Now — Mastra (Port Co)
Chief of Staff at Mastra, the leading TypeScript framework for building AI agents, backed by Spark Capital, Gradient VC, SV Angel and Basecase VC. My role centers on sales, GTM, and customer support/success.
Inception - Early Stage Investing
Generalist Investor
Network
Operators and GPs who diligence deals and open doors when it matters.
Ray Tonsing
Caffeinated Capital
Varun Gupta
Caffeinated Capital
Sumeet Gajri
Original Capital
Lan Xuezhao
Basis Set Ventures
Bobby Lo
Vurb
Ricky Horwitz
Exponential
Brendan Baker
Rackhouse VC
Armaan Ali
Seifdune
Marc Bhargava
General Catalyst
Mike Annunziata
Also Capital
Ellen Chisa
Boldstart Ventures
Evan Fisher
Portal VC
Brexton Pham
Cantor Fitzgerald
Ariana Thacker
MoldCo
Luke Girgis
Rolling Stone (AU)
TX Zhuo
Fika VC
and others
Companies
* = angel investment
Operator-Investor

GP, Operator-Investor
Now — Mastra (Port Co)
Chief of Staff at Mastra, the leading TypeScript framework for building AI agents, backed by Spark Capital, Gradient VC, SV Angel and Basecase VC. My role centers on sales, GTM, and customer support/success.
Before — Series (Employee #1)
Chief of Staff at Series, which builds tools for institutional allocators. I helped scale to our first $1B in AUM, ran all enterprise sales, and built the GTM organization. Backed by 776, Fin VC, Caffeinated Capital and Basis Set Ventures.
Before — Preside (Co-Founder)
Workflow automation for public safety and government, backed by Caffeinated Capital, Basecase VC, Banter Capital and Basis Set Ventures. We never found product-market fit — but I learned how to invest in the next generation of public-sector founders.
I specialize in taking companies from $0 to $10M+ in ARR, finding problem-market fit, and intentionally scaling an organization. I plan to share those learnings with the next generation of picks-and-shovels founders.
Founders
Reach out if you’re deep in-domain, don’t need hand-holding, and are raising before a lead is locked.
josh@picksandshovelsvc.com