1:05:23

In this episode of the Main Street Business podcast, hosts Matt Sorenson and Mark Kohler field a rapid‑fire series of listener questions covering a wide range of tax and legal issues that affect small‑business owners and self‑employed individuals. They begin with a reminder of filing deadlines for partnerships, S‑corps, and sole proprietors, then dive into the CARES Act 401(k)/IRA distribution rules, explaining the three‑year tax spread, loan vs. distribution options, and state‑tax considerations for a California‑to‑Idaho move. The hosts discuss PPP loan forgiveness, the ongoing dispute between Congress and the IRS over expense deductions, and upcoming content on the topic. They evaluate entity‑structuring strategies, critiquing a proposed personal‑property‑trust‑into‑Wyoming‑LLC scheme and recommending charging‑order‑protected Wyoming LLCs for rental‑property holdings. They advise on self‑directed retirement accounts, including using blocker C‑corps for business investments, Roth vs. traditional account segregation within solo 401(k)s, and the mechanics of Roth conversions under the CARES Act. The conversation moves to HSA contribution eligibility after a job loss, the tax benefits (or lack thereof) of raw land versus rental property, and liability exposure when a solo 401(k) holds real‑estate. They explain creditor protection differences across states and the importance of using LLCs to shield the retirement plan and the trustee. The hosts also cover S‑corp versus sole‑prop/LLC for side‑hustles, payroll calculations, audit risk, and the timing of S‑corp formation near year‑end. Additional topics include stepped‑up basis on inherited businesses, strategies to minimize estate tax, and the potential impact of the Biden administration’s tax plan on stepped‑up basis. Throughout, the hosts blend technical detail with humor, encourage listeners to seek professional consultation, and promote their own consulting services and upcoming books.

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