The title “Chief Philanthropy Officer” doesn’t fully capture the real job, because much of the role is political, relational, and deeply strategic. CPO's navigate power dynamics, align competing priorities, translate donor realities, and build trust across the organization. Success isn’t about control or title; it’s about influence, diplomacy, and internal partnerships. When CPO's educate simply, make invisible work visible, invite leaders into the process, and stay calm under pressure, alignment follows. The result is stronger internal cohesion and better outcomes for donors.

Adversity isn’t a pause for nonprofits - it’s a pivot point. As we head into 2026, organizations facing leadership turnover, donor fatigue, staffing gaps, and revenue volatility must decide whether to act, watch, or wonder what happened. This episode reframes adversity as a moment for honest assessment, disciplined focus, and intentional adjustment. Progress doesn’t come from busyness or optimism—it comes from clarity, choices, and the willingness to engage discomfort. The organizations that emerge stronger will be the ones that choose action.

Planned giving won’t grow if we keep rewarding gift officers as if it doesn’t exist. When incentives focus only on cash and pledges, we unintentionally steer MGO’s away from the very conversations that unlock transformational wealth. This episode tackles the internal challenge head-on: how nonprofits can count planned gifts (without violating accounting rules) in ways that motivate the right behaviors. Change the incentives, and you change the outcomes.

Uncertainty has become the backdrop of modern philanthropy. Volatile markets, shifting interest rates, political noise, and a massive transfer of wealth all colliding at once. In moments like these, donors aren’t pulling away from generosity; they’re searching for it. Clarity, flexibility, and reassurance. Planned and estate giving offers exactly that: options to solve real concerns while aligning deeply held values with long-term impact. The real opportunity isn’t about asking for money, it’s about helping donors make confident decisions in uncertain times. For nonprofits willing to lead with curiosity and care, this moment may define the next decade of transformational giving.

It’s time once again for Randall’s highly anticipated yearly predictions. As many know, the nonprofit landscape in 2026 won’t be defined by doing more, it will be defined by doing different. As donor bases continue to shrink, a smaller group of donors will drive a larger share of giving, forcing organizations to rethink cultivation, stewardship, and board engagement. Donor-advised funds, non-cash gifts, and accelerated planned giving will reshape how generosity flows, while AI moves from novelty to necessity in forecasting and stewardship. In 2026, one thing is clear: waiting is no longer a strategy. The nonprofits that win in 2026 will be the ones planning now, with intention and courage.

Looking back on 2025, the real story isn’t which predictions landed, it’s what they exposed about modern philanthropy. Strong markets and record giving mean a deeper shift: fewer donors, rising inequality, and growing dependence on a shrinking pool of major and mega givers. Donor-advised funds surged, AI gained traction, and consolidation quietly accelerated. The year proved philanthropy isn’t failing—but it is becoming more concentrated, more strategic, and less forgiving of organizations without a plan.

Should a nonprofit create its own foundation? The answer is surprisingly simple and at the same time, relentlessly hard: will it raise more money? Foundations only make sense when organizational complexity, donor access, privacy, or governance limitations are actively holding philanthropy back. Done well, a foundation creates focus, opens doors, and frees leadership to pursue deeper donor relationships. Done poorly (or too early) it adds cost, confusion, and duplication without impact.

Endowments are the engine that keeps nonprofits strong—not just today, but decades from now. Yet, the fine print matters: overly restrictive funds can choke impact, while flexible quasi-endowments help organizations adapt as needs and missions evolve. The key is striking a balance between donor intent and long-term usefulness. Smart documentation, thoughtful donor conversations, and mission-aligned flexibility turn endowments into a powerhouse for stability, innovation, and generational impact. When we build wisely, we protect our mission, our donors, and the future we serve.

The greatest opportunity in philanthropy today isn’t just the transfer of wealth, it’s the transfer of values across generations. With trillions set to move from silent, high-capacity families into foundations and DAFs, nonprofits must build relationships that go far beyond the matriarch and patriarch. The organizations that thrive will be the ones mapping families, engaging heirs early, personalizing communication, and becoming trusted conveners of multi-generational giving conversations. When done well, you don’t just secure a gift, you become part of a family’s story for decades.

Gratitude isn’t just a warm feeling, it’s a physiological, psychological, and relational reaction that reshapes how we live and lead. Research proves that it lowers stress, improves heart health, helps with sleep, and strengthens resilience. Yet, we rarely slow down long enough to notice its impact. Thanksgiving gives us permission to pause, but the real transformation comes when we choose gratitude intentionally, not seasonally. When we shift from “what’s happening to me” to “how do I respond,” our relationships deepen, work sharpens, and our well-being expands. If you give yourself a few quiet moments this week to reflect, you may walk away clearer, calmer, and more connected.