First - founders should always be on a vesting schedule, just like everyone else. This schedule should be laid out in the founder's agreement. This isn't for t

First - founders should always be on a vesting schedule, just like everyone else. This schedule should be laid out in the founder's agreement. This isn't for tax reasons but in the case you have multiple founders and one of them leaves. Second: giving 60% to an Angel investor is way too much, but I presume you picked a random number as an example. If you plan to raise a larger round later (from a VC etc), you should get a convertible note, where the Angel doesn't get a set amount of shares but rather the right to convert the note into $(amt invested) * (discount rate) at the time of the next round. Third: Yes, you need to pay taxes on your stock as it vests. You should talk to your attorney about what's called the 83(b) option to mitigate this tax liability. Given that your stock is worth very little you should have minimal liability. Fourth: I presume you just stated this scenario as a hypothetical and you haven't actually started a company and done this, much for the above reasons and what other comments have said. Do your advisors have experience launching/guiding a successful startup company before?