Our latest discussion centers on effective tax planning, especially for those involved in real estate investing, highlighting how proper tax strategies can significantly impact your financial outlook. We explain the critical role of understanding tax deductions and navigating IRS regulations to avoid common pitfalls. This episode is essential for anyone…
This video clarifies crucial rules for IRA real estate investments, particularly emphasizing that you should not directly handle your investment property. We discuss how to properly work on an IRA-owned property and the role of self directed ira accounts in real estate, offering insights vital for your retirement planning. Understanding…
This video discusses how using an IRA asset for personal use is a direct violation of tax rules, which is crucial for proper personal finance. It highlights how such actions can lead to the entire IRA being considered distributed, impacting your retirement planning. Understanding these pitfalls is essential for safeguarding…
This episode focuses on common pitfalls and mistakes associated with using a "self directed ira", especially for "real estate investing". We discuss how errors, including record-keeping nightmares, can jeopardize your "retirement planning". Understanding these issues is crucial for anyone considering or already using an IRA for property investments to avoid…
This video discusses the potential pitfalls of a self directed ira, highlighting that a single mistake can jeopardize your retirement savings. We warn about prohibited transactions and self-dealing, emphasizing the need for careful management to avoid negative consequences for your retirement. Understanding these ira mistakes is crucial for anyone considering…
This video examines the crucial differences between tax evasion and tax avoidance, offering practical insights into how investors can legally minimize their tax burden. We discuss common mistakes in bookkeeping and entity selection that often lead to IRS exams, especially for those involved in real estate investing. Understanding proper tax…
Many real estate investors face financial ruin not from poor deals, but from critical tax decisions they often overlook. This episode exposes common tax traps that quietly erode investor wealth, stressing the importance of proper tax planning. Learn how to safeguard your investments by understanding tax implications and avoiding common…
⚠️ Most real estate investors don’t lose money on bad deals — they lose it on BAD TAX DECISIONS they didn’t even know they were making. In this episode of The Tax Strategy Playbook, host David Wiener (Mr. Cash Flow) sits down with Scott Estill — a former IRS Senior…
This video emphasizes that individuals bear the responsibility for what they report on their tax returns, even if the idea originated from social media or tax preparers. Fraudulently claiming credits can result in severe irs penalties, repayment with interest, and potential criminal charges, highlighting the importance of accurate tax advice.…
This video explains that deducting the cost of a car does not make it free, as the math doesn't always work out in your favor, especially with a vehicle tax deduction. It highlights how overstated vehicle deductions can be considered "low-hanging fruit" during an irs audit, potentially leading to significant…
This video examines common issues when clients are advised to place all business operations and assets into a limited liability company, often leading to higher self employment tax. We explore how incorrect business structures can complicate tax planning and make business exit planning messy. Understanding proper legal structures is crucial…
This video discusses how tax benefits can amplify real businesses, not just hobbies. It highlights real profit potential and how operations are built, suggesting that properly structured businesses can enjoy significant tax deductions. This crucial tax planning step can lead to business growth and business success for the entrepreneur. See…
We discuss the "Big Beautiful Bill Act of 2025," which reinstates 100% bonus depreciation, offering significant tax deductions. This video highlights crucial tax planning steps to maximize your tax savings. Learn how to save on taxes and navigate the changing provisions to benefit your financial future. Your host: David Wiener,…
This video, featuring Tommy Olson, Vice President of K Properties, provides key insights for landlords seeking effective investment strategies. Learn how to leverage a 1031 exchange into a DST to generate passive income and ultimately up-REIT into a liquid REIT portfolio. This approach helps in managing and potentially avoiding significant…
This video explains why wealthy individuals avoid making their entire lives a "tax write off," as it can be a dangerous practice. For an expense to be a legitimate tax deduction, it must be ordinary and necessary for your trade or business, and not primarily personal. Blurring the line between…
The IRS has flagged misleading tax advice on social media as a major concern, listing it among the 2026 Dirty Dozen scams. These widespread tax scams are costing Americans millions, with many victims losing tens of thousands of dollars. It's crucial to understand the difference between a viral hack and…
This video highlights the growing issue of tax scams, particularly those found on social media platforms, and the serious consequences they can bring. It's crucial for effective tax planning to avoid common tax traps and tax mistakes that can lead to significant financial repercussions. Understanding IRS audit triggers is key…
This video highlights the growing issue of tax scams, particularly those found on social media platforms, and the serious consequences they can bring. It's crucial for effective tax planning to avoid common tax traps and tax mistakes that can lead to significant financial repercussions. Understanding IRS audit triggers is key…
Tired of TikTok “tax hacks” and viral write‑off tricks that could actually trigger an IRS audit? In this Tax Strategy Playbook episode, David Wiener (Mr. Cash Flow) exposes 7 social media tax myths and shows you the real 2026 tax strategy wealthy investors use instead. If you’re serious about long‑term…
This video examines the crucial warning signs to consider when looking into oil and gas industry deals. We stress the importance of understanding the underlying economics and the operator's track record before you invest in oil. Given that investing in oil and gas can be complex, it's vital to proceed…
This video explains how real estate losses can be used to offset oil and gas profits, treating these losses as non-passive. Learn how to optimize your tax planning and how to save on taxes through these powerful tax strategies. We explore how this tax strategy encourages domestic energy production by…
In this video, Mark Pearlberg, a CPA, discusses advanced tax strategy for high-income investors, integrating oil and gas investments with cost segregation and Roth conversion strategies. He shares how these methods can lead to significant tax deductions and savings. Learn how a comprehensive tax planning approach can benefit your financial…
If you're considering oil and gas write-offs, start with a reality check of your profile. Consult with your tax expert to discuss your income, tax bracket, and current tax strategy. This crucial tax planning step will help you understand how to save on taxes and if oil and gas deductions…
This video explores the challenges landlords face, particularly the "3 T's" of tenants, toilets, and trash, and how some consider oil and gas investments as an alternative. While real estate remains a strong option, understanding the eviction process and effective tax planning is vital for property owners. We discuss how…
