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some of my favorite people for the early stage “haven’t scaled well.” eg first sales folks, recruiters. they’re worth their weight in gold and are gluttons for punishment doing repeat early, high agency problem solving work. in the age of AI, maybe they get to do that at scale why does it usually break? they’re doers, but they don’t create systems to manage lots of people, or they don’t manage the communication complexity, and imperfect and indirect incentives of big companies well venture firms like to talk about hiring “stage specific leadership” I think this will evolve. seeing lots of SaaS execs struggle within the super high growth and velocity ai startups
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Library as of 2026-10-22