If you’re happy with paying a few maintainers, a support staff, and some salespeople the cash flow necessary for being a successful endeavor is a whole lot different than if you’ve raised $350 million.
Maybe the problem lies more with overreaching and trying to cash out?
For sure, there is a problem in startup culture that looks down upon lifestyle companies. Devtools and developer focused products often get caught up in this.
At the same time, founders take money to build their idea into something more than they could do with a small team. An big companies are risk averse, having a small staff or being susceptible to "hit by a bus" failure is often a deal breaker
That’s very true. Business is very much a balancing act in that sense. Sometimes raising money is the reason you succeed, but it can equally well be why you fail (especially if you’d be happy running a smaller company but take on investors that want you to be hungrier).
Maybe the problem lies more with overreaching and trying to cash out?