Tell HN: Company returned 3X, but I (investor) may lose money

[US Tax Payer here]

I invested X into the company, with a post-money valuation of Y (a minor investor). The company was bought for 3Y. Sounds good, right?

However, the deal was structured such that 1Y was paid in cash, and 2Y was paid in stock of the buying company. (1X and 2X is my respective share of the deal)

So, I got my cash back; the 2X is considered immediate ordinary income, taxed at 35% federal + 13% NYC. So, I'm 48% down on the 2X already.

Enter SEC rule 144 - I'm not allowed to sell these in the first 6 months. That might have been ok, if the buying company didn't go down some 40% since then.

So, I'm still more than break even, but not a lot more. If the company goes down (in total) more than 52% in those 6 months, I'm going to be losing money on a successful investment.

Thanks to US security and tax laws.