I think there are some great thoughts in this piece from Andreessen Horowitz. It’s best summarized by the following approach:

Whenever you’re raising capital, think about constructing the round in such a way that you’re strongly positioned for the future. This means raise enough money to put the company in a strong position to achieve the necessary operational and financial milestones and maximize the probability of raising future capital — even if you don’t think you’ll need to.

And while its great to keep pushing for higher and higher valuations, one big impact being that it keeps your dilution low (you give away less equity in your company for a larger chunk of cash), that can drive further complications.

In some cases, investors are more flexible on the valuation, only to demand being able to set the terms of the investment. If you’re ever been through the entire life cycle of a startup, you will appreciate how huge an impact the terms really do have on the amount of money you walk away with at the end.

This piece goes through a top level encyclopaedia of terms that you absolutely need to be aware of.

Read the full piece here.