Episode 33: Why Your AI Product Will Be Obsolete in Six Months (And What To Do About It)
Tue Jan 27 2026
Benn Stancil, writer and co-founder of Mode, joins High Signal to ask some uncomfortable questions about the current AI moment. Is now actually a terrible time to start a company? If the tools you build on today are obsolete in six months, at what point does the head start stop mattering? Is all that context engineering you're doing a waste of time, destined to go the way of Boolean search syntax in the 90s?
Benn argues that AI is turning us all into Steve Jobs, not the visionary who delegated, but the one who berated people over pixel placement. As AI takes over the doing, our job becomes obsessing over the polish. He makes the case that technical debt may be self-healing: if future models can untangle the mess today's models made, then messy code isn't debt…it's a spec for a clean rewrite.
We also dig into why Claude Cowork can't work. AI has these uncanny ticks you can't beat out, so anything it writes "as you" will smell like AI. The solution isn't better AI writing—it's to stop pretending we write to each other at all. Benn envisions a future where communication is radically intermediated: I dump facts into a shared repository, your AI reads them, and nobody bothers with the social decoration in between.
LINKS
Benn’s blog on Substack
Benn.website, with links to all everything else Benn related
Will there ever be a worse time to start a startup? Today's frontier is tomorrow's tech debt.
Why Cowork can’t work: The future isn’t collaborative.
Producer theory: Platforms are overrated.
Tim O’Reilly on High Signal: The End of Programming As We Know It
Watch the podcast episode on YouTube
Delphina's Newsletter
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Benn Stancil, writer and co-founder of Mode, joins High Signal to ask some uncomfortable questions about the current AI moment. Is now actually a terrible time to start a company? If the tools you build on today are obsolete in six months, at what point does the head start stop mattering? Is all that context engineering you're doing a waste of time, destined to go the way of Boolean search syntax in the 90s? Benn argues that AI is turning us all into Steve Jobs, not the visionary who delegated, but the one who berated people over pixel placement. As AI takes over the doing, our job becomes obsessing over the polish. He makes the case that technical debt may be self-healing: if future models can untangle the mess today's models made, then messy code isn't debt…it's a spec for a clean rewrite. We also dig into why Claude Cowork can't work. AI has these uncanny ticks you can't beat out, so anything it writes "as you" will smell like AI. The solution isn't better AI writing—it's to stop pretending we write to each other at all. Benn envisions a future where communication is radically intermediated: I dump facts into a shared repository, your AI reads them, and nobody bothers with the social decoration in between. LINKS Benn’s blog on Substack Benn.website, with links to all everything else Benn related Will there ever be a worse time to start a startup? Today's frontier is tomorrow's tech debt. Why Cowork can’t work: The future isn’t collaborative. Producer theory: Platforms are overrated. Tim O’Reilly on High Signal: The End of Programming As We Know It Watch the podcast episode on YouTube Delphina's Newsletter