Death by a Thousand Databases

Going All In on AI-Native Services — feat. Alex Wittenberg of airCFO

Few people have watched the AI shift from closer in than Alex Wittenberg — CEO of airCFO and an early fractional CFO for Anthropic. He joins Bryan Takayama and Josh Redd for a wide-ranging conversation on how software and services are racing toward the same middle, and the bigger question underneath it all: what running a company really means in an AI world. The AI CFO Newsletter [https://www.aircfo.com/the-ai-cfo]

We Threw Out the Script

Bryan Takayama and Josh Redd go off-script on what an AI-native operating system looks like, why human judgment is the moat AI can't copy, and where they land (very differently) on whether AI is good for humanity. Buckle up, and please keep both arms and legs inside the moving vehicle.

Thinking in Notion

Everyone praises Notion until they're staring at a blank page. Bryan Takayama and Josh Redd share the framework for thinking in Notion — a projection-and-collaboration matrix, the four spaces every workspace needs, and how to think in types so your system scales instead of sprawls.

Notion Goes Developer Mode

Notion launched its developer platform, and even seasoned users had to recalibrate what Notion is now. Josh and Bryan welcome their first-ever guest — Bayler Kelly, Notion State's Head of Engineering — to break down CLI, Workers, syncs, and webhooks, and Notion's San Francisco hackathon.

AI Is in the Org Chart Now

AI is your coworker now. Bryan Takayama and Josh Redd share how AI shows up in their daily work and what it means for org charts, change management, and the skills that still belong to humans.