From Founder to Chief of Staff: How Offline Runs on AI with David Shaner
Context windows, orchestration layers, and building agents that don’t get stupid
Refresher: David’s Backstory
David Shaner is the Founder and CEO of Offline, his senior project at NC State in 2012 that, thirteen years later, is a profitable, multi-city subscription business serving thousands of diners and hundreds of restaurants.
Get caught up with → Part 1
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Listen/Watch Our Interview:
Make sure to catch up with Part 1 if you missed it!
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 adoption started as a “copywriting intern,” not a silver bullet
The biggest fork: people who learned how to talk to models vs. people who gave up
The real unlock came when David built his first full-stack app himself
Tools like Cursor and Cloud Code collapsed the barrier between idea and execution
Offline stopped adding features to a monolith, and started building around it
n8n became the orchestration layer that glued everything together
Most business problems don’t need apps, they need glue code
AI SDRs fail today because context is fragmented and CRMs are a mess
The right approach is decomposing SDR work into atomic steps
Context windows are the real constraint, not intelligence
David now runs a personal “Chief of Staff” GitHub repo with 70–80 skills
The company itself is slowly becoming a file system agents can read and write from
If you’re thinking about automation, agents, or headcount, this one will change how you think about all three.
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📌 What’s Next
Next on Triangle Tweener Talks, we’ll continue spotlighting founders who’ve built real companies in the Triangle, digging into the decisions that shaped their journeys, the tradeoffs behind growth, and what they’re building next.
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