The Other Money Problem

By Evan Miller

December 11, 2014

I admit to feeling a twinge of excitement last summer when I read that Paul Graham was leaving his jillion-dollar job to write more essays. It felt like the thinking man’s equivalent of LeBron James returning home to the Cleveland Cavaliers to play ball. I don’t know; it’s just a good human story when people decide to return to their roots, as if after a long and weary odyssey.

I wouldn’t envy Paul Graham’s position as a writer, however. The world is awaiting his words, but he’s been out of practice. It will take time to get his old swing back. He will get it back, in all probability; but his writing will be hobbled by a more serious handicap.

Paul Graham has been thinking about start-ups the last several years, and he is almost certainly going to write about start-ups now. That’s how he spent his forties: working with start-ups, talking about start-ups, thinking about start-ups, sending emails about start-ups. I am sure he comprehends start-ups like never before. However, it’s unlikely he’ll achieve his previous heights as an essayist, for a simple reason: his advice to readers, now, is tainted.

The thing that was so striking about Paul Graham’s original essays was that they read almost as a kind of paranoid thriller. The world was out to dupe and enslave you, but he, Paul Graham, was — disinterestedly, dispassionately — going to get you out of here alive, armed only with Lisp, random facts about medieval Florence, and deep knowledge of Business Things.

That rhetorical position is now compromised. If Paul Graham tells you to start a start-up, and you do it, he stands to make money off you. If he tells you not to start a start-up, his co-founder wife, and all the start-up friends he’s made over the last several years, will be mad at him.

It’s possible that he’ll surprise us all and say that, on further reflection, the whole start-up thing was a mistake. I would guess there is a zero percent chance that he will say this. The problem is that if he doesn’t say this, well, his essays will be lacking in their erstwhile authenticity. They might offer brilliant insights into how to do start-ups, but there won’t be that same sense of conspiracy between reader and writer in telling you why you should start a start-up.

Before, he was the guy telling you don’t trust the system, especially not those dirty rotten VCs. Now he’s a part of the system, and he’s thanking VCs for reading drafts of his essays.

It’s the other money problem. Just as having a lot of money drives a wedge between friends, power drives a wedge between writers and their audience. It spoils all the fun. Sure, things might look the same as before. But they just won’t feel the same.

Companion essay: Start-Ups and Emotional Debt


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