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

Bolt-On or Built-In // AI-native services, scaling, and the people who make it work

Bolting AI on is easy. Building it in is the hard part. Bryan Takayama and Josh Redd talk through becoming an AI-native services company. They touch on how to scale beyond just adding people, how to think about workflows, and what they're actually looking for when they hire in the AI era.

Environment You Work In (How it Affects Your Work)

The environment you work in is never neutral. It's shaping how you think and what you produce, whether you notice or not. Bryan Takayama and Josh Redd chat about the importance of both your physical and digital workspace recorded, fittingly, just before Fable 5 was ripped from our hands a mere three days into its life. (Pour one out for Fable 5: June 9–12, 2026.)

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.