In this episode of Pirates Only I invited two of my Black Flag colleagues Andrew Couillard, our Program Director, and Matias Zorrilla, who leads first-look reviews, to pull back the curtain on how we choose and champion deep-tech founders.

In this mailbag-style Q&A we celebrate crossing 600+ applications since our April launch and preview our first cohort.

Andrew walks through the six-week curriculum, from “Raise the Flag” orientation to a literal pirate-ship dinner that cements our lifelong commitment.

Matias breaks down what makes an application pop: a hair-on-fire problem, a uniquely qualified team, and a deck that’s sharp, concise, and visually polished. We share the check sizes we write ($250k–$1 million from Harpoon) and the strategic firepower founders get in return: warm intros, government go-to-market guidance, and access to partners like Palantir.

Along the way we trade green- and red-flag founder traits, cold-email hacks, and the one question every entrepreneur should ask a VC in the fundraising process.

If you’re gearing up to fundraise, or just curious how Black Flag thinks, hit play and sail with us. See you on deck!