They are often “unprofitable” exactly because they properly optimized their taxes.
At the extreme, no Hollywood production ever makes a profit, and they aren’t taxed. The tax people aren’t stupid, and the total tax paid is actually reasonable, but it is not paid by the entity that makes the movie, but rather by actors, marketing, filmmakers, etc. They get to minimize their tax to the absolute legal minimum, while at the same time advance their business goals (primarily, shaft whoever isn’t aware of these schemes - mostly newcomers to the business)
Roughly speaking, my experience tells me the percentage of founders (or aspiring founders) who obsess about such things is <10% and highly correlated with their proximity to MBAs.
Folks building products to solve problems for people are far more likely to do what they’re told is “normal/best practice”. At the other end of the spectrum 10% who do nothing and expect it to be “fine”.
That reads a bit cynical, but it isn’t intended to be — people choose different paths and how and if they work out is hugely varied. Each path has benefits and risks, and appeal and ugliness.
I’ve been a founder and know dozens of founders. Tax has never come up as a topic of conversation.
Primarily because companies are only taxed on profits. Most startups aren’t profitable and therefore pay no taxes (other than payroll taxes).
This is true even for public companies. 40%+ of S&P 500 companies are unprofitable.