Ep 67: Max Junestrand (CEO, Legora) on Differentiating and Pricing AI Apps & How the Legal Industry Will Evolve
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
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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, 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
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Ep 65: Co-Authors of AI-2027 Daniel Kokotajlo and Thomas Larsen On Their Detailed AI Predictions for the Coming Years
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
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Ep 64: GPT 4.1 Lead at OpenAI Michelle Pokrass: RFT Launch, How OpenAI Improves Its Models & the State of AI Agents Today
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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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
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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