Rison Simon built PainPointy to scan Reddit so that marketers could learn the pain points of their customers and come up with article ideas. The problem is he's never had more than six customers.

So he has to go interview customers and potential customers, which means first knowing what to ask them. We workshop that with my Iterative Hypothesis method — inventing the questions, then working out which ones are best.

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STARRING RISON SIMON
PainPointy
Blog
Substack
Twitter | LinkedIn

REFERENCED IN THIS EPISODE
The Iterative Hypothesis Method
AI skills that implement the Iterative Hypothesis Method

TIMESTAMPS

• (00:00) - He sold his last startup the week he launched it - this one has almost no customers
• (02:09) - What PainPointy actually does, and why Rison can't say who wants it
• (08:37) - The Iterative Hypothesis Method: write down what you think before you ask
• (14:19) - Why does it have to be B2B? Interrogating your own assumptions
• (19:08) - The question that doesn't lead the witness
• (28:33) - Quantity vs quality of leads: the customer who's actually easy to win
• (39:08) - The real problem isn't a shortage of ideas, it's knowing which one to pick
• (50:23) - Powers of 10: turning vague guesses into testable numbers
• (58:11) - Where to actually find people who will talk to you