Should Wikipedia run ads that ask for money, or ads that make money?

I don't know what the answer is for wikipedia. But I do know that I use dictionary.com less frequently because of the ads.

An extreme example of how far this goes was the Apple iPad ad that ran on yahoo.com a week or so ago. It WAS the upper fold of the front page. Fixed in place at 974px by 500px just below the search bar and logo. Bam. Here I am. Buy me now. No doubt paid some bills but made me think "this organization has a price."

My impression is wikipedia values the way users interact with its content and would rather not introduce distractions.

Both, ads that make money while asking for money.

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Wikipedia competes with other companies not just on market share and money, but even more on attention from people actively supporting it by editing the information. I see no immediate gain they could get in market share by making money with ads as they are already having the biggest share of any encyclopedia with their current way of working. But I'm rather certain they would lose a lot of editors and would even give a competitor a chance to gain those people. As little as many people might care about seeing Google-ads, no one helps Google for free. Swarm driven websites have to care about attention from people far more than about money as long as they are able to cover their costs (and they are able to do that as long as they have the swarm behind them).

Craigslist does have 'ads', of a sort: all postings in certain categories, in certain markets, require a posting fee.

I think Craiglist, while not a non-profit, is actually a very good model for the path Wikipedia chose not to take. That is, don't just accept the default ad-inserts, but figure out a unique way to charge for promotional inserts that is complementary to your main model. (The fees actually make Craigslist better, by filtering the volume/quality of posts in certain economically-valuable categories.)

Mozilla, a non-profit, is another example. The search-engine-default that they sell is now making them $300 million a year, but at negligible cost to their users (compared to the alternative of giving that placement away, via some hypothetical revenue-oblivious process of evaluation or install-time-choice).

Once upon a time, Wikipedia could have kicked off an effort to find a promotional-placement model that was unique to Wikipedia, and considerate of concerns about the influences of commerce and advertising budgets.

I think such an effort would have yielded interesting and beneficial results: if any organization had a chance to find a way to balance concerns and insulate editorial processes, Wikipedia had a chance. And today they might be a $billion-a-year budget nonprofit instead of a $40million-a-year budget nonprofit. (That would introduce plenty of other existential risks and opportunities different from their current focus.)

But, they went another way, based on some really strong preferences from a large and important segment of the stakeholders. And, that path has still worked very well for Wikipedia. The idea that "no advertising" is a necessary part of the recipe is now core doctrine, and can't easily be reevaluated. It would take a major crisis or external challenge to change; in the meantime these discussions are just interesting thought experiments.

I wish they had an opt-in ad program so people who don't want to donate can still help.