Around with Randall

Too many fundraising shops operate in silos, each department focusing solely on its own priorities. This separation creates friction—between donor communications, programming, events, and stewardship—hurting both efficiency and donor experience. A truly successful fundraising operation breaks down these walls and works collaboratively across teams. When everyone aligns around donor impact, not jus...

Fear is natural—but in fundraising, it's often the silent barrier to real relationship-building. Whether it's a new gift officer hesitating to make a thank-you call or a seasoned professional dreading the ask, fear can shrink our actions and paralyze our potential. But reframing these moments as invitations, not transactions, changes everything. This episode explores how small shifts in language a...

What if everything we know about building donor relationships is backward? In this episode, we flip the script—looking at fundraising not from the fundraiser's lens, but from the donor's experience. From curiosity to trust to continuity, we explore the eight emotional stages a donor navigates before and after making a gift. When you understand how donors feel at every step, you unlock deeper relat...

When crisis hits—whether it's a struggling department or the entire organization—your response defines your future. This episode explores how to talk about financial distress without sounding desperate, and how to frame fundraising efforts as strategic, not survivalist. The difference? Donors don’t want to save a sinking ship—they want to fuel a mission with momentum. If you can communicate change...

Great fundraising, like the growth of bamboo, begins with unseen groundwork. The first five years may show nothing above the surface, but beneath lies a strong, intentional root system—just like the quiet outreach, relationship-building, and resilience fundraisers must invest before major gifts emerge. Today’s donor landscape demands more patience, personalization, and persistence than ever. When...

Right now, too many nonprofits are frozen in place—boards and CEOs so paralyzed by funding cuts and political chaos that they’ve stopped thinking strategically altogether. When organizations stall, donors lose confidence, talented development staff grow frustrated, and transformational gifts slip through the cracks. In this episode, we unpack four practical ways fundraising professionals can respe...

Most first-time donors are testing the waters—curious if your nonprofit delivers on its promise and if a deeper connection is worth their investment. That’s why speed isn’t just a courtesy in stewardship; it’s a strategy. In this episode, I explore how re-qualifying new donors within the first 90 days can mean the difference between a one-time gift and a lifetime of giving. The data is clear: fast...

Today marks a milestone—250 episodes of Around with Randall! This journey has been one of service, storytelling, and sincere gratitude for those unseen moments of influence we have on each other. What started as a simple goal to make a difference in just one life has blossomed into a community of listeners across the globe. I never imagined the reach or the impact, but I am deeply humbled and more...

Some of our most transformational donors are the ones you’ll never see on a wall or at a gala. They drive up in Hondas, not Bentleys—and they give in silence, often more generously than the loudest names on the marquee. But here's the catch: treating anonymity like invisibility is a critical failure. These quiet philanthropists still crave impact, connection, and trust—they just want it without th...

What is the concept of "choice architecture" in nonprofit fundraising? How can organizations better present options to donor and strike a balance between too much and too little information? Learn how to avoid common mistakes like the "Menu of Doom," false equivalency, and overselling, and discover practical strategies for curating meaningful giving opportunities that connect with donors' passions...

With fewer households making charitable gifts, annual giving is under pressure and needs a more strategic approach. Randall argues for evaluating annual giving through three-five year data trends rather than single-year snapshots. If nonprofits focus on trends, they can better allocate resources, elevate donors into major gifts or planned giving, and create lasting cultural shifts. Annual giving i...

Are you staring at stalled proposals and wondering what to do next? This episode dives into the root causes of donor dormancy—like misaligned timing, a disconnect in perceived value, or inconsistent follow-up—and offers a framework to triage and reengage major gift prospects. Learn how to categorize your dormant proposals, prioritize them by impact, and take practical next steps based on the kind...

1.Timing is everything — especially when it comes to making a major gift ask. In this episode, Randall explores the psychology behind donor readiness, uncovering the emotional and strategic signals that reveal the right moment to solicit transformational gifts. Learn the four critical feelings every donor must experience and the key questions to evaluate before making your move. If you want to mas...

In this episode, we check into the often-overlooked ethical complexities of donor recognition. Randall explores how poorly managed recognition can lead to mission drift, disproportionate acknowledgments, access inequities, problematic associations, and excessive donor involvement. With high-level donors becoming more sophisticated and competitive, nonprofits must be clear and intentional about how...

Building strong donor relationships goes beyond just securing gifts—it's about creating a meaningful feedback loop that fosters deeper, lasting connections. By listening to donors' perspectives, nonprofits can identify pain points, refine processes, and show that their voices matter. Randall also explores how this approach leads to better retention, upgraded gifts, and risk mitigation, all while b...

What does it really mean for a board to be strategic—and why does it matter? In this episode, Randall breaks down how defining strategy is the key to unlocking true board ownership and aligning long-term impact with community needs. It’s not about documents or retreats—it’s about thinking ahead, asking better questions, and creating a shared vision that reshapes roles, meetings, and expectations....

What can we learn from some of the world’s most influential philanthropists? In this episode of Around with Randall, we explore the giving philosophy of Steve and Connie Ballmer—how their approach to philanthropy started at the kitchen table and evolved into a multi-billion-dollar effort to drive economic mobility. Discover how data, trust-based giving, and a deep commitment to impact shape their...

Who really owns a nonprofit? Unlike for-profit businesses with clear ownership, nonprofits are technically owned by no one—but that doesn't mean responsibility is absent. In reality, the community is the true owner, and the board of directors serves as its steward. But what happens when boards become passive? CEOs can gain too much control, leading to governance failures, weakened oversight, and l...

Physicians play a critical role in philanthropy, particularly in health care, as trusted referral agents for grateful patient giving. This episode explores why physician engagement is essential and how their involvement leads to significantly larger gifts. While doctors shouldn't be asking for donations directly, they can recognize moments of gratitude, engage meaningfully, and transition relation...

Donor-advised funds (DAFs) are growing rapidly, presenting both challenges and opportunities for nonprofits. While they offer donors tax advantages, investment growth, and simplified giving, they also create barriers between nonprofits and the donors themselves. To effectively engage with DAF donors, nonprofits must proactively promote DAF giving options, retrain gift officers to discuss them, and...

This episode of Around with Randall explores the concept of upskilling, inspired by Amazon’s billion-dollar investment in workforce development. Randall discusses how acquiring new skills enhances career growth, job security, and personal satisfaction, particularly in the evolving nonprofit sector. He highlights practical ways to upskill—such as online courses, mentorship, and learning new softwar...

Wealth screening has long been a staple of donor identification, but the future lies beyond wealth—it's about connection and inclination. Let’s explore the evolution of screening, from manual processes to internet-driven data aggregation, and now the rise of artificial intelligence. AI is shifting the focus from static wealth indicators to behavioral patterns, predicting not just who can give but...

In this week’s episode of Around with Randall, we discuss the impact of positive and negative influences in our personal and professional lives, especially in the nonprofit sector. What is the science of emotional contagion, how others' emotions affect our well-being and productivity, and the importance of surrounding ourselves with positive individuals? We end with some practical advice for evalu...

In this week’s episode, we focus on the importance of endowing positions, particularly outside higher education, to create financial stability and attract top talent to nonprofits. Look at universities that have successfully endowed faculty chairs. How much could those endowments help nonprofits manage rising costs and ensure critical roles are funded? The goal is to help nonprofits adopt this mod...

Balancing personalization and automation in donor stewardship is a challenge every nonprofit faces. In this episode, Randall dives into the critical question of how to effectively engage donors at all levels—ensuring major donors feel valued while nurturing smaller donors with potential. He explores practical tactics for segmenting, automating, and personalizing stewardship efforts, from data-driv...