How do you know when your community is fueling your growth or when it’s quietly working against you? In this episode, I sit down with Ryan Hamilton, author of The Growth Dilemma, to unpack the hidden dynamics of communities and client segments. Ryan shares fascinating research and real-world stories that reveal why growth isn’t just about gaining more customers. It’s about managing the relationships between them. We explore how brands can scale in a way that sparks connection, avoids conflict, and builds exponential value.

From Nike to Carhartt to professional services firms, we dig into the practical and sometimes surprising lessons leaders can apply across industries. We also discuss the four relationship types that exist within every client base and why recognizing them can make or break your growth strategy. If you’ve ever wondered why some communities thrive while others implode, this conversation will give you the insight (and the courage) to approach growth differently.

Topics We Cover in This Episode:

• Why traditional customer growth strategies leave hidden risks on the table

• How separate vs. connected communities can completely change your outcomes

• The one factor that turns leaders into magnets for followers (and what happens when you lose it)

• Why not every client mix is healthy and the danger of drifting into incompatibility

• A surprising “matrix” tool that helps you map out community dynamics

• How small, intentional moves can unlock exponential connections

• The unseen ways conflicts inside a community can erode your brand

• What brands like Nike, Carhartt, and Supreme teach us about scaling without losing credibility

Ready to rethink growth? Tune in now and discover how to identify the communities you’re really building and how to align them for long-term success. And if you found value in this conversation, don’t forget to share the episode and leave a review so more people can discover the insights inside The Growth Dilemma.

Resources Mentioned:

Order your copy of Give to Grow

Get the Supplemental materials for Give to Grow

Get a copy of your GrowBIG Playbook today!

Connect with Ryan on LinkedIn

Connect with Annie on LinkedIn

What does it really mean to lead with respect and how can it transform the way we work, connect, and grow? In this episode, I sit down with Marcy Syms, trailblazing business leader, author of Leading with Respect, and former president of the New York Stock Exchange. Marcy shares how respect goes far beyond a “soft skill” and becomes the foundation for trust, productivity, and lasting relationships. Together, we explore how empathy, compassion, and authenticity weave into leadership and why these qualities are essential to success in both business and life.

We also dig into Marcy’s experience building Syms into a nationally recognized retailer, her innovative approach to hiring and training, and the intentional choices she made to buck industry trends by putting people and values first. Her stories and insights reveal how respect shows up in the smallest details, like eye contact, listening, follow-through, and in the biggest decisions that define culture and legacy.

Topics We Cover in This Episode:

• Why respect is the ultimate driver of productivity

• The role of empathy vs. compassion in authentic leadership

• How rethinking “salespeople” as “educators” transformed a retail giant

• The surprising power of going against industry norms

• A hiring test that reveals if someone is “selfish or other-ish”

• The leadership principle Marcy never compromises on

• How reading the room can shape influence and connection

• What Marcy looks for when choosing who to work with

If today’s conversation with Marcy inspired you, don’t stop here. Grab a copy of her book Leading with Respect and explore how these timeless lessons can reshape your approach to leadership, relationships, and results. You can also connect with Marcy directly at marcysyms.com or on LinkedIn. And if you enjoyed this episode, the best way to support the show is to leave a short and thoughtful review. It only takes a moment, but it helps more people discover these conversations.

Resources Mentioned:

Order your copy of Give to Grow

Get the Supplemental materials for Give to Grow

Get a copy of your GrowBIG Playbook today!

Grab a Copy of Marcy’s Book

Check Out Marcy’s Website

Connect with Marcy on LinkedIn

What makes work truly worth it? Is it the paycheck, the prestige, or the purpose behind what we do every day?

In this episode, I sit down with authors Christopher Wong Michaelson and Jen Tosti-Kharas to dive into their book Is Your Work Worth It? We unpack the big questions around why we work, what keeps us going long after we “have to,” and how to think differently about love versus money in our careers. From rethinking autopilot routines to exploring how work shapes our legacy, this conversation will have you reflecting on your own motivations in a whole new way.

Together, we also explore the tension between career demands and personal life, the myths about turning passions into professions, and how leaders can shape meaningful work for others. Whether you’re building a business, leading a team, or simply wondering what your next career move should look like, this episode offers fresh perspective on finding fulfillment and redefining success.

Topics We Cover in This Episode:

• The surprising truth about why most people really keep working

• Why “autopilot” is the hidden enemy of career satisfaction

• A simple way to test if your work passes the “seven-year-old” explanation test

• The overlooked connection between love, money, and fairness at work

• What entrepreneurs often love most about their work (and it’s not what you think)

• How to use “seasons of life” to plan your career with more intention

• Why the most worthy work is often undervalued—and what to do about it

• A framework to uncover your deeper purpose that goes beyond surface-level goals

Ready to rethink your relationship with work? Tune in now and walk away with new questions to ask yourself, your team, and your organization. And if this episode sparks something for you, share it with a colleague or friend because these are conversations worth having.

Resources Mentioned:

Order your copy of Give to Grow

Get the Supplemental materials for Give to Grow

Get a copy of your GrowBIG Playbook today!

Connect with Christoper

Connect with Jen