Old vs new software economy: VCs debate whether AI natives can ever scale

matt_slotnick · x · 2026-10-20

Investor Matt Slotnick and Kyle Poyar debated AI-native startups versus legacy software incumbents. Poyar argued the two paths have diverged so far that we may permanently have an old and a new software economy that look nothing alike, and that AI-native companies have zero idea how real-world F500 companies operate.

Slotnick countered that there is nuance in both directions: AI natives may look more like incumbents at scale, and while they don't understand legacy enterprises day to day, they already have products those companies can't get enough of — giving them a seat at the table to learn. What matters is being positioned to adapt quickly as the world changes.

Related event: Investors Debate Whether AI-Native and Legacy Software Economies Have Permanently Diverged(6 posts)→

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