# Bad Timing Costs You More Than Bad Investments Ever Will - The Cash Flow Clock

Page: https://stenobird.com/podcast/the-tax-strategy-playbook-7760433/bad-timing-costs-you-more-than-bad-investments-ever-will-the-cash-flow-clock
Text version: https://stenobird.com/podcast/the-tax-strategy-playbook-7760433/bad-timing-costs-you-more-than-bad-investments-ever-will-the-cash-flow-clock.md
Podcast: [The Tax Strategy Playbook](https://stenobird.com/podcast/the-tax-strategy-playbook-7760433)
Published: 2026-06-16T11:00:00+00:00
Episode link: https://api.riverside.com/hosting-analytics/media/615dd0e978aeeaf62b9df674a4bbdbb1feae7b966d63d51fa3e6f8fbf9a1c75a/eyJlcGlzb2RlSWQiOiJiYWU2NzczZS1hNTlhLTQ2ZDctYTY1ZC05N2FkNjUxZDY0ZWMiLCJwb2RjYXN0SWQiOiI4NDdiYmJiNy0zZjM3LTQwM2UtYTI3My1lODM5MjJmNzcwYzgiLCJhY2NvdW50SWQiOiI2OTdiOGE0NmMzYTNjN2MxYzdiMmMyMmYiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmExMWNjNDRhMjdmOWEyZDRkODU4N2Q4L3BvZGNhc3Qtc3R1ZGlvLVRlZGZqLWNvbXBvc2VyLTIwMjYtNS0yM19fMTctNDgtMjAubXAzIn0=.mp3
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Duration seconds: 2224

## Resource

Bad timing destroys more wealth than bad investments ever will. In this episode of The Tax Strategy Playbook, David Wiener (Mr. Cash Flow) sits down with Gary Preisser — Managing Partner of Stonebriar Wealth Advisors and creator of the Cash Flow Clock — to break down exactly how business owners, real estate investors, and CPAs can stop reacting to tax disasters and start designing wealth that works on their terms. 💡 WHAT YOU'LL LEARN IN THIS EPISODE: ✅ What the Cash Flow Clock is and how to apply it to your portfolio today ✅ Why bad TIMING — not bad investments — destroys most financial plans ✅ The "Lazy Zone," "Safe Zone," and "Volatility Zone" of cash flow planning ✅ How asset location (not just allocation) could save you hundreds of thousands in taxes ✅ Why deferring taxes forever is a trap — and how to time your tax bracket strategically ✅ The Widow's Tax Trap that blindsides surviving spouses at the worst moment ✅ When Roth conversions make sense (and when they don't) ✅ How cost segregation, bonus depreciation, and big deduction years fit into lifetime tax planning ✅ Why CPAs must shift from tax preparation to tax planning — and how to do it without overhauling their practice ✅ The first 3 steps any business owner or real estate investor should take in the next 30 days 🕐 CHAPTERS: 00:00 – Introduction: Why timing destroys good investments 02:12 – Meet Gary Preisser & Stonebriar Wealth Advisors 03:36 – The real villain: bad timing, not bad decisions 05:04 – Real client case study: $10M portfolio, wrong asset location 07:31 – Tax planning vs. tax preparation (why April 14th is too late) 10:42 – What is the Cash Flow Clock? (Plain English breakdown) 14:06 – Lifetime tax planning for business owners & real estate investors 17:19 – Selling a business, retiring,…

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## Transcript

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