Corporate expenses
I’m afraid it does not look good for you. To deduct the expense, you must show it is ordinary and necessary to your employment. The cases, I found held that similar situations were not ordinary and necessary. But this is by no means cut and dry. If you have a significant amount at stake, I suggest you hire a CPA to determine if this is deductible.
The case of Eugene F. Grossman v. Commissioner Docket No. 5565-70, 33 TCM 1213, TC Memo. 1974-269, Filed October 15, 1974 gives the general rule, and also the closest set of facts to yours that I could find:
The case of Deputy v. Dupont, 308 U. S. 488 (1940), enunciated the general principle that expenses of a corporation paid by a shareholder are not ordinary and necessary expenses of the shareholder, but rather ordinary and necessary expenses of the corporation. The decision in Dupont requires that the expenditures proximately result from the trade or business of the taxpayer in order to be deductible by him. The expenditures petitioner made on behalf of the corporation did not result from any business activity of his own but instead directly resulted from the business operation of Argentum itself. Although petitioner spent time on the affairs of the corporation and paid the corporation's expenses from his own funds, the expenses he paid were those of the corporation.
As for deducting the expense as an investment expense, the case provides: Under the provisions of section 212 (ivestment expense) as under those of section 162 (business expense), an expense to be deductible must be "ordinary and necessary" and "personal to the taxpayer" as well as "immediately related to his own income or property." Harry Kahn, 26 T. C. 273, 275 (1956). Bert B. Rand, 35 T. C. 956, 961 (1961).
