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Re:Startup Restructuring 101 by rexreed on Saturday December 03, 2022 @11:38AM (#33844730)
I completely agree with your sentiment. I'm a bootstrapper at heart. However, I've dearly learned in the past few years that as a boostrapper, one of the biggest dangers is believing that markets seem real, when in fact, they are only being buoyed by puffery and hype. This causes a mistaken belief that there are customers and the market is indeed growing and significant for new entrants when what's actually happening is rapidly growing companies supported by investor money, not customers.

When a bootstrapper tries to come into the market and isn't playing the startup game, by trying to build a company through customer money vs. investor money, they see that there aren't nearly as many customers as they would like, and the hypey startups are eating up a significant portion of the customer base, since customers, far and few between in rapidly growing, hypey markets, tend to be "lazy" buyers and will not spend the time to do any sort of real evaluation or analysis of competition and markets. Rather, they will buy either from who they are already buying from, or if they will select a new vendor, it will be someone who is gaining the most attention at that moment and who they can get support. Ideally, if it costs nothing or very little to acquire, that makes it even easier. The latter makes it near impossible to support this as a bootstrapper, since you can't afford to give a product away, even if the startup can. All this makes bootstrapping particularly difficult in fast-growth, hypey markets, which is where startups tend to proliferate. You can bootstrap in more sedate markets, but you'll face entrenchment of incumbents even more the case and so making entry into the market as a bootstrapper just as difficult. The key is to know what game you're playing and the best way to win at it, if you want to succeed, especially without exhausting yourself in the process.

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