Unsupervised Learning with Jacob Effron
by Redpoint Ventures
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.
Hosted by Redpoint investor Jacob Effron alongside Patrick Chase, Jordan Segall and Erica Brescia.
Unsupervised Learning is a podcast by Redpoint Ventures, an early-stage venture capital fund that has invested in companies like Snowflake, Stripe, and Mistral.
Hosted by Redpoint investor Jacob Effron alongside Patrick Chase, Jordan Segall and Erica Brescia.
Episodes
Mentioned books
72 snips
Apr 23, 2026 • 55min
Ep 85: Has AI Infra Stabilized, FM Vibe Shift, & What's Next for Coding Agents
Shawn Wang (Swyx), AI engineer and operator at Cognition who organizes AI engineering events, joins to map current trends. He discusses whether AI infrastructure has stabilized. He dives into coding agents, the stickiness of Claude Code versus Codex, the rise of open models, and why memory and personalization are the next frontiers.
159 snips
Apr 9, 2026 • 59min
Ep 84: OpenAI’s Chief Scientist on Continual Learning Hype, RL Beyond Code, & Future Alignment Directions
Jakub Pachocki, OpenAI Chief Scientist focused on model capabilities, RL, and alignment. He discusses the rise of coding agents and autonomous research tools. He talks about math and physics as benchmarks, extending reinforcement learning to long-horizon tasks, chain-of-thought monitoring for alignment, and the societal risks of highly automated AI research organizations.
135 snips
Apr 2, 2026 • 54min
Ep 83: Owning the System of Record, AI-Native Org Charts, & Why ITSM is The Most Vulnerable Legacy Category
Jake Stauch, founder and CEO of Serval — building an AI-native employee support and ITSM platform — discusses why he built a full system of record and how that bet enabled competing with incumbents. He covers AI-driven codegen automations, safety guardrails for agent-driven workflows, and hiring as the core moat for scaling the company. Short, tactical, and future-focused conversations about architecture and org design.
58 snips
Mar 11, 2026 • 54min
Ep 82: Behind Legora's $550M Raise, Model Competition, Doubling Revenue Every Quarter, & US Expansion
Max Jungestål, CEO of Legora and builder of an AI-native legal software company, shares how a $550M raise fueled rapid US expansion and relentless product reinvention. He talks about rebuilding features after model shifts, competitive AI driving law firm adoption, and deliberate cultural moves like Stockholm onboarding to scale fast.
305 snips
Jan 29, 2026 • 1h 3min
Ep 81: Ex-OpenAI Researcher On Why He Left, His Honest AGI Timeline, & The Limits of Scaling RL
Jerry Tworek, former VP of Research at OpenAI and architect of reasoning models and Codex, shares why scaling hits limits and why continual learning matters for true AGI. He discusses the constraints of pre-training and RL, the economics pushing labs toward similar strategies, his reasons for leaving OpenAI, and a near-term robotics outlook with big societal stakes.
414 snips
Dec 18, 2025 • 1h 18min
AI Vibe Check: The Actual Bottleneck In Research, SSI’s Mystique, & Spicy 2026 Predictions
Ari Morcos, a research scientist focused on model interpretability, and Rob Toews, a tech investor, dive into the AI landscape post-NeurIPS. They discuss whether AI models are plateauing, the constraints of infinite lab capital on innovation, and the paradox of U.S. chip restrictions potentially speeding up China's self-sufficiency. Ari reveals the real bottleneck in AI is compute power, not ideas, while Rob predicts major shifts for OpenAI's leadership by 2026, and both foresee a Chinese open-source model taking center stage.
174 snips
Dec 15, 2025 • 48min
Ep 80: CEO of Surge AI Edwin Chen on Why Frontier Labs Are Diverging, RL Environments & Developing Model Taste
Edwin Chen, Founder and CEO of Surge AI, shares insights from his data infrastructure company supporting major AI labs like OpenAI and Meta. He discusses the pitfalls of optimizing for clickbait benchmarks, revealing how these practices mislead model quality. Chen emphasizes the importance of rigorous human evaluations over gaming benchmarks, and he critiques Silicon Valley's pivot culture. The conversation delves into the diversity of AI training approaches, advocating for multiple opinionated models tailored to specific needs in future AI development.
232 snips
Dec 10, 2025 • 56min
Ep 79: OpenAI's Head of Product on How the Best Teams Build, Ship and Scale AI Products
Join Olivier Godement, OpenAI's Head of Product for Business Products, as he dives into the future of AI in enterprise settings. Discover how GPT-5.1 and Codex are transforming industries like life sciences, enabling companies to cut drug development timelines significantly. Olivier shares insights on the challenges of job automation, the importance of cost reduction in AI adoption, and the critical role of reinforcement fine-tuning. He also discusses the potential of AI in coding and suggests that seamless integration could revolutionize how engineers work.
62 snips
Dec 5, 2025 • 1h 13min
Ep 78: Jordan Schneider, Host of China Talk, on AI Race, Key Policy Decisions & Unpacking Geopolitical Chip Tension
Jordan Schneider, host of China Talk and an expert on Chinese tech and AI, explores the market-driven dynamics of China's AI landscape, revealing how private capital shapes its growth. He discusses the impact of US export controls on China's computing capabilities and challenges the notion of government control over AI development. With a focus on robotics manufacturing, he highlights China's emerging advantages. Jordan also critiques the Goldilocks strategy, addresses US policies, and assesses Taiwan's geopolitical risks.
326 snips
Dec 2, 2025 • 42min
Ep 77: Anthropic’s Dianne Na Penn on Opus 4.5, Rethinking Model Scaffolding & Safety as a Competitive Advantage
Dianne Na Penn, a senior product leader at Anthropic, dives into the intriguing launch of Opus 4.5, highlighting its capabilities and strategic focus. She discusses the shift from traditional AI benchmarks to more open-ended evaluations. Dianne shares how Anthropic balances user feedback with ambitious development plans, enhancing enterprise applications. She emphasizes the importance of model alignment and authenticity in fostering independent thinking. The conversation also touches on the evolution of AI scaffolding and the potential for transformative long-running intelligence in the near future.
