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Sometimes, given your syndicate configuration, you have no choice but to take structure in a new round. Rather, when you have a choice between a financing at a lower valuation and a financing with all kinds of crazy structure to try to maintain a previous valuation, negotiate the best price you can but do a clean financing with no structure.
Yes, there are a number of cases in the middle where having a senior or participatingpreference does make a difference in liquidation proceeds, but I argue that it does very little to overall returns in a diversified portfolio. AngelList (which I remain a big fan) also recently launched a syndicate program.
In fact, in this new fundraising environment (with syndicates on AngelList , etc.), The goal is to get one of these investors to be your “lead” or “anchor” (the one putting in the most money), who will take ownership of the deal and be there during thick and thin. your lead may be able to make the deal happen very quickly.
I can just picture Mr. Rogers saying "Children, can you say participatingpreferred stock with an uncapped 3x liquidation preference and a full ratchet?" When AngelList first launched syndicates a few years ago, I was very skeptical of the idea of angels taking carry on my investment. I got over it.
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