Jason Droege

Lenny's Podcast: Product | Career | Growth/Oct 9, 2025/1h 24m

First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege

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 Why AI models still need human experts to improve, and how that relationship is evolving How AI models learn from experts building websites and debugging code The business lessons from building Uber Eats from zero to $20 billion Why most enterprise data is useless for AI models today Why urgent daily problems beat super-valuable occasional problems when building products How to think independently when building new products and businesses — Brought to you by: Merge—The fastest way to ship 220+ integrations: http://merge.dev/lenny Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/ Mercury—The art of simplified finances: https://mercury.com/ — Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation — Where to find Jason Droege: • X: https://x.com/jdroege • LinkedIn: https://www.linkedin.com/in/jasondroege/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jason Droege (06:01) Jason’s early career and lessons learned (10:27) The current state of Scale AI (12:37) The shift to expert data labeling (17:02) Challenges and strategies in finding experts (18:48) Reinforcement learning and AI environments (28:18) The future of AI and human involvement (31:21) The role of evals (35:25) What AI models will look like in the next few years (41:43) Building Uber Eats and understanding customer needs (48:19) The importance of independent thinking (50:45) Setting high standards for new businesses (53:03) Exploring and selecting business ideas (57:07) The McDonald’s story (01:00:13) The role of gross margins in business feasibility (01:04:49) Why Jason says, “Not losing is a precursor to winning” (01:09:12) Hiring and building teams (01:12:11) AI corner (01:14:47) Lightning round and final thoughts — 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. To hear more, visit www.lennysnewsletter.com

Jason Droege

CEO

Scale AI

Uber Eats

Benchmark

Invest Like the Best with Patrick O'Shaughnessy/Oct 25, 2022/1h 7m

Jason Droege - Building Uber Eats - [Invest Like the Best, EP.300]

My guest today is Jason Droege, a venture partner at Benchmark. Jason’s had a long entrepreneurial career, which most recently culminated in building and leading Uber Eats. He joined Uber in 2014 with a blank piece of paper to grow the business beyond ride sharing. Within six years, he found product market fit with food delivery, refined the service, and scaled Uber Eats to a global $20 billion GMV run rate. Our conversation pulls out the most important lessons learned during that period and how Jason now employs them in his role at Benchmark. Please enjoy this great conversation with Jason Droege. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:52] - [First question] - What it was like at a high level building Uber Eats [00:07:38] - How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it [00:10:17] - What he learned about selecting competitive frontiers and mistakes made while building Uber Eats [00:15:17] - Things that Uber Eats got most right that he’s proud of [00:18:16] - Constructive mistakes that taught him a lot from his time with Uber Eats [00:20:36] - What made India such a competitive environment [00:26:13] - What improved the most in his playbook for launching in a new city [00:27:14] - Defining what best means in this competitive sector [00:29:01] - Dealing with suppliers in different categories and finding an ideal balance [00:32:09] - When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace [00:36:12] - Defining what founder market fit is and being “fingertippy” [00:37:29] - His views on the relationships between leaders of businesses and their cultures [00:40:26] - Why Uber believed in him more than he did [00:41:40] - What he learned about marketing to suppliers specifically [00:45:18] - Differing views he has on the concept of failure [00:47:31] - Thoughts about ideas versus execution and the relative importance of the two [00:49:10] - Effectively measuring opportunity cost and using it in decision making [00:58:56] - The most interesting things he’s learned from his time as a partner at Benchmark [01:00:15] - The kindest thing anyone has ever done for him

CEO

Decoder with Nilay Patel/Aug 8, 2018/47m

Recode Decode: Uber Eats boss Jason Droege

If you enjoy Recode Decode, we think you'd also like the Eater Upsell. Here's a recent episode of the show: Jason Droege, the man in charge of Uber Eats, talks with Eater's Dan Geneen about how the service started, how it interfaces with restaurants, and what he sees as the future of the brand. Learn more about your ad choices. Visit podcastchoices.com/adchoices

CEO

Appearances (3)

First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege

Jason Droege - Building Uber Eats - [Invest Like the Best, EP.300]

Recode Decode: Uber Eats boss Jason Droege