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If you earn over $250,000 or plan to sell a highly appreciated asset, this episode could save you hundreds of thousands in taxes. Most business owners stop at basic deductions and retirement plans, but the wealthy use strategies that go far beyond that. 

In this episode, we break down the five categories of advanced tax planning, when they apply, and how to use them the right way.

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Chapters

(00:00) When Advanced Tax Planning Matters
Why high-income earners and those selling appreciated assets should consider advanced strategies.

(01:00) Core vs. Advanced Strategies
The difference between foundational tax tactics available to everyone and advanced ones designed for high earners or large one-time gains.

(03:10) The Government Rewards Tax Planning
How tax incentives are built to encourage investment in business, housing, and energy projects.

(05:00) The Five Categories of Advanced Tax Strategies
An overview of the five areas where the wealthy focus their planning.

(05:23) Advanced Retirement Planning
Cash balance plans, mega backdoor Roths, non-qualified plans, and self-directed accounts for those already maxing out standard retirement limits.

(06:24) Asset Purchase Strategies
Using leverage and depreciation to create large year-one deductions. Example: turning a $10,000 down payment on a Turo car into a $100,000 deduction.

(08:00) Asset Donation Strategies
Buying assets at a discount and donating them at full fair market value to increase charitable deductions.

(09:00) Oil and Gas Investments
How investors receive 80 to 90 percent year one deductions through intangible drilling costs and depletion allowances.

(10:14) Captive Insurance Companies
Creating your own insurance company to protect your business while shifting income into a tax-advantaged structure.

(11:16) What to Consider Before Using Advanced Strategies
 Material participation requirements, IRS scrutiny, vendor due diligence, and understanding investment or loan obligations.

(14:00) Finding the Right Fit
Why working with a tax strategist helps you find the combination of strategies that fits your goals.

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 you