Side Project Spotlight

In this episode, Alex Hillman, co-founder of Philadelphia's legendary coworking space Indy Hall, takes us through his journey building a sophisticated AI executive assistant using Claude Code. What started as a simple terminal experiment in October 2025 has evolved into a full production system that autonomously manages network diagnostics, email workflows, relationship tracking, and newsletter automation. Alex shares the technical architecture, real-world stories of AI-powered problem solving, cost insights, and his thoughtful approach to building trust with AI while maintaining strong ethical guardrails.

## Chapters

- 00:00 Coming Up...

- 02:01 Introductions

- 03:57 The Origins of PhillyCocoa and Indie Hall

- 06:12 The Evolution of AI and Personal Assistants

- 07:35 Building a Personal Assistant with Claude Code

- 10:26 The Architecture of the Personal Assistant

- 14:04 Creating a Web App Interface for the Assistant

- 16:10 Using Tailscale for Secure Access

- 19:01 Mitigating Risks with AI Autonomy

- 29:24 Backup Protocols and Data Management

- 31:23 Emergent Behavior in AI Systems

- 34:10 Flow State and Productivity in Programming

- 37:56 Understanding AI Behavior and User Education

- 39:45 Cost Management in AI Development

- 45:37 Building Trust with AI Systems

- 53:53 Navigating Trust in Skill Utilization

- 55:23 Technical Applications for Non-Developers

- 01:00:17 Innovative Personal and Business Management

- 01:09:03 Transforming Workflows with AI

- 01:12:56 Ethics and Responsibility in AI Usage

- 01:18:25 Community Building Through Meetups

- 01:21:55 Tag

## Highlights

**Architecture:** Claude Code headless via CLI with WebSocket communication, Docker on Hetzner VPS, Tailscale networking, hourly snapshots, git hooks for destructive commands, multi-layered security.

**Real Use Cases:**

- Network monitoring that diagnosed an overheating router fan from a screenshot

- Email sorted by "easiest to hardest" instead of chronological

- Date night tracking with restaurant and wine pairing suggestions

- Organized 51 wine bottles via photos into ASCII grid layout

- Newsletter reduced from 4 hours to 30 minutes while preserving human writing

**Costs:** $20/month plan lasted 20 minutes. Now at $200/month. One Thanksgiving week hit $1,500 in overages during heavy development.

**Philosophy:** "Modest YOLO" approach—autonomous but controlled. AI enhances human work, doesn't replace it. The system can modify itself: type "add a button," refresh, it works.

**Open Source:**

- **Kuato**: Session search for Claude Code

- **Smaug**: Twitter bookmark archiver with AI analysis

- **Andy Timeline**: Auto-generated weekly narrative of the AI's evolution

## Event

**Big Philly Meetup Mashup** - March 15, 2026

Hackathon for Philadelphia's tech and creative communities. Theme: "Good Neighbors." Sponsored by Supabase.

https://indyhall.org/goodneighbors/

## Links

**Alex Hillman**

YouTube: https://www.youtube.com/@AlexHillman | Website: https://dangerouslyawesome.com | GitHub: https://github.com/alexknowshtml

**Open Source Projects**

Kuato: https://github.com/alexknowshtml/kuato | Smaug: https://github.com/alexknowshtml/smaug | Andy Timeline: https://github.com/alexknowshtml/andy-timeline

**Tools & Resources**

Indy Hall: https://indyhall.org | Claude Code: https://claude.com/product/claude-code | OpenClaw: https://openclaw.ai | Brian Casel: https://www.youtube.com/@briancasel | Termius: https://termius.com | Point-Free: https://www.pointfree.co/the-way

**PhillyCocoa:** http://phillycocoa.org

Intro music: "When I Hit the Floor", © 2021 Lorne Behrman. Used with permission of the artist.