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.

00:00 Introduction to Tax Strategy and Entity Selection
04:39 Understanding Entity Types and Their Importance
06:46 The Wrong Way to Choose an Entity
10:37 Choosing the Right Entity for Your Business
17:37 The Future Effect of an Entity Selection
18:53 Practical Steps
24:25 Changing Entity Structures and Common Mistakes
29:23 Listener Questions
31:07 Playbook
33:31 Working with TrueBooks for Tax Strategy
35:18 Wrap-up

📌 Resources & Next Steps:

Work with David on cost segregation and advanced tax strategy: mailto: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.

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