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.
A Design System for a One-Person Company, Built in One Evening With Claude
Colors, type, spacing and a logo I finally stopped fiddling with, all in Figma, all turned into code, and live on the site the same night. Plus the font I had to give up.
A Logo, a Favicon, and My First Piece of Collateral — Built in Figma With Claude Driving
The AI-generated emblem was the brief, not the file. Rebuilding it properly taught me more about brand work than the generating did — and the first thing it went on was a golf sign.
I Set Up a CRM Before I Had a Pipeline. Here's Why Attio.
Three real relationships and no revenue isn't a pipeline. I built the system of record anyway — Attio, fed by Granola and Claude — because the first time you need a CRM is exactly when it's too late to set one up.