six interviews and everyone said "interesting" - is that a no or do i need more calls

Stop asking about the idea. Ask about the last time they did the thing.

Walk me through the last month-end close. What did you open first, what took longest, what did you have to redo. Then stop talking. If they cannot remember the details, it is not painful enough to be a business. If they can, you will hear the workaround out loud, and the workaround is always the same shape: a spreadsheet with someone's initials in the filename, a macro a former employee wrote, a Sunday evening.

The two questions that actually predict money for me are what are you paying for today that touches this, and who else has tried to sell you something for it. People with a budget line already have opinions about vendors. People with no budget line say interesting.

Just went through this and the thing that unstuck me was recording the calls with permission and then reading the transcripts instead of my notes. My notes were full of my own words. The transcripts were full of theirs.

I pasted all six into one document and highlighted every phrase that repeated. End of month came up eleven times across four calls and it always had a date attached, the 5th, the 8th. That turned into the whole product, because it meant the tool has to be useful inside a three day window rather than continuously. I would never have got that from my notes, which said wants reporting.

Politely disagreeing with the do-more-interviews answers. Interviews have a ceiling and you hit it around call eight. What you are missing is not information, it is an ask.

Interesting is the sound a call makes when nothing was requested. End the next one with something small and real: an introduction to one colleague, a twenty minute session next week where they bring their actual file, a place on a paid pilot. Any of those is a decision. Six people declining a twenty minute follow-up tells you more than sixteen more calls will.

My rule is the third call in a row that teaches me nothing new. That has landed somewhere between eight and fourteen calls every time, per segment. Six is not a pattern, six is anecdotes.

Things I count while doing them: how many describe the same workaround without being prompted, how many volunteer to be first, how many send me a screenshot or a copy of their actual file without being asked. Four of twelve describing the same workaround is a signal. One of twelve is a person. The unprompted file is the strongest predictor I have - someone who emails you their messy spreadsheet at 9pm has already decided you are solving their problem.

Nobody says no to your face. The only no you can trust is an unaccepted calendar invite or a declined card. Book seven more and end each one with a request.