In this final podcast episode of 2024, Chris and John explore the "Taxpayer Timeline," equipping listeners with vital insights into the tax calendar year. They unravel the complexities of tax deadlines, clarifying essential dates for individuals and small business owners. As the year draws to a close, they ensure you're poised to enter 2025 with enhanced tax savvy. Sponsored by The Mortgage Shop, the episode extends gratitude to dedicated listeners and their community.

Navigating the tax timeline can be daunting, but this episode breaks down crucial dates like S Corporation and partnership deadlines on March 15, personal tax obligations on April 15, and estimated tax payments throughout the year. With expert insights, Chris demystifies the quarterly tax schedule, reducing the risk of missed deadlines and penalties. Their engaging discussion helps streamline tax planning, ensuring you never overlook important obligations.

Key Takeaways:

• The episode provides an in-depth walkthrough of the 2024 taxpayer timeline, highlighting pivotal tax dates for individuals and small business owners.
• Essential deadlines covered include S Corp and partnership returns due on March 15, personal tax filing on April 15, and quarterly estimated tax payments.
• The importance of adhering to IRS deadlines to avoid penalties, particularly for taxpayers with business interests, is a focal point.
• Listeners receive practical tips on organizing tax responsibilities with the help of technology like calendar reminders.
• The podcast pitches a service for finding tax professionals, showcasing the value of the Teaching Tax Flow community.

Notable Quotes:

1.  "There's so many dates going on in the tax preparation or tax world." – Chris Picciurro
2. "Your fourth quarter federal estimated tax payment from the year before is due on January 15th." – Chris Picciurro

Resources:

• IRS website for tax payments: IRS.gov
• Teaching Tax Flow community tax prep: www.2025.tax

Episode Sponsor:
The Mortgage Shop

• (00:01) - Reflecting on 2024 and Exploring the Taxpayer Timeline

In this festive edition of the Teaching Tax Flow podcast, episode 115 brings listeners intriguing insights into what can be considered 'gifts' from the IRS. Chris Picciurro and John Tripolsky delve into the intricacies of tax benefits that many taxpayers may overlook. These gifts, appropriate for taxpayers from various income brackets, serve as a crucial reminder of the opportunities within tax law to ease financial burdens, especially during the holiday season.

Throughout the episode, Chris highlights five significant tax code sections, including the 1031 Exchange, Health Savings Accounts, and the Augusta Rule, among others. Each section promises a myriad of advantages, urging the audience to capitalize on these provisions to manage capital gains, medical costs, and even property sales more effectively. With an engaging and informative tone, this episode is a treasure trove for anyone looking to deepen their understanding of beneficial yet lesser-known elements of the tax code.

Key Takeaways:

• 1031 Exchange: Enables taxpayers to defer capital gains taxes on real estate by reinvesting the proceeds into "like-kind" property, thereby enhancing investment potential.
• Health Savings Accounts (HSA): This triple tax-advantage tool offers deductions, tax-free growth, and tax-free withdrawals for qualified medical expenses.
• Section 121 Exclusion: Allows homeowners to exclude up to $500,000 in capital gains from the sale of a primary residence if specific criteria are met.
• Augusta Rule: Homeowners can rent their primary residence for up to 14 days tax-free, opening opportunities for additional income during high-demand events.
• Step-Up in Basis: Offers substantial tax savings by resetting the cost basis of an inherited asset to its fair market value at the time of the original owner’s death.

Notable Quotes:

1. “You get a deduction for putting the money in. The money grows tax-deferred, and it gets taken out in a qualified distribution, tax-free.” – Chris Picciurro
2. “The IRS doesn’t give us too many gifts, but I wanted to identify my five favorite gifts that the IRS gives us.” – Chris Picciurro
3. “This could be a great opportunity for you if you're in a situation where you're selling property and you don't need the cash.” – Chris Picciurro
4. “Remember, you’ve got to identify the replacement property within 45 days, and you’ve got to close within 180.” – Chris Picciurro
5. “If you inherit an asset, your cost basis in that asset is the fair market value of the asset the day you inherited it.” – Chris Picciurro

Ep. 73 | Understanding 'Step-Up in Basis' for Minimizing Taxes
https://share.transistor.fm/s/d62de4b2

Ep. 85 | 1031 Exchange Update
https://share.transistor.fm/s/4dcdb380

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

• (00:00) - Top Five IRS Gifts You Can Benefit From

In this episode of the Teaching Tax Flow podcast, hosts delve into the intricate relationship between student loans and taxes, a subject often misunderstood yet crucial. They explore the impact of student loans on financial planning and tax liabilities, dissecting significant elements such as the student loan interest deduction and loan forgiveness. The discussion is enriched by Chris Picciurro’s expert insights into strategies for managing student loans in conjunction with taxes.

Listeners will gain a comprehensive understanding of how student loan interest deductions work, emphasizing key points such as the distinction between above-the-line and itemized deductions. Chris provides critical analysis of the existing thresholds for income and their effects on deductibility for taxpayers. Moving into the second segment, the conversation pivots to student loan forgiveness, detailing changes brought by the American Rescue Plan Act and its implications for tax-free debt forgiveness. Finally, the episode introduces innovative updates from the Secure 2.0 Act on employer contributions toward student loans, opening up new avenues for employee benefits and financial planning.

Key Takeaways:

• The student loan interest deduction allows for a deduction of up to $2,500 annually, offering an above-the-line benefit but phasing out at certain income levels.
• The American Rescue Plan Act establishes temporary tax-free loan forgiveness from 2021 to 2025, significantly affecting individuals in forgiveness programs.
• Permanent exclusions allow certain professions, like public service workers and teachers, to benefit from tax-free forgiveness under specific conditions.
• The Secure 2.0 Act facilitates employer contributions to student loans in lieu of retirement fund contributions, promoting financial relief for employees.
• Careful planning around filing status could optimize student loan repayment strategies, aligning with income-based repayment and forgiveness goals.

Notable Quotes:

• "One of the rule changes was the forgiveness of student loan debt and the taxability of that." – Chris Picciurro
• "The IRS allows taxpayers to deduct up to $2,500 of interest paid on any qualifying student loan annually."
• "One of the reasons that you would file married separately has to do with student loan debt."
• "The American Rescue Plan Act of 2021 put a temporary exclusion for student loan debt forgiveness between the years of 2021 and 2025."
• "Employers now can contribute to student loan payments so instead of the employer funding a retirement plan contribution."

Resources:

• Teaching Tax Flow: Website
• Integrated Investment Group: Visit Website
• Defeating Taxes Facebook Group: Join Here

Episode Sponsor:
Integrated Investment Group

www.integratedig.com

• (00:03) - Exploring Student Loans, Taxes, and Financial Implications

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky delve into the intriguing topic of whether business owners should consider paying their spouses a salary. The episode explores the potential tax benefits and drawbacks associated with this strategy, aiming to provide clarity for entrepreneurs looking to optimize their tax situation. Sponsored by Reps Tracker, a real estate investment tax strategy tool, the podcast underscores the complexities and nuances of tax planning for small businesses.

Chris highlights three primary reasons why a business owner might decide to put their spouse on payroll: maximizing contributions to retirement plans, creating deductible benefits, and reducing self-employment tax. The discussion dives deep into these strategies, providing tangible examples and clarifying stipulations, such as ensuring the spouse performs legitimate work. The episode also covers instances where it might not be advantageous to pay a spouse, emphasizing administrative burdens and potential tax pitfalls.

Key Takeaways:

• Maximize Retirement Contributions: Paying a spouse can potentially double retirement savings through plans like solo 401(k)s, significantly enhancing tax-deferred savings options.
• Create Tax-Deductible Benefits: Employing a spouse can enable tax-deductible medical expenses and other fringe benefits through strategic plan implementation.
• Reduce Self-Employment Tax: Spousal compensation can help allocate income more favorably, potentially reducing overall self-employment tax liability.
• Administrative Burdens: Consider the cost of payroll processing and ensure the financial benefit outweighs administrative efforts and expenses.
• Legitimacy and Compliance: Emphasize ensuring legitimate employment to avoid audit risks and increased household taxes.

Notable Quotes:

• "Think about compensation planning as a really great tax planning tool." – Chris Picciurro
• "Your marginal tax rate is your number one key performance indicator when it comes to tax planning and strategy." – Chris Picciurro
• "Buying a vehicle, in my opinion, is not a tax strategy. It's a business decision that has an immediate tax benefit." – Chris Picciurro
• "If you are in a situation where you feel that you don't have any other employees and your spouse is helping in the business and you feel like you're paying a lot of expenses, that could be a benefit." – Chris Picciurro
• "The administrative burden might outweigh the benefit." – Chris Picciurro

Episode Sponsor:
REPStracker

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

Resources:

• Defeating Taxes Facebook Group: Access through defeatingtaxes.com

• (00:03) - Should You Pay Your Spouse in Your Business

About the Guests:

Alex Caswell is a seasoned wealth planner at RHS Financial with nearly seven years at the firm. He boasts a rich career in finance, having worked previously at Charles Schwab and Fidelity as a trading specialist and advisor. Alex has a personal connection to financial planning, being Latvian-born and having grown up in the U.S., where he developed a passion for helping others with their finances inspired by his mother's experiences. He specializes in comprehensive wealth management services tailored towards high net-worth individuals.

Colby Davis is the portfolio manager at RHS Financial, where he has been working since 2012. With a background in economics and finance, Colby handles day-to-day trading and rebalancing while focusing on maximizing tax efficiency and tax-loss harvesting strategies for clients. Originally from Seattle and now based in San Francisco, Colby negotiated his role at RHS Financial with a memorable elevator pitch and has been instrumental in their strategic financial approaches ever since.

Episode Summary:

In this episode of the Teaching Tax Flow podcast, host Chris Picciurro, alongside guests Alex Caswell and Colby Davis from RHS Financial, delve into advanced capital loss harvesting strategies. Beginning with the importance of tax planning as a year-round activity and transitioning into assessing capital gains and losses, this episode navigates the complexities of maximizing financial outcomes. As segments unfold, listeners gain insights into the intricate workings of these strategies and uncover ways to ethically reduce tax liabilities.

Through the discussion, Alex and Colby share seasoned perspectives on implementing tax-efficient investment tactics, emphasizing retail investors' need to offset capital gains. The conversation enriches understanding of capital loss harvesting—a practice aimed at mitigating tax obligations through strategic asset sales—and explores their proprietary long-short strategy named "Trend," promising increased tax efficiency. The episode weaves both foundational knowledge and innovative approaches, capturing the expertise necessary for effectively responding to high-value capital gain scenarios.

Key Takeaways:

• Tax Planning: Recognizing that tax planning is a proactive, year-round activity essential for effective financial management.
• Capital Gains and Losses: Understanding that capital gains can be offset by capital losses to reduce tax liabilities, with strategic considerations around realized and unrealized gains.
• Trend Strategy: Introducing RHS Financial's advanced Trend strategy, which maximizes tax-loss harvesting through long-short investing without increasing portfolio risk.
• Emotional Decision-Making: Highlighting the importance of removing emotion from investing decisions, especially when implementing strategies like capital loss harvesting.
• Flexibility in Tax Strategies: Emphasizing the crucial advantage of structuring tax strategies, like the Trend, in anticipation of future capital gains from life events or asset sales.

Notable Quotes:

1. "Your tax return is a verb, not a noun... the most time compression comes in the fourth quarter."
2. "We're always looking for different strategies to legally and ethically reduce the tax you pay in your lifetime."
3. "Without understanding how they can implement that [tax strategy], sometimes to their detriment, they decide to kind of hang out there."
4. "In a world where there's thousands of stocks and ETFs, it's easy to sell that and buy a new {similar} strategy."
5. "Real estate, stocks, digital assets...sale of any asset you own could potentially be a capital gain event."

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

• (00:03) - Advanced Strategies for Capital Loss Harvesting and Tax Planning

Episode Summary:

Join the Teaching Tax Flow podcast for episode 111 as Chris Picciurro and John Tripolsky explore one of the most commonly asked questions among entrepreneurs and small business owners: "Should I be an LLC?" 

In this episode, Chris breaks down the complexities of LLCs—single-member and multi-member—providing clarifications on tax implications, asset protection, and operating requirements. Whether you are a budding entrepreneur, a real estate investor, or someone looking to optimize your business structure, stay tuned for an insightful discussion.

LLCs, or Limited Liability Companies, offer various benefits and challenges for business owners. This episode delves into the myth that forming an LLC provides automatic tax benefits, explaining that in most cases, single-member LLCs do not offer tax advantages. Chris highlights the importance of choosing the right structure based on your specific business needs and potential liabilities. He also explores advanced considerations like being taxed as a corporation and the implications of multi-member LLCs, revealing the flexibility and administrative responsibilities involved.

Key Takeaways:

• Forming an LLC does not inherently provide tax benefits unless making additional tax elections, particularly for single-member LLCs.
• A key advantage of LLCs is liability protection, which can safeguard personal assets, though compliance must be maintained to avoid piercing the corporate veil.
• Multi-member LLCs provide flexibility in ownership structuring, allowing allocation of income, deductions, and credits beyond proportionate equity.
• Tax returns for multi-member LLCs can be complex and costly, highlighting the importance of weighing structure options.
• Consulting with a tax professional or attorney is vital prior to forming an LLC to ensure you select the most suitable business structure for your goals.

Notable Quotes:

1. "Forming an LLC does not provide additional tax deductions that didn't exist before."
2. "The advantage of a multi-member LLC is the flexibility in ownership and allocation of income."
3. "A single-member LLC is a disregarded entity for federal tax purposes."
4. "The operating agreement of an LLC is like its bylaws—integral and should be well-structured."
5. "Talk to an attorney or tax professional before forming an LLC or electing corporate tax status."

Resources:

• Defeating Taxes Private Facebook Group: DefeatingTaxes.com

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

Unlock the mysteries of business structuring and tax optimization by tuning in to this episode of the Teaching Tax Flow podcast. Chris provides invaluable insights and actionable strategies that can transform the way you view LLCs. Don't miss out on the chance to deepen your understanding and position yourself for success. Subscribe to the podcast and stay updated with our practical tax-saving tips in future episodes!

• (00:02) - Should I Be An LLC

About the Guest: Duke Alexander Moore

Duke is a leading tax professional and the founder of Duke Tax. With a robust background in accounting and tax services, Duke has carved a niche in the tax planning domain for influencers and content creators. Known for his dynamic presence on social media, particularly TikTok, where he has gathered an audience of over 3.5 million followers, Duke has been recognized for blending humor with education. His innovative approach to simplifying complex tax issues has earned him appearances on major platforms such as Good Morning America. Additionally, Duke is an enrolled agent and has a profound understanding of the unique financial challenges facing modern digital entrepreneurs.

Episode Summary:

In Episode 110 of the Teaching Tax Flow podcast, hosts John Tripolskyand Chris Piciurro dive into the intricacies of tax planning for influencers and content creators alongside the well-regarded Duke Alexander Moore. The episode spotlights the burgeoning industry of digital creators and the subsequent tax challenges they encounter. Duke, who boasts a remarkable following on TikTok, captivatingly brings a fresh perspective to tax guidance by infusing an element of entertainment into traditionally dry topics. This engaging installment illustrates the need for specialized tax services as online platforms become lucrative income sources.

Through conversations peppered with insightful exchanges and anecdotes, the episode navigates the complexities that content creators face in managing finances. Duke, an influencer and tax expert himself, shares his journey and how his firm, Duke Tax, is uniquely positioned to cater to the needs of creators, ranging from beginners to top-earning professionals. Among the main themes discussed are monetization strategies, the intricacies of tax compliance, and the importance of personalized tax planning. Listeners will gain actionable insights into managing their digital venture's financial health effectively.

Key Takeaways:

• Tax planning is crucial for content creators and influencers to avoid legal issues and maximize financial returns.
• Experience and specialization in the online creator niche are essential qualities to seek in a tax professional.
• Content creators must be strategic about their monetization methods, considering brand deals, subscriptions, and product sales.
• Educating clients about their financial obligations fosters better compliance and a sense of empowerment among digital entrepreneurs.
• Consistency in content creation paired with unique brand engagement is vital in maintaining and growing an audience.

Notable Quotes:

• "Taxes aren't fun, so I put an entertaining spin on it." – Duke Alexander Moore
• "Followers don't equal dollars." – Duke Alexander Moore
• "Get inspired and don't be afraid to mimic that person. Consistency is the most important thing." – Duke Alexander Moore
• "We are in the business of actually creating an experience." – Duke Alexander Moore
• "If you're not failing, you're not changing. You're not growing." – Duke Alexander Moore

Resource:

• Duke Tax: workwithduke.com

Episode Sponsor: The Mortgage Shop

Listeners are invited to explore the full episode to uncover detailed insights from Duke Moore on tax strategies tailored for influencers and to stay updated with future episodes of the Teaching Tax Flow podcast that continue to break down complex tax issues into actionable advice.

• (00:03) - Tax Planning Insights for Influencers and Content Creators

In this lively episode of the Teaching Tax Flow podcast, hosts John and Chris delve into the outcomes of the recent election, marking a notable shift with Donald Trump poised to return to the presidency. This episode serves as a third installment in their White House walkthrough series, carrying listeners through an engaging discussion on the implications of Trump's presidency concerning tax legislation, economic strategies, and potential changes to financial policies. With a blend of humor and insight, the hosts navigate through what these political shifts might mean for different stakeholders, from everyday American taxpayers to large business entities.

The conversation is particularly centered around the intricate proposals suggested by Trump, such as the extension of the Tax Cuts and Jobs Act and specific deductions. Chris unpacks some complex economic concepts, including bonus depreciation and the SALT tax deduction, underlining how these could affect both businesses and individual taxpayers. The episode also highlights the essential process of how tax proposals become law, providing listeners with a comprehensive understanding of legislative procedures in the tax domain. This episode is a valuable listen for anyone looking to stay informed on fiscal policies and the political shifts shaping them.

Key Takeaways:

• Election Outcomes: Donald Trump is set to return as president, prompting potential changes in tax policies and economic strategies.
• Tax Policy Changes: Discussions include extending the Tax Cuts and Jobs Act and 100% bonus depreciation, with implications for business taxation.
• Legislative Process: The episode outlines the route from proposal to law, vital for understanding how tax policies are decided and implemented.
• Taxation Nuances: Focus on deductions, including SALT and tax exemptions on various forms of income such as Social Security.
• Practical Insights: The podcast offers strategic tax planning insights, particularly beneficial for U.S. citizens in higher tax liability states.

Notable Quotes:

1. "So ultimately, the theme would be whatever we have right now would continue moving forward in general. And I've said many, many times that taxes right now are on sale." - Chris Picciurro
2. "We're just pontificating right now, but that's what this episode's about. Like, gosh, okay, we finally know where the heck we're at with this election and let's dive in and look at what's getting proposed." - Chris Picciurro
3. "Social Security started becoming taxable. And now for many, many people, up to 80, 85% of the Social Security benefits are taxable." - Chris Picciurro
4. "Bonus depreciation is the backbone of cost segregation studies for our real estate investors." - Chris Picciurro
5. "Ultimately [with SALT deductions], if you're paying a tax somewhere else, you should probably get a deduction for it. I mean, that seems fair." - Chris Picciurro

Resources:

• Defeating Taxes

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

• (00:05) - Election Results, Tax Plans, and Political Humor

In this episode of the Teaching Tax Flow podcast, co-hosts John Tripolsky and Chris Picciurro tackle a variety of tax-related questions in a rapid-fire format. They begin by highlighting the role of CPAs and EAs in tax preparation and planning, emphasizing the proactive approach to managing taxes. The episode provides listeners with practical insights into estate planning and tax optimization.

Throughout the episode, John and Chris delve into important tax topics such as common misconceptions about taxes, the significance of maintaining accurate financial records, and the benefits of being self-employed. They also discuss income shifting strategies like paying children legally for work done in a family business. The duo provides advice on hiring tax professionals and bookkeepers, ensuring listeners have the tools to nurture beneficial financial relationships. This episode is rich with actionable tips for both individual taxpayers and business owners, highlighting the importance of community and proactive tax management.

Key Takeaways:

• Proactive Tax Planning: CPAs and EAs can significantly impact tax outcomes through proactive strategy and planning, ensuring individuals and businesses pay the least tax legally and ethically.
• Common Misconception: A prevalent myth is that taxes are unmanageable, but through strategic actions, taxpayers can control their tax liabilities.
• Income Structuring: Shifting income to family members, like paying children, can optimize tax savings if done legally and with clear records.
• Accurate Record Management: Maintaining detailed financial records is essential for businesses to maximize deductions and ensure compliance in case of audits.
• Community Support: Being part of a community and utilizing resources like the Teaching Tax Flow group can enhance tax knowledge and confidence in financial decisions.

Notable Quotes:

1. "You control your tax by the actions that you take, or lack of actions." – Chris Picciurro
2. "Tax laws are written to encourage and discourage certain behavior." – Chris Picciurro
3. "A tax credit is better than a deduction 99% of the time." – Chris Picciurro
4. "It's essential for a business to keep accurate financial records." – Chris Picciurro
5. "The best time to have your tax return completed is any time before October 15th that legally and ethically gives you the best result." – Chris Picciurro

Resources:

• Teaching Tax Flow community on Facebook: DefeatingTaxes.com
• Teaching Tax Flow YouTube Channel with over 200 videos for tax tips and strategies.

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

Listeners are encouraged to tune in to the full episode for a deeper dive into these topics and stay updated with future discussions and insights shared on the Teaching Tax Flow podcast.

• (00:02) - Rapid Fire Tax Questions with Chris Pacquiao

About the Guest: Kelly Bender
Kelly is the President of TBS in Pittsburgh, Pennsylvania, and an accomplished tax professional with a motto of "life untaxed." She is recognized for her proactive approach to tax and accounting services and has significantly expanded her practice through strategic acquisitions. Kelly is an enrolled agent and holds the prestigious role of an instructor for the National Association of Tax Professionals. She has presented at various conferences, including the Taxposium, highlighting her expertise in accounting for family-owned businesses.

Episode Summary:

In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky engage in an enriching discussion with Kelly Bender, a seasoned tax professional, about the life cycle stages of a business. As businesses evolve from the startup phase through growth to transition, Kelly provides substantial insights into tax strategies, operational tips, and planning to ensure financial health and longevity.

During the conversation, Kelly emphasizes the importance of choosing the right entity structure from the outset and how those decisions should align with personal and long-term business goals. Navigating the growth phase, Kelly discusses strategies for operational delegation, particularly outsourcing bookkeeping functions, to allow for efficient scaling. Moreover, she sheds light on transition planning for business owners looking to exit or sell, advising them to start planning years ahead to maximize their business's value and ensure a smooth transition. Tune in for practical business advice that can guide you toward achieving robust financial health and success.

Key Takeaways:

• Always begin with choosing the proper entity structure that aligns with your business goals.
• In the growth phase, consider outsourcing your bookkeeping to focus on strategic business development.
• Transition planning should ideally start five years before you wish to exit, ensuring maximum value and smooth succession.
• Effective communication and humility in leadership are crucial, especially when steering family-owned businesses.
• Use personalized tax strategies tailored to your situation, incorporating personal and business goals for optimal outcomes.

Notable Quotes:

• "The only way we can multiply ourselves is by delegating things that are not where our primary brainpower is used best." – Kelly Bender
• "It's better to exit with a plan than to exit by accident." – Kelly Bender
• "As soon as you start to feel like you're not giving the bookkeeping enough attention, it's time to let go of the reins." – Kelly Bender.
• "The person who's netting $5,000 a year is a very different conversation than the person netting $50,000 a year." – Kelly Bender.
• "Simple is really better because you don't even know how to handle that yet." – Kelly Bender.

Demonstrating how different phases of business require varied approaches to tax and operational strategies, this episode is a must-listen for any business owner or aspiring entrepreneur looking for actionable advice. Keep following our podcast for more insightful discussions with industry experts!

Episode Sponsor:
Integrated Investment Group

www.integratedig.com

• (00:14) - Exploring Business Life Cycles and Investment Opportunities