Descriptions:
Andrew Wilkinson, entrepreneur and co-founder of Tiny — a holding company spanning 24+ businesses — joins Greg Isenberg to share an unusually candid look at how he’s deploying AI agents across his personal and professional life. Wilkinson describes becoming obsessed with Claude Code (which he calls ‘OpenClaw’) since December 2025, waking at 3–4 AM to work in terminal with multiple tabs open, and building a SaaS business he now runs almost entirely autonomously as a proof-of-concept before rolling the approach out across his operating companies.
The most detailed demo involves a vector database built on Pinecone for his family office, Folly Partners, which lets him query across 132 direct investments — $16M invested, now worth $36M — and get instant breakdowns of write-offs and performance trends. He built a parallel system for Tiny’s portfolio, where the sheer volume of financial and operational data from 24 companies is otherwise unmanageable for one person.
Practical tooling discussed includes Fireflies for meeting transcription, nightly cron jobs that pull transcripts via API and write them as markdown files into Obsidian, Pinecone for semantic search over business data, and various prompt engineering tricks. Wilkinson is candid about the frustrations — estimating he spends 50% of his time debugging and only 20% being genuinely productive — making this a grounded, real-world account of agentic workflows for operators and investors rather than a hype reel.
📺 Source: Greg Isenberg · Published May 04, 2026
🏷️ Format: Workflow Case Study
