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When did Gumroad hit a turning point?

It's important to understand that most software-companies follow a power-law distribution, where a small number of users does so much volume, revenue coming from their accounts ends up paying for everyone else. Getting this customers requires the company to spend insignificant time on each, but when successful, it pays pack many-fold.

When Gumroad failed to raise Series B, they could not afford to have sales team anymore, and they could not build all of the features anymore, but that actually helped them grow. Instead of focusing on whales, Sahil was now able to focus on customers who legitimately loved and used his software to start their businesses.

Being a self-service platform, they could no longer support all the big accounts, but they could spend time helping millions of people who were just getting started.