I have found that my best pitches were less of a “pitch” and more of a “conversation”. These more conversational pitches have tended to be during lunch or at the end of the day (especially on Friday). My experience here may be an outlier, but during these more conversational pitches, I was able to successfully get the investor to like me (first) and then like the company (second). By being outside of the constraints of a one hour time limit (end of day) or at a lunch hour (when people are more conversational), I have tended to be the most successful.
Other Tips to Improve Your Odds:
Try not to pitch by phone
The odds are stacked against you over the phone as an investor is likely multitasking. It is also difficult to truly have the connection you can achieve with an in person meeting. In many cases, traveling long distances may not make sense, but know the odds are stacked against you over the phone.
Try to pitch a decision maker
The odds are extremely stacked against you when you pitch an associate. Associates are even more risk averse than partners. They would rather be wrong and pass on a good deal than recommend a deal that doesn’t look perfect to the partnership. Odds are, your startup will fail…and therefore an associate’s default is to pass with any sliver of doubt. Additionally, associates generally don’t have the track record, experience, gut, clout to spot and push a good deal through. They will need to go through others in the firm to get a deal through (who haven’t met you) and your chances will most likely be diminished significantly. Think of it as a steel gate in front of a steel gate that you will need to plow through on a tricycle. One gate is a pain in the ass. Two gates…well you have the idea. You probably gathered it makes more sense to pitch a partner (with the highest authority possible) who has the highest likelihood of falling in love with you/your company).
Get them to like you first
Forget your company…if the investor doesn’t like you (which they can probably determine within the first 60 seconds), they will figure out a way to pass on your company. Remember, the investor, if they move forward with an investment, will have to deal with you for 5+ years of their life. Make them want to spend that time with you….then convince them that you will bring home the $ Billions…
Now for the gratuitous shot of the Maltese Falcon: