⛳Happy Gilmore (2?)

No #178 | July 20, 2025

by Matthew Boyd

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

"Deep summer is when laziness finds respectability." - Sam Keen

I heard this quote yesterday and let me tell you that for the past few days I've been looking very respectable🤪.

In this week's Lead It Cool newsletter:

⛳Happy Gilmore
🧠What Others Think of You
📚25 Pages a Day
😁Say Cheese
😎Cool Links

⛳Happy Gilmore

If you were to spend a couple of hours with me and my friends, the odds of hearing at least one Happy Gilmore reference would be sky high.

Whether it’s a casual “somebody’s closer…” or the iconic “how about a warm glass of shut the hell up?”, this film is forever part of our shared language.

Released in 1996, Happy Gilmore has become a cult classic, one that has somehow transcended generations as my kids love it just as much as I do.

This Friday, the sequel is being released on Netflix and, to be honest, I’m a bit nervous. I mean… how do you follow up perfection?

There are so many reasons the original Happy Gilmore has endured:

A truly great villain in Shooter McGavin (the smugness! the finger guns!)
A noble cause: buying back Grandma’s house
And of course, the unforgettable gimmick: Happy’s wild, hockey-style swing

But as I’ve rewatched the film, there’s one element that’s stood out more and more: the mentorship from Chubbs.

Happy’s relationship with his coach Chubbs, played by the late Carl Weathers, is what gives the movie its heart.

Chubbs saw potential in Happy before anyone else did. He gave him belief, discipline, and, most importantly, confidence. He taught him how to focus his rage, channel his energy, and find his happy place.

That’s the kind of support we all need in our corner. And if we’re lucky, it’s also the kind of supporter we can be for others.

A good mentor helps you play better. A great mentor helps you believe you belong.

And remember, it's all in the hips🤪

🧠What Others Think of You

I really enjoyed this article by Lawrence Yeo on The Problem of What Others Think.

This thought-provoking article explores the delicate balance between our concern for external opinions and the cultivation of our own self-worth and authenticity.

Here's my favourite part of the article:

Whenever we interact with someone – whether in-person or online – a gap emerges between who you are, and who you are presenting. This is why the person you are with your boss isn’t the same as the person on the couch watching Netflix. Or why the person you are with your best friend isn’t the same as the person you are with an acquaintance. Each relationship contains a culture of behavior that you oscillate between, which means that you’re constantly presenting a different version of yourself across a wide range of interactions.

What this means is that it becomes increasingly difficult to know who you really are. If a certain version of you emerges with this individual, but in the very next moment you toggle another set of behaviors with another, then that means your very identity is switching upon context. And the more you have to maneuver between various projections of yourself, the more difficult it becomes to get a handle on what “yourself” means in the first place.

This is why you’re likely exhausted after large social gatherings, and yearn to turn on the TV and watch something brainless until you drift off to sleep. The fatigue is not caused by the rigor in which your mouth is moving to talk, but rather by the constant switching of identity that occurs in these situations. It’s no surprise that alcohol is a feature of these gatherings, given that it helps to merge your identity into one unit for the duration of the night. Confidence is nothing more than the assertion that you know yourself, and alcohol helps do this at the expense of clarity.

📚25 Pages a Day

A great summer goal, especially for teenagers (🤪), is to read more. But if you're anything like me, following through on this goal can be challenging. I usually try to read before bed and then...😴😴😴

Farnham Street also recognizes this barrier, that's why they suggest setting the more specific goal of reading 25 pages a day.

25 pages a day equates to over 9,000 pages per year. Which equates to about 30ish books per year.

IMO, 25 pages is ambitious, so don't feel shame if you start with 5 pages/day (which is my goal).

Also, don't forget this:

😁Say Cheese

Dad joke🤣

😎Cool Links

👩‍🍳I'm a two-time tech founder. But restaurants are where I learned to lead. Restaurants don’t have the luxury of recurring subscription payments—they have to fight every day for every dollar of revenue. That reality pushed me to be data-driven and relentlessly hands-on. While some lessons didn’t feel obvious at the time, they guide how I lead in tech today.

🧠Mozart's Brain and the Fighter Pilot. The brain improves the more we challenge it. This is possible because the brain retains a high degree of plasticity; it changes in response to experience. If the experiences are rich and varied, the brain will develop a greater number of nerve cell connections. If the experiences are dull and infrequent, the connections will either never form or die off.

✍️Write Simply. Of course, fancy writing doesn't just conceal ideas. It can also conceal the lack of them. That's why some people write that way, to conceal the fact that they have nothing to say. Whereas writing simply keeps you honest. If you say nothing simply, it will be obvious to everyone, including you.

Trying to break your phone addiction, buy a methaphone. 😆🤔

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Lead It Cool - by Matthew Boyd

⛳Happy Gilmore (2?)

⛳Happy Gilmore

🧠What Others Think of You

📚25 Pages a Day

😁Say Cheese

😎Cool Links

🔥The Slow Burn

🎾US Open Rivalries

🧭Back to School