From time to time I’ll get asked why I don’t write more about the topic of investing. I’ve long held that I only wanted to write about a topic that I felt comfortable enough in my knowledge to write about. And I was still in learning mode for VC. But as I approach a decade in, that mentality has sort of shifted. If I’m being honest, it’s more that I find that type of content vapid.
And it’s actually worse than that. It’s often meaningless or actually detrimental. Sure, if you’ve been an investor long enough, you’ll have certain earned wisdom on deal structures and the like. And there’s undoubtedly pattern recognition for certain types of things. But in technology in particular, things change and shift so quickly that a lot of knowledge is much less useful than you might think. And again, it can often be counter-productive to share.
Talking to entrepreneurs, I find it best to acknowledge that you’re perhaps on a journey together and you have no idea how it’s going to play out. So much of it is luck, but even more of it is timing. Hard work is a prerequisite, of course. But mainly to ensure that your company is in the right position to capitalize on the luck of timing, should it come.
I prefer to be a sounding board. To talk about new ideas, even if tangential to the business at hand. To pull stuff out by way of provoking thought.
And that’s why I write about seemingly random things — okay, and Apple — more often than I write about VC or investing or the like. I write to clarify my own thoughts and to stimulate my own brain. It’s not some guidebook from someone who has it all figured out. Those types of posts read ridiculous because they are ridiculous. There are exceptions, of course.¹ But mainly in that they spur thought and tangents. They’re never going to be some letter of some law.²
That’s because the questions are always changing, so how can the answers be the same? It’s best to admit you know this side of nothing and instead talk through how you can actually get smart on a topic. And you’re probably not going to write a blog post about that because it would be incredibly boring to almost everyone who would read it. And more to the point, it would probably be out of date by the time it was published.