5 > 20 is a walk through the park
20 > 100 takes a toil, planning and lot of effort
100 > 500 the founding team members are going to be clueless and over stretched
While a great team culture can be instilled from the early days and with enough momentum will carry through the middle growth, do not assume it will carry through amongst hundreds without intentional team / org design.
Loving how Henry Shi is able to expand the pain or either start-up growth or corporate M&A's.
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