
Unsupervised Learning
On Unsupervised Learning we probe the sharpest minds in AI in search for the truth about what’s real today, what will be real in the future and what it all means for businesses and the world. If you’re a builder, researcher or investor navigating the AI world, this podcast will help you deconstruct and understand the most important breakthroughs and see a clearer picture of reality. Follow this show and consider enabling notifications to stay up to date on our latest episodes.
Unsupervised Learning is a podcast by Redpoint Ventures, an early-stage venture capital fund that has invested in companies like Snowflake, Stripe, and Mistral.
Cohosted by Redpoint investors Jacob Effron, Patrick Chase, Jordan Segall and Erica Brescia.
Latest episodes

104 snips
Jun 17, 2025 • 55min
Ep 69: Co-Founder of Databricks & LMArena on Current Eval Limitations, Why China is Winning Open Source and Future of AI Infrastructure
Ion Stoica, co-founder of Databricks and Anyscale, and founder of LMArena, dives into the intricacies of AI model evaluation. He reveals the shortcomings of traditional metrics and discusses new dynamic systems for assessing AI models. Stoica highlights the competitive edge China has in open-source AI, urging the need for collaboration in the tech landscape. The conversation also touches on the importance of human involvement in evaluations and the ongoing challenges in AI infrastructure and optimization, reflecting on the future of data and AI in enterprises.

90 snips
Jun 4, 2025 • 44min
Ep 68: CEO of Mercor Brendan Foody on Evals Replacing Knowledge Work, AI x Hiring Today & the Future of Data Labeling
Brendan Foody, the co-founder and CEO of Mercor, leads a pioneering company at the forefront of AI-native labor markets. He discusses the evolving landscape of AI in talent evaluation, emphasizing how AI can enhance hiring practices through improved candidate assessments. Brendan also shares insights on the future of data labeling and the skills needed to thrive in an AI-driven job market. Addressing the demand for software engineers and navigating the complexities of fundraising in tech, he provides a fascinating look at integrating AI into recruitment.

146 snips
May 27, 2025 • 44min
Ep 67: Max Junestrand (CEO, Legora) on Differentiating and Pricing AI Apps & How the Legal Industry Will Evolve
Max Junestrand, Founder and CEO of Legora, shares insights from his journey building an innovative AI platform for the legal industry. He discusses how AI is revolutionizing legal processes, making them more efficient and accurate. Key topics include strategies for scaling in global markets and the challenges of pricing AI applications. Max also reflects on essential lessons learned about adapting product strategies and fostering a fast-paced work culture, while emphasizing the need for law firms to embrace AI to stay competitive.

590 snips
May 22, 2025 • 58min
Ep 66: Member of Technical Staff at Anthropic Sholto Douglas on Claude 4, Next Phase for AI Coding, and the Path to AI Coworkers
Sholto Douglas, a Member of Technical Staff at Anthropic, dives into the advancements of Claude 4 and its impressive coding capabilities. He discusses how AI agents are starting to transform research in fields like biology and robotics, emphasizing their role in automating white-collar jobs. Predictions include the timeline for original scientific contributions from AI. A fascinating look into the trust needed between AI models and human developers showcases the economic implications of integrating these agents into everyday workflows.

153 snips
May 14, 2025 • 1h 23min
Ep 65: Co-Authors of AI-2027 Daniel Kokotajlo and Thomas Larsen On Their Detailed AI Predictions for the Coming Years
In this engaging discussion, Daniel Kokotajlo, a former OpenAI researcher and AI alignment advocate, teams up with Thomas Larsen, co-author of the AI 2027 report. They dive into the urgent need for safe AI development, exploring the timeline of AI advancements, the growing tensions between the U.S. and China, and the critical risks of misaligned AI. The duo offers compelling predictions for 2027, emphasizes the importance of public awareness, and lays out essential policy recommendations to ensure a safer AI future.

420 snips
May 8, 2025 • 47min
Ep 64: GPT 4.1 Lead at OpenAI Michelle Pokrass: RFT Launch, How OpenAI Improves Its Models & the State of AI Agents Today
Michelle Pokrass, a key player in launching GPT-4.1 at OpenAI, delves into the intricacies of AI model development and evaluation. She discusses how user feedback fuels improvements and the evolving challenges in AI training. The conversation highlights the shift towards Reinforcement Fine-Tuning for personalized applications and the importance of balancing conversational abilities with problem-solving as we look towards future models. Her insights reflect a deep understanding of AI's potential and the organizational growth at OpenAI.

239 snips
Apr 29, 2025 • 51min
Ep 63: Khan Academy Founder/CEO on Salman Khan on Classrooms in 20 years, Rolling out to 1.4M Users & Sal’s Hopes for AI Education
When Khan Academy launched Khanmigo, Salman Khan thought they might reach 100k users by 2025. Today, they’re at 1.4 million. 🎧 Sal joined us on Unsupervised Learning to talk about AI's role in education— from the vantage point of someone deploying it at scale. As founder of Khan Academy, he’s overseen the rollout of AI tools to over a million teachers and students, giving him a front-row seat to what’s actually working in classrooms. (0:00) Intro(1:17) The Vision for Future Classrooms(4:28) Khan Academy's AI Initiatives(7:06) Proactive AI and Engagement(10:33) Teacher and Student Experiences(18:24) District-Level Adoption and Policy(25:56) Gamification and Engagement(27:36) Evaluating AI Models(31:03) Global Impact and Future Prospects(37:43) Challenges and Innovations in AI Education(44:19) Quickfire With your co-hosts: @jacobeffron - Partner at Redpoint, Former PM Flatiron Health @patrickachase - Partner at Redpoint, Former ML Engineer LinkedIn @ericabrescia - Former COO Github, Founder Bitnami (acq’d by VMWare) @jordan_segall - Partner at Redpoint

393 snips
Apr 15, 2025 • 51min
Ep 62: CEO of Cohere Aidan Gomez on Scaling Limits Emerging, AI Use-cases with PMF & Life After Transformers
Aidan Gomez, CEO of Cohere and co-author of the Transformers paper, shares insights on scaling AI for real-world applications. He discusses the importance of reasoning in custom AI models and how tailored solutions can outperform general models in enterprise settings. Aidan also highlights challenges in data integration and the significance of privacy in AI use-cases across sectors like finance and healthcare. He emphasizes the need for global collaboration and the evolving landscape of AI technologies, all while maintaining an optimistic view on AI's societal impacts.

140 snips
Apr 9, 2025 • 43min
Ep 61: Redpoint’s AI Investors Break Down What Separates Enduring AI Companies from the Hype
Scott Raney and Alex Bard, partners at Redpoint, share their sharp insights on the AI investment landscape. They discuss the strategic imperatives for successful AI companies and unveil the critical distinction between enduring firms and fleeting trends. The duo emphasizes the importance of a balance between domain expertise and AI knowledge within founding teams. They also explore the challenges faced by startups, the paradox of first mover advantages, and what truly drives sustainable growth in the rapidly evolving AI sector.

468 snips
Mar 28, 2025 • 1h 2min
Ep 60: Swyx and Alessio (Latent Space) on What has PMF Today, Google is Cooking & GPT Wrappers are Winning
Join Swyx, an AI podcaster and expert in developer tools, along with Alessio Fanelli, an investor backing innovative AI teams. They discuss the surprising shifts in AI over the past year, including the rise of GPT wrappers and open source model adoption challenges. Insights on Google’s strategic momentum, emerging AI applications, and market trends are shared, alongside a candid exploration of over-hyped and under-hyped trends. The duo also delves into the importance of product-market fit and the complex landscape of AI infrastructure and security.