Claim OwnershipAround with Randall
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© All materials Copyright Hallett Philanthropy 2020
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Listen to the weekly podcast “Around with Randall” as he discusses, in just a few minutes, a topic surrounding non-profit philanthropy. Included each week are tactical suggestions listeners can use immediately to make their non-profit, and their job activities, more effective.
Email Randall with a topic for a show: podcast@hallettphilanthropy.com
Email Randall with a thought regarding specific a show: reeks@hallettphilanthropy.com
281 Episodes
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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.
Donor salons are small, intimate gatherings designed to deepen relationships without asking for money. If you focus on conversation, curiosity, and shared values, you spark authentic engagement that leads to stronger long-term giving. These experiences feel exclusive, personal, and meaningful, more powerful than email, phone calls, or large fundraising events. When executed with purpose, thoughtful hosting, and timely follow-up, salons become a fast track to trust, insight, and transformational philanthropy.
One-time stories inspire emotion; longitudinal stories build transformation. The most successful fundraisers don’t just tell what happened, they connect the dots over time, showing progress, growth, and real impact. When donors see themselves within the story—woven into its chapters—they move from giving out of urgency to giving out of identity. Storytelling isn’t about communication; it is communication. And when done longitudinally, it becomes the foundation for trust, loyalty, and transformational giving.
Annual giving programs across every sector are struggling—and the old tactics no longer work. To re-engage donors, fundraisers must borrow from behavioral economics: reduce friction, offer clear defaults, and frame choices that inspire action. Subtle “nudges,” simplified giving options, and immediate impact stories can transform inertia into generosity. In a noisy, overloaded world, the organizations that understand how people actually make giving decisions will be the ones that thrive.
Great boards don’t just meet—they measure. When boards track their own performance, they shift from opinion-driven debate to data-informed decisions. Transparent metrics build trust, align strategy, and keep every member accountable to the mission. Start small, stay consistent, and let dashboards reveal where progress is thriving—and where course correction is needed. The result? A more engaged, effective board that owns its success.
In today’s digital world, one false post can damage a nonprofit’s reputation faster than any press release can repair it. False information spreads up to six times faster than truth—and small organizations often lack the resources to respond effectively. The key is preparation: monitor social platforms, respond calmly and transparently, and have a crisis protocol ready before misinformation strikes. Rebuilding trust takes time, but protecting it starts with awareness, clarity, and steady leadership. Don’t wait for a storm—build your umbrella now.
Nonprofits often face a silent crisis: they can’t fund the very infrastructure that keeps their mission alive. While donors love to support visible programs, few realize that unrestricted gifts – the ones that cover salaries, compliance, and basic operations – are what make real impact possible. When organizations underfund their “overhead,” they enter a starvation cycle that weakens long-term sustainability. By reframing unrestricted giving as mission fuel, nonprofits can help donors see that trust, not just passion, drives meaningful change. Restricted gifts show commitment. Unrestricted gifts show belief in leadership.
Nonprofits must learn to meet Millennials and Gen Z where they live—online, mobile, and driven by values. These generations demand immediacy, authenticity, and easy digital giving experiences, from QR codes to Apple Pay to thank-yous turned in 24-hours. Their gifts may start small, but their potential as future major donors is enormous if organizations invest in them now. The future of philanthropy belongs to those willing to adapt, engage, and make giving effortless.
Nonprofits can’t afford to ignore mental wellness. Stretching employees too thin leads to burnout, turnover, and lost donor trust—costs that ripple across mission, fundraising, and community impact. Leaders who invest in staff well-being not only do the right thing but also protect retention, efficiency, and donor relationships. From normalizing mental health conversations to flexible workspaces and empathetic leadership, the path is clear: taking care of your team is both a moral and strategic imperative.
Once seen as an invasion of privacy, texting is now one of the most effective tools for donor engagement. With open rates as high as 98%, texts dramatically outperform email and can strengthen relationships when used thoughtfully for outreach, stewardship, and even giving. The key is to keep messages short, timely, and personal—never spammy. When done well, texting becomes another arrow in the quiver of fundraising, deepening impact and building authentic connections in a digital-first world.
Getting in front of new prospects is harder than ever—but sitting back and waiting isn’t an option. This episode introduces a creative solution: gamifying the dreaded phone call. By turning outreach and even rejection into a points-based game, fundraisers can build camaraderie, reduce fear, and spark real momentum. From scoring voicemails to celebrating “rejection of the week,” this approach reframes calling from a chore into a challenge and makes progress fun again.
Donor conversations aren’t always smooth - especially when political or social issues enter the mix. In this podcast, Randall Hallett unpacks how fundraisers can navigate divisive topics with civility, professionalism, and focus on shared values. He stresses the importance of staying agnostic, listening first, and reframing discussions around mission and impact rather than ideology. With practical communication strategies and a reminder that philanthropy is about hope and connection, Randall shows how to keep relationships strong, even when opinions differ.
Building a strong donor portfolio isn’t magic. It’s math, persistence, and mindset. In this piece, we break down the real metrics behind qualification calls, revealing how many dials it takes to land conversations and turn those into meaningful meetings. It’s not just about picking up the phone, but about embracing follow-ups, leveraging multiple channels, and tracking every step. Success comes from resilience, consistency, and understanding that small wins compound into lasting donor relationships.
Transformational philanthropy doesn’t happen overnight—it’s the result of patience, humility, and deep trust built over years. Too often, organizations focus on immediate needs and campaign timelines instead of donors’ passions and timeframes. This story highlights how a client took the long view, nurturing a relationship with one of the rare 0.1% capable of extraordinary giving. By personalizing stewardship, showing appreciation, and listening with humility, they created space for generosity to grow naturally into something truly transformative.
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