29:54

In this episode of the Main Street Business Podcast, host Mark Kohler and co‑host Matt Sorenson walk side‑hustlers and small‑business owners through practical tax planning for 2023‑2024. They begin by stressing the legal requirement to report all income, whether received on a 1099, under‑the‑table, or from other sources, and explain how to file extensions to avoid audit risk. The conversation then shifts to maximizing deductions: they outline a systematic approach to tracking expenses using spreadsheets, emphasizing common write‑offs such as home‑office space, mileage, equipment, cell‑phone costs, dining, travel, training, and even unconventional items like pets, uniforms, and ski‑pass fees. They discuss the benefits and limits of paying children for legitimate work, noting the tax‑free threshold for minors. The hosts compare business structures, clarifying that an LLC alone does not reduce taxes, while an S‑Corporation can lower self‑employment tax liability, and advise when each entity makes sense. Self‑employment tax mechanics are broken down, highlighting the 15.3 % combined employee‑employer FICA burden. They then cover retirement and health‑savings options—traditional IRA, solo 401(k), and HSA contributions—showing how to extend filing deadlines to make these contributions for the prior tax year. Record‑keeping best practices are reinforced, especially the need for a dedicated business bank account. Finally, they promote using professional tax advisors via their TaxPro network, remind listeners of required BOI/FinCEN filings for LLCs, and encourage proactive, creative tax planning to build wealth while maintaining a side hustle.

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