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PodcastMay 15, 20262:09:14

#50 GPT-5.5 Cyber, Apple $250 Million Class Action, Anthropic x SpaceX, Webflow Pricing

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About This Episode

Join Samuel and Kabarza on this week's Command AI as they break down Apple's $250 million Siri lawsuit and OpenAI's secret GPT-5.5 Cyber model. The hosts also dive into Anthropic's massive Colossus supercomputer deal with SpaceX, the rollout of Claude's new Agent View, and the controversial paywalling of programmatic usage. Plus, hear their thoughts on Perplexity's Mac app, the mind-blowing 12-million token context window of Subquadratic AI, Webflow pricing changes, the debate of HTML over Markdown for AI outputs, and Lovable's stunning but templated aesthetic updates.

Talking Points

  • GPT-5.5 Cyber
  • Apple $250 million class action lawsuit
  • Anthropic purchase all Colossus supercomputer from SpaceX plus usage limits lifted
  • Claude paywall programatic usage of Claude
  • Claude Agents
  • Perplexity computer use on Mac
  • Subquadratic
  • Webflow pricing updates
  • The unreasonable effectiveness of HTML
  • Lovable aesthetics

Transcript

We are live. I wonder when you were going to join. How are you doing? I'm good. You're coming out my earphone now. Yes, I am doing wonderful. Thank you so much for asking. How has your week been without me? I was off gallivanting around a Portuguese volcanic island off the coast of Africa. It's basically a hiking hotspot and it feels like Jurassic Park when you're there. It was quite rainy, though. I saw the social posts, the Instagram stories, and the Snapchats. I'm a daily user of Snapchat to check in on what friends are up to.

What have you been building since I've been gone? Gosh, a lot. One of them is planning a trip to Croatia. I made a website for it to share with the boys so everybody knows what we have to pack, where we are going, and how the weather is going to be. It's quite nice to have it visual rather than sending markdown. They don't even read the big H1s, let alone the hashtags. If I send an MD file, they think it's code. I've also had a sponsor who gave me something to work with, building a drag and drop video tool that adds subtitles. I've been adding a lot of automations as well. We are in the golden age as entrepreneurs where we can do so much more ourselves rather than hiring a team. It is quite addictive because you build and immediately see the results.

This week we have OpenAI's new security model. Last week, they quietly announced a cyber security model called GPT 5.5 Cyber. It is a challenger that will not be available to the general public but will roll out to a select group of trusted cyber defenders to shore up critical cyber defenses. It's becoming a growing industry trend where frontier models are being branded too dangerous for mass release. Hackers are using current models and breaking tasks down into smaller pieces using open-weight models to disguise their actions. A security expert might be much more delicate in how they prompt their way around vulnerabilities.

Apple is to pay $250 million to settle a Siri class action lawsuit. We were sold iPhones on the premise of having Apple Intelligence, but we still haven't seen it, and features like Genmoji just never worked. Eligible devices like the iPhone 15 Pro and 15 Pro Max will get $25 to $95 as a rebate.

Anthropic has been busy. First, SpaceX and xAI signed a deal to use the entirety of their Colossus Supercomputer. Anthropic was previously constrained with compute, but they have now struck deals with Amazon, Google, and SpaceX. However, they've also instituted a massive downgrade for developers by paywalling programmatic usage. Anywhere outside of any Claude UI is where you need to start paying API usage. This is a kick in the teeth for developers building their own harnesses around Claude code. On the bright side, they did launch Claude Code Agent View. It allows you to monitor all the agents running on your machine, dipping in to see what needs attention across multiple projects without losing context.

Perplexity released a new Mac app that acts as a personal computer assistant. It has a gorgeous interface and contextual awareness, though there are still bugs with features like the Clicky agent. They've also paywalled some of the interactions where the assistant controls the browser, forcing you into a separate computer mode instead of keeping you in your workflow.

A new startup called Subquadratic AI claims to have built a model with a 12 million token context window. By calculating only the distances between words that matter—similar to how humans speed read—they are theoretically able to scale context infinitely and process tokens much faster. Early tests show it beating Opus 4.7 in certain benchmarks, though it's still awaiting third-party verification.

Webflow has updated their pricing plans. The CMS and Business plans have merged into a Premium plan for $25 a month. While this is a small price increase for previous CMS users, it adds features like form file uploads that used to require the more expensive Business plan. However, if you need high bandwidth, it will cost you significantly more.

There is a strong argument for using HTML instead of Markdown files when interacting with AI. HTML can convey much richer information, representing UI panels, SVGs, and interactive elements beautifully. While it might consume more tokens than Markdown, the visual clarity and ease of sharing an HTML document on platforms like Vercel make it highly effective for planning, design, and team communication.

Finally, Lovable introduced a massive aesthetic update that generates award-winning style websites with just one prompt. While the font pairings and subtle motion look amazing, the designs are starting to feel templated. It's an incredible baseline for businesses that just need a good website quickly, but it won't be putting custom designers out of a job anytime soon.