Without question, for me the worst part of being an investor is having to tell smart people "no" on such a frequent basis.
Have been fundraising for the past few weeks, and have had a few no’s. Best ways I’ve heard it done: “Regardless, we’ll be cheering you on from the sideline” and “hopefully I’ll be adding you to my woulda coulda shoulda list in the near future” Easier and kinder.
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There are very few no's that I've said as an investor that couldn't become yes's down the line if fundamental things about the business change. It's better to keep the relationship open, even if you just think the person (not the co) will go on to do bigger and better things.
End of conversation
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