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Have you ever considered how advanced tax strategies, from customized retirement contributions to optimizing home office deductions, might lower your overall tax burden?

In this Q&A episode, host Mike Jesowshek answers listener questions on various tax topics. He covers issues ranging from retirement planning strategies, such as after‑tax contributions and Roth conversions in a solo 401(k), to the proper methods for paying oneself as a sole proprietor versus an S corporation. Mike also explains home office deductions, board meeting expenses, handling duplicate tax forms, and business entity conversions.

[00:00 - 05:02] Retirement Contributions and Solo 401(k) Options

• Mike discusses using after‑tax contributions and a Roth conversion in a solo 401(k) for high‑income earners.
• New members receive immediate access to a comprehensive suite of tax-saving tools and consultations.

[05:02 - 10:42] Owner Draws, Home Office Deductions, and Board Meeting Expenses

• Mike explains how to oneself as a sole proprietor using owner draws versus payroll for S corporations.
• Understand that taking money out of a business as an owner draws does not reduce taxable profit.
• Ensure that business spaces are used exclusively for business, and document meetings carefully when using home space.

[10:42 - 15:32] Hiring Family Members, Deducting Mileage Expenses, and Entity Conversion

• Mike discusses claiming mileage expenses when an employee uses a personal vehicle for business.
• Recognize that converting a C corporation back to an LLC may trigger taxable events; professional consultation is advised.

[15:32 - 20:17] Handling Duplicate 1099 Forms and Short-Term Rental Deductions

• Work with the issuer to correct mistakes or offset the extra reporting with a matching expense entry.
• Understand the timing of deductions and whether expenses need to be capitalized based on service start dates.

[20:17 - 27:20] S Corporation and Subsidiary Structures; Home Office with Additional Facility

• Mike details the benefits of an S corporation holding company structure for multiple LLCs and addresses home office deductions when using a separate facility.
• Proper structuring can consolidate profit and loss reporting, and the administrative office rule allows a home office deduction even when an additional business location exists.

Direct Quotes:

"If you are helping out family members, and those family members can also do some work for your business, why not get a business deduction for that help that you want to do anyways?" - Mike Jesowshek, CPA

Check out this episode’s blog post! Visit https://www.taxsavingspodcast.com/blog/tax-q-a-short-term-rentals-1099-confusion-entity-conversions-and-creative-tax-strategies

Click here to book a demo call or you can visit https://taxelm.com/demo/

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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