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.

This episode delves into the concept of cost segregation and bonus depreciation in real estate, explaining how it works, its benefits, myths, and considerations for choosing a quality cost segregation firm. The episode provides practical insights for property owners and investors to optimize their tax planning and cash flow.

Takeaways

• Cost segregation and bonus depreciation can significantly improve after-tax returns and free up capital for property owners and investors.
• Choosing a quality cost segregation firm is crucial for ensuring a high-quality engineering-based study and robust audit support.

Stop letting the IRS be your biggest business partner. In this first episode of The Tax Strategy Playbook, host David Wiener (“Mr. Cash Flow”) sits down with tax strategist Greg Taylor to unpack the real reasons real estate investors and business owners quietly overpay the IRS year after year—and what to do about it.

Greg is the founder of Taylor Tax Strategy, where he helps investors and entrepreneurs use proactive planning to legally reduce their tax bill and keep more cash working inside their portfolios.

In this conversation, Greg shares his journey into real‑estate‑focused tax strategy, the “lightbulb moment” that changed how he views the tax code, and the top mistakes he sees even experienced investors make.

You’ll hear:

• The 3 biggest ways investors and operators routinely overpay in taxes

• How proactive planning (vs. once‑a‑year filing) can dramatically change your cash flow

• A real client story where better strategy meant a major tax savings

• The one action you should take in the next 7 days if you suspect you’re overpaying.

If you’re ready to stop writing unnecessary checks to the IRS and start using the tax code as a wealth‑building tool, this episode is your starting point.

Connect with Greg Taylor:

• Website: https://taylortaxstrategy.com

• LinkedIn: https://www.linkedin.com/in/gregtaylor

Connect with your host, David “Mr. Cash Flow” Wiener:

• Website: https://taxstrattegyplaybook.com

• LinkedIn: https://www.linkedin.com/in/cashflowstrategies/

Hit play, take notes, and then send this episode to one investor or business owner you know is probably overpaying in taxes.