Dag Kittlaus is the CEO and co-founder of Riva Health, a company that has set out to revolutionize how patients manage hypertension and heart disease. We discuss the innovation behind Riva, which turns a smartphone into a health management assistant that collects data and connects patients with a proactive care team. Hearing Dag talk, you can see how this might extend into traditional assistant functionality for managing chronic heart conditions. He breaks down the Riva journey thus far and we go back into his history as a co-founder of Siri (acquired by Apple) and Viv Labs (acquired by Samsung) and what he learned along the way about assistants, technology, and how users interact with novel solutions.  We also go into depth on the rise of generative AI and ChatGPT. From a ChatGPT perspective, we spent considerable time discussing the new Plugins model to integrate third-party services. Kittlaus was doing this for the Siri app 15 years ago before the Apple acquisition. He did it again with Viv Labs and Samsung's Bixby assistant and knows the challenges of creating a plugin ecosystem. His observation is that the problems are largely the same and OpenAI is in for a rude awakening. I am sure you will enjoy this wide-ranging discussion about innovation, technology adoption, and overcoming barriers to growth with someone that has been influential in shaping our views, experiences, and assumptions about intelligent assistants of all kinds.