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Why did Gumroad struggle to raise Series B?

Investors are money-managers, and they have a job to create returns for their portfolio. Those returns are tied to massive wins on companies like Uber, and Slack, and Pinterest.

A good business, growing 7% a year and trying to raise a Series B, like it was in the case of Gumroad, is not interesting to them. Investors want outliers. A company that has great predictable numbers, but isn't growing fast enough, is less appealing than a company that is growing astronomically fast, but might crash and burn on ascend.