YES! Absolutely go to multiple VCs in parallel.
I was fortunate to be an Entrepreneur in Residence (EIR) at a leading Bay Area VC.
I learned something very important: A VC will invest in one company for every 100 face-to-face meetings a partner takes.
The only fighting chance you have is pursuing multiple investors. My company was turned down 63 times before we received a term sheet.
And we were one of the lucky ones.
You, as an entrepreneur, don't know what drives a particular VC.
Here are some reasons a VC will not invest that has nothing to do with your company:
A. Fund life. It's easier to get an investment early in a fund's life. A typical VC fund has about a ten year life. VCs will actively invest in a fund for about the first five years. They will reserve the rest of the money for future investments in existing companies. Or...
B. The partner with domain knowledge in your area of expertise has already done multiple investments this year. He or she is tapped out for the year. You are out of luck. Or...
C. The fund is out of money. VCs need to raise money too. Sometimes they can't.
VCs will rarely tell you they can't raise money- it's bad for business. They will take the meeting with you, but you are out of luck. Or...
D. Bad experience with similar investments. Guilt by association. It happens all the time.
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