64 Comments

Byrne Hobart and Paul Graham

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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.

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Scott Alexander writes well about science (amongst other things), but doesn't actually do that much science.

So I think we can take Matt Levine: he writes about people making money, but doesn't make that much money himself.

(Not to worry, Bloomberg pays well. He just won't become a billionaire any time soon from his work.)

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Warren Buffett is my pick. He has a the most proven track record on making money with only financial knowledge. The only billionaires ahead of him also have tech expertise. He has not written too much, but every letter to his shareholders I have read so far have been very insightful.

https://www.berkshirehathaway.com/letters/letters.html

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Honorable mention: Ben Thompson from Stratechery.

CommonCog has a much broader focus than just tech, but Ben has created a top notch tech focused family of business publications/podcasts.

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There are many great business thinkers, including Patrick Collison, John Collison, W. Edwards Deming (deceased), Aswath Damodaran, Hal Varian, Michael Gibson, and others

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Warren Meyer over at Coyote Blog had some really good essays about small businesses and entrepreneurship in general. I don't know if he is still writing, or will start writing again any time soon.

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I did enjoy his blog but he sure did get Tesla wrong.

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I am not sure he was 100% wrong yet. I am more positive about Tesla than I was 10-15 years ago, but I don't think all electric cars are going to pan out well. We are getting to the point where these all electric cars are starting to need replacement batteries, and finding out that whoops... that costs upwards of 30,000$. My guess is, and was I am pleased to say, that sort of cost will turn out to be a huge problem for them. The very rich will not care, but it seems to me that a car that needs replacing (or spending ~50% of it's new cost) every 10 years is going to be a deal breaker for anyone in the middle class. I suspect that when those batteries start piling up it is going to be an issue, too, one that might get regulatory attention.

So while I think Warren probably expected the Tesla fall to happen to soon, I don't think we can bank on the company staying strong just yet. Then again, Musk is terribly clever and might well pull through a lot of these problems. I am glad he stopped making claims about things like all electric tractors being just around the corner that turned out to be false. It feels like he matured a bit.

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The cost of batteries is falling and performance improving.

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Yes, and someday they might be in the right spot for all electric cars to be really viable. I am not opposed to the idea that they will be, but the cost of batteries has been falling while performance improves for quite some time now, it just hasn't been enough to get prices where they need to be yet. It probably won't be enough to get prices to where they need to be in another ten years I would guess.

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There is no business equivalent of those people. The reason being, those people write about academic subjects, but being good at business requires one to be non-academic.

The best business people are able to take complex, multivariate situations and reduce them to simple stories that enable decisive action. The Scott Alexander’s of the world, on the other hand, take simple stories we tell about complex things, and zoom in on them to reveal the inherent complexity.

In short, the skills that make one good at business and the skills that make one a good academic writer are different. You won’t find a person who is good at thinking about business in the same way Scott Alexander is good at thinking about the ethics of AI because those are different types of thought.

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For the big picture, Charlie Munger

On the data-focused side, Aswath Damodaran

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Cedric from CommonCog.

https://commoncog.com/

For a taste of his thinking, check out his analysis of John Malone's invention of EBITDA as an example of why many successful businesses people focus on cash flow over profits.

https://commoncog.com/cash-flow-games/

Paul Graham is a great choice as well, but Cedric is an up and comer who regularly publishes new, great content. Paul Graham is more of a legend who has a very strong body of existing work.

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+1, was going to rec this

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Yeah, I haven't gotten very far into it yet, but CommonCog was my first answer too.

I'm personally not that interested in the business-specific topics though. I'm more interested in learning how to think better about problems that are fuzzy and ill-defined, and he has a lot of great analysis for that too.

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Edward Thorp would fit the bill, but doesn't write all that much afaik. He is definitely smart, quant, and a money making machine.

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I nominate Clay Christensen. A brilliant Genius without a successor yet:

1 - Insight that every theary is dependent on the circumstances to which it applies

2 - analysis of shift in competitive dynamics from when technology is not "good enough" for client needs to when it overshoots client needs

3 - Dynamic analysis of strategy and progress in a discipline that was focused on structure and static analysis

4 - Independent thinker. Never worked a single Sunday for Relegious belief. Always followed internal beliefs

5 - Tremendous real world impact. Influencing major entrepreneurs from Ellison to Bezos.

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Clayton Christensen is a very smart, gifted guy. But he is an academic, not a businessman

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He also had a business career as the CEO of Special Materials company. But agree that my mention here is from his Academic work. But if you are talking about "Best Business Thinker" he needs to be in the running. I was lucky to be a student of his and his depth of thought is not captured by his amazing books.

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Ok, actually I will legit apologize and concede, especially if the goal is to create a short list of people worth reading, as opposed to narrowing it down to just one

Rereading the OP’s request, I had focused in on the (single) “best at making money” part. But indeed he asks for other stuff as well, and certainly in that context Christensen no doubt qualifies.

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Peter Thiel

Also Noah Kagan has a great YouTube channel that interviews people that made lot of money.

https://www.youtube.com/@noahkagan/videos

Sam Parr are pretty good too:

https://www.youtube.com/@MyFirstMillionPod/videos

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Prof. Ashwath Damodaran of NYU Stern School of Business and 'The Rational Reminder' podcast hosted by two Canadians, Ben Felix and Cameron Passmore.

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Rational Reminder podcast is the best readily accessible source on investment for me

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"Investing", "entrepreneurship", and "org management" are really each completely different things. You wouldn't expect an expert on one of them to necessarily be great at the others, just because they are business-related. It's like asking for someone who is a good thinker in chess, music, and soccer, because they are all hobby-related.

That said, for entrepreneurship the best thinker of our era is Paul Graham. Read his essays online.

For org management, it's harder to learn about this subject by reading and thinking, because if you have no management experience, much of the advice won't make any sense. Kind of like reading about chess tactics if you haven't played chess. But, if you're looking for online material I like the Rands In Repose blog; the book High Output Management is also good.

For investing, I think this breaks down into different types of investing that don't really share that much with each other. I have known experts in real estate investing, stock picking, and startup investing, and they just don't share that much in common. Plus, there is this phenomenon in investing where when you learn something valuable, you keep it to yourself to make money, and then once you make it public it loses its value. So I don't know what to recommend on investing.

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Peter Thiel. The book "Zero to One" is a good example.

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Charles Koch

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