Epistemic Status
I now don't endorse this post in its current form anymore. It's not as charitable as it should be, and I didn't engage enough with the content of the previous prize. There is still something here about the sad state of the internet, and how maintenance is undervalued, but it'll take me a lot more traversal down the argument tree to get to the true problem.
Rant (potentially fueled by jealousy (I still believe it's true though)), for another perspective check this comment. I contacted Nick Whitaker per email for comments on 2022-04-19, but didn't get a reply.
Written ironically quickly, eternally incomplete.
Recently, the Ideas Project announced a $500,000 prize for new blogs.
The prize will award an up to $100,000 prize each to the five best recent blogs, in order to encourage the discussions around effective altruism and related topics. Blogs need to be public, generally concerned with effective altruism and longtermism, and should have been started within the last 12 months.
I believe that this prize is flawed in some subtle and not-so-subtle ways, which I first lay out, and then propose some alternative prizes which solve some of the underlying issues.
Critique
‘Blog posts’ might be the answer. But I have read blogs for many years and most blog posts are the triumph of the hare over the tortoise. They are meant to be read by a few people on a weekday in 2004 and never again, and are quickly abandoned—and perhaps as Assange says, not a moment too soon. (But isn’t that sad? Isn’t it a terrible ROI for one’s time?) On the other hand, the best blogs always seem to be building something: they are rough drafts—works in progress¹⁵. So I did not wish to write a blog. Then what? More than just “evergreen content”, what would constitute Long Content as opposed to the existing culture of Short Content? How does one live in a Long Now sort of way?¹⁶
— Gwern Branwen, “About This Website”, 2021
Blogs Are Short Content
Except for rare exceptions (Slate Star Codex being the most notable one), blogs usually don't provide much long-term value—who cares enough to read the whole archive of a blog, unless the author is exceptionally skilled? Even in the case of Scott Alexander, additional effort had to be made to curate the best posts and order them by topic, something still sorely missing for blogs like Overcoming Bias and Marginal Revolution or econlog. How much value is provided by reading the whole Marginal Revolution archives or all posts Robin Hanson has ever written? A lot, probably, but with extremely low value per post (compare to a post by Gwern, such as the one on spaced repetition—comprehensive, up-to-date, all in one place; built up over 10 years). I should know, I started reading the Marginal Revolution archives and quickly abandoned the endeavour, I persisted a bit longer with Overcoming Bias, reading at least all posts from 2006 and half of the posts from 2007.
Additionally, blogs fall prey to bit rot, in which facts fall out of date, replication crises happen, new relevant ideas are discovered, better citations become available &c; they also incentivize a focus on new posts (most blogs show posts chronologically by default, burying old ones in hard-to-navigate archives or with obscure tagging systems). (Similar with software projects: unmaintained software is worth less and less over time, especially when it is far down the technology stack; the shiny new JavaScript framework is the most popular, even if jQuery would do the trick ust as well).
What advantage, if any, do blogs have over other media? Books can be (and usually are) far more comprehensive and high-status, instant messaging and social media are more engaging, but move from one fashionable topic onto another, and imageboards—well, we don't talk about imageboards here. Blogs (or, in the best case, sites), allow for content to be accumulated slowly, and still stay up to date, connecting a larger network of ideas from a single person (in ways that wikis usually don't).
As with software projects, the first 80% of the work is finding the idea and doing the work to have a basic prototype, the second 80% are writing clearer explanations with images, citing the claims, updating the text with new facts or arguments after they come out, and perhaps completely rewriting it after it has turned out to be wrong.
Did Anybody Think About The Incentives?
We can then look at the prize from another lens: Which algorithms' measures does this prize increase? Surely not the one of people who are willing to put in a decade into a post about spaced repetition, since one of the requirements is that the blog should have been started at most 12 months ago (‽), so the algorithms you incentivize is not “puts a lot of effort into a blog”, but “puts a lot of effort into a blog as long as there is a juicy prize at the finish line”. (The website states that only blogs started "within the last 12 months" are eligible for the prize—does that refer to the 12 months before the announcement of the prize, or the date at which the prize is given out?)
Of the blogs that will win the prizes, how many of them will persist after the prize is given out? Not many, I reckon.
Rewarding this kind of unmaintained one-shot content creates not epistemic infrastructure (posts that come to fruition slowly, that potentially will still be read in five years), but epistemic fireworks (or, in the best case, epistemic tinder that sparks discussions).
Long-Term Prizes for New Blogs
This would be okay if it were a prize for blogs about current event or news, but the website states that the blogs in question should "explore themes related to effective altruism and longtermism" and that the Effective Ideas team has "a particular interest in iconic blog posts that stand the test of time."
That, of course, makes perfect sense: You'd obviously like to exclude anyone who has put any real effort into their blog in the past, and prevent any possible evidence for which blogs and their posts actually stand the test of time. After all, there's nobody around who has already shown some capability for working on things for a long time, right⸮
DID THEY NOT SEE THE IRONY OF PUTTING OUT A PRIZE LOOKING FOR BLOGS FOCUSED ON LONGERMISM WITH POSTS THAT STAND THE TEST OF TIME, BUT EXCLUDE ANY BLOG OLDER THAN 12 MONTHS? AM I GOING CRAZY?
Supported by the FTX Future Fund™ and Longview Philanthropy®
Examples: “A Few Of Our Bloggers” Sections
Luckily, they include some blogs in the "A Few of Our Bloggers" section, so I can take a look at how well they have fared so far with regards to producing long-term content.
(If you are one of those bloggers, please don't take this as an indictment against your blogging abilities—but I'd like to do a case study. I'd be delighted if you proved me wrong :-)). For the time being, this will unfortunately be limited to collecting few datapoints (number of posts, date of last post, length of post) and rough impressions (in the long term, I plan to add all those posts to my collection).
- Ziggurat
- 3 posts (one of them an announcement post), decent length, last post April 7th 2022
- Impression: Good potential, especially with the recent update.
- Bridget Williams
- 2 posts, decent length, last post March 26th 2022
- Impression: Looks nice, probably a bit more in-depth than the average blog. Might become something.
- The Take Machine
- 1 announcement post, quite short, last post March 7th 2022
- Impression: This is not yet a blog, so I do not understand why you would link it in a "our bloggers" section.
- Sam Enright/The Fitzwilliam
- Heloise Investigates
- 1 announcement post, very short, posted February 15th
- Impression: Nothing here, similar to The Take Machine. Verdict: [REDACTED]
- Basil Halperin
- 15 posts, quite long, last post March 31st 2022
- Impression: I really like this blog: the first post is from 2013 (showing that the author is persistent, even if they're a slow writer, but who am I to call that a vice!), the author wants to write a long site but doesn't know it yet (seriously, look at the best essays page: add the other 6 posts to that, and it would work great as a landing page for the blog.) Verdict: We could be friends :-)
- Hands and Cities
- 46 posts, some of them extraordinarily long (I've been procrastinating on reading On Infinite Ethics for quite a while now), last post March 24th 2022
- Impression: Outstanding (and a bit depressing): The posts are more solid than anything I've ever written, on very interesting topics, with quotes from relevant poetry: This could be turned into a long site in a whim. Also an excellent illustration for why chronological archives often don't make sense: There's no reason why this post is deprioritised in the list of posts compared to this post. However, I suspect that these posts will not be updated over time (:-/), which will slowly make them less useful (although this is less of a problem for philosophy than for other disciplines)—in ten years someone might stumble upon Can you control the past and start scrolling, fascinatedly, an explorer in the ruins of a great ancient civilization.
Verdict: two webpages that aren't actually blogs, two young (but potentially promising) blogs with few posts, two medium-age blogs that have a lot of content (to the degree that I fear the authors might burn out or get disillusioned from the endeavour), and a very cute & old site.
The "Our Bloggers" section also lists one person who, as far as I can tell, doesn't have a public blog?
Counter-Arguments
I imagine the organizers of the Effective Ideas blog prize have several objections, here's two I can anticipate:
There's Not That Many Longtermist Blogs Around
The prize exists explicitely to encourage new & young writers, so I imagine the organizers perceive a current lack of blogs about longtermism and effective altruism (and related areas).
There certainly is no Marginal Revolution of effective altruism, and not as many people comment on posts on the EA forum as on ACX open threads.
Counter-counter-argument
Is that true? To be honest, I don't quite know: I recognize ~all blogs on this page, and most on this blogroll, but I would be a lying lier telling dirty lies if I said I'd read any non-negligible fraction of their posts. But I looking over those lists, I don't get the impression that there's a dearth of blogs about effective altruism, but rather a lack of discoverability or aggregation (why doesn't everyone of those post their texts to the EA forum?).
This is relevant: If there were very few EA blogs around, then it would make sense to incentivize the creation of new ones. If many old and semi-regularly updated EA blogs existed, but if they were just limited by funding or time, it would make sense to incentivize those blogs to increase their output (or reward them for their past contributions), and encourage them to better curate their content.
Blogs are for Discourse
Further, we think EA needs more strong writers who can share key ideas in prestigious and popular venues — to persuade people to work on the most pressing issues of our time and to advance our thinking about them. We want to incentivize EAs to develop those skills.
— Nick Whitaker, “We're announcing a $100,000 blog prize”, 2022
The goal of a blog, really, is not to produce really viable long-term content—it's often just about The Discourse™: Getting certain ideas into public perception, making the EA perspective a more acceptable stance in public perception. We want more people to at least know about effective altruism, and most people don't actually read a 180 page about iterated embryo selection—a short blog post is much more likely to be actually consumed by anyone (many people I've talked to tell me they've never finished a Gwern post—sad, of course, but understandable).
Counter-counter-argument
Blogging peaked in 2009; I was there, just.
— Gavin Leech, “Blogging is dead, long live sites”, 2020
But then, blogs occupy an uncomfortable spot in the informational ecosystem: The days of glory for blogging are unfortunately over, The Discourse™ is happening on social media now, in Twitter threads and Discord messages. All the substacks in the world will not change that if you want to be plugged in, you might want to make YouTube videos about effective altruism instead. (Sorry, the era of BoingBoing is not coming back).
Alternatively, I could see an EA newspaper as a good idea: having an institutionalized content & Discourse-producing machine à la Works in Progress or Jacobin will reach a different kind of people who demand the air of respectabilityof a newspaper—after all, blogs are not exactly high-status (perhaps this perceived lack of status is why I am so enthusiastic about long sites: they just feel classier).
Suggestions for Improvement
Since I obviously have opinions about blogs, but don't want to just criticize other people's hard work, here are some suggested improvements I believe would be quite beneficial.
Small Changes
On the less invasive side, I can propose one small improvement:
Drop the Age Limit
The 12 month age limit in the current prize makes little sense: If someone has been producing valuable content for a long time, they will probably continue doing so for quite a while. The current prize is unfairly excluding past effort.
Alternative Prizes
There's also more experimental structures available: Don't give out prizes; instead perform credit assignment for past work. Zack M. Davis outlines the idea in a personal context, transferring it to an organizational one should be reasonably easy:
So, I had an idea. You know how some people say we should fund the solutions to problems with after-the-fact prizes, rather than picking a team in advance that we think might solve the problem and funding them? What if ... you did something like that, but on a much smaller scale? A personal scale.
Like, suppose you've just successfully navigated a major personal life crisis that could have gone much worse if it weren't for some of the people in your life (both thanks to direct help they provided during the crisis, and things you learned from them that made you the sort of person that could navigate the crisis successfully). These people don't and shouldn't expect a reward (that's what friends are for) ... but maybe you could reward them anyway (with a special emphasis on people who helped you in low-status ways that you didn't understand at the time) in some sort of public ritual, to make them more powerful and incentivize others to emulate them, thereby increasing the measure of algorithms that result in humans successfully navigating major personal life crises.
It might look something like this—
• If you have some spare money lying around, set aside some of it for rewarding the people you want to reward. If you don't have any spare money lying around, this ritual will be less effective! Maybe you should fix that!
• Decide how much of the money you want to use to reward each of the people you want to reward.(Note: giving away something as powerful as money carries risks of breeding dependence and resentment if such gifts come to be expected! If people know that you've been going through a crisis and anyone so much as hints that they think they deserve an award, that person is missing the point and therefore does not deserve an award.)
• Privately go to each of the people, explain all this, and give them the amount of money you decided to give them. Make it very clear that this is a special unilateral one-time award made for decision-theoretic reasons and that it's very important that they accept it in the service of your mutual coherent extrapolated volition in accordance with the Bayes-structure of the universe. Refuse to accept words of thanks (it's not about you; it's not about me; it's about credit-assignment). If they try to refuse the money, explain that you will literally burn that much money in paper currency if they don't take it. (Shredding instead of burning is also acceptable.)
• Ask if they'd like to be publicly named and praised as having received an award as part of the credit-assignment ritual. (Remember that it's quite possible and understandable and good that they might want to accept the money, but not be publicly praised by you. After all, if you're the sort of person who is considering actually doing this, you're probably kind of weird! Maybe people don't want to be associated with you!)
• To complete the ritual, publish a blog post naming the people and the the awards they received. People who prefered not to be named should be credited as Anonymous Friend A, B, C, &c. Also list the amount of money you burned or shredded if anyone foolishly rejected their award in defiance of the Bayes-structure of the universe. Do not explain the nature of the crisis or how the named people helped you. (You might want to tell the story in a different post, but that's not part of the ritual, which is about credit-assignment.)
— Zack M. Davis, “"Friends Can Change the World"; Or, Request for Social Technology: Credit-Assignment Rituals”, 2017
The Outstanding Wikipedians Prize
Look at the Wikipedia pages for EA-relevant topics, and find the contributors who have participated most in the creation of those pages, contact them and grant them after-the-fact prizes for their efforts.
The advantage is clear: Wikipedia is not going away, and the go-to resource for ~everybody on a new topic is the Wikipedia page. 10 minor edits to Wikipedia might outweigh a year of blogging in terms of eyeballs and social utility.
The Gwern Prize
Instead of rewarding blogs, look explicitely for sites with long content, the more long-term, the better (ideally complete with Wikipedia contributions and archiving & tagging papers and open-source contributions and predictions and URL archiving), if they don't have sufficient funding, offer to fund them completely for a year. Make online conscientiousness be worth it.
Conclusion
I hope I have made a correct case for why the Effective Ideas prize is currently misguided, and perhaps even suggested some potential avenues for improvement.
Hello, thank you so much for your thoughtful piece. I am sorry about the missed email-these have been busy weeks, and it was never my intention to ignore you. You make really interesting points and I appreciate the engagement. Like any new project, we know there are still issues to work out. We recognize that this is an imperfect incentive structure, and we do welcome the feedback. We intend to learn from, iterate, and experiment during this process. That being said, even while imperfect, we believe the incentive structure created by the prize is better than the status quo’s limited incentives for new writers. Our main aim is to create something that, on net, improves the EA communications and media space. We think the prize is contributing to that.
Central points:
If I understand correctly, your core point is about the value of blogging relative to other forms of content. First on the object-level value of blogging you like:
“Except for rare exceptions” is doing a lot of work here: we created this prize exactly to discover exceptional bloggers. I agree that the most outstanding blogs create many times more lasting value than the average.
But I don’t think long-lasting writing is the only thing worth caring about: we’re especially interested in raising the salience of longtermism right now, as we look for people to lead new projects, and look forward to Will MacAskill’s What We Owe the Future.
Another goal, possibly the more important one, is this contest’s role in identifying talented writers and communicators for longtermism. Blogs are a specifically good way of searching for these skills, as they have low barriers to entry. For example, you write:
I agree. I’m actually an editor of Works in Progress. I’ve also been in discussions with two people starting EA magazines. To varying degrees, these projects are bottlenecked by a shortage of writers. We believe that the Blog Prize will introduce us to writers whose careers we could continue to cultivate beyond their blogs — to write for EA magazines, or join something like the EA Comms Fellowship this summer. After all, some highly impactful EAs (like Dylan Matthews and Kelsey Piper), not to mention some of the most prominent public intellectuals got their start blogging. Essentially, we’re hoping that this prize will be the first of many initiatives in this space to cultivate a robust tool of talent.
You make a similar point about books:
The same point holds: we can use blogs to identify talented writers now, who we will support to create all sorts of (different) content in the future. As you quote me saying, we want to incentivize EAs to develop skills which easily generalize from blogging to books to journalism, and much more. In a moonshot case, this contest could help identify future longtermist-oriented public intellectuals.
This relates to one of your central concerns, which is the “new blog” requirement. I understand how this could be very frustrating, especially given your history of blogging. But I hope you understand the incentives we wanted to create here: to identify new writers, and incentivize the creation of new content, which might not otherwise have been written. Were we to allow all previously written content to be eligible, it would actually be a disincentive for new content, as there would be so much more to compete against. In the hopes of partly reconciling this issue, we’re planning on announcing prizes for posts on specific topics beginning next month, which all bloggers will be eligible for.
To the further points about incentives, I agree that we should expect some people to stop blogging after the prizes are awarded. But where we’ve found promising new writers (not limited to the overall winners), we plan to continue supporting them — through grants or help with job placement. So while I agree that it would be bad to let good blogs vanish, I don’t expect that to happen.
You make a good point about web content being lost, more generally. I think I’ll look into finding a way to preserve, either in print or on a website, the best content that the prize generates.
Per your comments on the “Some of our bloggers” section on the website, I don’t think it’s appropriate for me to comment on people’s specific circumstances here. But I will say the point of these being on the website is to give potential bloggers ideas about different ways to connect their work to longtermist discourse. If you want to review a more broad swath of content, I would encourage you to look at our Twitter feed or our newsletter.
Some assorted comments:
We’re curating posts via our Twitter feed and monthly newsletter.
This is a useful point to respond to, because I’ve noticed a few people say something similar. There are, in some sense, many existing EA blogs. But as you have correctly identified, they are mostly geared towards internal discussion — the kind of blogs that are well-suited to Forum discussions. As we’ve tried to emphasize with this prize, we’re looking for content that crosses between the general blogosphere and internal conversations in EA. This is consistent with our interest in talent identification: we’re interested in people who can write about and communicate ideas in longtermism to a wider audience. It might be the case that community discussion deserves additional prizes, but that isn’t our focus.
This might be worth someone doing, but I see it as a separate project from this—the sort of credit an established writer deserves or could benefit from would be unique in comparison to new writers.
As a point of clarification, this project was funded by FTX Future Fund, but isn’t connected beyond that.
As a final note: so far, we’ve been very happy with the response from the prize. It has already generated two very successful blog posts:
Moreover, I’ve been generally happy with how many applicants are coming in from outside the EA community and are beginning to blog about EA and longtermism.
Part of our approach is to try multiple ideas, in the expectation that some will fail and some will succeed. Thank you again for your comments.
Thanks, corrected
This is an interesting critique! I think it misses a lot, though, so would like to push back on it.
Full disclosure/conflict of interest – I'm one of Nick's colleagues – we're both editors at Works in Progress.
1) Blogs are short content. – I think a lot of your critiques here (that they become outdated quickly, don't provide much long-term value, fall prey to replication crises) actually apply to all forms of published, static content – newspapers, tweet threads, newsletters, books, etc. We've all heard of books and news content that have aged badly – it's unclear why you've listed this as a drawback of blogs. If anything, blogs are much easier to keep updated than the others (as you mention), especially compared to printed content – you can easily update an old blogpost and signpost when you've done that. You can't edit a tweet thread, a printed book, or a news article easily.
I don't think people need to read through entire archives of blogs for them to be useful. People often share links to particular old blogposts as references on a particular topic, and that's fine. In the same way, we don't say that newspapers are bad because people don't read through newspaper archives.
2) Did anybody think about the incentives? – as you mention later on, the purpose of the prize is to incentivise new blogs to be created and maintained, so it wouldn't make sense to reward ones that already exist. I don't think it's ironic because the topic is on longtermism – and it's likely that at least some of these blogs will be maintained in the longterm, which may be another way to look at it. Many projects (and blogs) are likely to be unfinished, but that's a feature of new projects in general. One way to improve the prize might be to reward blogs that stay maintained years from now, but I don't think you make that point.
3) Examples – skipping over this as it looks like you liked many of them.
4) There's not that many longtermist blogs around. To me, it seems like the EA and longtermist movements are growing rapidly in size and could be a lot bigger than they currently are, so what may seem like a sufficient number of blogs now wouldn't be later. If you recognise all the blogs on that list, that seems like an indication that there aren't very many of them. Ambitiously, people might want to reach a level where there were so many EA blogs that they weren't able to keep track of all of them. EA Forum is great, but if EA was huge, people might not use this as the central forum to cross-post all their blogposts. This seems more like a central node or bridge to other content than The place to put everything EA related.
5) Blogs are for discourse. I think you may not be aware that Nick's already an editor at Works in Progress (the long form magazine you mentioned). Blogs and longer form discourse magazines don't seem like an either/or to me, and not to Nick who's involved in both. I think they actually feed into each other: We sometimes recruit authors because we've read their blogs and want to develop their content further. And we'd be very happy if bloggers riffed off ideas that we've published on another platform like their own blog. In short, why not both?
Thanks for the detailed answer :-)
The structure of blogs doesn't encourage this either: usually arranged chronologically, not by topic, with a focus on novelty.
As for reading archives, there is certainly a style of blog that is in practice not linked very often in the long term (I'm thinking of Overcoming Bias or Marginal Revolution or Econlog).
Interesting! I thought I was absolutely making that point, especially in this section and especially especially in this section.
You list 1 person who doesn't have a public blog at all (!), 2 people whose blogs contain 0 content (!!), 2 more people who have written 3 blogposts each, and 3 more bloggers who actually have presentable blogs. That 3/8 blogs that could be in the category of "Flagship blog". Not, I think, a good ratio.
Maybe it's that I think that a prize is not the perfect way to approach this: Prizes seem to be useful for very discrete problems that have a very clear solution criterion, and less useful for very long-term, open-ended endeavours (where something like certificates of impact or retroactive funding are more suited).
I think my phrasing might have been unclear earlier – I'm Nick's colleague at Works in Progress, but not on the blog prize and don't have any involvement there.
1. I think that blogs fill a different purpose to many other formats you mention, but are also more feasible than writing long-form: for people who have other commitments, for writing short commentaries, for responding to topical events or stories, for publishing independent parts of a series in a way that makes each part more shareable. I'm sure you can think of many examples of each of these. I think it's not important for them to be searchable in the same way as it is for encyclopedia entries, although that's a bonus. YouTube videos are an alternative but they also have a different demographic audience and people who prefer to consume information in a different format, so they're not interchangeable in that way, in my opinion.
2. Those aren't quite the same as I suggested, which would be more like a prize for new blogs that are maintained in the longterm, or an additional prize for longterm maintenance.
3. (I'm not involved in this so don't have any comments)
4. I think those are a different sort of problem. Prizes for open ended endeavours – such as answering an unsolved problem – don't have a certainty of being resolved. Prizes for meeting some criteria, which involve essentially improving on existing methods, are more effective than those, as Anton Howes has written about here. But neither are the same as having a prize with the certainty that someone will win the prize out of the candidates that apply. A closer analogue of this prize is probably a competition.
Thanks for this post. Though I am not quite convinced by most of the reasoning, and I understand that FTX LTFF's awards aims to encourage new bloggers, instead of rewarding old successful ones (which would better be done by something like Impact Certificates, instead of awards), I really appreciate your points - particularly the critique to short content. I am afraid that blogging might too often be like preaching to the choir - and that journalism and books have a better shot at affecting new audiences (especially policy-makers).
Thanks, I'll take a closer look at impact certificates.
Small points:
"The 12 month age limit in the current prize makes little sense: If someone has been producing valuable content for a long time, they will probably continue doing so for quite a while. The current prize is unfairly excluding past effort."
Isn't the point to incentivise additional blogging activity? A $100,000 prize for Scott Alexander is unlikely to increase the quantity/quality of ACX/SSC posts.
Also, if through this prize you have developed the habit of blogging/built an audience, then I suspect you are likely to continue. Especially, given how easy it is to monetise a newsletter/blog today.
“Except for rare exceptions (Slate Star Codex being the most notable one), blogs usually don’t provide much long-term value—who cares enough to read the whole archive of a blog, unless the author is exceptionally skilled?”
The whole point is surely to find and encourage more SSCs, and within a few weeks, they seem to have had some real success with Hands and Cities/The Fitzwilliam based on your assessment.
Major point:
I think you significantly underrate the pedagogical value of a blog. Marginal Revolution has influenced the way I think about economics, longtermism, and effective altruism. But I can't easily point to the eureka post. I can think of the same with many other blogs. My knowledge of nominal GDP targeting, human capital signalling, zoning/spatial economics, optimal tax theory, etc. are all the result of reading blog after blog. I can't think of many, if any, books that have had the same impact on my worldview. Maybe I'm unusual on this front. But I suspect I'm not at all.
In the case of Scott Alexander as an example, it seems noteworthy that he was writing online from at least 2006 on his LiveJournal. This seems to be a common thread with many well-known bloggers: they build up a following over a long time, and hone their skills with repeated practice. My intuition is that the marginal Scott Alexander is more likely to already be writing online, and might have done so for a couple of years already, than to be on the fence whether to do any writing at all.
I'm not sure how easy it is to monetize a blog/newsletter today—afaik, most bloggers make not enough money to be worth it the additional hassles with taxes. But I might be wrong, I've never tried it.
Minor point: Hands and Cities/The Fitzwilliam were created before the prize, so I would put them in the "found" category, but I don't think Hands and Cities would technically qualify for the prize—it's older than 12 months (having been created October 2020). (The Fitzwilliam does, but only because Sam Enright switched platforms—his blog was started in november 2020, which would disqualify it for the prize; but that's where all the good content is!)
I definitely don't underestimate the pedagogical value of blogs! I've read a fair share of them over the years, and learned nearly everything I value knowing from them. My complaint is that blogs often capture the outer loop of a community in a way that is far from optimal, and that most blogs are just really inefficient (such as Marginal Revolution or Econlog or Overcoming Bias) because their information is just scattered over many posts and not fully organized anywhere, as opposed to sites such as Gwerns (other positive examples are Essays on Reducing Suffering, An Anarchist FAQ, Ethan Morse's site, Metaculus, XXIIVV, nintil, FAQs and of course Wikipedia).
Perhaps we'd need a third outer loop to distill findings from blogs into long content, then?