Jonathan Lowenhar of Enjoy The Work joins the Grit Daily Startup Show to get real about the moment every successful founder dreads — when the job changes from building the product to building the company. He breaks down why most first-time CEOs feel like imposters, how to pick the right path for your business, and why enjoying the grind is the ultimate competitive edge. If you’ve ever thought, “Am I even doing this right?” this episode is your new playbook.

Jonathan Lowenhar of Enjoy The Work joins the Grit Daily Startup Show to get real about the moment every successful founder dreads &mdash; when the job changes from building the product to building the company. He breaks down why most first-time CEOs feel like imposters, how to pick the right path for your business, and why enjoying the grind is the ultimate competitive edge. If you&rsquo;ve ever thought, &ldquo;Am I even doing this right?&rdquo; this episode is your new playbook.

Grit Daily Startup Show podcast explores the world of entrepreneurship, founders, and CEOs to talk scaleups and startups, from conception and funding to exits. Interviews run across all industries, with entrepreneurs sharing their best decisions, mistakes to avoid, and wildest entrepreneurial stories. With single-guest entrepreneur and multi-guest formats.

Grit Daily Startup Show podcast explores the world of entrepreneurship, founders, and CEOs to talk scaleups and startups, from conception and funding to exits. Interviews run across all industries, with entrepreneurs sharing their best decisions, mistakes to avoid, and wildest entrepreneurial stories. With single-guest entrepreneur and multi-guest formats.

Startup Show, brought to you by the premiere startup news hub, Grit Daily

Grit Daily Startup Show

Jonathan Lowenhar and the Art of Building Great CEOs

Tony Pinedo shares how leading inside a youth correctional facility reshaped his understanding of leadership, trust, and human potential. Drawing from decades of experience, he explains why empathy, non-judgmental curiosity, and intentional presence are the true foundations of influence. This conversation explores how integrating values across work and life can transform culture, performance, and personal fulfillment.

Tony Pinedo shares how leading inside a youth correctional facility reshaped his understanding of leadership, trust, and human potential. Drawing from decades of experience, he explains why empathy, non-judgmental curiosity, and intentional presence are the true foundations of influence. This conversation explores how integrating values across work and life can transform culture, performance, and personal fulfillment.

Tony Pinedo’s Case for Empathy as the Ultimate Leadership Skill

Phillip Lanos and Sharon Wood explore the intersection of gaming, family connections, and memory enhancement. Sharon shares her journey from marketing in the gaming industry to creating products that foster joy and dignity for individuals with fading memories. They discuss the importance of relationships, the science behind gaming, and the innovative approaches being taken to enhance quality of life through interactive experiences. The conversation emphasizes the need for cross-generational connections and the potential of technology to bring families closer together.

Connect with Sharon Wood: 
https://happypeoplegames.com

Phillip Lanos and Sharon Wood explore the intersection of gaming, family connections, and memory enhancement. Sharon shares her journey from marketing in the gaming industry to creating products that foster joy and dignity for individuals with fading memories. They discuss the importance of relationships, the science behind gaming, and the innovative approaches being taken to enhance quality of life through interactive experiences. The conversation emphasizes the need for cross-generational connections and the potential of technology to bring families closer together.
Connect with Sharon Wood:&nbsp; <a href="https://happypeoplegames.com">https://happypeoplegames.com</a>

From Grand Theft Auto to Grandparents: Sharon Wood’s Mission for Joy

Greg Whalen, CTO of Prove AI, explains why many enterprises are stalling with generative AI by treating it like traditional software and postponing the hard parts like observability, debugging, and governance. He breaks down what “observability” actually means in AI systems, why outcome-based metrics matter more than chasing black-box explanations, and how Prove AI helps teams collect the right telemetry to reach production safely. The conversation also explores agentic workflows, human oversight, and why technical leaders need to change how their organizations operate if they want gen AI to deliver real value.

Greg Whalen, CTO of Prove AI, explains why many enterprises are stalling with generative AI by treating it like traditional software and postponing the hard parts like observability, debugging, and governance. He breaks down what &ldquo;observability&rdquo; actually means in AI systems, why outcome-based metrics matter more than chasing black-box explanations, and how Prove AI helps teams collect the right telemetry to reach production safely. The conversation also explores agentic workflows, human oversight, and why technical leaders need to change how their organizations operate if they want gen AI to deliver real value.

Jonathan Lowenhar and the Art of Building Great CEOs

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