David Byron Drake
Engineering Leader · Published Author · Former YC CTO
Silicon Valley veteran, former Y Combinator CTO, and startup CEO — I help leaders and organizations navigate AI with clarity, honesty, and a focus on lasting autonomy. I believe AI tools should expand human capability, not create dependency.
For 18 years, I've been writing about the intersection of ambition, technology, and modern life. My work has reached hundreds of thousands of readers and appeared in Sky News and The Huffington Post. With a background that bridges Theatre and Computer Science, I bring both performance and precision to my work — comfortable on stage, in front of a camera, or deep in a terminal.
I write on Medium, and my earlier work lives at randomdrake.com.
I'm also an avid home cook who finds stillness in the kitchen. I live in Oregon with my wife and daughter. Lover of good humans, strong coffee, and the outdoors. Lifelong learner. Former actor. Science nerd with a Commodore 64 tattoo.
Open to Opportunities
I'm looking for my next role — ideally where AI, engineering leadership, and real-world impact converge. I bring 18+ years of shipping software, leading teams, and building companies from zero to one. I've been a CTO at a Y Combinator startup, a startup CEO, and I build with AI every day. I'm at my best when I'm building something that matters with people who care.
Engineering Leadership
CTO, VP/Dir of Engineering, Staff+
AI & Product Strategy
Applied AI, LLMs, human-AI systems
Full-Stack Builder
Architecture through deployment
Skills & Expertise
Leadership
- Engineering Management
- Team Building & Hiring
- Performance Management
- Product Management
- Agile & Scrum
- Emotional Intelligence
Technical
- Artificial Intelligence & LLMs
- Python, TypeScript, Go
- React, Next.js, Node.js
- PostgreSQL, MySQL, SQLite
- AWS, Kubernetes, DevOps
- REST APIs & System Architecture
Strategic
- AI Strategy & Implementation
- SaaS Product Development
- Project Management
- Research & Data Analysis
- Technical Writing
- Startup Operations (Zero to One)
GitHub Dashboard
Real-time analytics across my open-source work — language breakdowns, commit activity, CI/CD pipeline runs, and Claude API integration metrics. A live window into how I build with human-AI collaboration.
Live
Commit Feed
Multi
Language Analytics
Claude
API Metrics
CI/CD
Pipeline Status
I Will Not Drink With You Today
366 Days of Stillness, Sobriety, and Presence
A daily reader grounded in Stoic philosophy and practical wisdom. Moving beyond the standard memoir, it offers 366 reflections designed to help anyone navigate the quiet work of sobriety. It serves as a steady companion for those seeking to reclaim their agency and build a meaningful life, one day at a time.
Speaking & Interviews
Available for podcasts, panels, and keynotes on AI strategy, engineering leadership, building calm systems, creative practice for technologists, intentional work, and sobriety.
Let's connect
david@randomdrake.com© 2026 David Byron Drake. All rights reserved.
Made with ♥ in Tigard, OR