In this episode, Aydin sits down with Greg Shove, CEO of Section, to unpack how AI isn't just a productivity tool—it's a new cognitive layer for modern organizations. Greg shares how Section pivoted from executive education to AI enablement after a single eye-opening session with ChatGPT. He dives deep into what it really takes to embed AI into workflows, culture, and decision-making—and why “talking to AI” is now mandatory at his company. From building a company-wide second brain with Claude to simulating board meetings with GPT, Greg offers a masterclass in practical AI integration.
Timestamps:
1:35 – Greg’s background: from flameouts to $250M in exits
2:00 – Section’s pivot from exec ed to AI enablement
3:01 – The 6-month internal resistance to AI
4:50 – Why training isn’t enough: the real AI challenge is change management
6:07 – Why treating AI like regular software is a strategic mistake
8:26 – What successful AI deployments have in common
10:02 – Lessons from Shopify, Duolingo, and Fiverr on AI expectations
11:45 – The price of AI is too low—why that might change
14:03 – AI vs. analyst time: “an hour becomes a minute”
15:31 – Section’s 25% productivity gain with AI
18:58 – Measuring productivity impact without perfect data
21:24 – Clever metrics: output per headcount, OKRs, AI shoutouts
24:51 – Using Claude as a company “second brain”
26:11 – Greg’s AI desktop setup: Perplexity, GPT, Claude
27:43 – The Section Expert: maintaining company context for AI
29:27 – “Working with Greg” manual: how to humanize your AI input
31:00 – The difference between values and operating principles
34:42 – Roleplaying board members with AI before real board meetings
36:05 – Claude vs. ChatGPT vs. humans: who gave better board insights?
41:00 – AI for owner-operators: create your own board
42:26 – What Greg’s most excited about: how AI unlocks new opportunities
44:08 – Where to find Greg & Section + listener discount
Tools & Technologies Mentioned:
Claude (Anthropic): Used to build a company-wide second brain and simulate board member personas
GPT (OpenAI): Used as a daily thought partner and board advisor
Perplexity: A go-to AI for fast, accurate information lookups
Section Expert (Claude project): A centralized AI project workspace housing all of Section's key documents for brainstorming
ProfAI (Section’s product): An AI-powered coach designed to teach people how to use AI effectively
ChatGPT for Teams: Mentioned as a better, paid alternative to free-tier tools
Gemini Pro: Noted for its screen-sharing and future context-awareness potential
Copilot (Microsoft): One of several LLM tools tested during board simulations
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