Business Episodes

Took a COVID EIDL loan and have not thought about it in years? Check your status today. In late March the SBA moved hundreds of thousands of non-performing EIDL and PPP loans to the Treasury Department for enhanced collection, the hardship payment plans ended, and an EIDL loan default now gets collected like any other federal debt. The Treasury Offset Program can take your tax refund, administrative wage garnishment can take up to 15 percent of your paycheck, and a collection fee of roughly 30 p...

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. These are traps that can cost families six figures in avoidable taxes and legal fees. You'll learn: ✅ How step-up...

The IRS has recently announced a critical 90-day settlement window for syndicated conservation easements. After this period expires, participants could face a staggering 40% penalty and a near-complete loss of their claimed deductions. If you or your clients have ever been involved in a syndicated conservation easement, this episode is essential listening. Joining host David Wiener is Victoria Boon, a former IRS Senior Revenue Agent and Subject Matter Expert from the Large Business & Internat...

Bad Timing Costs You More Than Bad Investments Ever Will - The Cash Flow Clock On The Tax Strategy Playbook, host David Wiener, known as "Mr. Cash Flow," dives deep into a critical financial concept with guest Gary Preisser. Gary is the Managing Partner of Stonebriar Wealth Advisors and the innovative creator of the Cash Flow Clock, a revolutionary framework designed to help business owners, real estate investors, and their CPAs move beyond reactive tax planning to proactively design wealth tha...

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...

The R&D tax credit is a dollar-for-dollar federal credit for businesses that solve technical problems, and most of the companies that qualify have never claimed it. No lab coats, no patents, and no research department required. If you run a manufacturer, a software company, an architecture or engineering firm, a construction company, or even a winery or brewery, and your people are paid to work through problems they don't already know how to solve, this episode is for you. In this episode of Th...

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 before ...

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 s...

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 the ...