Pinecone

⚡️ 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.

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.