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Getting attention is the number one thing. I think the method he used worked quite well. I am not sure there would always be an opportunity like this.
hahahahaha this is great! useful / insightful and really funny story.
You should check out his book, Innovation Stack. It was a really good read.
Thought the name might be familiar, and yeah Jim McKelvey is the co-founder of Square. I'd say his blog is above average.
An ad-hoc sales tactic from 1993 that involves pretending to be a male stripper to get attention for your software product, might not be all that viable in 2020.