State Change

Take a look at your week and ask, what are you doing to study? What are you doing to build demand, distribute your expertise, and how much time you're spending shipping? Full essay: youtube.com/watch?v=INQe4zyZ…

Now, the outside game is uh really dealing with the public, right? youtube.com/watch?v=J-HHUPWs…

Give an AI work shift a bounded goal. Break the epic into research issues, then execute the resulting tasks in later waves. youtube.com/watch?v=oyrHCfvf…

Does the best AI planner also get all the execution spend? Toby’s counterargument: use frontier judgment for the plan and analysis, then route the work elsewhere—unless the provider locks it in. Ray Deck + Toby Oliver, 15 Sep 2026.

Toby describes AI marking his daughter’s past exam papers and generating questions on weak topics. Full conversation: youtube.com/watch?v=4FeOh-0R…

Toby’s idea: the chat conversation becomes the crossroads. Secure data, created functionality and recurring tasks become pieces coordinated by your AI, which can chop and change the most efficient or effective thing for the job.

The biggest leap in developer leverage is moving from steering AI agents in real time to conducting them asynchronously through hierarchical rule systems. pro.statechange.ai/c/weekly-…

Writing AI instructions as numbered legal clauses is the best way to fight context rot and maintain architectural control over complex projects. pro.statechange.ai/c/weekly-…

“The big UI opportunity in AI is bringing your experience inside the flow.” Bring a smaller product surface into ChatGPT or Claude, where the customer and agent work. Full essay: youtube.com/watch?v=5NRQWPrS…

“They don’t want another destination.” Customers want their agents to use your software in their own environment. Full essay: youtube.com/watch?v=5NRQWPrS…

“You want to provide a smaller surface area.” A little visual, then let the customer and their agent decide how to work with your system. Full essay: youtube.com/watch?v=5NRQWPrS…

“The thread that I saw was the balance sheet.” Ray and Toby follow Miro’s announced deal from valuation to idle cash and investor pressure. Full conversation: youtu.be/SuZLAoRr2-E

“VCs want you either to go crazy or die.” Toby on investor incentives when growth no longer supports the old multiples. Full conversation: youtu.be/SuZLAoRr2-E

“What do you think your valuation is?” Ray asks what Miro’s announced deal and Airtable’s sale mean for a smaller SaaS business still losing money. Full conversation: youtu.be/SuZLAoRr2-E

AI may restructure a market before it restructures the company inside it — AI-native entrants start from a lower interface and move value from vendor to customer. Full conversation: youtu.be/MZwIHkmcDmg

Someone who works with a lot of Fortune 500 CEOs says their most common question about AI isn't strategic — it's "when do I get to retire?" Full conversation: youtu.be/MZwIHkmcDmg

CEOs aren't just cutting costs — they're handing headcount to AI. The honest answer to "when do I get to retire?" turns out to be: reduce headcount, and let AI carry the load. Full conversation: youtu.be/MZwIHkmcDmg

Frontier AI models are becoming interchangeable gears in a larger machine — the practical move is choosing the right model-plus-harness fit per job, not loyalty to one model, since new frontier leaders keep displacing the last favorite. Full conversation: youtu.be/p6PijF6Vci8

“The token efficiency is much better — token cost seems to be lower because it's more efficient.” Full conversation: youtu.be/p6PijF6Vci8

“It's actually the thing that surprised me the most about it is how fast it is.” Full conversation: youtu.be/p6PijF6Vci8