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If anyone is looking for a blog post writing prompt, I would love to see something written from a founder's perspective breaking down when one should consider this form of funding, vs. YC/VC, vs. "grinding it out" and continuing to bootstrap. Or taking personal loans, etc. This could include some analysis of the total cost of each option, the benefits, etc. Specify numbers about you should use X amount to pay your own salary, Y to hire people, Z for marketing/other spend, etc.

I think the YC/VC pre-market-fit-hoping-for-billions model is well understood. But I find it difficult to understand when a bootstrapped cashflow positive business should consider any of these options. If one has a bootstrapped side business making $X/mo and a job making $150k+Y per month, when should one go all in on the business?



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