Monday, January 19, 2026

ChatGPT ads 📱, Elon vs OpenAI ⚖️, building a social filesystem 👨‍💻

OpenAI plans to start testing ads for Free and Go tier users in the coming weeks. Plus, Pro, Business, and Enterprise users will not see ads ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ 

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Together With TLDR

TLDR 2026-01-19

Reach millions of tech professionals at scale (Sponsor)

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Big Tech & Startups

OpenAI's long-rumored introduction of ads to ChatGPT just became a whole lot more concrete (2 minute read)

OpenAI plans to start testing ads in the US for Free and Go tier users in the coming weeks. Plus, Pro, Business, and Enterprise users will not see ads. The Go tier is a new $8 per month subscription with access to GPT-5.2 Thinking. Ads will not influence the answers that ChatGPT provides and will always be separated and clearly labeled. Conversations will be kept private from advertisers. A screenshot of what the ads will look like is available in the article.
Musk Seeks Up to $134 Billion Damages From OpenAI, Microsoft (3 minute read)

Elon Musk wants OpenAI and Microsoft to pay him damages in the range of $79 billion to $134 billion as he claims OpenAI defrauded him by abandoning its nonprofit roots and partnering with Microsoft. The court filing says Musk is entitled to a chunk of OpenAI's current $500 billion valuation as he donated $38 million in seed money when he helped found the startup in 2015. Musk also plans to seek punitive damages and possibly an injunction. OpenAI claims the lawsuit is baseless and is aimed at harassment.
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Science & Futuristic Technology

Going Founder Mode On Cancer (52 minute read)

Sid Sijbrandij, founder of GitLab, got the news that he had cancer on November 18, 2022. He underwent a brutal care regimen that involved surgical removal of his tumorous vertebrae and rounds of radiation and chemotherapy so intense that he required four blood transfusions to stay alive. After his cancer resurfaced in 2024, he decided to go 'founder mode' on his cancer, assembling a team to navigate his care journey. This article details the story of how he took charge of his health.
How Human Should Your Humanoid Be? (11 minute read)

While the humanoid form factor is likely to stay due to its clear advantages, that doesn't mean that robots will still stay human. Boston Dynamics' Atlas is an interesting look at a very different vision of what a humanoid robot can and should be. Robots don't have to be limited to what evolution resulted in. They can be engineered to have capabilities that far exceed humans.
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Programming, Design & Data Science

AI agents stuck in pilot purgatory? Here's why (Sponsor)

Over 70% of orgs are using AI agents, but only 11% of agentic use cases made it to prod in 2025. In this webinar, Camunda's CTO joins automation experts to cover the proven controls that help AI agents progress. Secure your spot to learn how to move AI agents from pilot to prod.
A Social Filesystem (42 minute read)

Files represent personal creations, so they should live somewhere users control. File systems allow data to outlive the software used to create it. Other apps are able to open the same files to read or write data, and it's up to the users' choice on what app to use. This is analogous to how the AT protocol (the protocol behind Bluesky and other social apps) works.
ASCII characters are not pixels: a deep dive into ASCII rendering (42 minute read)

This article details how a developer created an image-to-ASCII renderer. The resulting renderer converts 3D models and still images into ASCII. The renderer is interactive, and you can move the 3D models around by dragging. The post is detailed and contains many interactive examples explaining the work.
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Miscellaneous

TLDR is hiring a Senior Software Engineer, Applied AI ($200k-$300k, Fully Remote)

We're hiring the first engineer on TLDR's new Applied AI team. You'll build production AI agents and design modular, composable Claude Skills to let non-technical teammates create their own AI workflows. Learn more.
Don't waste your back pressure (4 minute read)

Agents have improved over the last year due to structures that provide them with automated feedback and allow them to work on longer-horizon tasks. This back pressure allows agents to identify mistakes, and the feedback helps them align on tasks for much longer. Developers should think about how to build back pressure into their workflows. Afterwards, they can loop agents until they have stamped out all of the inconsistencies and issues.
America is slow-walking into a Polymarket disaster (6 minute read)

Prediction markets let people wager on basically anything. These sites have recently boomed in popularity and are creeping into the mainstream. They are transforming news into a form of gambling. It is unclear whether these sites are meaningful predictors of anything, but the markets are manipulable.

Quick Links

Say goodbye to that awkward meeting transcription bot (Sponsor)

Granola is AI that transcribes your meetings and enhances your notes - so you can give each call your full attention. The best part? There's no meeting bot. Try Granola free
Brex's AI Hail Mary — With CTO James Reggio (92 minute read)

This post discusses Brex's culture, how it facilitated an aggressive shift towards a culture of AI fluency, and how Brex modernized its tech stack and applied AI agents to streamline its business.
Does AI mean the demand on labor goes up? (2 minute read)

Increased productivity means there's more that you could be doing.
jQuery 4.0.0 (20 minute read)

jQuery 4.0.0 is the first major version release in almost 10 years and includes some breaking changes.
Tesla AI5 chip nears completion, Elon Musk teases 9-month development cadence (2 minute read)

Tesla plans to iterate rapidly, aiming for a nine-month design cycle.
Histomat of F/OSS: We should reclaim LLMs, not reject them (18 minute read)

Developers should define the rules LLMs operate under instead of rejecting and blocking them.
Bring Back Ops Pride (14 minute read)

Most companies are bad at ops, and this is becoming clear as AI adds more chaos to systems already defined by chaos.

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Thanks for reading,
Dan Ni & Stephen Flanders


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