{"podcast":{"title":"The Tax Strategy Playbook","slug":"the-tax-strategy-playbook-7760433","podcast_index_feed_id":7760433,"rss_url":"https://api.riverside.fm/hosting/qAoIrP0O.rss","website_url":"https://taxstrategyplaybook.com","image_url":"https://hosting-media.riverside.com/media/podcasts/847bbbb7-3f37-403e-a273-e83922f770c8/logos/2e74a69c-4cea-4a5e-9f86-9f08e7686b79.png","author":"David Wiener, \"Mr. Cash Flow\"","episode_count":19,"summary":"The Tax Strategy Playbook is where real estate investors and business owners learn how to stop overpaying the IRS and turn taxes into an opportunity center instead of an annual pain point. Each episode, host David Wiener (“Mr. Cash Flow”) sits down with CPAs, tax attorneys, cost segregation experts, and top investors to break down complex tax rules into clear, step‑by‑step strategies you can actually use. You’ll hear real case studies, before‑and‑after numbers, and practical checklists on things like cost segregation, bonus depreciation, real estate professional status, short‑term rental strategies, entity structure, and more—without legalese or fluff. Expect straight talk, tactical advice you can hand to your CPA, and simple action items at the end of every show so you always know what to do next.","last_synced_at":"2026-07-14T22:17:11.667852+00:00","page_url":"https://stenobird.com/podcast/the-tax-strategy-playbook-7760433"},"episode":{"title":"How Tired Landlords Are Escaping $1M Tax Bills Using DST 1031 (Without Buying Another Property)","slug":"how-tired-landlords-are-escaping-1m-tax-bills-using-dst-1031-without-buying-another-property","published_at":"2026-06-02T11:00:00+00:00","page_url":"https://stenobird.com/podcast/the-tax-strategy-playbook-7760433/how-tired-landlords-are-escaping-1m-tax-bills-using-dst-1031-without-buying-another-property","show_page_url":"https://stenobird.com/podcast/the-tax-strategy-playbook-7760433","url":"https://api.riverside.com/hosting-analytics/media/f3934666303a310daf6abddc0276b0ee96d7de2bfea61d4c90c5105ce4224ca4/eyJlcGlzb2RlSWQiOiIzMmZiODNhNy03OTQ1LTQwY2QtYWQ1Yy0yZWJhOTA5YzRkNDUiLCJwb2RjYXN0SWQiOiI4NDdiYmJiNy0zZjM3LTQwM2UtYTI3My1lODM5MjJmNzcwYzgiLCJhY2NvdW50SWQiOiI2OTdiOGE0NmMzYTNjN2MxYzdiMmMyMmYiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmEwZjkyM2ZkMzRlMjg4MThkMTc4NWUyL3BvZGNhc3Qtc3R1ZGlvLVRlZGZqLWNvbXBvc2VyLTIwMjYtNS0yMl9fMS0xNi0xNS5tcDMifQ==.mp3","audio_url":"https://api.riverside.com/hosting-analytics/media/f3934666303a310daf6abddc0276b0ee96d7de2bfea61d4c90c5105ce4224ca4/eyJlcGlzb2RlSWQiOiIzMmZiODNhNy03OTQ1LTQwY2QtYWQ1Yy0yZWJhOTA5YzRkNDUiLCJwb2RjYXN0SWQiOiI4NDdiYmJiNy0zZjM3LTQwM2UtYTI3My1lODM5MjJmNzcwYzgiLCJhY2NvdW50SWQiOiI2OTdiOGE0NmMzYTNjN2MxYzdiMmMyMmYiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmEwZjkyM2ZkMzRlMjg4MThkMTc4NWUyL3BvZGNhc3Qtc3R1ZGlvLVRlZGZqLWNvbXBvc2VyLTIwMjYtNS0yMl9fMS0xNi0xNS5tcDMifQ==.mp3","summary":"Are you a tired landlord sitting on hundreds of thousands — or even millions — in capital gains and depreciation recapture, terrified of the tax bill that comes with selling? You're not alone. And there IS a better way. In this episode of The Tax Strategy Playbook, host David Wiener (Mr. Cash Flow) sits down with Tommy Olson, Vice President at Kay Properties & Investments — one of the nation's leading Delaware Statutory Trust (DST) advisory firms — to walk through exactly how investors are using DST 1031 exchanges and 721 UPREIT strategies to exit active real estate without writing a seven-figure check to the IRS. 🔑 What You'll Learn: ✅ What a Delaware Statutory Trust (DST) actually is — in plain English ✅ How to defer $800K+ in capital gains AND $300K in depreciation recapture using a 1031 exchange into a DST ✅ Why California landlords can lose up to 50% of their sale proceeds in taxes if they sell outright ✅ The real risks of DSTs that most advisors won't tell you about ✅ How a $3M commercial property sale was diversified across 6 DSTs for stable, passive income ✅ What a 721 UPREIT is and how it can provide a path to liquidity and estate planning advantages ✅ The \"swap till you drop\" strategy for lifetime tax deferral ✅ Who is (and isn't) a good candidate for the DST-to-UPREIT pathway ✅ The top questions to ask BEFORE you invest — and why your CPA needs to be in this conversation early 💡 Whether you're approaching retirement, burned out on property management, or just want your equity working harder without the headaches, this episode breaks down one of the most powerful — and underutilized — tax strategies available to real estate investors in 2026. 👉 Ready to explore your options? Visit kpi1031.com to access free DST resources, recorded webinars, and schedule a…","meta_description":"Are you a tired landlord sitting on hundreds of thousands — or even millions — in capital gains and depreciation recapture, terrified of the tax bill that…","key_points":[],"chapters":[],"topics":[],"duration_seconds":2484,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/the-tax-strategy-playbook-7760433/episodes/how-tired-landlords-are-escaping-1m-tax-bills-using-dst-1031-without-buying-another-property/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/the-tax-strategy-playbook-7760433/how-tired-landlords-are-escaping-1m-tax-bills-using-dst-1031-without-buying-another-property.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}