Out of 40 messages, 38 replied and agreed to a phone call, and none of them actually asked for the money.
[0] https://mtlynch.io/notes/designing-the-ideal-bootstrapped-bu...
I have run cold outbound to senior buyers for about twenty-five years, people who owe me nothing and get pitched daily.
Two things that I find move the reply rate more than anything else:
- First, a specific, bounded ask that names the twenty minutes and the exact question, so they can price the interaction in their head in one read. The article's "so short as to be unsummarizable" line is the same concept.
- Second, and this is the one people skip, evidence that you already know the answer to the easy version of your question, so the only thing left to ask them is the part that needs their judgement.
Offering to pay is a cruder version of both. It says the cost is real to you and you have thought about theirs.
The ones that land make the money almost incidental, the way Cohen's did. Make the ask cheap enough that saying yes costs them less than saying no.
Give them your answer to the easy version first, so the only thing left to ask is their judgement on the hard part. People will spend that on a problem they already feel daily, far sooner than they will do your thinking for you.