Should Investors in the Same Round of Financing Ever Get Different Prices?

Of course they should.

There're various financial instruments enabling this very well. Simple question and Dave is totally right while Fred still lives in the past and ignores the basics of dealmaking.

The first and those who were quick in decision making should pay less than those who join later the same round. To join a full party is always a safer bet than being the first guest, so simple.

Investor's reputation/brand/name and their network are other key drivers to the prices.

There's one exception: when VCs know each other very well and brought themselves into the round/deal then their good relationship (and potential other deals running besides) will usually prevent different prices.

My opinion is that yes they should, because there is also non-monetary factor in what they bring in which is different (while all bucks are equal). This is not so pronounced with the VCs but try thinking about angels, i would accept way lower valuation on any product/company i will start from PG than from the wealthy guy next door who has no idea about what i will be doing.

Investor converting into the round at a discount is really an investor in the previous round, So both Dave and Fred are right The round should have one price for everyone to make it clean and simple But earlier investors converting should be thought of as earlier round participants

Working at a start up where multiple investors came into the same round at different valuations; so yes, they should, it makes sense as different people bring different things to the table.

A heavy duty well connected investor who is actively making connections and opening doors should get a better price than a bank whose involvement begins and ends with a term sheet.