Fun Raising
This is the role-reversal episode where Mat steps out from behind the host mic and gets grilled by Ali Rohde about his own playbook. Mat invests at Harpoon Ventures (deep tech, $1M to $5M checks) and runs Black Flag, Harpoon's pre-accelerator that often writes the very first check into companies before they've even incorporated. He came up as a YC founder (Zestful, killed by COVID), pivoted into VC via Julian Shapiro, and treats VC itself like a product, building tools like VC Sheet and pitchrec.com [http://pitchrec.com] to make the fundraising process less opaque for first-time founders. He's bullish on cold email in a world where everyone else worships warm intros, sharing the story of how he raised his first check with an all-emoji email to Shrug Capital. He thinks pitch decks are quietly dying because firms like Harpoon now run every incoming deck through AI before a human ever opens it. And he's brutal about what he's actually looking for in the first meeting: not your idea (he's seen a dozen versions of it, including the ones you think are unique), but whether you have the energy and depth to go a thousand miles deep on this for the next decade. On closing, he lays out the most honest cap table framework I've heard in a while: roughly 60% of VCs are net zero on your company, 25 to 30% are net negative, and only 10% are net positive. The goal isn't to chase the positives, it's to avoid the negatives. He also breaks down a "wave approach" to building real FOMO without lying, and offers a counterintuitive post-raise warning: today's bigger mistake isn't spending too much, it's still acting frugal when you've raised real money and need to deploy it fast.
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