Ep.#103: Taxation of Collectibles; Wine & When a Hobby becomes a Business.

Ep.#103: Taxation of Collectibles; Wine & When a Hobby becomes a Business.

From Hawaii Retirement Show by Jason Cutitta, CFP®

January 1, 2026 · 19 min · Episode 103

About this episode

Jason Cutitta discusses the taxation of collectibles, particularly focusing on wine, and the distinctions between hobbies and businesses in terms of tax implications.

In this episode of The Hawaii Retirement Show, Jason breaks down the taxation of collectibles, using wine to explain how the IRS treats tangible assets that appreciate in value. He clarifies what the IRS considers a collectible, why these assets can face higher tax rates than stocks, and how long-term gains on collectibles are capped at 28%, with additional taxes potentially applying for higher-income taxpayers. Jason also walks through the critical distinctions between being a hobbyist, an investor, or a business, and why that line matters far more than most people realize. He explains how intent, frequency of sales, and recordkeeping drive tax treatment, when losses are deductible, and how activities like consignment sales or frequent trading can unintentionally trigger business taxation. He closes with practical planning takeaways, emphasizing documentation, holding periods, and awareness of higher tax exposure, reminding listeners that while collectibles can be enjoyable and profitable, the tax rules require careful attention. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

People in this episode

Host: Jason Cutitta

Topics covered

Keywords

Mentioned in this episode

Organizations: IRS

Products: wine

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