▶ 78:40 · $TRAJECTORY · Trajectory raises $15M (Conviction) for continual learning; 10x smaller models beat frontier, improve 1% daily

episode briefing

John Gruber, Kyle Kuzma, Brad Gerstner

2026-05-29 · 15 company · 10 thematic

sentiment

14 bull1 bear0 neu

speakers

brad gerstner

Founder and CEO of Altimeter Capital, a technology investment firm, and host of the BG2 podcast. Known for concentrated growth bets and widely-read public memos on big tech.

ron

Former DeepMind researcher and Windsurf (acquired by Google DeepMind) founder; left $2B acquisition proceeds to start Trajectory; building continual learning platform for AI agents with $15M from Conviction.

zayn mountcastle

CEO of Pico Grid, defense technology company building integration layer for autonomous military systems; raised $45M Series A from Bessemer; 7x production scaling; contracts with Pentagon and NATO.

jamie

CEO of Pace, AI operations platform for insurance industry; raised $46M Series B from Driving Capital/Emergence/Proven; 100% pilot-to-production rate; customers include Credential, WW, Convex, Palomar.

quote

“What we're interested in is building like building an agent that is 10 years of experience on the job... we have models that are 10 times smaller than the frontier models that are able to beat them. But also, that's not what we're most exc…”

—ron

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