Jason Droege

CEO at Scale AI

CEO of Scale AI since taking over from Alex Wang after the Meta deal, previously launched and led Uber Eats from idea to multi-billion dollar business that saved Uber during the pandemic, co-founded Scour with Travis Kalanick, known for building new businesses within large organizations and navigating high-stakes negotiations.

The Visionary The Operator

Dimension Profile

Strategic Vision 75%

Execution & Craft 65%

Data & Experimentation 50%

Growth & Distribution 50%

Team & Leadership 55%

User Empathy & Research 35%

Key Themes

AI model training evolution from simple to expert tasks models moving from knowing things to doing things entrepreneurial insight as competitive advantage building new businesses within existing companies everything is negotiable in business AI deployment requires digging up every road

Episode Summary

Jason Droege shares lessons from launching Uber Eats and now leading Scale AI, explaining how AI model training has evolved from simple short-story comparisons to expert-level tasks requiring PhDs and hours of work. He draws on his early experience co-founding Scour with Travis Kalanick to articulate the lesson that everything in business is negotiable, and warns that AI enterprise deployment is like laying broadband — the headlines say one thing but someone still has to dig up every road.

Leadership Principles

→ In business and startups, everything is negotiable — there is no way to do things, there is just the way you can negotiate your way through the world
→ From an entrepreneurship standpoint, it truly is about what insight do you have and why in a world of a million entrepreneurs are you in the position to have an insight others do not
→ AI deployment is like laying broadband — headlines tell one story but on the ground, someone's got to dig up every road, it takes 6 to 12 months to get truly robust

Notable Quotes

"In business and in startups, everything's negotiable. There is no way to do things. There is just the way that you can negotiate your way through the world."
— On the lesson from co-founding Scour with Travis Kalanick at age 19

"Like with any of these major tech revolutions, headlines tell one story and then on the ground, laying broadband means you need to dig up every single road in America. Someone's got to dig up the road."
— On why AI enterprise deployment takes longer than headlines suggest

"18 months ago, you would get a short story and it would say, 'Is this short story better than this short story?' Now one task is building an entire website by one of the world's best web developers. These tasks now take hours and require PhDs."
— On how AI training data has evolved from simple comparisons to expert-level tasks

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