Investor Ben Black passed on MongoDB after CIOs criticized its security and scalability, favoring DataStax. However, developers loved MongoDB, driving its massive success. This proves that end-user passion can be a more powerful indicator of future success than immediate enterprise-readiness concerns from executive buyers.
An investor with a small $80M fund regrets picking just one database company (DataStax) and passing on its competitor (MongoDB). He now believes when a category is clearly going to be large, the correct strategy—even for a small fund—is to invest in multiple leading players rather than risk missing the breakout winner entirely.
Maveron's Natalie Dillon met Whatnot's founder early and had a strong thesis on the space, but as a senior associate, she talked herself out of it. She deeply regrets not trusting her instincts and pushing harder internally. This highlights the critical internal barrier of self-doubt that junior investors must overcome to back their conviction.
Larry Cheng met Mark Zuckerberg and Eduardo Saverin when Facebook had only 6,000 users at Harvard. His firm's investment committee passed because they couldn't get comfortable investing in a college sophomore. This demonstrates the institutional bias against young, non-traditional founders, even when they are building something with high engagement.