"Why don't the poor just buy more money?" and other examples of cheerleader capitalism

The article's not really focused on providing a path to financial security or "buying future cash flow", because there is no future cash flow one can just buy. It's just explaining a cartoon story of small-business capitalism that some capitalists occasionally make work for them. The majority do not. All businesses carry huge amounts of risk, far more than selling labor for money. In fact, that's the common explanation for why capital gets outsized returns while labor hasn't gotten a real-dollars pay raise since the end of the 70s. Capitalists take on the risk premium.

This is also why investments cannot usually be sold to the average retail investor without a huge amount of bureaucracy: it's far easier to scam investors than to actually provide a business worth investing in. Even then, we see all sorts of scams anyway, because the Internet has pulled the wool over the eyes of the notoriously underfunded SEC and thus we let "innovation" and "blockchain" obfuscate otherwise obvious Ponzi schemes.

For just the example of "buying an established website" - how do you know what websites are "established" and worth buying? How do you know that the person you're buying the website from isn't inflating their ad revenues with click fraud or black-hat SEO tricks that Google or Facebook will detect and ban next month? How do you know that the website won't see a huge traffic decline when Google deploys a new algorithm update and all the carefully-designed SEO suddenly becomes a huge negative signal on your site? All of these are risk factors that you have to actually specialize in a particular subset of web design in order to understand and mitigate. At that point you are back to just selling your time for money, but with more risk.

Okay, let's take the vending machine. Where the hell are you putting this vending machine? Do you just put it in front of your house? No, you have to find a high-traffic area, which will almost certainly have an owner that you'll need to pay rents to. And they will know more about how much money your vending machine makes than you will, so they'll be charging rents calculated to reach deep into your own pocket so that your margins will be as slim as possible. Not to mention your suppliers will also be looking to scrape away your margins, too.

Beach condo - okay, sure, you got me here. Real estate is a pretty good investment, at least when you have someone to rent to. This is mostly because of stupid political decisions the US made that has resulted in everyone's home becoming their retirement financing vehicle. We can't let housing costs fall, because that means angry Americans can't retire, so the government props housing prices up with restrictive zoning. However, that's not really smart business decisions, that's just taking advantage of the government - and eventually anyone who isn't in on the scam is going to demand free housing. You can't make housing expensive forever.

401k/IRA - Not a bad option, especially if you index fund it. However, you put this into the "guy who just buys fancy things" column, so I won't count it as a business idea.