There were winners in the dot-com boom/bust. The problem is the wins always rush to the top, and nothing trickles down.
Nah. It's just like every previous innovation-driven boom (railroads, oil, telecoms...) the growth and buildout phase generates incredible new wealth, highly concentrated (Vanderbilt, Stanford, Rockefeller, Carnegie, etc.), . Then there are several decades of adaptation and adoption, during which the benefits accrue to the population broadly. This doesn't decrease the wealth of those who got crazy rich during the boom, but their wealth stops growing rapidly and they just become the new "old money". Then the next innovation creates a new crop of winners and the cycle repeats.
We're really just completing the adoption and adaptation phase of the personal computer revolution, and maybe a third of the way through the adoption and adaptation of the Internet revolution (the dot-com boom).
Growth halts and castes ossify.
This claim ignores the fact that each new boom creates an entirely new set of winners, nearly all of whom actually came from humble-to-moderate beginnings. The wealth isn't staying in one "ossified" caste, indeed it's the exact opposite of ossification. Of course, as I said above, the wealth of those winners doesn't decline during the adaptation phase, but the the wealth generated by the newly-realized productivity gains does accrue broadly -- and in fact those "winners" never actually had as much wealth as they appeared to, because their paper wealth was primarily composed of the market's projection of their slice of their company's slice of the broad future gains.
In the end, the tide does raise all boats. The US has been getting steadily wealthier -- at every quintile -- for decades. There have been some dips at each recession, but the trend line is clear. Look at the real median household income and the net worth of by the bottom 50%. Granted that inequality has risen... that's to be expected during and for the first decade or two after an innovation-driven economic boom, and we've had multiple, in quick succession. But the actual numbers show that the tide is lifting all boats -- though the boats of the big winners have rocket engines attached.
There is one very large caveat that we're dealing with right now, which is housing prices. Due to a combination of factors -- mostly dominated by increases in square footage per person and quality of amenities that we've become accustomed to accepting as the baseline, but also including excessive building restrictions and a minor real estate bubble caused by the pandemic and low interest rates, then compounded by rising interest rates needed to combat the post-pandemic inflation -- right now that increased income and wealth isn't enough for many to buy the homes they'd like. Wages continue rising and housing prices in much of the country are actually falling a little, so over the next few years that will likely equalize out, but right now it's painful for many. But that pain is generating a pessimistic view of the state of the economy and individual incomes that simply doesn't match reality.
There definitely is a risk right now that this could all go badly if the new winners are allowed to engage in extensive regulatory capture. That's how market-proof monopolies are built, by capturing and directing government power. If we can avoid that, though, and just let the market continue to work, the general wealth increase will continue.
Well, unless the AI singularity hits. It's impossible to know what things will look like on the other side of that.