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Welcome back. I took some risks last week by injecting more of my voice and personality into the newsletter. Subsequent engagement numbers confirmed some of my fears. Paid subscribers can read the last story to learn more.

For everyone, this edition unpacks:

  • the race to secure the internet, featuring insights from Cloudflare, Palo Alto Networks, Figma, Trail of Bits, Stratechery,

  • the frozen housing market,

  • and a look back at my interview with Zillow CEO Jeremy Wacksman.

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The Rising Tide:

Internet Instability

Photo: Kirill Kudryavtsev/AFP via Getty Images

It’s bad.

If you read no further, know this: the internet is more exposed than ever; many experts are “freaking out”; and yes — AI is why.

What happened last week

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Several government, school and hospital websites across Europe and beyond were taken offline on Wednesday as organizations rushed to protect themselves from two critical security flaws in PHP, a programming language that powers a large share of the internet.

Cybersecurity agencies across the world warned that organizations unable to apply fixes in time should consider taking affected sites offline. PHP's developers said a set of new updates fixing two previously identified critical vulnerabilities was available.

— Reuters, October 21, 2026

But that was only part of the story.

“Several dozen” cyber incidents hit global corporations and governments in a span of two days, John Milinovich, a senior product manager at design software maker Figma, wrote in a widely cited X post.

“[I]n isolation, each [incident] would have been the worst to happen in an entire calendar year,” he said. “Every sector from government to education to big tech and banks is being massively affected, and people are starting to freak out.”

IYKYK

For those in cybersecurity who’ve been warning about AI hacking risks for years, the underlying problem came as no surprise.

AI is making it easier to find and exploit bugs that have always existed in software; it’s just that now, we’re all about to learn exactly how insecure the internet really is, 404 Media cofounder Jason Koebler observed.

❝

[I]f every piece of software is a door, AI makes it exceptionally easy to turn the knobs of every door to see if it’s unlocked, even on buildings that human beings had never really bothered to try to open.

What we are learning at an alarmingly fast pace is that not only are some of the locks easy to pick, in some cases the door is wide open or there’s a giant hole in the wall.

— Jason Koebler, 404 Media, Oct. 22, 2026

But shocks like this one will push everyone to do better, including banding together to tackle the problem, experts told Business Insider.

Brace yourselves

Things are going to get “a lot worse before they get better,” Jason Clinton, Anthropic’s deputy chief information security officer, wrote on X.

  • Case in point: The number of attempts to exploit the PHP vulnerabilities disclosed on Wednesday jumped from tens of thousands in the 45 minutes after the announcement to millions by that night, Cloudflare CEO Matthew Prince reported.

“I think we’re going to have a couple years where every single week it’s going to feel like the sky is falling,” Prince told Reuters in a separate interview.

Actions everyone should consider

Everyone — from senior leaders and boards, to ambitious side questers and workers — should decide what really needs to be online.

  • For example, more companies will likely take certain services, old forms, and webpages off the internet so they can’t be targeted, Dan Guido, CEO of the cybersecurity firm Trail of Bits, told The Atlantic’s Matteo Wong.

  • Removing unused browser extensions and other software that can access your data would also be prudent, he added.

  • And if you’ve been vibe coding: “congrats … you’re also the head of security now,” beehiiv CEO Tyler Denk warned.

For the C-suite and their advisers specifically:

  • “[E]nsure agentic deployments are well guardrailed,” Palo Alto Networks CEO Nikesh Arora suggested on X Sunday morning.

  • “Deploy a second set of eyes to watch your deployments for drift, compliance and verifiability,” he added.

The future of the web

Most people won’t really care or notice how the internet is run in the future. But builders should understand this: the promise of the old internet of openness — millions of nodes and the ability to connect to anyone — will never return, according to Stratechery’s Ben Thompson.

On a podcast Friday, he referenced Neal Stephenson’s “Snow Crash” to help make the analogy. The sci-fi novel (one of my favorites, actually) depicts a world of fully distributed, nation-like enclaves that are locked down, while everything in between is a hellscape, Thompson said.

“The internet is going to be little fortresses everywhere, patrolled in a very cyberpunk way, by these agents that are always on, always alert, doing battle, and hopefully it never breaks through and you don’t know about it.”

The Atlantic’s Matteo Wong agrees the internet will need new walls. But unlike Thompson, he leaves room for a better outcome: if we eventually find and fix the vulnerabilities, “the result could be a more open web, where anybody can use widely available AI tools to run security checks at any time and you’ll feel safer sharing your personal information again.”

For businesses and workers, the question is which side of the walls you’ll want to be on.

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Decoding:

The Frozen Housing Market

Homeowners “hugging” their cheap mortgages will keep the U.S. housing market frozen through next year, Goldman Sachs economists predict.

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More than 95% of American mortgage borrowers pay less than today’s market rate, and 65% pay at least 2 percentage points less, a legacy of the mass refinancing of 2020 and 2021, when rates hit record lows.

In a note published Monday, Goldman Sachs economists say that gap will keep the housing market stuck through 2027, with just 3.9 million existing-home sales, 26% below 2019 levels.

— Fortune, October 20, 2026

Where rates are

  • Mortgage rates eased to 7.32% last week from 7.4% the prior week. Last year at this time, the average was 6.19%.

  • Goldman expects rates to fall to 6.4% by the end of 2027. But even then, owners locked in at 3% have little reason to trade up.

The macro effect

  • Fewer sales mean fewer commissions for brokers, fewer origination fees for lenders, and less spending on services like movers, or goods like furniture and appliances.

  • Couples who can’t buy are delaying families too.

New relief?

President Donald Trump signed an executive order Thursday aimed at bringing down mortgage costs, but questions remain about how the rules would be implemented.

Strategy Talk:

Zillow CEO — Jeremy Wacksman

Macro Talk founder Hope King on stage with Zillow CEO Jeremy Wacksman at the HOPE Global Forum in Atlanta in December 2025. Watch our conversation here on YouTube.

As Zillow CEO Jeremy Wacksman told me last December, the counterintuitive part is that lower rates matter less for buyers than for sellers.

  • “Everyone just looks at mortgage rates and says, ‘Oh, when mortgage rates come down, the housing market will get more affordable.’ It’s not directly that…

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