More Reasons Not to Invest in Notes

Way back when, I was happy to have encountered Josh Kopelman’s excellent post, Bridge Loans vs. Preferred Equity, to which I did sort of a re-post but also added my spin on the subject in Convertible Notes versus Preferred Equity Parts 1, 1.5, 2, and 3.
Now that I’ve been out here for about two years angel investing, I’ve uncovered more reasons not to do notes any more. So much to learn but yet no one to learn from except to fumble about and get myself into trouble. Now I’ve firmed up my rule to never invest in notes. I *might* do a note with a price cap on it, but it is still not without potential future issues. Here are some more reasons why notes are awful:
1. It is possible that the company you invested in achieves significant revenue, enough to do one or both things:
a. The valuation will inevitably jump. So when you put in your money, you expected the valuation to be one value, but when your note converts, the valuation has gone higher and now you’ve taken all the early risk with your note investment, but have lost share in the company upon conversion.
b. The company has enough revenue that it may not need further investment. Or it can delay seeking investment. If the company does not need further investment, then you’re in risk of just getting paid back and not obtain any share of the company. This can also happen if the delay in seeking further investment takes the next fund raise period out beyond when the note is due. Again, you could just get paid back instead of converting into equity.
It is possible to convert still, even if there is no conversion. But it depends on the entrepreneur and they are under no legal obligation to do so.
2. The valuation may jump anyways independent of revenue. Again, if/when you convert, the value of your participation will shift from where you originally put in the money, and it doesn’t reflect the risk of your early investment.
3. The terms of the next equity financing are unknown to you at the point you invest. While it is easy to ignore this in the excitement of doing an investment into a note, any problems that may arise will come up later during the conversion process.
You would think that at conversion time some large and/or experienced investor would take care of negotiating the proper terms. In most cases, this is true. However, it is also possible that not-so-favorable terms may appear and seem to be proposed by seemingly experienced investors. The big issue is that you don’t know what you’re converting to with a note at the time you give up your money; then, if you don’t like the terms, you’re kind of stuck into accepting them because you can’t get your money back. Unless you’re leading the investment, you won’t be able to affect them much. However, if you do get stuck in one of these situations, I would advise you to speak up about the terms; you never know when you’ll be heard and someone might actually change the terms to your liking.
Notes don’t align investors and entrepreneurs, and now I’ve discovered other reasons not to do notes…