How do you save for retirement?
I'm writing a story for us about how US entrepreneurs save for retirement. I would love to hear what has made it easy or possible for you to save. What strategies, tools or people you've leaned on. And this question is open to people in all countries—I'm just having a hard time tracking down anyone outside the US who wants to chat about this!—Lex
This question is part of our Ask The Legends Series. Legends are invited to answer in the comments. Just sign in and comment on this post. Your experience helps our community and some of your quotes will be featured in our newsletter for added visibility.
Last updated: July 22 at 9:33pm CT | This post is live updated through Friday
Welcome back for another week in the wild world of small business! Below you'll find the top stories I think you should know about as a solo business owner, along with my take on why they're important.
We're now producing this series every week and some of you have asked for a dedicated newsletter. Once we switch the Magic Pages in the next month, that will be possible. In the meantime, I sent these out on Thursdays and keep the blog live updated all week.
Here's what's shaping up this week...
Thanks for reading this week’s free Where’s Your Ed At newsletter. Friday’s premium newsletter will ask the simple question: Is Oracle dying?
It’s been one year since I launched the premium newsletter, and I’ve decided to extend the discount on annual subscriptions. Between now and 12AM ET, July 26, you can get a permanent annual rate of just $60— a $10 discount on the usual price of $70 — for life. Click here for the offer.
In addition to getting access to the entire back catalog of premium posts, you’ll also receive one additional post each week — usually anywhere between 10,000 and 20,000 words — covering the most pressing topics in the AI bubble — the best value in tech analysis. Highlights include the Hater's Guide To The Memory Crisis, a guide to how AI made everything more expensive, How OpenAI Kills Oracle (which pairs nicely with the Hater's Guide To Oracle), The Hater's Guide To NVIDIA, The Hater's Guides To Private Credit and Private Equity, and how the entire AI Compute Demand Story Is A Lie.
Soundtrack: Dillinger Escape Plan — Black Bubblegum (2007)
This is Life as a Sacred Text 🌱, an everybody-celebrating, justice-centered voyage into ancient stories that can illuminate our own lives. It‘s run on a nonprofit, so it’s 100% NAZI FREE. More about the project here, and to subscribe, go here:
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Tonight begins the holiday of Tisha B'Av, during which Jews mourn the destruction of the First and Second Temples, the expulsions from Spain and elsewhere, and many other harms and calamities.
(Reminder: If you're fasting, drink lots of water now, and there are many, many reasons not to fast; if you have one, it's a mitzvah to eat.)
Here's a sentence that stopped me in my tracks last week: "The statement that 'the cemeteries are full of indispensable people' is just as true of nations, and in particular the US":
https://crookedtimber.org/2026/07/16/55382/
The writer is John Quiggin, writing about the fact that, under Trump, the world has raced through a series of seismic shifts in how it organizes itself, rushing to fill an America-shaped void in its dealings.
This is a subject that's very much on my mind. As November Kelly says, Trump inherited a poker game rigged in his favor and then flipped the table over because he resented having to pretend to play at all. The "international rules-based order" that gave America oversight and control over the world's militaries, finances, trade, and communications was always a better deal for America than it was for the rest of the world.
One of 2026's better tech-related coinages is "dickover," John Gruber's term for
a modal panel, popover, or curtain presented by a website or app, deliberately obscuring its own content to frustrate the user with an unwanted, unnecessary, mandatory interaction; e.g. asking the user to accept “cookies”, subscribe to a newsletter, install the website’s mobile app, agree to terms of service, or anything else that the user couldn’t give two shits about.
https://daringfireball.net/2026/05/what_is_a_dickover
These are bad everywhere, but they are especially terrible in the UK and EU, where websites practice a form of malicious compliance to the GDPR, Europe's landmark privacy law. Under the GDPR, websites are required to secure your affirmative consent to process your data. The obvious way that websites should respond to this is by not collecting your data unless there's a damned good reason for it, but the actual response is to repeatedly shove cookie-consent dialogs in your face before letting you use the site.
Squarespace jacked their prices up this week and customers are livid. I've spent a few hours wading through social media posts and replies about whether it's time to leave and what better options exist. Some people are offering a single platform answer ("This is why I'm on WordPress") while others are pointing out that it's not super cost effective to redesign an entire website over a $100 extra bucks a year.
But there's a third group of people who are realizing we've struck an iceberg and we need to start preparing our own lifeboats.
I have long thought the answer to Squarespace's demise was web designers building their own cooperative platform. But it's not just them that we need to be worried about.
What's the role of your website?
Websites have become (seemingly) less important as more of us build a presence everywhere across the internet. With Squarespace raising prices, a lot of us are wondering if we still need a site or how much website we need. How important is your website? Do people find you there? What role(s) does it play in your business?
This question is part of our Ask The Legends Series. Legends are invited to answer in the comments. Just sign in and comment on this post. Your experience helps our community and some of your quotes will be featured in our newsletter for added visibility.
Last updated: July 18 at 5:17pm CT
I keep expecting the news to slow down since it's the middle of summer, but it is showing no signs of that. Legislators worldwide are passing all kinds of crazy things (lots more social media bans on the horizon), the AI companies are racing to make their IPOs happen, and everyone else is just trying to keep up.
I'm paying attention to the tech tools and policy changes that affect our small businesses and delivering you the most important headlines every week.
Here's what's shaping up this week...
The theory of markets goes like this: even the best of us can fall prey to selfishness and rationalization, so let's arrange society so that people acting on their most selfish impulses end up producing benefit for all of us. That'll be easier and more reliable than convincing everyone to be more generous.
How do you arrange society so that selfishness produces public benefit? With markets. Faced with relentless competition, the most effective way to accumulate and retain wealth is by striving to make your wares cheaper and better. In a competitive labor market, we can secure fair treatment for workers without labor law or unions – bosses who treat their workers badly will lose them to better bosses. Just "align the incentives" and let markets do the rest.
This is an area where there's broad overlap between the left and the right. Chapter one of The Communist Manifesto is Marx and Engels' love letter to the incredible power of markets to improve everyone's material conditions by increasing production while lowering costs:
https://www.nytimes.com/2022/10/31/books/review/a-spectre-haunting-china-mieville.html?unlocked_article_code=1.yFA.YcmQ.KuTFFpUAnlmt&smid=url-share
This is Life as a Sacred Text 🌱, an everybody-celebrating, justice-centered voyage into ancient stories that can illuminate our own lives. It‘s run on a nonprofit, so it’s 100% NAZI FREE. More about the project here, and to subscribe, go here:
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Tisha B'Av (literally: the Ninth of Av) is the day on which Jews grieve the destructions of the First and Second Temples; the expulsion of Jews from Spain in 1492; massacres during the Crusades, and more.
The time from the 17th of the last month, Tammuz–marking the Romans breaching the walls of Jerusalem before the fall of the Second Temple–until Tisha B'Av is called the Three Weeks, a time in which many observe practices connected to mourning like not holding weddings, getting hair cut, or listening to music. The time from the very beginning of the month of Av (which began yesterday) until Tisha B'Av is called, yes, The Nine Days, during which even more mourning practices are observed.*
How do you handle LinkedIn with multiple audiences or businesses?
For those of you who are both employed and running a business, how do you approach LinkedIn?
I'm an artist, podcast host, and film industry professional. I want to continue working in film, but I'm also realizing that some of my skills and experience could translate into adjacent industries like advertising, marketing, creative strategy, communications, or community engagement.
Because of that, I feel stuck when it comes to LinkedIn. I'm not sure what to post, who I'm talking to, or how to balance multiple goals on one profile.
Do you focus on the work you're currently doing, the work you want to do next, or a mix of both? How do you connect with people when you have multiple audiences and potential career paths but only one LinkedIn presence?
I'd love to hear how others navigate this.
This question is part of our Ask The Legends Series. Legends are invited to answer in the comments. Just sign in and comment on this post. Your experience helps our community and some of your quotes will be featured in our newsletter for added visibility.
Thanks for reading this week’s free Where’s Your Ed At newsletter. As I said last week, I’m taking the rest of this week off, so there won’t be a premium on Friday. That said, if you aren’t already a member, now’s a great time to subscribe.
To celebrate the one year anniversary of the premium newsletter, I’m offering a sale on one-year subscriptions. Between now and midnight July 22, you can get a permanent annual rate of just $60— a $10 discount on the usual price of $70 - for life. Click here for the offer.
In addition to getting access to the entire back catalog of premium posts, you’ll also receive one additional post each week — usually anywhere between 10,000 and 20,000 words — covering the most pressing topics in the AI bubble - the best value in tech analysis. Highlights include last week's Hater's Guide To The Memory Crisis - a guide to how AI made everything more expensive - How OpenAI Kills Oracle (which pairs nicely with the Hater's Guide To Oracle), The Hater's Guide To NVIDIA, The Hater's Guides To Private Credit and Private Equity, and how the entire AI Compute Demand Story Is A Lie.
Today’s piece is one of the largest free newsletters I’ve ever written, and pulls together the last six months of my work.
The "designated survivor" is one of the weirder aspects of America's (very, very weird) political system.
Each year, during the State of the Union address, when both houses of Congress and the President are all under one roof, a single political figure, in the line of succession for the presidency, is spirited away to a hidden bunker, just in case the US legislative and administrative branches are decapitated in a single, spectacular terrorist strike:
https://en.wikipedia.org/wiki/Designated_survivor
Initiated during the 1950s, designated survivors are a paranoid relic of the Cold War, but they're also a relic of an era when America was a less chud-dominated, more technocratic land. It's a longtermist sort of procedure, in stark opposition to vibes-based MAGA chaos in which the Mad King makes daily announcements of new wars, tariffs, monuments, and existential threats to the nation.
How delightful! A fresh Legends mixer is upon us! Here's everything you need to know to have a great time and get some good connections outta this.
The format of this mixer is different than our usual. It's discussion rooms that you self-select into.
This is Life as a Sacred Text 🌱, an everybody-celebrating, justice-centered voyage into ancient stories that can illuminate our own lives. It‘s run on a nonprofit, so it’s 100% NAZI FREE. More about the project here, and to subscribe, go here:
Sign up for Life is a Sacred Text
Life is a Sacred Text is about truth & transformation, with ancient stories serving as mirrors & lights. Collective liberation. Everybody-celebratory.
As many of you know, about a month ago Pope Leo issued an encyclical –a special letter to bishops– on the use of AI. There, he wisely noted that though technology is neither “a force antagonistic to humanity” nor “inherently evil,” it can certainly be problematic when used badly. And, he continued:
He called on the tech industry to avoid
"I often wonder what the Vintners buy/One half so precious as the Goods they sell" -The Rubáiyát of Omar Khayyám
I first encountered that quote from someone extolling the virtues of bookstores, and it stuck with me, because for most of my childhood, every bookstore visit ended with me broke and wishing I'd had three times as much to spend.
As a larval hyperlexic, I just didn't understand what a bookseller could possibly buy with my money that was better than the books they already had? Of course, then I became a bookseller and discovered that Sturgeon's Law ("90% of everything is shit") applies to a bookstore's wares as much as it does to anything else. I also acquired a monthly rent obligation and discovered just how important money could be.
Nevertheless, Omar Khayyám's question stuck with me, especially when I fell down a years-long rabbit-hole of learning about scams and the finance sector (but I repeat myself). Every get-rich-quick schemer will tell you that they've found the infinite money hack, which they will sell to you for a remarkably reasonable sum. Likewise, every stock picker claims they can outperform a simple low-load index fund, and all they ask of you is a few hundred basis points in exchange for multiplying your wealth beyond the dreams of Creosote. Neither one has a good answer to Khayyám's question: if you can make all the money with your amazing system, why do you need my money?
You've left your corporate life behind to have more freedom choosing your clients and your projects, but there's one thing you need to solve. What do you call yourself now that there's no org chart?
Titles carry a surprising amount of weight. They offer search terms clients use to find you on LinkedIn, Google or ChatGPT. They give language to your referral partners for how to talk about you with potential leads. And they shape how client teams see your role once you begin an engagement. No wonder we're always looking for better words to describe what we do. Our opportunities and income hinge on it.
One title has blown up in the last few years: Fractional leader. Former executives shifting into self-employment add the label in front of their previous title. Fractional CMOs, Fractional CFOs, Fractional CTOs, even Fractional CEOs are everywhere now. An article in Harvard Business Review stated that, in 2022, a mere 2,000 people used fractional as part of their job title on LinkedIn. Two years later, that grew to more than 110,000 professionals.
Despite its rise in popularity, entrepreneurs debate whether or not the fractional title is actually helpful or hurtful to your business development. Some say it helps them get found and communicate their role faster. Others say it makes structuring engagements harder and it confuses clients unfamiliar with the term.
How do you make the most of a conference?
It's conference season. We all know conferences are good for making new connections but I'm curious how you make the most of the opportunity. It's getting more expensive to travel and some of us can only make one or two of these a year if we're not paid to be there. How do you use your time before, at and after a conference to make sure you get a return on your investment?
This question is part of our Ask The Legends Series. Legends are invited to answer in the comments. Just sign in and comment on this post. Your experience helps our community and some of your quotes will be featured in our newsletter for added visibility.
Here's an irony: the "gig economy" is a statistical black hole. Workers, customers and regulators know very little about the most basic aspects of it: how much workers get paid, for example, or much unpaid time on the clock a worker puts in before they get a job from the app.
The reason this is ironic is that the "gig economy" is dominated by a handful of massive, data-driven firms that know the precise, up-to-the-second answer to these questions. The problem is that they won't share the data. Of course, workers and customers have the data, too, but our data is widely diffused, with each worker and each customer only representing a single, infinitesimal pixel in this massive picture.
Most of our industry-wide figures about the sector come from painstaking, expensive survey work. The expense and effort involved in conducting this analysis means that the public's understanding of the gig companies' business is fragmentary and thin.
But every now and again, we get a flashbulb glimpse of the full picture. One of those glimpses was captured by David Weil, the former labor standards boss at the US Department of Labor. In 2024, the Massachusetts Attorney General sued Uber over worker misclassification, with Weil serving as an expert witness, who was able to access the raw data on Uber's business operations.
Hi premium readers! I’ll be taking a week off of the premium next week — July 17 — to have some well-earned rest. This will mark only the second time I’ve missed a premium piece since I started this newsletter in June 2025, and I hope you’ll forgive me for the (short) break.
Don’t worry. Today’s piece is also an absolute banger.
Everything’s more expensive, and it’s all AI’s fault.
An AI data center is full of servers, which are in turn full of (for the most part) NVIDIA GPUs. Each NVIDIA GB300 has two B300 GPUs, the two of which have 576GB of High Bandwidth Memory (HBM, or HBM3e to be specific), and a CPU, which has 480GB of lower-power LPDDR5X RAM (the kind usually used in cellphones and other mobile devices). These systems tend to be sold in an NVL72 rack with 18 compute trays, bringing us to 36 GB300s, for a total of 20.7 terabytes of HBM and 17 terabytes of LPDDR5X RAM, and that’s before you get to the RAM associated with the high-speed networking gear and other associated components.
While the AI bubble is primarily a material phenomenon (driven by the calculation that bosses are easy marks for a sales pitch that sees them replacing workers with software), there is an inescapable ideological component to it: the desire for a world without people in it:
https://pluralistic.net/2026/05/13/vibe-governance/#k-hole
If you'd like an essay-formatted version of this thread to read or share, here's a link to it on pluralistic.net, my surveillance-free, ad-free, tracker-free blog:
https://pluralistic.net/2026/07/10/posthuman-as-in-no-humans/#hell-is-other-people
This is Life as a Sacred Text 🌱, an everybody-celebrating, justice-centered voyage into ancient stories that can illuminate our own lives. It‘s run on a nonprofit, so it’s 100% NAZI FREE. More about the project here, and to subscribe, go here:
Sign up for Life is a Sacred Text
Life is a Sacred Text is about truth & transformation, with ancient stories serving as mirrors & lights. Collective liberation. Everybody-celebratory.
So I thought it'd be fun, as we've done occasionally in the past, to share biographies now and then of Jews To Know throughout history. Have a look and offer your thoughts?
Today: The naked Jewish mystic possibly Sufi, probably Kabbalist Persian-Armenian likely gay teacher in Mughal India whose life was even more colorful than that topline description. Come and learn.
There's plenty of reasons to be skeptical of centrists who bemoan "political polarization" and call for a politics that abandons the "tribalism of left and right."
Obviously there's the false equivalence: on the right, you have fascists who want to send masked, armed goons into the streets to beat, kidnap and murder your neighbors. On the left, you have calls for higher taxes, unions, environmental impact reviews for data-centers, and an end to the genocide in Gaza.
"Leftist extremism" is moving some zines around:
https://www.theguardian.com/us-news/ng-interactive/2026/jun/24/prairieland-texas-ice-protests-zines
If you liked this piece, you should subscribe to my premium newsletter. It’s $70 a year, or $7 a month, and in return you get a weekly newsletter that’s usually anywhere from 5,000 to 18,000 words, including vast, detailed analyses of NVIDIA, Anthropic and OpenAI’s finances, and the AI bubble writ large (updated to version 3.0 a few weeks ago). My Hater's Guides To the SaaSpocalypse, Private Credit and Private Equity are essential to understanding our current financial system, and my guide to how OpenAI Kills Oracle pairs nicely with my Hater's Guide To Oracle.
This week, I published the Hater’s Guide to Softbank — a sordid tale of tech’s most degenerate gambler, who, thanks to a couple of early lucky wins, has managed to set the foundations for the AI bubble’s biggest (and possibly most gratifying) downfall. And, on Friday, I’m going to take a deep dive into the memory industry — and the reason why you can’t afford a new gaming PC.
Subscribing to premium is both great value and makes it possible to write these large, deeply-researched free pieces every week.
Soundtrack: Mastodon — Streambreather
For a minute there, it looked like Big Tech was on the ropes. Over the past decade, countries all over the world have gotten antitrust fever, from South Korea to Singapore, Europe to Australia, and even China:
https://pluralistic.net/2025/06/28/mamdani/#trustbusting
Even more important: these international trustbusters shared a common enemy with Biden's antitrust enforcers, like Lina Khan (FTC), Rohit Chopra (CFPB) and Jonathan Kanter (DoJ Antitrust Division), who pursued the most aggressive antitrust agenda America has seen since Jimmy Carter and Ronald Reagan killed antitrust enforcement a half century ago.
This international collaboration was an especially rich and productive one. Today's global trustbusters have opportunities for collaboration that their Gilded Age predecessors could only dream of.
Soundtrack: Ozzy Osbourne — Mr. Crowley
A lot of people have been making a lot of fun of the SoftBank 46th annual shareholder meeting and Masayoshi Son’s (to quote Bryce Elder of the Financial Times) Untethered Goose Game, specifically referring to slides that, well, looked like this:
As funny and silly as these slides might be, they’re actually very indicative of the mindset behind SoftBank. Each one of those golden eggs refers to a trillion yen (about $6.15 billion) in the Net Asset Value (NAV) of SoftBank’s holdings, with the minus referring to its debt.
It’s actually very simple, especially if you know anything about geese.
In the mid-1970s, my dad – then a budding computer scientist, subsequently a math teacher – brought home my first computer: the CARDiac, a Turing-complete, all-cardboard papercraft computer that you could write and execute programs on:
https://en.wikipedia.org/wiki/CARDboard_Illustrative_Aid_to_Computation
CARDiac stands for "CARDboard Illustrative Aid to Computation," and it was created in 1968 at Bell Labs as a way to teach high schoolers how computers worked. I wasn't anywhere near high school age (I think I was in third grade?) but the CARDiac was revelatory. The year before, I'd had access to a teletype terminal and acoustic coupler that let me operate a PDP machine at the University of Toronto, and I'd been endlessly fascinated with the possibilities. I wrote simple BASIC programs, chatted with ELIZA, and messaged other system users, one keystroke at a time, all on paper (the terminal didn't have a screen, just a printer, and we fed it 1,000' rolls of paper towels my mom brought home from her kindergarten classroom, which I then rolled back up so she could put them back in the bathroom for the kids to dry their hands on).
Interacting with a computer in real-time was captivating, but it wasn't until I assembled and used the CARDiac that it all snapped into place. With the CARDiac, you composed simple programs with pencil and paper, then followed instructions that directed you to move paper tokens in and out of various slots representing memory cells and an accumulator. All an electronic computer does is repeat these crude mechanical operations, millions of times per second, using microscopic transistors. None of that action can be observed with the naked eye, of course. If you had a very sensitive multimeter and a very good microscope, it's conceivable that you could indirectly watch this intricate dance, but only on very early processors, and only if you drastically slowed down their operations.
This is Life as a Sacred Text 🌱, an everybody-celebrating, justice-centered voyage into ancient stories that can illuminate our own lives. It‘s run on a nonprofit, so it’s 100% NAZI FREE. More about the project here, and to subscribe, go here:
Sign up for Life is a Sacred Text
Life is a Sacred Text is about truth & transformation, with ancient stories serving as mirrors & lights. Collective liberation. Everybody-celebratory.
Over here in These United States, we're just about at Fourth of July weekend– during an election year, while white supremacist Christian nationalism is running the government and the 250th anniversary of the Declaration of Independence is being marked. It's... a lot.
So I thought I'd remix something I did a couple of years ago, using the base text getting celebrated this year. So.
But first, I want to remind you that our first LEARN, TO DO is in just one week. For those of you less familiar with Mariame Kaba's work, she is, truly (as far as I can tell, and I do not say this lightly) one of the most important and visionary doers and thinkers of our era, and I believe that at some point will be more universally regarded as such.
(My friends, I'm not picking these people capriciously! Every single one of these sessions is going to be paradigm-shifting, and I mean that.) So this session, as all of these, is really a special opportunity to learn from truly extraordinary voices at a pivotal moment in our nation's history.
This is Life as a Sacred Text 🌱, an everybody-celebrating, justice-centered voyage into ancient stories that can illuminate our own lives. It‘s run on a nonprofit, so it’s 100% NAZI FREE. More about the project here, and to subscribe, go here:
Sign up for Life is a Sacred Text
Life is a Sacred Text is about truth & transformation, with ancient stories serving as mirrors & lights. Collective liberation. Everybody-celebratory.
Today's going to be an Extra Special Double Thursday– two emails today! Hey, it's a long weekend, space 'em out however you like, just read 'em both as you like!
(I considered just embedding the second into the first but why? You can handle this. 😉)
This first one jumps right into the hard question embedded in the Declaration of Independence (turning 25o this weekend, wild). The one to come in a few hours is more of a slow slide towards the deeper end, and that one is getting shared more broadly.
Regardless, not all of you have signed up for this yet and I am telling you that if you do not know why Mariame Kaba is one of the most important, visionary voices working today then you will understand by the end of this. Not overstating, here.
Finding your role in the work with Mariame Kaba, July 8, 7ET/4PT.
I'm not kidding.
Even if you feel that you have your role in the work this conversation will be worth your time and you will learn so much, as will we all. Click through and just do it already.
Trump’s $1.4 billion crypto disclosure0:00/647.3946261×
Listen to me read this post here (not an AI-generated voice!), subscribe to the feed in your podcast app, or download the recording for later.
President Donald Trump’s most recent financial disclosure reveals that he earned more than $1.4 billion in income from his cryptocurrency businesses alone last year. These crypto-related ventures account for more than half of the $2.2 billion in income Trump reported overall, through an unprecedented self-enrichment scheme that has made him and members of his family fabulously wealthy while investors who bought into his projects have lost money hand over fist. Forbes most recently estimated Trump’s personal net worth at $6.5 billion, a staggering increase from his estimated $2.3 billion valuation as a private citizen in 2024.1
The bulk of the crypto windfall came from Trump’s two primary crypto ventures. He brought in $635 million thanks to a licensing agreement with “Celebration Coins” — likely an erroneous reference to Celebration Cards LLC, one of the firms in the web of companies responsible for the $TRUMP memecoins. Another $529 million came via sales of World Liberty Financial’s $WLFI token, whose buyers are not named in the disclosure but include crypto billionaire Justin Sun.
The filing also reports more than $260 million from equity sales in Stablecoin Holdco LLC and WLF Holdco LLC, both entities in the World Liberty Financial tangle of companies. Again, the buyers are not disclosed, but some of these proceeds are likely his share of the $500 million investment by the United Arab Emirates into World Liberty Financial, inked shortly before the White House approved the sale of highly restricted AI chips to the country [I83, 87, 93, 94]. That we know the investment came from the UAE, which was simultaneously negotiating deals with both President Trump and World Liberty-connected Steve Witkoff [I95], is known only thanks to outside reporting by the Wall Street Journal.
Trump’s family members are also profiting handsomely from their roles in the family’s crypto empire, and from their own crypto-related ventures. Industry groups clearly see them as conduits to favorable political outcomes — Donald Trump Jr. was named to advisory roles at both the Kalshi and Polymarket prediction market platforms, for example, and likely not solely on the basis of his business acumen. That segment of the industry has enjoyed a particularly favorable shift in regulatory stance, with the CFTC — under the control of a single Trump loyalist Commissioner — intervening to fight back against state regulators in court cases against these firms [I101, 104, 105]. But because they don’t serve in formal roles, Trump’s family members are not required to file financial disclosures, leaving much of their earnings hidden from public view. Despite this, both sons have met with high-level officials from at least eight foreign governments since Trump’s re-election, to talk both business and policy.2
If you liked this piece, you should subscribe to my premium newsletter. It’s $70 a year, or $7 a month, and in return you get a weekly newsletter that’s usually anywhere from 5,000 to 18,000 words, including vast, detailed analyses of NVIDIA, Anthropic and OpenAI’s finances, and the AI bubble writ large (updated to version 3.0 a few weeks ago). My Hater's Guides To the SaaSpocalypse, Private Credit and Private Equity are essential to understanding our current financial system, and my guide to how OpenAI Kills Oracle pairs nicely with my Hater's Guide To Oracle.
This month, I published a two part series that took a deep-dive into the bubbles-within-a-bubble that make up the AI bubble — from the unsustainable and reckless growth of semiconductor companies, to the cults of personality surrounding Sam Altman and Dario Amodei. On Friday, I’ll publish my long-awaited Hater’s Guide to Softbank. You won’t want to miss it.
Subscribing to premium is both great value and makes it possible to write these large, deeply-researched free pieces every week.
Soundtrack — Queens of the Stone Age - Hideaway (Baloise Orchestral Arrangement)
It’s been an incredibly long few weeks, and as a result my previously-planned Hater’s Guide just isn’t possible within what little time I have left in this week, which is why I’m starting an ongoing series — Notes From The Bubble — where I’m going to dig into the various stories that have stood out to me in the last few weeks and what they mean for the greater tech ecosystem. It’ll be my weapon of choice going forward for the (few) weeks where a greater narrative is taking longer to pull together than usual.
I also think it’s time for something a little more light-hearted after a few hundred thousand words of deeply-researched financial nightmare fuel. As serious as the tech industry’s descent into cargo cultism has become, it’s really important to laugh at how disordered and goofy everybody has become as they realize that we’re flat out of hypergrowth ideas. Every time you see something stupid, desperate, ridiculous or disconnected from reality, know it’s a symptom of the greater fear that AI isn’t the next big thing, and that everything is an attempt to put off accepting that truth or, alternatively, create another hype cycle so we can avoid talking about it.
I know this all sounds a little reductive, but look at the current state of the tech industry. Meta is creating a Polymarket competitor. Snap is launching its third generation of AR glasses that nobody wants, I assume to compete with Meta’s AI glasses that are exclusively owned by influencers and people that should be banned from public restrooms. Microsoft has gone from loving OpenAI to loving Anthropic to loving open source LLMs and decrying the idea that any one company could control the entire AI ecosystem, somehow missing that Microsoft is the largest AI infrastructure provider in the world and is the reason that this industry exists. Google invested $75 million in movie studio A24 as part of some sort of nebulous AI partnership that will likely result in very little actually happening.
Oh, and you can now watch Instagram on your TV.
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Welcome back to another edition of Spiritual Practices for Terrible Times!
I think this is officially an ongoing series, wherein I share some cool things that some of the folks from the past have done that might be valuable for us today.
Today I'd like to share a practice from the great Rabbi Kalonymus Kalman Shapira (1889-1943), from the days before the war.
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A few weeks ago, I predicted that the AI industry would start pushing the concept of “loops” — effectively LLMs prompting LLMs and being left to their own, token-intensive devices — as a desperate attempt to get users to burn more tokens, I imagine to create more revenue.
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Information is flowing in from everywhere, these days.
There are so many things to care about, and, yeah, reasons to feel overwhelmed, angry, frightened, determined—or, maybe, all of the above.
So it’s been a big week for me after I published an exclusive covering OpenAI’s audited financials from 2024 and 2025, with reactions ranging from “oh my god, OpenAI spent $34 billion to make $13.07 billion in revenue!” to “actually, it’s good the company lost $21 billion.”
And that, my friends, is the Silicon Valley Bubble writ large – an industry that grew rich and famous off the back of a mythical pragmatism and meritocracy that’s morphed into a pseudo-cult built to protect venture capital investments at the cost of reality.
OpenAI lost $21 billion in 2025. $867 million – or around 6.6% – of its revenue came from SoftBank, I posit (though cannot confirm) is something to do with its supposed “Crystal Intelligence” (formerly Cristal Intelligence) initiative with OpenAI, announced in February 2025 as part of the alleged formation of SB OAI Japan, which only actually formed in November 2025.
I severely doubt that SoftBank was a significant cost center for OpenAI given the timeframe, which means that this likely inflated its revenue significantly, and in a way that was disproportionate to its expenses.
Issue 106 – A tremendous birthday present0:00/2090.3702041×
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I was hard at work building Tech Influence Watch, my campaign finance tracker that helps you follow how the cryptocurrency and artificial intelligence industries are influencing politics, hence the slightly longer gap between recap issues. The industry spending didn’t slow down in the meantime — if anything, it’s ramped up as more states held their primaries — and crypto-related Trump corruption and legislative maneuvering has continued apace. That means there’s lots to cover, so let’s get right into it.
I helped Reuters with a recent report that concluded that, unlike their investors, “the [Trump] family always wins” in its crypto business deals. While the Trump family has profited $2.3 billion from their crypto ventures, according to Reuters’ estimates, investors have lost a conspicuously similar $2.3 billion. I saw a lot of reactions to the piece to the effect that investors didn’t “lose” money, they were merely paying for pardons or other benefits. But I think Reuters did a great job of highlighting the everyday people who’ve been suckered by the Trumps’ various crypto schemes, who genuinely believed they would make money if they bought the $TRUMP memecoin or shares in the family’s crypto-linked businesses. “When a stock has presidential backing in a way — at least from his sons — you would think it would go up,” explained one buyer of shares in ALT5 Sigma. (ALT5 Sigma is a Trump-linked treasury company that holds a significant quantity of $WLFI tokens issued by the Trump family’s World Liberty Financial [I90, 92, 98].) He’s a machinist who’s lost $32,700 — 79% of his initial investment — not someone pursuing a pardon or regulatory relief.1
And although that machinist expresses hope that his investment might recover, he may well be in for an even worse outcome. Alt5 Sigma, which recently renamed itself to AI Financial,a has reported in its most recent quarterly SEC filing that it is continuing to lose money, raising “substantial doubt about the Company’s ability to continue as a going concern within one year”.2 The company tries to soften this news with the claim that it has a “significant financial resource” in the 7.3 billion $WLFI tokens held in its treasury, but also acknowledges “significant market price risk” if it were to sell them.
The filing reports these tokens have a fair value of $703.4 millionb — a figure the company derives, in its own words, from “quoted (unadjusted) prices”: that is, the number of tokens × market price, with no discount for the position’s size and illiquidity. That “value” was stale almost immediately. In a June 10 disclosure, the company valued the same holdings at roughly $380 million, having lost more than $300 million in paper value in just ten weeks.3 Even that figure overstates what a sale could fetch, because a company in distress holding a fire sale on tokens issued by a related company is practically guaranteed to crash the token price. And furthermore, the firm acknowledges that all tokens are locked until at least late August, with some subject to extra conditions on sale.
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It's time again: We have the extraordinary privilege of being in a community with a ton of other insightful, thoughtful people who also engage deeply with hard questions about the stuff that matters–
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Today, I can exclusively report, based on audited financial documents viewed by this publication that have been independently verified by the Financial Times, that OpenAI lost around $38.5 billion in 2025, as well as other crucial details about the financial condition of the company.
Due to the seriousness of this story, I am not going to do very much editorializing, as the numbers speak for themselves.
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Life is a Sacred Text is about truth & transformation, with ancient stories serving as mirrors & lights. Collective liberation. Everybody-celebratory.
Trigger Warning: Racist and antisemitic violence / history
It's time to talk about scapegoating through one historical lens, and to share a little-known, 900-year old Jewish way of grieving collective harm that we can, and perhaps should, bring back now–for everyone.
The Second Circuit of Appeals, which in November 2025 heard oral arguments in Sam Bankman-Fried’s appeal of his November 2023 conviction [I96], has upheld the verdict and rejected Bankman-Fried’s request for a new trial with a new judge. I’ve purchased the full document so it’s uploaded to CourtListener’s RECAP archive.
The appeal was one of Bankman-Fried’s few remaining options after Judge Lewis Kaplan denied his motion for a new trial in April [No new trial].
Bankman-Fried tried to argue before the Second Circuit that his FTX cryptocurrency exchange was solvent before, during, and after its bankruptcy, and that its dramatic collapse was simply the result of a temporary liquidity squeeze caused by a sudden wave of withdrawals. (At various points he has made clear that his definition of “solvency” is his own, novel one.)
Indeed, some of FTX’s investments — particularly one in the Anthropic artificial intelligence firm, which develops the now popular Claude suite of AI tools — proved lucrative after FTX’s demise, and substantially helped to fund restitution to FTX’s customers.
End Citizens United’s Tiffany Muller on fighting big money in politics0:00/2889.8392291×
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Sixteen years after the Citizens United decision opened the floodgates to unlimited corporate spending in American elections, corporations and billionaires are regularly spending tens of billions of dollars on our elections. While many people are aware that interests like big oil, big pharma, and big banks spend heavily on elections, there are some newer entrants in this field that voters largely don’t know about. The cryptocurrency industry alone spent $130 million in 2024, and is on track to spend even more in 2026. Now AI is following the same playbook, with the same operatives running both campaigns.
I’ve spent the past two years tracking this spending through Follow the Crypto, which I just relaunched this week as Tech Influence Watch — an expanded real-time tracker covering both crypto and AI political spending across the 2026 cycle.
But crypto and AI are just the newest entrants in a system that was deliberately built to let them do exactly what they’re doing. To understand that system, I wanted to talk to someone who’s been fighting for years to dismantle it.
Tiffany Muller is the president of End Citizens United, the organization working to end the influence of big money in politics. In this conversation, we talk about what Citizens United enabled, how it’s shaped policy outcomes on everything from climate to gun control to healthcare, what’s different about this newest wave of tech industry spending, and what it would actually take to fix the system.
I’m launching Tech Influence Watch as AI follows crypto into politics0:00/1218.7654881×
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I’ve been running my website Follow the Crypto since 2024, tracking the cryptocurrency industry’s influence on our democracy. The industry spent more than $130 million buying the 2024 elections, and the strategy worked. Pro-crypto politicians have proposed or passed industry-drafted legislation that threatens to open the floodgates to even more predatory crypto products, regulatory agencies were gutted, and crypto executives bought direct access to the President and positions in the White House. Now the artificial intelligence industry is following the same playbook.
Continuing to track only crypto would mean missing half the story. The same operatives are running both campaigns. Josh Vlasto, longtime adviser and spokesperson for Fairshake — the cryptocurrency super PAC network responsible for the bulk of crypto’s 2024 spending — is now simultaneously heading Leading the Future, a pro-AI super PAC network.1 Chris Lehane, the political consultant and Coinbase board member who helped establish Fairshake and famously told Coinbase employees who questioned whether a crypto voter bloc existed that they would simply invent one,2 is now also an OpenAI executive and one of the people behind the Leading the Future PAC network.3 The same venture capital firms are funding both: Andreessen Horowitz, a crypto heavyweight in the 2024 elections, is now splitting its political spending across crypto and AI PACs.
The PACs may look different from the outside, but they’re increasingly the same operation with aligned goals: deregulate the tech sector, slash consumer protections, and allow tech companies to capture even more enormous profits at the expense of everyday people.
So I’ve expanded the site to track both. It’s now called Tech Influence Watch, and it documents more than $400 million (and counting) in contributions from crypto and AI companies and their executives this election cycle. When two industries with shared backers and shared operatives are spending this much to write their own regulations, someone needs to be watching.
I was reading Hacker News the other day, as one does, and a post titled "Using AI to write better code more slowly" had climbed near the top. I read it, and then I just kinda sat there chewing on it while I worked for the afternoon. Ultimately, I think Nolan has named something I'd been turning over for months without quite being able to articulate.
I've been writing about AI tools for a little while now, With the general tone being somewhere between lightly skeptical and inquisitive. Right now I'm basically of the belief that AI leaves the hard problems exactly as hard as they were before. The easy stuff is inarguably easier, and boilerplate is functionally eliminated, but it isn't the society-ending inflection point everyone keeps fretting about.
What Nolan's post did was clear a path through the part of the question I hadn't worked out.
Before I'm branded a hater or in denial, let me be clear about where I'm standing: I'm enthusiastic about these tools. I use them every day, and I've built things in the last year (including a business) that I would not have started, much less finished, without an agent (or several) at my elbow. I regularly teach, encourage, and recommend the use of these tools at work and as a freelancer
Issue 105 – The new boogeyman0:00/1960.5670981×
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The spat between World Liberty Financial and Justin Sun has escalated to dueling lawsuits after both sides raced to the courthouse. Sun, who only just escaped fraud allegations himself after investing more than $200 million in Trump family crypto projects, is now accusing World Liberty of the very behavior he was accused of, while simultaneously trying to convey to Trump that he’s still a huge fan.
Commerce Secretary Howard Lutnick, who supposedly divested from his Cantor Fitzgerald financial firm by transferring it to his sons, was still the man GOP leaders tried to get on the phone when they discovered a Cantor-funded pro-crypto super PAC was planning to back Ken Paxton in the Texas Senate Republican primary runoff. And despite Lutnick’s supposed lack of involvement with his former firm, the $1.75 million planned ad was still nixed.
Crypto’s back to trying to convince politicians that voters care deeply about crypto, but a CoinDesk poll found that 76% of voters they polled don’t find it important to the upcoming elections. With 60% of respondents saying they think crypto will be a negative force in the economy, 73% disapproving of senior US officials having personal business ties to crypto, and 62% saying they don’t trust the Trump administration to properly oversee crypto, I’d be curious to know how many of those voters who said they do find it important feel that way because they are concerned about crypto’s current regulatory trajectory.1
Last month, the feud between the Trump family’s World Liberty Financial and its largest token investor, Justin Sun, escalated to furious tweets and legal threats after the project froze Sun’s WLFI tokens and refused to unfreeze them for months [I104]. Both sides have now filed near-simultaneous lawsuits against each other.
If you followed along with the recent joyful celebrations of the Artemis cruise around the moon, and took a moment to dive into the photographic archives of the mission, you might have noticed that all of the original images were shared by NASA on the venerable photo sharing service Flickr. What you might not know is… why?
First, some background for folks who might not know what Flickr is, or who may have forgotten. Flickr is a social sharing site for photography which was founded in 2004, and these days people might say that it shares some of its cofounders with Slack, though back when Slack started, everybody said that the company was started by some of the founders of Flickr. That’s because Flickr was arguably the most influential site of the Web 2.0 era, helping define everything from the user interface design to the bright colors to the easy way that developers could access data from the platform. A lot of the things that we take for granted on the modern social internet, like a friendly “voice” used to communicate to users, were pioneered by Flickr, and then quickly came to be considered standard expectations for the apps and sites that followed. It’s hard to imagine that sites from Tumblr to Grindr would have omitted their final “e”s without Flickr’s precedent.
Flickr spun out of a Canadian gaming company called Ludicorp, founded by Stewart Butterfield (later CEO/co-founder of Slack) and Caterina Fake (later an investor and chair of Etsy). The photo-sharing service was extracted from the pieces of a somewhat unsuccessful attempt at multiplayer gaming called “Game Neverending”, but it retained the playfulness of that game even as it became a social app. Flickr also inherited the fine-grained privacy controls and thoughtful community features of earlier social platforms like LiveJournal — along with being actively, intentionally moderated by actual humans who worked diligently to prevent destructive behaviors on the platform. This meant that, more than 20 years ago, this early photo sharing community typically had better social norms than people see on today’s social media apps. (A little side note: Part of Flickr/Ludicorp’s initial funding was with public money. What a remarkable way to fund lasting innovation!)
With all of these groundbreaking features, Flickr didn’t just inspire lots of other entrepreneurs to create a new wave of Web 2.0 startups, it also attracted millions of users who, for the first time, began taking photos with the primary goal of sharing them online. Prior to this moment, the earliest phones with decent cameras were coming to market (it would be years until the iPhone came out), and other photo services of the time were still often oriented towards taking film to processing facilities, and then having the professionals at those facilities scan the resulting images and post them to a clunky online service where you could tediously click through them in a virtual album. Until Flickr, photo sharing online was essentially still analog, even if the experience was technically happening online.
President Trump’s $TRUMP memecoin, down 42% since his most recent token-gated event only four days ago and 97% from its peak,a is poised to launch a new attempt to resuscitate prices.
The website has quietly introduced a signup page for a “members only, limited access” $TRUMP Coin Club, which it describes as “invitation-only luxury suites at the biggest sporting events in the world, private dinners, and the most elite and extraordinary experiences”. The club itself hasn’t launched yet, and the memecoin project has yet to formally publicize the waitlist registration.
Although tiny print amid the legalese in the website footer notes that “Club membership will be open to all qualifying community contributors; no purchase, holding, or ownership of $TRUMP or any crypto asset will be required”, the website prominently features a placeholder for a leaderboard that appears poised to rank holders. Like the $TRUMP project’s previous one-off events — a May 2025 dinner and a “gala luncheon” this past Saturday, both featuring brief Trump appearances — the leaderboard appears designed to rank members by both the amount of the token they hold and the duration they’ve held it, continuing the time-weighting approach implemented after holders immediately dumped their tokens following the first dinner.
The $TRUMP Coin Club website prominently features a token holder leaderboard, despite fine print claiming that no $TRUMP holdings are necessary for membership
No new trial for Sam Bankman-Fried0:00/518.825851×
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Sam Bankman-Fried is out of options.
Judge Lewis Kaplan has denied his motion for a new trial, and in doing so, closed off what was likely his last realistic avenue to escape his 25-year prison sentence besides his ongoing appeal to the Second Circuit — which is widely expected to fail.
Bankman-Fried had tried to withdraw his motion for a new trial, perhaps sensing that things were not poised to go in his favor after repeated questions as to whether his parents were writing his supposedly pro se filings for him, but Kaplan refused to let him slink away. Instead, he ruled on the merits and used the opportunity to condemn what he describes as Bankman-Fried’s ongoing, calculated campaign to rehabilitate his reputation — one that Bankman-Fried outlined in detail before he was even indicted.
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The cultural battles over AI have broken down over predictable lines in the past few years, with critics rightfully calling out the big AI platforms for training on content without consent, recklessly building without considering environmental impact, and designing platforms that are unaccountable because their code and weights (the parameters that describe how an AI model works) aren’t open for third-parties to evaluate. The AI zealots have done themselves no favors, by not only dismissing all of these valid criticisms, but by also making increasingly outlandish and extreme claims about the capabilities of the Big AI platforms, while simultaneously scaremongering about the brutal effect they’ll have on people’s lives and careers. It’s no wonder the public sentiment about AI has become so negative.
But a small cohort of us who are curious about LLMs as a technology, yet deeply critical of Big AI companies for their impact on society, have been asking what would “good” AI look like? Is it possible to make versions of these technologies that provide real benefits, and actually help people, without all of the attendant harms? We’ve had prior eras of machine learning tools that were useful technologies without being massively destructive — are the negative externalities intrinsic to LLMs in general?
We might have just gotten our first glimpse at an AI that’s actually good.
This is just one small example that I saw recently, in a very unexpected place, but I can’t get it out of my mind. It’s not a tool that every person in the world is going to use, but it feels a bit like the famous William Gibson quote, “The future is already here — it's just not very evenly distributed.” This might be a little tiny bit of a good AI future, and now we just need to distribute the same kind of thing to a lot more people.
Issue 104 – World Tyranny Financial0:00/1850.1198871×
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The Trump family’s World Liberty Financial is borrowing against its own thinly-traded token. New reporting suggests the company may have partnered with individuals connected to a US-sanctioned human trafficking operation. And Justin Sun, who was among the project’s earliest and largest investors, has denounced it as “‘World Tyranny,’ not ‘World Liberty Financial’” as his $75 million investment remains frozen.1
As the president’s family’s shady dealings continue to mount, SEC enforcement actions have collapsed to twenty-year lows. The CFTC says it doesn’t need staff when it has AI. The nominee for Federal Reserve chair is deeply invested in crypto and AI. And the new leader of the Justice Department is the guy who shut down the agency’s crypto enforcement despite an ethics commitment not to participate in crypto matters before divesting his own personal crypto wealth.
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Controversies are once again brewing around the Trump family’s World Liberty Financial project, which has promised since its 2024 launch to produce some kind of defi crypto trading application, but which has so far mostly just sold hundreds of millions of dollars’ worth of its own $WLFI token and issued a stablecoin.
It's been a decade since we lost Prince, and I wanted to take a moment to offer a look back at some of the pieces I've written over the years, and share some of the work I've done, and hopefully it will give you a chance to explore some aspect of his artistry or legacy that you haven't yet had a chance to discover!
Perhaps a good place to start: It's time to discover Prince — a set of starting points to look at Prince's musical catalog, with selected albums (with more than 40 albums to pick from, it can be overwhelming to know where to start!) and some playlists that I created specifically to help new fans find out exactly why we love his music so much.
Another comprehensive overview: Every video Prince ever made. I walked through all of the music videos Prince made over the four decades of his career, offering some info and context that might help you find which ones are most compelling (or weird!) and worth your time.
I've also gotten to guest on a number of podcasts and in other media over the years to discuss various aspects of Prince's career. Perhaps none was more exciting for me than talking about Prince's history of technological innovation for the official Prince podcast. Then, no less than the New York Times described me as a "Prince scholar" when it covered the discovery of the earliest known footage of Prince as a child. There are a bunch of other podcast appearances (see below) but these felt like the pinnacle of legitimacy for my career as a Prince fan.
I'd been using Claude Code for about a week when I asked it to scaffold a Laravel authentication module. It generated the routes, the controllers, the middleware, the views. Clean code. Well-structured. Proper separation of concerns. I skimmed it, nodded, ran the tests.
Green across the board. I pushed to staging, opened the browser, typed in credentials, and watched it redirect me to a 500 error. The middleware was checking for a session token that the login controller never set. The tests passed because the test helper bypassed middleware entirely.
I fixed it in ten minutes. But the thing that stuck with me wasn't the bug. It was how convinced I'd been, for about thirty seconds, that the AI had just written a flawless auth system. The code looked right. The tests said it was right. The only thing that caught the problem was actually trying to log in.
I want to tell you this was a one-time thing, that I learned my lesson and it never happened again.
[noted] is a new short-form companion to Citation Needed. I’ve been posting things like this to my microblog for a while — notes on new court filings, campaign finance disclosures, or newsworthy developments that shouldn’t wait for the next recap issue — and you can get a sense of what to expect there.
The new Fellowship crypto PAC has filed its first fundraising disclosure, reporting a $10 million contribution from Cantor Fitzgerald and $1 million from Anchorage Digital. Cantor Fitzgerald is the financial services firm Commerce Secretary Howard Lutnick turned over to his two twenty-something sons when he accepted his White House role.
The Fellowship PAC launched in September with an announcement that they had $100 million committed [I93]. They’ve more recently revealed that the PAC is headed by Jesse Spiro, the head of government affairs for the US arm of the Tether stablecoin issuer. Tether and Cantor Fitzgerald are closely linked — Cantor owns a stake in Tether and custodies a substantial portion of its reserves [I71]. Lutnick has personally vouched for the quality (not to mention the existence) of the stablecoin issuer’s reserves [I70], which the company seemed to hope would be sufficient after years of promising but never actually producing a full audit.
As I covered more recently, Commerce Secretary Lutnick’s sale of Cantor Fitzgerald to his children may have been financed in part with a loan from Tether — a transaction that, as law professor and former D.C. ethics counsel Kathleen Clark noted, “is in theory supposed to eliminate a conflict of interest, but in reality it creates a new one.” [I103] The sale to family members itself echoes Trump’s approach: rather than truly divesting, both men transferred control to their direct family when taking their government positions.
It’s rare that you get to see work that directly helps those who most deserve it, but I want to tell you about the opportunity we so seldom get to actually contribute in a way that we know will have real impact.
I’ve been on the board of the Lower Eastside Girls Club for about a decade, getting a front row seat to seeing what a truly community-focused and effective organization can do for those in need when things are done the right way. This is the model of what we want our public institutions to be — laser-focused on the needs of its members, extremely ambitious in its goals, and measurably effective in its outcomes.
I’m asking you to support the Girls Club in one of two ways:
The Girls Club serves girls who are amongst the most in-need in all of New York City, and boosts important measures like graduation rates to levels 15% higher than the district average. The way that the club does it is by providing year-round programming in the arts, STEM, civic engagement, leadership, wellness, college and career pathways, and much more — including a deep connection to a sense of community. All of this happens in a facility that is nothing short of magical, where there’s a green roof, a full recording studio, a commercial-grade kitchen, a wonderful crafting room, and even an actual planetarium. And all of these resources are made available to the girls entirely for free.
We shape our tools and thereafter our tools shape us.
You install an AI coding assistant. You type a prompt. It writes some code. You fix the parts it got wrong. You type another prompt. This is the loop, and for most people it stays the loop forever. Prompt, generate, fix, repeat.
I did this for about three months. It was useful. I built things faster than I would have alone. I explored codebases I didn't know. I generated documentation nobody else was going to write. The tool was good at its job, and I was good at asking it to do that job, and that was the whole story.
Then in December something shifted, and the story stopped being about a tool and started being about a system.
In just the last few weeks, we’ve seen a series of software security vulnerabilities that, until recently, would each have been the biggest exploit of the year in which they were discovered. Now, they’ve become nearly routine. There’s a new one almost every day.
The reason for this rising wave of massively-impactful software vulnerabilities is that LLMs are rapidly increasing in their ability to write code, which also rapidly improves their ability to analyze code for security weaknesses. These smarter coding agents can detect flaws in commonly-used code, and then create tools which exploit those bugs to get access to people’s systems or data almost effortlessly. These powerful new LLMs can find hundreds of times more vulnerabilities than previous generations of AI tools, and can chain together multiple different vulnerabilities in ways that humans could never think of when trying to find a system’s weaknesses. They’ve already found vulnerabilities that were lurking for decades in code for platforms that were widely considered to be extremely secure.
The rapidly-decreasing cost of code generation has effectively democratized access to attacks that used to be impossible to pull off at scale. And when exploits are less expensive to create, that means that attackers can do things like crafting precisely-targeted phishing scams, or elaborate social engineering attacks, against a larger number of people, each custom-tailored to play on a specific combination of software flaws and human weaknesses. In the past, everybody got the same security exploit attacking their computer or system, but now each company or individual can get a personalized attack designed to exploit their specific configuration and situation.
Now, we’ve had some of these kinds of exploits happening to a limited degree with the current generation of LLMs. So what’s changed? Well, we’ve been told that the new generation of AI tools, currently in limited release to industry insiders and security experts, are an order of magnitude more capable of discovering — and thus, exploiting — security vulnerabilities in every part of the world’s digital infrastructure.
These days, we’re all living in a constant state of crisis, foisted upon us by a world where those who are meant to keep things stable are the least stable factors in our lives. The chaos and stress of that reality makes it difficult to make any plans, let alone to make decisions if you have responsibilities for a team or organization that you’re meant to be leading. It’s easy to imagine there’s nothing we can do, or to feel hopeless. But a resource that just arrived served as a timely reminder for me that a crisis doesn’t have to be paralyzing, and we don’t have to feel overwhelmed when trying to plan how we’ll respond as leaders.
The topic of crisis has been on my mind again as I’ve been looking at the work of some friends who are the most fluent experts on the topic of crisis that I know, prompted by the release of Marina Nitze, Mikey Dickerson and Matthew Weaver's new book, Crisis Engineering.
There’s nothing more valuable than people who can step in during a moment of crisis and provide clarity, not just on how to make it through that moment, but how to seize that opportunity to actually make better things possible. A few years ago, at some of the most stressful and harrowing moments I’ve had as a leader in my business career, I got to connect with a remarkable team who ran towards the crisis that our organization was in, and helped our team get through that moment and not just persevere, but to thrive. I thought a bit about the famous Mr. Rogers line about “look for the helpers”, and Matthew, Marina, and Mikey's team at their company Layer Aleph really were the equivalent of the helpers when it comes to the place where where technology meets the real world.
I’d first heard legend of their way of working in the days and weeks after the notoriously rough launch of Healthcare.gov (This was back when the federal government aspired to competency, inability to deliver was considered a scandal, and media would accurately describe something that didn’t function as a failure.) A small, scrappy, multifunctional team had been able to transform the culture of this hidebound segment of the federal government, and deliver a set of services that are saving American lives to this day. That story is detailed well in the book, but at the time, the conventional wisdom was that this was a catastrophe so impossibly complex, in a bureaucracy so hopelessly broken, that nobody could possibly fix it. And then they did. (With the help of a lot of brilliant and motivated colleagues.)
One of the most infuriating tropes that I see repeated in media is executives (usually from boring old companies) insisting that their employees don’t want to work hard. Media outlets dutifully repeat this pernicious lie, despite there being no evidence to back it up, and then cultural commentators either credulously amplify it, or actively take part in advancing the narrative as part of their agenda, even though they know it’s false. There is an apparently infinite attention appetite for commentators who troll for attention by saying how “kids these days” don’t want to work hard.
As has often been documented, the hoary chestnut of saying “nobody wants to work anymore” dates back decades, if not centuries, and it’s never been true in all those years of deletion. It is, firstly, a tactic that bosses use for negging workers in a vain attempt to try to drive down wages (and to successfully get media to blame people for their own underemployment), but it also serves as an effective demonstration of just how little society understand about what actually motivates people.
I’ve helped found six companies in my life, and been involved in the start of a handful of other startups and nonprofits, and literally every single one was full of people who love to work hard. The simple reason for that shared trait is that all of those teams were comprised of groups of people with a few key things in common:
If people have these things, and believe in what they’re doing together, they will joyfully work their asses off.
I keep a file called history.jsonl on my laptop. I didn't put it there. Claude Code did, logging every prompt I've sent since October. The other day I counted the lines: 3,976. Six months, almost four thousand requests, across a dozen projects and at least five programming languages. That's roughly 23 prompts per day if you average it, though averages lie, and I should know better than to trust them.
I wasn't looking for this file. I was looking for something else entirely, the way you find an old journal in a drawer when you're hunting for a screwdriver. But once I started reading, I couldn't stop. Not because the prompts were interesting on their own. Most of them are mundane. But the shape of them, the way they change from October to March, told a story I hadn't noticed while I was living it.
My first prompts average almost 300 characters. That's roughly two solid sentences, sometimes three. They're polite, contextual, and careful. "Given the database schema located in './packages/api/db/data/schema.sql', generate a mermaidjs diagram explaining the database entity structure and all relationships." I'm specifying file paths. I'm explaining what I want and why. I'm framing the task before delegating it.
Reading them now, they sound like emails to a new contractor. Here's the work, here's where to find things, here's what I need back. There's a formality to it, a hedging, that I recognize from every first week at a new job. You over-explain because you haven't calibrated trust yet. You don't know what the other party knows, so you fill the gaps preemptively.
I finally got the chance to drop by one of my favorite podcasts, The Vergecast, where David Pierce had me on to talk about the recent conversation about Apple's moves around video podcasts, as well as the much broader big-picture considerations around keeping podcasts open. We started with grounding the conversation in the idea that "Wherever you get your podcasts" is a radical statement.
The episode also starts with a wonderful look back at Apple's first half-century as they celebrate their 50 anniversary, courtesy of Jason Snell, whose Six Colors is one of my favorite tech sites, and whose annual survey of tech expert sentiment on Apple is indispensable. He's completely fluent in Apple's culture and history, and minces no words about their recent moral failures. Definitely worth the watch! I hope you'll check out the entire episode, and let me know what you think, and I'm really glad to get to continue conversations that start on my site and bring them to a broader audience.
If you liked this one, here are some related pieces from the archives that you might want to check out:
Yesterday, I had the chance to witness someone who's one of the most dedicated, competent advocates for privacy and digital rights bring that message to a whole new platform. It turns out, it's pretty delightful, especially in a moment when our civil liberties and rights online couldn't matter more!
Cindy Cohn, the executive director of the Electronic Frontier Foundation, has been a tireless fighter for protecting everyone's digital civil liberties, and I was lucky enough to get to tag along as she took the story of that work to The Daily Show yesterday. It was no surprise that the conversation was so fluent and insightful on the topic, but I think a lot of people in the audience didn't expect that it would be such a fun and even delightful conversation about a topic that is, too often, confusing or complicated or boring.
Six years ago, when I first joined the board of the EFF, I was already a believer in the core principles the organization stood for, but one of my biggest hopes was that the messages and mission of the entire team could just be brought to a larger audience. That couldn't have been more perfectly accomplished than seeing Cindy translate some topics that were fairly technical, or which involved fairly arcane legal concerns, and make them very accessible. And this work is vital because both the overreaching, authoritarian government, and the irresponsible, unaccountable forces of big tech are threatening our rights more than ever.
I gotta admit, it was pretty fun to watch Cindy hand Jon a "Let's Sue the Government!" t-shirt. You can get one just like his if you donate to EFF or become a member!
You must imagine Sam Altman holding a knife to Tim Berners-Lee's throat.
It's not a pleasant image. Sir Tim is, rightly, revered as the genial father of the World Wide Web. But, all the signs are pointing to the fact that we might be in endgame for "open" as we've known it on the Internet over the last few decades.
The open web is something extraordinary: anybody can use whatever tools they have, to create content following publicly documented specifications, published using completely free and open platforms, and then share that work with anyone, anywhere in the world, without asking for permission from anyone. Think about how radical that is.
Now, from content to code, communities to culture, we can see example after example of that open web under attack. Every single aspect of the radical architecture I just described is threatened, by those who have profited most from that exact system.
