The Caboose

I didn’t get Amazon Prime until about 2016 or so. I was like, Screw you, Amazon. I am not paying $100 bucks a year for free shipping. I will just get my packages delivered slowly. Finally, I capitulated, paid the $100, and started getting my free two-day shipping. This is the greatest thing ever! 

I didn’t get a smartphone until 2012. I didn’t get a cell phone at all until 2006.

Even today, I use AI but only sparingly. I hear about these people vibecoding apps and stuff, and I have no idea what is going on. I mostly just use it for research, maybe once or twice a week. Although recently, I did use AI to create a flyer for a party in NYC (more on this later). It saved me a few hours of screwing around with Canva.

I am the caboose. I am the last person to learn about trends in tech. Therefore, I am a terrible tech investor. It is true!

The good news is that even though I am a terrible tech investor, I am a pretty good investor overall, and in spite of what’s happened in the last 15 years, I don’t think you need to be a good tech investor to be a good investor. You can be the caboose and still make money.

I have a friend who is not the caboose. He is the one who is vibecoding apps. I don’t even know what “vibecoding” means. I’ve stood behind him when he is in front of his computer, and he is cycling through windows and tasks so quickly, I don’t even understand what is going on. I knew guys like that at Lehman Brothers, who were so proficient in Excel it was like listening to someone speaking a foreign language.

It's not so much that I’m a technophobe; it’s just that I have other things on my mind.

Other Ways to Make Money

As you know by now, I make my money in the markets with sentiment, trading against extreme highs or lows. At least, that is how I used to make my money—I’ve been forced to become a little more creative in recent years.

But I don’t have a monopoly on good ideas either. Some people are really good with fundamentals, and I don’t see how it is possible that people make money with fundamentals, but they do it. Other people really understand options and can trade volatility. And some people can do relative value trades in the global bond markets. There are a million ways to make money in the markets. I think sometimes you get people who are successful investors and they begin to think that my way is the only way, and then they start picking fights with people on X. Hey, if what you’re doing works for you, I’m not going to tell you to do something different.

If you haven’t found your way yet, keep searching. Keep trying. Read some books, and maybe you will get some ideas. I am butt-deep in technical analysis, and while there are a hundred different technical analysis techniques, you only need to use a few. In the spirit of keeping things simple—but also, if you use all of them, you will get paralysis by analysis. I discovered my methodology 20 years ago, and I have been using it since, and it has only let me down once.

Don’t Look to Me

But don’t look to me for answers on tech. Actually, you can look to me for answers on tech—if you want to catch the move lower. By the time I discover a trend, it is getting down to tag ends. What I am suggesting is that you use me as a contrary indicator, at least when it comes to tech. If I make an app on Claude, and I write about it in this letter, you should probably short the whole darn thing.

And by the way, that is a respectable way to make money: shorting things. It is also a very difficult way to make money, but some people are good at it. At least, if you don’t have impeccable timing, it is difficult. I don’t like shorting stocks—I don’t like the idea of getting my head blown off on earnings, but I will do it. 

One other thing I would like to point out: With any new technology, it is usually easier to pick the losers than it is to pick the winners. Like with AI—the software stocks are obvious losers. Who are the winners? Well, OpenAI and Anthropic, but those are the obvious ones. What else? No answer. There will be winners from AI as well as losers, but it is a lot easier to pick the losers. The same was true of Amazon Prime—short Target. The same was true of smartphones—short Nokia. The same was also true of the Apple Watch—short Fossil. That one, by the way, was one of the best trades in history, if you figured it out.

I am the caboose. I know how to use Microsoft Word, I know how to use a web browser, and I know how to use Bloomberg, and that is about it. And I know how to do some music stuff too. But my $3,000 iMac is basically a glorified word processor. Pretty soon I am going to have to switch to the large font on my phone because I can’t read my screen, like all the Boomers you sit next to on airplanes. I never got Snapchat. I have Instagram, but I barely know how to use the stories. And I don’t feel like sending my biometrics off to Beijing, so I never downloaded TikTok either. The world has passed me by. And that’s okay, because I can still trade circles around all of you.

Jared Dillian, MFA