Essays

I’ve followed the career of Paul Graham for a large part of my career. He was a Lisp hacker from MIT that started a company that had a web site that would allow you to create your own custom web site strictly by filling out forms on the web. You didn’t need to learn HTML or CSS. You just had to pick options off of lists and fill in boxes with the text you wanted to display as your content.

Paul eventually sold the company to Yahoo! and started an angel investment company called Y Combinator. His idea of an angel investment company was somewhat unique. They held events that they called Demo Days where potential startup founders would pitch their ideas to Paul and his partners. They would pick the best of the lot and then put them through a sort of startup boot camp where they would attempt to teach them things that would help them succeed with their new company.

The interesting thing was, most of the Y Combinator graduates went on to run successful startup companies. One of the insights that Paul brought to the table was that you shouldn’t select startups based solely on their ideas. Rather, you should select them based on their founders. He observed that good founders would eventually stumble across some product or another that would succeed whereas founders that only had a good idea were out of luck when that one idea fizzled out as it so often does.

The reason I know so much about what Paul Graham observed about picking winning startups is because I read his essays. After becoming a very successful serial startup founder, he discovered that he liked writing essays. He published a book of his essays, Hackers and Painters: Big Ideas from the Computer Age. But even after that, he continued to write and post essays on his website.

His essays are all very well written, very well reasoned, and highly polished. He spends days, sometimes weeks, writing them and tweaking them until they feel right to him. He contends that the difference between essayists and journalists is primarily that journalists work under a deadline.

I find myself attempting to write essays under a self imposed deadline. Maybe they would be better if I put off posting them until they just felt write. Perhaps I should get people to review them and comment on them before I post them. But somehow, that’s not how this site works.

I will continue to write my posts off the cuff, posting them after a light proofreading. That is the style of this blog. Maybe I will write essays Paul’s way sometime in the future. I doubt it. If I don’t set deadlines for myself, I never get anything done. If that makes me a journalist instead of an essayist, I’ll take that.

Take care of yourself and your loved ones. Wash your hands, wear a mask, and maintain social distance.