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 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.
Where to Find David Shaner:
LinkedIn: https://www.linkedin.com/in/davidshaner/
Offline Media: https://www.letsgetoffline.com/
Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo
Timestamps
00:00–02:30 – Why Part 2 matters
02:30–06:00 – Phase 1: AI as a copywriting intern
06:00–10:00 – Phase 2: coding, Cursor, and the “hit by a bus” moment
10:00–13:00 – Why founders need to build something themselves
13:00–17:00 – Orchestration layers and why n8n won
17:00–21:00 – Why AI SDRs mostly don’t work yet
21:00–24:30 – Context windows, atomic steps, and agent design
24:30–27:30 – Debugging workflows like a human
27:30–31:30 – How Offline reduced headcount without losing velocity
31:30–36:00 – Self-service platforms for restaurants and events
36:00–39:30 – Cloud Code, skill files, and the “singularity” moment
39:30–44:00 – The Chief of Staff repo and what comes next
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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.
We couldn’t share posts like this without our amazing sponsors:
Gold Sponsors:
Balentine: https://www.balentine.com/triangle-en...
EisnerAmpner: https://www.eisneramper.com
Robinson Bradshaw: https://www.robinsonbradshaw.com
Silver Sponsors:
Automated Consulting Group: https://automated.co
Bank of America: https://business.bofa.com/en-us/conte...
2025 Sponsors:
Extensis HR: http://www.extensishr.com/
LinkedIn: https://www.linkedin.com/in/davidshaner/
Offline Media: https://www.letsgetoffline.com/
Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo
Timestamps
00:00–02:30 – Why Part 2 matters
02:30–06:00 – Phase 1: AI as a copywriting intern
06:00–10:00 – Phase 2: coding, Cursor, and the “hit by a bus” moment
10:00–13:00 – Why founders need to build something themselves
13:00–17:00 – Orchestration layers and why n8n won
17:00–21:00 – Why AI SDRs mostly don’t work yet
21:00–24:30 – Context windows, atomic steps, and agent design
24:30–27:30 – Debugging workflows like a human
27:30–31:30 – How Offline reduced headcount without losing velocity
31:30–36:00 – Self-service platforms for restaurants and events
36:00–39:30 – Cloud Code, skill files, and the “singularity” moment
39:30–44:00 – The Chief of Staff repo and what comes next
---
This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.
We couldn’t share posts like this without our amazing sponsors:
Gold Sponsors:
Balentine: https://www.balentine.com/triangle-en...
EisnerAmpner: https://www.eisneramper.com
Robinson Bradshaw: https://www.robinsonbradshaw.com
Silver Sponsors:
Automated Consulting Group: https://automated.co
Bank of America: https://business.bofa.com/en-us/conte...
2025 Sponsors:
Extensis HR: http://www.extensishr.com/
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Triangle Tweener Talks is sponsored by:
Triangle Tweener Talks is sponsored by:
- Atomic Object: https://atomicobject.com/
