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.

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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.

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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 synthesis

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.

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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.

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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.

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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.

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Aaron Harris was a partner at YC for 7.5 years where he funded Deel, OpenSea, Scale AI, Rappi, Lattice, and others. He also built YC's Series A program where he worked with founders on over 200 Series As and Bs that raised in excess of $3B in capital. He joined Sam Kirschner, VP at Village Global, to give Village Global founders helpful tips on fundraising.

Takeaways:

• Investors bet on stories, not just data. Your job? Tell a story of massive economic opportunity — not just how you fit into the future, but how you create it.
• Hype lowers the barrier to turn attention into excitement.
• Fundraising isn't the trophy, even though it's celebrated as such. But if you optimize for raising money, you get great at burning money and miss the real point: building something that lasts through the hype cycles.
• Think about raising money with terminal value in mind, not just the value of this current round.
• Raising an A: you'll need to raise about 20% of your company. Series B: 15-20%. Seeds are all over the place. More competition in a round means less dilution; less competition means more dilution. Hype helps reduce dilution.
• Be aware of dilution on SAFEs so that you don't all of a sudden start arguing about a point of dilution here or there on a given round.
• AI companies have been getting faster investor movement. The hottest deals land term sheets in 48 hours. Next tier? 1-2 weeks. Beyond that, a 2-6 week grind with unpredictable timing. After 6 weeks, rounds can stretch to 3-4 months where persistence is what leads to success.
• Understand the market and how investors think by having casual, no-pitch-deck coffee chats. The real signal? Not a follow-up meeting — that's just a VC's job. Look for action: are they willing to spend political capital for you? That’s true interest.

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.

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Kathy Copic is founder of Fieldwork Partners, where she works closely with early stage companies on scoping technical projects, getting early ML models into production, and helping them hire. She was interviewed by Lindsay Pettingill, Investment Partner at Village Global, during this masterclass for Village Global founders. 

Takeaways:

• Maintain at least three interview touchpoints to thoroughly evaluate candidates — rushing the process means missing vital signals about how well candidates understand your business and culture.
• Write job descriptions that focus on company mission and concrete first-90-day projects rather than generic skill requirements — this attracts candidates who are genuinely excited about your specific opportunity.
• Look beyond prestigious company names and degrees — strong candidates often demonstrate their passion through side projects, nonprofits, or other entrepreneurial pursuits.
• Foster interactive interviews where you're comfortable interrupting candidates — their response to dynamic discussion reveals more about their communication style and fit than scripted questions.
• Structure work trials carefully to benefit both parties — the best candidates are evaluating your team and work environment just as much as you're evaluating them.
• When competing with large tech companies, emphasize the concrete impact individuals can have in your startup rather than trying to match compensation packages.
• Build diverse teams by implementing clear interview rubrics, providing guidance on legal considerations, and equipping interviewers with specific talking points about why diversity matters to your company.
• For references, consider asking peers rather than managers when candidates are currently employed, but use references extensively to validate your assessments.

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.

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Eynat Guez, founder and CEO of Papaya Global, was interviewed by Ben Casnocha, co-founder and partner at Village Global, during this masterclass for Village Global founders.

Takeaways:

Show up to key meetings as the founder or executive team — don’t just send the sales team. It signals to the client that you’re personally invested and committed to making the deal a success.

Avoid being overly optimistic about where prospects stand. Serious signals include active texting, detailed questions about implementation, security questionnaires, and the involvement of additional stakeholders.

Be strategic about progressing meetings: PowerPoint to articulate vision, Excel for financials, and Word for legal details.

Build strong relationships with junior VCs as well as partners — they can provide introductions, market intelligence, and future opportunities as they advance in their careers.

Building relationships with clients shouldn’t stop after the deal closes. Ongoing check-ins help position your company as a long-term partner, not just a vendor.

Leaders should periodically dive deep into 2-3 departments or processes each quarter to challenge assumptions and drive innovation.

Engage with junior employees or frontline staff for fresh perspectives — their insights are often more candid than those of seasoned executives.

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.

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Auren Hoffman, CEO of SafeGraph and GP of Flex Capital, interviewed Ben Casnocha, Village Global co-founder and partner, on Auren's World of DaaS podcast. They are longtime friends and had a wide-ranging discussion on career strategy, evaluating founders, serendipity, wealth, and much more. We've cross-posted that conversation here.

Highlights:

• The relevance of what you know vs. who you know has been a debate in the career strategy space for decades. Ben believes that the “what you know” is often dependent on the “who you know” because with the advent of the internet, public information is accessible to all but the insights that live in the heads of the smartest people are not shared widely and require a personal relationship with someone to be able to access that information.
• Talent spotting is about finding value in the unexpected and recognizing the strengths in those who may not fit the typical mold. Sometimes people who have clear and obvious flaws in one area are overlooked by people who can’t see the brilliance beyond that particular flaw.
• Certain seasons of life are good for maximizing for serendipity and taking random coffee meetings. The key is to know what season of life you are in and whether it’s better in the long-term at that moment to be maximizing for serendipity or not. The pendulum will swing back around at some point.
• There’s a certain level of wealth where your wealth actually starts to detract from your level of happiness. Sometimes people are better served by aiming for a lower level of wealth in order to maximize for happiness.

Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.

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