Late last year, I got this email from Jonah Franks of Public Intellectuals for Charity. Reprinted with his permission.
I personally don’t know any good answer, so I especially appreciate your thoughtful responses in the comments.
Who is the Bryan Caplan/Michael Huemer/Robin Hanson/Tyler Cowen/Scott Alexander of business, investing, finance, entrepreneurship, (real estate?,) org management, etc.? I am looking for a uniquely intellectually responsible, data literate, supremely competent human being who happens to specialize in the making of money. It could be via any medium: a great lecture series online by some rockstar professor, or a scintillating weekly Substack newsletter, or your nominee for the gold-standard business podcast. An amazing audiobook, textbook, or online wiki-type resource. I don't care; I just need something that will cut through the fog and the bullshit that demonstrates impressive intellectual clarity, resistance to bias, consciousness of the empirical worldview.
Who is Scott's counterpart to being a pure voice of reason in a desert of nonsense and cynicism with respect to his topic area? Of course, if no one such person exists, I will happily take the closest approximation: maybe there's someone who is really really really insightful and reasonable and balanced on the topic of real estate investing, but nothing else. Please don't hesitate to mention this person, even if he doesn't have the magnificent polymathic generalism of Scott. Anyone who appreciates fine distinctions, shows cognitive empathy, takes care not to conflate importantly different concepts and words, anticipate the most likely and most promising objections to their current line of argument, who can map out contingencies in an argument, who can track conversations without losing the plot, easily identify the extreme implications of another person's views, who always seems to have persuasive illustrations, examples, and analogies at the ready for any situation, someone who just makes consistent penetrating sense, and who happens to direct these intellectual virtues toward the discipline of business. Being a clear writer is a plus, but not absolutely necessary; I'd rather learn true things the hard way than false things easily.
(BTW, is there a "LessWrong" of financial mathematics/business/career development/etc.?) (The closest thing I've been able to find to what I have in mind above is Eric Tyson, who can be a long walk for a short drink. Please let me know if this guy is a crackpot! I am asking this not in spite of but because of how little I know, so I don't necessarily expect that I've already found the right sort of person to listen to and read.)
Byrne Hobart and Paul Graham
Matt Levine maybe? Zvi Mowshowitz when he approaches the topic? Idk, the real top dead centre for this description is someone too busy making mad money at Jane Street to write a substack about it.