{"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":"LLC vs S Corp: The Entity Mistakes Costing Real Estate Investors Thousands","slug":"llc-vs-s-corp-the-entity-mistakes-costing-real-estate-investors-thousands","published_at":"2026-03-24T08:00:00+00:00","page_url":"https://stenobird.com/podcast/the-tax-strategy-playbook-7760433/llc-vs-s-corp-the-entity-mistakes-costing-real-estate-investors-thousands","show_page_url":"https://stenobird.com/podcast/the-tax-strategy-playbook-7760433","url":"https://api.riverside.com/hosting-analytics/media/44c3e0c86286e88659f72f31280bb4ce81e7066b5cd132a7b2796374509ca347/eyJlcGlzb2RlSWQiOiJkMThiMDdlZC1mMjVlLTRkYWUtODhiNi04NzZiZGIyOGJlMzMiLCJwb2RjYXN0SWQiOiI4NDdiYmJiNy0zZjM3LTQwM2UtYTI3My1lODM5MjJmNzcwYzgiLCJhY2NvdW50SWQiOiI2OTdiOGE0NmMzYTNjN2MxYzdiMmMyMmYiLCJwYXRoIjoibWVkaWEvY2xpcHMvNjliYjA0OGIwZWM4MjcyN2MyZDkyN2UxL3BvZGNhc3Qtc3R1ZGlvLVRlZGZqLWNvbXBvc2VyLTIwMjYtMy0xOF9fMjEtMS0xNS5tcDMifQ==.mp3","audio_url":"https://api.riverside.com/hosting-analytics/media/44c3e0c86286e88659f72f31280bb4ce81e7066b5cd132a7b2796374509ca347/eyJlcGlzb2RlSWQiOiJkMThiMDdlZC1mMjVlLTRkYWUtODhiNi04NzZiZGIyOGJlMzMiLCJwb2RjYXN0SWQiOiI4NDdiYmJiNy0zZjM3LTQwM2UtYTI3My1lODM5MjJmNzcwYzgiLCJhY2NvdW50SWQiOiI2OTdiOGE0NmMzYTNjN2MxYzdiMmMyMmYiLCJwYXRoIjoibWVkaWEvY2xpcHMvNjliYjA0OGIwZWM4MjcyN2MyZDkyN2UxL3BvZGNhc3Qtc3R1ZGlvLVRlZGZqLWNvbXBvc2VyLTIwMjYtMy0xOF9fMjEtMS0xNS5tcDMifQ==.mp3","summary":"You’re about to find out whether your LLC or S corp is quietly costing you thousands in taxes. In this episode of The Tax Strategy Playbook, host David Wiener sits down with Matt Bontrager, CPA, managing partner of TrueBooks, a firm that works almost exclusively with real estate investors and entrepreneurs. Matt has seen hundreds of real‑world structures—good, bad, and ugly—and he pulls back the curtain on how entity decisions actually impact your tax bill, liability protection, and future flexibility. 🔑 In this episode, you’ll learn: Why most investors misuse LLCs and think they’re a tax strategy (they’re not). When an S corp actually makes sense—and when it becomes an expensive headache. Why putting rentals inside an S corp can backfire and trigger surprise taxable events. Whether you should use one LLC or many for multiple properties (and how Matt thinks about risk vs admin costs). How married couples, flippers, wholesalers, and small business owners should approach entity selection differently. Matt’s simple 2‑entity starting setup for people who feel totally overwhelmed. If you’ve ever copied a friend’s entity structure, formed an LLC because “that’s what everyone does,” or wondered whether you’re leaving money on the table with the wrong setup…this conversation could literally be worth five figures to you over the next few years. 📌 Resources & Next Steps: Work with David on cost segregation and advanced tax strategy: David.wiener@cashflowstrategies.us Learn more about Matt and TrueBooks: https://truebookscpa.com Subscribe for more real estate tax strategy episodes and playbooks. 👍 If this episode helps you, hit like, subscribe, and drop a question in the comments about your current entity setup—we may answer it in a future episode.","meta_description":"You’re about to find out whether your LLC or S corp is quietly costing you thousands in taxes. In this episode of The Tax Strategy Playbook, host David Wi…","key_points":[],"chapters":[],"topics":[],"duration_seconds":2173,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/the-tax-strategy-playbook-7760433/episodes/llc-vs-s-corp-the-entity-mistakes-costing-real-estate-investors-thousands/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/llc-vs-s-corp-the-entity-mistakes-costing-real-estate-investors-thousands.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}