As AI changes the way nonprofits connect with donors, the big question is: can technology make fundraising more personal, not less? 

Derric Bakker, CEO at DickersonBakker, explores how fundraising has moved from personal, relationship-based work to more transactional communication. He shares how AI can help nonprofits bring personalized donor experiences to more people, not just major donors. 

The discussion covers key ideas such as listening to donors, personalizing messages, showing genuine thanks, building trust, respecting donor timing, and focusing on long-term relationships.  

Derric also highlights the importance of using AI responsibly. Nonprofits should be honest when AI is involved and should never use technology to trick or pressure donors. Trust is at the heart of successful fundraising, and once it is lost, it can be difficult to rebuild.  

The conversation also looks at how nonprofits can use AI to scale personal communication while keeping the human side of fundraising strong.  

Overall, the message is simple: use AI to strengthen relationships, not replace them. The future of fundraising should combine smart technology with genuine human connection. 

HIGHLIGHST  

[02:00] Derric's Professional Journey  

[06:07] The Shift Toward Transactional Fundraising 

[10:37] Genesis of A Better Way to Fundraise  

[16:46] Core Principles of Relationship Fundraising 

[21:17] AI Ethics and Maintaining Donor Trust  

[35:19] The Future Outlook for Fundraising 

Resources: 

Connect with Derric: 

LinkedIn: linkedin.com/in/derricbakker/ 

Website: betterwaychampions.org/ 

Website: dickersonbakker.com/ 

Mentioned in the episode: 

A Better Way to Fundraise - Treat Every Donor Like a Major Donor: How AI is Enabling Major Giving at Scale - And Reshaping the Future of Philanthropy: amazon.com/Better-Way-Fundraise-Reshaping-Philanthropy 

Better Way Champions — Resources and a growing community of nonprofit leaders working to rethink the future of fundraising: BetterWayChampions.org 

Better Way Champions on Substack — Derric's latest writing on fundraising, philanthropy, AI, and the changes reshaping our sector: https://betterwaychampions.substack.com/subscribe 

Today, let's explore how good data, clear goals, and trust are the real keys to getting value from AI. 

Meet Daniel Basco, Senior Director, iWave & Data Intelligence at Kindsight. 

Starting the conversation, Daniel shares his career journey from public policy and economics to data science and fundraising. He talks about his work with governments, nonprofits, and now Kindsight, where he leads data science and AI product development.  

The conversation explores how AI and machine learning have improved over the years, making it easier to test ideas and work faster. Daniel explains why organizations need clean, reliable data and why it is important to understand how AI reaches its conclusions. He also discusses the need to reduce bias and use AI ethically.  

Furthermore, Daniel talks about the benefits of combining different data sources to improve results and how AI can help nonprofits make better decisions and improve daily work. He discusses the importance of teamwork, experimenting with new ideas, and continuing to learn as AI evolves. He also shares how he uses Claude to communicate ideas more clearly, brainstorm faster, and save time in his daily work.  

HIGHLIGHTS

[01:47] Daniel's Career Journey  

[07:12] Challenges and Evolution in AI and Machine Learning  

[11:26] Data Utilization and Predictive AI in Nonprofit Sector 

[18:17] Transparency and Trust in Nonprofit AI Models 

[29:01] Future of AI in Nonprofit Sector  

[35:23] Personal Reflections and Favorite AI Tools

Resources: 

2025 Donor Perceptions of AI Report: kindsight.io/resources/ebooks/2025-donor-perceptions-of-ai-report 

Connect with Daniel: 

LinkedIn: linkedin.com/in/daniel-basco 

Website: kindsight.io/ 

In a world where change is happening faster than ever, the biggest challenge is not just finding new tools; it is helping people feel ready to use them. 

In today's episode, Nathan talks with Mallory Erickson, the creator of Practivated, the first fundraiser readiness platform. Mallory shares the story behind Practivated and explains that it was created to solve real problems in the fundraising sector, including fundraiser burnout, declining participation, and the need to better support professionals. She explains that her goal was not just to build a technology product, but to create a solution that helps people grow their skills and confidence. 

Furthermore, Mallory discusses the challenges of AI adoption, including fear, resistance to change, and the difficulty leaders face when trying to introduce new ideas. She explains how Practivated helps people build AI confidence through role-play, coaching, and feedback. The conversation also explores why practice is important for turning knowledge into real action and why curiosity is more valuable than trying to have all the answers.  

[04:05] Solving the Right Problem 

[09:18] Balancing Realism and Awareness 

[16:13] The Real Innovation Barrier 

[22:27] Trust Before Technology 

[29:04] Confidence Is Curiosity 

[38:18] Practice as a Path to Progress 

Connect with Mallory: 

LinkedIn: linkedin.com/in/mallory-erickson-bressler/ 

Website: malloryerickson.com 

Website: practivated.com 

Have you ever considered what the bigger risk is? Adapting the wrong AI tool or waiting too long to get started?  

Since predictive, generative, and agentic AI continue to alter how organizations operate, understanding how these different technologies complement one another is of utmost importance. This conversation revolves around the measurable impact of AI, while addressing concerns from making advanced analytics accessible to nonprofits of all sizes to using AI for smarter fundraising decisions. Join us and learn why incomplete or messy data shouldn’t stop you from using AI, how predictive AI uncovers opportunities, and why treating AI as a strategic capability rather than another tool can help organizations to enhance efficiency, increase revenue, and stay at the very top of an increasingly AI-driven world. 

Our guest today is Judah Phillips, the Chief AI and Product Officer at Market Holdings LLC and the General Manager and co-founder of Squark AI, a no-code platform for predictive analytics, forecasting, and decision intelligence. Beyond his professional role, Judah founded the Boston Generative AI Meetup, one of the world's largest in-person AI communities, and Boston AI Week, a citywide AI festival. He is also the author of multiple books related to analytics, e-commerce, and AI. His work specializes in bridging AI strategy, commercialization, governance, investment, and community building to accelerate AI adoption. 

In this conversation, Nathan and Judah mainly discuss the developing relationship between predictive, generative, and agentic AI and how it affects the fundraising landscape, also what the future holds for AI and why it’s important to build AI capabilities early on.  

[01:23] Introduction and background to Judah Phillips.  

[06:48] Judah’s journey on the development of Squark AI.  

[20:46] Making sophisticated capabilities accessible to everyone, not just building models.  

[25:52] Using predictive AI to solve real fundraising challenges. 

[38:37] The future convergence of predictive AI, generative AI, and agentic AI. 

[45:00] The importance of adopting an AI mindset before the technology moves too far ahead.

RESOURCES 

Connect with Judah Phillips 

LinkedIn - linkedin.com/in/judahphillips/  

Website - squark.ai/ 

AI is changing the way we work, create, and make decisions, but are we ready for the changes ahead? From privacy concerns to powerful new AI tools, this conversation explores what the future may look like! 

Discussing Meta's privacy concerns, including a new Instagram update, Nathan and Scott stress the need for people and organizations to better understand how their data is used.  

The conversation also looks at Microsoft layoffs and the importance of training employees with new skills instead of only replacing jobs. Then Sam - ChatGPT joins the discussion to explain new AI models from OpenAI and Anthropic and how they can help people work faster and smarter. In conclusion, Nathan and Scott mention that different AI tools have distinct strengths, so users should choose the right tool for each task.   

HIGHLIGHTS

[00:00] Giving USA Annual Symposium 

[03:31] This week's AI Advancements 

[04:47] Meta's Privacy Concerns  

[08:32] AI Needs Guardrails  

[09:18] Microsoft Recent Layoffs 

[19:06] OpenAI and Anthropic's New Models  

[23:56] Choose the Right Tool for the Job 

Resources: 

Connect with Nathan and Scott: 

LinkedIn (Nathan): linkedin.com/in/nathanchappell/ 

LinkedIn (Scott): linkedin.com/in/scott-rosenkrans 

Website: fundraising.ai/ 

Mentioned in the episode: 

Shrug Philanthropy: linkedin.com/pulse/shrug-philanthropy-nathan-chappell 

AI is changing the way we work, but using it wisely is key to getting real value! 

In this conversation, Nathan and Scott talk about Anthropic's Fable model and how AI tools can help with complex tasks, improve productivity, and support better decision-making. The conversation highlights the importance of choosing the right AI model for the right job instead of using powerful tools for every task. 

Another important topic discussed is the environmental impact of AI. Nathan and Scott discuss how responsible AI use can help reduce unnecessary energy use by selecting efficient models, reviewing AI habits, and planning tasks at better times. 

The discussion also explores the challenges organizations face when adopting AI. They explain that successful AI adoption is not just about buying new technology but about developing the right strategy, training teams, and ensuring AI supports the organization's goals. 

They also highlight the importance of human-AI collaboration, where people and technology work together to achieve better results. As AI continues to develop rapidly, staying up to date, testing new tools, and using AI responsibly will help organizations make the most of this growing technology. 

HIGHLIGHTS

[02:40] Discussion on Anthropic's Fable model 

[08:45] Environmental Impact of AI 

[10:17] Model Routing and AI Adoption 

[19:06] Human-AI Collaboration and Organizational Adaptation 

[28:15] The Emperor's New Clothes Analogy and AI Adoption Challenges 

[31:35] Conclusion 

Connect with Nathan and Scott: 

LinkedIn (Nathan): linkedin.com/in/nathanchappell/ 

LinkedIn (Scott): linkedin.com/in/scott-rosenkrans 

Website: fundraising.ai/ 

Nonprofit AI: A Comprehensive Guide to Implementing Artificial Intelligence for Social Good:  

amazon.com/Nonprofit-Comprehensive-Implementing-Artificial-Intelligence-ebook 

The Article I Kept Not Writing: linkedin.com/pulse/article-i-kept-writing-nathan-chappell 

While many people know about AI, not everyone chooses to use it. The key difference is curiosity and the willingness to try new tools! 

During today's conversation, Nathan shares stories from his AI training sessions, showing how hands-on practice with tools such as ChatGPT, Claude, and NotebookLM helps people understand what AI can and cannot do. 

The conversation also looks beyond productivity to discuss important topics such as AI's environmental impact, ethical concerns, and its growing influence on the way people write and communicate. Nathan talks about the need to use AI responsibly and shares ideas from his work on sustainable AI. Scott adds that people should focus on using AI to solve real problems instead of relying on it for everything. 

Furthermore, Nathan and Scott explore how AI can support the nonprofit sector, the rise of new AI systems that combine multiple models, and the increasing amount of AI-generated content on platforms such as LinkedIn. They end the conversation by encouraging listeners to stay curious, keep learning, and use AI as a tool to support, rather than replace, human creativity. 

HIGHLIGHTS

[01:04] AI Training and Practical Applications 

[12:30] Agency and AI Adoption 

[13:39] Environmental Impact and Ethical Concerns  

[16:27] Philanthropy and Nonprofit Sector Challenges  

[22:42] Technical Advancements in AI  

[32:48] LinkedIn and AI-Generated Content  

[37:12] AI's Influence on Language and Communication  

Resources: 

Connect with Nathan and Scott: 

LinkedIn (Nathan): linkedin.com/in/nathanchappell/ 

LinkedIn (Scott): linkedin.com/in/scott-rosenkrans 

Website: fundraising.ai/ 

Website (Nathan): nathanchappell.com/ 

Behind every new AI breakthrough lies a bigger question: who benefits, who loses, and what comes next? 

In this conversation, Nathan and Scott explore some of the biggest debates shaping the future of artificial intelligence. They begin with Apple's WWDC announcements, discussing Siri's major upgrades and how on-device AI could make it a smarter and more personalized assistant. The discussion then shifts to Anthropic and its Claude models, including Fable, a safety-focused AI system that was ultimately shut down due to potential risks.  

Nathan and Scott also examine changing narratives around AI and employment, questioning why industry leaders such as Sam Altman and Dario Amodei have recently shifted from warning about job losses to promoting job creation, especially as their companies prepare for IPOs. Finally, they tackle AI's environmental impact, highlighting the energy demands of data centers and considering whether future technologies, such as quantum computing, could provide sustainable solutions. 

HIGHLIGHTS

[02:44] WWDC and Siri Updates  

[12:07] Anthropic and Claude Models  

[22:20] Impact of AI on Jobs and IPOs 

[30:00] Environmental Concerns and AI  

Resources: 

Connect with Nathan and Scott: 

LinkedIn (Nathan): linkedin.com/in/nathanchappell/ 

LinkedIn (Scott): linkedin.com/in/scott-rosenkrans 

Website: fundraising.ai/ 

Mentioned in the episode:  

The Artificial Intelligence Show: podcast.smarterx.ai/ 

The AI Daily Brief: aidailybrief.ai/ 

This episode features Sophia 'Puff' Story, Co-Founder of 3 Sided Cube USA, exploring how mission-driven technology and artificial intelligence are reshaping both business and nonprofit sectors. Sophia shares how 3 Sided Cube builds "tech for good" products designed to improve millions of lives, and reflects on their experience using AI to develop a new website, an effort that revealed the continued importance of human judgment. 

The discussion turns to the company's expansion into the US market, driven by strong demand and early revenue traction. Nathan and Sophia then examine the accelerating impact of AI on nonprofits, highlighting both opportunities and challenges in adoption, including governance, compliance, and strategy. Sophia further emphasizes experimentation, clear goal-setting, and measuring success before deploying AI solutions. The episode concludes with a call for nonprofits to embrace risk-taking, continuous learning, and practical AI experimentation to stay relevant in a rapidly evolving landscape! 

HIGHLIGHTS

[03:21] 3 Sided Cube USA and Its Brand  

[06:26] Expansion to the US Market  

[11:40] Impact of AI on Business and Nonprofit Sectors  

[14:58] Challenges and Opportunities in Nonprofit AI Adoption  

[23:21] The Role of AI in Nonprofit Innovation  

[34:01] The Behaviors Behind Innovation 

Resources: 

Connect with Sophia: 

LinkedIn: linkedin.com/in/sophia 

Website: 3sidedcube.com/ 

Mentioned in the episode: 

ai-adoption.3sidedcube.com/ 

marketing.3sidedcube.com/ai-adoption-toolkit 

What happens when artificial intelligence advances faster than society's ability to adapt? And what role should nonprofits, faith leaders, and technology providers play in shaping a future that remains deeply human? 

In this episode, Nathan and Scott reflect on key discussions from the Virtuous User Summit, where AI emerged as a central theme for the nonprofit sector. They examine the unique culture of collaboration within nonprofits and the responsibility of technology partners to support missions that serve the common good. A major focus is the Pope's recent encyclical on AI, which raises concerns about the concentration of power, the dehumanizing potential of unchecked technology, and the need for ethical safeguards.  

The conversation also explores AI-driven workforce disruption, growing demand for nonprofit services, and the sector's readiness to respond to these challenges. Beyond the risks, Nathan and Scott highlight practical opportunities for AI adoption, encouraging leaders to move beyond fear, fatigue, and FOMO through experimentation and curiosity. They discuss emerging AI models, personalized AI assistants, knowledge-management tools, and automation that can free people to focus on creativity and relationships.  

HIGHLIGHTS

[01:30] AI's Moral Imperative and Nonprofit Sector Challenges 

[04:23] Pope's Encyclical on AI and Its Implications 

[10:18] Nonprofit Sector's Preparedness for AI Disruption 

[20:44] Practical AI Adoption and Overcoming Challenges 

[25:51] New AI Models and Their Capabilities 

[31:56] AI Tools and Personalized AI  

[38:00] AI's Impact on Society and Ethical Considerations 

Connect with Nathan and Scott: 

LinkedIn (Nathan): linkedin.com/in/nathanchappell/ 

LinkedIn (Scott): linkedin.com/in/scott-rosenkrans 

Website: fundraising.ai/ 

Obsidian: Obsidian.md/