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.
I Redesigned My Website With Claude — Brand, Logo, and Code in a Day
I built the first version of this site with Claude in February. Three months later I rebuilt it — same tool, new design capabilities, totally different result. A walk-through of what Opus 4.7 and the Claude Code desktop app actually changed, with before/after screenshots.
Rebuilding the Crypto Strategy: Opus 4.6 Shipped It. Opus 4.7 Fixed It.
A 9-sell AVAX trim cascade exposed what my weekend build was missing. Here's how a real backtest, a regime detector, and one honest critique session turned a shippable-but-flawed strategy into one that actually beats buy-and-hold.
I Built an AI-Powered Crypto Trading System in One Afternoon
I spent a Saturday afternoon connecting four AI data services into a single system that analyzes social sentiment, reads blockchain data, runs technical analysis, and executes real crypto trades on a paper account. No code. No API wrappers. Just Claude and a handful of MCP servers.