Rainmaker Fundraising

Every fundraiser on the planet has, at some point, wished they could have a prep conversation with a donor before they actually sit in front of them to make an ask of any kind. But that’s silly. That’s not possible. Instead, most of us settled for half-baked role playing with a colleague from time-to-time. And that was helpful. Sort of. But it was never exactly what we needed. It was never dialed in as much as many of us wanted. The result? Many of us still walked into donor visits and meetings nervous, unsure of ourselves, and unprepared to navigate […] Chapters (00:00:00) - Rainmaker Fundraising: Guest Interview (00:01:17) - Practical Learning for Fundraisers (00:03:31) - Facebook's First Paying Customers (00:03:50) - Why I Launched a Tech Company (00:08:10) - How the Fear-Based Fundraising System is Changing the Way (00:11:10) - Baker Fundraising: From Friendly to Fundraising (00:15:46) - The New Way to Coaching (00:18:28) - How To Raise Money With a Board of Directors (00:19:38) - Beyond the Money Flow (00:24:21) - Fundraising Goals and Motivation (00:26:15) - The New Goal-oriented Meeting (00:28:28) - "A Touch of Mercy" (00:29:17) - Give Like a Corporate Coach (00:31:08) - Coaching of the Leader (00:33:54) - Practivated: How to Navigate the Challenging Personality of (00:38:38) - A Few More Favors For You

“How are you?” Simple question, right? If you lead a nonprofit organization, a ministry, or work inside one, this probably feels like a loaded question. A trap, if you will. What we all know, but what so few are willing to admit, is that burnout is at an all-time high in our sector. As Nathan LaGrange, Executive Director at Oasis Rest International says, leaders don’t set out in their careers to flame out. No one wants to burn out, to harm their most precious relationships, or end up on the brink personal and professional failure. But it happens. https://youtube.com/shorts/ksKb5a8B_GI?feature=share In […] Chapters (00:00:00) - Rainmaker Fundraising Podcast: Rest and Recover (00:01:19) - Andrew McMillan on Planting His Soul (00:07:38) - Oasis Rest: A Place for Leaders to Talk (00:09:06) - Burnout in the Church (00:13:47) - The importance of caring for the leader (00:19:34) - A Sacred Controversy About Service Profit Chain (00:25:26) - How to Reset the Relationship Between CEO and Donor Development (00:29:13) - How Do You Retreat Away From Responsibilities? (00:32:57) - How to Encourage Your Pastor (00:35:54) - The Retreat Safety (00:38:04) - Life, Love, Liberty and Legacy (00:41:47) - Oasis of Rest (00:45:50) - How to Slow Down in Leadership (00:50:34) - Oasis REST: Slow Down (00:51:23) - How to Reach Out to Nonprofit Leaders (00:52:32) - The Rainmaker Fundraising Podcast

With access to clean water remaining a pressing issue in our world, charity: water stands out as a beacon of innovation and change. Brady Josephson, VP of Marketing and Growth (and a semi-regular guest on The Rainmaker show), shares insights into how the organization is transforming the way it engages with the world, driven by a relentless mission to provide clean water to every person on the planet. In our conversation, Brady the power of curiosity, a trait that fuels his (and the entire team’s) approach to innovation at charity: water. Working alongside the organization’s founder Scott Harrison, who embodies […] Chapters (00:00:00) - Rainmaker Fundraising Podcast (00:01:01) - Meet Charity Water's Chief Marketing Officer (00:02:50) - Dave Raley on His 'Superpower' (00:03:43) - Charity Water Executive Director on Innovation (00:07:37) - What's the Balance Between Innovation and Change at Charity Water? (00:12:18) - The Nonprofit Organization's Attention Challenge (00:15:18) - Creating a Charity Experience Lab in Franklin (00:18:11) - The World Without Water Experience (00:24:08) - Small Nonprofits: The Next Step in Innovation (00:29:57) - How to get in touch with Charity Water (00:30:36) - The Biggest Mistakes Nonprofits Make (00:31:04) - A Request for the Rainmaker Podcast

Should you invest in branding, OR, should you invest in fundraising? What creates greater impact for your cause? The answer often depends on who you ask. There are plenty of fundraising consultants who will tell you that investing in brand is a useless exercise, and all you need to do to be successful is invest in fundraising. Buy more direct mail. Spend more on paid ad programs. Hire more consultants. Do more events. If you’re not careful, you’ll invest in a grab bag of tactics that may not move the needle for you on revenue. Sadly, too many nonprofits do […] Chapters (00:00:00) - Kevin Brown on Fundable & Findable (00:00:45) - How to Build a Brand for Nonprofits (00:02:00) - Writing Down the Book (00:02:33) - Getting Out There: The LinkedIn Content (00:03:44) - Mission Clarity and How to Raise Money (00:06:30) - What is Vision for Nonprofit Leaders? (00:08:38) - The Secret to Success in Raising Money (00:11:03) - Brand Investment in Community (00:11:43) - Brand Investment: An Investment (00:13:17) - What Role Do Boards Have in the (00:15:01) - Strategic Plan: Everything Is Possible, But Everything Isn't (00:17:15) - The Investment Strategy of Building a Brand (00:18:17) - Nonprofit Communications and Brand Teams Understaffed (00:20:05) - How to Build a Nonprofit Brand with Just One Word (00:23:37) - A Few Favors for the Rainmaker

Do you know the 7 key donor performance metrics that drive organizational fundraising success in your nonprofit? My friends Gabe Cooper and Carly Berna from Virtuous help us dig into those KPI trends in this conversation about the Virtuous 2025 Nonprofit Benchmarking Report. Some of the insights we cover in this conversation include: The importance of donor retention, and the key difference between overall retention and net donor retention Challenges facing the nonprofit sector, and how doubling down on relationship, personalization, and automation can help offset some of those challenges Why you have to start leveraging data and automation (including […] Chapters (00:00:00) - The Rainmaker Fundraising Podcast (00:01:21) - Virtuous's 2025 Nonprofit Benchmarking Report (00:02:17) - The 7 KPIs that Matter The Most to Driving Revenue Growth (00:03:49) - Donor Experience: Days Between First and Second Gifts (00:06:46) - Donor Welcome Series (00:08:31) - The decline of the everyday donor (00:12:12) - The Future of Fundraising: Data Literacy (00:16:13) - Will AI Change the Way Nonprofits Raise Money? (00:19:23) - Mid- and Major Donors (00:25:48) - Mid-level Donors: The Middle Child (00:27:11) - Donor Outreach (00:30:23) - Nonprofit Giving: Average Gift Increases (00:33:22) - Are You More Likely to Give Online? (00:34:41) - Nonprofit Giving: New Donor Acquisition (00:37:43) - Donors' Long Term Value (00:39:30) - Ask Again: How to Ask the Donor (00:42:07) - Virtuous Nonprofit Data 2017: Most Encouraged (00:45:09) - Top Nonprofit Executives Discuss the Benchmark Report (00:45:54) - A Few More Favors For You

Do you know what sets the most generous fundraisers apart from the rest? In this episode of the Rainmaker Fundraising Podcast, Andrew Olson sits down with David Duxbury, Major Gift Officer at Hammer Residences, to explore the transformative power of generosity. David shares his personal journey from growing up in poverty to becoming a passionate advocate for donor impact. Together, they discuss the importance of humility in fundraising, the role of donor-centric communication, and how nonprofits can better empower the next generation of fundraisers. Packed with honest stories and practical wisdom, this conversation will inspire anyone working to build meaningful relationships in the nonprofit sector. Chapters (00:00:00) - The Rainmaker Fundraising Podcast (00:00:33) - Meet the Hammer Residences Major Gift Officer David Green (00:02:20) - In the Elevator With Charitable Givers (00:05:26) - Empowering the Next Generation of Fundraising (00:13:55) - The Importance of Humility (00:16:25) - How to Get Your Salesforce CRM to Do the Things You (00:16:57) - Donors Are Terrible People (00:17:37) - Philanthropist on How He Views Wealth (00:26:25) - Donor Centricity in Fundraising (00:31:11) - Donor Experience: How to Win at Fundraising (00:35:44) - What is Donor Stewardship? (00:39:42) - Top 10 Most Meaningful Donor Conversations (00:43:24) - The Rainmaker: Donating to Nonprofits

What does it really take to become a great fundraising organization? In this powerful episode of the Rainmaker Fundraising Podcast, Andrew Olson is joined by Alan Clayton, author of Great Fundraising Organizations and founder of Revolutionise. Together, they explore what separates thriving nonprofits from those that struggle, why fundraising success starts with leadership, and how to run two distinct operations—service delivery and fundraising—under one mission. Alan shares insights from global research, practical leadership strategies, and a call to embrace emotional storytelling, strategic investment, and a purpose-driven culture Chapters (00:00:00) - Alan Clayton on the Rainmaker (00:00:52) - Revolutionizing What It Is to Raise Money for Nonprofits (00:01:29) - Great fundraising organizations: The journey from good to great (00:03:08) - Getting organizations to commit to a five year plan (00:04:44) - What Makes Nonprofit Organizations Successful? (00:06:50) - The need for emotionally relevant engagement (00:09:29) - The role of the leader in fundraising (00:13:24) - How to Get Your Salesforce CRM to Work (00:13:59) - Philanthropy: The Leadership Problem (00:16:58) - The Conflict and Tension of the Fundraising (00:21:12) - The 3 Step Process of Brand Management (00:24:31) - In the Elevator With Andrew Carnegie (00:25:17) - What Makes a Charitable Leader So Driven? (00:28:58) - Laughably Leadership: A challenge to the (00:30:53) - Andrew Olson on the Biggest Mistakes Nonprofits Make (00:31:24) - A Few Favors for the Rainmaker

Is your nonprofit leaving long-term donor value on the table? In this episode of the Rainmaker Fundraising Podcast, Andrew Olson talks with Dave Raley, founder of Imago Consulting and author of The Rise of Sustainable Giving. Dave explains how the subscription economy is reshaping recurring giving and why many organizations fail to treat sustainers as the long-term partners they are. They explore the history of recurring giving, the elements of a strong sustainer program, and bust common myths about donor loyalty and communication. This episode is a must if your organization wants to grow predictable revenue and deepen donor commitment. Chapters (00:00:03) - Dave Raley on Why He Started Imago Consulting (00:04:12) - Bookmark: The Rise of Recurring Giving (00:09:08) - Subscriptions and Recurring Giving (00:15:24) - Your 90 Day Leaders Journey Email Course (00:19:03) - Sustainer vs. Long Term Value (00:20:37) - What Makes an Organization Ready for Sustainer? (00:25:49) - Should I Let a Major Donor Be a Monthly Donor? (00:26:21) - Are Your Recurring Donors More Valuable Than Your Major Don (00:29:50) - When Should a Major Donor Start Giving? (00:33:18) - Subscriptions in the Nonprofit Industry (00:37:56) - Cancel Your Subscriptions? (00:39:54) - Sustainer Program Launch: Benchmark, Evaluate and Design (00:44:08) - Sustainable Giving Growth Plan (00:45:52) - A Few Favors For You

Are you telling stories that truly inspire donor action? In this episode of the Rainmaker Fundraising Podcast, Andrew Olson talks with Tayloe Clements, Director of Digital Marketing at Barna Group and host of the Mission Money podcast. Tayloe shares her journey from filmmaker to nonprofit strategist and breaks down five key elements of compelling storytelling. She explains why conflict and transformation are essential, and offers practical advice for creating impactful video content—even with limited resources. Whether you’re a seasoned marketer or just getting started, this episode will help you level up your digital storytelling. Chapters (00:00:03) - Rainmaker: The Fundraising Podcast (00:00:46) - Taylor on His Leader Journey (00:02:02) - Barna the Swing dancer on How To Fit It All In (00:03:02) - Nonprofit Missionary (00:06:25) - What Excites You About Storytelling? (00:07:35) - The Story of Donor Engagement (00:11:19) - 4 Key Elements of a Mission (00:14:04) - Your Leadership Journey Email Course (00:15:48) - The Donor: The Hero of Nonprofit Marketing (00:19:10) - How to Coach Nonprofit Leaders on Camera (00:22:18) - How to Tell a Story in Video (00:26:15) - Andrew Olson: The Nonprofit Future (00:30:32) - Social Media: How to Tell the Story (00:33:44) - How to Start a Business in the Digital World (00:35:23) - A Few Favors For You

Could treating fundraising like a skilled trade transform your results? In this episode of the Rainmaker Fundraising Podcast, Andrew Olson sits down with Jason Zwang, founder of The Giving Group and longtime major gifts leader. Jason shares why major gift fundraising should be approached not just as a career, but as a craft that requires apprenticeship, trust-building, and continual learning. They explore the evolution of major gifts, the tension between science and art, and how organizations can prepare for the next generation of fundraising leadership. This is a masterclass in practical wisdom for anyone serious about long-term fundraising success. Chapters (00:00:00) - Raising Money Through Major Gifts (00:01:11) - Jason Levitt on Major Gifts (00:04:15) - Major Gifts as a Trade (00:05:13) - Philanthropy as a Trade versus a Career (00:09:15) - How to Balance the Pressure of Delivering This Year's (00:13:21) - Philanthropy and the Future (00:18:23) - The 90 Day Leader's Journey Email Course (00:19:47) - David Lively: The Need for Tradecraft (00:24:53) - The Art of Raising Money (00:28:22) - 3 Rules for Success in Raising Money (00:31:46) - What are you most excited for in philanthropy in the coming decade (00:33:38) - How Do Nonprofit Pro and Pro Speak? (00:34:11) - A Few Favors for the Rainmaker

How can failure become a catalyst for growth in nonprofit leadership? In this honest and empowering episode of the Rainmaker Fundraising Podcast, Andrew Olson is joined by Beth Fisher, CEO of Fisher Strategic. They explore how failure—especially public failure—can be one of the most powerful teachers for nonprofit leaders. Beth shares how to recover from setbacks, how to create psychologically safe cultures, and why investing in people is non-negotiable for organizations that want to grow. This episode offers practical insights for leading with authenticity, resilience, and empathy. Chapters (00:00:00) - Rainmaker: Failure and What We Can Do About It (00:00:56) - In the Elevator With Templeton Religion Trust's Director (00:01:55) - What is the Risk of Failure? (00:07:16) - Tom Clancy on Recovering From a Big Failure (00:10:17) - On Coaching and the Need for Support (00:14:00) - Steve Jobs on How Do You Manage Your Life? (00:15:34) - The 90 Day Leaders' Journey Email Course (00:16:47) - On the Toxic Environment (00:18:36) - The Need for a Safe Workplace (00:19:54) - Performance Review and the Gray Area (00:21:08) - Does the Enneagram Affect How You're Seen? (00:22:10) - The 3 Biggest Mistakes Nonprofits Make (00:25:48) - WSJDLive: Leading Transformational Change (00:27:20) - What Have You Learned From Your Biggest Fails? (00:30:50) - Rainmaker: A Request for Help

Are your fundraising and PR efforts working in harmony—or getting in each other’s way? In this episode of the Rainmaker Fundraising Podcast, Andrew Olson sits down with Jessi Marsh, Senior Director of Creative Strategy at DickersonBakker, to explore how public relations and fundraising can support each other for greater impact. Jessi shares practical strategies for building media relationships, positioning your nonprofit as a thought leader, and coordinating PR efforts to elevate donor engagement. From crisis response to calendar planning to election-season storytelling, you’ll learn how to use the media to raise both your visibility and your revenue—without stepping on your fundraising team’s toes. Chapters (00:00:00) - The Intersection of Public Relations and Raising Money (00:01:22) - How to Manage Public Relations? (00:02:56) - What is a Press Release? (00:04:34) - How to Plan Your Public Relations Plan (00:09:34) - Are You Needing a News Media Presence? (00:10:39) - How to Promote Yourself as a Thought Leader (00:12:51) - The 90 Day Leaders' Journey Email Course (00:14:10) - How to Leverage Public Relations to Support Fundraising (00:20:48) - How Do Non-profits Compete During an Election Season? (00:22:32) - Inflation and domestic violence (00:23:57) - What Do You Say to Nonprofit Leaders Who Are Afraid to (00:27:09) - Responsive PR for Israel's Crisis (00:33:11) - Jennifer Marsh and Jesse Baker on Public Relations (00:35:39) - A Few Favors for the Rainmaker

Is your organization suffering from quiet decline—and would you even know it if it was? In this episode of the Rainmaker Fundraising Podcast, Andrew Olson talks with Jim Langley, founder of Langley Innovations and former advancement leader at Georgetown, Georgia Tech, and UC San Diego. Together they explore the concept of institutional rot in the nonprofit sector, unpack why courage and curiosity are essential leadership traits, and challenge the rinse-and-repeat fundraising mindset that keeps organizations stuck. Jim shares hard truths about complacency, the decline in donor participation, and what it really takes to build lasting community and partnership. If you’re serious about the future of your organization, this conversation will wake you up and point you forward. Chapters (00:00:00) - Jim Langley on Raising Money (00:01:57) - Philanthropy: The Vital Signs of Organizations (00:04:53) - The Importance of Courage (00:08:47) - Coronation 6: Courageous Leaders (00:16:50) - The 90 Day Leader's Journey Email Course (00:18:07) - Donor Satisfaction and the (00:27:03) - Philanthropy's Future (00:34:32) - Jim Vance on How to Reach People (00:35:30) - A Few Favors for the Rainmaker