Setup: X has cash, Y has an idea, experience and contacts and wants to work on this idea full-time. X wants to create a corporation with Y and contribute $100,000 for 50% of its equity. Everything happens in the US. Y wants to get 50% of stock of the newly formed company, but not to be taxed on the $50,000 "gain". In other words, can Y prevent IRS from making the case that he just got valueable stock without paying for it in cash or property?
Option 1: Y receives 50% of stock "for services provided" (and contributes no cash) and X gets remaining 50% of stock in exchange for $100k in cash (assume at the same time, at formation). Does Y immediately incur taxable gain of $50k?
Option 2: Same as before, but Y receives 50% of stock in consideration for "for services provided, valued at $50,000". Same question.
Option 3: Say there is 1 million shares authorized. Y gets 500k shares on day 1 at $0.0001 per share, paying $50 in cash. Since the company has no assets and is essentially worthless, Y records fair value of the stock as $50, and hence has no taxable gain. On day 2, X gets his 500k shares in exchange for $100,000 in cash, i.e. for $0.2 each, and records fair value of the stock acquired as $50,000 (50% of the company whose total assets are $100,000 in cash). Same question about taxation of Y's stock.
Options 1B, 2B, 3B: same as before, but instead of getting the stock as an individual, Y forms ABC, which is a single-member LLC. Say a month later ABC creates the corporation with X, as per respective option defined above. Does this LLC layer and the one-month gap between formation change tax implications?
Options 1C, 2C, 3C: same as 1B-3B, but instead of a corporation, ABC creates a 50/50 JV with X. Again X contributes only cash, and ABC contributes only "services". JV's total assets will be $100k, and ABC (and hence Y) will now have a gain. Is this a capital gain? When will Y get a tax bill for it?
Any other option(s) that would allow Y to optimize his taxes? If instead of "services" Y contributes "intellectual property" (with plausible description of say his business concept), valued at $50,000, does that change anything?
Thank you, really appreciate any advice here.