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McNairn: Identify AI market niches by studying pre-AI software categories

Ross McNairn · He grew to millions in ARR in 18 months—by fighting with his co-founders on purpose. | Ross McNai... · PMF Show · Aug 14, 2025 · at 31:19

Ross McNairn, founder and CEO of Wordsmith AI, explains how founders can find defensible vertical software opportunities within broad AI waves.

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“One way to help work out what that clustering could be is to look at what products, what clustering there was pre AI. So in our space, there used to be a big split in technologies between in-house and law firms, right? So that was two years ago. You had the CLMs, the DMSs, and that's because, guess what? Even pre-AI, they have hugely different requirements.”

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