In this episode of Beneath the Transaction, Chris sits down with Vanessa Plant, Executive Director of the Alku Foundation and an experienced leader in Boston’s nonprofit and philanthropic space.

Vanessa has spent her career helping organizations move beyond traditional, transactional approaches to fundraising and into more relational, trust-based models of giving. Her work centers on building authentic partnerships, strengthening organizational culture, and creating lasting community impact.

Together, Chris and Vanessa explore what it looks like to move beneath the transaction in philanthropy—shifting from control and metrics to trust, relationship, and shared purpose. They discuss the principles of trust-based philanthropy, the role culture plays in nonprofit effectiveness, and why meaningful impact begins with how we choose to relate to the people we serve and support.

At its core, this conversation is about more than giving. It’s about the kind of leadership required to build trust, foster connection, and create change that lasts.

Because when philanthropy becomes relational, impact becomes transformational.

CHAPTERS

00:00 Introduction to Beneath the Transaction Podcast 01:45 Exploring Philanthropy: Intent vs. Transaction 04:19 Historical Context of Philanthropy 09:04 The Transactional Nature of Fundraising 12:05 Trust-Based Philanthropy: A New Approach 18:29 Power Dynamics and Fears in Philanthropy 25:36 Helping Organizations Find Their Own Answers 30:13 The Importance of Culture in Nonprofits 33:35 Investing in Culture and Human Connection 39:12 The Importance of Employee Retention and Culture 41:09 The Soil of Organizations: Culture vs. Outcomes 46:41 Building Authentic Relationships in Philanthropy 51:00 Leveraging Influence Capital for Community Impact 55:25 The Power of In-Person Connections 01:01:05 Authenticity as a Key to Meaningful Relationships

In this episode of Beneath the Transaction, Chris and Kenzie explore the role purpose plays in real transformation—both in our leadership and in our lives. Too often we focus on achievement and external success, but lasting transformation begins when we slow down long enough to ask deeper questions about who we are becoming and why we do what we do.

Joining the conversation is H Hassan, who has spent more than 21 years serving in public safety. Throughout his career, H has taken on a variety of roles, including training and developing law enforcement professionals and helping officers strengthen both their physical and mental readiness. He currently serves as a Firearms Training Coordinator, where he brings together discipline, leadership, and mentorship to help others grow in demanding environments.

In this conversation, H reflects on his own leadership journey and the impact of discovering and defining his “why.” Together, Chris, Kenzie, and H talk about the difference between surface-level change and true transformation, the role intentionality and commitment play in personal growth, and what it means to live and lead beneath the transaction.

At the heart of the episode is a powerful idea: purpose is the mortar of transformation. When purpose becomes clear, leadership moves beyond achievement and into the deeper work of becoming.

In this episode of Beneath the Transaction, Chris sits down with Olivia Hickerson, founder of EmpowerTactics, to explore the often unseen work of creating psychologically safe organizations.

Olivia has spent her career helping mission-driven organizations strengthen the systems behind their impact — from governance and organizational infrastructure to the cultures that shape how people show up at work. Her work focuses on translating values into structure so that culture isn’t left to chance.

Together, Chris and Olivia explore why psychological safety is not simply a leadership buzzword but a daily leadership responsibility. They discuss the unique pressures nonprofit leaders face, the emotional weight of mission-driven work, and how burnout often grows in environments where safety and support are lacking.

The conversation also unpacks the complex dynamics between executive leaders and boards, the courage required for vulnerable leadership, and how small, intentional actions can transform the environments people work in every day.

At its heart, this episode is about leadership posture — the way leaders show up, listen, and create space for others to thrive.

Because the cultures we build aren’t accidental. They’re shaped by the environments we intentionally create.

Key Themes in This Episode:

• Why psychological safety is foundational to healthy leadership

• The hidden burnout dynamics inside mission-driven organizations

• The relationship between board leadership and organizational culture

• How vulnerability strengthens leadership rather than weakening it

• Small leadership actions that create meaningful cultural change

• Why intentional structure protects culture from becoming accidental.

Guest Introduction:

Olivia Hickerson is the founder of EmpowerTactics, where she partners with mission-driven organizations to strengthen the systems behind their impact. She specializes in organizational infrastructure, governance clarity, and psychologically safe workplaces, helping teams move from reactive problem solving to intentional design.

Olivia is known for bringing steady strategy, thoughtful challenge, and practical clarity to complex leadership environments.

🎙️ Listen to the full conversation on Beneath the Transaction, and follow the show for more weekly conversations about life, leadership, and the work happening beneath the surface.

Chapters

00:00 Introduction to Psychological Safety 02:22 Olivia's Journey in Nonprofit Leadership 05:55 Experiencing Burnout in Nonprofit Work 12:32 Navigating Board Dynamics and Leadership Challenges 22:49 Creating Safe Spaces in Leadership 28:40 The Importance of Sequence in Organizational Culture 30:01 The Power of Vulnerability 32:28 Creating Safe Spaces in Leadership 35:19 Building Relationships with Board Members 39:05 The Ripple Effect of Change 52:04 Transformational Leadership and Human Connection