Dare Obasanjo
Tech/product leader who reads and cites earnings call transcripts; compares guidance and revenue trajectories to explain divergent market reactions.
Accurate Context Beats Prompt Errors in Claude
Context7 is a good example of the difference between context engineering and prompt engineering. I had issues with Claude using outdated API information when vibe coding an app yesterday. Someone suggested asking it to use Context7 as the source of truth for the API. Same prompts, diffferent context and everything worked.
Claude + Context7 Enables Local Oura Data App, Ditching ChatGPT
After hooking up Context7 to Claude, it stopped being dumb about reading API docs. I finally built an app I’ve wanted for years to analyze my biometric data from Oura. I didn’t even need a hosted service because Claude pointed out...
Tech Layoffs Mirror Journalism's Billionaire-Driven Turmoil
I saw the Devil Wears Prada 2 and thought it was a really good sequel to the original story. The key plot point of how technology changes and layoffs were roiling the journalism industry amid the whims of billionaires felt a...
Spirit Airlines Collapses as Iran War Spikes Fuel
Spirit Airlines is the first major economic casualty of Trump’s war with Iran. Rising fuel prices derailed the company’s turnaround plan as it had projected for $2.20 per gallon but prices hit $4.50 a gallon in April. 17,000 employees are out...
Spotify's Verified Badge Distinguishes Humans, Not AI‑Free Music
To address the flood of AI-generated artists on the platform, Spotify is rolling out a “Verified by Spotify” badge to help listeners more easily identify authentic human artists. This will become increasingly commonplace across platforms. That said just because the artists...
AI‑Driven Workforce Demands Immediate Lock‑In Cost Management
Any company that truly believes AI agents will be a significant part of their workforce in the future should be working overtime on the lock-in problem. Both the CTO & CFO should be having sleepless nights about x% of their workforce...
AI Undermines Software Moats, Ecosystem Remains Competitive Edge
Evan Spiegel, CEO of Snap, argues that AI is forcing everyone to confront what they learned years ago at Snapchat; software isn’t a moat. While AI coding makes it easy for competitors to copy your features, they can’t copy an ecosystem...
FIRE Community’s Savings Obsession Mirrors Hoarding Disorder
I’m convinced that a bunch of people in the Financially Independent, Retire Early (FIRE) community suffer from a mental illness similar to hoarders. A rational behavior dialed up just a smidge too high that it’s now irrational and damaging to...
AI Churns Out Iranian Lego Diss Tracks Instantly
The AI-generated Lego diss tracks from the Iranian government coming out so quickly after news events is a bleak sales pitch for how quickly you can get work done with AI.
Maine Governor Vetoes Data Center Ban to Protect Jobs
The governor of Maine has vetoed a bill that would have banned datacenter construction in the state until November 2027. She said while she shares the concerns about the impact of data centers on electricity prices and the environment, the bill...
Claude's New Integrations Let AI Broker Cross‑app Deals
Claude can now connect to your account on AllTrails, Audible, Booking, Instacart, Intuit Credit Karma, Intuit TurboTax, Resy, Spotify, StubHub, Taskrabbit, Thumbtack, TripAdvisor, Uber, Uber Eats and Viator. While I use Claude at work I’ve preferred Gemini & ChatGPT for personal...
Hawley Urges GOP to Reject AI Money, Warns Populist Backlash
Senator Josh Hawley is encouraging Republicans to shun the $300M in lobbying money from the AI industry and instead regulate the industry to avoid the ire of their voters. AI is now viewed so negatively that I can see a Trump-like...
AI's PR Crisis: Negatives Outweigh Benefits, Urgent Rebranding Needed
AI will increasingly have a PR problem as the average person sees it as 1. ChatGPT, a slightly better Google. 2. That tech my boss is forcing me to use that barely works. 3. The rationale for layoffs and higher electricity bills according...
Turn Meeting Notes Into Polished Docs with AI
How my team used AI today: 1. We review doc in meeting and I give feedback. 2. I offer to edit/rewrite. 3. I feed Claude the meeting notes and ask to rewrite doc based on my feedback. 4. I review then share it out. 5. Team member likes it and...
AI Job‑Loss Narrative Disputed Amid Real Layoffs
“The narrative of AI destroying jobs is not going to help America. First of all it’s false. Of course with every technology and every single day that goes by, jobs of the past are changed.” - Jensen Huang, CEO of...
Trump's Anti‑trans
Caitlyn Jenner can no longer travel internationally as her passport marks gender as “male” following Trump’s anti-trans passport policies. — 'I never thought leopards would eat MY face,' sobs woman who voted for the Leopards Eating People's Faces Party.
Investors Question Altman's Conflict‑of‑Interest, IPO Reluctance
To go along with news of 3 senior execs leaving OpenAI is this story about why some of its investors are unhappy with Altman’s leadership. • He doesn’t have equity in OpenAI, so tries to get the company to invest or...
Amateur Filmmakers Outshine Hollywood in Epic Showdowns
Dr Doom versus the Council of Kangs. This actually looks better than the Streetfighter movie which is an indication of how much power is now in the hands of amateur filmmakers.
Google Joins Rush to Fill Pentagon AI Gap
There’s a rush to fill the space that Anthropic has vacated by not working with the Pentagon. There’s a time I would have been surprised by Google being part of this rush but that was so long ago. Now it’s just...
Uber Overspends AI Budget; Early Hype Soon Wanes
Uber has already exceeded its annual budget for AI tools due to internal usage of tools like Claude Code. We’re in a honeymoon period when it comes to AI agents which will end as companies figure out where it adds value...
Perplexity‑Snap $400M Deal Collapse Highlights Unrealistic Valuation
The deal where Perplexity would pay Snap $400M to add their search to Snapchat is dead. This deal never made any sense as there was no way Perplexity could afford this deal and they get very little out of it. I...
AI Pricing Shifts: Claude Downgraded, Subsidies Ending Fast
We are now in the first wave of AI’s enshitification cycle. Claude has gone from having a Ph. D in your pocket to a bumbling intern while flat fee billing for enterprise users will now become usage based. Everyone knew the...
Oracle Layoffs Spark Backlash Against AI Job Threats
Oracle laying off 30,000 people to pay for AI data centers for OpenAI was a tipping point in the mainstream hostility towards AI and the awareness of AI-driven layoffs. The idea that people simply going to patiently wait for AI...
AI Model Regression Mirrors iPhone Slowdown Before Upgrade
It’s been shocking to see Claude go from an AI model that seemed one upgrade away from taking over most of the routine tasks in my day job to not even being able to reliably download a webpage without lots...
CEOs Balk at CFO's AI Scapegoat for Layoffs
CEOs when the CFO suggests blaming the layoffs on AI instead of the economy or declining sales.
CS Must Prioritize Agent Oversight Over Babysitting AI
“Ultimately, AI-enabled system development requires Computer Science to be about agentic oversight and system orchestration.” - Maggie Johnson, head of Google .org The idea that computer science education should become learning how to babysit AI agents sounds extremely short sighted.
Anthropic Staff Hold Shares, Betting on Higher IPO Valuation
Anthropic gave employees the option to sell up to $6B in shares at a $350B valuation but fewer sold than expected. Anthropic employees are instead waiting for the IPO where they expect the valuation to go even higher. At $30B ARR and...
AI Hype vs Reality: Voice Mode Forgets Basics
This is a great illustration of the disconnect in perception of AI’s usefulness between people who use free chatbots and people using cutting edge models for work. ChatGPT’s voice mode can’t handle the basic task of remembering a number. It’s hard...
AI Turns Product Specs Into Live Prototypes Instantly
Had one of those AI native moments today. Someone sent out a document with a product proposal to review. Another person fed the document to an AI tool which built a prototype from the spec so we could discuss an...
Sensational Claims Question Altman's Trustworthiness, but Lack Substance
That the premise of this article is “we interviewed 100+ people to determine if Sam Altman is a liar and a sociopath” is wild. The animation of the image in the article is also quite unsettling. https://www.newyorker.com/magazine/2026/04/13/sam-altman-may-control-our-future-can-he-be-trusted?currentPage=all
AI Scans Slack, Formalizes Core Docs for Alignment
This talk with Anthropic’s head of growth validated two ideas I’d been considering trying out at work. 1. He has Claude scan Slack to find places where teams may be out of sync and doing overlapping or conflicting work. 2. Certain documents...
Twitter, Not Social Media, Is the Real Audience Killer
Nate Silver pens an essay about how social media is dead as a way to build an audience because Twitter is now a right wing cesspool where Catturd gets more engagement than the New York Times. Weird that it never occurs...
Kindness Is Crucial for Corporate Career Advancement
My friend @omarshahine recently switched roles as the VP of Microsoft Word and shared his farewell message to the team. His key takeaways struck a chord as they are the qualities of the best leaders I’ve worked with. I’ll also be...
AI Tools Now Boost Developer Productivity by 18%
I’m sure you’ve heard reports of the research study showing that open source developers using AI who thought they were more productive were actually -19% slower. That was in 2025. They reran the study earlier this year and developers are seeing...
Streaming's Financial Bubble Predicts AI Labor Debates
I remember during the strikes where actors and writers wanted more money, I pointed out that streaming was in a bubble and was already unsustainable without raising costs by paying the talent more. People were really upset with me for not...
AI Agents Will Price Token ROI Against Human Hires
The end game for AI agents is companies making decisions like do we give a product team $200K to hire another developer or an extra $150K in Claude credits? It will be similar math to hiring contractors versus full timers. The...
OpenAI, SpaceX Deals Echo Localized ZIRP Phenomenon
OpenAI buying a podcast for a few hundred million and SpaceX IPOing for a $2 trillion feels like a wierdly localized form of ZIRP. https://www.wired.com/story/openai-acquires-tbpn-buys-positive-news-coverage/
AI Flattens Hierarchies, Eliminating Traditional Middle Management
Jack Dorsey argues that AI enables companies to eliminate layers of middle management as they only exist to pass information back and forth upper levels to frontline workers. Basically AI has access to all of the data and communications at the...
AI-Native PMs: Expanding Scope with Intelligent Tools
Some thoughts on how the role of PMs has evolved with the rise of AI. Being an AI-native PM isn't just about using AI tools, it’s about leveraging AI to both deepen and broaden the scope of the role. https://dareobasanjo.medium.com/the-ai-native-pm-product-management-with-superpowers-49bd8a6574ee
AI Code Leaks Boost Demand for Software Security Jobs
Woke up to news of supply chain attacks on NPM and Claude Code’s source code leaking…again. It seems the only tech jobs that AI with any job security are going to be software security jobs. It’s only going to get...
AI Sparks Role Standoff Among Devs, Designers, PMs
Marc Andreessen argues AI has created a Mexican standoff between developers, designers & PMs. PMs think they can now design and write code with AI. Coders think they no longer need designers or PMs. Designers know they can do the job...
AI Streamlines Tool Guidance Updates, Slashing Hours of Work
Claude Code time savings of the day. Wrote a post at work giving guidance comparing various internal configurations of tools. A few commenters said the guidance was out of date as some tools had been updated. I asked Claude to 1. Review...
White‑collar Job Switches Hit Decade‑high Pay Cuts
More evidence that the job market for white collar workers is in a bad place. New data shows 40% of white-collar workers who switched jobs at the end of 2025 took pay cuts of more than 10%. This is the highest...
Dual Narratives, Hopeful Perseverance Shine in Stellar Film
This is a great movie. It tells two stories at once. The tale of the former molecular biologist, turned school teacher who wakes up on an interstellar spacecraft with amnesia and the backstory of how he got there. An amazing story...
Apple Opens Siri to Rivals, Ends OpenAI Exclusivity
Apple is abandoning its exclusive deal with OpenAI and will now allow other AI services to integrate with Siri and Apple Intelligence if their app is installed. It’s been a rough week for OpenAI.
AI Boosts Supply, but Demand Drives Layoffs
The problem with the question of why AI productivity gains lead to layoffs instead of simply producing more is that you need demand to go with supply. Consider Epic Games who just had layoffs due to Fortnite engagement dropping. Shipping 10...
Fans Force Studio to Redesign Live‑Action Character, Echoing Sonic
I’m convinced this may be the first time fans bully a movie studio into redesigning a live action character similar to what happened with Sonic the Hedgehog.
Copilot's Market Share Plummets as Rivals Rise
I thought Microsoft’s consumer version of Copilot was a flop but it seems the real concern is the business usage. Only 3.3% of Microsoft 365 customers have upgraded to paid versions of Copilot but that’s not the bad news. Recon Analytics...
AI-Native PMs Must
I have an essay on what it means to be an AI native PM which touches on the topics below related to PMs wearing multiple hats. I’m torn between scrapping it as we are overdosing on AI think pieces or sharing...
US Oil Shortage Fuels Iran’s War Funding
Thanks to the oil shortages caused by the war with Iran, the US is now forced to buy Iranian oil and that money is then used by Iran to fund its war with the United States. 5D chess.