Teaching Tax Flow: The Podcast

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 ag...

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 mon...

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 exa...

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 exp...

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 immers...

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....

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 an...

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...

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...

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...

In this episode of the Teaching Tax Flow podcast, we jump into the intricacies of 1031 exchanges, a topic vital for anyone looking to optimize their real estate investments. Focusing on the practical aspects of 1031 exchanges with guest, Scott Saunders, who provides a detailed explanation of the associated rules, from identification to replacement property guidelines. The conversation unearths val...

In this episode of the Teaching Tax Flow podcast, Chris Piccurrio and his co-host John Tripolsky delve into valuable tax strategies for low to mid-income households, specifically targeting those with an annual taxable income of around $100k and below.  The conversation quickly gets to the meat of the episode: tax planning for average-income earners. With insight and enthusiasm, Chris outlines why...

In this episode of the "Teaching Tax Flow" podcast, we jump into the critical subject of long-term care (LTC) planning. Bringing on board expertise and personal insights, guest Brooke Crane Acre explores what individuals need to consider while preparing for potential LTC needs. Brooke shares stories and advice to help listeners understand the significance and nuances of LTC. Two contrasting exampl...

This episode sheds light on the intricacies of tax rules that rental property investors face. From the various deductions and tax benefits real estate investors can enjoy to the different forms of property ownership and their implications on tax filings, the episode is brimming with valuable guidance. Listeners get a rundown of how rental properties are taxed, the differences between gross and net...

In this episode, hosts John and Chris dive into the often overlooked, yet insightful, Internal Revenue Service (IRS) Databook. The conversation opens with a spotlight on the importance of understanding IRS operations and statistics that can empower taxpayers to minimize their lifetime taxes legally and ethically. Discover key trends in electronic return filings and insights into IRS auditing pract...

In this episode of the Teaching Tax Flow podcast, we welcome Will Lopez of Gusto to unearth the critical significance of payroll beyond its traditional perception. The conversation dives deep into the transformative power of modern payroll services provided by Gusto, as well as how efficient payroll processing can be leveraged for strategic tax planning and business growth. Explore how shifting fr...

Episode Summary: In this episode of the Teaching Tax Flow podcast, Chris Picciurro steps into the spotlight as he sheds light on his day-to-day life as a tax professional. The conversation takes an intimate turn as Chris shares his journey from an entrepreneurial paperboy to becoming a knowledge powerhouse in the realm of taxes. This episode delves into the intricacies of a tax professional's worl...

Let's embark on a journey through the world of retirement accounts tailored for the modern entrepreneur in this episode of the Teaching Tax Flow podcast. We jump right into how to best create a robust financial future, while cleverly navigating through various retirement plans. In the multi-faceted discussion, Chris tactfully breaks down retirement account options, from the basic traditional IRA t...

In this episode of the Teaching Tax Flow podcast, the hosts dive into the intricate world of short-term rental (STR) investments and the associated tax loopholes. Guest expert Arda Bircan brings his wealth of knowledge and real-world experience to the table, providing listeners with a unique perspective on how to leverage STRs for financial gain and tax efficiency. The podcast explores everything...

In this episode of the Teaching Tax Flow podcast, hosted by Chris Picciurro and John Tripolsky, they dive into the nuances of parental tax strategies. With a focus on empowering parents to legally and ethically minimize the taxes they will pay over their lifetimes, episode 76 is a must-listen for parents eager to optimize their tax planning. The hosts meticulously break down complex tax strategies...

In this episode of the Teaching Tax Flow podcast, hosts Chris and John dive deeply into the intricacies of 1099 forms with the help of guest expert Kaitlyn Rummel from EH Business Services. Kaitlyn brings her experience to the table, discussing how 1099 forms work, their significance in tax documentation, and strategic tips for businesses to manage them efficiently. Opening with an introduction to...

In this episode, Chris & John cover the beneficial sphere of tax advantages that come with homeownership. This conversation is a must-listen for current and prospective homeowners aiming to understand the financial and tax implications of owning a primary residence. The duo unpacks several key benefits, providing listeners with actionable tax tips that could lead to significant savings. Throug...

In the pursuit of legally reducing lifetime tax payments, this episode unveils the strategic advantages of understanding step-up in basis and how it applies to various inherited assets. Chris succinctly breaks down the essence of cost basis and its implications for capital gains tax. His expertise shines through as he presents everyday scenarios, articulating a clear picture of the benefits and in...

In this episode of the Teaching Tax Flow podcast, the hosts, John Tripolsky and Chris Picciurro, welcome Lisa McCarthy to demystify the often-interconnected worlds of bookkeeping, accounting, and tax preparation. Kicking off the conversation, Lisa vividly shares her accidental yet fortuitous dive into bookkeeping, sprouting from her innate love for numbers and a chance meeting with QuickBooks soft...

Episode Summary: In this episode of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky jump into the complexities of K-1 forms with a blend of expertise and humor. Designed to capture the interest of taxpayers and professionals alike, the episode breaks down the purpose, importance, and timing of K-1 forms, which are crucial for individuals involved in partnerships, S corporat...