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Sign up for freeWill Larson, CTO of Imprint, explores how AI and shifting industry expectations are changing engineering management, career ladders, and the path from engineer to CTO.

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Finalist #13 in the Book Review Contest

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“AI SRE” is fast becoming a trending term fueled by flashy demos from vendors, but has an AI SRE ever really been on-call while engineers slept? Deepdive

Immigration, the welfare state, and Keynesian economics are all showing signs of strain.

When FLIPR and prediction markets disagree, which has the better case?

Plus Netanyahu’s long-term effort to make Democrats hate him and the problem with wealth taxes

The humanities; Data center crowd-out; Chinese local governments; AI and capitalism; How Japan builds; Phones bad; Chinese manufacturing; Rent control
Things aren’t looking great.

If there’s a blue wave, how far could it reach?

It doesn’t make a lot of sense to imitate an extreme outlier event.

A month’s worth of security breaches in a single day – will things get worse before they improve? Also: Anthropic accused of version control “rip off”, and more

It’s tough to say anything meaningful about the midterms at this point, but Democrats should think harder about their fundraising.

Level 2 - Value Investor

I’m way more online than I should be, and you probably are too.

Buyer, beware of omissions

Level 5- Sonic Autist

A movie review, plus some thoughts on dishonesty, belief, and human communication.

Listen now (86 mins) | The founder who helped over 50 startups hit $1M ARR shares his PULL framework for finding real product-market fit

What will be next to break?

It might be the most important issue right now, but I’m not history’s main character.

Who knows what piece of infrastructure might be attacked next.

Nobody in the tech industry wants to see them collapse, but the stock has dropped over 50% in the last six months, anyway

We may know a lot more, soon

In Michigan, Jocelyn Benson is polling well ahead of Abdul El-Sayed. Do gaps like that tend to shrink on Election Day?

In Response to Trump’s Tariffs, Canada Has Successfully Boosted non-US Trade to Record Highs—But it Remains Deeply Tied to America

Rouand and round we all go: a short deep dive into Anthropic’s revenue and its obligations

The case against cheap climate policy
![[Abridged] Foundations: The Fate of the S&P 500’s Worst Stocks, the Y2K Analogue, and Time for Small Caps?](https://substackcdn.com/image/fetch/$s_!z29k!,w_1200,h_675,c_fill,f_jpg,q_auto:good,fl_progressive:steep,g_auto/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc0936fe6-2716-4284-80e1-c3e833c5135d_2934x1650.png)
Predicting Long Positions for Performance Through the Next Bear Market

Your weekly listens from How I AI, part of the Lenny’s Podcast Network

6 honest lessons on finding time, setting priorities, and making a meaningful impact — even when life is already full

And so, here we are in the last days of the 2026 midterm campaign.

Trump’s increasingly erratic and corrupt behavior condemns Republican leaders who continue to support him.

🕊️ nothing alleviates the fellowing except flight

Plus, Heather Cox Richardson returns

Can billionaires buy the midterms?

The major labels made seven big mistakes—and are now paying the price
From the Burning Bush to ChatGPT

The unconventional approach to getting everything you want (and more)

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The 1850s are calling.

The state of the streaming wars.

Watch this week’s earnings reports to get some clues

I have 100 free tickets to give away for investing conference on November 3rd.

Brazil refuses to be bullied

As the midterms loom, he’s finally admitting the obvious

The Subscription Rate for Cassandra Unchained Will Remain Unchanged $49/Month and $479/Year

1. Do extremely hard things

To investors,