great article and discussion. lots of yc companies have gone this way -- we will probably as well. anyone have experience raising hundreds of k (in convertible debt) from multiple investors, or is it preferred to get that amount from only one or two?
There are pros and cons of each approach but in general I don't think the distinction is important.
Take whichever route is faster -- and you'll only be able to determine that once you're on the road. I think the pros and cons of either approach are probably a wash.
On one hand, it is more work to close and manage more investors who are each putting in small amounts. But it is also tougher for multiple investors to send a single coherent signal that influences your next round of financing negatively.
On the other hand, it is harder to get big checks from a few investors. But once they are sold, getting a bigger check may be better because they will be more likely to help since they are more invested.
