on investing and art

Investing and art have far more in common than they first appear to.

I’ve thought about this a lot over the past few years. Both require some combination of taste, judgment, patience, and the ability to see value before broad consensus forms. There are frameworks for both, of course. As investors, we have financial models, market maps, research, comps, customer calls, expert opinions, and all sorts of tools that help us make something uncertain feel a little more certain.

The art world has its own versions of this: provenance, exhibition history, auction results, galleries, museums, critics, collectors, and institutions that help shape what is supposed to matter.

In both cases, however, there eventually comes a point where all of that runs out and you have to decide what you think for yourself. You have to look at something before the rest of the world has completely agreed on what it’s worth, or sometimes even what it is, and decide whether there is something there. I think that is part of why I’ve become increasingly interested in taste.

Taste is difficult to define without sounding slightly pretentious, and I’m not sure I completely understand what it is myself. I think of it less as knowing what is “good” and more as developing some internal sense for what deserves my attention. The people I find most interesting in both art and investing seem to be unusually good at this. They notice an artist before everyone knows the artist. They meet the founder before the company becomes obvious. They recognize that something feels original before there’s enough consensus around it to make that opinion comfortable.

Art has made me a better investor in this respect because the more of it I see, the more sensitive I become to originality. You start noticing when someone appears to be making something that actually belongs to them, rather than a variation of something that already exists. There is a point of view behind it. You may not like the work, and you may not even fully understand it, but you can tell that the person responsible for it saw something in a way that was distinctly their own.

I’ve started paying much more attention to that quality in founders. The founders who stay with me tend to have spent an unreasonable amount of time thinking about something most other people have barely noticed. Sometimes it’s a problem that has irritated them for years. Or, maybe it comes from a particular experience they had. Sometimes they see a change occurring in the world that other people have not yet taken seriously. Their ideas can initially sound strange or overly specific; further, the market can look too small because the rest of us are still evaluating the opportunity through the world as it currently exists. Nevertheless, there is an obsession underneath many of them, and I think looking at art has made me more attuned to it.

I’ve also noticed that some art stays with me long before I understand why. I can walk away from a work and find myself thinking about it several days later, even though I couldn’t have given you a coherent explanation of what I liked about it while I was standing in front of it. Over time, I’ve become more comfortable taking that reaction seriously without pretending it’s some infallible signal. The same thing occasionally happens after I meet a founder. Something about the company continues to occupy my mind after the meeting has ended, and I find myself returning to the deck, thinking about something the founder said, or suddenly noticing the problem they described somewhere else.

Investing, in turn, has made me appreciate art more deeply because it made me interested in the relationship between price and value. A painting is, at its most fundamental physical level, just pigment applied to a surface. One work might sell for a few hundred dollars while another for tens or hundreds of millions. Clearly, the economic difference between the two cannot be explained by the cost of the canvas or the paint.

Value accumulates around the work in a much more complicated way. There is the artist and the work itself, but there is also history, provenance, scarcity, critical reception, the collectors who wanted it, the institutions that displayed it, the other artists and movements it became associated with, and eventually some broader cultural belief about why it matters.

Financial markets are not entirely different, even if we sometimes prefer to think they are. An investment contains a certain set of facts, but it also contains beliefs about a future that hasn’t happened yet. You believe a company will matter more than it does today, that a technology will become critically important, that a founder will be capable of building something much larger than what currently exists, or that a market everyone thinks is small will eventually reveal itself to be far larger. The numbers matter enormously, but the numbers themselves are often built on assumptions about a world that simply does not yet exist. You are ultimately trying to see something before it becomes obvious.

That does not mean, however, it gives anyone a pass to be contrarian for the sake of being contrarian. Art and investing both punish that too. There’s plenty of bad art that nobody understands because there may simply not be much there, just as there are plenty of unusual companies that are unusual because they are bad businesses. Developing judgment seems to involve learning the difference between something the world has overlooked and something the world has correctly ignored, and I’m convinced that this is one of those abilities that can only really be developed through repeated exposure, mistakes, changing your mind, and spending a tremendous amount of time… looking.

There is another reason art has become more important to me lately, and it has less to do with investing than with the world we seem to be entering.

Writing this in October of 2026, we are increasingly surrounded by things generated by machines. Images, writing, music, videos, software, advertisements, and even ideas can now be produced within seconds at a level of competence that would have seemed remarkable only just a few years ago. Surely it’s an incredible development, and I use these tools constantly myself, but it has also made me think more carefully about why certain human creations affect me in a way others do not.

In a good piece of art, oftentimes I can feel the person behind it. Their obsessions, fears, memories, instincts, contradictions, and particular ways of seeing the world all find their way into the work somehow. I like knowing that another person lived some version of a life that eventually caused them to make this specific thing, and that whatever they experienced or noticed moved them enough to translate it into something another person could encounter years later.

Maybe that’s part of why art touches me as much as it does. It is evidence of attention. Someone looked at the world carefully enough to notice something, felt strongly enough about it to make something from it, and left that object behind for someone else to experience.

I’m not entirely sure whether art has made me a better investor or whether investing has made me appreciate art more deeply. I suspect both have changed the way I look at the other, and perhaps more importantly, both have made me more conscious of how much judgment begins with learning where to direct your attention.