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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 how AI coding tools have evolved from autocomplete to junior engineers, what skills will matter when writing code becomes obsolete, and whether humans or AI will end up as the boss in the future of work. Listen to the full episode here: https://podcasts.apple.com/us/podcast/village-global-podcast/id1316769266?i=1000746090022 Watch the full episode here: https://www.youtube.com/watch?v=MN88HLFx8-M 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 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=S7UO7AOLgBA 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). Shishir discusses the fundamental differences between working at big tech companies versus startups, why skills at large companies are less transferable than you think, and what separates world-class recruiting processes from mediocre ones. Watch the full episode here: https://www.youtube.com/watch?v=S7UO7AOLgBA 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

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

This is a short excerpt from our full conversation with Zoom founder and CEO Eric Yuan and LinkedIn co-founder / Village Global Chairman Reid Hoffman. Eric and Reid discuss what separates companies that last from those that flame out, why hypergrowth can hide critical problems, and how founders should think about their "theory of the game" for the next ten years. Listen to the full episode here: https://podcasts.apple.com/us/podcast/the-future-of-work-with-zoom-ceo-eric-yuan-and-reid-hoffman/id1316769266?i=1000744325171 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

Magnus Sandstrom and Debbie Wiss are senior partners at Swing Search, specializing in go-to-market roles at director, VP, and head levels for nearly 20 years. They joined Village Global partner Lindsay Pettingill to discuss the mistakes founders make when hiring their first sales and marketing talent, and how to get it right. Takeaways: Don't go too senior too early. Look for someone who can see around corners, not over mountains. Senior hires want teams and foundations. You need someone doing outbound calls and chasing deals.Don't try to solve product-market fit with a go-to-market hire. Talk to customers first. If you're pre-PMF, it's too soon to hire sales.You'll never leave sales. Even $100M+ CEOs are on sales calls. Accept this reality and get good at it rather than trying to hand it off.Strong sellers know their metrics to the decimal. "112.2% quota attainment" reveals discipline and ambition. "Around 100%" is a red flag.Hire two founding AEs, not one. They work in the trenches together while competing. If one doesn't work out, you still have revenue coming in.Marketing is more complex than sales. Define whether you need product marketing, demand gen, or brand. Wanting someone analytical and creative is unicorn territory.You can't delegate what you can't document. Write down your processes before expecting new hires to execute them.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 Zoom founder and CEO Eric Yuan and LinkedIn co-founder Reid Hoffman. Eric and Reid discuss where startups can compete against big tech in the AI era, why enterprise adoption of AI tools remains surprisingly slow, and what founders should focus on when selling AI products to enterprise customers. Listen to the full episode here: https://podcasts.apple.com/us/podcast/the-future-of-work-with-zoom-ceo-eric-yuan-and-reid-hoffman/id1316769266?i=1000744325171 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

Eric Yuan is the founder and CEO of Zoom. Reid Hoffman is the co-founder of LinkedIn. Both are luminary LPs at Village Global. They joined Village GP Ben Casnocha to discuss the future of AI agents, digital twins in the workplace, selling AI to enterprise, and what it takes to build companies that endure. Takeaways:Digital twins will handle meetings you're unsure about attending. Your AI can join internal meetings, summarize key points, and alert you only when your presence becomes critical. This frees you to focus on what truly matters.External AI interactions are coming too. Eventually, digital twins could negotiate contracts, discuss pricing, and handle preliminary conversations before humans finalize agreements.Enterprise customers want partners, not just products. When selling AI to enterprise, become a trusted guide through anxiety-ridden territory. Trust matters as much as features, especially when customers feel behind.Make customers part of your innovation cycle. Get enterprise customers deploying early, even partially. The unique data they generate becomes your moat that competitors can't replicate.Focus on vertical markets with domain expertise. Generic horizontal AI products are vulnerable to big players who can give similar tools away for free. Build where deep domain knowledge creates defensibility.Hypergrowth hides problems. Rapid revenue growth can mask fundamental issues in your product and operations. The best scenario is growing fast while proactively fixing hidden problems, but that's extremely hard.Theory of the game matters more than current metrics. Companies aren't valuable in a year; they're valuable in ten years and beyond. Have a clear theory for how your initial traction compounds into long-term value.Be honest with yourself about durability. Rapid early success doesn't automatically mean you have a long-term strategy. Understand what's driving growth and whether those factors will last.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 Airtable founder and CEO Howie Liu. Watch the full episode here: https://www.youtube.com/watch?v=rCR-zFXiXKA&t=2s Howie spent 2.5 years building Airtable before launching – and only talked to about a dozen customers in that time. In this clip, he explains why that approach made sense for a platform company, and how founders can validate ideas without drowning in customer discovery.

Van Jones is a political commentator, author, and former Obama White House advisor. Phaedra Ellis-Lamkins is founder and CEO of Promise, a software company transforming how governments deliver services to people in need. They joined the Village Global team to discuss what founders building in complex sectors need to know about power, narrative, and influence.  Takeaways: Political people often operate on emotion and relationships, rather than rationality. When selling to the government, demonstrating genuine care matters more than demonstrating expertise.Relationships precede transactions. Government buyers want to feel like partners in solving a problem, not targets of a sales pitch. Staff them like a colleague, not a customer.Authenticity cannot be manufactured. Know your (and your company’s) deep "why" and let it show. People can always tell when you're running a script on them.Fame and brand are a hack for time. Walking into a room where people already know and trust you changes everything about the conversation that follows.Your founding story is a strategic asset. People want to belong to something meaningful. A compelling origin story turns government contacts into advocates who champion you behind closed doors.Find the sliver of alignment. Working with someone you disagree with on nine out of ten issues can still yield results if you're aligned on the one thing that matters. Principled, narrow partnerships can achieve what ideological purity cannot.For mission-driven companies, revenue is how you measure impact. If your product serves the mission, making more money means helping more people.Choose investors like you'd choose a spouse. Turning down better terms to work with people you trust pays off. When a crisis hits or you need to pivot, those relationships let you make the best decision for the company without panic.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

Jennifer Tejada is CEO of PagerDuty, a public company serving 30,000+ customers worldwide. She joined Village Global GP Ben Casnocha for a masterclass on scaling in the AI era, followed by live feedback sessions with four founders building AI-native companies. Takeaways: Enterprise sentiment has shifted from “fear of missing out” to “fear of getting in.” Customers are anxious about security, resilience, and managing the people transition.Know what gets your customer promoted and what gets them fired. Different personas care about different things. A CIO has different anxieties than a developer or CMO.Pricing is a strategic foundation, not a tactical enabler. Start with value realization for the customer, then build pricing metrics that tie back to that value. Consumption-based models are popular, but predictability matters more than novelty.Transparency is becoming an expectation. Customers want instrumentation in your product that makes their consumption and costs visible. Nobody likes surprises when managing margins.The AI transformation is moving faster than any previous shift. Old playbooks don't always apply. The people willing to embrace change and experiment with new ways of operating will win faster.Build your CEO village. Having a trusted network of other CEOs who understand the unique pressures of the role makes all the difference. Invest in that community on a daily basis.Psychology matters in people transitions. Asking employees to use AI to replace themselves won't work. Think differently about how you organize to get work done while helping people transition to where they can add value. 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

Amjad Masad (@amasad), founder and CEO of Replit, and Yohei Nakajima (@yoheinakajima), Managing Partner at Untapped Capital, joined Village Global partner Ben Casnocha for a live masterclass with Village Global founders. Takeaways: AI agents are rapidly evolving, with coding and deep research agents showing the most traction today. But general-purpose assistants are still brittle — trip-planning and high-context tasks remain hard. Replit Agent shows how quickly full-stack applications can be built today, sometimes in under an hour — even by non-technical users. What matters most isn’t a CS degree, it’s traits like curiosity, grit, and systems thinking. Many AI startups are too quick to claim “moats” when most don’t really have one. True defensibility requires deep domain insight, unique data, and the right founder traits. The rise of vertical AI agents is compelling — specialists outperform general agents for now. A real AGI will change everything, and it’s so disruptive it’s not even worth planning around. The best investors still look for timeless traits: hard-charging, resourceful founders, attacking stagnant industries. AI changes a lot — but not what makes a great early-stage team. Tools like Replit are making vibe coding (yes, even for non-coders) a superpower. From executive dashboards to lightweight Crunchbase clones, agents are already creating real enterprise value. Don’t over-engineer AI use cases. Start with internal tools or things you’ve always wanted to build. The best projects often come from personal curiosity and side projects.Resources mentioned:Replit – The coding platform behind Replit Agent, enabling fast full-stack app creation with AI VCpedia by Yohei Nakajima – A startup intelligence platform vibe-coded with Replit Agent Tweet: $150k → $400 NetSuite extension – Real-world example of arbitrage using Replit TED Talk on Grit by Angela Duckworth – Referenced by Amjad as a key trait for AI builders “Perfectionism” blog post by Amjad Masad – Why it holds builders back and how to overcome it Seven Powers by Hamilton Helmer – The strategy book Amjad calls the best resource on real moats NEO – A fully autonomous ML engineer Layers – An autonomous AI marketing agent that lives in your IDE Basis – A vertical AI agent for accounting firms NDEA – A new lab (founded by François Chollet & Mike Knoop) exploring AGI with program synthesisThanks 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.vc or get in touch with us on Twitter @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.vc/signup

Jacob Mullins, Venture Partner at Village Global, welcomes Kristen Ostro, founder and CEO of Strut Consulting, to discuss the foundational elements that set venture capital firms up for long-term success. Kristen shares how her career began under the mentorship of Dick Kramlich at NEA, where she was trained in the core values and operational excellence that have shaped her approach to supporting dozens of VC firms across Silicon Valley. Drawing on this experience, Kristen explains why establishing a clear mission, vision, and values (MVV) framework is essential for firm alignment, decision-making, and building a resilient culture. Kristen outlines the common pitfalls firms face when they skip the MVV exercise, such as misalignment, wasted resources, and cultural drift, and offers actionable advice for integrating MVV into hiring, branding, and succession planning. She emphasizes that it’s never too late for a firm to revisit and refine its core principles, and shares practical tips for making the process collaborative and authentic. Listeners will gain valuable insights on how to differentiate their firm in a competitive market, attract top talent, and create a legacy that stands the test of time. Kristen’s reflections, inspired by her early training with one of venture capital’s founding fathers, offer a roadmap for building a values-driven organization that can thrive for decades. VC Mastermind is a private podcast for VC Managing Partners. Designed for senior decision-makers at VC firms managing $50 million to $5 billion of institutional capital, VC Mastermind delivers premium insights, peer exchange, and operational best practices across all stages of a firm's life cycle. It was founded by Jacob Mullins (@jacob on X / twitter) – a 20-year veteran of the Silicon Valley startup tech and venture capital industry based in San Francisco. 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.vc or get in touch with us on Twitter @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.vc/signup

Jacob Mullins, Venture Partner at Village Global, sits down with Ezra Roizen, General Manager of Advsr and author of "The Magic Box Paradigm," to demystify the world of startup mergers and acquisitions (M&A) on Jacob’s private podcast, VC Mastermind, which we are cross-posting on the Village Global podcast. Drawing on decades of experience as both an entrepreneur and investment banker, Ezra shares his unique framework for maximizing M&A outcomes, emphasizing that successful startup exits are driven not by a traditional sales process, but by building strategic relationships and unlocking future value for acquirers. Ezra introduces the "Magic Box Paradigm," a visual and practical approach that helps founders and investors focus on the unique value their company can unlock for specific buyers—what he calls the "purple boxes." He explains why M&A is fundamentally different from fundraising, how to avoid the pitfalls of a sales-driven mindset, and why starting early with strategic relationship-building is key. The conversation covers actionable advice for VCs and board members on how to guide their portfolio companies, the importance of thought leadership, and how to navigate both strategic and private equity exits. Listeners will come away with a fresh perspective on startup M&A, including when to bring in advisors, how to structure deals creatively, and why conventional wisdom—like relying on competitive bidding or rushing to term sheets—often falls short. Whether you’re a founder, investor, or board member, this episode offers a masterclass in preparing for and executing high-impact M&A outcomes. VC Mastermind is a private podcast for VC Managing Partners. Designed for senior decision-makers at VC firms managing $50 million to $5 billion of institutional capital, VC Mastermind delivers premium insights, peer exchange, and operational best practices across all stages of a firm's life cycle. It was founded by Jacob Mullins (@jacob on X / twitter) – a 20-year veteran of the Silicon Valley startup tech and venture capital industry based in San Francisco. 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.vc or get in touch with us on Twitter @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.vc/signup

Abhay Parasnis is founder and CEO of Typeface, is former CTO/CPO at Adobe, and sits on the board of Dropbox and Schneider Electric. He joined Ben Casnocha, co-founder and partner at Village Global, for a live masterclass for Village Global founders. Takeaways: If you can break into the top tier of the enterprise market, it’s hard to dislodge you.Big platforms like Microsoft, Google, and OpenAI are eager to prove their tech's power. If you position your startup as a prime showcase for their platform, you become a strategic asset.When selling to enterprise, understand the company's macro strategy in the market, but also know what the on-the-ground person needs to close deals.With the rise of agents and agentic automation, even the workflow layer isn’t safe. As these systems gain richer context, they’ll redefine automation in SaaS. Just like today’s platform vs. app debate, tomorrow’s battle will be legacy workflows vs. agents.Success in AI isn’t just about top-tier products—it’s about being a consultative partner to help them with change management.There’s a common fear about embracing a custom data training strategy — it’s expensive, complex, and feels like the domain of big players. But starting narrow and accumulating distinct data early is key. It drives real AI differentiation and builds critical internal muscle in engineering and product.Value-based pricing means customers are less price-sensitive because it ties directly to their top-line business, unlike commodity pricing, which faces constant cost pressure. Instead of charging per word, image, or seat—models that AI disrupts—pricing should align with outcomes, ensuring long-term sustainability.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.vc or get in touch with us on Twitter @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.vc/signup