Unsupervised Learning Podcast

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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.

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Recent Hosts, Guests & Topics

Here's a quick summary of the last 5 episodes on Unsupervised Learning.

Hosts

Jacob Effron Patrick Chase Erica Brescia Jordan Segall

Previous Guests

Brendan Foody
Brendan Foody is the co-founder and CEO of Mercor, a company building infrastructure for AI-native labor markets, focusing on data labeling, evaluating candidates, and performance-driven hiring.
Max Junestrand
Max Junestrand is the founder and CEO of Legora, a rapidly growing legal AI platform and a portfolio company of Redpoint Ventures. He has led the company's journey through product development, scaling, and market penetration, focusing on how AI can transform legal processes and the legal industry.
Sholto Douglas
Sholto Douglas is a Member of Technical Staff at Anthropic, a leading AI research and deployment company. His work focuses on advancing AI models, particularly in the areas of AI coding, model capabilities, and the development of reliable AI agents. Douglas contributes to research on how AI can accelerate scientific discovery and improve real-world applications across various fields such as biology and robotics.
Daniel Kokotajlo
Daniel Kokotajlo is a former researcher at OpenAI, where he focused on artificial intelligence alignment. He is currently dedicated to his nonprofit, AI Futures, which aims to address the challenges of unaligned AI. Daniel has been recognized as one of TIME's 100 most influential people in AI, highlighting his significant contributions to the field.
Thomas Larsen
Thomas Larsen is a co-author of the AI 2027 report, which discusses the future of artificial intelligence and its implications. He has been involved in research and policy discussions surrounding AI development and safety, contributing to the understanding of potential risks and the need for aligned AI systems.
Michelle Pokrass
Michelle Pokrass is a leading figure at OpenAI, where she heads post-training initiatives. She played a pivotal role in the development and launch of GPT-4.1 and is involved in the upcoming RFT offering. With a focus on improving AI models, she emphasizes the importance of instruction-following and long context in AI development. Her work includes evaluating user feedback and addressing challenges in model training, making her a key contributor to advancements in AI technology.

Topics Discussed

AI in talent evaluation data labeling foundation models multimodal AI AI regulations future of skills AI hiring AI in legal industry AI product scaling Legal AI platforms AI pricing models Foundational models Legal industry evolution AI in complex industries AI coding AI agents model progress AI research biological breakthroughs robotics AI reliability model creativity AI societal impact AI 2027 report unaligned AI AI predictions policy implications AI safety AI alignment public awareness AI development timeline GPT-4.1 OpenAI model training instruction-following long context AI startups fine-tuning multimodal capabilities data efficiency

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Episodes

Here's the recent few episodes on Unsupervised Learning.

0:00 44:03

Ep 68: CEO of Mercor Brendan Foody on Evals Replacing Knowledge Work, AI x Hiring Today & the Future of Data Labeling

Hosts
Jacob Effron Patrick Chase Erica Brescia Jordan Segall
Guests
Brendan Foody
Keywords
AI in talent evaluation data labeling foundation models multimodal AI AI regulations future of skills AI hiring

Brendan Foody is the co-founder and CEO of Mercor, a company building the infrastructure for AI-native labor markets. Mercor’s platform is already used by top AI labs to label data, evaluate human and AI candidates, and make performance-driven hiring decisions. 

 

They’re operating at the intersection of recruiting, evals, and foundation model development—helping companies shift from intuition to measurable prediction. Brendan and his team recently raised $100M and are working with some of the most advanced players in the AI ecosystem today.

 

(0:00) Intro

(1:17) State of AI in Talent Evaluation

(1:54) Improvements in AI Models

(4:07) Mercor Background and Mission

(5:09) AI Use Cases in Hiring

(13:43) Data Labeling Landscape

(16:48) Expanding Beyond Coding

(18:39) Company Vision and Market Strategy

(21:11) Meeting with xAI

(23:47) Does Mercor Use Their Own Product?

(25:41) Exploring Multimodal Capabilities

(28:03) Skills for the Future: Embracing AI

(29:29) The Demand for Software Engineers

(34:55) Foundation Model Landscape

(38:42) AI Regulations

(39:57) 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

0:00 44:09

Ep 67: Max Junestrand (CEO, Legora) on Differentiating and Pricing AI Apps & How the Legal Industry Will Evolve

Hosts
Jacob Effron Patrick Chase Erica Brescia Jordan Segall
Guests
Max Junestrand
Keywords
AI in legal industry AI product scaling Legal AI platforms AI pricing models Foundational models Legal industry evolution AI in complex industries

Jacob and Logan sit down with Max Junestrand, founder and CEO of Legora - a rapidly growing legal AI platform (and Redpoint portfolio company). After announcing their Series B last week, Max joined the show to discuss why law is uniquely suited for AI, what it takes to scale an enterprise-ready product across global markets, and a few crazy moments from Legora’s journey so far. They dig into product strategy, lessons on evolving alongside foundational models, and how AI is reshaping the future of law firms. Whether you're building in AI or just curious how it’s being applied in complex industries, this one’s packed with practical insights.

 

(0:00) Intro

(1:30) The Evolution of AI in Law

(2:43) AI's Impact on Legal Processes

(8:28) Advantages Over Other Players in the AI Law Space

(12:19) Challenges in Educating Users

(17:28) The Hardest Part of Building Legora

(18:46) Pricing Models and Cost Management

(25:42) YC Experience and Commercial Focus

(28:11) Being Patient When Releasing Products

(30:58) Maintaining a Fast-Paced Work Culture

(33:24) Rapid Growth and Market Penetration

(36:59) 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

0:00 57:45

Ep 66: Member of Technical Staff at Anthropic Sholto Douglas on Claude 4, Next Phase for AI Coding, and the Path to AI Coworkers

Hosts
Jacob Effron Patrick Chase Erica Brescia Jordan Segall
Guests
Sholto Douglas
Keywords
AI coding AI agents model progress AI research biological breakthroughs robotics AI reliability model creativity AI societal impact

Sholto Douglas, a Member of Technical Staff at Anthropic, joined Unsupervised Learning to break down why coding is the clearest early signal of model progress, how AI agents are already accelerating research, and what it’ll take to unlock real-world breakthroughs in fields like biology and robotics.

 

(0:00) Intro
(0:48) Claude 4
(1:30) Capabilities and Improvements
(2:29) Practical Applications and Advice
(3:04) Future of AI in Coding
(4:38) Managing Multiple AI Models
(11:20) The Barrier to Agents is Reliability
(16:35) Agents Conducting Research
(19:54) Impact of Models on World GDP
(25:14) Most Important Metrics in Model Improvement
(29:53) Stories of Model Creativity
(32:45) How Often Will New Models Be Shipped in the Future?
(39:51) Day-to-Day Work of AI Researchers
(46:46) The Future of AI and Society
(51:26) 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

0:00 1:23:27

Ep 65: Co-Authors of AI-2027 Daniel Kokotajlo and Thomas Larsen On Their Detailed AI Predictions for the Coming Years

Hosts
Jacob Effron Patrick Chase Jordan Segall Erica Brescia
Guests
Daniel Kokotajlo Thomas Larsen
Keywords
AI 2027 report unaligned AI AI predictions policy implications AI safety AI alignment public awareness AI development timeline

The recent AI 2027 report sparked widespread discussion with its stark warnings about the near-term risks of unaligned AI.

Authors @Daniel Kokotajlo (former OpenAI researcher now focused full-time on alignment through his nonprofit, @AI Futures, and one of TIME’s 100 most influential people in AI) and @Thomas Larsen joined the show to unpack their findings.

We talk through the key takeaways from the report, its policy implications, and what they believe it will take to build safer, more aligned models.

 

(0:00) Intro
(1:15) Overview of AI 2027
(2:32) AI Development Timeline
(4:10) Race and Slowdown Branches
(12:52) US vs China
(18:09) Potential AI Misalignment
(31:06) Getting Serious About the Threat of AI
(47:23) Predictions for AI Development by 2027
(48:33) Public and Government Reactions to AI Concerns
(49:27) Policy Recommendations for AI Safety
(52:22) Diverging Views on AI Alignment Timelines
(1:01:30) The Role of Public Awareness in AI Safety
(1:02:38) Reflections on Insider vs. Outsider Strategies
(1:10:53) Future Research and Scenario Planning
(1:14:01) Best and Worst Case Outcomes for AI
(1:17:02) Final Thoughts and Hopes for the Future

 

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

0:00 47:12

Ep 64: GPT 4.1 Lead at OpenAI Michelle Pokrass: RFT Launch, How OpenAI Improves Its Models & the State of AI Agents Today

Hosts
Jacob Effron Patrick Chase Jordan Segall Erica Brescia
Guests
Michelle Pokrass
Keywords
GPT-4.1 OpenAI AI agents model training instruction-following long context AI startups fine-tuning multimodal capabilities data efficiency

In this episode, I sit down with Michelle Pokrass, who leads a research team at OpenAI within post-training focused on improving models for power users: developers using OpenAI models in the API and power users in ChatGPT. We unpack how OpenAI prioritized instruction-following and long context, why evals have a 3-month shelf life, what separates successful AI startups, and how the best teams are fine-tuning to push past the current frontier.

If you’ve ever wondered how OpenAI really decides what to build, and how it affects what you should build, this one’s for you.

 

(0:00) Intro

(1:03) Deep Dive into GPT-4.1 Development

(2:23) User Feedback and Model Evaluation

(4:01) Challenges and Improvements in Model Training

(5:54) Advancements in AI Coding Capabilities

(9:11) Future of AI Models and Fine-Tuning

(20:44) Multimodal Capabilities

(22:59) Deep Tech Applications and Data Efficiency

(24:14) Preference Fine Tuning vs. RFT

(26:29) Choosing the Right Model for Your Needs

(28:18) Prompting Techniques and Model Improvements

(32:10) Future Research and Model Enhancements

(39:14) Power Users and Personalization

(40:22) Personal Journey and Organizational Growth

(43:37) 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

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4.9 rating 49 reviews

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4.9 ratings 46 reviews

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