Deconstructor of Fun · 5 October 2026 · Operating Insight

Why Great Hires Fail at Startups.

Deconstructor of Fun

Great talent from established companies often fails at startups not due to lack of ability, but because they lack grit and humility to adapt to an environment without scaffolding, process, or clear hierarchy. Garry Hill, who has conducted 20,000+ interviews across major tech companies and now advises 130+ portfolio companies, shares frameworks for identifying who actually fits startup stages and how founders should think about hiring, culture, and succession.

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Topics: Venture Capital & Startups · HR & Talent

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