Speculative Investments

Now that the Shareholder Poker Tournament is only once a month I’ve found I need a little more “speculative investing” in my life. Initially I tried playing some scratch-its but that’s a pretty cheap thrill.

Then I went the other direction, and using my expertise from Hamburger Business Review decided to buy $100 of McDonald’s stock during a dip.

Easy profits, but I’m not the day trader type. This is a long term investment.

🥣 Just Right

When the US Open started I realized I was sitting on a goldmine. We were in Canada and Kathryn’s parents are deep tennis fans. They’ve have been watching the major tournaments since before I was born and attended the 1978 US Open, which was the first year it was at Flushing Meadows. So with the advice of two experts (a lot of opinions are stated very loudly) I decided this was a perfect way to try to make some money.

🎾 Tennis Advantage

I started making a few bets a day as I was relearning the terminology and structure of sports betting and the particulars of tennis. I went for a few underdogs and won some money early then tried betting on the favorites, but I had to risk a lot to win a little. I experimented with some of the odder bets, like who would win the first set, or if a favorite could win and also win the first two sets… that started to feel a bit reckless.

With tennis being over I am looking to expand my “expertise.” I know nothing about F1 Racing but Kathryn’s father has become my gambling advisor (he asks for a 5% take on all winning recommendations) and his sports are tennis, F1, boxing, and hockey. I’ve had luck in the past with bets on WNBA and politics (shout out to Election Profit Makers), and sometimes I like to bet on baseball because it’s boring to watch otherwise.

To be honest, more fun than winning has been tracking the bets! I created a chart to track my performance and how much I was risking vs. how much I stood to win. Obviously the more I risk implies a better chance of winning, and vice versa.

The diamond represents what I actually won or lost that day, and the dotted line is the current profits/losses of my bankroll. (Sept 10th is the shareholder poker game.)

We had a bit of a Tufte-inspired chat on Slack about the presentation of this chart and I have some ideas for a better design but I’m a bit limited by Google Sheets functionality. 


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