Bozena Pajak, VP of Learning at Duolingo, joins High Signal to discuss the evolution of AI at Duolingo: from personalized difficulty models to the current generative frontier where AI characters provide low-stakes and high impact conversational practice. We discuss the role of AI in overcoming one of the biggest hurdles in language acquisition, speaking anxiety. We also talk about how Bozena's team leverages agentic workflows to scale content and why the next wave of personalization involves shifting from difficulty levels to "thematic lenses" tailored to specific user interests.

LINKS

• Bozena on LinkedIn
  
• The original AI: how your brain tracks language patterns, a duolingo blog post
  
• How Duolingo uses AI to create lessons faster, a duolingo blog post
  
• duolingo is hiring a Learning Scientist (Efficacy Research), a Director of Learning Design (Language Learning), and a Director of Learning Design (Immersive Language Learning)
  
• High Signal podcast
  
• Watch the podcast episode on YouTube
  
• Delphina's Newsletter

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

Nicholas Moy, former Head of Research at Windsurf & now at Google DeepMind, joins High Signal to discuss the shift from "co-driving" to a truly "agentic" era of development. We discuss Windsurf's journey from early prototypes that struggled with compounding errors to the successful launch of their agentic coding product. Nick explains that building a startup in the current climate requires a strategy of "disrupting yourself" to avoid the innovator’s dilemma; companies must be ready to pivot as soon as a new frontier model makes previously impossible features viable. He argues that traditional technical moats are increasingly fragile, and true defensibility now comes from real-world usage data, brand reputation, and a deep intuition for what users need at the frontier of these capabilities.

LINKS

• Nicholas Moy on LinkedIn
• Introducing Google Antigravity, a New Era in AI-Assisted Software Development
• “A Flash of Deflation - Gemini 3 Flash represents a step function increase in model deflation : a gauntlet thrown” by Thomas Tunguz
• Tomasz Tunguz on Why a Trillion Dollars of Market Cap Is Up for Grabs (and How AI Teams Will Win It)
• High Signal podcast
• Watch the podcast episode on YouTube
• Delphina's Newsletter