Building the Future with Agentic AI: A Conversation with Yaakov Sash of Casso AI

In the AI Risk Reward podcast, our host, Alec Crawford (@alec06830), Founder and CEO of Artificial Intelligence Risk, Inc. aicrisk.com, interviews guests about balancing the risk and reward of Artificial Intelligence for you, your business, and society as a whole. Podcast production and sound engineering by Troutman Street Audio. You can find them on LinkedIn.In this episode, Alec welcomes Yaakov Sash, Founder and CEO of Casso AI, for an in-depth conversation about the evolving intersection of AI, finance, and enterprise technology. Yaakov shares insights from his extensive background in banking and digital asset technology, recounting his journey through major financial institutions and the genesis of Casso AI. He explains the concepts of “vibe coding” and “vibe crafting,” highlighting the growing need for structured AI-driven development in enterprise settings. The discussion covers the impact of AI on traditional software roles and the shifting requirements for computer science graduates, as well as the ethical considerations and risks of advanced AI systems. Alec and Yaakov also touch on influential thinkers such as Ray Kurzweil and Eliezer Yudkowsky, and conclude with a lightning round covering everything from Brooklyn pizza to the enduring value of software design principles.Summary:Career Evolution: Yaakov Sash shares his trajectory from major banks to founding Casso AI, emphasizing adaptability and industry cycles.Vibe Coding vs. Crafting: The episode details the transition from rapid AI-generated app development to thoughtful, specification-driven enterprise solutions.AI’s Workforce Impact: Yaakov discusses the changing role of developers, predicting a shift toward orchestrating and reviewing AI-generated code.Ethical and Safety Concerns: The conversation explores the risks of AI deception, safety in development, and the importance of maintaining oversight.Founders’ Mindset: Building enduring value and pivoting with purpose is highlighted as key advice for entrepreneurs navigating emerging technologies.Companies/Organizations:Casso AIArtificial Intelligence Risk, Inc.Credit SuisseUBSMerrill LynchBank of AmericaJPMCCircleMicrosoftOpenAI (Codex)Anthropic (Claude)Books:The Singularity Is Near by Ray KurzweilThe Singularity Is Nearer by Ray KurzweilWorks by Eliezer YudkowskyWorks by Ray BradburyMovies:SpeedCopyright © 2025 by Artificial Intelligence Risk, Inc.