Microsoft: Parallel Wagering and Risk
January 30, 2026
Another dinobaby post. No AI unless it is an image. This dinobaby is not Grandma Moses, just Grandpa Arnold.
I had a French teacher who loved French proverbs. Her name was Madame Matthews, and she was a German teaching French in a one-horse town in central Illinois. I vaguely recall that one of her lessons was a knock off of what I thought was a British proverb. Here it is in la langue de Molière:
Le jeu est le fils de l’avarice et le père du désespoir.
However, I just read “Microsoft Lost $357 Billion in Mark Cap As Stock Plunged Most Since 2020.” That’s a big bet Satya Nadella made, and it has been working. Until now. Then I read “Microsoft Shares Dive as Data Center Spending Overshadows Earnings Surge.” Yep:
Le jeu est le fils de l’avarice et le père du désespoir.
Big bets. Big risk.
A wealthy professional is gambling at multiple games of chance at the same time. A crowd is watching, amazed that this person would play blackjack, run the slots, and hope that the roulette ball in on his wave length. Thanks, Venice. Good enough.
Now let’s put this swing for the fences strategy in the context of a run of the mill user. “Microsoft Is Working to Rebuild Trust in Windows” provides some consulting type lingo to the “experience” of using the world’s most popular operating system. That article offers:
Windows is at breaking point, and Microsoft knows it. Sources familiar with the company’s plans tell me Windows engineers are now focusing on fixing the core issues of Windows 11 over the coming months, in a process known as “swarming.” Microsoft is redirecting engineers to urgently fix Windows 11’s performance and reliability issues, aiming to halt the operating system’s death by a thousand cuts.
Let’s think about Microsoft and the interesting idea of “fixing the core issues.”
Microsoft is the juicy target for many bad actors. Some of the vulnerabilities have been known and exploited for years. In Tallinn, Estonia, I spoke with an advanced computer science class. One of the students said, “Yeah, Windows is pretty easy to exploit.” When was I in Estonia? How about 2006? The class was learning what flaws Windows had because it was a big, fat, floppy target.
Next let’s consider that Microsoft is using AI to code its different services. The only problem is that some of that code output by smart software has flaws. Humans may not be available to grind through the outputs searching for snipes. My recollection is that snipes were quite difficult to locate.
Also, consider that Microsoft has allowed interns, contract workers, real live on site programmers to add features and functions to Windows that demonstrate progress, commits, or innovations for the sole purpose of getting a raise, bonus, or promotion. I gave a lecture at Microsoft after which there was a reception. I spoke with a senior lead something in the Word unit. I asked if the word processor would ever include the type of numbering system used by the law firms with which I interacted. He said, “No. No need.” Right! No need. There were specialists like the little outfit in Charlottesville, Virginia, which figured out how to make Word number the way lawyers and courts want documents numbered. That little outfit made a lot of money selling its widget to law firms. Microsoft was right, “No need.”
And to end this list of issue, allow me to point out that the interface across the heavy lifting apps like PowerPoint and Visio is not normalized. Exactly how does one add specific tools to custom toolbar without first mastering the art of solving the Riemann Hypothesis? Microsoft tries but seems to lose sight of the duck it is trying to hit with its over engineered incentive system.
Now let’s think about the French proverb. My view is that Satya Nadella has gambled, bet a lot, and is now thinking, “Now what?” Investors appear to be thinking, “Yeah, now what?” With layoffs looming, some Microsofties are thinking, “Okay, now what?”
Talk about energizing Google and the makers of Linux distributions aimed at consumer computer users is amping up. Okay, Mr. Nadella, “Now what?” But more AI? Build more data centers and carry the cost of electricity so consumers are not burdened? Do the Elon thing and power the data centers with turbines or just install one of those July 2026 mini nuclear reactors?
This proverb is one that Madame Matthews might suggest you analyze in 500 words:
Le jeu est le fils de l’avarice et le père du désespoir.
Mr. Nadella is not playing one game. He is parallel betting. Does that reduce risk or increase it? Why not ask OpenAI?
Stephen E Arnold, January 30, 2026
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