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 hig...
Dec 24, 2024•29 min
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...
Dec 17, 2024•22 min
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 o...
Dec 10, 2024•26 min
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 manage...
Dec 03, 2024•29 min
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 optimiz...
Nov 26, 2024•38 min
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 ...
Nov 19, 2024•38 min
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 ...
Nov 12, 2024•36 min
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 ab...
Nov 05, 2024•33 min
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 Taxposiu...
Oct 29, 2024•30 min
Episode Summary: In this insightful episode of the Teaching Tax Flow podcast, hosts delve into the tax proposals of former President Donald Trump, as part of their White House Walkthrough series. With input from tax expert Chris Picciurro, the episode breaks down Trump's proposed reforms, comparing them to both current policy and Vice President Harris's outlined plans. It offers a deep dive into potential impacts on business taxes, capital gains, deductions, and the estate tax, providing listene...
Oct 22, 2024•33 min
In this episode of the Teaching Tax Flow podcast, hosts John and Chris delve into the politically charged waters of taxation as part of their White House Walkthroughs series, covering proposed tax changes by current candidates. The focus for this episode is Vice President Kamala Harris's tax proposals, analyzed strictly from a factual perspective using reliable resources like the Tax Foundation. Chris Picciurro outlines the potential impacts on both corporate and individual taxation, navigating ...
Oct 15, 2024•34 min
About the Guest: Chrissy Siders Chrissy is a seasoned professional in the credit union industry, having begun her career in 1998. A degree holder from Michigan State University, Chrissy has developed a deep understanding of the financial industry through her extensive work in compliance, fraud, security, and internal audit. Since 2017, she has served as the President and CEO of True Community Credit Union, headquartered in Jackson, Michigan. Under her leadership, the credit union has expanded si...
Oct 08, 2024•35 min
About the Guest: Alec Hutchin Alec is the Vice President of Investments for MDS Energy Development, LLC. He holds a degree in economics and has a deep-rooted passion for the natural gas industry, having grown up in western Pennsylvania’s “Gasland.” Alec's career in the oil and gas sector began after an intriguing conversation with Michael Snyder of Snyder Brothers, leading to his pivotal role in raising investments for alternative energy projects. Known for his comprehensive understanding of the...
Oct 01, 2024•27 min
In this episode appropriately titled, "Bonus Depreciation Explained," we aim to demystify one of the most queried topics in the tax community. Chris explains the fundamental principles of bonus depreciation, underlining its relevance and the strategic advantage it offers to businesses, particularly small entities and real estate investors. Listeners are treated to practical examples that illustrate how bonus depreciation can be maximized and the potential pitfalls to be wary of. During this epis...
Sep 24, 2024•30 min
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 ...
Sep 17, 2024•26 min
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 ...
Sep 10, 2024•38 min
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 milest...
Sep 03, 2024•28 min
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 cla...
Aug 27, 2024•31 min
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 impl...
Aug 20, 2024•26 min
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-fact...
Aug 13, 2024•25 min
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. ...
Aug 06, 2024•31 min
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 t...
Jul 30, 2024•29 min
Episode Summary: In this episode of the Teaching Tax Flow podcast, hosts Chris and John dive into the critical question many homeowners face: should one sell or rent their personal property after moving out? This episode expertly navigates the tax implications, financial considerations, and emotional factors homeowners must weigh when making this decision. With practical insights and real-life examples, the hosts break down complex tax topics like the Section 121 exclusion and depreciation recap...
Jul 23, 2024•31 min
This episode of the Teaching Tax Flow podcast dives deep into the complexities of car and truck deductions for businesses. Joined by a seasoned tax professional, the discussion centers on the eligibility and nuances of vehicle expense deductions, explaining what they are and what they aren't. In a detailed conversation with tax expert Shawn Flattery, listeners will learn who can claim vehicle expense deductions and the criteria involved. The episode explores the distinctions between standard mil...
Jul 16, 2024•32 min
In this episode of the Teaching Tax Flow podcast, hosts John and Chris delve into Chris's top three tax-free income strategies. John and Chris provide invaluable insights on how to legally and ethically minimize taxes over one's lifetime, offering listeners actionable advice on educational savings, Roth accounts, and advanced whole life insurance planning. The conversation kicks off with an immersive discussion on the benefits of 529 plans, how they offer tax-free growth for educational expenses...
Jul 10, 2024•31 min
In this enlightening episode of the Teaching Tax Flow podcast, hosts John and Chris delve into the history of U.S. taxes, providing a timely reflection given the Independence Day holiday. Episode 90 offers a fascinating journey through the evolution of the U.S. tax system, from its early introduction during the Civil War era to the complexities of the current Tax Cuts and Jobs Act (TCJA) of 2017. The conversation also touches upon the future of tax policies with looming elections, making it a mu...
Jul 02, 2024•27 min
About the Guest: Bill Allen is a retired Navy pilot turned real estate investment mogul. With a background as a Navy test pilot, Bill transitioned into real estate, starting with hands-on house flipping and later expanding into large-scale apartment syndications and passive investing. He is the founder of Flip Hacking Live and has a notable presence in the real estate community through teaching and mentoring. Bill’s accomplishments include scaling his real estate operations to hundreds of transa...
Jun 25, 2024•43 min
In the intriguing episode of the Teaching Tax Flow podcast, John and Chris delve headfirst into an important financial debate: "Should you use your savings to pay down or pay off your mortgage?". This episode navigates through various financial strategies, tax considerations, and personal factors that can influence this decision, aiming to provide clarity to listeners who find themselves pondering this financial dilemma. The discussion kicks off with an analysis of current interest rate trends a...
Jun 18, 2024•25 min
In this episode of the Teaching Tax Flow Podcast, hosts Chris and John are joined by guest, Jim Cunningham, and jump deep into the intricacies of selling a business. With a focus on empowering listeners to minimize tax liabilities while navigating significant legal considerations, this episode is a must-listen for business owners considering a transition. Brought to you by Legacy Lock, the episode provides a roadmap to understanding essential components of business sales, including asset vs. sto...
Jun 11, 2024•36 min
In Episode 86 of the Teaching Tax Flow podcast, hosts John and Chris delve into an essential topic for many families: 529 plans. The episode, cleverly titled " What's the 411 with 529 Plans ," explores the ins and outs of these educational savings accounts, aiming to provide listeners with deep insights on how to leverage these plans to minimize tax burdens while saving for education. Sponsored by RepsTracker, the episode also shares an engaging dynamic between the hosts, spiced with personal an...
Jun 04, 2024•29 min
