... and that's precisely the problem - what should be a more or less free market (admittedly with some advantages for people who have more access to more money, such as those with rich relatives, lots of savings etc) ends up so badly distorted by the willingness of some investors to pump unimaginable amounts of money into business so they can lose money at terrifying rates, with little more than a hope that it will turn around and start making money before the losses become too big to ignore.
I'm not sure I can agree with you, here. Investors should be free (as in,
free market) to invest in whatever lawful enterprise they wish. I believe a genuinely free market will be robust enough to heal itself from any such momentary aberrations.
Along the way entire industries are disrupted in ways that destroy the benefits that proper capitalism should bring - for example when technology companies exist to develop something not to offer it to the market and hope to make some money by meeting consumer needs or wants but in the hope that sooner or later they'll be able to sell out to Google or Microsoft or Facebook or similar all that happens is that resources are tied up producing nothing of any value, and all the while the smaller operators are squeezed out of existence. It's hard to compete when your competitors have a willingness to take unlimited losses because they have unimaginably deep pockets, or when you're trying to hire good employees but the best ones have been snapped up by a company that offers little more than a long-term hope of instant riches triggered by a successful IPO.
It might be hard to compete, but that's entrepreneur-ship in general. For every story like what you've outlined here, you can also bring up a story of some small company that produces something wildly successful, far better than the big company like Google or Microsoft, and then sells out at an outrageous profit. E.g., though I'm not sure I'm in favor of genuine monopolies, Rockefeller Oil got taken advantage of countless times by small-timers starting up an oil business and then selling to Rockefeller for huge profits.
Under a truly free market a company that can't make a profit goes out of business sooner or later. I think I would agree with the concept that a company deemed "too big to fail" is too big to exist.
It's quite interesting to compare the Fortune 100 companies of 1980 or even 1990 with the Fortune 100 companies of today. How much overlap is there? I would argue that the phrase "too big to fail" doesn't mean much. Any company can fail. Google and Facebook, with their ultra-progressive biases, are going to have problems someday, as the ultra-progressive worldview is not grounded in reality.