The Challenge
Mark Manson (author of The Subtle Art of Not Giving a F*ck) wanted to scale his coaching methodology. Traditional approaches—courses, books, one-on-one coaching—couldn’t provide the personalized, ongoing support his audience needed.
Could AI enable a new kind of coaching experience? One that’s more than a chatbot, but accessible at scale? Deep, personalized guidance—anytime, anywhere.
My Role
Head of Engineering. I architected the AI coaching system, built the technical team, and designed the evaluation framework for coaching quality. Designed and implemented a privacy-first data infrastructure for sensitive conversational data. Drove organizational transformation through the MTS (Member of Technical Staff) model and led technical hiring strategy—including Staff Engineer recruitment with competency-based frameworks.
The Approach
The hard problem in AI coaching isn’t generating plausible responses—it’s avoiding sycophancy. Most AI products learn to tell users what they want to hear. Coaching requires something harder: compassionate honesty.
Built on evidence-backed psychological frameworks, our key technical decisions included:
- 8-dimension evaluation rubric for AI coaching quality, with human annotation workflows
- Memory system that handles emotional statements appropriately—not just storing facts, but understanding context
- Non-sycophantic response generation that balances support with genuine challenge
Results
- $1.5M ARR in first three weeks
- 50,000+ active users
- 41% of users rate Purpose as “life-changing” when asked about its value