Poor Jack's Almanack

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: poorjacksalmanack.beehiiv.com/p/definitions-…

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. poorjacksalmanack.beehiiv.com/p/the-worst-tr…

This is good capital allocation, but it requires permanent capital. People don't actually want best returns. They want to feel clever and do some like weird little thing that makes them feel interesting or different or something. But sometimes you just got to do the obvious thing and just be really strong on it. I always admire those managers who have been paid 2 and 20 for like 40 years to just own Berkshire. It's awesome because they were right, and they were providing a service. The service is that the LP does not have the personal confidence to own Berkshire on their own. So they actually need to pay a huge premium for someone else to give them the confidence to own Berkshire. It's just a tax that they pay for not having the conviction to do it themselves. And I think that's great and solves a real problem for a lot of people.

@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

The best investors I know are all incredible poker players The best founders I know are all terrible poker players Lesson in there

@SophieHaigney Loved this essay. I wrote about seeing Dead & Co play in Golden Gate Park last Summer for those interested: poorjacksalmanack.beehiiv.com/p/me-my-uncle

My essay on why I love The Grateful Dead is in print today 🌹 nytimes.com/2026/01/17/opi…

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

@almostcmb @WillManidis @InspiredCap x.com/jeremygiffon/s…

@WillManidis @InspiredCap i don't know what that is, this was straight from the dome

For the first time in a very long time, we (@InspiredCap) are hiring an investor. We are a small partnership based in NYC focused on leading Seed & Series A and have raised ~$1b since founding in 2018. This person will work across the partnership and have the chance to interact with every part of the investment process. Beyond the obvious, here is some of what we are looking for: > Ridiculous levels of curiosity. You read everything. You use everything. Your desire to figure out how things work (and why) can never be satiated. > You believe that alpha exists at the intersection of disciplines and strive to connect the dots. > You are finance-literate but a technologist at heart. > You possess a quiet competence that enables you to proceed with limited direction. (You probably opted for a "create your own major" in undergrad if that was available). > You have a track record of making non-obvious life choices. > You love building networks and view the work associated with doing so as enjoyable versus a necessary evil. > You subscribe to a "work-life integration" world view If this feels like you (or someone you know), please get in touch.

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

Have you ever read a book by an author that was so good it made you want to read everything else they've written?

@paulg Jeeves is fantastic. I included it on my top 10 list of 2025: poorjacksalmanack.beehiiv.com/p/top-10-books…

If you resolved to read more this year, here are some particularly pleasing books: Master and Commander, Franklin's Autobiography, The Inimitable Jeeves, My Family and Other Animals, Wing Leader, Some Experiences of an Irish RM, A Time of Gifts.

@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.

we have the most individual leverage in history, yet everyone is choosing to live like they have zero agency by outsourcing the ordinary and gruesome (meat without the slaughter, profit without labor), we have lost our stomachs for the extraordinary, dirty, and necessary

@paulswaney3 Please send!

ASSOCIATE’S TOOLKIT Well the integration playbook ran Here is the actual end of the rope Comment, like, follow (so I can DM you) to get

My favorite books of 2025: poorjacksalmanack.beehiiv.com/p/top-10-books…

@crasteel Thanks, Charles!

@poorjacks_ very nice blog post, esp on Taleb!

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: poorjacksalmanack.beehiiv.com/p/definitions-…

@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

Who should I interview on How I Write?

@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: poorjacksalmanack.beehiiv.com/p/meandering-o…

I moved to back to New York 17 days ago, and here are some thoughts on the lifestyle here: 1) Manhattan is a place with lots of very good food for a “holy cow, I can’t believe I just paid that much for dinner” kind of price. 2) Nobody moves to New York to take it easy in life, and that determines a lot of the dynamics of the city. It’s a place you move to be somebody or do something. It’s not a place to coast. Or in the words of Taylor Swift: “Everybody here wanted something more” and “Everybody here was someone else before.” 3) The biggest problem with the subway isn’t slow speeds but the variance in travel times. This was captured well in a New York Times: “The subway is so late, it’s making New Yorkers early.” Why? Due to the variance, people need to leave early enough to account for the unpredictability of travel times, and when the subway shows up on time, they end up being awkwardly early for work. I wonder: how much should we focus on speeding up the subways, as opposed to reducing variance in travel times? 4) The vibrant social life is a positive externality of crappy housing. In most cities, people are content to hang out at home. But in New York, it’s so easy to get stuck in such a dungeon that you’re desperate to escape. Because of that, people end up socializing more than they would if the living quarters were nice. 5) Whenever I fly into LaGuardia, I’ll look at the landing patterns before my flight so I can sit on the side of the airplane that’s going to fly in with the best view of Manhattan, where landing airplanes fly over the city at an altitude of 3,500 feet. If the winds are from the south or the east, sit on the right side of the plane. If they’re from the north or the west, sit on the left side. When in doubt, pick the right side of the airplane. 6) One way to think about a city is how much making more money improves your quality of life. When I lived in Austin, I didn’t see how huge increases in my income would improve (or even change) how I lived very much. New York is different. Quality of life here correlates much higher to spending power, and this is one reason why New Yorkers are so intensely money-motivated. 7) Let’s use my first three apartments as an example. Each move was an upgrade not because I got more square footage or natural light, but because I wouldn't have to deal with as many mice. In my first place, I saw one every month. In my second, a few per year. By the third, they were gone entirely. And yet, through all that time, I swear I was paying more for rent than I would’ve paid for a mortgage almost anywhere else. 8) It’s much easier to get a good date in New York, relative to other American cities (and this is driven by the female-heavy gender dynamics). 9) Notice, though, how my emphasis was on the ease of getting dates in New York, for men at least. People here complain about the lack of commitment, and the sense that there’s always something (or someone) better right around the corner leads to that lack of commitment. 10) What New York gives you in volume of friendships, it lacks in depth. Of course you can cultivate deep friendships in New York, but I’ve found that the default mode is to be constantly meeting new people at the expense of seeing the same people over and over again. Mitigating this requires constant effort. 11) One of my friends is a tour guide who says there are six decisions that made Manhattan great: (1) the water system of 1842, (2) no steam engine trains south of 42nd street, (3) no steam engines in tunnels within the city limits, (4) no overhead powerlines, (5) the landmarks and preservation committee, and (6) Manhattan’s grid. All these are good rabbit holes to follow if you want to understand its history. 12) I agree with the first five, but have mixed opinions about the grid. Yes, it brought order and efficiency to Manhattan. And yes, it makes it easier for anybody (and especially people who don’t speak English) to navigate the city because they can deal with numbers instead of names. But I prefer the street life below 14th street, where the streets are narrower and more chaotic. Based on real estate prices, I’m clearly not alone. 13) New York will always have a monopoly on a certain flavor of American life: don’t own a car, walk most places, bike a lot, and have an abundance of restaurants and nightlife within a 1-mile radius — while also being an economic hub. There’s only one city in America where that combination exists, and it’s New York. 14) Something to know if you want to better navigate Manhattan: Even addresses on the south side of the streets and the east side of the avenues, odd addresses on the north side of the streets and the west side of the avenues (except for below 14th street where the grid breaks down). 15) As much as I enjoy the materialistic aspects of New York, I find spiritual life here to be incredibly challenging. There’s so much temptation and so much distance from nature, and the speed of the city makes it hard to cultivate the kind of stillness you need to hear from God. 16) Always, always ask: “Why is it called that?” For example, the name ‘Manhattan’ means “island of many little hills.” There are two things to take from this. The first is that Manhattan really is more hilly than you’d think. But at the same time, for a place of that name, it’s surprisingly flat because New Yorkers dynamited most of the hills away. Whatever hills remain are now man-made skyscrapers, not God-made land. 17) People make fun of New Yorkers for praising the new bike lanes, but the excitement people have about them is a reminder that if you want to improve street life, you just need to get rid of cars and give people cozy places to walk. That’s how low the bar is for urban design these days. 18) An easy way to improve your quality of life in New York is to build the habit of ordering ahead whenever you go to a take-out lunch spot. The restaurants in town make it easy to order ahead now in ways that weren’t possible a decade ago (and because of TikTok, the lines are as long as they’ve ever been). 19) Somebody on here said something recently that I can't stop thinking about. I've lost the tweet but it was something like: "TikTok is doing to New York what YouTube did to Los Angeles ten years ago." 20) New York has a way of feeling like it’s the entire world like no other city I know. One of The New Yorker’s most famous covers is about exactly this (see the photo below). 21) As much as I enjoy the materialistic aspects of New York, I find spiritual life here to be incredibly challenging. There’s so much temptation and so much distance from nature, and the speed of the city makes it hard to cultivate the kind of stillness you need to hear from God. 22) New York and San Francisco have different ways of thinking about work-life balance: In New York, you work your tail off when you’re at the office, but it’s relatively easy to disconnect on the weekends. In San Francisco, even though I don’t sense the same temptation to work so hard that you have lunch at your desk, there’s a way your job dominates life more there. People take company buses to / from work, tech companies have gyms inside their HQ, and even the weekend social events feel work-related (even if you’re technically off work). There’s a reason that a book like The Circle takes place in the Bay Area, not New York. 23) New York is a cultural and economic capital, but not a political one. That seems obvious now, but it wasn't inevitable. New York was once the capital of the United States. And if Washington hadn't taken that title, New York would be a far more political city that's more tethered to the past and filled with military statues.

@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.

When I was growing up, PBS was for educational kids’ shows, ballet, opera, & highbrow news. TLC was The Learning Channel—with smart educational content. Discovery Channel was all science & tech. History Channel was Kenneth Clarke, James Burke, & Ken Burns-tier stuff. Now…

@ankurnagpal Guide!

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@amandafortini Anthony Bourdain case in point.

A lot of people just travel constantly to avoid themselves.

@BigJohn043 Makes sense - appreciate the reply!

@poorjacks_ That math is surprisingly hard to do. But the short answer is that our whole investment strategy is buying unsophisticated founder led business and turning them into PE backable growth engines. So we get a ton of multiple arb but it is pretty repeatable....

I am not sure I agree with the idea of PE market saturation. But I totally agree that you need to understand how the firm that you are going to join makes money. And if they don't have a consistent process to produce alpha it is going to be tough. I would also argue that it is very difficult to differentiate yourself as an "investor". Enough people all do the same thing that any differentiation here is going to be competed away fairly soon. Alpha is generated by being a better "owner". Knowing how to drive and help portcos grow. The interesting thing here is PE shops all do this pretty differently. And it isn't an easy thing to learn or to copy....

Wild fact about F. Scott Fitzgerald - a half century after his death, more of his books were sold in a single year than the entirety of his life.

@tferriss @davidsenra I wrote about this! poorjacksalmanack.beehiiv.com/p/anti-capital…

NEW podcast episode is up! David Senra — How Extreme Winners Think and Win: Lessons from 400+ of History’s Greatest Founders and Investors (Including Buffett, Munger, Rockefeller, Jobs, Ovitz, Zell, and Names You Don’t Know But Should) Please enjoy! 🙌 cc: @davidsenra @FoundersPodcast