Was the latter VC-backed. How big was the company when you where there? Did the VC made money on that trade?
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The trainwrecks had initial pre-seed funding (mix of angels and VC) but fizzled out just before seed raising trying to find product/market fit in a far-too-novel niche, much too close to open source software.
The non-trainwreck: as far as I know, for the most part bootstrapped and profitable.
I'm not a super experienced expert in this field, but my spidey sense from observation and vibe-checking is that VC money is mostly a problem unless there is strong and focused alignment with the startup's "spiritual" mission. Which is probably almost always impossible for any of the products and technologies I'm interested in. Which is probably why I think VC money is almost always an anti-pattern in my world.
I'm certain there are whole books about this that I haven't read
Yeah, I almost don't call bootstrapped companies "startups" because they are more like regular small businesses than the crazy stuff we see with VC money. High ROI expectations, high levels of craziness.