I am not a lawyer, so don't listen solely to me. No. 1) You shouldn't be giving up 60% in an angel round. 2) If the company is brand new, the shares should b

I am not a lawyer, so don't listen solely to me. No. 1) You shouldn't be giving up 60% in an angel round. 2) If the company is brand new, the shares should be worth essentially 0, which means you should be paying like $1 for them. 3) Your situation isn't entirely clear, but it seems that there is no taxable income here. You will have to pay capital gains taxes when you sell your shares, however. 4) If it is restricted stock (e.g. vesting), there is a tax issue. It is simple to deal with, however. Like others' have pointed out, you need to do a an 83(b) election. It is a simple one page thing, but you have to do it in a timely fashion. So look into it now. If you don't, you will get taxable income as your stock vests, which in most cases, is not what you want. The reason you don't want this is you will have to pay taxes on "phantom income," i.e. on taxable income that isn't associated with associated cash flow.