37:21

In this live YouTube broadcast, CPA‑attorney‑author Mark Kohler walks viewers through practical tax strategies for side‑hustles and small businesses. He begins by framing any 1099‑reported activity—whether Uber, Etsy, or a lemonade stand—as a legitimate business and stresses the “gateway drug” mindset of using side‑income to build wealth. He then outlines five foundational principles: (1) treat the side hustle as a business; (2) report all income even without a 1099; (3) track and defer startup costs until the first dollar of revenue; (4) file Schedule C (or Schedule E for rentals) on the 1040 and understand how losses interact with a W‑2; (5) aggressively claim any expense that produces income. Kohler lists his top six write‑offs—cell‑phone/electronics, travel, auto (mileage vs. actual), supplies/equipment, meals, and home‑office—and explains how each can be documented. He then dives into rental‑property tax rules, passive‑loss limits, depreciation vs. repairs, and the equivalence of Airbnb/VRBO to long‑term rentals. The discussion moves to entity selection, recommending a single S‑Corp (or LLC) that can own multiple DBAs or subsidiary LLCs, rather than a separate corporation for each venture. He addresses niche scenarios such as using Roth IRAs or HSAs to fund equipment‑leasing entities, deducting RVs and yachts when used for business transportation, and the limits on student‑loan interest deductions. Throughout, Kohler answers live viewer questions from across the U.S. and abroad, providing concrete examples of how to apply the principles to Uber drivers, Airbnb hosts, pressure‑washing businesses, and more. The session ends with promotional offers for his 2020 calendar, workshops, and contact information for further tax‑legal consulting.

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