Saastr · 18 October 2026

Jason’s Takes on This Week’s 20VC x SaaStr: Pro Rata Fights, the First Real AI Price Drop, and Why $500M ARR Isn’t Safe Anymore

Jason Lemkin, GP @ SaaStr

Jason Calacanis distills ten key lessons from recent venture activity: pro rata disputes, AI model pricing breakthroughs, M&A patterns, and the widening gap between mega-scale B2B winners and struggling midmarket software companies fighting for strategic buyers.

Read the full post on Saastr ↗

Topics: Venture Capital & Startups · Enterprise Software · AI (Horizontal)

Published by Saastr · their site ↗

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