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I have reviewed your entire thread here and do not agree with how you are reporting this, if I understand your situation correctly.   First and foremost, being an LLC does not change anything for tax purposes. Being an LLC is a legal structure created under state law to provide asset protection.  The IRS treats a single member LLC as a "disregarded entity" and you file a Schedule C for your business just like a sole proprietor.    From your previous post it looks like you have been a sole proprietor dating back to 2020. 2020  - $1200 indep contractor 2021  - $  685      " 2022 + $1400     " 2023  - $519      " 2024  - $828      " 2025  - $1900   begin operating as an llc with EIN  2026   ~+3000  Just because you created a LLC and got an EIN makes no changes to your tax situation. I am assuming these prior years income and expenses were reported on a Schedule C with your tax return. I also assume you have used the same principal business or profession and business code each of these years on your Schedule C.   If that is true, you do not have, nor can you deduct start up expenses. You essentially started your business in 2020 and have run your business continuously since then. Your expenses related to creating your LLC would have been deducted in the year you paid those expenses.   When you said, "I decided to allow a theatre to produce my play, pro bono in order to possibly get promotional video to use to get it produced for profit", I am assuming this theatre is not a not-for-profit theatre and they are not a 501(c)(3).   Since you have an established business and you are wanting to deduct expenses for pro bono work to a non-charity, this is subject to Internal Revenue Code (IRC) Section 162. The IRS will be looking for the statutory standard of "Ordinary and Necessary" and the "Business Purpose Test" when determining if you can deduct the expenses related to that pro bono work.  Additionally, the standard the IRS applies is an expense must be directly related to your business and incurred with a primary motive of making a profit.    I can see the argument that the "business purpose" is Advertising, since you intend to get a promotional video to use for producing for profit.  I think this argument can be backed up by the Supreme Court case Welch v. Helvering (1933). In this case, the Court established that for an expense to have a valid "business purpose," it must be more than just "helpful"—it must be a standard practice in that specific industry. If you provide free services to a non-charity, the Welch standard requires you to prove a profit-driven business person would have made the same choice because it was a logical strategy to make more money in the long run. My opinion is you made a logical strategy to make more money in the future.   Working with that assumption, you can deduct the expenses related to the pro bono work, (mileage, meals, etc.) as a business expense in the year the expense was incurred. I have already addressed why these are not start-up expenses.   For future reference, if the IRS questions your pro bono expenses for a non-charity, they will use the "Facts and Circumstances" test. They will look for: Did you have a reasonable expectation that this free work would lead to a paid contract, a referral, or a specific marketing advantage? Do you have a "contemporaneous record" (an email or memo) from the time you started the work explaining the business goal? The IRS will check to see if the "free work" was actually a disguised gift to a friend or associate. Under Section 274, business gifts are generally limited to $25 per person per year. If you can't prove a business purpose, they may reclassify your "expenses" as a non-deductible gift. @TuckerdogAVL