Q&A: The Tax Strategy Hierarchy Every Small Business Owner Should Know

If I were starting a business today, this is exactly how I’d approach tax planning from the ground up. In this episode, we're tackling tax strategy hierarchy every small business owner should follow. 

From core strategies like hiring your kids and maximizing deductions, to advanced moves like asset purchases, oil and gas investments, and captive insurance, you’ll learn the right order to implement them for maximum savings. We also answer listener questions on short-term rental deductions, the Big Beautiful Bill, and how to structure partnerships for smarter tax planning. 

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Chapters:

(00:00) Starting From Scratch
Mike shares his “from scratch” game plan for small business tax planning and breaks down the difference between core and advanced tax strategies.

(04:04) Big Beautiful Bill Overview
What’s in the Big Beautiful Bill, how it impacts small businesses, and where to find the full breakdown.

(05:00) Planning for Income Phase-Outs
Strategies for lowering AGI to avoid phase-outs and AMT for high earners.

(08:00) Short-Term Rental Deductions
How to qualify, the 100-hour rule, and how bonus depreciation applies.

(12:15) 1099 Income Advantages
Why 1099 workers are treated as business owners and the deductions that come with it.

(14:00) Self-Rental and Asset Purchase Strategies
 Using a self-rental strategy and advanced asset purchases to significantly reduce taxable income.

(15:53) Adjusting S Corp Salary
 How to handle a reasonable salary when business revenue drops.

(17:00) Home Office Deduction Methods
 Comparing the simplified and actual methods for the home office deduction.

(18:46) Structuring Partnerships for Tax Planning
 Entity structures that allow partners with different tax needs to plan separately.

(20:58) Accessing S Corp Profits
 How to take owner’s draws and keep your salary reasonable.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.