Overview
In this episode, Jacob sits down with Greg Montgomery to explore an often-overlooked leadership skill: love. Together, they unpack why genuine one-on-one connections matter more than scalable systems, how fulfillment differs from fleeting happiness, and what intentional leadership looks like in practice. Greg shares formative experiences—from influential ideas by Stephen R. Covey to lessons from Ed Mylett—that reshaped how he shows up at work and in life. This conversation is especially relevant for leaders who want stronger cultures without losing their humanity.
What we cover
* Why love belongs in leadership conversations – exploring why care, empathy, and genuine concern aren’t “soft extras,” but foundational to trust, influence, and long-term impact at work.
* The limits of scalability in human relationships – why the most meaningful leadership moments can’t be automated, outsourced, or multiplied without loss, and why one-on-one presence still matters.
* Love as a verb, not a feeling – unpacking the idea (inspired by Stephen R. Covey) that love is something you do through consistent actions, sacrifice, and attention—not something you passively feel.
* Happiness vs. fulfillment – distinguishing between short-term happiness driven by money, success, or status, and the deeper fulfillment that comes from connection, service, and meaning.
* Vulnerability as a leadership strength – why openness and emotional honesty build credibility and psychological safety rather than undermining authority.
* How intentional one-on-ones actually work – reframing one-on-one meetings as relationship-building time rather than tactical checklists, and why this shift changes team dynamics.
* Feeling seen at work – a story of how simple appreciation and acknowledgment from a leader can fundamentally change motivation, loyalty, and confidence.
* The business impact of human-centered leadership – why investing in people, culture, and connection ultimately shows up in retention, customer experience, and financial outcomes.
* Men, identity, and inner work – discussing why many men struggle with fulfillment despite external success, and the importance of creating space to reflect, reset, and reconnect.
* Creating environments for transformation – Greg’s vision for The Shift retreat and why intentional experiences can catalyze lasting personal and professional change.
Time-stamped outline
* 00:00 – Intro and first-time podcast nerves
* 01:14 – Greg’s background and winding career path
* 03:30 – Why Jacob associates leadership with love and one-on-one connection
* 04:19 – Stephen R. Covey, love as a verb, and early mindset shifts
* 06:45 – Ed Mylett, fulfillment, and the role of vulnerability
* 09:30 – Building relationships through intentional leadership
* 11:55 – A manager who modeled genuine care at work
* 14:58 – Gary Vee, Chief Heart Officers, and culture at scale
* 18:00 – The Shift Retreat and creating space for transformation
* 21:37 – Closing reflections on love-driven leadership
