Teaching Tax Flow: The Podcast

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 su...

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 obli...

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 ...

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 insura...

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...

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...

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 cri...

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 benef...

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 touc...

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 accompl...

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.

Th...

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 und...

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 al...

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 valuable tips for investors at...

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 tax strategy is not just fo...

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 examples from Brooke's personal l...

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 income taxation, and the p...

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 practices that every taxpayer s...

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 from an arduous, compliance-...