A few months back, Kelsey and I went through and talked with a bunch of other founders and investors and pretty much came to this same conclusion. Yes, self-funding/bootstrapping is difficult, but if you can make it work, you get to keep control and lifestyle, without adding a ticking clock.
The default answer to “should I raise institutional money” is “no.” Most companies and founders aren't suited to those requirements, goals, and trade-offs. This isn't a value judgement. Few products can reach $500M ARR, and most founders prefer to be DHH than Bezos.
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