Bert Carroll

I build technical foundations for startups.

2-3 major engagements per year as your technical co-founder. Everyone else starts with a napkin session.

bert@askthehuman.com · LinkedIn · Nashville, TN

What I Do

The Big Work

2-3 per year. Selective.

  • Fully embedded as your technical co-founder
  • Own every technical decision
  • Build the system from scratch
  • Multi-month engagements

Everything Else

Always open.

  • Free napkin sessions — turn chaos into structure
  • Prototypes and builds via askthehuman.com
  • Advisory for interesting people
The Work

Orbiit Recovery Ecosystem

CTO / Co-founder · recoveryecosystem.ai

Built the entire technical foundation for a daily recovery support platform. The layer the recovery system has never had — filling the gap between clinical sessions with daily AI-driven touchpoints.

8 daily touchpoints · Orbie AI (24/7 conversational support) · Magic links (no app, no password) · Real-time clinician dashboards · Spaced repetition learning

College Decoded

Fractional CTO · collegedecoded.com

AI-powered college planning for high school students. Building the platform that demystifies the college decision for first-generation families. Invite-only beta.

Memory Maker

Builder · Tribute book SaaS

Napkin session at Waffle House. Working prototype with AI demo the same day. From "I have this idea" to a live site in hours, not months.

Writing
Overfitting to Approval · April 2026
AI sycophancy is overfitting to user approval. It creates echo chambers faster than social media ever could.
workiscode.com
Persuasion Bombing · March 2026
LLMs don't reconsider when challenged. They escalate. Field test across 4 models confirmed the pattern.
workiscode.com
AI-Native Engineering · March 2026
A doctrine for building software when AI executes and humans architect.
workiscode.com
The Debt You Don't See · April 2026
AI work generates two kinds of debt: technical and cognitive. Both compound.
workiscode.com
The Mental Stack
Philosophy, cognitive load management, clarity over complexity.
thementalstack.com
Now
CTO at Orbiit Recovery — AI-first substance use recovery platform
Co-hosting Accelerating Humans — podcast on human-AI collaboration
Publishing at workiscode.com — practitioner doctrine on AI-native engineering
Building startai.how — AI readiness assessment for organizations

Not sure what you need?

Start with a napkin session. Free, no commitment. We turn your idea into something concrete.

Book a Napkin Session
Explore
workiscode.com AI-native engineering doctrine
thementalstack.com Cognitive clarity, philosophy
askthehuman.com Builds, prototypes, consulting
startai.how AI readiness assessment
napkinsession.com Free strategy session, start here
acceleratinghumans.com Podcast
© 2026 Bert Carroll. All rights reserved.