From IRS: http://www.irs.gov/publications/p535#en_US_2021_publink1000209178
"Advertising expenses. You can generally deduct reasonable advertising expenses that are directly related to your business activities. Generally, you can’t deduct amounts paid to influence legislation (for example, lobbying). For more information, see Lobbying expenses, later. You can usually deduct as a business expense the cost of institutional or goodwill advertising to keep your name before the public if it relates to business you reasonably expect to gain in the future. For example, the cost of advertising that encourages people to contribute to the Red Cross, to buy U.S. savings bonds, or to participate in similar causes is usually deductible."
"Charitable contributions. Cash payments to an organization, charitable or otherwise, may be deductible as business expenses if the payments aren’t charitable contributions or gifts and are directly related to your business. If the payments are charitable contributions or gifts, you can’t deduct them as business expenses. However, corporations (other than S corporations) can deduct charitable contributions on their income tax returns, subject to limitations. See the Instructions for Form 1120 for more information. Sole proprietors, partners in a partnership, or shareholders in an S corporation may be able to deduct charitable contributions made by their business on Schedule A (Form 1040). Example. You paid $15 to a local church for a half-page ad in a program for a concert it is sponsoring. The purpose of the ad was to encourage readers to buy your products. Your payment isn’t a charitable contribution. You can deduct it as an advertising expense. Example. You made a $100,000 donation to a committee organized by the local Chamber of Commerce to bring a convention to your city, intended to increase business activity, including yours. Your payment isn’t a charitable contribution. You can deduct it as a business expense."
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