Empowering Personal Software Development

The Good Stuff, with Pete and Andy - Episode 20: Wingman - your AI Control Tower!

Hosts: Pete and Andy (recorded at City Beach, Perth)

Episode Overview: Pete unveils his breakthrough AI agent orchestration system "Wingman" - a Mac Mini-based control center for managing multiple AI agents simultaneously. The discussion explores custom-built solutions versus SaaS subscriptions, testing AI models through games, and the emerging paradigm of humans as "control tower operators" for AI systems.

Opening & Context Setting (00:00-01:48)

• Andy returns from illness for episode 20
• Final beach recording before Pete's mysterious Atlantic adventure
• Reflecting on recent guest episode with Bethanne

The Wingman Revolution (01:48-25:00)

• Pete's Mac Mini experiment: giving AI agents their own dedicated computer environment
• Evolution from basic setup to sophisticated web-based control system
• Multiple agent orchestration: Goose and Claude Code working in parallel sessions
• Remote access from anywhere - phone, laptop, or desktop
• Obsidian integration for documentation and artifact storage
• API endpoints for automated session creation and workflows

Agent-to-Agent Workflows (20:00-25:00)

• Return-to-base protocol for session completion and handoffs
• Webhook systems enabling autonomous agent chains
• Vision of fully automated code review and development cycles
• Moving from human-centered to machine-centered processes

Custom Tools vs. SaaS Fatigue (25:00-40:00)

• Economics of $15/month software subscriptions adding up
• Pete's approach: "Fast fashion for software" - build exactly what you need
• YouTube reel generator case study: custom-built vs. existing solutions
• The open-source developer superpower now accessible via AI

Management-Style AI Interaction (40:00-50:00)

• Transition from "button-pushing" to strategic oversight
• Using specialized agent personalities (Grug Brain Developer for code reviews)
• Dueling agents: building features in parallel and choosing the best
• Planning and auditing as core human value-add

Gaming as AI Benchmarks (50:00-01:09:00)

• Settlers of Catan as model testing environment
• Game mechanics as proxy for enterprise negotiation and resource management
• Tabletop wargaming automation concepts
• Testing strategic thinking, negotiation, and long-term planning capabilities

The Control Tower Paradigm (01:09:00-01:13:00)

• Humans as air traffic controllers for AI agent fleets
• Multiplayer mode implications for teams
• Terminology evolution: logbooks, flight plans, control towers

Dedicated AI Environments: Running agents on isolated hardware eliminates privacy concerns while providing full system access and persistent operation.

Agent Orchestration Architecture: The future involves managing 1-100 agents simultaneously across different projects and functions, requiring sophisticated coordination systems.

Custom vs. Commercial Software: AI development capabilities are shifting the economics from subscription services to custom-built solutions tailored to specific workflows.

Human Role Evolution: The transition from direct execution to strategic oversight and agent management represents a fundamental shift in how knowledge work gets done.

"I don't have a good way of explaining how just fucking nice this is" - Pete on Wingman's seamless operation

"The data is in the computer. You were in the computer. Talk to it." - Pete on the future of AI interaction

"It's the same way that junior developers fuck stuff up... we just need to use the same processes" - Pete on managing AI agents

"Fast fashion for software" - Andy's description of rapid custom tool development

Looking Ahead: Pete's system represents a glimpse into the future of human-AI collaboration, where individuals can operate sophisticated agent networks from anywhere, fundamentally changing the nature of knowledge work and business operations.