Brett Chereskin
I’m the COO of dub, a venture-backed consumer fintech. I run operations at the edge of what AI can do — shipping internal tools that replace entire functions — and angel invest in the founders doing the same. Earlier: twelve years in the Army, West Point ’06.
Three lanes, concurrently.
- 01Operating. COO of dub, a venture-backed consumer fintech. Ops, finance, HR and G&A — run lean with AI tooling I build in-house.
- 02Practicing. I ship real AI systems in production at a regulated company. I write about what works, what breaks, and what I’ve quietly retired.
- 03Investing. Angel investor and LP. I back operators shipping with AI. Advisory work on ops, GTM, and AI adoption inside scaling companies.
Recent posts.
Commander's Intent for AI Agents
The Army taught me to give intent, not step-by-step orders, and trust the people closest to the problem. It turns out that is also the secret to getting great work out of AI.
AI SEO Is the New Visibility Game. Here's How I Picked a Tool For It.
People are asking AI instead of Googling. That quietly rewrites the rules of being found. Here's how I evaluated Profound versus Athena for work — and why we went with Athena.
How I Used Claude to Fight a $600 Insurance Denial — and Actually Filed a Regulator Complaint
A routine visit to a specialist turned into a billing mess and a denied claim. Most people give up at that point. AI is the reason I didn't — and why I filed a formal complaint with the state.