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If you are helping an entrepreneur raise money, there is no way you are going to avoid one or more “deep dive” meetings. Whether you are working with the company’s very first investors, or trying to build out the syndicate for a round, once a founder makes a successful pitch to an investor or group of investors, the next step is always more involved. Coming out of the pitch, most investors will ask to hold a longer more in-depth meeting to unpack the company’s story in greater detail. As most angels know, a lot of investors refer to this kind of meeting as a “deep dive meeting.”