Fred Wilson (partner at USV and long-time blogger) had some good observations in his What will happen in 2023 blog post.
On the new fundraising environment (lower valuations and higher demands on startups to be funded) he writes:
“This new normal will lead to many flat rounds, down rounds, inside rounds, and rounds with a lot of structure on them. None of that is good, but the worst of those options is rounds with a lot of structure. I believe founders and CEOS and Boards should take the pain of a new valuation (flat, down, whatever) over structure.”
Structure (I interpret this as things like tougher terms in Shareholders agreement, additional approval rights, preferential options deals, additional board seats, aggressive preference rights etc) might feel better than a lower valuation initially for a founder, but I agree with Fred. If at all possible (enough money to execute the plan without excessive share dilution) it is better to go with a clean structure and a lower valuation than a complex structure and a slightly higher valuation.