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E16 w/ Sahil Lavingia taking Gumroad off the VC treadmill, increasing pricing was very controversial but ultimately the right move

Second Time Founders

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Do You Think This Will Happen to Your Company?

I'm curious. Why do you think that these types of things don't happen a lot? So I had a similar type of thing that happened to me with ship. Our preference stack was 63 million dollars. It's hard work, but it's also impossible to really get done. Like investors would rather that something go to zero and for you to start over then trying to like clean up this mess.

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