
• (06:36) - Leveraging Charitable Giving for Maximized Tax Deductions
• (13:50) - Understanding Tax Strategies and Their Impact on Individuals
• (16:42) - Leveraged Charitable Giving Strategies for High-Income Earners
• (24:37) - Teaching Tax Flow Podcast: Insights and Resources

Welcome to the 100th episode of the Teaching Tax Flow podcast!

(we've gone visual - watch this full episode on our YouTube channel)

In this milestone episode, hosts John Tripolsky and Chris Picciurro celebrate their journey from humble beginnings to becoming a top-tier resource in tax planning and strategy. They reflect on the podcast's inception—starting with a microphone perched on a pizza box—and the evolution of their content, community, and reach. The hosts express gratitude to their loyal listeners, engaging guests, and supportive sponsors, while also unveiling exciting changes ahead, including YouTube integration and expanded free educational resources.

As the podcast grew from its initial focus on real estate market spotlights to a broader tax planning scope, John and Chris discuss key milestones and listener engagement. They underscore the importance of building a community to drive content and share real-world applications of tax strategies. Looking ahead, the hosts emphasize their commitment to delivering premium, accessible tax education for individuals and professionals alike, solidifying their standing as the voice of tax planning.

Key Takeaways:

• Origin Story: The podcast began with a microphone clipped to a pizza box, highlighting the hosts' DIY spirit and commitment to just getting started.
• Community-Driven Content: Listener feedback and community engagement on platforms like the Defeating Taxes Facebook group have been crucial in shaping podcast topics.
• Educational Pivot: The podcast content has shifted from a specific real estate focus to a broader, holistic approach to tax planning and strategy.
• YouTube Expansion: All podcast episodes and comprehensive educational content will now be available on YouTube, increasing accessibility and reach.
• Gratitude and Evolution: John and Chris express gratitude towards all guests, listeners, and sponsors, promising continued evolution and more interactive, valuable content.

Notable Quotes:

• "There's never a better time than now." - Chris
• "We are one of the top 10% of podcasts as far as longevity, and that's an accomplishment right there." - John
• "Our community drives our content, and that community has different pillars." - Chris
• "Teaching Tax Flow is not just a podcast; it's the voice of tax planning." - John
• "It's amazing how a community can sharpen itself and drive the direction of a podcast." - Chris

Resources:

• Teaching Tax Flow YouTube Channel: YouTube
• Defeating Taxes Facebook Group: Facebook
• The Mortgage Shop: Website

Original Music Credits (Intro): Christian Picciurro

Episode Sponsor: The Mortgage Shop

This episode is a testament to the power of community-driven content and the journey from modest beginnings to influential platforms. Join John and Chris as they continue to demystify tax planning and provide practical, enlightening discussions.

Stay tuned for more engaging content and educational resources from the Teaching Tax Flow podcast!

• (00:02) - Celebrating 100 Episodes of Teaching Tax Flow
• (04:16) - The Origin Story of a Podcast Launched on a Pizza Box
• (07:18) - Evolution of a Tax Planning Podcast Driven by Community Engagement
• (12:42) - A Confession from John (he's a fan of...)
• (14:15) - The Evolution of Tax Planning and Podcasting
• (19:09) - The Voice of Tax Planning
• (29:45) - Celebrating Episode 100 with New Changes and Future Plans

About the Guest: Angelina Urquhart
Angelina Urquhart is a compliance expert with Corpnet, a company specializing in business compliance and filing services. With a wealth of knowledge in entity formation and regulatory compliance, Angelina has been instrumental in helping businesses stay compliant with complex state and federal regulations. Her expertise includes navigating the Corporate Transparency Act and beneficial ownership information reporting requirements.

Episode Summary:

In this milestone episode, number 99, Chris Picciurro and John Tripolsky delve into the critical specifics of the Corporate Transparency Act (CTA) and Beneficial Ownership Information Reporting (BOI). Our special guest, Angelina Urquhart from Corpnet, shares her comprehensive insights and explains the new regulatory requirements that affect the majority of business entities.

The Corporate Transparency Act, aimed at curbing financial crimes such as money laundering and terrorism financing, imposes stringent reporting obligations on entities in the United States. Angelina highlights which entities need to comply, what details must be reported, and the profound implications of non-compliance. Throughout the episode, the discussion touches on the practicality of these regulations, the importance of timely filing, and the potential penalties for failure to adhere to the guidelines.

Key Takeaways:

• CTA and BOI Overview: Angelina breaks down the purpose of the Corporate Transparency Act and the Beneficial Ownership Information Reporting requirements.
• Entities Required to File: Most LLCs, corporations, and other registered entities must comply unless specific exemptions apply.
• Critical Deadlines: For new entities created in 2024, there is a 90-day compliance window. Entities formed before 2024 must file by December 31, 2024.
• Penalties for Non-Compliance: Significant civil and criminal penalties exist for failing to meet the reporting requirements.
• Practical Advice: Tips on using passports for ID verification and tracking changes to ensure ongoing compliance.

Notable Quotes:

1. Angelina Urquhart: "The days of you creating an LLC and having it owned by another LLC are still there, but you still have to now indicate who is benefiting from the operations of that entity."
2. Angelina Urquhart: "Something as easy as a driver's license expiring or you move...if you move, there's a filing requirement."
3. Chris Picciurro: "The penalties for not conforming to this are significant."
4. Angelina Urquhart: "This isn't going away, it's a safety belt from financial crimes."

Get started today on being compliant!

1. Visit www.teachingtaxflow.com/entity and hover over "Run a Business" in the header menu
2. Click on "Compliance Service"
3. Select "BOI Reporting"
4. Use the discount code "TTF" at checkout for a 5% discount.

Have more questions on BIO?
Schedule a discussion with our guest, Angelina.
BOOK NOW

Episode Sponsor:
Integrated Investment Group

www.integratedig.com

• (00:04) - Exciting Insights on Accredited Investors and Financial Success
• (02:59) - Understanding the Corporate Transparency Act and Beneficial Ownership Reporting
• (13:02) - Navigating Business Ownership Changes and Compliance Requirements
• (19:09) - The Evolution of Seatbelt Use and Safety Regulations
• (20:32) - Compliance Deadlines and Penalties for New Business Entities
• (23:46) - Navigating Business Compliance and Avoiding Financial Pitfalls

Welcome to Episode 98 of the Teaching Tax Flow podcast! In this episode, hosts Chris Picciurro and John Tripolsky delve into the often-overlooked pitfalls in tax planning, aptly referred to as the "Top Three Tax Landmines." They aim to educate real estate investors and other listeners on how to navigate the treacherous waters of tax obligations.

The discussion starts with Chris elaborating on depreciation recapture — the sudden surge in taxable income when you sell an asset you've previously claimed depreciation on. This intricate tax rule can catch you off guard if you are not prepared, especially in scenarios involving vehicles and real estate investments. Next, they explore phantom income, income that appears on your tax returns without actual cash realization. Often emerging from scenarios like cancellation of debt, partnership income, and barter transactions, phantom income can unexpectedly inflate your tax liability. Lastly, they examine the hazards of under-withholding taxes, particularly when experiencing significant life changes like job transitions or marital status modifications, which can cause a shortfall in tax payments.

Their conversation is enriched with tangible examples and actionable advice, highlighting the critical importance of tax planning. Chris and John delve into how a strategic approach to taxes can save you from unexpected financial burdens. For those looking to stay proactive with their taxes, this episode is a treasure trove of insights.

Key Takeaways:

• Depreciation Recapture: When selling an asset for which you've claimed depreciation, you may need to include some of the previously deducted amounts as taxable income. This often surprises sellers who do not receive any cash but owe taxes on the gain.
• Phantom Income: Income that appears on paper but does not provide actual cash, such as cancellation of debt, partnership income, or barter transactions, can lead to significant tax liabilities.
• Under-Withholding Risks: Life changes such as job transitions, marital status changes, or adjustments in income can lead to under-withholding of taxes, resulting in an unexpected tax bill at year-end.
• 10% Penalty for Early Retirement Distributions: Taking early distributions from a retirement account before age 59½ without qualifying for an exception can result in a 10% penalty in addition to regular tax liabilities.
• 401(k) Loan Pitfalls: If you leave your job, an outstanding 401(k) loan can become due immediately, creating taxable income and potentially subjecting you to a 10% penalty if not repaid promptly.

Notable Quotes:

1. "Tax flow does not equal cash flow." - Chris Picciurro
2. "Depreciation recapture can be a phantom income — no cash in your hands, but you owe tax." - Chris Picciurro
3. "Ignorance is not bliss when it comes to taxes. Ignorance is expensive." - John Tripolsky
4. "Just because taxes are withheld doesn't mean it's enough to pay what you owe." - Chris Picciurro
5. "With tax planning, you're not just preparing for the year-end. You're setting yourself up for a lifetime of tax efficiency." - John Tripolsky

Episode Sponsor:
REPStracker

www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)

• (00:04) - Top Three Tax Landmines and How to Avoid Them
• (07:25) - Depreciation Recapture Pitfalls in Vehicle and Real Estate Transactions
• (12:32) - Tax Pitfalls, Atari Memories, and Italian Family Traditions
• (14:39) - Understanding Phantom Income and Its Tax Implications
• (19:53) - Tax Planning, Phantom Incomes, and Business Advice
• (21:12) - Common Tax Landmines and How to Avoid Them
• (27:29) - The Importance and Benefits of Tax Planning

In Episode 97 of the Teaching Tax Flow podcast, hosts Chris and John delve into a powerful tax strategy, explaining how to income shift to family members or children. With the countdown to the 100th episode underway, this topic is timely and significant for business owners looking to control their tax liabilities. Chris and John unravel the intricacies of legally and ethically leveraging family members to optimize tax obligations, emphasizing that this strategy is not to be taken lightly or implemented illicitly.

Throughout the episode, Chris and John explore the benefits and implementation process of paying children for legitimate work in your business. By shifting income to lower tax brackets, parents can significantly reduce their overall tax burden. The discussion covers the importance of proper documentation, legitimate job roles, the advantages of different business structures, and the potential for utilizing earned income for additional benefits like Roth IRA contributions. Real-world examples make this episode a practical guide for those eager to harness this tax-saving strategy.

Key Takeaways:

• Legitimate Employment: Children must perform bona fide work suitable for their age and capabilities to be paid.
• Reasonable Compensation: Compensation must align with the nature of the work performed, avoiding any excessive payments that could raise red flags.
• Proper Documentation: Maintain thorough records similar to those for any other employee, including timesheets, task records, and payroll tax filings.
• Tax Benefits: Income shifted to children often incurs a lower tax rate or becomes tax-free, and specific conditions eliminate Social Security and Medicare taxes.
• Roth IRA Contributions: Children’s earned income allows for contributions to a Roth IRA, promoting long-term, tax-free growth of their earnings.

Notable Quotes:

• "The first benefit of paying kids is shifting the income to a lower marginal tax rate within the family." - Chris Picciurro
• "If you want to be a duck, you got to walk like one and quack like one." - Chris Picciurro
• "Ideas are cheap and implementation is valuable." - Chris Picciurro
• "Highest and best use...identifying what you're good at and sticking to it." - John Tripolsky

Episode Sponsor
Sunsets & Dinks
www.teachingtaxflow.com/pickleball
CODE: TTF15

• (00:04) - Income Shifting to Family Members for Tax Benefits
• (06:40) - Benefits and Legalities of Income Shifting by Paying Children
• (09:58) - Legal Tax Strategies Versus Risky Cheat Codes
• (10:49) - Tax Benefits and Legalities of Paying Your Children
• (19:21) - Tax-Free Growth Strategies for Teenagers
• (21:45) - Legitimate Ways to Save Money by Employing Your Children

On this episode of the Teaching Tax Flow podcast, we jump into the intricacies of "Hobby Loss Rules." Aimed at demystifying the often confusing threshold between hobbies and businesses, the hosts break down how the IRS defines and treats these activities differently for tax purposes. The discussion is particularly timely given the changes brought about by the Tax Cuts and Jobs Act of 2017, which altered how hobby expenses are deducted.

Throughout the episode, Chris and John explain the nine-factor test the IRS uses to determine whether an activity is a hobby or a business. They illustrate these points with relatable examples, such as the potential tax implications of John's "passion" for knitting and dog breeding. The hosts also stress the importance of maintaining detailed records and having a clear profit motive to ensure an activity is classified as a business, thereby allowing for the deduction of legitimate expenses on your tax return.

Key Takeaways:

• IRS Hobby vs. Business: Understand the IRS's nine-factor test to determine if an activity is a hobby or a business.
• Tax Reporting: Recognize how to report income and expenses from hobby activities versus business activities.
• Impact of Tax Cuts and Jobs Act: Learn how changes from the 2017 Tax Cuts and Jobs Act affected the deduction of hobby expenses.
• Practical Examples: Real-world scenarios provided to illustrate what counts as a hobby and what qualifies as a business.
• Next Steps: Practical advice on maintaining proper records and showing profit motives to ensure your activity is seen as a business.

Notable Quotes:

1. "The main issue is whether an activity is a hobby or business in the eyes of the IRS."
2. "Profit motive is crucial; hobbies typically have little effort to acquire the necessary expertise to consult a professional."
3. "For an expense to be deductible in your tax return for a business, the expense has to be ordinary and necessary."
4. "Under the Tax Cuts and Jobs Act of 2017, hobby expenses are no longer deductible, making it crucial to ensure your activity is classified correctly."
5. "The IRS provides a safe harbor guideline, known as the three out of five-year rule, which presumes profit motive if an activity generates profit in three out of five consecutive years."

Episode Sponsor:
The Mortgage Shop

• (00:04) - Understanding Hobby Loss Rules to Minimize Lifetime Taxes
• (02:58) - Hobby Versus Business: Tax Reporting and Rule Changes
• (05:18) - Discussing Hobbies, Movies, and Financial Losses from Knitting
• (07:13) - Determining If an Activity Is a Hobby or Business
• (11:18) - Hobby vs. Business: The Gray Area of Tax Deductions
• (12:27) - Determining Business vs. Hobby for Tax Purposes
• (15:07) - Tax Implications of Hobby vs Business Income
• (18:53) - Hobby Income Reporting and 1099K Changes
• (19:55) - Business vs. Hobby: Tax Implications for Dog Breeding
• (22:06) - Listener Appreciation and Engagement in the Defeating Taxes Podcast
• (24:18) - Educational Investment and Tax Advice Disclaimer

About the Guest:

Todd Jackson: Todd Jackson is a highly experienced tax attorney, M&A advisor, and real estate attorney based in Franklin, Tennessee. Known for his expertise in Deferred Sales Trusts (DSTs), 1031 exchanges, and complex tax planning strategies, Todd has worked closely with clients to help them minimize tax liabilities on large capital gains. He is also a licensed real estate agent and title insurance agent, showcasing his diverse skill set in the financial and legal sectors.

Episode Summary:

In this episode of the Teaching Tax Flow podcast, hosts John and Chris are joined by special guest Todd Jackson to explore the intricacies of Deferred Sales Trusts (DSTs). As Episode 95 counts down to their milestone 100th episode, the team delves into how DSTs can empower and educate high-income earners, real estate investors, and successful entrepreneurs to legally and ethically minimize taxes paid over their lifetime.

Todd Jackson provides a thorough comparison between DSTs and 1031 exchanges, highlighting the flexibility and control DSTs offer in deferring capital gains. This episode demystifies the concept of installment sales and explains how DSTs can alleviate some of the stringent requirements of 1031 exchanges, such as debt replacement and time constraints. With practical examples and insightful explanations, Todd emphasizes the significant tax planning benefits DSTs provide.

Key Takeaways:

• A Deferred Sales Trust (DST) is a powerful tool for deferring capital gains taxes using installment sale treatment.
• DSTs provide more flexibility and fewer restrictions compared to 1031 exchanges, particularly regarding replacement debt and investment options.
• It's essential to have the DST structure in place before any sale occurs to avoid triggering taxable events.
• The minimum capital gain for considering a DST is generally around $500,000 to justify the structure's complexity and cost.
• Timing and control are critical components of a DST, allowing the deferral of income recognition over several years while preserving and growing the trust's assets.

Notable Quotes:

1. "My phone usually rings when somebody's selling something and facing a capital gain." - Todd Jackson
2. "Would you rather pay something today or ten years from now? Most people are going to say they'd prefer to pay it later." - Todd Jackson
3. "We have to create this and maintain it in a way that prevents you from having a constructive receipt to where that triggers all the gains." - Todd Jackson
4. "The relationship between the trust and you as the seller is that of an installment sale, which is borrower and lender." - Todd Jackson
5. "DSTs can invest in anything. The conversation is more about what it should invest in, based on risk tolerance and preservation strategy." - Todd Jackson

Resources:

• Todd Jackson Law: Website

Join us next week for another insightful episode of the Teaching Tax Flow podcast, where we continue to bring you expert advice and actionable strategies to optimize your tax planning. Don't miss the countdown to our 100th episode!

Stay tuned and keep following us on Facebook, Twitter, and LinkedIn for more updates and exclusive content.

Episode Sponsor:
Strategic Associates, LLC
Roger Roundy
www.linkedin.com/in/roger-roundy-86887b23

• (00:04) - Deferred Sales Trusts and Year-End Tax Planning Strategies
• (04:55) - Deferring Capital Gains Taxes Through Installment Sales
• (09:56) - Choosing Flight Times and Recognizing Income
• (10:49) - Comparing 1031 Exchanges and Deferred Sales Trusts
• (16:20) - Deferring Capital Gains Through Installment Sales and Trusts
• (21:25) - Deferred Sales Trusts for Large Capital Gains
• (26:00) - Fun Questions and Career Insights with Todd Jackson

In this episode of the Teaching Tax Flow podcast, hosts Chris and John dive deep into the fascinating intersection of Olympic athletes and taxation. As the Olympic Games captivate viewers worldwide, this episode shifts focus to an often overlooked aspect of an athlete's journey – the tax implications of winning medals and earning prize money.

The episode begins with Chris shedding light on the monetary rewards that athletes receive from the United States Olympic Committee (USOC) and introduces the Olympians and Paralympians Act of 2016, which exempts certain athletes from federal income taxes on the value of their medals and prize money. John and Chris discuss the complex layers of taxation that athletes, especially Olympians, might face, including foreign income taxes and the practicalities of tax planning. They also reflect on their recent experience at the Taxposium in Orlando, highlighting key themes like the importance of technology and continuous education in modern tax practices.

Key Takeaways:

• Olympic Prize Money: Olympic athletes receive significant prize money from the USOC – $37,500 for a gold medal, $22,500 for silver, and $15,000 for bronze.
• Tax on Medals and Prize Money: Both the monetary winnings and the value of the Olympic medals are considered taxable income. However, under the Olympians and Paralympians Act of 2016, athletes with an adjusted gross income under $1 million ($500,000 if married filing separately) are exempted from federal taxes on these earnings.
• Foreign Tax Considerations: Athletes earning income in foreign countries may be subject to those countries' taxes but may receive a foreign tax credit in the US to avoid double taxation.
• Ordinary and Necessary Deductions: Olympians, considered self-employed, can deduct ordinary and necessary business expenses related to their athletic training and competitions, such as travel, coaching, and equipment.
• Professional Insights: The episode emphasizes the importance of specialized tax knowledge and ongoing education, drawing insights from the recent Taxposium conference attended by the hosts.

Notable Quotes:

1. "Olympians receive prize money from the USOC for winning medals – $37,500 for gold, $22,500 for silver, and $15,000 for bronze." – Chris
2. "The value of the Olympic medal is considered taxable income, along with the prize money." – Chris
3. "Under the Olympians and Paralympians Act of 2016, your medal prize money can be exempt from federal income taxes if your AGI is under a certain threshold." – Chris
4. "It's really neat to see how much emphasis is being placed on technology and modernizing the profession at these tax conferences." – John
5. "Ideas are cheap and implementation is valuable; that's why tax planning is so crucial." – Chris

Resources:

• Teaching Tax Flow
• Olympians and Paralympians Act of 2016
• Defeating Taxes Community
• National Association of Tax Professionals (NATP)

Episode Sponsor:
Legacy Lock (www.teachingtaxflow.com/legacy)
DISCOUNT CODE: Magic1495

• (00:04) - Olympic Athletes and the Impact of Taxes
• (02:44) - Taxposium: The Super Bowl of Tax Conferences
• (10:23) - Tax Implications for Olympians and Their Prize Money
• (13:16) - Tax Implications for Olympians Winning Medals and Prize Money
• (15:41) - Employment Status of Professional Athletes in Team Sports
• (17:09) - Tax Planning Strategies for Olympians' Prize Money
• (19:16) - Navigating Double Taxation for US Residents Earning Foreign Income
• (21:06) - Tax Implications for Olympians as Independent Contractors
• (23:12) - Tax Implications and Value of Olympic Medals
• (26:41) - Understanding Complex Tax Codes and IRS Efforts