Village Global Podcast

Sherwood Callaway is the founder and CEO of Sazabi, an AI-native observability platform, and a repeat YC founder. He previously worked as an early infrastructure engineer at Brex, where he built the systems that kept one of the fastest-growing fintechs in the world running.Village Global Luminary LP Lindsay Pettingill sits down with Sherwood for a conversation that moves from his unconventional path into engineering to the contrarian bets behind Sazabi. They dig into why Sherwood believes logs alone can replace metrics and traces, why dashboards mostly serve anxiety rather than insight, and what a world of self-healing software could actually look like. Along the way, Sherwood reflects on the 40-page manifesto that became Sazabi's founding thesis, the angel investor strategy that brought over 100 founders and technical leaders onto his cap table, and the maximalist, Blade Runner-inspired brand built around a name pulled from a 1980s anime. The episode closes on a more personal note, touching on his orthopedic surgeon father's late-career turn toward vibe coding and his sister Hadley's stint at Sazabi as its first non-technical hire before business school.Thanks for listening. If you like what you hear, please review us on your favorite podcast platform. Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal. Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Welcome to Recall Sessions – a new series on the Village Global Podcast.Hosted by Somrat Niyogi, Partner at Recall Capital, each episode goes deep on go-to-market: how the world's most successful companies got their first customers. In this episode, Itai Damti, Co-Founder & CEO of Unit, joins Somrat to break down how Unit went from a year of stealth building with no committed customers to becoming the leading embedded finance platform – moving over $50 billion annually and powering programs at seven public companies.Itai talks about the bet he and co-founder Doron Somech made on a market that barely existed, why they spent a full year building before going to market, how their first customer came through a LinkedIn message, and what he's learned about selling infrastructure that changes how buyers think.He also shares a framework for categorizing buyers – deciders, explorers, and the "unawares" – and why minding the chasm between your first 5% of customers and the next 95% is where companies live or die.Thanks for listening – if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is a short excerpt from our full conversation with Shishir Mehrotra, CEO of Superhuman (formerly Grammarly), and Village Global's Ben Casnocha.Shishir and Ben discuss the "Silicon Valley Inc. vs. Google Inc." framework for understanding career tradeoffs, when recruitment firms add value vs. when they don't, and how to design a hiring process that produces great outcomes — including the critical role of reference checking.Watch the full episode here: https://youtu.be/S7UO7AOLgBAThanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is a short excerpt from our full conversation with Henry Shi (Anthropic, co-founder of Super.com) and Village Global GP Anne Dwane.Henry and Anne discuss the three paths available to successful founders, why traditional venture capital often becomes a sales job, the rise of "seed-strapping" as a new funding model, and what ultimately led Henry to join a frontier AI lab instead of starting another company or becoming an investor.Watch the full episode here: https://www.youtube.com/watch?v=MN88HLFx8-MListen to the full conversation here: https://podcasts.apple.com/us/podcast/from-%24200-million-revenue-founder-to-frontier-lab-with/id1316769266?i=1000746090022Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is an excerpt from our full conversation with Shishir Mehrotra, CEO of Superhuman (formerly Grammarly).Shishir discusses why Grammarly is one of the most underestimated companies in Silicon Valley, how it's transforming from a grammar tool into an open platform for AI agents, and why "assist" AI—which meets you where you work—may be more powerful than chat or autonomous agents.Watch the full episode here: https://www.youtube.com/watch?v=S7UO7AOLgBAThanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Henry Shi, founder of Super.com (scaled to $200M+ annual revenue, 50 million users, profitable), joins Village Global GP Anne Dwane to discuss his unconventional path from founder to Anthropic.Henry shares why he stepped back from his company at its peak, what he learned during his gap year building AI resources in public, the patterns he discovered tracking lean AI companies, and why he ultimately chose a frontier lab over VC or starting another company. He also gives a candid look inside Anthropic's culture and shares his predictions for what's coming in 2026. Mentioned in the Episode:Lean AI Leaderboard: https://leanaileaderboard.com/AI Crash Course (GitHub): https://github.com/henrythe9th/AI-Crash-CourseAI 2027 Report: https://ai-2027.com/Super.com: https://www.super.comAnthropic: https://www.anthropic.comHenry on X: https://x.com/henrythe9thsHenry on LinkedIn: https://www.linkedin.com/in/henrythe9th/Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup