Compliance & Audits Episodes

Gain insights into tax compliance and audit prevention strategies, focusing on how to navigate common pitfalls and avoid costly issues with the IRS.
24
Aug. 18, 2026

Cost Segregation Audit: The 5 Documents That Save You

A cost segregation audit isn't an accusation. It's a request for proof. Here's the IRS's own checklist (Pub. 5653) so your study passes every time. David Wiener breaks down the IRS Cost Segregation Audit Techniques Guide (Publication 5653) and the 13 elements examiners use to evaluate every study. You'll see exactly what an information document request looks like and why accuracy-related penalties can turn a saved deduction into a five-figure loss. What you'll learn: • Why cost segregation stu...
20
July 21, 2026

Cost Segregation Myths vs Reality | Which Owner Pays More?

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 property...
16
June 23, 2026

Former IRS Agent: Why Syndicated Conservation Easements Are About to Blow 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...
Guest: Victoria Boon
15
June 16, 2026

Tax Timing Mistakes That Cost You More Than Any Bad Deal

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...
Guest: Gary Preisser
12
May 26, 2026

Tax Strategy vs TikTok Hacks: 7 Viral Myths That Trigger Audits

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...