From Founder to Chief of Staff: How Offline Runs on AI with David Shaner
In Part 1 of this conversation on Triangle Tweener Talks, we walked through how David built Offline over 13 years, three companies, multiple pivots, and a subscription model that finally worked.
In Part 2, we shift gears. This episode is about leverage. David breaks down how he went from running a ~34-person team to operating a multi-city business with ~2.5 people, not by cutting corners, but by rebuilding the company around AI-first systems, orchestration, and context-aware automation.
This is not “AI news.” This is how a founder is actually using AI day to day.
Highlights from Part 2
AI…
The skinny
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