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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#647: You Are Sweet, Loved, and Beautiful