Hobbledehoy / Jack Raines
Greetings, ladies and gentlemen (the term is to be applied anthropically)
Welcome to Serendipity.
If you are reading this for the first time, the loose premise of these musings can be found in the provenance email from August 2023, which, if you don't have time to read, can be summarized as a love letter to old friends and colleagues who have in some way made my life better, and to others who have made it suck.
(I see you reading this. Still creeping on me.)
In short, it's a newsletter from the pre-AI world where a person (me) would attempt to write something humorous and interesting, type it up, and send it to people.
I am actually considering making this a handwritten newsletter where I simply photograph a page from a notepad and text it to everyone. Let me know your thoughts.
Following last month's story, thank you to all those who offered arms sales, cyber attacks, satellite imagery, legal counsel, and political pressure to aid in my war against my neighbor.
As a quick update, the young couple's parents have now moved in with them and, quite mysteriously, the garden mess has disappeared and has not returned.
I will say nothing further and imply everything about this.
Since I frequently demonstrate my disdain for boomers who refuse to die quickly enough for my Costco visits to be completed in twenty minutes rather than sixty, today I would like to direct my thoughtfulness and astute observational prowess toward the generation that everyone seems to admire: Gen Z.
Recent studies suggest they may be the first generation to demonstrate measurable declines in cognitive performance compared to those who came before them.
This is deeply concerning news for Gen Z and deeply validating news for millennials, who have spent the last twenty years patiently waiting for scientific confirmation that they are better than everyone else.
As an undercover millennial, I am obviously delighted.
Unfortunately, most of us still spend six hours a day refreshing LinkedIn, watching YouTube videos about productivity, and arguing online about IPAs.
So perhaps the crown remains contested.
That said, I regularly encounter young people who describe Roblox as a pathway to engineering, communicate primarily through memes, and have somehow managed to turn "watching someone else play video games" into a legitimate form of entertainment and vocation.
Let's hope Gen Alpha wakes up and smells the whiskey.
My nephew Louis still seemed to prefer chocolate milk over Macallan 25.
Moving on.
This month's Serendipitous Moment comes courtesy of November's feature, Martin Bihl, and August 2024's feature, Michael Thompson.
The two have become such good friends through this strange little experiment that they are now launching an advertising not-for-much-profit venture together.
It is allegedly shrouded in secrecy.
As a result, I feel obligated to share the confidential website with all of you:
https:/failedcreatives.com/
Moving on, on.
This month I would like to introduce you to an exceptional Gen Z specimen. His name is Jack Raines.
Jack Raines
Jack is currently a vibe coder, blogger, influencer, AI slop cannon, and employee of a San Francisco venture capital firm where he appears to do "stuff."
Jack's work was recommended to me by someone I trust very much, who described him as "the funniest man on LinkedIn."
Naturally, I immediately followed him and began combing through his vast collection of observations about tech, money, ambition, and the modern business world.
Given that introduction, I was overwhelmingly underwhelmed.
His culturally relevant, technologically sophisticated jokes left me concerned that the future of comedy may be in serious trouble once millennials finally die off.
Then I met Jack.
And everything changed.
I quickly realized that his natural charm, wit, intelligence, and humor were being heavily compressed by LinkedIn's algorithm and the AI overlords working around the clock to make him less interesting.
Despite these youthful handicaps, he has become an overwhelming success.
He now speaks, writes, and conducts business at roughly a fourth-grade level.
His trophy is in the mail.
Jack has a new book coming out, and everyone on this list should buy it.
Then, the next time your child spends eight consecutive hours doomscrolling while claiming to be "building a personal brand," throw the book at them and yell:
"READ A DAMN BOOK."
Get it here.
You should also subscribe to his Substack here.
I am told the proceeds are used primarily to purchase food stamps for elderly people and maintain several endangered species.
Do not skimp on the donation.
And please follow him on LinkedIn here and engage with his work. We need more people making the internet slightly less awful.
For my friends from Stanford, MIT, Yale, Harvard, Oxford, Cambridge, and whichever institutions I forgot and will now hear about via email, please also check out Jack's etiquette school.
It is genuinely brilliant. See here
Once again, thank you for reading this letter from me to you. I appreciate you.
Yes, you.
I received zero unsubscribes last month.
Zero.
It was one of the most validating moments of my adult life.
For a brief period, I felt I had finally crossed the invisible line between persistent nuisance and welcome correspondence.
So if you are considering unsubscribing this month, I simply ask that you take a moment, reflect carefully, and remember that your actions have consequences.