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Why Startups Fail - 20 Top Reasons Gleaned from 32 Startup Failure Post-Mortems

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January 11th, 2011 the Chubby Team 34 Comments. We’d previously highlighted the top startup failure post-mortems of all-time here (32 in total) written by a group of startup entrepreneurs gracious enough to share their lessons learned from their startup’s failure. 11 – Pricing Issues. Investors Companies.