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How do you go from deeply technical IC to leading 100+ engineers - and still stay close to the tech? Prashant Ramarao, SVP of Engineering & Head of AI @ Yahoo shares lessons from his unconventional leadership journey, exploring the mindset shift from expert IC to executive! We cover how to scale your leadership while maintaining technical credibility and how to effectively communicate with GMs & other non-technical stakeholders. Plus, Prashant shares personal AI projects that enhanced his technical credibility, leadership skills & understanding of how to integrate AI into products If you’re navigating the leap from technical to strategic, or scaling your leadership, this one’s for you.

Prashant is a hands-on technology executive with extensive experience in software engineering, leading large organizations, specializing in AI / ML, and large-scale systems architecture. With advanced degrees in computer science and engineering leadership, he excels at defining technical strategies that align with business goals, delivering results, and fostering high-performing, cross-functional teams. He cares about engineering excellence, leveraging cutting-edge technology to solve complex problems and scale operations for long-term growth. He has a lifelong passion for learning and looks for opportunities to challenge the status quo to drive change. He loves the outdoors and is a self-proclaimed podaholic - going on long hikes in Bay Area while listening to his podcasts is one of his favorite activities.

For over 30 years, Side has helped create unforgettable user experiences—from indies to AAA blockbusters like Silent Hill 2 and Baldur’s Gate 3.

• Behind Prashant’s rapid leadership evolution (3:26)
• Transitioning from IC to management: early steps and surprises (5:51)
• Navigating the mindset shifts from tech expert to people leader (7:31)
• Friction points in moving from informal to formal leadership (11:00)
• Skills for communicating with less technical audiences (13:46)
• Learning to talk with GMs & other non-technical leaders (16:32)
• Frameworks for effective meeting planning (19:03)
• Examples of communicating technical work to execs (20:08)
• Learning the impact of the “observer effect” (21:59)
• Incorporating feedback gathered by observing (27:03)
• Strategies for maintaining technical credibility as a senior leader (29:29)
• Why personal projects and experimentation matter for leadership growth (32:21)
• How Prashant’s personal projects enhance technical credibility & leadership skills (36:59)
• Rapid fire questions (37:57)

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

AI is reshaping the fundamental economics of startups—lowering product development costs, compressing GTM cycles, and rewriting the rules of competition. In this episode, Craig McLuckie (Co-Founder & CEO @ Stacklok, co-creator of Kubernetes) unpacks “the epoch of the startup,” a moment of massive disruption where fast-moving founders have a unique edge over incumbents. We explore how Craig is navigating this new era from rethinking cost structure, value capture, and defensibility to leveraging open-source, community, and asymmetric advantages as core pillars of Stacklok’s strategy. Craig shares lessons from pivotal product shifts, frameworks for identifying moats, and the broader societal implications of AI-driven disruption. Whether you’re leading a startup, pivoting in the face of AI, or thinking about your next big move, this conversation offers a strategic playbook for thriving in today’s shifting landscape.

Craig is the CEO and co-founder of Stacklok, where his team is working to tip AI code generation on its side, from vertical, closed solutions to horizontal, aligned systems. Craig was previously CEO and co-founder of Heptio, which was acquired by VMware in 2018; he has also led product and engineering teams at Google and Microsoft. Craig is a co-creator of Kubernetes and he bootstrapped and chaired the Cloud Native Computing Foundation. x

For over 30 years, Side has helped create unforgettable user experiences—from indies to AAA blockbusters like Silent Hill 2 and Baldur’s Gate 3.

• Why this moment is “the epoch of the startup” (2:03)
• How AI shifts startup economics: from cost structures to value capture (4:18)
• Why incumbents struggle during disruption—and how startups can win (8:17)
• The origin story behind Stacklok & lessons from Craig’s pivot (11:04)
• Frameworks for identifying asymmetric advantages as a founder (14:48)
• How to map your unique asymmetric advantages to new opportunities and secure stakeholder buy-in (16:34)
• Rethinking defensibility & value capture in the AI era (16:29)
• How Craig applied cost, GTM & product perspectives to strategic pivots @ Stacklok (18:07)
• Building investment theses: Aligning cultural strengths & asymmetric advantages with evolving opportunities (20:05)
• Determining your startup’s investment themes (22:53)
• Structuring experiments & validating opportunities (24:15)
• Defensibility & building community-driven moats in early ideation phases (26:54)
• Signals of early community-product alignment (31:24)
• Conversation frameworks to assess asymmetric advantages (32:22)
• Societal implications of AI disruption & the “startup epoch” (35:14)
• Rapid fire questions (38:12)

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/