Startups Versus Incumbents with Aaron Levie

O’Reilly Media
O’Reilly MediaJun 15, 2026

Why It Matters

The division shapes where investment and competition will concentrate: incumbents defend data-rich, embedded workflows while startups and AI-native firms can disrupt messy, human-centric services and capture new market share. That dynamic will accelerate cost reduction, service quality improvements, and industry consolidation in knowledge-intensive sectors.

Summary

Aaron Levie argues that incumbents will retain advantage where large amounts of workflow data already reside in existing systems and they can quickly adapt to monetize agentic AI. By contrast, startups have fertile ground in automating unstructured, collaborative work—legal review, audits, contract analysis—where incumbents are weak and professional services or legacy methods are the only alternatives. He highlights emerging AI-native service firms—law, accounting, advertising—that can discard legacy workflows to achieve multiple-fold productivity gains. These insurgents can scale into new markets, lower delivery costs, and offer higher-quality services.

Original Description

There will be opportunities for both incumbents and startups in the agentic era, but they won’t be the same, argues Box cofounder and CEO Aaron Levie in this clip from AI Codecon. An existing workflow where an incumbent has already staked a claim (and collected a “substantial amount of the data for that particular workflow in an existing system”)? The incumbent has a relatively good chance of success. But startups have the advantage in areas that haven’t yet been automated—the messy, collaborative human-based parts of work like legal review or audit and risk analysis that depend on unstructured data. Check out Aaron’s pitch for AI-native people-oriented firms. #shorts #ai #genai #startup
Follow O'Reilly on:

Comments

Want to join the conversation?

Loading comments...