Mastering Fundraising

What happens when the generations represented around the fundraising table bring different experiences, expectations, communication styles, and ideas about philanthropy?

In this episode of Mastering Fundraising, host Chris Looney sits down with Yuri E. Casco, MPH, CFRE, Director of Major Gifts at Pacific Clinics, to explore intergenerational leadership and what it means for fundraisers, donors, boards, and nonprofit organizations.

The conversation comes at a fitting moment. On the day the episode was recorded, Yuri was celebrating exactly 25 years since she began her career in nonprofit fundraising.

Drawing from those 25 years of experience, Yuri offers a simple but important principle for working across generations: don't assume. Ask. Listen. Be curious.

Chris and Yuri explore:

• Why generational understanding should be a starting point, not a stereotype

One of the most important ideas from the conversation is that effective intergenerational leadership isn't about memorizing the characteristics of Baby Boomers, Gen X, Millennials, or Gen Z. It is about understanding the person in front of you.

As Yuri reminds us, our donors, colleagues, board members, and community leaders bring their own lived experiences. The better we become at listening to those experiences rather than making assumptions about them, the better leaders and fundraisers we can become.

And as an unprecedented transfer of wealth and leadership continues across generations, that ability to build authentic relationships across age groups will only become more important.

Join Chris and Yuri for a thoughtful conversation about curiosity, inclusion, relationships, and how different generations can work together to strengthen the future of philanthropy.

Listen to this episode of Mastering Fundraising.

What happens when your fundraising ambitions outgrow the systems designed to support them?

Growth is something every nonprofit wants. More donors. Larger gifts. Bigger campaigns. Greater impact. But growth without the right infrastructure can create complexity, strain teams, weaken the donor experience, and ultimately make an organization more fragile rather than more successful.

In this episode of Mastering Fundraising, host Chris Looney sits down with Sasha Villacis, founder of Inspiring Philanthropy, to explore what it really takes to scale a fundraising operation.

Sasha draws on more than two decades of experience in fundraising, prospect development, advancement services, systems design, and organizational strategy to examine the often-overlooked connection between fundraising success and the operations behind it.

Together, Chris and Sasha explore:

• The critical difference between growing fundraising and actually scaling it

• The warning signs that your fundraising ambitions have outgrown your infrastructure

• Why breakdowns often happen at the handoffs between people, departments, and systems

• Why fundraising strategy and operations must work as one integrated engine

• How better systems can strengthen stewardship and protect donor trust

• How to build a more agile fundraising operation without creating unnecessary complexity

• Where artificial intelligence can genuinely help fundraising teams work smarter and scale

• Why AI can make good processes faster, but can also make confusion faster

Sasha also introduces the ESSA framework: Eliminate, Simplify, Standardize, Automate, a practical approach organizations can use before layering AI and automation onto existing processes.

Perhaps her most practical advice for leaders confronting operational growing pains is simple:

“Start small enough to learn, but important enough to matter.”

Pick one process. Understand who owns each step. Identify where work stops, where information gets lost, and where unnecessary complexity exists. Improve it. Learn from it. Then keep going.

If your organization has ambitious fundraising goals, the question isn't simply whether you have the donors and fundraisers to achieve them. It's whether the organization behind those fundraisers is built to support that ambition.

This conversation will help you think differently about what it truly means to scale fundraising.

Who really makes the philanthropic decisions in a household?

For fundraisers, the answer may not be nearly as obvious as we think.

In this episode of Mastering Fundraising, Chris Looney sits down with Deidre H. Sandvick, Senior Vice President for Development at the University of New Mexico Foundation, for a conversation about women in philanthropy, donor relationships, and the assumptions that can quietly undermine even the most experienced fundraisers.

Deidre shares a powerful story from her time at the University of Oregon involving a generous donor couple and a seven-figure gift that simply wasn't moving forward. The university had built a strong relationship with the husband, but had never developed the same relationship with his wife. When Deidre finally sat down with her, she discovered a critical piece of information that changed the entire strategy.

The lesson went far beyond one gift.

Deidre challenges fundraisers to recognize both partners as having agency in philanthropic decisions, stop treating spouses as "plus ones," and become much more intentional about understanding who influences a family's giving.

Throughout the conversation, she returns to one deceptively simple question that she regularly asks her own development teams:

"How do you know that?"

How do you know what a donor cares about? How do you know the spouse isn't interested? How do you know who makes the decision? Did the donor actually tell you, or did you fill in the gaps yourself?

Chris and Deidre also explore research on women's growing philanthropic influence, how fundraisers can better engage both members of a household, and why curiosity may be one of the most important skills in our profession.

The conversation echoes the research of the Women’s Philanthropy Institute at the Lilly Family School of Philanthropy and the work of Kathleen Loehr in Gender Matters: A Guide to Growing Women’s Philanthropy: gender influences giving, and fundraising practices need to evolve with the donors we serve.

Deidre's advice ultimately extends well beyond women in philanthropy:

Stay curious. Listen to people whose experiences differ from your own. And above all, don't assume.

From Transactional to Transformational: The Leadership Journey Every Fundraiser Should Understand

What prepares someone to become an exceptional Chief Development Officer?

According to Tianna Haradon, CFRE, it isn't one promotion, one campaign, or one major gift. It's a career built intentionally, one experience at a time.

In this episode of Mastering Fundraising, Tianna shares how she evolved from managing sponsorship checklists and event logistics to leading one of Southern California's most respected fundraising programs as Chief Development Officer at The Wooden Floor.

Along the way, she reveals why every stage of a fundraising career matters.

You will learn:

• Why the earliest fundraising roles create the foundation for long-term success.

Perhaps Tianna's most important reminder is that careers are not built by skipping steps. They are built by mastering each one.

Whether you're beginning your fundraising journey, leading a development team, or preparing for your next leadership opportunity, this conversation offers practical wisdom and encouragement for every stage of your career.

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In this insightful episode of Mastering Fundraising, host Chris Looney sits down with longtime advancement leader Jocelyn Tetel of the Skirball Cultural Center to explore what it truly takes to cultivate sophisticated donors in today’s evolving philanthropic landscape.

With nearly three decades of experience, Jocelyn shares her unconventional journey from the insurance industry into nonprofit fundraising and reveals how relationship management, disciplined process, and genuine curiosity became the foundation of her success.

Together, Chris and Jocelyn unpack what defines a “sophisticated donor” today, from seasoned philanthropists with established giving portfolios to emerging donors shaped by family philanthropy and advisory networks. The conversation moves beyond theory into practical strategy, offering clear guidance on how to build trust, communicate effectively, and create meaningful engagement that goes far beyond transactional giving.

Listeners will gain valuable perspective on:

Jocelyn also offers candid advice for nonprofit leaders on hiring, culture, and the importance of building teams that can support sophisticated donor relationships at every level of the organization.

Whether you are a frontline fundraiser, executive leader, or board member, this episode provides a masterclass in cultivating meaningful, long-term donor relationships grounded in authenticity, discipline, and strategic insight.

If you’re looking to elevate your fundraising approach and better engage today’s most discerning donors, this is a conversation you won’t want to miss.

Navigating Leadership Change: Staying Grounded in the Midst of Constant Transition In this episode of Lead for Good, host Chris Looney sits down with Sara Colvin for a candid and deeply practical conversation about one of the most common yet least discussed realities in nonprofit leadership: constant change at the top. Drawing from her experience working under multiple chancellors and advancement leaders over more than a decade, Sara offers a powerful perspective on what it means to lead with stability when everything around you is shifting. She introduces the concept of “strategic direction whiplash” and unpacks the real impact that leadership turnover has on teams, donors, and long-term fundraising success. Throughout the conversation, Sara shares actionable insights on how leaders can remain grounded and effective during transition, including: *Why the best leaders become “institutional anchors” who preserve mission, memory, and momentum *How to support teams through changing expectations, KPIs, and leadership styles *The importance of anchoring donor relationships in mission rather than individuals *How to thoughtfully navigate donor engagement during leadership turnover *A practical leadership framework built around her “three P’s”: people, purpose, and production Sara also offers a compelling reminder that while leadership change can feel overwhelming, it is temporary, while the mission, the people served, and the impact of the work are what endure. This episode is essential listening for nonprofit executives, advancement professionals, and emerging leaders who want to lead with clarity, resilience, and purpose, even in the most uncertain environments. Listen in to learn how to steady the ship, protect what matters most, and continue leading for good no matter who’s in the corner office.

In the latest episode of Mastering Fundraising, Chris Looney, CEO of Fulcrum, sat down with Gloria Crockett to explore how fundraising can move beyond transactions and into true movement building.

The conversation centers on a critical distinction: the difference between running a campaign and building a movement.

A campaign has a defined goal and timeline.

Gloria shares practical insights from decades of nonprofit leadership, including:

• Why disruption is necessary in today’s crowded philanthropic landscape

This episode challenges leaders to rethink not the importance of revenue, but the approach to generating it.

If your organization wants stronger relationships, greater momentum, and more sustainable results, this conversation is worth your time.

Check out the full episode on YouTube here: https://youtu.be/MkoZpLZ8OWY

What does it really take to align your board and CEO around a successful campaign?

In this episode of Mastering Fundraising, Chris Looney sits down with LaMont Hayes, Associate Vice President of Development at the National WWII Museum, to unpack one of the most critical and misunderstood dynamics in campaign fundraising: managing board and CEO involvement.

With more than 20 years of experience leading major campaigns across healthcare, higher education, arts and culture, and now one of the nation’s premier museums, LaMont shares practical, candid insight into:

• The distinct roles of the board and CEO in a campaign

LaMont also shares stories from campaigns that exceeded goal and ones that did not, offering real-world wisdom about listening to donors, aligning strategy, and building long-term relationships beyond a single campaign.

If you are preparing for a campaign, in the middle of one, or simply trying to better partner with your board and CEO, this conversation is packed with actionable insight you can use immediately.

Watch the full episode and subscribe for more conversations with nonprofit leaders mastering their craft.

The fundraising playbook is being rewritten in real time.

In this episode of Mastering Fundraising, Tom Mitchell draws on decades of leadership in higher education advancement to confront a hard truth: many institutions are hesitating at the very moment bold leadership is required.

Tom has spent his career helping universities build strong advancement programs, develop talent, modernize strategy, and raise transformational resources in service of their communities. From campaign strategy to leadership development to innovation in data and analytics, his work has shaped institutions and influenced professionals across the country. In this conversation, he reflects on the inflection points that defined his journey and what they reveal about the future of fundraising.

Together, we explore:

• The Great Hesitation and why leaders are stuck between stability and change

If you lead advancement, development, alumni engagement, or philanthropy strategy, this episode challenges assumptions and invites you to think bigger.

The question is not whether fundraising will change. It is whether we are ready to lead that change.

Listen now and join the conversation shaping the future of our profession.