Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses.

What you’ll learn:

1. What actually happened with Meta’s $14 billion investment in Scale AI [10:27]

2. Why AI models still need human experts to improve, and how that relationship is evolving [28:18]

3. How AI models learn from experts building websites and debugging code [18:48]

4. The business lessons from building Uber Eats from zero to $20 billion [41:43]

5. Why most enterprise data is useless for AI models today [25:53]

6. Why urgent daily problems beat super-valuable occasional problems when building products [46:03]

7. How to think independently when building new products and businesses [48:19]

Brought to you by:

Merge—The fastest way to ship 220+ integrations

Figma Make—A prompt-to-code tool for making ideas real

Mercury—The art of simplified finances

Where to find Jason Droege:

• X: https://x.com/jdroege

• LinkedIn: https://www.linkedin.com/in/jasondroege/

Referenced:

• Travis Kalanick on X: https://x.com/travisk

• Scour: https://en.wikipedia.org/wiki/Scour_Inc.

• Scale: https://scale.com/

• Alexandr Wang on X: https://x.com/alexandr_wang

• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody

• Brendan Foody’s post on X about knowledge work changing: https://x.com/BrendanFoody/status/1970163503702188048

• MIT Finds 95% of GenAI Pilots Fail Because Companies Avoid Friction: https://www.forbes.com/sites/jasonsnyder/2025/08/26/mit-finds-95-of-genai-pilots-fail-because-companies-avoid-friction/

• Uber Eats: https://www.ubereats.com/

• Stephen Chau on X: https://x.com/thestephenchau

• a16z Podcast: https://a16z.com/podcasts/a16z-podcast/

• F1: The Movie: https://www.imdb.com/title/tt16311594/

• V03: https://v03ai.com/

• Careers at Scale: https://scale.com/careers

Recommended books:

• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152

• The Road Less Traveled: A New Psychology of Love, Traditional Values, and Spiritual Growth: https://www.amazon.com/Road-Less-Traveled-Timeless-Traditional/dp/0743243153/

• Good to Great: Why Some Companies Make the Leap . . . And Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996

• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:...