Investing In People, AI, and the Future of Work with Virginie Raphael

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Investing In People, AI, and the Future of Work with Virginie Raphael

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In this episode, I'm joined by Virginie Raphael — investor, entrepreneur, and philosopher of work — for a wide-ranging conversation about incentives, technology, and how we build systems that scale without losing their humanity. We talk about her background growing up around her family's flower business, and how those early experiences shaped the way she thinks about labor, value, and operating in the real economy. That foundation carries through to her work as an investor, where she brings an operator's lens to evaluating businesses and ideas. We explore how incentives quietly shape outcomes across industries, especially in healthcare. Virginie shares why telehealth was a meaningful shift and what needs to change to move beyond one-to-one, supply-constrained models of care. We also dig into AI, venture capital, and the mistakes founders commonly make today — from hiring sales teams too early to raising too much money too fast. Virginie offers candid advice on pitching investors, why thoughtful cold outreach still works, and how doing real research signals respect and fit. The conversation closes with a contrarian take on selling: why it's not a numbers game, how focus and pre-qualification drive better outcomes, and why knowing who not to target is just as valuable as finding the right people. If you're thinking about the future of work, building with intention, or navigating entrepreneurship in an AI-accelerated world, this episode is for you. And for more conversations like this, join us at Snafu Conference 2026 on March 5th, where we'll keep exploring incentives, human skills, and what it really takes to build things that last. Start (0:00) Reflections on Work, Geography, and AI Adoption Virginie shares what she's noticing as trends in work and tech adoption: Geographic focus: she's excited to explore AI adoption outside traditional tech hubs. Examples: Atlanta, Nashville, Durham, Utah, Colorado, Georgia, North Carolina, parts of the Midwest. Rationale: businesses in these regions may adopt AI faster due to budgets, urgency, and impatience for tech that doesn't perform. "There are big corporates, there are middle and small businesses in those geos that have budget that will need the tech… and/or have less patience, I should say, for over-hub technologies that don't work." She notes that transitions to transformational technology never happen overnight, which creates opportunities: "We always underestimate how much time a transition to making anything that's so transformational… truly ubiquitous… just tends to think that it will happen overnight and it never does." Robin adds context from her own experience with Robin's Cafe and San Francisco's Mission District: Observed cultural and business momentum tied to geography Mentions Hollywood decline and rise of alternative media hubs (Atlanta, Morocco, New Jersey) Virginie reflects on COVID's impact on workforce behaviors: Opened a "window" to new modes of work and accelerated change: "There were many preexisting trends… but I do think that COVID gave a bit of a window into what was possible." Emphasis on structural change: workforce shifts require multi-year perspective and infrastructure, not just trends. Investor, Mission, and Capital Philosophy Virginie clarifies she is an investor, not a venture capitalist, resisting labels and prestige metrics. "I don't call myself a venture capitalist… I just say investor." Focuses on outcomes over categories, investing in solutions that advance the world she wants to see rather than chasing trendy tech sectors. "The outcome we want to see is everyone having the mode of work that suits them best throughout their lives." Portfolio themes: Access: helping people discover jobs they wouldn't otherwise know about. Retention / support: preventing workforce dropouts, providing appropriate healthcare, childcare, and caregiving support. "Anyone anywhere building towards that vision is investible by us." Critiques traditional venture capital practices: Raising VC money is not inherently a sign of success. "Raising from a VC is just not a sign of success. It's a milestone, not the goal." Concerned about concentration of capital into a few funds, leaving many founders unsupported. "There's a sense… that the work we do commands a lot less power in the world, a lot less effectiveness than holding the capital to hire that labor." Emphasizes structural, mission-driven investing over chasing categories: Invests in companies that prevent workforce dropouts, expand opportunity, and create equitable access to meaningful work. Portfolio strategy is diversified, focusing on infrastructure and long-term impact rather than quick wins. "We've tracked over time what type of founders and what type of solutions we attract and it's exactly the type of deal that we want to see." Reflects on COVID and societal trends as a lens for her investment thesis: "COVID gave a bit of a ...

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