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One of the things that helps the most, it seems to me, is having the self-confidence to take the risk. You also have to be motivated enough and in good enough health (eg: not burnt out) to be able to work on this side-project after your job. Then of course you need the right skills, the right timing, and the free time and financial resources to execute your plan.

However, at the end of the day, you are taking a risk, it's a gamble. What stops most people is the fear of failure. This fear isn't necessarily unwarranted. As the author points out, he has a previous failed startup. Most people don't have the drive to work hundreds of hours after work and possibly invest their own hard earned cash in a project they suspect deep down might not actually pan out. I know I find it difficult.

Still, I don't dislike these stories. It's good if it inspires people to take (calculated) risks, and it is possible to learn from failures. Though I would also say that yeah, there's probably some self-selection going on. The people out there with 2 or 3 failed attempts at monetizing side-projects probably don't feel super eager to write a blog post and tell us all how we can improve our lives by following in their footsteps.

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