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EPISODE · Jun 9, 2026 · 1H

Stop doing math, becoming a leader, and the future of AI agents

from How NOT To Build: Startup Stories | A Jemini Podcast · host Dan Villa

On this episode I got to catch up with my long time friend Rob Oesch, the Director of Product Management at Kaseware.In this episode we coverWhy you need to stop doing math with your startupPractical advice for when you transition into a leadership role on your existing teamAnd what it’s going to look like when you replace your employees with AI agentsAt Kaseware, Rob delivers a premier investigative platform for Law Enforcement, Corporate Security, and Intelligence Analysts.I hope you enjoy, Episode 23 of How NOT to Build.00:00 Introduction to the Podcast and Its Purpose02:33 The Prototype Mindset and Building Products05:22 Navigating the Zero to One Challenge07:45 The Importance of Client Relationships10:16 Lessons from Leadership and Boundaries12:49 The Intersection of Law Enforcement and Technology15:34 Open Source Intelligence and Its Evolution18:20 Building Products for Niche Markets20:38 Leadership Styles and Communication23:19 The Balance of Grace and Decisiveness in Leadership25:59 Transitioning to Axon and Future Endeavors30:26 Transitioning to Axon: A New Beginning31:18 Growth and Scaling: From Zero to One34:05 Navigating Challenges in a Fast-Paced Environment36:16 Adapting to Change: Lessons from Government to Tech38:46 The Side Hustle Mentality: Balancing Passion and Work41:53 Introducing Kaseware: A New Venture46:50 Challenges and Opportunities in AI Integration51:10 The Future of AI in the Workplace55:58 Reflections on Technology and Human Connection

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