46:11

In this open‑forum episode of the Main Street Business podcast, hosts Mark Kohler and Matt Sorenson field a rapid‑fire series of listener questions covering a wide range of small‑business tax and legal issues. They begin with advice on finding the cheapest high‑deductible health plan that qualifies for a Health Savings Account (HSA) and explain the tax benefits of HSAs. The conversation moves to LLC formation, board of advisors, and the importance of documenting annual meetings for asset‑protection purposes. They discuss the tax implications of using an S‑corp for a high‑income side hustle, especially how payroll taxes (FICA, Medicare) interact with a large W‑2 salary and the limited savings from S‑corp election at high incomes. The hosts stress aligning with a knowledgeable tax advisor and introduce their Certified Tax Advisor network. A listener’s quote about the difficulty of income tax is humorously addressed. They then dive into short‑term rental loss deductions, the at‑risk rules, and historical context from the 1980s Savings‑and‑Loan crisis to illustrate why loss write‑offs are limited to the amount at risk, including recourse debt. The “trifecta” framework—operations (left), assets (right), and estate planning (bottom)—is explained as a holistic wealth‑building model. Mileage reimbursement versus mileage deduction is clarified for sole proprietors, S‑corps, and partnerships. The solo‑401(k) part‑time employee rule change under SECURE Act 2.0 is highlighted. Additional quirky topics include the tax treatment of a pool‑rental side business (Swimply), the possibility of deducting security dogs and firearms as business expenses, and the nuances of using a home‑based pool as a Schedule C versus Schedule E activity. Throughout, the hosts blend practical guidance, humor, and frequent reminders that the content is educational, not formal legal advice. The episode concludes with a call for more questions and a reminder to build a “trifecta” plan for tax‑efficient wealth creation.

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