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I think for things like business chat, since the purchasers of the product are different from the users, and not completely aligned with them 1:1, VC-backed companies with the connections and credibility to said stakeholders may have a much easier go at getting paid users. You can also trade profitability for growth, which is something bootstrapping precludes.

P.S. I read @rwalling's "Start Small, Stay Small" a few months back, and it was a phenomenal read. Highly recommend.

Agreed! I think products where the purchaser and the user are different are an enormous graveyard for startups. There's a big difference between building a product and building a business no matter the sector. But when the purchaser and user are different, it can be way worse. Good designers and engineers want to focus on improving the user experience, but that may not translate into sales at all.

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