Operator · Builder · Investor
Brett
Chereskin
I run operations at a fintech, build tools with AI, invest in military founders, and write about all of it. West Point grad. 12-year Army veteran. COO at dub.
12 Years
Army Aviator
COO
at dub
3 Funds
LP & Angel
West Point
Class of 2006
The Work
What I'm Building
Three lanes. One thesis: operators who build with AI and invest in people create outsized impact.
Running Operations
COO at dub. I run customer operations, finance, HR, and most G&A functions — many of them single-handedly, using AI to do the work of an entire back-office team.
Listen: Risk & Reason PodcastBuilding with AI
I build real tools with AI and write about what happens. This website, production workflows, tools for friends — shipped, not theorized.
Read the blogInvesting in Veterans
LP in Context Ventures and Stage 2 Capital. Angel investor. I back military founders and help portfolio companies with GTM and operations.
Learn more