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:
What actually happened with Meta’s $14 billion investment in Scale AI [10:27]
Why AI models still need human experts to improve, and how that relationship is evolving [28:18]
How AI models learn from experts building websites and debugging code [18:48]
The business lessons from building Uber Eats from zero to $20 billion [41:43]
Why most enterprise data is useless for AI models today [25:53]
Why urgent daily problems beat super-valuable occasional problems when building products [46:03]
How to think independently when building new products and businesses [48:19]
Also on Spotify and Apple Podcasts
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:
• 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 [email protected].
Lenny may be an investor in the companies discussed.
