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Sure Shot Entrepreneur Newsletter

SAIF, Mayfield, FirstShift: The Sure Shot Entrepreneur Newsletter

Published 11 days ago • 2 min read

Hello Reader,

Human-centric technology will win. In a world flooded with shiny new innovations each day, it’s easy to lose sight of what truly matters. One helpful way to cut through the noise is to revisit past innovation booms and look for patterns that stood the test of time.

During the dot-com era, countless companies emerged, and most vanished. But a few exceptional ones endured: Amazon, Google, eBay. What set them apart? A deep commitment to user-centric design and trust.

Amazon relentlessly earned customer trust and redefined consumer behavior around e-commerce. eBay built elegant mechanisms that fostered trust in peer-to-peer transactions, making technology feel invisible. Google turned the overwhelming sprawl of the internet into a single, simple text box. It was powerful, yet effortless to use.

Today, as we navigate the rapid rise of AI, we’ve come full circle to another text prompt. And again, it’s the human-centered companies that are poised to lead. The winners will be those that earn trust, behave responsibly, abstract away complexity, and build with intention. That’s what thoughtful investors are looking for.

This week on my podcast, Geoff Ralston shared sharp insights on this very idea. A few weeks ago, Vijay Reddy echoed similar themes in our conversation.


– Gopi Rangan, Host of the The Sure Shot Entrepreneur podcast​

Startup Corner: FirstShift

​Firstshift, a pioneer in AI-powered supply chain planning, recently launched Pluto, a generative AI copilot designed to transform how planners make decisions. Available in both natural language mode and a query-builder interface, Pluto allows users to ask complex questions in plain English, or build detailed queries with guided prompts, to instantly generate actionable insights with charts and diagnostics. As Firstshift CEO Hari Menon notes, Pluto empowers teams to respond to demand shifts, disruptions, and inventory challenges “with greater speed and precision,” without needing additional staff or technical expertise. With AI assisting supply chain teams with a variety of tasks (from demand sensing to integrated business planning), Pluto is setting a new standard in operational agility and resilience.

Podcast Entries:

Stop What Could Go Wrong and Build a Safer AI Future

​My guest in episode 167 is Geoff Ralston, founder of the Safe Artificial Intelligence Fund (SAIF) and former President of Y Combinator. Geoff shares why he believes we’re entering a new era where AI systems act less like tools and more like autonomous cognitive agents. He outlines the most pressing risks in AI, ranging from biosafety and misinformation to interpretability, and explains why early-stage investments in safety, security, and governance are essential for building a better future. Geoff also offers practical advice for founders building in the AI space, emphasizing the importance of aligning product-market fit with long-term safety and social responsibility.

Connected Insights: Engage With Customers Sooner Than Later When You Build AI Solutions

​In episode 139, I spoke with Vijay Reddy, partner at Mayfield, who emphasized a foundational principle: start with real-world problems before letting AI serve as a solution. Vijay described Mayfield’s people-first ethos, which is investing in founders who combine domain expertise with cutting-edge AI skills. He urged entrepreneurs to begin with customer obsession, not a tech-first mindset. His focus on cognitive plumbing and Cognition-as-a-Service, where AI acts as a co‑worker rather than just a tool, underscores the idea that aligning thoughtful design with user and societal needs yields stronger, more responsible AI ventures.

Community Involvement: AI Venture Lab

Geoff Ralston also serves as a mentor and advisor at AI Venture Lab, INSEAD’s flagship program designed to help early-stage founders worldwide—from ideation to demo-ready ventures—by combining new frameworks, peer study groups, and masterclasses led by global mentors and AI experts. The Lab’s mission is twofold: empower entrepreneurs to build, test, and scale AI-powered businesses, and generate research-backed insights on how AI is transforming venture creation for policymakers, managers, and investors.

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Sure Shot Entrepreneur Newsletter

Gopi Rangan

Enable Peace of Mind for all. We believe in mission-driven entrepreneurs at the earliest stages before the rest of the world realizes the impact of their visionary ideas. This newsletter pairs well with our podcast that shares all the funders and founders' knowledge to startup and scale your ideas. All the best, Gopi

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