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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

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Oct 9, 2025

Guest

Jason Droege

Jason Droege, CEO of Scale AI and former Uber Eats leader, shares gripping insights from his journey in tech entrepreneurship. He discusses the implications of Meta’s $14B investment and why human experts remain crucial for AI development. Droege dives into the importance of understanding customer needs, revealing how Uber Eats was built on restaurant economics. He also emphasizes the balance between urgency and high-value problem-solving while highlighting lessons on hiring and maintaining a strong team culture in innovative environments.

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Episode notes

00:00 / 00:00

Scale's Independence Post Meta Deal

Scale remains an independent company after Meta's $14B investment and continues growing month over month.
Meta took non-voting stock and a few employees moved, but governance and data privacy remained unchanged.

00:00 / 00:00

Labeling Shifted To Expert-Led Work

As models improved, labeling shifted from generalist tasks to expert-driven, high-skill work requiring PhDs and professionals.
Scale adapted early and now most tasks require nuanced expert inputs like website building or medical explanations.

00:00 / 00:00

Hire Experts Through Referrals And Campus Programs

Recruit experts through referrals, campus outreach, and targeted sourcing to build a reliable contributor network.
Provide a strong contributor experience because experts refer peers when the work is engaging and well-paid.

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Early Career Lessons from Scour and Negotiation

06:05 • 4min

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Scale AI Today and the Meta Transaction

10:28 • 2min

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The Evolution to Expert Data Labeling

12:41 • 4min

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Sourcing and Retaining Expert Contributors

17:03 • 2min

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Reinforcement Learning, Environments, and Agent Training

18:49 • 3min

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Concrete Examples of Training Data and Annotations

22:04 • 1min

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Enterprise Applications: Healthcare Use Case

23:33 • 4min

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Why Human Judgment and Context Matter

27:06 • 1min

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How Long Will Humans Be in the Loop?

28:19 • 3min

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Evals: Establishing What 'Good' Looks Like

31:29 • 4min

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From Knowledge to Action: The Next Wave of Agents

35:25 • 2min

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Why Many Enterprise AI Pilots Stall

37:36 • 4min

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Customer Obsession and Ground Truth Research

41:52 • 5min

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Prioritizing Urgency Over Occasional High Value

47:07 • 1min

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Independent Thinking and Founder's Insight

48:31 • 3min

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Picking High-Value Business Models and Unit Economics

51:07 • 2min

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Why Uber Eats Was the Right Bet

53:22 • 4min

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Winning McDonald's and Scaling Partnerships

57:27 • 3min

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Gross Margins as a Quick Business Filter

01:00:24 • 4min

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Survival Before Winning: Risk and Longevity

01:04:49 • 4min

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Hiring for Team Fit Over Perfect Talent

01:08:59 • 3min

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Using AI as a Tutor and Document Summarizer

01:12:18 • 3min

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Scale's Work, Growth, and Hiring Needs

01:14:55 • 41sec

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Lightning Round: Books, Media, and Mottos

• Mentioned in 33 episodes

The Road Less Traveled

M. Scott Peck

In this book, M. Scott Peck uses his experience as a psychiatrist to guide readers through the challenges of life. He argues that life is inherently difficult and that spiritual growth and self-awareness can only be achieved by confronting and overcoming these difficulties. The book is divided into four parts, focusing on discipline, love, spiritual growth, and the concept of grace. Peck emphasizes the importance of discipline in delaying gratification, accepting responsibility, dedicating oneself to truth, and balancing conflicting factors. He also discusses the myths and realities of love and how it supports spiritual evolution. The book highlights that avoiding problems leads to decreased growth and increased suffering, while facing them can lead to greater self-knowledge and inner peace.

#17

• Mentioned in 276 episodes

Good to Great

Why Some Companies Make the Leap... and Others Don't

Jim Collins

In 'Good to Great,' Jim Collins and his research team investigate why some companies achieve long-term greatness while others do not. The book identifies key concepts such as Level 5 Leadership, the Hedgehog Concept, a Culture of Discipline, and the Flywheel Effect. These principles are derived from a comprehensive study comparing companies that made the leap to greatness with those that did not. The research highlights that greatness is not primarily a function of circumstance but rather a result of conscious choice and discipline. The book provides practical insights and case studies to help businesses and leaders understand and apply these principles to achieve sustained greatness.

• Mentioned in 404 episodes

Thinking, Fast and Slow

Daniel Kahneman

In this book, Daniel Kahneman takes readers on a tour of the mind, explaining how the two systems of thought shape our judgments and decisions. System 1 is fast, automatic, and emotional, while System 2 is slower, effortful, and logical. Kahneman discusses the impact of cognitive biases, the difficulties of predicting future happiness, and the effects of overconfidence on corporate strategies. He offers practical insights into how to guard against mental glitches and how to benefit from slow thinking in both personal and business life. The book also explores the distinction between the 'experiencing self' and the 'remembering self' and their roles in our perception of happiness.

#132

• Mentioned in 108 episodes

The selfish gene

Lalla Ward Richard Dawkins

Richard Dawkins

In 'The Selfish Gene', Richard Dawkins presents a gene-centred view of evolution, arguing that genes are the primary units of selection and that they behave selfishly to ensure their own replication. The book explains concepts such as kin selection, inclusive fitness, and the evolutionarily stable strategy, highlighting how these mechanisms can lead to altruistic behaviors in organisms. Dawkins emphasizes that the 'selfishness' of genes is a metaphorical concept, describing their evolutionary consequences rather than any intentional behavior. The book has been influential in shaping modern evolutionary thought and remains relevant today.

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

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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/

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Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation

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Where to find Jason Droege:

• X: https://x.com/jdroege

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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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

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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

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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/

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

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Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

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