Sierra

⚡️ Competing with ChatGPT and Sierra, building a $10M ARR company — Yasser Elsaid, Founder, Chatbase

May 2, 2026 · 1:00:26

Yasser Elsaid, founder of bootstrapped AI chatbot company Chatbase, discusses how he grew from a side project to $10M ARR in three years, reaching $1M in just 117 days. He explains why he never raised VC, relying instead on product-led growth, self-serve signups, and a content-driven go-to-market strategy. Elsaid shares specific tactics like warm outbound to signed-up users, leveraging LinkedIn virality in early AI days, and now moving toward outcome-based pricing for enterprise customers. He details Chatbase's evolution from a simple RAG chatbot into a 'chief customer officer' that handles support, sales, and onboarding while surfacing business insights from conversations. The episode also covers his transition from Toronto to San Francisco, his hiring philosophy favoring results-oriented engineers, and his daily use of both Claude Code and Codex for development.

⚡️Context Graphs: according to the authors — Jaya Gupta, Ashu Garg, Foundation Capital

Feb 4, 2026 · 33:44

Jaya Gupta and Ashu Garg of Foundation Capital introduce Context Graphs—the institutional memory of the 'why' behind business decisions, captured through decision traces of exceptions, overrides, and precedents that AI models often miss. They argue these graphs will become the defensible moat for the next generation of applied AI companies and Systems of Agents, citing early implementations at Player Zero, Olive, and Tesserae. The hosts distinguish Context Graphs from mere metadata or data meshes, emphasizing they emerge organically from automating specific workflows rather than as universal enterprise schemas. They predict that by 2026, hundreds of Context Graphs will be in production, a standard enabling stack will emerge, and the industry will shift from debating definitions to extracting value from the captured decision traces.

Brex’s AI Hail Mary — With CTO James Reggio (acquired for $5B by Capital One!)

Jan 17, 2026 · 1:13:27

Brex CTO James Reggio details the company's three-pillar AI strategy—corporate, operational, and product AI—arguing that SOP-driven agents outperform overengineered RL in finance ops like underwriting, KYC, and fraud. He explains why Brex built an internal AI platform (LLM gateway, prompt/version management, evals) before adopting Mastra for TypeScript-based multi-agent networks, where an EA-style orchestrator coordinates specialist agents via multi-turn conversations rather than single tool calls. The audit agent pattern separates detection, judgment, and follow-up to reduce false negatives. Brex also lets employees build their own AI stack (ChatGPT, Claude, Gemini) and runs agentic coding interviews internally, with the company growing 5X and cutting burn 99% in 18 months without adding engineers.

[State of AI Startups] Memory/Learning, RL Envs & DBT-Fivetran — Sarah Catanzaro, Amplify

Dec 30, 2025 · 28:43

Sarah Catanzaro of Amplify Partners argues that the DBT-Fivetran merger was not the death of the modern data stack but a path to IPO targeting $600M+ combined revenue, that data catalogs failed because they were built for humans rather than machines, and that RL environments are a fad. She notes that frontier labs use dbt and Fivetran for training data curation and agent analytics, and criticizes $100M+ seed rounds raised without near-term roadmaps. For 2026, she identifies personalization via memory and continual learning as the key retention unlock, observing that AI founders are unfamiliar with growth concepts like k-factor. She prefers real-world logs over synthetic RL environments, citing Cursor's use of user activity, and says the most exciting startups combine hard research problems (RAG, rule-following, continual learning) with applications that were previously impossible.

⚡️No, Don't Do Palantir for AI - Brendan Falk, Hercules (AUDIO FIXED)

Sep 18, 2025 · 35:08

Brendan Falk, founder of Zeus (now Hercules), explains why he abandoned his vision to become 'Palantir for AI' after six months of enterprise AI transformations. Targeting Global 2000 companies with $5–10M contracts, he found that each use case required custom development, messy data, and high ongoing maintenance, with work scaling poorly across contract sizes. He also faced existential threats from specialized vendors like Decagon and Sierra, who could outspend and out-focus on single use cases. Falk pivoted to Hercules.app, an AI website builder that ships production apps, white-labeling payments and email. He argues the app builder market (Wix, Squarespace, Shopify) will expand with AI, and that brand and ease will sustain higher margins than developer tools like Cursor.

⚡️Ranking Agentic LLMs — Pratik Bhavsar, Galileo

Jul 14, 2025 · 34:10

Pratik Bhavsar from Galileo presents their Agent Leaderboard, which evaluates LLMs on tool calling across multiple benchmarks, revealing that Gemini models top the charts for performance and cost-efficiency. The leaderboard, built on datasets like BFCL, XLAM, and Tau Bench, uses an LLM-as-judge metric called Tool Selection Quality (TSQ). Surprising findings include reasoning models like o1 struggling with multi-tool outputs, Mistral Small excelling as the best open-source model, and Llama models performing poorly. The episode also previews V2 of the leaderboard, which introduces domain-specific, harder, multi-turn scenarios with a user and tool simulator, and a new Action Completion metric to measure whether all user requests are accomplished.

Voice AI Masterclass — Kwindla Hultman Kramer and swyx

May 6, 2025 · 20:51

Shawn Wang and Kwindla Hultman Kramer announce a voice AI masterclass course, diving into the landscape of models like Dia and Parakeet, production deployment challenges, and future trends such as speech-to-speech and real-time video. Kwindla explains that telephony (Twilio) drives 99% of current monetizable voice AI, while open source frameworks like Pipecat enable low-latency multi-modal apps. The course covers turn detection, context management, and evals, with 28 sessions featuring partners like OpenAI, Google, and NVIDIA. The goal is to jumpstart builders from prototype to production, with real-time video expected to hit its inflection point by year-end.

The AI Architect: Bret Taylor

Feb 11, 2025 · 1:35:59

Bret Taylor, CEO of Sierra and chairman of OpenAI, recounts engineering AI's future across three eras — rewriting Google Maps' frontend in a weekend (cutting un-gzipped code to 20K), building Sierra's in-house agent platform for consumer brands like Sonos and SiriusXM, and navigating OpenAI's leadership crisis. He argues that AI agents' core abstractions are still pre-React, compares today's agents to jQuery, and predicts that outcome-based pricing will dominate as agents complete jobs rather than assist humans. He urges software engineers to move up the stack toward domain-specific agents and to embrace Rust-like languages for AI-generated code, emphasizing formal verification and safety. Taylor also shares how OpenAI prioritizes mission over product features, and why the relationship with Microsoft remains OpenAI's most important partnership.

The State of AI Startups in 2024 [LS Live @ NeurIPS]

Dec 21, 2024 · 26:35

Sarah Guo and Pranav Reddy argue that 2024 has become a far friendlier ecosystem for AI startups, with the model landscape shifting from OpenAI's near-monopoly to a competitive field where Google's Gemini now leads LMSys Arena and open-source models like Llama 8B score ten points higher on MMLU than Mistral 7B a year ago. They note that OpenAI's API cost has dropped 80-85% in 18 months, and total OpenAI API share fell from ~90% to ~60% as customers switch. The funding environment is rational, not a bubble, with foundation-model labs raising $30-40B but most startups seeing sane valuations; one portfolio company grew from zero to twenty million in PLG-style spending. Key startup themes include first-wave service automation (Sierra, Decagon, Harvey, EvenUp), better search and new friends (Perplexity, Glean, Character, Replica), and democratized creativity (Midjourney, HeyGen). They argue the 'GPT wrapper' narrative is false—applications capture value—and that incumbents face innovator's dilemma because AI changes business models (outcomes-based pricing) and data needs (reasoning traces rarely saved). The speed of change and new markets (legal, healthcare, defense) structurally favor…

Language Agents: From Reasoning to Acting — with Shunyu Yao of OpenAI, Harrison Chase of LangGraph

Sep 27, 2024 · 1:26:33

Shunyu Yao of OpenAI and Harrison Chase of LangChain discuss the evolution of language agents, arguing that combining reasoning and acting through techniques like ReAct remains foundational, while tool design and cognitive architectures like CoALA will shape the next wave. Shunyu traces his work from text games to ReAct, showing how thinking as an action improves reliability; Harrison explains LangChain's adoption and the shift to LangGraph for stateful orchestration. They emphasize agent-computer interfaces (ACI) as a neglected area, noting that SWE-Agent's success came from optimizing tools for models, not humans. The conversation covers memory types (semantic, episodic, procedural) and applies CoALA's three dimensions to current systems. They highlight promising applications: customer support, coding agents, and spreadsheet-style UX for batch operations. Shunyu stresses that better benchmarks like SWE-Bench (which solved 30% of GitHub issues) and TauBench (best model 48%) are critical, and that data—not architecture—will drive future model improvements.