Latest Insights on SI

How could AI topple the software industry? AI Might Not Kill Software, But It Could Do Something Worse Ian warns about how AI could destroy one of the biggest advantages that made software companies so valuable to Wall Street.
Trade LESS, Study MORE
by Tim Sykes October 19, 2026 Tim Sykes Daily
Today marks the 39th anniversary of Black Monday — the infamous 1987 stock market crash when the Dow Jones Industrial Average plunged more than 22% in a single session. Now, I’m certainly not predicting another Black Monday. But with the market already under pressure, momentum deteriorating, and stocks breaking to new lows, the timing is a little too close for comfort.
How could the software industry avoid an AI-driven SaaSpocalypse? Software Isn’t Dead Yet Ian explains why investors might have been too quick to bury the software industry and how AI could increase some software companies' value.
How Much You Need To Start Trading
by Tim Sykes October 16, 2026 Tim Sykes Daily
Over the years, a LOT of people have told me that they had to “get over the PDT rule” before they started trading. Here’s what I’ve always said… That’s just an EXCUSE. But guess what? Now that the PDT rule is gone… There is NO EXCUSE!
How is AI giving some companies a huge advantage? Chart of the Week: The AI Boom’s Surprising New Divide Some companies are using artificial intelligence a lot more than others. Ian shares a chart showing just how wide that gap has become.

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