For my generation it was ‘why didn’t I buy shares in Google/apple?’ And the answer is that at the time there really was nothing in particular to indicate they’d do as well as they did.
Apple, in particular, was climbing out of a hole it had dug for itself in the 1980s. There's no particular reason to believe it should be valued higher than Microsoft, a company that's got a functional monopoly on computer OS into perpetuity.
Google's position as Ad Titan was entrenched half a decade ago, but it only really showed up in the stock price after the pandemic struck (and even then, the stock's swung from $1.5k/share to $1k/share to $2k/share in less than a year - hardly the basis for long-term faith in the company).
And even setting aside "Coulda/Shoulda/Woulda", it's worth noting how your benefit in playing the markets was predicated on your accrued savings to date. Back when Las Vegas crashed, during the '08 Great Recession, I felt very clever when I realized Las Vegas Sands was trading all the way down at $2/share off it's $50 peak, and that this was comically undervalued. I bought up a thousand dollars worth of shares. And when the price bounced back up to $10/share, I sold it confident that I'd made an incredibly savvy choice. But turning $1000 into $5000 over six months didn't bring me anywhere nearer to the kind of perpetual income security enjoyed by... say... Sheldon Adelson or Steven Wynn.
Without access to the Infinite Money Spigot of Wall Street Finance, all my genius netted me was a position a few steps farther away from abject poverty than when I started. I was never going to net enough to retire early on given the amount of money I was willing to risk. And that's assuming every investment was as good as LVS. I've lost a fair chunk betting the wrong way, too.
Also, plus, too. For everyone who tells you "Bitcoin was a good investment", ask them what happened to Mt.Gox.
Apple, in particular, was climbing out of a hole it had dug for itself in the 1980s. There's no particular reason to believe it should be valued higher than Microsoft, a company that's got a functional monopoly on computer OS into perpetuity.
Google's position as Ad Titan was entrenched half a decade ago, but it only really showed up in the stock price after the pandemic struck (and even then, the stock's swung from $1.5k/share to $1k/share to $2k/share in less than a year - hardly the basis for long-term faith in the company).
And even setting aside "Coulda/Shoulda/Woulda", it's worth noting how your benefit in playing the markets was predicated on your accrued savings to date. Back when Las Vegas crashed, during the '08 Great Recession, I felt very clever when I realized Las Vegas Sands was trading all the way down at $2/share off it's $50 peak, and that this was comically undervalued. I bought up a thousand dollars worth of shares. And when the price bounced back up to $10/share, I sold it confident that I'd made an incredibly savvy choice. But turning $1000 into $5000 over six months didn't bring me anywhere nearer to the kind of perpetual income security enjoyed by... say... Sheldon Adelson or Steven Wynn.
Without access to the Infinite Money Spigot of Wall Street Finance, all my genius netted me was a position a few steps farther away from abject poverty than when I started. I was never going to net enough to retire early on given the amount of money I was willing to risk. And that's assuming every investment was as good as LVS. I've lost a fair chunk betting the wrong way, too.
Also, plus, too. For everyone who tells you "Bitcoin was a good investment", ask them what happened to Mt.Gox.