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I don't understand how DocuSign was $50B while Dropbox was $10B; the barrier of entry is even lower for DocuSign and Dropbox even has a competing product
Dropbox has a competing product that literally nobody uses. Supposedly HelloSign is a distant 4th place in a market with 4 participants, having a market share 100 times smaller than DocuSign. That seems to be the difference! If DocuSign was worth $50b then HelloSign is worth at most $500m.