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Calm and Confident Leader Podcast

S3 - Episode 28 - Compassion and Clarity - Cal Riley

07 Oct 2025

Description

What if being "too compassionate" is actually the most profitable thing you could do as a leader?Most entrepreneurs think compassion makes you weak. That caring too much about your team means lower standards, missed goals, and a business that runs you instead of the other way around. But what if that's completely backwards?In this episode, host Jason Stonehouse sits down with Cal Riley, combat veteran, entrepreneur, leadership coach, and author of Entrepreneurial Compassion: An Entrepreneur's Journey Through Combat, Suicide, and the Discovery of Compassionate Leadership. Cal is on a mission to develop 1 million compassionate leaders by 2035 and prevent 100,000 suicides by helping leaders build healthier companies and more humane systems.Cal challenges the biggest myths about compassionate leadership, including why tolerating poor performance isn't compassionate at all, how the most driven entrepreneurs can pair their intensity with compassion to get better results, and why your team matters more than your clients. He shares why apologizing might be the most underrated leadership skill, how systems like EOS work best when leaders do their inner work first, and practical steps any leader can take today to build more self-awareness and show up better for their team.This conversation gets real about the mirror every entrepreneur faces and what it takes to become the kind of leader people actually want to work for.Resources mentioned:CalRiley.com for a free self-assessment surveyEntrepreneurial Compassion (all proceeds go to Stop Soldier Suicide)JasonStonehouse.com for free leadership resources and coaching infoTotalPackagePlaybook.com to learn how to bring your whole self to your workIf this episode challenged how you think about leadership, subscribe to the Calm and Confident Leader podcast, share it with another entrepreneur who needs to hear this, and leave a like. Life is a process, so don't do it alone.

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