Mike Linksvayer has a fairly good argument that raising X dollars by running ads on Wikipedia won’t create more conflict of interest than raising X dollars some other way.
But the amount of money an organization handles has important effects on its behavior that are somewhat independent of the source of the money, and the purpose of ads seems to be to drastically increase the money that they raise.
I can’t provide a single example that provides compelling evidence in isolation, but I think that looking at a broad range of organizations with $100 million revenues versus a broad range of organizations that are run by volunteers who only raise enough money to pay for hardware costs, I see signs of big differences in the attitudes of the people in charge.
Wealthy organizations tend to attract people who want (or corrupt people into wanting) job security or revenue maximization, whereas low-budget volunteer organizations tend to be run by people motivated by reputation. If reputational motivations have worked rather well for an organization (as I suspect the have for Wikipedia), we should be cautious about replacing those with financial incentives.
It’s possible that the Wikimedia Foundation could spend hundreds of millions of dollars wisely on charity, but the track record of large foundations does not suggest that should be the default expectation.
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