When you are bootstrapping, there is that feeling of constantly being bogged down by the month to month cash flow situation. You know what I mean right?
One of the reasons for startups fundraising is to liquidate a part of the overall asset so that you can think long. The ability to be able to think long - at least in 12-18 month timelines rather than month to month - is the luxury that venture-funded startups get.
The first step then is to create an asset (before you can sell a part of it).
That, to me seems to be the logical goal of bootstrapping - and it would lead you to an option where you can raise capital if you want to aim higher or continue the current trajectory - where overtime cash flow would streamline, but there are no moonshots.
Logically speaking, when you are bootstrapping, you are using very limited resources to create escape velocity. Any mistake you make can be very dangerous and there are seldom second chances for any big moves. So it's usually a series of small moves, leveraging compounding.
Once you escape gravity - you are still in low orbit and you can feel that constant pull. Whether you want to remain a satellite or plot a course to the stars, is the next logical decision to make.
For a team that succeeds only by discipline, and a series of small moves till then, it is a character breaking moment, when you need to make a big decision. But it is a decision that still needs to be made.
There are several amazing startups that come up with the bootstrapping route and are trailblazers, but if you simply can't let go and make the transition, they become like a low orbit satellite - they are valuable assets to the ecosystem, but after a few years they lose momentum or retire.
I wouldn't want you to mistake me; It is a 1 in 100 skill to be able to break escape velocity. And some do it for the experience so that the next attempt can be venture-funded but with the discipline of a bootstrapped team, and this time plot a course to the stars.
Either Way, it seems that there are two options, and one indecisive path - and there is a choice to be made.
 The exception here is those extremely rare exceptions where you have managed to build a ludicrously high margin business, with very little to no CAPEX or OPEX and can plot a course to the stars yourself, with no need for outside help.
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