Buy Your Copy of Young Money!

The last couple of weeks were, to say the least, pretty wild. Highlights include, but are not limited to:

• Appearing on Scott Galloway’s podcast, not just once, but twice (and facing accusations of being a nepo baby from the comment section).

• Chopping it up in the Bloomberg HQ with Barry Ritholtz.

• Renting the NASDAQ for a day.

• Seeing my physical book in the Barnes & Noble by my apartment.

• Receiving dozens, if not hundreds, of emails from total strangers who loved the book.

Writing a book is hard. Seeing it in the world is cool. I will, over the next few weeks, share more details on both the book writing and book marketing process, as it’s a unique experience that’s tough to understand until you’ve gone through it yourself.

But for now, I want to focus on one particularly funny concern I had while going through the book promotion process: I wasn’t entirely sure how to “describe” my book when telling people what, exactly, it was.

Calling Young Money a “memoir” felt weird, as “memoirs” seem to be written by silver-haired business magnates reflecting on their professional endeavors or immigrants who survived their treacherous journeys across raging seas in homemade rafts to reach a better life.

So my elevator pitch usually settled into some version of, “Life advice for 20-somethings,” which, I guess, is directionally correct, but it also just comes off as dry. And, as I hilariously realized later, this description alienates anyone older than a 20-something. I received at least 15 emails last week from folks saying some version of, “I was really looking forward to reading your book, but I figured that I’m too old to learn anything from it since I’m 33.”

After replying to the 15th email saying that this book was written about my 20s, but it does not at all exclude all of the non-20-somethings from reading, enjoying, and resonating with it, I realized I probably need to clarify what, exactly, Young Money is for those who haven’t read.

Young Money: A Field Guide to Wealth and Purpose in Your Twenties is a memoir about my conflicting desires for achievement and adventure in the brief window of post-college adulthood, and my reflections on that period as I approach 30.

Young Money is not, as I have sometimes called it, “life advice for 20-somethings,” though many folks have since deemed it “essential reading for 20-somethings.” Young Money is the story of my struggle to strike a balance between the pursuit of “fun” and the pursuit of “success,” and my reflections on that period of life.

Five years after launching this blog, I’m stoked that Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is finally available for purchase! Buy your copy below:

Buy your copy of Young Money!

“Advice” tends to be pointed, narrow, and in the year of our lord 2026, outsourceable to an LLM.

Stories, however, are invaluable, because they’re relatable. A good story makes the reader feel seen and understood because it reveals a piece of their own nature through the experiences of someone else. Young Money is a story of a young man trying his best to make the most of his twenties before they were gone, a tale as old as time.

And judging from early readers’ messages, that story had wide appeal. Young Money sold thousands of copies in its first week, and I’ve received 100+ messages from readers who finished the book. From those 100+ messages, two groups of folks seem to really like the book:

1. “I’m somewhere between ~18 and 30, and this encapsulated exactly how I’ve felt but I didn’t know how to put into words. Thanks for sharing your story.”

2. “I’m in my 40s - 60s, so I didn’t think I was the target audience, but your story took me back to my youth. Thank you for writing it. I’m buying copies for my kids and my friends kids.”

Screenshots from folks younger than me:

Screenshots from folks older than me:

Why share all of this? Well, first, I’m happy that Young Money has some real traction, and it’s fun to share reviews from the crowd. But more importantly, I wanted to highlight that, while the book might be marketed toward 20-somethings, it’s certainly not only for 20-somethings. Young Money isn’t self-help. It’s a story that some folks might find immediately relatable, but a lot of folks, across all ages, have found valuable.

A couple of other things:

A lot of college students and recent graduates have reached out saying they want to buy copies for their friends as gifts, and I’m now speaking to ~75 students at NYU next month, with events lined up at Columbia Business School and Harvard Business School as well. Given that college students are now going back to school, I want to get Young Money in as many of their hands as possible.

If you’re a college student or employee in a leadership role in Greek Life, athletics, student government, investment clubs, or other organizations on campus, and you’re interested in placing a bulk order of books and/or also want me to speak to your organization, shoot me an email.

Similarly, if your company employees lots of recent graduates, and you think Young Money would be a valuable read for your employees just entering the work force or considering their “next” job, shoot me a note, because I’d love to send you some copies.

And if you’re my age or older, and you already survived that internal conflict in your youth, I think you’ll enjoy my story, and it’s worth checking out as well. Memoirs are so much more fun than “advice.”

As always, thanks for reading and have a great week.

- Jack

Buy Your Copy of Young Money Here!

And make sure you leave an Amazon review :)

Buy Your Copy of Young Money!

There was, I believe, a time where the publishers, as well as a select few networks, magazines, and newspapers, could move the needle on a book. When there are five national newspapers, two relevant late night shows, and a handful of magazines that really matter, all it takes is one editor or journalist to care about your work and, suddenly, everyone cares about your work.

Publishers would identify and partner with talent, then they would work their network connections to get said talent’s work on the biggest stage possible. The artist’s job was to create. The publisher’s job was to platform the artist.

The internet changed that.

Suddenly, five national newspapers, two relevant late night shows, and a handful of magazines that really matter gave way to thousands of micro-blogging sites and web forums. Attention, which previously coalesced around a few central networks, was decentralized across the web. Still, I would argue that the early internet benefited many writers and creators: you could now build your own blog, forum, or some other platform to aggregate attention from like-minded individuals, and you owned the real estate.

Then social media really changed that.

Suddenly, a thousand different fiefdoms, from pickup artist chatrooms to weightlifting forums to personal cooking blogs, gave way to the “newsfeed.” A web of a million nodes collapsed to a new set of centralized platforms. But unlike the earlier regime, where Howard Stern, Oprah, The New York Times, and The Wall Street Journal, CBS, and ABC determined the storylines that we all cared about, “the newsfeed,” which became the de facto interface of Facebook and Twitter, was a never-ending carousel of “new thing” after “new thing.” You could build on top of the carousel, of course, but you never owned the carousel, and you never controlled the carousel. And as the carousel shifted away from follower-first content to algorithmically-driven content, you couldn’t be sure that your “followers” would see your content.

This, of course, led to what would become “trend-hacking,” where savvy marketers would chase and exploit hot “social media trends” to capture fickle attention before the game inevitably changed again.

And now, AI has only accelerated the discoverability challenge first introduced by the newsfeed. While an algorithmically-driven newsfeed dilutes the connection between the follower and the followed, the act of “creation” did, until ~two years ago, require effort on behalf of someone. Writing a blog post, even a “bad” blog post, took time. So did making a video, or simply engaging with folks in the replies.

But now you can just voice-to-text some rambled thoughts to ChatGPT / Claude / Grok and ask your favorite LLM to “craft an attention-grabbing LinkedIn post on this topic,” and 30 seconds later, you can pollute the newsfeed with your ClaudeSlop. And, of course, in the age of “building personal brands” where “everyone wants to be an influencer,” there are plenty of incentives to use AI to accelerate your content throughput, which means that other folks, competing for the same attention, will also leverage AI to accelerate their content throughput, which means the sheer amount of “content” being produced is growing exponentially.

But our capacity to digest “content” hasn’t grown. Whether the number of new social media posts per day is in the thousands, millions, billions, or trillions, humans only have 24 hours, a subset of which can be spend focusing on any particular “thing” online. Combine this onslaught of “slop” with a decentralized internet where my newsfeed is different from your newsfeed is different from our mutual friend’s newsfeed, and breaking through the noise is harder than ever.

40 years ago, the artist’s job was to create, and the publisher’s job was to platform the artist. In 2026, the artist must both create and platform themselves. A publisher cannot, on their own, “platform” a promising artist in 2026 because attention is no longer centralized. There’s no single “show” or “publication” that, upon covering your work, will lead to you being “GOATed.”

No, in 2026, you, the artist, must somehow convince some subsection of the internet to care about what you have to say. But how could another endpoint in the metaverse possibly care about what you have to say if they’ve never heard of you in the first place?

The artist, therefore, must now fulfill three roles.

Can you make your work known?

Can you make those who know your work care?

Can you make something worth caring about?

Writing a book is hard. It’s a year-long, mental wrestling match with yourself. You finish a chapter, take a deep breath, and another blank pages taunts you. “50,000 words to go. Good luck.” Of course, you’ll have to revise the prior chapter another 10 times, but you can deal with that later. For now, it’s on to the next one. And you do this over, and over again. You read the same words several dozen times, to the point you can’t possibly tell if it’s even “good” or not. And you don’t know if you can trust friends who read early samples, because would they really tell you if your writing sucked? And you’re stuck in this loop for a year.

Candidly, I underestimated just how difficult it would be, and I understand why the vast majority of books, particularly nonfiction books, are written by ghostwriters. It’s tough.

The nice thing about book advances, however, is that they create a powerful forcing function for actually writing a book. Something about receiving money that’s subject to being contractually clawed back should you fail to turn in a manuscript is quite motivating, particularly after you spend part of your first advance payment on a new watch. And then, upon turning in that manuscript, you unlock the rest of that advance, which is, of course, quite nice. When I first saw that book advances pay out in tranches, I was confused. “It’s an ‘advance.’ Shouldn’t I get it all up front?” Now, I think tranches make a lot of sense. Give enough money upfront that the author feels some reward (and understands the stakes of having to pay it back if they can’t deliver), backload the rest as an incentive to actually turn in the work.

But I think some writers misunderstand the purpose of the “book advance.”

There’s a romanticized view that I imagine some folks hold of the author as an “artist,” and the advance is a patronage to support this artist’s endeavors. “Here are dollars for your labor.” But that’s an incomplete understanding. While, yes, the author does keep their advance assuming that they turn in their completed work, that advance is, really, an investment from the publisher. “Here’s some money to write a book, we expect to earn that money back, and then some, from the eventual sales that result.”

A joke I’ve made a few times now that’s actually not at all a joke is that the relationship between publisher and author is akin to that of venture capitalist and founder, which is, of course, ironic, given that I sit in the “receive capital” seat as an author and the “invest capital” seat as a VC.

Early-stage venture capitalists might invest in 40 companies per fund, knowing that 50% will be 0s, 30% will return their original capital, 25% will make “some” money, and 5% will generate 90%+ of your returns. Power laws dominate the venture capital game. But they also dominate the publishing game.

Depending on the fee split, Avery Publishing has probably made $150 million+ from Atomic Habits alone since it was published in 2018, likely dwarfing the rest of its portfolio combined. Avery likely has dozens, if not hundreds of books, that cap out at a few thousand sales. But it doesn’t matter. Atomic Habits will make them millions of dollars every year, forever.

Books with early traction (not to be confused with the gamified “book launch” playbook so many folks run with shadow bulk buys to game the NYT ratings, where 50,000 books are purchased but never-once opened) that experience a “virality loop,” where enough early readers tell other folks about it to the point that the book remains popular beyond it’s initial launch window, gain “staying power” that increases with each launch cycle that the particular book survives. Put simply, books are subject to the “Lindy Effect.” The future relevancy of a book is proportional to how long it has remained relevant.

Atomic Habits will always be a best-seller because it’s always been a best-seller. The same is true for The Psychology of Money, The Subtle Art of Not Giving a F*ck, 48 Laws of Power, and other books that remain at the top of the best-sellers list year after year. Ironically, I think the slopification of the internet benefits proven winners at the expense of new releases. Why? A couple of reasons.

First, readers have information overload. When you’re bombarded with billions of inputs vying for your attention, you’ll default to the “proven thing” that minimizes your own cognitive load. If you look for best personal finance books on Amazon and see The Psychology of Money, and you remember hearing a few folks recommend it on a podcast two years ago, you’ll buy The Psychology of Money. Why waste time looking further down the list.

Second, LLMs are becoming society’s primary information retrieval vector. LLMs, which were largely trained on internet data, tend to refer readers to those books which appear to have appealed to readers asking similar questions. Therefore the best-sellers in particular categories will be pushed out as responses to new prompts over, and over, and over again. Remember, the LLMs haven’t “read” the books, they’re pattern matching on their training data. AI is a flywheel for proven winners and a roadblock for new entrants.

Back to book advances.

Advances are investments, that, granted, the author keeps regardless of the book’s ultimate performance, and they do help subsidize the author’s life as they work on the book. But publishers give authors advances with the expectation that some of their books will become perennial sellers, like Atomic Habits, more than paying back the investments not recouped from other books that underperformed.

While, as a VC, we don’t expect every founder and portfolio company to make us money, we invest in a founder reasonably believing that they will work very hard to build a big business, and, if they succeed, both parties benefit and make bank.

I don’t think a lot of writers look at the book process this way, because I think they have an archaic view of the publisher / author dynamic. If you still believe that the sole job of the author is to create something great, and that if your “thing” is great enough, some combination of publisher efforts and the broader universe recognizing your greatness will reward you with book sales… I have some waterfront property in Kansas to sell you.

The goal of the writer is the write something worth caring about, yes. Of course. That’s never changed. But you also have to convince people that you wrote something worth caring about, and to do that, you have to show people that you’ve written something worth caring about. Which, yes, means that you have to market your book. You have to hustle. Every job, at the end of the day, is a sales job. That’s especially true in the arts, though I think many artists view themselves “above” sales. “I spent my time and effort building something great, shouldn’t people just buy and appreciate it?” But that’s not how the world works. That’s not how the world has ever worked. Taking an aristocratic view of the world might make you feel “above” the hustle, but it won’t translate to book sales.

There’s a reason that companies have sales teams and engineering teams, and the top sales talent out-earn everyone else at the company: someone has to convince someone to buy your B2B SaaS, I can assure you that no one gives a shit about your agentic harness or model orchestration, but a good sales rep can change that.

The writer, unlike a company, has to both build the product and sell it. Which I’m fine with. My perspective on this is simple: someone gave me money to write a book with the implied expectation that some of the books they invest in will make them money. I would like to hold up my end of the bet and deliver, or at least give my best effort to do so.

Five years after launching this blog, I’m stoked that Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is finally available for purchase! Buy your copy here.

If you aren’t working as hard to sell your book as you did to write it, you’re leaving chips on the table, and you’re treating a publisher’s advance as a patronage you were owed rather than an investment that you can leverage.

My perspective is that if you call yourself a “writer,” and you’ve poured year(s) of your life into a creative project, and that project is now complete, and you’re proud of that project, you are doing yourself a disservice by not pouring all of your efforts into giving that project maximum exposure. I have a few thoughts on why writers hesitate to promote their work.

Perhaps they find “marketing tactics” to be gauche, tacky, or insincere. This is, of course, stupid. Marketing always has been, and always will be, a crucial ingredient for success in any domain, and this is particularly true in the arts. But also, one year later, no one is going to care about your “marketing tactics.” They’ll just see the sales numbers and reviews.

I also think some folks, particularly introverted folks, hate “bothering people” about their work. To this I say that if you’ve spent hundreds, if not thousands, of hours, refining your project, you owe it to yourself to tell everyone you know about that project. It’s an act of disrespect to the work you put in to not knock down people’s doors to have them read your book, listen to your song, or watch your film. You’re worried about “bothering people” to the point you won’t send them a text or email? At worst, they won’t reply. At best, they might be moved by your creation, they might feel that you encapsulated an idea they had always felt but could never put into words, that they’ll thank you and refer your work to 100 others. And you never know which individual your work will truly resonate with. By not aggressively marketing your work, you’re depriving someone who needed to read it because of your fear of “bothering” someone who will glance at your text for two seconds before continuing on with their day.

Self-promotion of one’s work is an asymmetrical bet: no one is going to be “mad” that you “bothered” them by sharing your work. Do you realize that most people think caring is cool? Seeing someone so fired up about their thing that they can’t shut up about it is inspiring, even if I couldn’t care less about their particular thing. If you can’t be bothered to tell the world about your creation, why the hell should anyone else care enough to read it? You don’t know who needs to read what you wrote, but if you truly believe that there is a group of people who would benefit from your work, it’s your responsibility to maximize the surface area by which they can discover it.

But I think the real reason folks don’t take marketing as seriously as the creative process itself is that they’re hedging. When you spend year, after year, working on a particular thing, and it’s done, your identity becomes tied up in that thing. You likely think more, or less, of yourself depending on on the success, or failure, of that thing.

By not going all-out on marketing, you maintain a layer of self-preservation. If the book doesn’t become a best-seller, it's not necessarily because the book was “bad.” You can tell yourself that the algorithms were just working against you, or the “best-sellers” were all fake, anyway. Just a bunch of bulk orders orchestrated by “authors” with money! Ironic detachment becomes self-medication. By not committing to promotion of your work, you avoid rejection.

The artist who refuses to promote their work is like the 25-year-old guy at the bar who hesitates to approach the cute girl across the room: you withhold effort because effort makes you vulnerable to rejection. But lack of effort doesn’t protect you from rejection, it simply ensures that you remain in the same place that rejection would send you. If you don’t approach the girl, you won’t go out with the girl. If you do approach the girl, you might get curved, or you might go out with the girl. The future is uncertain, but it’s only the risk-taker who has a chance to reap the rewards.

If you don’t promote your work, your work won’t be rejected. But it won’t be accepted, or even acknowledged, because no one will know about your work. You are cementing your own irrelevance, which, again, if you’ve spent years working on thing, seems like an act of disrespect to yourself and your publisher.

But don’t get me wrong, I get it. My book came out last Tuesday. I was quite, quite anxious before launch. What if no one cares? What if it sucks? How do I even know if it’s good, at this point? But I wrote something that, to me, mattered. And my bet was that there were other people like my who would feel similarly, and it was my job to help them discover what I wrote. So I’ve been on a self-promotion tear.

I sent out more than 100 early copies to different folks with their own platforms who I thought would appreciate, and resonate, with my work. Many of them read my book. Some didn’t. But some portion of those folks who did read what I wrote loved it. You can tell, from when someone talks about your work online, if they endorsing my book because they “like Jack” and want to support (which, of course, I appreciate), and when my book really, really, resonated with them. And it’s only going to be some minority of folks with whom any particular work will truly resonate. You have to find the right person at a time in their life where a particular paragraph or passage really hits. But when you find those nodes, And they feel moved by your work to the point that they leverage their own platform and reputation to promote your work, the ripple effects are exponential. A couple of examples from my launch:

• I sent an early copy to an anonymous Twitter account, “Blueprintsmb” that I quite like. He has ~20k followers. Not a huge audience, but a decent size. But he has a great story: Korean guy who grew up poor in Kansas, made his way to Wall Street, made some in the hedge fund game, burned out in his late 30s / early 40s, bought a manufacturing business in New Jersey, and now tweets about his lessons learned on Wall Street and as an entrepreneur, and how he thinks about the life tradeoffs of high-stress, high-pay W-2 work vs. running your own business. I’ve never met this guy, but we’ve DM’d a few times. He has now tweeted about my book several times, unprompted by me, to the tune of 100s of thousands of views, and many of his followers are my target demo:

• Another example is my buddy Michael Smoak. Smoak has amassed an insane following: several million folks across TikTok and Instagram under his handle “higherupwellness.” His content is a mix of fitness and broader life advice for younger folks, and he has increasingly leaned into the latter. Like with everyone I sent early copies to, I was hoping for some sort of repost or story shout out, but he actually dug into the book, loved it (we were texting back and forth about the opening chapter as he was reading it), and then published a full video on Instagram and TikTok endorsing the book, generating hundreds of thousands of views.

Again, I had no idea which folks I sent early copies to would love it, endorse it, repost something generic about it, or totally ignore it. That’s true of marketing quite literally anything. But guess what? Some of those folks did love it, they endorsed it, and my surface area grew accordingly. And a couple of days post-publication, the validation started rolling in.

There are a few people I personally DM’d or emailed after reading their books to express my appreciation. A couple of examples:

Morgan Housel, ~six years ago, after reading The Psychology of Money. This one was particularly cool, given that, six years later, he was one of the blurbs on the back of my book:

Rolf Potts, ~four years ago, whose book Vagabonding, was the impetus for me traveling abroad in 2021.

Given my own experience as a reader, my test for “how do I know my book is good,” is whether or not people I’ve never heard of will reach out to me after reading my book. The goal is write something that moves someone. The evidence that someone was moved was that they’ll tell you. Anyway, here’s some messages I’ve received in the last three days:

This is a small sample, but you get the idea. I’m happy to say I’m passing my own test; hopefully it keeps compounding. The takeaway here, if there is one, is that caring is cool. Taking risks is cool. Self-promotion, if your product is “good,” is self-respect. People deserve to hear about it.

Anyway, buy your copy of Young Money, and make sure to leave a review.

- Jack

Buy Your Copy of Young Money Here!

And make sure you leave an Amazon review :)

Buy your copy of Young Money!

THANK YOU, THANK YOU, THANK YOU. Young Money went live Tuesday, and the last 48 hours have been insane. The Barnes & Noble by Union Square in Manhattan was sold out, a friend texted me that the bookstore in San Francisco’s Marina District was sold out, and I’ve received hundreds of texts, tweets, messages, and posts about the book. People seem to love it. To everyone who purchased and / or posted about the book, THANK YOU.

Thanks to you, Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is currently Amazon’s best-selling new release in personal finance, the #2 new release success and self-help book behind Tony Robbins, and the #4 on all personal finance books (not just new releases!) on Kindle, ahead of Die with Zero and Rich Dad Poor Dad.

Not bad!

Oh, I also wanted to share my favorite feedback email so far:

“Never heard about you before but you are actually pretty based.” Is probably my favorite endorsement I’ve received from a stranger, so thank you Cyrus for the promotion.

48 hours in, I couldn’t be happier with the book’s reception, but I have two lingering thoughts: You know what’s cooler than being second to Tony Robbins in the self-help charts? Passing Tony Robbins. And you know what’s cooler (and more ambitious) than passing Tony Robbins? Shooting for the New York Times’ list.

The key to both: selling as many books as possible. I think both are doable, but I need your help. So I have a few asks:

• If you haven’t already, could you order a copy of Young Money? (and if you bought it and loved it, order copies for your friends, families, and students!) If you’re already on my mailing list, and you like Young Money the blog, you’ll love Young Money, the book. Whether you’re 21 staring down college graduation, 28 and facing a career inflection, or 55 and reflecting on the past 30 years, I think you’ll find that my work resonates. Order from your local bookstore or Amazon below:

Buy Young Money from a Local Bookstore

Buy Young Money on Amazon

• If you’ve read Young Money, could you leave an honest review on Amazon? Amazon, like social media apps, is algorithmically driven, and the two things that move the needle are 1) book sales and 2) reviews.

Leave an Amazon Review here!

• If you think other folks in your life should read Young Money, share the book with them! (and feel free to send them the Amazon link).

• If you really liked Young Money, toss a post with the book cover, a screenshot of your favorite passage, or your takeaways on X, Linkedin, or Instagram and throw me a tag! I’ll make sure to repost.

Thank again for buying, reading, and supporting. Let’s mog Tony Robbins together.

- Jack

Buy your copy of Young Money!

And make sure you leave an Amazon review :)

Buy your copy of Young Money!

A story from last summer:

While briefly living in the CitizenM Bowery Hotel, I lost approximately 15 pounds due to stress in the ~2 weeks between June 25th and July 8th.

Some context: I moved to San Francisco in January 2025 for a new job, and, at the time, one of my goals while in San Francisco was to write the first draft of Young Money before returning to New York for the summer.

My schedule for the first five months of 2025 was simple: work (and try to figure out how to ‘do’ venture capital) during the week, then write from 6 PM on Friday until 10 PM on Sunday, then rinse and repeat. I, surprisingly, stuck with this schedule pretty consistently, and I was confident that I would finish draft one by mid-June, with a couple of weeks to spare.

Finishing draft one by mid-June would have been ideal. After spending the first half of the year on the other side of the country from most of my friends and family, I was looking forward to a few weeks in my New York apartment before my lease ended (I had subleased my room to a friend for four months when I moved to San Francisco), then a trip to Ibiza and Mallorca with my best friends, then a month working from an Airbnb in East Hampton with five friends before flying back to California in August.

Then I experienced a canon event familiar to all authors: On May 28th, I stared at my manuscript in disgust and thought, “This writing sucks.”

When you’ve published something like 1,000,000 words via blog posts, covering everything from philosophical musings on the role that entropy plays as life’s antagonist to debaucherous antics from my time at The Rising Cock Hostel (seriously, this place is awesome) on the southern coast of Portugal, writing a 60,000 word book doesn’t seem all that intimidating. But the complexity of a book, I quickly realized, scales exponentially, not linearly, with length.

After five months of cranking away on this thing, I hated the product, and I had less than one month to rectify that problem.

I convinced myself that I could work overtime in the first two weeks of June until my revisions yielded a satisfactory product, but after 12 days of waking up at 6 and going to sleep at midnight to aggressively write and rewrite, I still hated it, and I realized I was going to have to restructure something like 85% of the book to get it where I wanted it over the next few weeks.

“But how are you going to revise that from Spain with your friends?” I asked myself. The answer, of course, was that I wasn’t. So I texted my friends and said, “Hey, so I’m out on the trip.” I had already taken the time off work, so I knew I would have ~12 uninterrupted days to do nothing but write, which was just what I needed. A few other logistical nightmares at play in mid-June:

• My lease was ending in four days, meaning that I was going to be homeless during a window in which I had planned to be out of the country.

• At the end of those 12 uninterrupted days, I had to fly to Georgia to pick up a vehicle to drive back up to New York, at which point I would have to go back to work, meaning that I couldn’t extend my self-induced writing retreat longer than 12 days.

• I was mid-fallout with a girl I’d been seeing, which, as we all know, feels like emotional seppuku.

With this as a backdrop, I tossed all of my clothes in a few suitcases, booked a room at the CitizenM with a nice view of the NYC skyline, and spent 22 out of 24 hours (excluding meals in the restaurant downstairs and the occasional trip to the Equinox across the street) in that hotel room, either sleeping or writing, with my phone locked away under the bed.

Writing non-stop, with minimal distractions, for 10+ days in a row proved to be an insane experience.

Going into that stint, my manuscript was approximately 49,000 words. According to Microsoft Word, I wrote 48,735 words in ~12 days, or 4,061.25 words per day, generating a ~60,000 word manuscript. I effectively wrote as much in those 12 days as I had in the prior five months.

And I was finally happy with it. So I turned in the manuscript. (I then revised it 4 more times that fall, to create the version that you can read today, but no need to take you through another three months of my writing journey. Suffice to say: this version is the one you want to read)

And when I flew back home to see my family for a few days after my hotel stay, I weighed myself in the guest bathroom and noticed that I’d lost 15 pounds. Which was fine, I probably needed to cut a few pounds before the beach.

Anyway, I say all of that to say you have no idea how stoked I am that it’s finally PUBLICATION DAY, and I want you to buy your copy of Young Money right now:

Buy your copy of Young Money!

So, yeah, Young Money is live. There are about 61,000 of you on my mailing list, and my hope is that each of you buys a copy (or 2, or 3) so you can opine on the brainchild of my hotel fever dream.

Why should you read Young Money?

Young Money is a book on opportunity costs. Specifically, the opportunity costs that you experience in those transitional years between “youth” and “adulthood.” If you, like younger me, have found yourself second-guessing how you’re spending your time, running in loops overthinking “money,” “career paths,” “status,” and the ever-quickly-depreciation of your youth, this is for you.

In the last chapter of his memoir, Norm Macdonald warned us that “The only thing an old man can tell a young man is that it goes fast, real fast, and if you’re not careful it’s too late. Of course, the young man will never understand this truth.”

Norm is right, but since this book is coming out while I’m in the last year of my 20s, my hope is that young people will listen to me.

Your twenties should be an incredibly fun, exciting, adventure-filled decade of life. But they’re also filled with stress. Anxiety. Uncertainty. You have no money or skills, the guardrails of higher education are gone, and you are, for the first time, wholly responsible for the outcomes of “your life.”

You’re supposed to be planting the seeds that you want to compound for decades with a romantic partner and career. But memories compound, too, and what about the memories that you only have a few short years to create before the opportunity disappears? Fun nights out with friends? Taking an impromptu job opportunity across the world? Starting a business on a whim? Learning a new language, or taking up a new sport? With time comes complexity. Responsibility. Commitment. Risk.

It’s easy to get so preoccupied with chasing a particular thing, or, worse, reeling in indecisiveness worrying about chasing the wrong particular thing, that your youth goes by before you blink, and so many of the things that you wanted to do once you had a bit more money, stability, or certainty, are no longer available or enjoyable.

Anxiety and uncertainty are the biggest obstacles facing young folks today, and it’s my hope that this book can help a few of them navigate this highly-fun-but-equally-uncertain phase of life.

(Of course, this book isn’t just for the younger folks in the room. While many of the stories in Young Money are reflections from my 20s, opportunity costs and the “stage-specificity of life” tend to be rather timeless topics).

So, anyway, if you’ve followed along for a while, or if you’re new here but you liked this piece, I think you’ll like this book, and I’d love nothing more than if you ordered your copy here:

Buy your copy of Young Money!

- Jack

And make sure you leave an Amazon review :)

Order your copy of Young Money!

In late September 2021, I fell asleep in the back row of a FlixBus in Sevilla, Spain, and woke up four hours later in Lagos, Portugal.

Sitting above a cliff just outside the mouth of the Mediterranean, Lagos could be mistaken for a Greek island town with its whitewashed limestone buildings, scents of fresh scallops and crabs wafting through the air, and congregation of drunken British twenty-somethings swarming the area in their hopeless attempts to tan their pale complexions in the Iberian sun.

Being the budget-conscious twenty-four-year-old that I was, I had booked five nights at the Rising Cock hostel for a total of $100.

A classy establishment, the Rising Cock’s amenities included fresh sheets and towels every three days, Wi- Fi that worked 85 percent of the time, and a fifty-year-old Portuguese woman named “Mama” who brewed lemon-tea hangover cures and cooked homemade crepes each morning.

Although hostel amenities can be lackluster, hostel culture is second to none. When you’re staying at a hostel, it doesn’t matter what you, or your parents, do for a living. It doesn’t matter if you’re a trust-fund nepo baby with a nine-figure net worth or a broke university student from Madrid who scraped together enough money for two train tickets and ten nights in a bunk bed. At the Rising Cock, you are just another twentysomething traveler living out of a backpack who wants to party with his new friends.

A few of my favorite characters from the Rising Cock:

• My roommates Elliot and Chris: two late-twenties British playboys who loved to rave, surf, and participate in any other activities that didn’t require them to wear shirts.

• James: a twenty-eight-year-old Australian who, after getting stuck in France during the pandemic, decided that spending $5,000 to fly back to Australia wasn’t worth it and opted for a new life in Europe. (His girlfriend, who still lived in Melbourne, proceeded to dump him. He proceeded to indulge in exactly the type of lifestyle you’d expect from a hot, single, twenty-eight-year-old Australian nomad.)

• Mike, a twenty-four-year-old Canadian working remotely from Lisbon, with whom I would, four months later, travel to Argentina for three months.

• Anna, a smokeshow of a Norwegian girl whose high volume of travel-centric Instagram posts in the months following Lagos gave me serious doubts about her claim that she was in “law school.”

But no one made a stronger impression on me than another American, named Simon.

On Friday evening, after donning my go-to bar-fit for this trip (sneakers, sweatshirt, jeans), I headed to the Irish pub nearby for stop one of God-knows-how-many stops on our hostel’s bar crawl around town. This bar matched every other “Irish pub” in tourist hot spots. It was a dimly lit establishment with sticky wooden floors and posters of Liverpool FC plastered across the walls. The bartender, who could have been anywhere from twenty-two to thirty-seven, was sporting a man bun, a couple of ear piercings, and a Hawaiian shirt unbuttoned to his navel. He was preoccupied with giving free shots to girls who could have been anywhere from seventeen to twenty-seven. And, of course, “Mr. Brightside” by the Killers was blasting through the speakers.

While hunched over the bar trying (unsuccessfully) to make eye contact with the ambiguously aged bartender, who was far more interested in an ambiguously aged Dutch girl, I started chatting with Simon. Every travel/hostel conversation starts off the same:

“Where are you from?”

“How long are you in town?”

“We should go kayaking/explore a museum/other ____ thing tomorrow.”

“What’s your WhatsApp?”

“Oh, sorry, I forgot that you’re American too. Thank God; let’s use iMessage.”

I told Simon that I was twenty-four, from Atlanta, and planning to travel for roughly a year before moving to New York for business school. Simon was in his early thirties, living in Chicago, and taking a few months off between jobs to see the world.

I finally caught the bartender’s attention and ordered two Guinnesses, and Simon and I grabbed a table in the back of the bar. Then we ordered two more Guinnesses. Then two more, at which point we reached my favorite part of the night: a heart-to-heart conversation with a stranger I’d just met two hours ago.

There’s this implicit, shared trust between individuals who willingly book a five-night stay in bunk beds in a Portuguese beach town when both parties are aware that you have, at most, a week to hang out before you go your separate ways, never to see each other again.

As a result, the typical multi-month friendship-development cycle that exists in the real world is condensed into a three-day sprint where, within seventy-two hours of meeting a stranger, you learn some of their life’s most intimate details. There’s something cathartic about sharing your life’s regrets, tales of heartbreak, and worries about the future with another American who wanted to get drunk in southern Portugal at the end of the summer.

Between drinks three and four, Simon asked what I was doing in Lagos, and I explained how a few months earlier, I came to the realization that I was wasting my twenties answering Zoom calls and editing Excel and PowerPoint documents from my living room. I wanted to spend a year traveling and seeing as much of the world as possible while I was young.

Simon nodded his head knowingly while I shared my story, and as he finished Guinness number four, I reversed the question:

“So what are you doing in Lagos?”

His answer stuck with me for months.

“When I graduated from college, I was worried about one thing and one thing only: making money. I didn’t grow up rich, and for the last ten years, the only thing in my life that really mattered was financial stability. I figured that once I had saved enough money, I could take my foot off the gas and live a little.

Well, guess what? I made the money, I took my foot off the gas, and now I’m spending a few months traveling before I start my next thing. But all I can think is where did the last ten years go?

It feels like I missed an opportunity to live a little. This hostel thing is fun, but man, it would have been more fun five years ago. It feels like I missed the window to make the most out of spontaneous stuff like this. And I wanted some of my friends to travel with me, but my friends don’t have the flexibility to ‘live a little.’ They’re married, they have kids, they can’t take a spontaneous trip. And that’s fine. I get it. I just wish I’d done this trip sooner. It’s still fun, it’s really fun, but I would have enjoyed this so much more a few years earlier.”

The conversation soon reverted back to more pressing topics, such as “Have you said ‘hey’ to the Norwegian girl from our hostel?,” but the next morning, I couldn’t stop thinking about Simon’s story. Simon had described the stage-specificity of life, and his regrets confirmed my decision to make the leap and take the trip now, before the opportunity slipped away.

To read the full chapter (and book!), order your copy below:

Order your copy of Young Money!

When you’re young, you have several advantages over your older counterparts: You are the hottest you’ll ever be, you have a kick-ass metabolism, you don’t yet have real responsibilities like a mortgage or your child’s tuition, you still view life as an adventure full of unknown possibilities, living frugally isn’t seen as a sign of failure, you can travel cheaply, and your required cash flow is the price of rent for your room in a three-bedroom, one-bathroom apartment with two of your best friends.

But the biggest advantage the young person has is optionality.

Thanks to a low burn rate and lack of real responsibilities, you have the freedom to live anywhere, do anything, and change where you’re living and what you’re doing on a whim. Your one disadvantage, however, is your lack of money. When you are optionality rich and cash poor, the idea of trading that optionality for money is quite seductive.

I have a few friends who are, or who used to be, investment bankers in New York. Why does one become a banker? Because it’s one of few predictable occupations that will pay a young person a guaranteed $200,000+ income in their twenties.

Investment banking is, obviously, a popular career choice for MBA students, but one of the more interesting things I noticed during business school was that my classmates who joined investment banks out of undergrad would commit seppuku before ever returning to a bank.

As a naive kid from the South who had never heard of “investment banking” until he got into business school, I asked my buddy Antonio, who had spent his first two years out of undergrad as a banking analyst at Goldman Sachs, why he was so dismissive of the job. His answer was bleak:

“I remember, probably eighteen months into my job, we were going on two weeks straight of late-nighters in the office. Like, staying until at least two a.m. each night for client demands. We had this VP on our team, a German guy. He was probably thirty, and he had been at Goldman for eight years at that point. It was, I don’t know, one thirty in the morning. The rest of the analysts and I were revising our model for the tenth time when we heard something across the room shatter as our VP screamed, ‘What’s the point! I’ve been here for eight years! What’s the point?’ “And then, the next morning, all of us, including the VP, were all back in the office at ten a.m. as if nothing had happened.

This guy spent a decade with Goldman, and there he was, at thirty, still in the office with all of us at one thirty in the morning. After that, I knew that I was going to bounce after I hit my two years. No amount of money could convince me to live like that.”

How does one end up in such a position that at thirty, they find themselves screaming in an office filled with startled twenty-three-year-olds? By selling eight years of your life for a check.

The Goldman banker likely told himself that he was simply postponing his other desires for a “few years” for the sake of a steady income, implying that after a lucrative bonus or four, he would have enough money to “buy back” the years he lost to the firm. But sacrificing time for money is a Faustian bargain, especially during one’s youth. Sure, perhaps it could work. Perhaps you could, with meticulous budgeting, spend a few years in a high-pay/higher stress job and come out on the other side with hundreds of thousands of dollars in the bank and a bit of optionality.

But what if you aren’t meticulous about your budgeting? What if your apartment costs $4,000 a month, oh, and your post-tax bonus isn’t quite as grandiose as you thought it would be? And, well, if you wait two more years, your pay will jump another 60 percent, so maybe it’s worth sticking around a bit longer?

You wanted to leave the bank at twenty-five, but then twenty-five turns into twenty-six, and twenty-six turns into twenty-seven. What you don’t realize, with each passing year, is that the opportunity to act on the desires of your youth is coming closer and closer to expiration.

- Jack

This blog is an excerpt from my first book: Young Money: A Field Guide to Wealth and Purpose in Your Twenties. I wrote 270 pages on status games, opportunity costs, and the stage-specificity of life; topics that I think are particularly timely today. To read the rest of the chapter (and the full book!), order your copy below:

Order your copy of Young Money!

Order your copy of Young Money!

If you were fortunate enough to be born into a middle-class or higher family in a first-world, western country in the last ~40 years, you are subject to a set of circumstances that would have been unfamiliar to anyone, save a few members of the aristocracy, born before the 20th century: a stable life with financial security is not only attainable, it’s likely.

This isn’t hyperbole: per this 2023 Brookings study, 51% of the lowest socioeconomic quintile of American 9th graders in 2009 were enrolled in college within 18 months after graduation, and 68% of all 2009 high school freshmen attended college after graduation.

Attending college and (assuming you graduate) gaining access to the post-college job market are now table stakes, especially for those who grew up with some means. Of course, the economy is cyclical, you can never fully escape the risk of bad luck, and there’s plenty of room to mess up along the way, but in 2024, with the unemployment rate still near all-time lows, it doesn’t take a Herculean effort for the median American to graduate from college and land a white collar job.

And, as those of us who have spent any time in corporate America know, many of these white collar jobs are excruciatingly simple. To quote myself from a few years ago:

If pandemic-induced remote work showed me anything, it showed me how little "work" was necessary to do my job. I legitimately "worked" 5-10 hours per week at times, but I was always pretending to "work", by either moving my mouse to look active or tinkering with files, models, and decks that didn't really need tinkering to pass the time.

It was pretty obvious that if I didn't show up for a day, week, or month, the show would go on. I was playing with an unplugged remote.

“On Meaningless Careers”

The reality of corporate America is that if you follow the rules, do what you’re supposed to do, and maintain pleasant relationships with your coworkers, inertia takes over, and you can make a living wage while coasting through your career by answering a few emails, updating a few spreadsheets, and making the occasional presentation.

But this ability to coast is dangerous.

While our ancestors risked starving or freezing to death, the risks we face today are psychological, not physiological. In a world where survival is all-but-guaranteed, your greatest risk is that you spend your life not really doing a whole lot of anything.

In January 2022, 24-year-old Jack Raines wrote an essay called “The Opportunity Cost of Everything,” which was, among other things, a wakeup call that life is short, and you need to be intentional with your time. I’d like to revisit a quote from that piece:

We don't waste time by making the wrong decisions. We waste time by falling victim to routine and not making any decisions. We see this happen two ways:

• Apathy

• Hustle

The Cost of Apathy

Tell me if this sounds familiar:

Wake up at 7:30. Roll out of bed, log on your computer at 8:00. Sit around in your sweatpants, make some coffee. Work for thirty minutes, then mindlessly scroll through social media. Maybe you eat some leftovers for lunch. Maybe you pick something up. Back to the computer til five. Then you hit the gym. Come home and shower. Watch football/The Bachelor/Game of Thrones/whatever. Then you make dinner and go to sleep, because it was a long day!

And then you do that over and over and over and over again.

That was my life for a year or so. It has been many of your lives too. And it's easy to fall into this trap of passive routine. You're doing your job, after all. You're doing what you are supposed to do. So you continue to coast on autopilot. Day after day. How many of those dots can you color in with weeks like that? 20? 50? 100? There's no telling.

That's the danger of an apathetic life, life will pass you by before you realize it.

Imagine getting $10,000 every Sunday, but you can't bring any of the money with you to the next week. Surely you wouldn't waste it, right? You would spend every last cent on whatever you want.

Yet we get 10,080 minutes every week. How do you spend those?

The Cost of Hustle

You had a 4.0 in college and landed a great job out of school. You got accepted to a top MBA program. Your goal is to follow the American Dream: Resume filler job that pays well in your early 20s, top MBA, consulting/IB for two years in your mid-late 20s, pivot to private equity around 30, make as much money as possible. The road map to success.

The roadmap to success is like a weird game of Corporate Candy Land.

I was on the road map to success for a while. The problem was that I never asked myself if I liked playing this game in the first place.

I mean yeah, I would have a made a lot of money playing this game. Hell, I probably could have won the game. But was this a game worth winning?

Here's how this game would have gone: Post-MBA, I would have made a ton of money working 90 hours a week for an investment bank/consulting firm. It's not like I would have any time to actually spend that money. But if I did the tedious tasks long enough, I would get promoted to a position where I would work slightly less hours, doing slightly less tedious stuff, and make more money.

Sure, I probably still wouldn't enjoy the work. But I never cared about enjoyment, fulfillment, or any other irrelevant metric, because those weren't the objectives of the game.

Money. Power. Prestige.

Those were the objectives. I just wanted to win the game. Opportunity cost be damned.

Yeah, I might be miserable. But at least I'd be rich. And people would know it.

Hustle and apathy are two sides of the same coin.

You are either too disinterested to pursue what you want out of life, or too vain to realize you are pursuing short-lived things.

And the opportunity cost of both? Your life.

The thing about life is that you don't get a do over. You don't get to go back. You don't get to reach the mountain top, realize that you can't hold on to those fleeting feelings of success, and try to reset your life. Because those dots in your calendar can't be erased.

“The Opportunity Cost of Everything”

I still believe this passage is directionally true, but, looking back, I drew a false equivalence between apathy and hustle. Both have their issues, of course, but the former is far more damaging than the latter.

I would characterize hustle as “misguided ambition,” and the risk with hustle is that your priorities might be determined by external influences, leading you to pursue career paths and life choices that you would not have otherwise pursued on your own. Apathy, however, is far worse than misguided ambition. Apathy is a complete lack of ambition that results in you not pursuing anything at all.

They say that necessity is the mother of invention, but the luxuries of modern life have cured us of necessity, rendering the invention of oneself (through improvement, exploration, and/or the pursuit of a higher self) unnecessary. No longer needing to struggle to survive, many of us relax, defaulting to the apathetic life.

We all know what this apathetic life looks like:

You take an “email job” out of college and spend the next few years getting pretty good at moving around numbers in spreadsheets and logos on PowerPoints. You spend something like 30% of the work day working, and 70% of it zoned out, available to work, of course, while the day passes you by. Your Slack icon is active, though you likely aren’t.

You do this for a few years, then, assuming you hit a few KPIs, you get promoted, and you manage a few folks doing the same tasks you just graduated from. Maybe you switch jobs after five years, where you’ll move slightly different numbers around on slightly different spreadsheets, but nothing really changes. Life becomes a spectator sport where you trade time spent idling on autopilot for a decent paycheck, because your current situation is “good enough.”

The following tweet sums up this entire phenomenon:

“Good enough” might be the optimal strategy for your 401k, where you want to set your money in the S&P 500 and forget about it, but your life isn’t an index fund, and the purpose of life isn’t to optimize for some minimum viable income that pays you enough to cover your mortgage as you sleepwalk to your grave.

The point of life is to live, and living isn’t a spectator sport.

Living means taking risks, pursuing your interests, embarrassing yourself, attempting difficult things, setting ambitious goals, trying, failing, and trying again. Living means pushing your mind and body to their limits, just to see what you’re capable of. Living means fighting back against the inertial forces that draw all of us toward the apathetic life. Living means being the protagonist of your own story, not a passenger whose outcomes are at the mercy of their environment.

The irony of modern life is that those of us with the means to really, truly live, who can afford to take risks and strike out on our own and blaze our own paths, are the least likely to do it, because we are seduced by the comforts of the apathetic life, and we don’t have to go above and beyond to make ends meet. So we continue existing, not living, and the clock keeps ticking.

The most dangerous aspect of the apathetic lifestyle is that you don’t notice the time you’re wasting while you spend your days scrolling TikTok or Instagram, firing off the occasional email while absorbing whatever slop the algorithm pushes to your timeline. It’s only 10, 20, and 30 years later, when the time is gone, that you think, “Shit, maybe I should have done more with my life."

So, what, on the other hand, does the intentional life look like?

The apathetic life expresses itself as maintenance of some status quo, where an individual does precisely what is needed to maintain inertia’s trajectory, and nothing more.

The intentional life expresses itself through actions that change one’s default trajectory, leading to outcomes that would have otherwise been unattainable.

The most obvious expression of an intentional life is one’s career. While luck plays some role in the magnitude of our outcomes, there are no “accidental” successes. Some industries, such as medicine, law, aerospace engineering, and hedge funds require outsized effort just to get one’s foot in the door, and, in any field, ascension beyond the middle ranks is reserved for individuals who differentiate themselves.

That being said, professional outcomes are far from the only signals of intentional lives. As Naval Ravikant once said, “The only real test of intelligence is if you get what you want out of life.” “What you want” is subjective.

If “what you want” isn’t correlated with a particular career path, then a low stakes job with high flexibility could play a critical role in helping you achieve that. I remember, for example, meeting a few digital nomads in Budapest in 2021 who took full advantage of the lax return-to-office requirements at their California-based tech jobs by living abroad and traveling across central Europe. Sure, they may have temporarily sacrificed some degree of career advancement opportunities, but they certainly made the most of it. (Have you been to Budapest? It’s an incredible city, really.)

Making that same career sacrifice to doom-scroll TikTok from your living room for hours because you don’t like the office, however, is not great! If you’re optimizing for ambitious career outcomes, awesome. Do the work needed to make it happen. If you optimize for flexibility, excellent. Take advantage of that flexibility by doing something, anything, with your time. Maybe you have non-work interests that you want to pursue, like learning a foreign language, writing a book, volunteering at animal shelters, or building a niche artisanal clothing brand. Maybe you want to work on an independent business venture, and a low-stress job subsidizes your ability to work on the side hustle in your free time. That works too!

What I’m saying is that you should be intentional with your life and have a little ambition about something, otherwise you’re just wasting your own time. Wasting anyone else’s time is incredibly disrespectful, why would you tolerate doing that to yourself?

- Jack

This blog post helped inspire my first book: Young Money: A Field Guide to Wealth and Purpose in Your Twenties, which goes live in two weeks. If you enjoyed this piece, do me a favor and pre-order your copy here:

Order your copy of Young Money!

Pre-order Young Money, the book!

Writing a book is a funny thing because you spend an exorbitant amount of cranking away on this thing, and then, like anything else in life, imposter syndrome kicks in as you ask yourself, “Is this thing I poured years of my life into good enough to share with the world?” After all, it’s tough to be objective about something you’ve read and reread so many times that you start to see sideways.

However! I’ve now had several friends read early drafts of the book, and their feedback has been validating (see the picture below). So, as we’re now three weeks out from my August 4th publishing date, I am asking, no, imploring, you to pre-order a copy of Young Money: A Field Guide to Wealth and Purpose in Your Twenties for yourself, your son going back to college, your daughter starting her new job in the big city, your cousin who feels “stuck” in life, or all four.

Also, it’s pretty kick-ass seeing your book in hard cover for the first time.

And adding one more review from good friend, recent reader, and target demographic Kiera Klinsky for good measure:

“Huge fan of it, really. Well written, well paced, and informative, optimistic and interesting to read. Very much agree with all you said, especially on pursuing intentionality and combining the things you’re good at!”

A huge thank you to Morgan, Emily, Luke, and Kiera for volunteering your time to read through ~270 pages of Jack Raines brain blasts (and for the kind words that followed).

Now, a few thoughts on who should read Young Money, and why they should read it.

This is not a book that will tell you what to do with your life, but it is a book that will challenge you be more thoughtful about where and how you’re spending your time, particularly in early adulthood. Everything in life is a matter of opportunity costs, and the most expensive decision is indecision: failing to choose any particular thing, and just passively accepting life’s inertia.

The problem, especially for the young person, is that it’s difficult to measure just how expensive those opportunity costs are before a window of opportunity closes.

Do I work on Wall Street? Capitol Hill? What about teaching English in Ecuador? Should I marry my college girlfriend? Break up with a long-distance boyfriend? Move to a new city on a whim? Is it “too late” to make a career pivot? What matters now? What’s going to matter later? What does it feel like as you experience a shift in your life’s window of opportunities? Am I wasting my time?

Young Money is less-so a “here’s how you should live your life” book, and more of a “here’s how, and why, to figure out how to make the most of your time” book. If you’ve ever asked yourself any of the questions in the previous paragraph, then this book is probably for you.

And if this book is probably for you, then I’d love nothing more than for you to pre-order your copy here. Also, a few brief notes on pre-orders:

• Why do pre-orders matter?

  • I would like to hit the New York Times Best Sellers list, and a while the full formula for hitting such list is a bit of a mystery, a successful pre-order campaign contributes meaningfully.

  • Pre-orders inform bookstores of how many orders they should stock for initial runs of new launches.

  • I think I wrote something helpful and valuable, therefore, yes, I want the maximum possible number of people to read it.

• What formats are pre-orders available in?

  • Hardcover, e-book, and audio (I recorded the reading three weeks ago!)

  • Softcovers typically don’t hit print for a few months, dependent on initial sales in the other formats.

• Why should you pre-order?

  • See points 1-3 under “Why do pre-orders matter?”

Thanks for reading and see you in your inbox again soon,

- Jack

My first book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is coming out on August 4th. I wrote 270 pages on status games, opportunity costs, and the stage-specificity of life; topics that I think are particularly timely today. Pre-orders are crucial to a book’s success, and I would be super grateful if you snag your copy by pre-ordering below:

Pre-order Young Money, the book!

Order your copy of Young Money!

I have a few friends who grew up wealthy in New York and Connecticut. Their parents work in finance, primarily. Many of these friends attended private schools that cost upwards of $60,000 per year. By the time they are 18, $700,000 has been invested in their education from kindergarten through high school.

Cool.

What are they supposed to do with their lives?

For a kid born into, say, the lower middle class from Wichita, Kansas, anything he does is upside. Graduating from college, any college, is an achievement. He could join the police force, teach college economics, start an aluminum processing business, write television scripts in Los Angeles, practice law, or manage hotels and be totally satisfied with his career. He could marry anyone and, as long as they loved and respected him, be totally content in his relationship.

The range of possible outcomes in which this individual ends up “successful” is wider than he can imagine.

But if you were born into immense wealth? Sure, you don’t really have to worry about money, but that money comes with a cost. From the day you can walk, the scope of acceptable paths for your life is narrow.

If you don’t attend Stanford, Princeton, Harvard, or Yale, no one will say, “Congrats!” They’ll wonder why you settled for Penn State. Oh, and just because you don’t need money doesn’t mean you’re allowed to now choose a profession that doesn’t pay well. Quite the contrary. It’s expected that you, and all of your high school classmates, land killer high-paying jobs to keep the gravy train going.

The fear of status regression keeps you up at night: making less money than your parents, or doing worse than your 0.01% peers, would make you a pariah. Or at least you tell yourself that. No one has more to lose than the kid born into status. And that pressure to keep up with other high-status peers is debilitating.

Palo Alto is one of the wealthiest cities in America. In 2008-2009 and 2014-2015, two Palo Alto high schools had a suicide rate that was four times higher than the rest of the nation. Why? Because their students were drowning in status anxiety.

Kids in these schools are expected to make straight As, ace the ACT, compete in the biology Olympiad, play the trombone, and dominate California water polo competitions. Just to keep up with their peers. It’s an unsustainable lifestyle.

The rich kid can’t take a risk in his life because, unlike most young people, he was born with something to lose. So, what does he do for work? Something both lucrative and safe to maintain the status he is used to. He works his ass off to take the right steps and go to the right schools, ensuring that he’ll be able to slide right into Kirkland & Ellis, Google, McKinsey, or Goldman. The same jobs that his less fortunate counterparts are chasing in their desperate attempt to gain status.

That’s the irony of status. The reward for winning the status game is another status game.

In his best-selling book Finite and Infinite Games, author James Carse defines finite games as “those played for the purpose of winning” and infinite games as “those played for the purpose of continuing to play.”

Chasing status is a quintessential finite game. No one wants status for status’ sake; it’s a comparison metric. You want more than your peers.

But the acquisition of status begets the desire for more status. Because satisfaction derived from obtaining status is so fleeting, the status chaser’s life is reduced to a series of pursuits in which the value of any given pursuit is dependent on the acquisition of your status.

- Jack

This blog is an excerpt from Chapter 15: The Cost of Status, from my first book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties.

Order your copy of Young Money!

Order your copy of Young Money!

A few years ago, I wrote “25% Loaded” as a series of reflections on my 25th birthday. Today, 2.5 months after my 29th birthday, I would like to return to this theme with “29% Loaded.”

While I share Tim Urban’s disdain for what Buzzfeed (rest in pieces) and its ilk did to the “listicle,” I do still think a tasteful listicle is an efficient and enjoyable format for a “reflections” blog post, so here are 29 beliefs I have now. Some are total reversals from 2022-era Jack, some have only grown more calcified. Feel free to let me know what you love or hate in my inbox or the comment section.

1. The utility of money depreciates exponentially with age.

One of my favorite metrics is “fun per dollar spent.” When I was 21, I could have the time of my life on $20 and change at karaoke night at my favorite college dive bar: “The Hummingbird.” (Largely thanks to $2 beers, $5 cocktails, and a shared appetite for sophomoric nonsense with my college friends). At 29, the equivalent “fun” on a night out is probably something like $200, adjusted for inflation. NYC is more expensive, I don’t want to go to spend my evenings at a dump surrounded by 21-year-old college students, etc. This, of course, applies to more than just “nights out.” I need a nicer apartment for the same level of “life satisfaction” as I had at 23. I’ll probably never stay in a hostel again. The one exception: Citibikes are the best form of transportation, AND they’re 10x cheaper than Ubers. Transit deflation is a W.

2. Adulthood “happens” to you faster than expected.

When you’re 22 on the verge of graduating from college, “30” seems like some distant, far-away place. It also sounds like an age at which you’ll be “washed.” Then you blink, and you’re 29, and half of your friends are 30+, and several of those friends, particularly from the south, are married and/or having kids, and you think, “huh, I guess we became adults.” There’s no specific moment in which any one thing changes. It just kind of… happens.

3. Divergent outcomes become increasingly-common around ~28.

I now have several friends who have, in no particular order, made millions of dollars thanks to joining OpenAI or Anthropic early, had a child with a woman they weren’t married to (whoops!), spiraled into credit card debt and/or are developing gambling addictions, maintained otherwise “normal” careers but feel like they’re falling behind when they compare themselves to the right-tail winners from their social circles, panic-applied to law school or business school, sold businesses for millions of dollars, and failed to sell businesses for millions of dollars. Everyone is on the same “path” through around age 24, but the divergences really begin to materialize as you approach 30.

4. The biggest crisis of the back half of the 2020s is information overload and attention decay.

My screen time last week was 7 hours and 52 minutes. This number is probably a bit inflated; I usually have my phone unlocked next to my computer during the work day, so I’m not “doomscrolling” for 1/3 of the day, but I probably am spending 4+ hours glancing at my phone, and it wouldn’t surprise me if my numbers are “median” for a white-collar worker. Ever-increasingly-powerful social media algorithms with profit motives + a proliferation of AI-slop content has created a potent environment where our attention jumps from “thing to thing” without us dedicating enough time or focus to fully understand any particular thing. The creates an interesting world where everyone is “informed” but no one “knows” anything.

5. Optionality is a depreciating asset.

By 29, you start seeing which folks are “stacking” wins. This is particularly evident in folks’ careers and relationships. One particularly interesting phenomenon in the NYC dating scene: a lot of folks are jaded, treating courtship a chore rather than a source of enjoyment or an intentional pursuit (sense of “choredome” is usually a defense mechanism, but I digress). Similarly, a lot of folks have developed a “job-hopping” psyche of sorts, going from “thing to thing” every two years. Meanwhile, the folks who seem the happiest on the relationship front committed to someone and are trending toward marriage (if not already married), and those with the most “success” in their careers made a bet a few years ago that has compounded, rewarding them with either higher salaries or appreciating equity. Of course, to do either requires taking some sort of “risk”. More on this in a moment.

6. Never pursuing optionality is a recipe for a mid-life crisis.

A caveat on the last point: the folks who I’ve seen spiral the hardest are those who committed to the “wrong thing” way too early. A couple of examples: guy who went to law school immediately out of undergrad, reached 5th year associate level in big law, and is now panicking that he hates the line of work he spent the last 8 years honing. How do you pivot out of the only thing you’ve ever done? It’s hard! Inertia is a powerful drug. Another example: I know more than a few folks who ended 5+ year relationships that started in college around 28 or 29. This is, of course, net “good” in that they at least didn’t marry someone they obviously weren’t psyched to marry, but they also pivot from a half-decade or longer of repetitive monogamy into the post-college dating thunder dome which can be quite unforgiving (or, for some, addicting) to its new entrants. Probably better to try a few different things when you’re young; the stakes are never going to be lower.

7. Geography is a ridiculously-important factor to well-being.

Having now lived in Atlanta for ~2.5 years, abroad for ~1 year, San Francisco for ~1 year, and New York for ~3 years, I can confidently say I’ve never been happier than I am right now, in large part because of where I’m living right now (NYC). There are a confluence of factors at play, including the fact that a lot of my close friends also live here, but geography is such an underrated aspect of wellbeing, and I think a lot of people discount that to their detriment when considering “upward” career moves. The price tag for a decline in “happiness” should be very, very high.

8. Perceived risk is usually an exaggeration of realized risk.

Entrepreneurs tend to understand “risk” far better than career “white collar” workers. The latter struggle to fathom how the former can take a bet without any “guaranteed” salary progression or financial outcome, which is, of course, ironic, given that working anywhere is an implied bet on that company and/or industry’s prospects in the medium-to-long-term. Most of what we call “risk” is really “uncertainty,” given that the worst-case-scenario, if plotted out logically, usually just isn’t that bad. Particularly when you’re young. The happiest folks in their late 20s to early 30s figured this out early.

9. Prestige is a valuable means to an end but a hollow end itself.

The most braindead take on social media in 2026 is that “Ivy League schools no longer matter.” Prestige is the most AI-proof asset in the world, and it’s only growing more valuable. When so many appearances, from product demos to writing samples to resumes and cover letters, can be faked, “proof of prestige” serves as a filter that most folks, from potential employers to potential suitors, will default to. Stacking a few prestige stamps, whether they be good schools, good company logos, or a combination of both, is only going to get more valuable.

But don’t let “prestige” be the end itself, leverage it to do something cooler than gunning for VP at a megacap PE shop.

10. The dating market inverts in your late 20s.

This one is a bit comical to experience in real-time, but the dating market for a late-20s dude in a large city who somewhat has their shit together is just infinitely better than it is for his 5-years-younger self.

(That’s not to say 24-year-old dudes should buy into some nonsense like “I just need to grind for 5 years before taking dating seriously. Then you’ll just be a maladjusted weirdo who doesn’t understand why no one likes them despite their money).

You have more self-confidence, you’re (hopefully) no longer a kid getting status-mogged by dudes five years your senior, you can actually afford to take a girl out for dinner and couple of drinks without worrying about missing rent, and your “market,” age-wise, is basically early 20s to early 30s. 23-year-old guys are fighting an uphill battle against everyone else their age and guys five years older; it’s admittedly nicer being the guy 5 years older.

11. Relatedly: has there always been a wave of terminated engagements in one’s late 20s?

Maybe I’m just ignorant and this always happens when you’re 28 or 29, but I know several girls who have called off their engagements in the last 12 months. It’s not surprising to me that girls are the ones calling off their engagements rather than guys (maybe you half-heartedly said “yes” at the moment, and it wasn’t until months later than reality set in and you weren’t excited), but has this always been a thing?

12. Optimization culture is a total self-own; turn off the devices.

There’s a quote, typically (falsely) attributed to Peter Drucker, that says, “What gets measured gets managed,” which really describes everything wrong with optimization culture today. Imagine if I was, for example, going to grab a few beers with my friends on Saturday afternoon, but my Whoop said that my sleep score was a 42 last night and, oh no, I haven’t hit 10,000 steps today, and, well, how many carbs are in those beers any way? So I instead decided to skip out on any and all social events to reset my health scores?

Optimization for the sake of optimization is a stupid pursuit. You’re going to die at some point; don’t be so pretentious about biomarkers.

13. Writing a book is particularly unique individual struggle (but I’ll probably do it again)

My primary professional goal, since starting this blog in 2021, was to publish a book before turning 30. I’m going to clear that mark by eight months (pre-order your copy here.). From 2021 through ~2024, I romanticized the hell out of “writing a book” for a few reasons: a book has more object permanence than “blogs” or other forms of content, “author” commands more respect than “writer,” and it’s just the aspirational outcome for anyone who decides to share their thoughts online.

What I didn’t realize, until I started working on said book, was 1) just how lonely the book writing process is, and 2) how much of it is really a battle with oneself. “Writing a book” is really “writing at least three books” given the number of rewrites and revisions you’ll do as you inevitably hate the earlier products.

All that being said, I’ll probably do it again in a few years.

14. Someone stupider than you is going to make a lot of money.

People get rich in all sorts of ways, and it’s impossible to fully separate the role that “luck” and “skill” play said riches. I’m going to define “rich” here as someone who’s made $5m or more by the age of 30. A few examples from folks I know:

• Successfully exited a startup where they pocketed $20m+.

• Successfully exited a startup where they pocketed $100m+.

• Joined Anthropic in 2023.

• Joined OpenAI in 2023.

• Joined another high-flying startup that has since 10x’d.

• Joined a new hedge fund that crushed it on the AI trade.

• Bought a shit-ton of Palantir a few years ago (still haven’t sold).

• Gamestop in 2020/2021 (sold the top).

• Married rich.

• Parlayed a few cryptocurrencies.

• Nvidia stock.

• “AI implementation consulting”.

• Ran “rapid Covid testing” shops during the pandemic.

A lot of these people are really smart. All of them, knowingly or not, took on a heightened level of risk in some aspect of their lives. It’s quite easy to look at someone who came into a massive windfall and think, “Why not me?” but you’ll drive yourself insane. Judgement via hindsight is a dangerous game; if you knew the outcomes beforehand, then, yes, obviously you would have made the same decision as them. But we’re all making decisions to the best of our abilities with the information we have at the time. The only real takeaway is outsized returns are downstream of concentrated bets.

15. Envy is the ugliest human trait.

Related to the last point: “envy” is increasingly common as more folks around you are crowned “winners” in some facet of life, and envy is the most corrosive of human traits if it’s allowed to fester. Envy serves no purpose in closing the gap between you and the target of your envy, it just makes its host resentful. A good litmus test is asking yourself to think about the last three people in your broader social circle who had an outsized win. Where you genuinely happy for them, or did part of you begin comparing yourself to their new standing? Comparison is the thief of joy, and it snowballs into envy rather quickly.

16. Watching someone materially destroy their life is a sobering experience.

When you’re young, you have a long leash for “do-overs.” The stakes of doing anything at, say, 18, short of killing someone, are pretty low. You can bounce back from early screwups and have an underdog story. After 25, the world is less forgiving. A collection of stories that I’ve witnessed over the last few years from folks that I was, at one point or another, quite close to:

• Football coach who had an affair and blew up his marriage.

• Serial cheater who blew up a friendship and his own relationship trying to sleep with a friend’s ex.

• Substance abuser who ran a red light while inebriated and killed a woman.

• Suicide after years of drug addiction.

• As well as more than a few folks who have “given” up and are unrecognizable from their early 20s due to apathy and/or weight gain.

While there’s no single way to “win” life, there are a few different ways to “lose.” This game isn’t a spectator sport.

17. Intuition is underrated.

One problem with the “AI-ification” of everything is that, because we have an abundance of data as well as the ability to quickly gather and process said data, it’s easy to default to “the data” when making decisions. One version of this is health-maxxing to the point that you become a slave to your Whoop’s sleep score, another is failing to “trust your gut” when it comes to careers and relationships.

If it feels like you’re on a plateauing (or sinking!) ship, particularly when you’re young, it’s your responsibility, and yours alone, to take care of yourself and redirect your path. If you wait until the “correct” move is obvious, you’ll be late. If you’re going to panic, panic early. I had this experience in my last job working in a media business before joining Slow. Six months in, both the organization and broader industry didn’t “feel” right to me; it was an intuition thing. I made my mind up and immediately started looking for something else. Current job was a much cleaner fit.

Relationships are the most glaring example of intuition oversight: if your gut says “this isn’t it” 12 months in, you’re not going to “think yourself back into it” a year later. Cut your losses and move on. It’s way too easy to sleepwalk through your 20s.

18. Related: careers are always, and will always be, a “people” game.

Money is important, but “ability to earn money” matters way more than money itself early in your career. The best way to hone that ability, (and actually enjoy the process) is working for and with folks whom you find aspirational. A good litmus test is whether or not you would want to “be your boss” in 5-10 years. If that picture is more apprehensive than aspirational, then get out. Life is too short to linger around the uninspired.

19. Sports are the last remaining universal culture phenomena.

The combination of the Knicks winning the NBA championship and the US hosting the World Cup has been a great reminder that, while the internet has become increasingly siloed, sports remain the last bastion of universal culture.

Everyone and their mother was watching Game 5 of the NBA finals two weeks ago, and the footage of Norwegian and Scottish fans drinking New England bars dry has been nothing short of awe-inspiring.

20. Hangovers at 29 suck but I still think they’re largely mental.

Paul Skallas made an interesting observation a year ago regarding hangovers and stress:

“A few years ago, I noticed that when I was drinking alcohol on vacation. I wouldn’t wake with a hangover. Sure I would be dehydrated or mildly fatigued. But I never had pounding headaches or had to lay in bed the entire day. But that’s what usually happened when I drank alcohol at home, on weekdays or on the weekends. I’d get a headache. So I thought to myself, I think it’s probably stress related to hangovers. Working all day at a stressful job and drinking causes some reaction in my body that doesn’t exist when I’m separated from work and in a completely new environment.”

I’m not going to contest the idea that hangovers do typically get worse with age as your tolerance for alcohol, as well as your body’s ability to “bounce back,” declines. But I do think that increasingly bad hangovers have as much, if not more, to do with the increased stress typical to coming into adulthood than the aging process itself. Put differently, I never felt hungover in the Hamptons last summer a few weeks after finally turning in my book manuscript, but a few beers a month before that had me spiraling.

21. If you think you have anxiety, you might just drink too much coffee.

I had never suffered from real “anxiety” in my life up until last fall, but around August I was consistently restless and having trouble sleeping, and my mind was racing 24/7. My first thought was, “Do I need a therapist?” My second thought was, “How much caffeine am I consuming each day?” It turns out that, yes, caffeine is indeed a drug, and when I was ripping at least 2-3 “coffee chats” with founders each day in San Francisco, and ordering a caffeinated beverage at each, I was flooding my system with stimulants. Cutting back on coffee consumption was a low-hanging life hack.

22. Everyone wants the “risk-less” return.

Going back to my earlier points on “envy” and the increasing gap between right-tail winners and everyone else as you get older, an idea that I increasingly believe is that everyone wants the outlier returns but few are willing to tolerate the multi-year period of uncertainty that inevitably precedes said returns. The opportunity cost of “thing that could work,” particularly when it means a pay cut or status hit, is unbearable. Keep that in mind when you see people opting to do something different: it takes balls. I’ll always root for folks willing to tell inertia to kick rocks.

23. New York City is still the peak of human existence.

My highest conviction belief is that every young person should spend at least two years in New York City before they have kids. Should you stay here forever, maybe not? But it’s really the most high-energy city in America, if not the world (particularly right now). Given that America does run the world, you’re doing yourself a disservice by not spending some time in the heart of the action.

24. Tech sales is career arbitrage because it feels “low status.”

Most folks, especially the “coastal elite or wanna-be coastal elite striver folks,” that I know quickly select into one of a few career paths: finance (investment banking, PE, hedge funds), big tech, startups, law, or consulting. And even within the big tech and startups crowd, everyone wants to do some form of “business development,” “strategy,” or “product management” because they sound sexy. But if you’re fairly sociable and willing to grind for a few years, you can absolutely print money as an account executive in a fast-growing company. “Sales” is a slur for status chasers, making it a great arbitrage career for folks who would rather make money than say they work in “finance.”

25. “Travel” as a source of enjoyment has declined with age and the explosion of “content.”

Backpacking Europe and Latin America when I was 24 is, by far, the thing I’m “most glad I did when I was younger but would hate to do now that I’m older.” Part of this is just a natural consequence of growing older, but there’s been a very real shift in the nature of travel tourism as TikTok and Instagram have become more ubiquitous.

Three trends that have diminished travel’s luster since the pandemic: international travel is now broadly accessible, the entire population of the world is on TikTok and Instagram for hours each day, and “hot spots” in different countries now trend 24/7 on these platforms. Everyone wants to visit the same places not for the sake of enjoying the place, but the clout that comes with having traveled to the place, while content creators will do whatever it takes to win the ‘attention game’ while abroad, to the detriment of everyone in their immediate vicinity (blocking sidewalks for street interviews, ring cameras and microphones everywhere, performative posing 24/7.)

The world is increasingly just a stage for the internet. Zuckerberg was right about the Metaverse, he just got the form factor wrong. Life is performed for online perception, and travel has been a casualty.

26. The bottom 10% dictates society.

Elon Musk has caught a lot of flack for being a trillionaire lately, but I personally have few issues with the “wealth gap” between the uber-wealthy and normal folks. Countless folks now have generational wealth thanks to Tesla and SpaceX’s stock prices, and those stock prices went up because those workers gave us kick ass cars and Wifi on planes that actually works. If you make valuable stuff, reap the rewards.

I posted the below tweet a bit tongue-in-cheek, but I’m a firm believer that the bottom decile of society reduces the median citizen’s quality of life exponentially more than whatever acts of “exploitation” billionaires have subjected me to.

Most rules, norms, and laws that inconvenience or hinder your day-to-day life are consequences of the actions of the bottom 10% (or even bottom 1%), not the top 1%.

1% of the population is responsible for 63% of all violent crime convictions. A few shoplifting incidents are the reason I have to ring a buzzer at CVS to get toothpaste. This applies to all sorts of anti-social behavior, from violence on the subway to open-air drug usage in downtown San Francisco. Too much ink is spilled on redistributing the wealth of the winners; not enough on containing the damage of the losers.

27. Wit is the most enjoyable trait in new acquaintances.

One of my favorite things about living in New York is that, approximately every three months, I get a text saying, “Hey, my friend __ __ is moving to NYC; y’all should hang.” at which point I immediately make plans to hang. This hang session, beyond me extending a warm welcome to the best city on earth, is also an impromptu interview of sorts where I, and my counterparty, are silently evaluating if this is someone I actually want to hang with.

Dudes with a natural propensity to riff back and forth without hesitation have had a 100% hit rate of being outstanding additions to my social group. Same applies to first dates. This isn’t a particularly novel take, but I do think people felt the need to disguise their wit during “peak woke” a few years back. I’m glad to see humor on an upswing again.

28. “AI writing” is disrespectful to one’s reader.

No elaboration needed: if you didn’t take the time to write it, and you expect me to read it, consider seppuku? Seriously, publishing AI slop as your own “work” is a middle finger to your reader. Don’t do that. The world needs less content, not more.

29. Rumination is a mind-killer.

A16z founder Marc Andreessen went viral a few months back for claiming that he has “as little as possible” introspection, claiming that it’s both a waste of time and a distraction from progress. While I respect a hot take, I would like to make an adjustment. Occasional introspection is, I think, both valuable and necessary, otherwise how you do even know what “you” are, or what “you” want? The issue is that introspective people are prone to slip from introspection to rumination, psychoanalyzing every nth detail of a career decision, re-reading old text messages 100 times, or playing out hypothetical scenarios in their mind on repeat for days on end, all while telling themselves they’re “being thoughtful.”

Introspection affirms who you are, rumination disrupts the present with thoughts of an unchangeable past or an unknowable future. The line between the two is thin and, at the margin, I think that minimizing introspection is far healthier (or, at a minimum, likely leads to far more life satisfaction) than spiraling into regular bouts of rumination. But it’s hard to shield yourself from your own mind. So maybe there is some truth to ditching introspection. After all, it’s only the introspective thinker who would take issue with avoiding introspection. Drop the introspection and suddenly you can say, “So what?” and move on with your life.

- Jack

My first book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is available everywhere you buy books. I wrote 270 pages on status games, opportunity costs, and the stage-specificity of life; topics that I think are particularly timely today. To catch my next blog post, subscribe to my email list here. For my most detailed thoughts on this topic, order my book below:

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“What’s the right publishing cadence?”

It’s a question I’ve been struggling with for the last few months since wrapping up book edits. Since 2021, I’ve published something like a million words online. A few years ago, I was publishing 2-3x per week. Then it slipped to 1x per week, then I briefly stopped entirely while I was writing my book. And my impulse, both in the “ramping up to book launch” period and, just in general, now that I’m done “writing” a book, was to get back to weekly (or more).

That impulse wasn’t misguided. Book aside (I obviously need to be promoting the hell out of my book, buy yours here), I’ve long held the belief that having a structured cadence of publishing weekly (or insert-your-cadence) is an important part of building audience trust. That line of thinking stemmed from two concerns:

*”Won’t my open rate suffer if I’m not maintaining a reliable publishing cadence?”

“It’s my obligation to have good content in your inbox every Monday.”

I now think this belief is misguided and should be discarded by 99% of folks “creating content” online.

(The exception, of course, is if you truly “write for a living,” meaning you run a media brand that you monetize through subscriptions or brand deals. If that thing is paying you money, it’s your job. And if it’s your job, then treat it as such and hit your cadence.)

Why is this misguided? Let’s look at a dating analogy. For my guys in the audience (which would be most of you), have you ever gone on a couple of dates with a chick, then you find yourself texting her too much? Extending conversations unnecessarily past their natural endings? Forcing the conversation? Every dude has been there. Myself included. It’s a critical character development arc that every young man must endure: you want to talk to the girl, so you find yourself manufacturing increasingly desperate replies to her decreasing-in-length and increasing-in-response-time texts, until she either stop responding entirely, or hits you with the HR text. Then you overanalyze each character of each of those texts like schizophrenic John Nash. (And now you can really overanalyze those texts with ChatGPT. “No, you didn’t ‘bore’ her, she simply wasn’t ready to meet you where you are!” But seriously, please don’t upload your texts to ChatGPT)

There’s no better way to bore your audience than subjecting them to unnecessary content. Want to actually keep someone’s attention? Shut up until you have something to say. There’s an inverse correlation between the volume of messages sent and the attraction you foment from your intended target.

This isn’t dating advice (though it is), it’s also content advice: if you don’t have anything useful, insightful, entertaining, or particularly novel to see, then don’t say anything. The broader “content creator industrial complex” would have you believe that you need to be posting an ever-increasing amount of content. I’ll take the opposite side of that bet. Again, this is assuming that you aren’t trying to be a full-time content creator (God bless your soul if you are; live by the brand deals, die by the brand deals), and you’re just posting for the love of the game.

Your audience will appreciate you for respecting their time by only publishing that which you deem valuable enough for their consumption. If you spare them your afterthoughts and only treat them to your best hits, they’ll read everything you write.

Here’s a few folks I read everything from:

Oliver Burkeman. Morgan Housel. Derek Sivers. Tim Urban.

Oliver Burkeman has hit my inbox six times in the last six months.
Derek Sivers has hit my inbox three times in the last six months.
Morgan Housel has hit my inbox two times in the last six months.
Tim Urban has hit my inbox two times in the last year.

These guys are all prolific writers. Burkeman’s 4,000 Weeks, Housel’s The Psychology of Money, and Sivers’ How to Live are some of my favorite non-fiction books, and I’ve saved more blog posts from Tim Urban than any writer on the internet. Seriously, Urban’s “10 Types of 30-Year-Old Single Guys,” which was hilarious to read when I was 18, is even more hilarious to read now that I’m 29 surrounded by my ever-growing cadre of Peter Pan acolytes.

But yeah, these guys are prolific. And they don’t publish all-that much. I don’t think that’s a coincidence.

And yet, on the flip side, I’ve seen an increasing number of “writers” (a phrase which I use loosely here) go down the opposite path, churning out newsletter after newsletter each week (or quicker!), and almost all of these newsletters smell like the same type of slop. Quick hit “life advice” snippets. Lazily-aggregated links of best tweets or surface level analysis of “the current thing” in financial markets or technology.

Of course, most of these newsletters are either written by outsourced teams or artificial intelligence, because real writing (and, for the sake of this argument, high-quality curating) is both difficult and time intensive. The above-mentioned New York Times best-selling authors can hardly churn out one blog post per month at best, and now we have a crop of “neo-creators” churning out weekly brain rot in my inbox and on my timelines for the sake of “building a brand” or selling another ad slot.

After reflecting a bit on my own reading habits, I realized that there’s virtually 0 newsletters that I read daily, and few, if any, that I read weekly. I just don’t have time. Usually, on the weekends, I’ll skim subject lines for interesting topics from names I trust and catch up on the most interesting pieces from the last few days. I don’t have time to read through the barrage of content hitting my inbox now, and my bet is that you don’t either.

Here’s a novel take: the internet needs less content, not more. I’d rather read a few blog posts a year from someone that leaves me thinking, “This person knows how to LIVE, man,” than endure the forced regular cadence of life advice slop or personal finance hacks written by someone’s team of ghost writers or a Opus 4.8 for the sake of “maintaining their content calendar.”

Yeah, sure, you can sell a few more AG1 ads, but you’re selling your credibility in the process. Your three sentence riffs hitting my inbox or populating my timeline aren’t helping anyone, you’re part of the problem! And my response will be a swift “unsubscribe”.

Again, there are exceptions, particularly on the curation side. Emily Sundberg has built a nice business off of highlighting the stories that actually matter on a daily basis, Ritholtz Wealth Management’s Tadas Viskanta’s daily business and markets roundup is usually full of gems, and Matt Levine and Byrne Hobart are just total machines putting out near-daily quality long-form content.

But there’s a whole crop of “content” which is so obviously just being produced for the sake of “publishing content.” Like, people wake up and think, “Damn, I need to hit publish on some ‘content’,” and then they hit your timeline, or worse, inbox, with some absolute slop. This was already a problem pre-AI, but since LLMs hit the scene everyone is now leveraging Claude to clean up their prose.

Anyone who uses AI to “write” under their name, and then expects someone else to read it, deserves to be lobotomized, but that’s a discussion for another day.

Of course, I know how people fall in this trap. Content used to be easy. There was less competition for eyeballs. Ad slots, particularly in newsletters, sold at a premium. Now there’s too much content, so the natural reaction to someone who feels their relative share of attention is slipping is to accelerate their velocity of content, which, of course, only exacerbates the problem. Humans have finite attention spans with an increasingly-infinite number of distractions vying for that attention. Churning out slop posts won’t help you win the attention game, it just ensures that you’ll quickly get tuned out. Kind of like triple-texting the chick after she says “hahahah”.

So back to my original question: What’s the right “cadence?”

The volume with which you can write stuff that you yourself would give a shit about reading. If you find yourself thinking, “I need to think of something to publish tomorrow,” you’re doing it wrong, and your audience will be able to tell.

The truth is that the people who have the most things worth saying, like the authors I mentioned above, hardly have time to say those very things. They’re too busy living. And that’s fine, because the internet needs less content, not more. When they hit “publish,” I know their words will be worth my time, because their history has shown they actually took the time to write something worth reading.

The right way to think about content in 2026, and this will only increase as the slopification of everything just continues, is to write a smaller number of things that really, actually matter, and then share the hell out of the few pieces that actually move the needle.

I was talking to my buddy George Mack about this the other day. Direct quote from George: “I posted ‘loads of shit’ for about 10 years, and I then spent 7 months working on the High Agency piece, and that, I published it almost a year ago, I still get dozens of emails and DMs a day or week, and that blog post gets 10s of thousands of visitors on a weekly basis. It’s performed on a 100x of any posts combined.”

A single blog post outperformed everything else he’d written combined. Power laws rule everything around me, particularly in content.

This is, of course, also advice to myself.

As mentioned several times now, I wrote a book over the last year-and-a-half (buy yours here), and the ideas in that book on status games, opportunity costs, and the stage-specificity of life, are just so much more valuable than most-anything else I could write about right now. Instead of trying to will myself to come up with new content “for the sake of posting,” would it not be a better use of my time (and certainly yours) to focus my efforts on highlighting this one extremely important piece of work, rather than trying to speed run more “content” for the sake of content?

Probably.

Over the next couple of months, I’ll be highlighting some of the ideas from this book, because I think the ideas in this book matter so much more than anything else I could be writing about at the moment, but after the launch, I’m going to focus much less on publishing “cadence,” and more on “quality.”

Good writing takes time, particularly now, when I’m 10x busier than I was a few years ago. Two blogs a week was easy when I was spending my time vagabonding around Europe. It’s a bit harder now when I’m gainfully employed and busier than ever. There’s plenty of other folks out there more than happy to ship some slop to your inbox to sell a few more AG1 ads.

I’ll try my best to wait until I have something entertaining (or, more rarely, useful) for you. Though my book is a good start.

- Jack

My first book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is coming out on August 4th. It’s my culmination of five years of thoughts on status games, opportunity costs, and the stage-specificity of life. If you’re around my age or younger, this book is for you. If you’re around my parents’ age or older, it’s a fantastic “back to school” or “welcome to the real world” gift. Pre-order your copy below:

Pre-order Young Money, the book!

Pre-order Young Money, the book!

When you’re attending a “watch party” for a sporting event, it’s typically a good move to bring your own drinks, particularly when you’re a group of four dudes who vaguely-but-don’t-really know the hosts. Leeching off others’ drinks is a bit uncouth, particularly when you’re blowing up the gender ratio of said event.

Anyway, I attended a watch party for Game 5 of the NBA finals Saturday night on the rooftop of a friend of a sort-of-friend’s place on the corner of Perry Street and 7th Avenue, and, as a good guest should do, I grabbed a few crates of bottled aperol spritzes to contribute to the cause. Not that it was necessary; upon arrival I was greeted by a full bar, 20 pizzas, and, by the time the game started, ~150 of my closest friends. I have no idea if these hosts were hedge fund guys, NYC trust fund kids, or some combination of the two, but they put together a kick ass showing for the final chapter of a kick ass NBA finals that proved to be the first chapter of what has, thus far, been a kick ass summer in New York City.

Maybe I’m feeling a little sentimental, or maybe my brain is still a bit smooth after consuming four bottled aperol spritzes on said rooftop, a 24 oz canned Modelo in Brooklyn, an espresso martini in the speakeasy basement of some Chelsea bar called “Georgie’s,” and a Piña Colada I bought from a Puerto Rican vendor around 12:07 AM while a thousand similarly-inebriated 20-and-30-somethings, all taking advantage of their own prolonged adolescence, sang along to “Empire State of Mind” outside of Little Ruby’s, but God this place really is perfect.

If you spend too much time on social media (in particular, absorbing content with an especially right wing flair), you’ll be exposed to plenty of reasons that New York “sucks.” Here’s a few popular complaints:

I pay more in rent for my studio apartment on West 15th Street than half of my friends back home spend on their mortgages and taxes, Fox News told me that my mayor is a terrorist, the Roosevelt Hotel somehow became an immigrant asylum, and the dating pool of college-educated white folks around my age is just one multi-thousand person psuedo-situationship polycule of flippant hookups and chronic commitment issues.

But the complaints have one glaring omission: this place is the physical manifestation of “fun.”

And as for those prior “complaints?” Make more money, cut off the news (I’d personally love to crush a few beers with Mamdani), the Roosevelt was a beat hotel anyway, and wear protection. All of the “problems” with this place are either minor inconveniences or brain rot.

Back to this watch party.

I knew five people on the guest list before I arrived. I knew 25 after. You have a bunch of folks around my age (give or take ~5 years) who wanted to do three things: socialize, booze, and watch a bunch of dudes throw a ball in a hoop for three hours. And there were thousands of impromptu gatherings just like this (though most probably had poorer views) popping up all over the city. Across the street, three dudes sharing a 3-bedroom (flex) with one bathroom put a projector on their fire escape and streamed the game on the wall of Little Ruby’s, where thousands of strangers posted up on the sidewalk nearby to scream for Jalen Brunson as he euro-stepped across their brick wall display.

Socialize, booze, and watch a bunch of dudes throw a ball in a hoop for three hours. It’s incredible how sports can bring people together.

The unique thing about New York sports, as opposed to any other city, is the sense of pride non-native New Yorkers feel about these sports teams, and, at a deeper level, this city. A lot of folks are proud of where they’re from, but New York is the only place I’ve lived where folks develop a sense of pride in the place they move to. Few folks who move to Atlanta, or Houston, or Denver, or even Los Angeles or San Francisco, are “proud” of those cities. They might like the cities, sure, but they don’t make that city part of their identities.

Why is New York different?

It’s the only place in America that so many people move to because they want to experience the city for the city’s sake. You move to Florida for beaches and low taxes. San Francisco to hit the lottery on whatever industry is ripping in the current boom cycle. LA because you want to be an actor or screenwriter. DC because you’re a sociopath. New York? Because you want “New York.” The “city” itself is the allure. It doesn’t matter if you moved here from Georgia, or Wyoming, or Bogotá, or Buenos Aires. You wanted New York, you got New York, and you’re proud to make “New York” part of your identity.

That shared pride is why the camaraderie among New York transplants is so strong. There’s an immediately understood “game respect game” because you know, without saying a word, that you’re both here for the same reason.

Can a city be “alive”? I don’t know, but on Saturday night, New York City did its best to pass the Turing Test.

Don’t get me wrong, the economics of living in this place make no sense. Spending $4,000+ for a studio apartment, sweltering summers, the occasional sketchball on public transit, and a Matryoshka doll of never-ending status games seems like a bad trade when you could otherwise buy a home anywhere else in the country for a fraction of the income. But who needs 2,500 square feet when you have a Citibike membership, a 4 Charles reservation for 2, and 10 of your best friends just a stone’s throw away?

New York City kicks ass, and this place has never been better.

- Jack

PSA: My first book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties, is coming out on August 4th. It’s my culmination of five years of thoughts on making the most of the opportunity costs of your youth, before the current stage of life passes you by. Pre-order your copy below:

Pre-order Young Money, the book!

Pre-order Young Money, the book!

There was a window, from approximately November 2021 through August 2023, where I believed the only thing I wanted to do, or at least the primary thing that I wanted to do, was “write.” I have since changed my mind on this for a couple of reasons:

• “Writing” for a living without any other activities surrounding said “writing” is a risky economic endeavor.

• It’s incredibly difficult to “write” well without non-writing inputs that serve as inspiration for the words that end up on paper.

The writing thing worked so far as I landed a book deal (pre-order your copy, and I’ve made a ton of valuable connections and relationships downstream of this newsletter, Twitter, etc, but I also realized in my second year of business school that, yes, having a career that pays the bills while still having the flexibility to write would be a far superior set up than simply relying on writing to pay the bills. So now I’m a VC.

My original intention, believe it or not, wasn’t simply a misguided attempt at extended optionality or a stance against “normal careers.” It was actually rooted in sound economics. Three years ago, my newsletter had grown from 500 readers to 10,000 readers to 45,000 readers over the prior two years, and I went from charging nothing, to $1,000, to $2,500 for ads in my newsletter. Extrapolating those numbers, I could see a very plausible case to making over $500,000 a year with a 2x per week newsletter, plus book opportunities, speaking gigs, etc.

Again, not crazy.

Then some shifts happened: advertising rates fell and subscriber growth slowed as previously useful “growth hacks” on Twitter and LinkedIn became less effective. For two years I was simply writing, and then posting about the things I was writing, and the subscriber graph and revenue graph would go up. Those graphs subsidized a lot of fun shenanigans from the ages of 24 to 26. But when they slowed? I started to panic a bit.

“How do I make the numbers go up again?”

I started to further optimize my social media posts for what might more effectively drive new newsletter subscriptions. I had to cut my ad rates, or get creative in how I packaged ads, to keep the revenue coming in, as advertisers wanted better and better performance numbers. I started to second-guess what I was writing about to begin with. “Should I change up the topics?” “Should I stop running ads, and maybe paywall some of the content instead?”

The “get paid to write what you want” game got much, much harder in Q3 2023, and writing, as a result, became much less fun.

I’ve seen a stat floating around a few times now that says the most desired career path for Gen-Z and Gen-Alpha is to be an influencer or full-time content creator. I can tell you, from firsthand experience, that nothing drains the “fun” out of creating content faster than having your rent checks depend on advertisers’ generosity. That’s how you end up in a predicament called “audience capture.”

Something I didn’t realize in 2021 and 2022 was that monetizing social media, at that point, was quite “easy.” Substack was still pretty new. TikTok was still pretty new. Few people had figured out how to “hack” social media at scale, meaning that if your content (or marketing) was good, it just wasn’t that hard to build an audience, and, importantly, audiences still mattered in 2021 and 2022. A lot of this started to change around 2024, and in 2026, the “content” marketplace is cutthroat.

Cutthroat!

Let’s discuss the market participants in the social media economy today, vs. a few years ago:

2026:

• Aspiring “influencers,” which are the legions of folks making lifestyle content and random short-form commentary, primarily on Instagram and TikTok. Oh, and there’s been a convenient uptick on Substack as well since the advent of ChatGPT. Coincidence?

• Full time individual “creators,” who are churning out quality content on a daily or weekly cadence. They likely operate solo or with a small team. Kyla Scanlon is a good example.

• Professional “creators,” who often have full production and content teams editing their clips and running their channels. Think Mark Manson, Jay Shetty, Mel Robbins, etc.

• AI Slop, from Reels of animated fruits having affairs on Instagram to Substack “thought pieces” and Twitter “market insights.”

• Clipping farms.

• “Curated” content, which is almost-always stolen from other sources.

• Media figures, desperately trying to adapt to a social media-first internet that neither cares about paywalls nor has attention spans lasting longer than 5 seconds.

Oh, and your “follower count” doesn’t matter any more, because every platform’s newsfeed is determined by algorithms.

Even four years ago, algorithms just didn’t have the same influence over newsfeeds, far fewer people were serious creators, “clipping” wasn’t a thing, and ChatGPT had not yet launched. There was just way less noise in the newsfeed, making your content, as a random poster, far more visible. But since 2024, there’s been an explosion of content thanks to the following factors:

• serious players putting serious resources behind content creation

• more and more young people viewing “influencer” as an aspirational career path and thus joining the algorithmic hunger games

• AI removing all friction from content creation

• The perceived importance of building a “personal brand” continuing to increase

• Clipping becoming a viable marketing strategy

Humans only have so many hours in the day, and only some subset of those hours can be spent on social media. If the internet is producing 10x more content than it was 4 years ago, and we’re spending the same amount of time online, your content is now 10x less likely to be seen, absent other variables such as improved engagement hacks or higher volume.

The result: “making it” as a content creator (or, at least, a content creator who makes a living strictly from the monetization of content itself) is a total slogfest.

If you’re trying to make it as an indie creator living off brand deals or subscriptions in 2026, you’re putting yourself on a treadmill against well-funded “teams” working behind the scenes for big-name creators, “influencers” who take increasingly extreme actions to capture increasingly-fleeting attention, and a proliferation of AI slop and clipping farms.

How is anyone going to find you, let alone listen to you? Now add the pressure of tying your livelihood to your ability to get eyeballs, and, well, you get the idea.

The worst part of this development is that most content in 2026 just doesn’t matter.

In 2016, TikTok didn’t exist, Twitter was where famous people shared their random 140-character brain blasts, Instagram was home to your friends’ beach photos, Youtube was a recreational wonderland of entertaining and educational videos, and most “bloggers” turned to Medium, or personal blogs hosted on Wordpress. Social media was, basically, a place to keep up with your friends (Instagram), learn something new or laugh at something stupid (YouTube), or break the news (Twitter).

But now?

Every platform is extracting from their audience rather than serving them. What’s the optimal ad load we can hit someone with without them churning? Short-form video has proved to be a digital fentanyl that can keep us scrolling for hours. Stretched truths garner far more attention facts, so those are going to be amplified, because, again, more time on screen = more ad revenue.

And the content creators themselves, in desperate bids to “keep up with the times,” are just as guilty, turning to more and more aggressive strategies for “hooking” a viewer so they too can make a living by monetizing this engagement with ads.

The result: very little content on the internet is “good,” as the entirety of the internet, from platforms to posters, is now optimized for engaging viewers where they are: passively scrolling for hours a day. Quality is sacrificed for the sensationalistic and the absurd, as anything that’s actually quality takes time to create, and the only way to stay top-of-mind is by churning out more and more content as quickly as possible. And we wonder why 99% of the timeline is ephemeral slop.

If you’re reading this, you probably spend 2+ hours per day on social media. Can you remember five Reels or TikToks you’ve watched in the last month? I can’t think of three, though I know I’ve watched hundreds, if not thousands, since May 1st.

I could tell you dozens of books, YouTube videos, and blog posts that I’ve found interesting. Even a few tweets, as I think the written word does have a bit more sticking power than slop videos, but certainly not a short-form video. Slop in, slop out. And yet, all platforms are pushing short-form videos more than ever, because they’re more engaging, as they require 0 cognitive effort from the viewer. As a result, the entirety of social media’s “content economy” is incentivized to generate performative engagement bait with little thought given to the underlying substance, because engagement bait sells ads.

If you’re an aspiring “content creator” today, you have to win this treadmill, churning out new content day after day that everyone “sees” (if you’re lucky), but no one processes.

Now, all of this isn’t to say that social media, or posting, isn’t valuable. Frictionless connection to the entirety of the human population is, of course, ridiculously powerful, but you need to know what you want to get out of that connection. Fighting the uphill content mill battle certainly isn’t it. At best, you’ll produce mediocre brainrot on a daily basis. At worst, no one will see anything you make.

The only way to make content “work,” economically speaking, in 2026, is to either produce a limited number of generational work(s) then log off the site, or become known for “one” thing and proceed to post about it in a million ways. A few examples of this:

The hottest hedge fund in the world right now is the San Francisco-based “Situational Awareness,” run by former OpenAI researcher: 24-year-old Leopold Aschenbrenner. Two years ago, Leopold published a 165-page manifesto on the ramifications of AI technology and how one might profit by investing the AI buildout. Through the first 6 months of 2025, his fund was up 47%, and by August of that year, Leopold was managing $1.5 billion.

Leopold has tweeted three times in the last year. His pinned tweet, which includes screenshots of his manifesto with a link to the full document, has 8,000,000 views and 11,000 likes. That manifesto kickstarted his now multi-billion dollar fund.

Another example: James Clear, the author of Atomic Habits. Go scroll through Clear’s Instagram page, and you’ll see screenshot after screenshot of quotes from his book or curated pieces of wisdom which he also shares in his newsletter. Every single thing he posts points back to the only thing that matters: the book.

One last example: Bryan Johnson, aka the “don’t die” guy. I mean, look, no one has hammered a brand harder than Johnson has hammered the anti-aging/health-maxxing trend. He live-tweeted his experience taking shrooms with his assistant-turned-girlfriend, before live-tweeting from his assistant-turned-girlfriend’s ultrasound appointment for her nether regions. He have live-tweeted the number of erections he has each night as proof of his healthy libido. He hasn’t missed an opportunity to post a witty quip about his sleep score in two years. And his business is crushing it as a result.

Three different ways to get a bag from your content: scarce sharing of something truly novel and rare (Situational Awareness), repeated distribution of a killer idea (Atomic Habits), or scorched earth brand building with economic upside (Bryan Johnson). The “I’m going to monetize my content by posting a lot” game just doesn’t work anymore in 2026, and if you try to play that, you’ll almost certainly fall victim to audience capture.

In the best case scenario, you become an “AI influencer” to chase whichever venture-backed startups’ marketing budgets you can pillage before they go to zero (at the expense of audience trust and respect, of course). At worst, you risk throwing away your real life for engagement in your fake one. One example: this kid “Big John Golfs“ on Instagram.

His content is, objectively, hilarious. He blew up for making videos of himself ripping a bong or chugging several beers before running eight miles, and his antics have only grown more ridiculous as his audience ballooned to 700k+ followers. But now, because his audience was built on degeneracy, the only way to keep the gravy train going is, as you guessed to double and triple down on that degeneracy. Most recently, he gave us a play by play of his bender in Vegas.

Again, incredibly entertaining content, but he’s also speedrunning a spiral to rock bottom for the sake of an internet audience. Which, as a viewer, I appreciate. But it’s probably not great for his longevity.

That’s not to say there’s not room, or a market, for “recreational content creation.” In fact, I don’t think there’s ever been a better time to “make good content.” Just don’t expect to rely on “good content” for your paychecks in a world of short-form slop.

Casey Neistat is my favorite YouTuber; he’s a consummate professional and total craftsman. He also used to post all. the. time. He was a machine. Then the cadence slowed to a few videos a year. Starting a few months ago, he’s been posting 1-2x per week. And the videos are really, really good.

In his last video, he noted that he deleted social media from his phone so he can spend less time scrolling, and more time creating. Specifically, he noted that removing social media was huge for just allowing him to “focus” on the task at hand again. It’s not a coincidence that as soon as he ditched IG and TikTok, his YouTube game exploded. It’s hard to make anything quality when you’re constantly plugged in to the short-form dopamine machine.

Young people aspire to be influencers. Social media prioritizes short-form videos. As a result, countless young folks are trying to “win” the social media game by churning out Reels and TikToks day after day. Making content they don’t particularly want to for audiences that don’t particularly want it, all in an attempt to monetize their “engagement” with brand deals while the platforms themselves make billions by pumping ads after every third video.

I think we all have better things to do than create and consume short-form slop every day until we die. Make good things for the sake of making good things, don’t make slop for the sake of a few clicks. Less TikTok, more Casey Neistat.

- Jack

I appreciate reader feedback, so if you enjoyed today’s piece, let me know with a like or comment at the bottom of this page! And make sure to pre-order my first book, Young Money, by clicking below:

Pre-order Young Money, the book!

Pre-order Young Money, the book!

Today’s letter covers my thoughts on broader investor FOMO into semiconductor and memory stocks, why software might not be dead, and some nuance on how AI could make certain software players even more valuable.

SaasPocalypse: Q1 2026

Claude Code got really good around Thanksgiving of 2025 when Anthropic dropped Opus 4.5. If you used AI coding assistants in June 2025, you probably found them to be “useful but messed up a lot,” requiring way too much handholding to be left alone, lest they destroy your codebase while unsupervised.

That changed with Opus 4.5 (and, soon thereafter, similar updates to OpenAI’s models), and after every developer and their mom played with these coding assistants over the holidays, consensus quickly became, “Software is cooked, Claude Code is GOATed.”

The result: investors began dumping software stocks hand over fist, with the iShares Tech Software ETF down ~37% in Q1 of 2026.

Memory Stocks to the Moon

This selloff was amplified by the fact that, at the same time, everyone began piling money into semiconductor and memory stocks like Intel, SK Hynix, and Micron, as investors who had previously balked at AI thought, “Maybe AI isn’t a bubble, and maybe I’m underexposed.”

The irony is that, despite several of these stocks running up 1000% or more in the last year, they’ve actually gotten “cheaper” on a P/E basis.

Micron’s stock has 10x’d since April 2025, but it’s actually cheaper on a forward earnings basis than it was a year ago as demand for memory thanks to the AI buildout is just insanely high, so memory providers are printing money hand over fist.

Micron’s net income in 2024 was $1.4B. In 2025 it was $9.5B. The company is projecting $68B in profit in 2026, and $112B in profit in 2027. Free cash flow is jumping from $121M in 2024 to $36B in 2026. Memory is historically a low margin, cyclical business, with Micron’s gross margins climbing from 20% in 2016 to 59% in 2018, before collapsing back to 31% in 2020. They were 41% in 2025 and they’re projecting 77% and 79% in 2026 and 2027, respectively. It’s not a “bubble,” the AI bottleneck companies are just making an insane amount of money now.

And, if you are a fund manager, there is a very real “career risk” in missing the AI infrastructure wave. The S&P and Nasdaq are RIPPING given that they’re so overweight semiconductors right now, so if you’re underperforming your benchmark AND you missed the thing powering the indices, you risk having your LPs pull out their capital and allocating elsewhere.

So, now that these stocks have melted up, and may very well be poised to keep melting up, many funds are dumping their other positions to allocate toward semiconductors accordingly. The result? Even more selling of software stocks.

It’s a vicious feedback loop: the AI infrastructure trade maintains momentum, forcing more investors to pile in or risk missing out, leading to more selling behavior is the software sector, adding more fuel to the “software is dead” narrative (as price often drives narrative), causing more people to sell software to buy AI stocks, and... you get the idea.

Combine that with the fact that so much of the market is either index funds, retail investors chasing momentum, or multi-manager hedge funds playing quarterly earnings rather than taking 12-18 month perspectives, and you just don’t have a lot of buyers for software stocks right now.

Where Does Software Go From Here?

To be clear: AI is very much a threat to software. Nontechnical folks can build functional code in minutes. Technical folks can deploy dozens of AI agents to crank through tasks for them simultaneously. Companies are reimagining their internal workflow processes around AI at the same time that newer, leaner, faster startups are competing with their more mature competitors for customers, cutting into incumbents’ pricing power. Some software companies, particularly those that have historically provided “personal productivity tools,” are likely cooked, or, at least, face an uphill battle.

But also, while “software” is a sector, not all software companies are created equal, and we’ve started to see a dispersion in outcomes for different software companies’ stocks. For example, Palo Alto Networks sold off hard in Q1 with the rest of software, until, wait! It turns out that AI opens a whole swarm of security vulnerabilities, which could be quite bullish for a cybersecurity stock.

I think we’ll continue to see a greater and greater bifurcation in software names as the overarching narrative of “AI is going to kill all SaaS” is disproven by specific companies putting up stellar earnings, and, at some point, the market will begin to respect that resilience as proof that maybe AI won’t kill “everything.”

Though, personal productivity tools like Asana are probably cooked.

Another recent example: Figma. I bought some Figma stock a couple of weeks ago largely because the stock’s price action just felt totally detached from reality. As a reminder: Figma is a collaborative design platform that went public last summer, briefly hitting $142 per share in August. Its stock price has since collapsed to ~$17 per share as of May 2026.

Figma was, at its IPO, overvalued. It was briefly worth ~$56 billion post-IPO, or 40x 2026 revenue. Those multiples don’t work any more in 2026.

(Also, an aside, but Figma was one of the best private software companies, and it got smoked in the public markets. There’s plenty of overvalued private companies waiting to get cut in half in the public markets, in my humble opinion).

The stock then collapsed by ~85%, thanks to a combination of “this stock is overpriced,” the broader narrative of “SaaS is cooked,” and Anthropic launching its “Claude Design” tool (which is wonderful; I’ve used it to build some social media templates for my book promotions).

At a $9B market cap and ~7x sales, it wasn’t “cheap,” but if you take the view that 1) this company is growing fast and will continue to do so, 2) is spitting off high margin free cash flow (a rarity for SaaS businesses these days), 3) could very well benefit from the AI boom, and 4) is led by an AI-pilled founder who still very much wants to win, then, well, while the broader narrative still sucks, the stock starts to look interesting.

And, while the “AI will kill software” has some truth to it, I think the more nuanced reality is that AI changes which software is more valuable. At my job, for example, we’ve rearranged some of our internal software tooling, but I’m actually using Notion more now as a dashboard / interface layer for tracking our dealflow and pipeline. We’ve rearranged a lot of the under the hood flows, but Notion as a collaborative dashboard tool has actually become more valuable, not less. My high-level take is that a lot of software companies that serve as coordination layers of multiple parties’ information may benefit from AI, particularly as more and more agents take on larger and larger workloads.

So, I bought some Figma.

Their earnings came out last week, and the results were great:

46% YoY revenue growth (accelerating), 139% net dollar retention (highest in two years), 27% adjusted FCF margins, etc. There’s still some flags (gross margin pressure as AI inference is more expensive than normal software margins, threats from Google / Anthropic, etc), but at least for now, the company is far from “dead,” and the stock ended the day up 13%.

Anyway, I think we’ll see a select group of software names start to prove that “AI just might not kill me,” which, of course, will be ironic as so much money is right now pivoting to the memory names that are up 1000% in the last year.

Happy Monday, let’s have a great week.

- Jack

I appreciate reader feedback, so if you enjoyed today’s piece, let me know with a like or comment at the bottom of this page! And make sure to pre-order my first book, Young Money, by clicking below:

Pre-order Young Money, the book!

Other Notes, Thoughts, Riffs:

• Another shameless plug to follow my new Instagram as I ramp up this book marketing campaign.

• Claude Design is seriously fantastic for creating marketing materials and content. I used it last week to make some templates for book promo stuff on social media, and I’ve been loving it. (see examples below). If you have a Claude account, you should check it out.

Pre-order Young Money, the book!

As someone who has written close to a million words online at this point, I have had, from time to time, people ask me, “Do you think AI will kill writing?”

My answer to that is “no,” but AI has killed something else. The previously timeless phenomenon through which the existence of “text” signaled the intellect, understanding, or ideas of the text’s writer to its audience.

RIP written word as a shortcut for assessing someone else’s thoughts: 3,000 BC - 2025.

An example: Twitter was, originally, a place for short-form, 140 (then 280) character posts. Twitter now has an “article” feature, allowing you to publish native blog posts directly on the timeline. One particular group of folks LOVES Twitter articles: the industry I work in: venture capitalists.

Why?

Well, everyone wants to be a self-described thought leader for some mixture of either branding or flaunting their knowledge to the founders they’re trying to court. Which, again, is fine if it’s your knowledge. Union Square Ventures’ founder and general partner Fred Wilson has been writing a blog for decades; it’s textbook VC lore at this point. I have never once doubted whether or not something that Fred wrote was “Fred.” He’s been doing this for decades. I’m sure Fred Wilson would commit seppuku before publishing AI content, or, at least, masquerading AI-generated content as his own thoughts.

But I swear 90% of articles I see on the timeline are just AI slop masquerading as venture capitalists’ “unique insights.” Give me a break.

It’s not that all AI content is “bad,” but the misrepresentation of LLM output as one’s original thoughts is intellectually dishonest slop.

I define “slop” as something that takes longer to consume than it took its creator to create.

By definition, “slop” could be a web app, blog post, or YouTube video. The nice thing about slop code, however, is that as long as it “works,” meaning it gives me the correct outputs from the inputs that I give it, it doesn’t really matter. Does knowing how to voice-to-text Claude with “dangerously skip permissions” turned on mean I’m a software engineer? Of course not. My slop code is probably crawling with security lapses, and I wouldn’t trust anything I build to be deployed in an enterprise setting. BUT! It’s quite useful for me and my own workflows, and I don’t try to present myself as some genius for knowing how to tell Claude to do stuff. I’m a proud “slop cannon” building random stuff all week, it’s a huge productivity hack. But I’m not tricking anyone into thinking that I, Jack Raines, am the architect of the software I’m building.

I even list “Claude” as a contributor on my Github repos.

“Slop” writing feels especially egregious given that the act of “writing” is synonymous with ‘thinking.” AI did not change this equation: if you can write well, odds are you can think well. What AI did do, however, was allow folks to masquerade as “writers” when they have slyly hidden “Claude,” their co-author, from the audience’s view. Someone is thinking, but it’s a GPU in Virginia, not you, person “publishing” the idea.

Usually, when I’m reading, and especially if I’m reading someone’s blog, I’m not-so-much reading to learn about “a thing” as much I am to learn about what a particular person thinks about “a thing.” Their perspective and understanding is half of the joy of reading. I don’t want to simply know “thing,” I want to know the writer’s take on “thing.”

With AI, you can no longer assume that what you’re about to read is the brainchild of the article’s byline. And that is quite annoying. One benefit of writing online so publicly since at least 2021 is that I learned how to write. Another benefit, however, is that because I was writing in high volumes pre-ChatGPT, a stranger who finds my page can more safely assume that my writing is “human,” not “AI.”

It’s not that anyone who just starting writing in 2026 has to be using AI, but writing is an inherently difficult thing, and if your public writing output coincided with a magic bot that could write for you, well, that’s convenient. Which sucks for new writers, because it’s that much harder to earn audiences’ trust.

I now put “writers” in two camps: “pre-ChatGPT” and “post-ChatGPT.” Anyone who started their blog or grew their platform prior to ~2024 was probably writing their own content. With anyone who just started in 2025, or especially 2026, you just don’t know. And that’s the issue: you can’t assume a new writer’s work is their work if they don’t have older proofs of work with which you’ve grown accustomed to.

But the bigger problem is that, with AI content exploding in volume, your typical reader isn’t going to take the time to evaluate whether a piece of content is “human” or “AI.” They’ll likely skip it altogether, meaning that slop content is crowding out original thoughts in the marketplace of ideas.

Another interesting “writing” shift caused by AI is the increasing value of brevity. AI loves these long, drawn out explanations. I swear the labs have weighted their models to use as many tokens as possible to boost their revenue numbers. Anyway, because AI loves to ramble, brevity is, I think, an increasingly human trait.

10 years ago, some laborious, long-form, ridiculously dense article might have helped prove your gigabrain IQ to whichever readers managed to survive your 12,000 word monolith.

But now? Just put the prompts in the bag, bro.

Combine our already shrinking attention spans with growing distrust of the purity of anything too long or wordy, and we’re entering an age of more Hemingway, less Dickens.

- Jack

I appreciate reader feedback, so if you enjoyed today’s piece, let me know with a like or comment at the bottom of this page! And make sure to pre-order my first book, Young Money, by clicking below:

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Two quick programming notes:

1. I wrote a book, Young Money, and it comes out in August. I will, between now and August, marketing this book aggressively, as I would like to sell as many copies as humanly possible. I also think it’s a very good book, you should therefore pre-order it, and you’ll be glad you did. Pre-order link here.

2. I’m about to start hammering Instagram, because I think it is, at this point, a much stronger distribution mechanism for selling books than Linkedin/Twitter/Substack. Give me a follow here as I try to speedrun this thing to 100k followers.

A bit of Jack Raines career history lore here: In fall 2024, I was pounding the pavement applying to different jobs, looking to pivot out of the media space. (for those of you who aren’t aware, I was, at the time, working for Robinhood, helping build out a media business they were incubating).

The first jobs I looked at, one of which I ended up landing and accepting, were in venture capital. But I was, at the time, casting a pretty wide net, which led to me applying to a job at Anthropic as well. For context, in November 2024, Anthropic wasn’t the household name it is today. While it was valued at $18 billion (a very high number for a “startup!”, OpenAI at that point was worth $157 billion, completely valuation-mogging its competitor.

The job I had applied for was part product manager, part product marketing, part comms and narrative: basically helping to shape how Anthropic products and Claude releases showed up in the world. The salary for this job paid something like $175,000 to $200,000, and the equity compensation, at that point, would have probably landed around ~$125,000 per year, or $500,000 total in illiquid stock.

I did not, as you could probably guess, land that job, but if I had landed that job and stayed there for two years, my equity package would be worth quite a lot. Anthropic recently raised funding at a $380 billion valuation, and the company is talking to investors about raising a new round at ~$900 billion this month. For my math wizards, $900 billion is a 50x markup on the $18 billion valuation when I had applied for the job just 18 months ago. $500,000 in equity x 50 = $25 million. Even accounting for dilution in subsequent funding rounds, it’s safe to say that a $500,000 equity package in fall 2024 is worth $15 million or more today, with ~half of that vested. And what about folks who joined earlier, in 2023? They’re likely sitting on $50 or $100 million in unrealized gains as Anthropic looks poised to IPO by the end of the year.

A question worth considering is “what do those employees do next?”

This is a fun hypothetical for me to consider, given that I had applied for a job that would have, in hindsight, made me ~$10 million in vested equity richer in just two years had I been hired.

There is, of course, a subset of folks who do think that “AGI” is real, they are building the machine to end all machines, and we’re only a few months out from “money” losing any real meaning as intelligence becomes both free and commoditized. Many of these folks joined OpenAI or Deepmind in the 2010s, or Anthropic in 2021 and 2022, and, if they’re still working at their AI labs at this point, they are probably working for something more than money. (I personally disagree with the AGI hypothesis, but I also haven’t made $10 million+ from AI equity.)

But most Anthropic (and OpenAI, xAI, etc.) employees are normal, albeit competitive, folks, who, like me in 2024, probably realized that “AI” was going to be the trend that dominated the next 5-10 years, and working for one of the companies at the forefront of AI would have a high likelihood of making them a lot of money. But no one expected everyone to get so rich so fast.

Most equity compensation packages vest over four years. 25% after one year, then monthly vesting for the next 36 months. A lot of 20-somethings took a relatively-high paying job anticipating some level of equity appreciation, but no one saw an $18 billion “startup” jumping to a ~$1 trillion valuation in two years. This level of insane wealth creation in 24 months for a small group of people is unprecedented. So, if you’re an ambitious 29-year-old who finds himself, post-Anthropic IPO, with $14 million liquid, what do you do next?

This is, of course, something that companies think of ahead of time. Public companies (and later-stage private companies) tend to preemptively offer “refreshers” to their top performers, giving them additional equity grants on top of their initial grant to keep them incentivized to work there.

The issue here is that these AI companies’ valuations have jumped so much, so quickly, that the “additional equity” has diminishing marginal utility for most smart-but-not-totally-AGI-pilled folks. If you’ve made $3-4 million in a few years, you’re probably happy but not-at-all ready to retire or jump ship, and you’ll stick around for another $3-4 million in equity grants. But at $15-$20 million, the math changes. You have retirement-level wealth, and even if you don’t “retire” for good, you could certainly afford to take a break for a year or two, particularly when the upside on new equity grants pales in comparison to the 50x spike you had since 2024.

A tweet went viral yesterday where Citadel founder Ken Griffin explained how he admonished a recent Harvard grad who said he’d quit his job to “travel and climb the highest peaks around the work” if he had $10 million liquid tomorrow.

While it’s a stupid interview tactic to tell the billionaire founder of one of the world’s largest hedge funds that you’d say “adios” if you made $10 million, I do think most folks, if they had that level of wealth creation virtually overnight, would consider something similar.

If you joined an AI startup because you really believed that you were building the machine god, then, well, 1) you probably joined quite early, before the economic outcome was obvious, 2) you’re past the point of “money” mattering as you’ve long since become rich, and 3) you are probably motivated by something more than “money” alone. But if you’re a “normal” opportunistic employee who caught the AI wave early, realized it would be the biggest step function change in tech in your early career, and now you’re up $20 million on that bet, well, you probably couldn’t care less about AGI.

But owning a ski house in Jackson sounds pretty nice.

Market pundits have thrown around plenty of concerns that could kill the momentum of the current AI boom: compute crunches, energy costs, data center construction delays, or public backlash (such as everyone on TikTok actually thinking AI is wasting our water supply).

I think the more interesting risk that isn’t talked about enough is “What if all of the employees get too rich too fast?”

Founders and early believers might be motivated by more than money, but plenty of folks joined these companies for, more than anything else, an opportunity to make an ungodly amount of money. And once you make that money, well, it’s a bit tougher to stay motivated, and additional equity compensation just isn’t that appealing when you can afford anything you could possibly want.

Companies are nothing more than collections of people. If those people get too rich too fast, many will be tempted to ring the register and do something else. I’m not predicting the AI bubble to pop anytime soon, but it will be ironic if the thing that “kills” AGI is too many AI employees getting too rich too fast.

Links and Other Thoughts:

• Good piece from Baillie Gifford’s Tom Slater on the cognitive impacts of extensive AI usage. The piece raises interesting points on how over reliance on AI weakens our knowledge retention and understanding. I’m also 99% sure this was written with AI, given the flow of the prose, but still an interesting piece.

• Situational Awareness Essay: A couple of years ago, former OpenAI researcher Leopold Aschenbrenner wrote a long-but-thoughtful essay on how he saw AI ramping up over the next few years, and he raised a ~$250 million hedge fund to invest in the companies that would benefit accordingly. Situational Awareness has since printed money, now managing a few billion dollars. It’s good to read back over this in 2026 and see how right he was.

• This was a great Invest Like the Best interview with the GOAT Paul Tudor Jones. Here’s a fun related “lessons learned” piece from Tren Griffin about what he learned from PTJ as well.

- Jack

I appreciate reader feedback, so if you enjoyed today’s piece, let me know with a like or comment at the bottom of this page! And while you’re here, pre-order your copy of Young Money, too.

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🚨ATTENTION YOUNG MONEY READERS🚨

As some of you know, I spent the last ~year and a half, give or take, working on a book. Last Friday, I finally read the first physical copy: 272 pages of an “uncorrected proof for limited distribution.” I’m quite proud of this thing. It’s a mix of humor, philosophy, irreverence, and reflection, but, most importantly, it’s the book I wish I could have read when I was 22, and I think the contents of the book will be relatable to all of you.

I’ll give more details on “what” and “why” for this book in a moment, but first, I am stoked to announce that you can pre-order your copy of Young Money right now, available for delivery on August 4, 2026.

Pre-orders are super important as they show bookstores that people are interested in this particular book (thus telling those bookstores to stock up!) so if you’re considering buying Young Money, I’d love for you to pre-order a copy by clicking here:

Pre-order Young Money here!

Why should you read this book?

Young Money is a book on opportunity costs. Specifically, the opportunity costs that you experience in those transitional years between “youth” and “adulthood.” If you, like younger me, have found yourself second-guessing how you’re spending your time, running in loops overthinking “money,” “career paths,” “status,” and the ever-quickly-depreciation of your youth, this is for you.

In the last chapter of his memoir, Norm Macdonald warned us that “The only thing an old man can tell a young man is that it goes fast, real fast, and if you’re not careful it’s too late. Of course, the young man will never understand this truth.”

Norm is right, but since this book is coming out while I’m in the last year of my 20s, my hope is that young people will listen to me.

Your twenties should be an incredibly fun, exciting, adventure-filled decade of life. But they’re also filled with stress. Anxiety. Uncertainty. You have no money or skills, the guardrails of higher education are gone, and you are, for the first time, wholly responsible for the outcomes of “your life.”

You’re supposed to be planting the seeds that you want to compound for decades with a romantic partner and career. But memories compound, too, and what about the memories that you only have a few short years to create before the opportunity disappears? Fun nights out with friends? Taking an impromptu job opportunity across the world? Starting a business on a whim? Learning a new language, or taking up a new sport? With time comes complexity. Responsibility. Commitment. Risk.

It’s easy to get so preoccupied with chasing a particular thing, or, worse, reeling in indecisiveness worrying about chasing the wrong particular thing, that your youth goes by before you blink, and so many of the things that you wanted to do once you had a bit more money, stability, or certainty, are no longer available or enjoyable.

Anxiety and uncertainty are the biggest obstacles facing young folks today, and it’s my hope that this book can help a few of them navigate this highly-fun-but-equally-uncertain phase of life. (Of course, this book isn’t just for the younger folks in the room. While many of the stories in Young Money are reflections from my 20s, opportunity costs and the “stage-specificity of life” tend to be rather timeless topics).

So, anyway, if you’ve followed along for a while, or if you’re new here but you liked this piece, I think you’ll like this book, and I’d love nothing more than if you ordered your copy here:

Pre-order your copy!

A few other points:

• I’m going to, over the next four months, be ramping up the marketing a ton. 1) Please forgive me, and 2) if you know anyone who doesn’t follow me, but you think might benefit from this book, shoot them this blog post, too.

• If you work for a company, university, nonprofit, or other organization that would like to bulk order 25+ copies of Young Money, please add your information here.

• If you, or someone in your network, is a podcaster I should chat with, let me know with a reply to this email or DM on Twitter or Linkedin.

• I’ll be throwing a few different launch events in different cities this summer. Stay tuned.

Thanks for reading along, I hope you enjoy reading Young Money as much as I enjoyed writing it.

- Jack

I appreciate reader feedback, so if you enjoyed today’s piece, let me know with a like or comment at the bottom of this page!

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Now that I am again writing this newsletter on a regular cadence, I’ve asked myself, “What should the current iteration of Young Money look like?” The equilibrium I’ve reached is treating Monday mornings as the time to publish my thoughts on the “current thing(s)” in tech / markets / whatever is dominating my Twitter feed, while publishing non-regular, less timely blog posts as they take root in my brain. To today’s piece.

Yesterday, someone pulled up to Sam Altman’s house in San Francisco and fired a gun at the property. Three days ago, someone threw a molotov cocktail at Sam Altman’s house in San Francisco.

It goes without saying that these are horrible, disgusting attacks against Altman and his family, and the freaks that perpetrated them should be punished by the fullest extent of the law.

These were also not, in my opinion, isolated and/or “random incidents.”

The man who threw a molotov cocktail at Altman’s home is 20-year-old Daniel Alejandro Moreno-Gama. Moreno-Gama was an active member of “PauseAI,” an organization whose name is self-explanatory. In the “PauseAI” Discord chat, he had sent messages including “Is there any sort of timeline for how long humanity has left?” As an 18-year-old college student, he emailed congressman Dan Crenshaw addressing the group’s concerns with AI labs not taking safety and alignment seriously. Last week, he threw a molotov cocktail at the home of OpenAI’s CEO.

Meanwhile, Americans in multiple states are actively protesting, and closing down, data center construction projects. In January, NPR reported that protesters in Virginia, Pennsylvania, and North Carolina have shut down proposals for new data center buildouts. A town in Wisconsin tried to can their mayor for approving a new data center. Maine banned new data center until November 2027, after seeing their total cost of electricity bills spike 60% between 2021 and 2026 (they also, notably, banned nuclear reactor construction, which may have helped with power costs, but I digress). Virginia, the top state for data center construction, booted its GOP governor and elected a democrat who promised to “make data centers pay their own way for power.” It turns out that everyone, especially young people, dislike data centers, and that disdain carries across both sides of the political aisle, per Heatmap News.

Democrats hate data centers because of their environmental impact. Republicans hate them because they represent big tech forcing higher power bills upon Americans. Zoomers hate them because.. vibes?

In Oklahoma, 21-year-old GOP organizer Kennedy Laplante Garza started fighting a nearby data center proposal known as Clydesdale after learning over the summer that it would be built a mile from her family’s farm. “I didn’t even know that much about data centers at that point,” she told me. “But I knew my friends across the state were fighting similar things, whether they were solar panels or wind turbines.”

Will Manidis made a site tracking data center moratoriums in the US by state. Guess what? five states have active bans, ten have legislation advancing, and seventeen are under discussion.

The majority of Americans “hate” AI. Of course, that shouldn’t be a surprise when the CEOs of three of the biggest AI labs in America are all basically saying the entire white collar labor force is just a few years away from getting brutally job-mogged by LLMs:

• May 2024: Elon Musk says AI will take all of our jobs.

• May 2025: Dario Amodei tells Axios that AI could wipe out half of all entry-level white collar jobs and spike unemployment to 10-20% in the next 1-5 years.

• October 2025: Sam Altman says AI could eliminate jobs that ‘aren’t real work,’ implying that many of today’s white collar jobs are, to put it bluntly, “fake.”

• January 2026: Dario Amodei predicted that humans would be unable to adapt to AI development’s rapid pace, and this would trigger an “unusually painful” short-term shock in the labor market.

• January 2026: Elon Musk says that in 10 - 20 years, “work will be optional.”

• March 2026: Sam Altman admits that AI is killing the “labor-capital balance.”

It turns out when you tell people, “Hey, we’re building mega technology, it’s going to take your job, and, by the way, you’re going to help pay for it with a higher power bill,” people get pissed off and/or anxious. Some of those people will act on that anxiety and/or anger by protesting data centers, but, in a population exceeding a minimum size, there will be outlier, left-tail individuals who decide to take matters into their own hands, threatening to destroy infrastructure, or, in the case of Altman, threatening the leaders of AI themselves.

There is a very, very good blog post by Tim Ferriss called 11 Reasons Not to Become Famous that is, I think, relevant when thinking through these attacks.

Think back to your 5th-grade class. In my case, there were 20–30 kids. Was there anyone totally off the rails in your class? For most of you, there’s a decent chance kids seemed pretty sane. It’s a small sample size.

Next, think back to your freshman year in high school. In my case, there were a few hundred kids. Was there anyone volatile or unbalanced? I can think of at least a handful who were prone to violence and made me uneasy. There were fights. Some kids brought knives to school. There was even a kid rumored to enjoy torturing animals. Keep in mind: this high school was in the same town as my elementary school. What changed? The sample size was larger.

Flash forward to my life in July of 2007, less than three months after the publication of my first book.

In that short span of time, my monthly blog audience had exploded from a small group of friends (20–30?) to the current size of Providence, Rhode Island (180,–200,000 people). Well, let’s dig into that. What do we know of Providence? Here’s one snippet from Wikipedia, and bolding is mine:

Compared to the national average, Providence has an average rate of violent crime and a higher rate of property crime per 100,000 inhabitants. In 2010, there were 15 murders, down from 24 in 2009. In 2010, Providence fared better regarding violent crime than most of its peer cities. Springfield, Massachusetts, has approximately 20,000 fewer residents than Providence but reported 15 murders in 2009, the same number of homicides as Providence but a slightly higher rate per capita.

The point is this: you don’t need to do anything wrong to get death threats, rape threats, etc. You just need a big enough audience. Think of yourself as the leader of a tribe or the mayor of a city.

Tim goes on to explain the various death threats, stalker incidents, and psychotic messages he’s had to deal with since his first book blew up. And Tim Ferriss isn’t particularly controversial or mega-famous; he’s a moderately well-known podcaster known for his life optimization and bio-hacking content.

The leaders of the AI labs have millions of Twitter followers, and, in 2026, information spreads across the internet like wildfire, meaning the total “audience” for any message involving any major figure in AI is likely in the billions, or, at minimum, hundreds of millions. And that message, right now, is that AI is about to blow up your way of life and displace most of the white collar labor force.

Say that “audience” in America alone is 100 million people. Even 1% of 1% of that audience is 10,000 potentially unhinged actors off their meds going through some version of psychosis. And you just never know when one of these psychos is going to act on their impulses. Particularly if that psycho is a frustrated young male. Who threatened to blow up an xAI datacenter last spring? A 25-year-old male. Who threw the molotov cocktail at Altman’s home? 20-year-old male. Remember Luigi Mangione? Yeah. Young male.

Young males are, compared to other demographics, prone to violence, disorder, and destruction if their life is otherwise in disarray. And people really, really hate AI. Look at the TikTok comments on posts about Altman’s home being attacked. It’s a mixture of satire, crude irony, support for the attacker, and allusions to Luigi Mangione.

Take nation-wide AI psychosis, disgruntled young males, online communities festering AI resentment behind closed doors, fundamental misunderstandings of what this technology can actually do, and narratives that spread like wildfire, far outpacing whatever the “truth” might be, and you have a pressure cooker for a few insane folks to take a vigilante approach to defending their ideals, no matter how false those ideals might be.

I mean, come on, Luigi Mangione was a mentally unwell 20-something dude who committed a horrific act in killing a married father of two, and he’s still a cult hero amongst internet incels who think Mangione was standing up for something. But this is, in fact, the world we’re living in today. Guess what? Narratives, even if they’re false, can be powerful, and, through that power, dangerous if they frighten the wrong soon-to-be bad actor. “The American health insurance industry is preying on you.” Is that true? Who knows. Someone thought it was, and they murdered a healthcare executive over it in Midtown, Manhattan.

Is AI going to “kill white collar jobs?” No. AI, and, more specifically, LLMs, can do a lot of things well. It’s great at generating code! It absolutely can churn out code, read through documents, and write prose in, basically, no time, and it can scale, theoretically, to infinity. That is very useful. But AI does not have activation energy, agency, desire, or will power. It’s not nuanced, though it can mimic nuance. It doesn’t “know” or “remember” things like humans, though increasingly large context windows allow it to “recall” increasingly impressive amounts of information. But there’s so much subtle friction in, well, most jobs, that I’m just bearish on the idea that AI will, at some point, “do everything.”

But the narrative being pushed by every player in AI is that AI will, in fact, eat the entire world. And there’s nothing anyone can do about it. Is that narrative true? I mean, I’m personally bearish on any concept of “ASI” or “AGI,” but you need a narrative when you’re trying to go public at what will likely be that $1 trillion+ valuation.

The bigger the valuation, the bigger the narrative needed, particularly when you’re still years from profitability, access to compute is increasingly “the only thing that matters,” and the difference between frontier models is marginal at best. And the only narrative that can support what will likely be multiple loss-making trillion-dollar companies in the public markets is that we’re $500 billion in compute spend away from ending “work” as we know it.

I do think Anthropic’s founders actually believe in an AGI and ASI future. I do not know if OpenAI’s executives believe it, or if they are simply aware that they have to sell this vision to keep raising capital. It doesn’t really matter. At the end of the day, all of the talking points basically boil down to, “We’re raising to terminate all of your jobs. Tbd on what comes after that.”

Silicon Valley’s ethos is “accelerate or die.” Most of America just wants to earn their living wage and watch their kid’s baseball game on the weekends. Folks don’t want to be “liberated from white collar work.” They just want to put in their hours, get their check, and do whatever they want in their free time.

The AI narrative of “We’ve built the thing that’s going to eradicate your jobs” is antithetical to the long-standing unspoken agreement between capital and labor in America: “Do your work, and you’ll earn enough money to live a good life.”

Now it’s, “We are replacing your work. Maybe you’ll get UBI or something. Have fun in the permanent underclass.” Again, I am “short” the idea that AI is actually going to take all of our jobs. But if you tell the same story over and over again, do you really think the very people whose jobs and power bills are threatened are just going to sit by and think, “Ah well, I guess I should ride out the next five years, then good luck.”

No. People, unlike LLMs, have agency.

When threatened, or at least when they perceive themselves to be threatened, the far left tail actors will, in fact, act. And each actor emboldens more actors. A protest in one town shuts down a datacenter? More protestors will appear in other towns. The momentum accelerates. Someone throws a molotov cocktail at Altman’s home? Someone else comes by two days later with a gun. Every vigilante spawns a new vigilante, and the vigilantes think they’re the good guys stopping the “evil overlords” of AI.

I’ve seen a lot of takes on Twitter blaming journalists for stoking flames of resentment against Altman and AI industry in general. And, yes, sure, there have been plenty of pieces painting these folks in bad lights, and, yes, sure, some of these pieces were likely in bad faith. But when your talk track for two years has been “AI’s going to eradicate the income stream that supports your family,” I don’t think it’s that crazy that some folks might take that threat seriously, and act on their desperation in desperate ways.

A lot of investors are worried about training costs, long-term margins of increasingly-commoditized frontier models, and access to GPUs in 2029. I’m worried that some asshole from rural Arkansas is going to spend too much time on Reddit and then go blow up a datacenter in Memphis to “save the world.”

Anyway, happy Monday. Let’s churn through some tokens.

Content Recs:

• For my SF folks: I’m co-hosting a tech / VC / startup breakfast with my buddy Morgan Barrett on Tuesday AM. If you’re around, come hang!

• Former US Senator Ben Sasse, a great Twitter follow and also rarity of a good person in Congress, is dying of stage four cancer. But before he dies, he’s also hitting the podcast circuit hard. This conversation with Ross Douthat at the New York Times is a really, really good read / listen.

• Hilarious project that someone made all “NYC lines” that is, literally, monitoring “lines” at popular NYC restaurants. Shout out vibe coding. Here’s the website link: damnlines.com

• Really fun piece in the New York Times by John Carreyrou on finding the creator of Bitcoin.

- Jack

I appreciate reader feedback, so if you enjoyed today’s piece, let me know with a like or comment at the bottom of this page!

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Brief note: I’m co-hosting a San Francisco Tech Breakfast Club next Tuesday from 9-11 AM PDT. If you’re around, come hang, caffeinate, and chow down with friends. Signup link here.

I spent most of 2025 living in San Francisco.

Before December 2024, I had never visited San Francisco. In fact, my only experiences on the west coast before December 2024 were a trip to San Diego with my grandparents for my grandpa’s board meeting when I was 12, a trip to Los Angeles for the Rose Bowl in 2017 with my then-college girlfriend, in which we slept in an RV camper in a tailgate parking lot with her family (they lived in LA, but went all-out for the Rose Bowl every year. This was when UGA pulled off a miracle over the Baker Mayfield-led Oklahoma. Sick game. I think that ex-girlfriend is engaged or married now. I still have my Hinge radius set on four miles of Union Square, Manhattan and filtering for 20-something chicks that are Christian and/or Catholic. Who’s the real winner?), and a wealth management conference called “Future Proof” where I saw Third Eye Blind play live in September 2024.

I had never visited San Francisco.

Then I went out there for a job interview. Self-driving had always “sounded cool” until I flew out there and tried my first Waymo. I’ve never done crack cocaine before, but I imagine the “wow” factor is similar. That thing blew my mind. Car driving itself. Insane. Suddenly, I could connect my Spotify to the surround sound in a fancy Jaguar and jam to whatever I wanted without some stranger with a 4.88 Uber rating who smelled like a mixture of cigarettes and stale pizza judging my music or eavesdropping on my phone calls. I think there are a list of “firsts” that are quite memorable for dudes born in the 90s.

• First touchdown (or goal, homerun, etc).

• First time bench pressing two plates.

• First time sipping alcohol.

• First time having sex.

• First time beating the last mission on Halo 3 on veteran difficulty.

• First time riding in a self-driving car.

On the second point, if you’ve never benched two plates, I think it’s hard to call yourself a dude. Especially now that everyone is ripping peptides. Get your weight up. I digress.

Anyway, the future is now in San Francisco. So I ended up moving out there for a year. Where I’m from, in Georgia, “self-driving” is some mythical future from the Jetsons. Except in Atlanta, where sometimes the Uber you order is a Waymo, and sometimes it’s some stranger who doesn’t match the Uber picture, and their best friend in the front seat with blunt wrappers on the floor, and you wonder “why did I pay $20 for this?" For some reason, Atlanta forces you to order Waymos through Uber rather than just using the Waymo app.

Anyway, self-driving is this insane, futuristic-but-not-realistic thing in most of America. In San Francisco, it is my default form of transportation.

Oh, have you seen the housing market going crazy in the Bay Area? It’s because OpenAI just raised like $120 billion at an $850 billion valuation in preparation of their $1 trillion IPO despite the fact that they’re about to incinerate another $100 billion+ on data centers. Does the business work? Who cares. As long as Masayoshi Son will buy $20 million+ of OpenAI stock from AI researchers (read: folks who figured out how to get “next token prediction” to convince you that, yes, your idea which isn’t great is, actually, quite genius), and Nvidia continues its generational run of printing infinite money by selling their former bitcoin mining rigs to companies who want to generate infinite tokens by forcing their developers to vibe-code 100,000 lines of code per day, it’s going to cost you $5 million for a 3 bed, 2 bath home in Pac Heights.

I set up an old Mac Mini a month ago.

Why? Well, when I got on Twitter in February, I saw that some Austrian / British dude named “Peter” built an AI assistant that you can tell, through Whatsapp, to order pizzas for you. If you’re not careful, someone will prompt inject your OpenClaw and steal your social security number and the nudes your girlfriend sent you, but hey at least it can monitor your email for you. OpenAI “acquired” Peter (but not OpenClaw, which is a nonprofit foundation, similar to how OpenAI was originally, before it became a trillion-dollar, for-profit company. Because who the hell wants to be a non-profit when Masayoshi Son will shove $100 billion down your throat and speedrun WeWork again?) for about as much money as they paid to acquire a niche, but popular, daily tech show: hundreds of millions of dollars.

There’s this meme of “escaping the permanent underclass.”

That meme basically means you have about 18 months left (probably less, now) until AI gets so good that money, and really your entire existence, is rendered totally irrelevant. Which is a hysterical conclusion to draw from a “next token prediction” machine, regardless of how good it is at predicting tokens, but it seems like everyone in San Francisco believes it. Either A) you better get hired by an AI lab, or B) you better raise $100m for your startup and get acquired by an AI lab, by 2027, or… adios! Off to the token mines for you. Go make some human training slop to create marginal improvements for Opus 5.69 or whatever.

Of course, maybe there is some truth to the “permanent underclass.” At least in the engineering world. See, LLMs can’t replace most jobs, in my opinion. Most jobs have some level of nuance or friction, and LLMs are, really, word-and-number prediction machines. They’re quite good at these predictions, but, again, they’re kind of limited to screens. But coding? Well, coding is just a bunch of words and numbers, and it’s easily verifiable. The code either works, or it doesn’t. Give an AI enough context and a big enough context window, and it can build basically “any code.” And San Francisco, which was originally a gold rush city, has made a lot of people who knew how to code rich over the last 30 years. New platform comes out (computers, the internet, mobile), and the folks who could “use code” to build on that platform (Facebook, Airbnb, Uber) made a shitton of money. But now, “code” is commoditized. The biggest value prop in “tech,” being the guy who can build the digital money printing machine, went from a tightly held secret to accessible to anyone with a keyboard and 5th grade reading comprehension.

No wonder everyone in the Bay is so anxious.

Also, shout out to Stack Overflow for selling for $1.8 billion just one year before ChatGPT rendered it redundant. Talk about securing the bag. That feels like a microcosm of what’s happening in tech in general: get your bag before you get rug-pulled. And the timeline for securing that bag keeps shortening.

Anthropic now has a “Mythos” model that found several security holes in the Linux, and helped patch a 27-year-old bug in OpenBSD, an operating system, two years older than me (launched in 1995), known for its security. This thing is so powerful that Anthropic wouldn’t even launch it. They just tweeted about it, and said that 12 companies have access to it, and it’s too dangerous to release publicly right now because everyone and their mom could use Mythos to hack everyone else and everyone else’s moms. That’s pretty good marketing, to be fair. “Hey, we build AI God. It’s super scary. We’re telling you about it, but you can’t use it. Sorry!”

With Mythos, you could, hypothetically, say, “Hey Claude, steal all of _____ internal secrets. LOL what a good prank.” and it could probably do that?

The marginal value of the marginal software engineer is quickly plummeting to zero, and a small group of people and companies with GOATed models are operating on God-mode right now. It’s like a zero-sum race to extract the last amount of money left while money is still a thing.

Anyway, I moved back to New York two months ago. A couple of my buddies asked me, “Have you used Perplexity?” I went on a date with a girl who “worked in consulting,” and you would be shocked, SHOCKED, to learn that not once did she ask me about what harness my OpenClaw runs on. I think most of my friends are using ChatGPT at this point (?), a few know what “Claude” is, no one has touched a terminal, and the word “bash” sounds a bit like what a Neanderthal does with its club. I’d like to see Opus-4.6 split the G, or rip a Citibike across the Williamsburg bridge. I went to a Broadway show a few weeks ago. No AGI in sight.

What’s the point of this ramble?

The disconnect between the epicenter of AI (San Francisco, and. more broadly, a certain subsection of Twitter) and the rest of the world is just wild. The former truly believes we’re on the verge of a world-changing paradigm shift. The latter just doesn’t care. Perception doesn’t just shape reality; it is reality. And, really, I think both can be true. In a world that lives and dies by the power of bits, well, yeah, an automatic bit generator certainly changes everything, doesn’t it?

But in a world that just wants its Uber to arrive on time, (or, even better, a Waymo with no mystery man behind the wheel), which is most of the “real world,” by the way, some super-powered coding assistant is just, like, irrelevant. And that’s what’s funny about this whole AI boom: most people don’t care. And, hysterically, they don’t have to care. I mean, like, yes, they could, hypothetically, get a lot of leverage from all of this stuff. But does it “really” matter? I’m honestly not sure.

Again, I subscribe to the belief that AI can, and will, automate all code. “Coding” just becomes another form of writing. Some people will be prolific, others will suck, but everyone “can” do it. Or soon will be able to. Guess what? The invention of writing was pretty cool. We’re all just used to it now.

I don’t think “AI” will impact most other jobs, occupations, and sectors, nearly as much as “code generation” because there are too many edge cases. So, I guess, I see the world going something like this:

• The speed in which better and better software is released and updated will be astounding.

• 99% of people who have never written a line of code will never write a line of code.

• That 99% of people will benefit, as consumers, from cheaper code (competition drives prices to zero when anyone can generate code for no cost!) by having access to an ever-growing selection of impressive software. They might notice, “Oh wow, my apps don’t glitch as much,” but that’s about it.

• That 99% of people will remain totally unaware of the existential-levels of anxiety happening in the Bay, and they’re probably better off because of it.

On this last point: I feel the angst. I have, somewhat, sipped the “AGI kool-aid.” I panic-forced myself to figure out how to use Claude Code to build different stuff because. I thought it was going to be table stakes to “survive” as technology continues to accelerate. I’ve used Claude and ChatGPT and Grok and Perplexity and Wispr and Parallel and Exa and Manus and… you get the idea. I have a personal AI assistant named “Clank,” that I can talk to through Telegram, who can order pizzas for me or figure out who, in my rolodex, I should grab beers with next week.

And yet, all of my friends who have no idea what the hell a “Command Line Interface” is are making fine money living in their Manhattan shoe boxes, just like me.

There’s a tale of two worlds happening right now: a small subset of people speedrunning “AGI,” and then everyone else, who couldn’t care less. The former might make a lot of money, at least in the short-run. But the latter is probably having more fun.

Ignorance is bliss. Enjoy the permanent underclass, it’s fun down here.

- Jack

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Happy Monday, to those who celebrate. Last week was quite busy on the Slow Ventures front. We hosted an Etiquette School in NYC on Tuesday evening, then an “AI bots training school” for creators in San Francisco on Thursday and Friday. I also turned 29 last week. One more year until I’m officially washed. Okay let’s get into it.

Forward Deployed Hedge Fund Analysts:

An idea I’ve had for a while now is that market cycles move faster, and more violently, than in the past because information disseminates quicker than ever before thanks to X and Reddit. Online narratives around stocks are like crack cocaine for market reflexivity. LLMs have only accelerated that trend.

A good working model of the investing world in the age of AI is that any data that is publicly available will be instantly reflected in market participants’ models. “Crunching the numbers” isn’t edge when AI can both gather all publicly-available data and integrate that data in any and all relevant models instantaneously. Wire your computer to constantly parse EDGAR filings and tap into the X API for real-time coverage of relevant stocks, and AI can now process information far faster than was ever possible for humans.

In a world where AI can both gather and process all publicly available information instantly, the only “real” edges left are 1) access to hidden information and 2) discernment over what information should be discarded. On the second point: when you have unlimited tokens at your disposal, “analysis paralysis” is a greater threat than ever before. You can always look at “another thing,” even though any good investment comes down to 1 or 2 things that really matter. But that’s a topic for a later blog post; for now, I’d like to focus on point 1) hidden information.

In the private markets, hidden information means that you know a hot founder is raising for their new company before that becomes public knowledge. Either you know the founder directly, or a mutual friend makes an introduction, but you are granted “access” to that information before it became public knowledge, therefore positioning you to act on that information before everyone else. This has, of course, always been the way venture capital has worked, particularly at the seed stage. The only difference now is how quickly you can speedrun the “research” part of your diligence (mapping out competitors, understanding the technology itself, etc). Access + discernment are the only games in town.

In the public markets, hidden information is… a bit different. You, obviously, can’t coerce material nonpublic information (MNPI) from executives of public companies. That’s a great way to end up in prison. But you can, however, go find information that could be, but currently is not public. One way to find that information might be sending your analyst on a speedboat to the Strait of Hormuz.

Last week, investment research firm Citrini did just that…

And on Sunday evening, they published a “field trip” recap, both detailing the adventure in Oman (events include, but are not limited to, near arrests, in-person footage of ships on fire, and drones buzzing overhead their dingy) and providing actionable investment takeaways stemming from what their analyst saw in the Strait. (See below for the full piece):

Citrini Research

Strait of Hormuz: A Citrini Field Trip

Introduction…

Read more

5 months ago · 503 likes · 23 comments · Citrini

I mentioned above that analysis paralysis is a real threat to the investment process with AI being able to ingest, well, everything. Combine that with the fact that AI slop is bombarding social channels left and right, and it becomes difficult to know what’s real, and what’s worth ingesting, in the first place. Over the last few weeks, for example, there’s been so much fake footage of bombings in the Middle East (either claiming the wrong location, or, quite literally, just AI-generated slop), that it’s impossible to sift through the noise. One way to know what’s real, then, is to see it first-hand. In an interview with Lex Fridman, Jeff Bezos said, “I have a saying, which is when the data and the anecdotes disagree, the anecdotes are usually right…” In a world with infinite data, anecdotes, such as eyewitness reports from an analyst that you send to Oman, can be quite valuable.

Citrini is a research publication that also trades its own book, and in this case, they did adjust their portfolio positioning based on what their analyst saw in the Strait, from tanker traffic to anecdotes from Omanis and Iranians he met sharing their thoughts on how they believed the conflict would play out.

While I don’t necessarily think every Tiger Cub is going to start sending analysts to Ukraine, I do think that as LLMs continue to commoditize the gathering and modeling of public information, more “journalistic” approaches to investing will drive more and more alpha. IRL investigation is also one of few things that AI won’t, at least for the foreseeable future, be able to disrupt.

OpenAI Buys TBPN:

Three weeks ago, OpenAI claimed that they were going to “cut back on side projects” and focus on nailing their core business; aka coding and enterprise. The reason? Anthropic started kicking their ass as of late, both in revenue growth rate and “vibes.”

In January 2025, OpenAI’s annualized revenue was $6 billion and Anthropic’s was $1 billion. By October 2025, OpenAI’s was $13 billion and Anthropic’s was $7 billion. By March? Anthropic had reached $19 billion in annualized revenue, closing in on OpenAI’s decelerating annualized revenue (~$25 billion in February).

Anthropic has taken a very, very focused approach to AI. For starters, they never released any video or image generation product. From 2023 through early 2025, their only “consumer” product was their chatbot, and they offered API access for their models to enterprise customers. Then, in February 2025, they released “Claude Code,” and it took the internet by storm. Claude Code was the first AI product that, for a lot of people, offered a glimpse into what “autonomous coding” could look like. By typing “claude” into your terminal, you could describe what you wanted in English (or Spanish, Japanese, whatever) to your computer, and it would just… build it. Early on, it made a lot of mistakes, and you had to regularly re-prompt it, but, still, it was magic. And it’s only gotten better. When models experienced a step function improvement in November, Claude Code got really, really good. Like, “spend 15 minutes brainstorming a task, tell it to go “cook,” and let it do its thing” good. By this point, OpenAI had countered with the launch of Codex (its version of Claude Code), but Claude Code had run away with the mindshare by 1) being first and 2) (more importantly) being consistent.

OpenAI, over the last 3.5 years, has launched ChatGPT (which has had its own ridiculous set of model names, from “mini” to “turbo” to “o1-preview” to “01-mini.” Like, seriously, who can keep up with these?), DALL-E (text-to-image), Sora (its now-cancelled text-to-video “social platform”, Codex (coding assistant), Frontier (agent-management platform), Atlas (browser), an unnamed consumer hardware device (they acquired Jony Ive’s startup for billions), custom chips, “adult mode”, and ChatGPT Health.

Anthropic had Claude and Claude Code. It turns out that developers will pay a lot of money to use Claude Code, so they doubled, tripled, and quadrupled down on Claude and Claude Code. Pretty much all of their product releases have just been improvements to these two tools: either integrating Claude into other platforms (Claude for Excel and Claude for Powerpoint) or adding new features to Claude Code (skills, plugins, Claude Cowork). Much easier to get the messaging right and win customer trust when you’re only selling a couple of things.

So it’s not a shocker that a few weeks ago, OpenAI’s “CEO of applications,” Fidji Simo, sent around a memo claiming the company would be cutting back on side projects. Then, two weeks later, they acquired daily tech show TBPN for ‘low hundreds of millions.’ The $100 million question on X last week was, “What did OpenAI actually buy?”

I love TBPN (which was basically Sportscenter for people who know what “reinforcement learning” is). I know John and Jordi fairly well, I’ve been on the show a couple of times myself, and they invented a novel, new media format that was expected to do ~$30 million top-line this year. Good for them for getting their bag; but there’s just no way, (regardless of what a lot of folks on Twitter are saying) that this was a “distribution” purchase.

This deal was likely on par with Joe Rogan’s latest Spotify deal, worth $250 million. Between Youtube and Spotify alone, Joe Rogan averages ~4 million+ views per episode. TBPN averaged something like ~70,000 viewers per episode across platforms. Sam Altman’s Twitter account, with 4.6m followers, has greater “distribution” than TBPN. So a 9-figure acquisition in the midst of a “no more side quests” command from management is.. interesting.

My $0.02? OpenAI’s vibes have been cooked for the last ~six months, they’re trying to push through an IPO by the end of the year while the market is increasingly skeptical of their valuation, and Jordi and John have the best marketing and comms chops in tech right now. Paying ~$200 million, when you were last valued at ~$850 billion (0.024% of your enterprise value) is actually a really low price to pay for a couple of guys who just might fix your brand perception, particularly when AI research talent is routinely getting acqui-hired for billions of dollars. And that’s the right framing to look at this from, by the way: talent acquisition, not “buying distribution” or “the future of media” or whatever.

Altman / OpenAI realize that they need to fix their public image ASAP in this ramp towards an IPO. Jordi and John both understand how to 1) capture the narrative and 2) charm OpenAI’s target market (tech investors, entrepreneurs, and developers). They also almost-certainly realized that, if they were to take a deal from OpenAI, Anthropic, or any other big tech platform, their credibility would be, at least slightly, tainted when they were critiquing AI platforms. Even if they are actually editorially independent, there will be an inherent level of audience skepticism toward their AI takes now that OpenAI owns them. To be “okay” with the opportunity cost of the drop in perceived independence (particularly when they were set to make ~$30m this year), it was going to take a big number, and OpenAI hit their ask.

Sure, paying a “forward revenue multiple” of ~7-10x 2026 revenue for a daily tech show sounds high, but this was never about the business. They’re winding down their ad business post-acquisition; OpenAI couldn’t care less about the ad revenue. This is about hiring the talent that they think could help them “control the narrative.” And $200 million is cheap if it increases your odds of a $1 trillion IPO.

Mercor’s Big Security Lapse:

AI models, like ChatGPT and Claude, train on data. Much of that initial training data was scraped from the internet. Blog posts, Github code bases, Youtube videos, tweets, etc. Most of that publicly available data has now been fully ingested and picked over. But AI labs can further improve their models through practices known as “supervised fine-tuning” and “reinforcement learning.” In the former, humans write high-quality responses to prompts to teach the AI “how to answer,” and in the latter, humans compare two model outputs and select the superior one.

AI labs need a supply of humans to provide these data-training tasks, and Mercor fills that gap. If you go on their website right now, you’ll see “find remote work opportunities.”

Those opportunities involve, essentially, creating workflows that mirror what you do in your job, and selling those workflows to AI labs via Mercor. For your efforts, you’ll earn anywhere from ~$50 to $150 per hour, or ~$500 to ~$1,000 per project. Put differently, you’re being paid to help train AI models to do your job.

(I don’t fall in the full dystopian camp that thinks AI will kill the labor market or whatever, and I think people are quite malleable, but the fact that AI labs are paying willing contractors hundreds of millions of dollars to help them train AI to do their jobs is a bit.. wild).

To land one of these opportunities, you take a recorded “AI interview,” your information is saved, and then you can apply for open positions on their site. Here’s a couple of example job listings for “audio and video technicians” and, hysterically, “basketball experts.”

Through this process of interviewing candidates and collecting their submission data, Mercor collected a massive data set on 10s of thousands of contractors, including personal identification information, videos of workflows, screenshots of their screens, and, obviously, videos of them interviewing and performing these tasks. This is, obviously, valuable training data, given that labs are paying millions of dollars to acquire it.

And last week, 4TB of data, including candidate profiles, PII, employer data, source code, API keys, video interviews, and customer data, ended up in the hands of Lapsus$ group (according to Lapsus$). The brief play-by-play:

• A month ago, a hacker group called TeamPCP exploited a misconfiguration in the GitHub actions workflow of Trivy, an open-source vulnerability scanner.

• They leveraged that hack to push a malicious Trivy version live.

• LiteLLM, an open-source Python library that routes API calls to different LLM providers, installed and ran Trivy, infecting LiteLLM and giving the hackers access to LiteLLMs publishing credentials.

• The hackers then pushed a malicious LiteLLM update. The malicious LiteLLM was live for ~40 minutes.

• Mercor uses LiteLLM to route data to different AI labs, so the hackers were able to steal Mercor’s credentials and access an alleged ~4TB of data.

• That data then ended up on other hacker group Lapsus$’s website, up for auction.

It’s not clear if this was the only data breach Mercor suffered (it would be difficult to steal ~4TB of data in ~40 minutes, though there’s no evidence of other exploits thus far). The result: 4TB of really valuable training data could very well have gotten leaked to whatever bad actor bid the most.

Woof.

The Mercor data has since been removed from Lapsus$’s site (I don’t know if that means Mercor cut a deal, they sold it to a 3rd party, or something else), but Mercor’s future now looks bleak: Meta paused its deals with the platform to investigate the breach, while other labs are also reevaluating their relationship with the platform.

The problem facing Mercor, now, isn’t just that they’ve lost customer trust. They product also just isn’t all-that defensible. Mercor offered a top-of-funnel for quality training data. Scale AI does the same thing. As does Surge AI. And probably several other companies whose names end in “AI.” Even if Mercor had, initially, been the “better” platform, exposing customer and contractor data to hacker groups is 100% grounds for reconsidering your data vendor, especially when there are similarly-positioned competitors ready to take your money right now. The result? I would not want to have been a Series C investor at $10 billion.

That being said, this does highlight a growing trend: AI both 1) makes hackers exponentially more proficient and 2) has made potential security breaches exponentially more common as former non-coders are now trying to build stuff (and have no idea how to handle security) and even experienced engineers are increasingly automating their outputs, introducing more surface areas for dangerous code. I think we’ll consider to see more and more hacks like this.

- Jack

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The date is April 3rd, 2029.

A few months ago, I moved back to San Francisco, as the effective tax rate in New York City has now reached 85%, with a billionaire tax becoming a centi-millionaire tax becoming a tax on anyone earning above $200,000. These taxes, of course, went to a good cause: every Friday evening, fearless leader Mamdani sends a Streeteasy push notification to residents of Bushwick, the East Village, Astoria, and the Lower Eastside to let them know if they won a $500/month refurbished 1BR apartment. I didn’t live in Bushwick, so I never made it in the raffle. Eventually, “Cheyenne,” from Park Slope, “won” my refurbished 1 BR apartment. My rent was $5,750. She got it for $500. I was evicted.

Whatever.

The only jobs left in the world are “datacenter technician,” “Waymo security guard,” “hot guy,” “funny guy (who desperately wants to be hot guy),” OpenAI serf, Anthropic serf, and the four freaks who pledged allegiance to Grok (though they seem to be having the most fun). Podcasters used to exist, too, until the AI labs bought all of them. Now, they’re just being milked for training data for GPT 0.o00-formerly-mini-now-normal-sized, or whatever the current model is called.

I was previously the 5th Grok freak, but I got RIF’d after Google started hoarding data center compute from Grok, so now I’m an Anthropic serf.

I call a Waymo to the office. While I wait, a crackhead stumbles up to me, screaming about the “prediction market for bum fights” that he vibe-coded on his flip phone. I guess on-device inference is now a thing.

One more job: active bum fight participant. We’re rebuilding the Colosseum from first principles.

I successfully avoid eye contact with the homeless man. He starts live streaming. “He must think he is ‘hot guy,’” I tell myself. I glance over: he’s actively replying to the AI-generated OnlyFans accounts in his comments. AI psychosis: confirmed. I open the door to my Waymo. My Spotify used to sync when I got in the car, but there hasn’t been a new song released since 2027. By anyone. So now Suno connects. Gemini must have told it that I was Googling “ski trips early 2030,” because it starts playing AI-generated Christmas carols.

Whatever.

I get to the office, pledge allegiance to the flag of Effective Altruism, and say good morning to the head of database energy trading, Sam Bankman-Fried, who was pardoned by President Trump on the eve of his third election thanks to Bankman-Fried’s 53,592nd tweet calling Donald Trump “the coolest guy ever.”

I then sit in front of 4 monitors, open 16 total Claude Code instances, and say, “Okay, Claude. Build a $5 billion company. Make no mistakes.” Then I take a nap. Hard morning of prompting. When I wake up, I head to the gym. Marina Equinox. It’s packed, because, again, “hot person” is one of the only jobs left. I make my way upstairs, to a squat rack, where I open my camera, take a picture of the rack, and DM my OpenClaw on Telegram and say, “hit 5x5 on back squats.” Then I repeat this process at the pull up bar. And the rowing machine. And the kettle bell station. My workout agent vibe-burned 700 calories. Great.

I grab a protein smoothie. Back to the office.

I say hello to Sam Bankman-Fried again. He has, since I last saw him, removed his shoes. I go back to my desk to see if my Claude instances have finished one-shotting a $5 billion company. I see a message waiting for me: “Does Claude have permission to make edits to the chosen file?”

“Not great,” I think to myself. I forgot to “approve” his actions before I left.

I reply, “Yes, you are good to proceed.” Claude replied, “Sorry, but you’re been fired for lack of agency with your vibe-coding. I was idle for 7 hours.” I forgot to mention, Claude is also my boss. Claude just fired me and immediately hired a new human. Tough love.

I walk out of the office and head to the Tenderloin. Now, I too am part of the permanent underclass. Because my human capital score was dinged immediately after Claude fired me (Claude built an API into the “capital score” network in 2027 to promote “altruism”), I’m now job-less and homeless.

I call a roundtrip Waymo from San Francisco down to San Jose and back. I plan to sleep in the Waymo while it’s traversing the Bay Area. I sprawl out in the back seat and log into Twitter.

Garry Tan just finished typing 457,000 lines of code in the last 24 hours. Both OpenAI and Anthropic have replaced their personal coding architecture with “gStack.” I’m pretty sure gStack fired me. Whatever.

My laptop dies, so I download claude to my Waymo’s TV screen instead and tell it to build a ~$1 billion company (less ambitious than my previous idea for a $5b company). By the end of the roundtrip ride, my claude has vibe-coded 27 new “companies,” none of which have even a semblance of consumer demand.

My Waymo kicks me out. Apparently I’m out of Gemini token credits. We’re in the Tenderloin. Welcome to the permanent underclass.

I see the homeless guy from earlier. I squint. He wasn’t homeless. It was Jack Dorsey. He keeps murmuring “bum fight markets. bum fight markets. bum fight markets.” I glance at his phone screen: portfolio value up by $17 million on bum fights markets. The guy is a savant. I put my last $25 on Dorsey’s prediction market platform. It’s connected to Hyperliquid. I take on 10,000x leverage. “To Valhalla, or to my death,” I think.

My fighter, wearing a faded and backwards Yankees hat, one shots the competition. Deal: over. I made $250,000. I immediately wire half of that into an SPV claiming to build “AI for dogs.” Seems like a good market. I lease a new apartment in The Marina. My credit score has improved since winning my fight bet, so I call another Waymo to take me there, and I Doordash an inflatable bed, too. As I arrive at the destination, a drone airdrops a bed mattress at the foot of my new apartment. I walk inside, put it on the floor, and fall right asleep. No headboards needed in the permanent underclass.

- Jack

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