No #199 | December 14, 2025

by Matthew Boyd

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

Firstly, happy anniversary to my amazing and incredible wife, Valentina. 18 years! It's been an incredible adventure and I'm so blessed to have you in my life.💗

Secondly, significant programming update: As I approach my 200th (!) weekly newsletter, I've decided to take a hiatus from writing Lead It Cool for a little while to put some focus on a couple other creative side projects that I've been procrastinating on. So next week will be a special 200th edition and also my last one (for at least a little while). More to share next week 😎.

And thank you again to everyone who reads these and joins me in my weird little corner of the internet every week.

In this week's Lead It Cool newsletter:

• 🤩Standing Out
• 🤔Why People Buy Stuff
• 😆Circle Back
• 😎Cool Links

🤩Standing Out

’Tis the season for a proper holiday cocktail.

And if you’re hosting (or just pretending you are) nothing pleases a room faster than an Old Fashioned.

You know the drill.

Grab the bourbon.

A touch of simple syrup.

A couple dashes of Angostura bitters.

And then… pause.

Why does the label on the Angostura bitters bottle never fit the bottle?!?

It’s absurd. Oversized and lacking any cohesion or symmetry.

Turns out, it’s not a mistake. It’s a happy accident.

​Back in the late 1800s, Angostura entered a bottle design competition. One team designed the bottle. Another designed the label. They didn’t compare notes. When everything was assembled, the label was clearly too big, climbing awkwardly up the neck like it had somewhere better to be.

The company had a choice: reprint the labels or roll with it.

They rolled with it.

And that weird, mismatched label became the thing. Bartenders remembered it. Drinkers recognized it instantly. In a world of elegant, symmetrical bottles, Angostura looked… different. And different stuck.

Today, more than a century later, they still haven’t “fixed” it, because it was never broken. The oversized label is the brand.

So the moral of the story?

If you want to stand out, don’t blend in. Wear clothes that are several sizes too big for you😆. Even better if you’re holding an Old Fashioned while you do🥃.

🤔Why People Buy Stuff

Really love this summary on what motivates people to buy anything (source).

Really helps focus any marketing strategy. Some wisdom too that a mentor once reminded me: "Everybody is in sales".

😆Circle Back

It's the most wonderful time, of the year...😆

😎Cool Links

🏈Why a simple act of appreciation explains Mike Vrabel's leadership style. Patriots coach Mike Vrabel is hard on his players, but after every game, win or lose, he greets them alone in the tunnel and thanks them.

🤔From Crisis to Renewal: What Disruption Taught Me About Leadership. Disruption is no longer episodic; it is the environment in which we operate. Technology, geopolitics, climate shocks, and shifting expectations have made uncertainty permanent. The real question is no longer whether a crisis will come, but who we become when it does.

👏In-N-Out nixes '67' from ticket system due to '6-7' trend. If you have children in your house, you will completely understand this headline 😆.

😆How to get a workout in while you're eating (barbell utensils)​

💌Tell a friend to subscribe​

Thank you!

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