Poor Jack's Almanack

I write about business, investing, and history. My writing:

[Poor Jack's Almanack @poorjacks_]

My favorite definitions of wealth are the ones that aren’t a number.

The definitions of wealth I like say something about the human condition or the desires of the person who abides by them.

My latest piece:

https://t.co/DuZ0GYY4LU

[Poor Jack's Almanack @poorjacks_]

@Jack_Raines Picking a spouse presents the death of optionality too.

Current generation is scared of commitment because the illusion of better alternatives has never been more prevalent.

[Poor Jack's Almanack @poorjacks_]

So much of Caro’s work style is innate to him and in that sense strikes me as impossible to replicate.

“Whatever it is that makes me do research the way I do, it’s not something I’m proud of, and it’s not something for which I can take credit - or the blame. It just seems to be a part of me. Looking back on my life I can see that it’s not really something I have had much choice about; in fact, that it was not something about which, really, I had any choice at all.” - Robert Caro, Working

[Poor Jack's Almanack @poorjacks_]

@TrungTPhan Yessir!

[Free Expression @WSJFreeEx]

Life offers no guarantees to anyone, but those of us who treasure Robert Caro’s books want assurances that he will deliver the final installment of his Lyndon Johnson series, writes @matthennessey 
https://t.co/LScBP1WK0A

[Poor Jack's Almanack @poorjacks_]

In so many ways Caro's work draws more from elements of fiction writing than traditional history.

He's telling a story, not merely reciting facts.

“If you want a work of non-fiction to endure, it must be written… the prose, the rhythms, the narrative style, le mot juste, that finding the right word must be at the same level as a work of fiction.” - Caro

https://t.co/52WDPJyk1c

[Poor Jack's Almanack @poorjacks_]

Runs so counter to the philosophy that Fred Schwab wrote about in Where are the Customer’s Yachts -

“Your average wall streeter, when faced with nothing profitable to do, does nothing for only a brief time. Then, suddenly and hysterically, he does something which turns out to be extremely unprofitable. He is not a lazy man.”

I wrote about this mindset and how it caused the Dallas Mavericks Management to trade away Luka, one of the best players of all time.

https://t.co/4YabX6TqQj

[Poor Jack's Almanack @poorjacks_]

@BoringBiz_ It's ironic how opposite the ideal skill sets for an entrepreneur vs. an investor are.

"Move fast and break things" - Mark Zuckerberg

"Inactivity strikes us as intelligent behavior" - Warren Buffett

[Poor Jack's Almanack @poorjacks_]

@SophieHaigney Loved this essay.

I wrote about seeing Dead & Co play in Golden Gate Park last Summer for those interested:

https://t.co/3ZCkJPuUHg

[Ray Padgett @rayfp]

Bob Dylan writing about Bob Weir in The Philosophy of Modern Song

[Poor Jack's Almanack @poorjacks_]

@almostcmb @WillManidis @InspiredCap https://t.co/cvsEITaW8a

[Jeremy Giffon @jeremygiffon]

I’m hiring an investor.

You’ll be the first hire working with me on the most interesting, complex and asymmetric special situations in tech.

You’ll be a good fit if you:

- trade annual letters like Pokémon
- are high pace and biased to action
- are unapologetically money motivated
- have created and sold a product
- ideological minority at a top 10 school
- debated risking it all with an SBA loan
- bought a stock before you could drive
- work in PE but long for higher MOIC
- work in VC but long for higher ROIC
- went through YC but yearn to invest
- can get a meeting w/ anyone on earth
- made money online in high school
- value heterodoxy over consensus
- value making money over being right

Steve Schwarzman defines eights as those who can follow marching orders, nines as those who can execute and strategize and tens as those can sense problems, design solutions, explore new directions and make it rain.

Eights and nines need not apply.

This role will have an equal focus on sourcing, analysis, execution and operations. In essence, you’ll wear every hat as we build the firm together. It will be all encompassing and demanding, but autonomous and yours to shape. You’ll invest and transact with the best operators and financiers in the world and produce work at an exceptionally high standard.

Experience acquiring technology companies, as well as operating them is highly prioritized but not strictly required. This role is open to all levels of seniority and will be made bespoke for the right person. In person in NYC only.

email me: [email protected]

[Poor Jack's Almanack @poorjacks_]

@readswithravi Ron Chernow - would never read a book on Mark Twain if it hadn’t been written by him.

[Poor Jack's Almanack @poorjacks_]

@paulg Jeeves is fantastic.

I included it on my top 10 list of 2025:

https://t.co/wwyyReC3i3

[Poor Jack's Almanack @poorjacks_]

@WillManidis Robert Caro once said “people don’t give enough force to the key role that character and personality plays in politics and power”. The trajectory of human events can be alarmingly malleable to the whims of human beings with great power, confidence, and flaws.

[Poor Jack's Almanack @poorjacks_]

@paulswaney3 Please send!

[Poor Jack's Almanack @poorjacks_]

My favorite books of 2025:

https://t.co/wwyyReCB7B

[Poor Jack's Almanack @poorjacks_]

@crasteel Thanks, Charles!

[Poor Jack's Almanack @poorjacks_]

My favorite definitions of wealth are the ones that aren’t a number.

The definitions of wealth I like say something about the human condition or the desires of the person who abides by them.

My latest piece:

https://t.co/DuZ0GYY4LU

[Poor Jack's Almanack @poorjacks_]

@david_perell Walter Isaacson
Michael Lewis
Would say Robert Caro but don’t want to distract him
Ron Chernow
Jason Zweig
Doris Kearns Goodwin
David Grann
Bryan Burrough
Rick Atkinson
Ted Chiang

[Poor Jack's Almanack @poorjacks_]

@david_perell I love these observations, especially the airplane tip.

New York is a magical place but certainly has its tradeoffs.

I wrote some of my own thoughts here:

https://t.co/ptMRsq2nGN

[Poor Jack's Almanack @poorjacks_]

@anukasan1977 There is a complete treasure trove in Charlie Rose’s archive, Richard Hefner’s The Open Mind archive, and Brian Lamb’s book notes archive.

World-class interviews for the public good.

Now I don’t think the audience interest exists.