I should preface this entry by noting that I am neither a lawyer nor an accountant. Rather, I've spent plenty of money on the services of both, and I'm willing to share my recollection of some of the things I've learned along the way.
Failure, i.e., non-success, is one of the things to plan for in any entrepreneurial activity, and when raising an angel round, i.e., investment from accredited individual investors, it is possible to engineer the round so that the investors get some generous downside protection from the tax code. Specifically, Section 1244 allows investors who sell their stock at a loss to deduct the loss. Under certain assumptions about the financial circumstances of the individuals, that means that they will lose no more than 65% of their original investment, providing that investment is less than $50,000 if they're filing singly or $100,000 if they're filing jointly.
If you're planning an angel round, ensuring that the investors are eligible for Section 1244 treatment would be a good idea. The burden of proof for Section 1244 rests on the company, but those records (Board minutes, financials, tax forms, annual reports, state and federal filings) are things that you should be keeping anyway.











