Will Cady, founder of HEAL MVMNT and former Reddit creative strategist, joins the show to explore why technology is advancing faster than the moral frameworks needed to guide it. He explains how his organization helps leaders align community, culture, and purpose so companies can scale without losing their humanity. Cady also shares why keeping a “human in the loop” is essential in the AI era and how defining a clear north star enables businesses to grow with intention rather than drift off course.

Will Cady, founder of HEAL MVMNT and former Reddit creative strategist, joins the show to explore why technology is advancing faster than the moral frameworks needed to guide it. He explains how his organization helps leaders align community, culture, and purpose so companies can scale without losing their humanity. Cady also shares why keeping a &ldquo;human in the loop&rdquo; is essential in the AI era and how defining a clear north star enables businesses to grow with intention rather than drift off course.

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

Will Cady Is Building a Framework for Leadership in an Age Where Technology Outpaces Morality

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.

Greg Whalen Thinks Enterprises Are Making One Big Mistake With Generative AI

Van Camp and Carlson join Phillip Lanos to unpack the moment when fast-growing businesses outgrow basic tax prep and start needing real cash flow visibility, risk strategy, and proactive advisory support. They break down why many CPAs default to familiar year-end moves, how liquidity becomes a hidden failure point, and what owners should look for in an advisory team as complexity rises. The conversation also introduces 831B structures as a framework for enterprise risk management, and explains how the right planning mindset can help protect both what a company has built and what it is trying to become.

Van Camp and Carlson join Phillip Lanos to unpack the moment when fast-growing businesses outgrow basic tax prep and start needing real cash flow visibility, risk strategy, and proactive advisory support. They break down why many CPAs default to familiar year-end moves, how liquidity becomes a hidden failure point, and what owners should look for in an advisory team as complexity rises. The conversation also introduces 831B structures as a framework for enterprise risk management, and explains how the right planning mindset can help protect both what a company has built and what it is trying to become.

When Growth Outruns the CPA Playbook, Brian Van Camp and Van Carlson Step In

This episode spotlights Himanshu Rathore, the operations leader behind Teleperformance Thailand’s remarkable rise as a global talent hub. Listeners will hear how people-first leadership, multicultural collaboration, and crisis-tested resilience shaped one of the company’s strongest success stories. It is a compelling look at what modern operational excellence truly requires.

This episode spotlights Himanshu Rathore, the operations leader behind Teleperformance Thailand&rsquo;s remarkable rise as a global talent hub. Listeners will hear how people-first leadership, multicultural collaboration, and crisis-tested resilience shaped one of the company&rsquo;s strongest success stories. It is a compelling look at what modern operational excellence truly requires.

Will Cady Is Building a Framework for Leadership in an Age Where Technology Outpaces Morality

Grit Daily Startup Show

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