Over the course of my career as a VC I’ve been involved with a bunch of fundraising. Raising money for our fund. Raising money for our portfolio companies. Advising friends on their fundraising. Lots. Of. Fundraising.

Some of that fundraising has been very successful. Some less successful. And some has been an absolute disaster.

Of the raises that have fallen into the latter category I’ve seen a common theme. At some point in the process, the investigating VC asks the question aloud “how big can this get”. The question itself is not the issues; rather, it’s how long that question persists and festers throughout the ensuing funding conversations.

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