Startups Versus Incumbents

O’Reilly Media
O’Reilly MediaApr 7, 2026

Why It Matters

Understanding where AI automation can disrupt versus reinforce existing players guides investment decisions and strategic pivots for both legacy firms and emerging startups.

Key Takeaways

  • Incumbents excel when data already embedded in existing workflows.
  • Startups thrive in unstructured, untapped automation opportunities now.
  • AI agents automate messy human-centric tasks like legal review.
  • AI-native firms can outpace legacy competitors by two to five times.
  • New AI-driven agencies will lower costs and expand market reach.

Summary

The video examines how incumbents and startups compete in deploying AI agents across business workflows, arguing that the balance of power hinges on data availability and task structure.

Incumbents retain an edge when large volumes of workflow data already reside in their legacy systems; they can quickly layer automation and monetize existing processes. Conversely, startups find fertile ground in wholly new, unstructured domains—such as collaborative legal review, audit, and risk analysis—where no entrenched player exists.

The speaker cites examples like Harvey and other AI‑driven legal assistants, and predicts the rise of AI‑native firms—law, accounting, and advertising agencies built from scratch—that can deliver two‑to‑five‑fold productivity gains over traditional competitors.

These dynamics suggest a bifurcated market: incumbents must accelerate data integration to defend their turf, while investors should target startups that tackle messy, human‑centric work. The shift promises lower service costs, broader market access, and a redefinition of professional 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.
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