No #194 | November 9, 2025

by Matthew Boyd

Good morning, welcome to the weekly Lead It Cool newsletter.

It's November, which means it's Movember, which means I'm growing a moustache, which means I'm making family uncomfortable while out with them in public. Please donate and support men's health.🥸

In this week's Lead It Cool newsletter:

• 🤖The Terminator
• 💡Life Lessons
• 😆Customer Reviews
• 😎Cool Links

🤖The Terminator

Terminator 2.

One of the greatest - maybe the greatest? - action films of all time.

I finally watched it with my son on Friday (his first time, I know, bad parenting), and his review was simple: “That was cool.”

Which, from a teenage boy, is about as high as praise gets.

Beyond being a timeless action masterpiece, T2 is also an eerily prescient commentary on the world of AI. When many of us think about artificial intelligence, we picture the Terminator, a conscious machine, and we often view modern AI developments through the lens of films like this.

One of the most eerie moments in the film comes when John Connor tells the Terminator to take care of some thugs.

The Terminator’s interpretation? Kill them.

John, horrified, quickly commands: “You can’t kill anyone!” It’s a striking reminder that tools are only as useful (and as ethical) as the humans guiding them. It’s the genie-in-the-bottle problem: the outcome is only as good as the wish.

It's along the same lines as the old story of King Midas. Granted one wish, he asked that everything he touched turn to gold. Seemed smart at the time, until he couldn’t eat, drink, or embrace his daughter without turning them into lifeless metal. His wish was granted perfectly, yet disastrously.

The problem wasn’t the magic, it was the clarity of the request.

AI is no different. The technology does what we ask, not necessarily what we mean.

Hasta la vista, baby.

💡Life Lessons

I was revisiting some of my weekly updates from 2023 and found an old list of "life wisdom" (source is Ankur Warikoo). Thought that I would reshare it.

💡Early in your career, you get paid for what you can do. Later on, you get paid for what you know.

💡In the end, every role boils down to how you deal with people.

💡If people can't trust you, it doesn't matter how smart you are.

💡Write your emails assuming they will be read by everybody.

💡If you cannot write down what you wish to say, you do not yet know what to say.

💡Spend more time appreciating people, than waiting for them to appreciate you.

💡Nothing makes you more indispensable, than doing what you committed to do, without anyone needing to check on you.

💡People are more willing to help, when they know you will still do most of the work.

💡Seek help with the problem early.

💡"I am a perfectionist" is the worst excuse for not getting work done.

💡It is much easier to be a commentator than a player. But its the players that everyone is watching!

💡Never trust your memory. Write everything down.

😆Customer Reviews

It's always strange the way our minds work when it comes to customer reviews. The wisdom of the crowd😆.

😎Cool Links

💸The Doom Spenders. Faced with an uncertain future, young Canadians are racking up more debt than ever before. Portrait of a generation on the instalment plan.

📶My Spreadsheet Doesn't Do That!. Here is a commercial from 1992 for Microsoft Excel. It's hard to believe we lived in a time before excel spreadsheets.

🎲Prediction Markets Are, Suddenly Everywhere. Wall Street Wants In. with sportsbooks, the house takes the opposite side of every bet, so it sets odds to balance money on both sides and lock in profit. Prediction markets don’t put their thumbs on the scale; they’re truth-seeking mechanisms that let users set prices themselves through their bets, producing odds that reflect the crowd’s, not the house’s, best estimate. That’s why some news outlets quote Polymarket odds; they (probably) better reflect sentiment than Vegas odds.

💌Share it on LinkedIn​

Thank you!

Let’s connect! 💬 You can find me on LinkedIn and Twitter