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.

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Moe Katib is the founder and CEO of One (withone.ai), an enterprise-level infrastructure platform that gives AI agents authenticated, reliable access to hundreds of software applications and verified actions. Before One, he spent 12 years solving enterprise integration problems, building the knowledge base that became the foundation for what he's building today.

Village Global GP Anne Dwane sits down with Moe to trace the story behind One: from growing up in Damascus selling packaged chicken out of his uncle's factory, to building water-pump automation devices growing up, to immigrating to Canada after his invention was stolen by a government-connected company. They cover what a decade of enterprise integration work taught him about agent infrastructure, why he made the counterintuitive decision to open source all the integrations he had assembled, and why trust, not speed or scale, is the real unlock for agentic AI adoption.

Moe also shares his own experience running his email entirely through an agent, including the moment his AI sent a rude message to a major VC on his behalf, and what that revealed about the identity problem at the heart of agentic software.

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Alex Jekowsky is the co-founder and CEO of Cents, the all-in-one software, hardware, and payments platform for the laundry industry. A Forbes 30 Under 30 recipient, he sold his first company at 23, and last month closed a $140 million Series C. Cents now powers more than 1 in 6 laundromats in the country and processes over $1 billion in payments a year.

Somrat Niyogi sits down with Alex to go from the very beginning: the aha moment that led him to laundromats, how he got his first customers through cold emails and contact forms, why he priced Cents at a flat $299 from day one, and what it actually took to build a durable go-to-market motion in a market most investors wrote off. They also cover the distributor strategy that unlocked scale, how the Laundry Works acquisition changed everything, what Alex gets right about hiring slow, and why he thinks agentic AI is the only version of AI that actually matters for SMB operators.

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In this episode of the Village Global Podcast, Box CEO Aaron Levie joins Village Global Chairman Reid Hoffman and host Ben Casnocha live on stage at a Village Global event. They get into what agents actually do to SaaS, where startups should go on offense, and what twenty years of building Box has taught Aaron about leveling up as a founder.

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Somrat Niyogi sits down with two of the most experienced comms operators in tech: Kelly Boynton, Head of Communications at Gusto, and Paul Loeffler, former SVP of Communications and Brand at BILL.

Kelly spent 15 years across agency and in-house roles before Gusto, including at Facebook, Instagram, Intuit, Navan, and DocuSign. Before BILL, Paul led integrated communications at Gusto and was at Atlassian pre-IPO, helping scale it as a public company.

They cover what founders get wrong about launches and PR, when an agency is worth it (and when it is not), why your story should be about value rather than valuation, why reporters write about trends rather than companies, why 95% of stealth companies should not be in stealth, and the comms playbook for breaking through the noise.

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Deon is the co-founder and CEO of Espa Labs. His previous company, Forethought, was a TechCrunch Disrupt winner in 2018, scaled to roughly a billion customer interactions a month, and was recently acquired by Zendesk, where Deon now serves as advisor.

Village Global GP Anne Dwane sits down with Deon to talk about the launch and the journey that brought him here. They cover what he learned scaling Forethought through the GPT-1 to GPT-4 era, why the Iron Man Jarvis vision is finally within reach for everyone (not just Silicon Valley), the three pillars of Espa, why the model labs have perverse incentives that leave the door open for a new app-layer winner, the surprising network effect that emerges when one Espa starts talking to another, and where personal productivity AI is heading over the next five to ten years.

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