Watch Me As I Lose Another $100k

I’ve always lost money in the stock market. Not relative to the market, just plain lost money. I’m emotional, I buy things I like. I get scared and sell when the market is down. I get excited and buy when the market is up. So years ago I gave most of my investing money to a professional, Dean Colling at CIBC, and he’s done well with it. On the occasions when he’s disagreed with me, he’s always been right. I bought cannabis stocks. I bought too many psychedelic stocks.

Many of my friends are active investors. At dinner parties they talk about the latest meme stocks, S&P 500 options trading, whether the market is up or down and why, it all seems so fascinating but I have no idea what they’re talking about, so I wander in, hear a few sentences, then wander off to talk to someone about psychedelics or movies, because I have nothing to add.

Well I’ve had enough Dean, it’s time for me to figure this shit out! I’m fascinated by AI and recently ran across an AI stock picking engine called Danelfin. I decided to try it out, signing up for an account, and picking 10 stocks to put into an imaginary portfolio. This was two weeks ago. Watching the stocks go up and down during those two weeks, the predictions of the AI seemed to make sense, so here we go for real.

Thirty minutes ago, I got a new set of 10 top picks from Danelfin. Then I transferred $100k into my little-used direct trading account at RBC, and bought $10k worth of each stock. I want to make this clear: I have NO idea what any of these companies do. Except PayPal, I’ve heard of them. You’re thinking this has got to be the dumbest use of $100k Sanjay has ever embarked on, but no, there are dumber things I’ve done. I’ll write about them eventually.

Here they are in my brokerage account, just to prove I actually hit enter on the trades. My strategy is to buy stocks with an AI score of 9 or 10, and then sell them when they fall to 7 or lower, which is still a ‘buy’ according to Danelfin, but I think a weak ‘buy’ is really a ‘sell’.

I know what you’re thinking. Sanjay, you’re doing all this writing, you have a family, a PlayStation console, don’t you have better things to do than trying to learn how to trade stocks?

No, I really don’t. This isn’t about making money, at least not mostly. It’s about learning and daring to get back on the horse. And besides, I can’t lose the entire $100k right? What do you think? Am I going to beat the market? I’m using the S&P 500 as my benchmark, which as I write sits at 4450. I’ll write updates as stocks move. Giddy up!

1. Update 1 - not going well.

2. Update 2 - going even worse.

3. Update 3 - a new hope?