Invest Like the Best with Patrick O'Shaughnessy

Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

1572 snips
Jan 29, 2026
Gokul Rajaram, seasoned product builder and investor who led core product and ads work at Google, Facebook, Square, and DoorDash. He discusses how AI is reshaping product roles and the one thing he sees as future‑proof. He contrasts exposed legacy software with durable systems, explains the three ways ad businesses make money, and shares lessons from working with top tech founders.
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INSIGHT

Product Development Is Becoming Bottom-Up

  • Product teams must shift from prescriptive plans to bottom-up, hands-on prototyping as AI capabilities move the frontier every few months.
  • PMs become guardians of the why and owners of evaluation methods to judge non-deterministic model outputs.
ADVICE

Prioritize Human Judgment Over Output

  • Rely on human judgment to pick what to build and to evaluate AI-produced work because AI generates lots of low-value output.
  • Keep humans reviewing critical code, design, and decisions to avoid bugs and vulnerabilities.
ADVICE

Design AI Products Around Durable Workflows

  • Start AI products by targeting high-value, repeatable workflows that use custom data and replace paid human roles.
  • Ensure your product owns scarce assets, control points, hardware, essential workflows, or network effects to build durability.
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