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Vermilion Cliffs Ventures | Ashley Smith

Backing technical founders at the earliest stage with focus on GTM strategy from day 0.

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The Young Founder Experience

Our thoughts on being under 20 and building a startup

The Trail Continues…

Vermilion raises $25M for our second fund

VC Hot Takes, Vol. 1: AI, narrative, and the early bets nobody will defend out loud

We asked 12 VCs for their hottest takes right now

June 2026:Vermilion Cliffs Notes

Series A season, buying GitHub stars, and SF AI Infra After Dark

Raising Your Next Round: Why Every Venture Bet is a Seed Bet with Aaron Harris of Magid & Company

What's in a (round) name?

Why Open Source as GTM Is Having a Moment

Is it the right choice for AI Infra?

April 2026: Vermilion Cliffs Notes

Party rounds, portfolio news, and AI Infra After Dark

Party Rounds: What happens when the party’s over?

Nothing. No one is there to help cleanup.

Round names are meaningless right now.

Or what I get asked about everyday by LPs, founders, and VCs.

How the Internet Lost Its Humanity

The bots are winning.