Investing Episodes

The conversation explores the critical role of tax strategy in investment decisions, emphasizing the importance of tax mitigation and exit planning. It delves into the distinction between planning for taxes and reacting to taxes, highlighting the impact of tax strategy on long-term wealth. Additionally, it discusses cost segregation, 1031 exchanges, challenges, and the use of Delaware Statutory Trusts (DSTs) as an alternative option. The conversation covers various real estate investment options...

Cost segregation myths could be costing you tens of thousands of dollars in taxes you don't actually owe. In this episode of the Tax Strategy Playbook, David Wiener (Mr. Cash Flow) puts 5 of the most common cost segregation myths up against the actual numbers — and shows exactly which owners end up paying more simply because they never checked. You'll get the exact cost basis threshold, $150,000, that determines whether an engineering-based cost segregation study is worth running on your proper...

I want you to sit with one number: $177,500. That's the tax bill one of my clients avoided entirely — not through a loophole, but by understanding how step-up in basis actually works for real estate investors. In this episode of The Tax Strategy Playbook, I walk through the 5 best assets you can leave your heirs and the 5 worst estate planning traps real estate investors fall into — traps that can cost families six figures in avoidable taxes and legal fees. You'll learn: ✅ How step-up in basi...

Tired Landlords: Escape $1M Tax Bills with a DST 1031 Exchange Are you a real estate investor feeling the exhaustion of active property management? Do the recurring challenges of tenants, toilets, and trash weigh on you, while the thought of selling your appreciated assets fills you with dread over massive capital gains and depreciation recapture taxes? If you're sitting on hundreds of thousands, or even millions, in potential tax liabilities, know that you're not alone, and there is a strate...

Tax Strategy vs TikTok Hacks: 7 Viral Myths That Trigger Audits Are you tired of scrolling through TikTok and seeing “tax hacks” and viral write-off tricks that could actually land you in hot water with the IRS? In this episode of The Tax Strategy Playbook, host David Wiener, also known as “Mr. Cash Flow,” cuts through the noise. He exposes 7 common social media tax myths that are actually audit bait and reveals the legitimate, long-term tax strategies that wealthy investors use instead. If yo...

Here’s a revised YouTube description with a first paragraph that’s intentionally loaded with relevant keywords while still reading naturally. If you’re a high-income W-2 earner, 1099 professional, real estate investor, or business owner looking for advanced tax strategies to reduce taxes, this episode breaks down a powerful oil and gas tax strategy to legally offset W-2 income, use intangible drilling costs (IDC) deductions, and stack oil and gas investing with cost segregation and other tax pl...

What if you could sell a rental property, defer 100% of your capital gains tax and depreciation recapture, and roll every dollar into a bigger, better deal — and keep doing it forever? That's exactly what a 1031 like-kind exchange allows real estate investors to do. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Dave Foster, founder of The 1031 Investor and one of the country's leading experts on 1031 exchange strategies. Dave breaks down the exact rules, timelin...

This episode dives into how landlords use real estate to build durable wealth and tax efficiency, featuring investor, broker, and educator Christian Walsh. Christian shares his journey from traditional real estate work into becoming a trusted guide for everyday investors who want to play the game more strategically. He breaks down how to think like a long-term investor, why understanding local market dynamics matters more than chasing national headlines, and how to structure deals so they actually support your lifestyle and goals. You’ll hear practical examples of using leverage wisely, positioning yourself for opportunities in shifting markets, and avoiding the common mistakes that keep investors stuck. The conversation also touches on building a personal brand as an agent or advisor, communicating clearly with clients, and creating content that attracts serious investors instead of tire-kickers. By the end, listeners walk away with a clearer blueprint for growing a resili…

The 2025 Tax Bill — officially known as the One Big Beautiful Bill — is the biggest tax law change in nearly a decade. And most small business owners and real estate investors are about to sleepwalk right past it. In this episode of The Tax Strategy Playbook, host David Wiener breaks down exactly what the One Big Beautiful Bill means for small businesses, real estate investors, rental property owners, and entrepreneurs — and how to turn these new tax law changes into a concrete action plan befo...

Choosing the wrong entity structure is one of the most expensive mistakes real estate investors and small business owners make — and most don't find out until it's too late. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Matt Bontrager, CPA and managing partner of TrueBooks, a firm that works almost exclusively with real estate investors and entrepreneurs. Matt has reviewed hundreds of real-world LLC and S corp structures and pulls back the curtain on how entity ...

In this episode, we break down cost segregation for real estate investors who want more cash flow and less tax drag on their rentals and commercial properties. You’ll learn how cost segregation accelerates depreciation by carving out 5, 7, and 15-year components inside your property, and how bonus depreciation lets you front load those deductions into the early years of ownership. We cover how cost segregation applies to everyday investors across many asset types: single-family rentals, dupl...

If you're a real estate investor or business owner, tax strategy is the single most powerful wealth multiplier available to you — and most people are using it wrong. In this debut episode of The Tax Strategy Playbook, host David Wiener ("Mr. Cash Flow") sits down with tax strategist Greg Taylor, founder of Taylor Tax Strategy, to unpack exactly why real estate investors and business owners quietly overpay the IRS year after year — and what proactive tax planning can do about it. Greg shares th...