The Logic of Generosity

Legacy isn’t a stack of documents or a dollar amount. It’s a story—told through choices, values, and the people we trust to carry them forward.Tiffany knows this. She doesn’t just interpret tax codes or navigate estate plans. She translates complexity into clarity, aligning families, advisors, and nonprofits around what truly matters.She’s the connective tissue—linking financial strategy to personal purpose. For nonprofits, she unlocks deeper conversations with donors. For advisors, she brings cohesion to the planning table, ensuring the family’s vision stays front and center.Tiffany isn’t selling advice. She’s building alignment—around legacy, generosity, and impact.If your work touches lives—through philanthropy, planning, or purpose—this episode will reframe how you think about your role in someone’s bigger story. Because in the end, it’s not just about wealth. It’s about what we leave behind—and who helps shape it.For more information about Tiffany, please visit: https://giftplanninginstitute.com/ For more information about Stillwater Capital Management, please visit: https://www.stillwatercapitalmgmt.com/For more information about Pleiades Nonprofit Advisors, please visit: https://pleiadesnpa.com

Jay Harvill doesn’t just work in fundraising—he helps people imagine the impact they can have for generations. For over two decades, he’s served as a bridge between generous hearts and the transformational change they want to create. His leadership has turned planned giving from a quiet corner of development into a bold, strategic force.At Methodist Hospital Foundation in Arcadia, where Jay has led Gift & Estate Planning and Major Gifts since 2005, he’s helped redefine what's possible. Under his guidance, the team has exceeded campaign goals, multiplied planned giving revenue fivefold, and built a 15-year expectancy pipeline that mirrors current annual revenue—ensuring long-term sustainability for the hospital’s mission. But metrics only tell part of the story. Jay's real work is human—coaching staff, earning donor trust, and working shoulder-to-shoulder with financial advisors, attorneys, and community leaders to craft charitable plans that are as smart as they are generous.He’s the kind of leader who doesn’t shy away from complexity. Whether it’s stewarding gifts of commercial land or designing life income plans that align with a donor’s retirement vision, Jay brings clarity, strategy, and a deep respect for the values that drive giving.Before his time at Methodist, Jay led planned and major gift efforts at Braille Institute, where he built strong, personal connections with donors, and launched marketing strategies that helped grow awareness of philanthropic opportunities in bold new ways.And before philanthropy called, Jay cut his teeth in the corporate world—helping business clients navigate banking, wealth planning, and succession at Citigroup and Wells Fargo, and negotiating major corporate agreements at Hughes Aircraft. He even spent time on the front lines of higher ed outreach with Pepperdine’s business school, leading the region in student enrollments.Jay brings together a rare mix: strategic mind, relational heart, and a clear sense of why it all matters. He believes giving is not a transaction—it’s a legacy. And his career is proof that when you empower people with vision and generosity, extraordinary things happen.Our Sponsorswashingtontimes.comstillwatercapitalmgmt.compleiadesnpa.comFor Dr. Russell James' work, please visit: encouragegenerosity.com

Kevin Barry is an AVP at Mount Saint Mary's University and brings a fresh perspective towards relationship driven leadership and donor connectivity. Kevin is an exceptional fundraiser, storyteller, optimist, philanthropist and has recently become a doctoral candidate in leadership and innovation.

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Business, no matter what business you are in, is all about building relationships. That's what Kevin Barry does. He develops and leverages relationships to generate support for causes that he am passionate about. Over the past few years, Kevin's work has been focused on developing and executing fundraising initiatives and public relations campaigns on behalf of institutions of higher education.