Today, we continue our series on the worst advice I’ve seen when it comes to growing sustainable recurring giving. 

This advice is almost always well-meaning and might sound reasonable in the moment, but it can be dangerous if followed.

I’ve heard a lot of advice over the years about recurring giving. Some of it’s brilliant. Some of it’s practical. And then… there’s the other kind.

Well-meaning, confident advice that sounds reasonable in the moment — but if followed, could quietly choke the very growth in sustainable giving we’re trying to cultivate.

That’s the advice I want to call out here. Not to shame those who said it or repeat it (they usually mean well), but because I’ve seen how harmful it can be if leaders take it to heart. Think of this as a running log of “the worst advice I’ve ever heard on sustainers.” Every so often, when I come across a new gem of misdirection, I’ll add it to the list.

Today’s a quick one – we’ll start with one of the most recent “gems” I’ve heard.

Over the next few weeks, I’ll share more of the worst advice I’ve heard when it comes to sustainable recurring giving.

I’m encouraged.

This week, I was blessed to give the opening keynote at the Citygate CEO Summit in Chicago. Being in a room with CEOs of some of the most impactful human services charities in the nation was heartening.

This week, I did something that I’ve never done in my life. 

I sailed a boat. 😬

We are embracing the final days of summer break in the Raley household. School starts next week, so this past week as a family we struck out for adventure on the Puget Sound in and around the San Juan Islands, or as they are known in the PNW, the “San Juans.” 

We didn’t go it alone, though. We were joined by Grandpa, and led by intrepid Captain K, an experienced sailor with decades of experience, who knows just about everything there is to know about life on the seas.

Did you know that Sunday, August 17, is National Nonprofit Day?

On August 17 each year, National Nonprofit Day recognizes the goals and positive impacts nonprofits have on communities and the world.

I still remember the time my professor in the school of business at Azusa Pacific University said to us, “Nonprofit doesn’t mean no profit” – it means “not for profit.” Nonprofits need to make a profit to accomplish their mission, but they exist in the U.S. for purposes other than generating a profit. They exist to address a social issue, or a marginalized group, or to educate, and so on.

This week marks exactly six months since the release of The Rise of Sustainable Giving. 🎉

Over the past six months, we celebrated:

🎉 21 years of working with charities.

🎉 10 years of talking about and researching the subscription economy.

🎉 3 years of writing, researching, interviewing, editing, and publishing the book.

🎉 35 clients served at Imago Consulting.

🎉 34 people directly involved in bringing the book to life.

🎉 19 endorsements from many of the sector’s most prominent experts and leaders.

🎉 46 keynotes, panels, interviews, webinars, podcasts (and counting).

🎉 10,000+ leaders of charities reached with the message of Sustainable Giving.

🎉 Released a #1 Amazon Best Seller! 🎉🎉🎉

In less than a year, AI tools have added the equivalent of a full-time teammate to my business. All for around $100 per month. 

In Part 1 of this Wave Report –  10 Ways I’m Using AI Right Now (Part 1) – I shared five ways I’m using AI to multiply my output. It turned out to be one of the most popular articles of the year.

It confirmed something I’ve been sensing in so many conversations lately – leaders are hungry for practical, real-world ways to use AI-based tools to work smarter and lead better.

Today, I’m sharing five more — all aimed at helping you think, lead, and create with more clarity and capacity.

I grew up surrounded by the game of golf.

There are more golf courses in the Palm Springs area where I was raised than anywhere else on the West Coast – around 130. When I was in first grade, we lived near a driving range, and my friends and I used to collect the lost range balls that veered into the trees. 

My brother-in-law is a PGA-certified golf pro. I worked summers on the course, washing clubs, picking up balls off the range, and driving carts. 

I once heard a prominent psychologist make a joke that people think marriage teaches people about love, companionship, and conflict, but in reality, the most essential thing marriage teaches us is how selfish we are. 😳

He had a point. When invested in and healthy, marriage helps us grow emotionally, socially, and spiritually, helping us to become less selfish and more loving in the process. 

Have you ever found that when you look back on your life, certain patterns emerge?

I guess that’s why they call hindsight 20/20.

For as long as I can remember, I’ve enjoyed starting things.

In second grade, I wrote and hand-illustrated my first “book,” a tale of a dog and a grand adventure. I’ll never forget the first time I saw that book on the shelf of the Jackson Elementary School library. ❤️

We are designed to be in community together. To be embodied. To be present, physically, emotionally, spiritually. To belong. 

Over dinner recently with another couple, we got into a lively conversation about the influence of technology today. 

I’m generally optimistic about technology as a tool to help us improve our lives and society, but there is no denying that technology also transforms us, sometimes in negative ways.

I recently had the opportunity to join Stephen Halasnik on the Nonprofit MBA Podcast to talk about my book, The Rise of Sustainable Giving, and how the subscription economy is transforming philanthropy. 

We all know of organizations that became great, but then faltered from greatness. 

Apple computer lost its way in the late 1980s, after Steve Jobs left (the first time). 

Disney animation lost its magic in the late 1990s, going over a decade without a hit film.

Blockbuster video infamously fell in the 2000s, from the undisputed leader in video rentals to bankruptcy in less than 10 years.

What do Apple, Disney, and Blockbuster have to do with leading an effective and thriving charity in the 21st century?

A lot.

Too many quick tips.

Too many silver bullets. 

Too much advice, not enough action.

Too much information, not enough wisdom. 

Every charity leader I’ve ever worked with has at times keenly felt the sting of two truths:

1. There are too many things to do, and

2. There are not enough resources to do all of them.

We have a rich heritage of generosity in North America, dating back to pre-colonial times and the original indigenous peoples that lived in what is now the U.S. and Canada. 

By the nation’s founding in 1776, the roots of private philanthropy in the U.S. were already deep, resulting in the founding of many churches, clinics, schools, orphanages, libraries, colleges, and hospitals. 

The earliest documented case of one-to-one sponsorship dates back to May 24, 1815, when a group of missionaries to Bombay, India, penned a letter to the American Board of Commissioners for Foreign Mission (ABCFM) in Salem, Massachusetts. 

What is the difference between philanthropy and generosity?

This was a topic of discussion as I connected with charities at events in Seattle and Dallas this week, with more than 5,000 nonprofit leaders in attendance all told. 

I’ve written extensively about the generosity crisis we are seeing in the United States. I’ve also written about the role of philanthropy in society.

This week, the much-anticipated 2025 M+R Benchmarks study came out. One of the most comprehensive benchmarking reports released every year, it’s an industry phenomenon that many fundraisers look to understand the state of online fundraising. 

The results are in, and the headline is that sustainable recurring giving is driving online philanthropy. 

This week, I was reflecting on the role of the people in my life that I’ve learned from, drawn inspiration from, and admired in some way. 

In reflecting, I read through some personal journal entries from several years back. I noticed a pattern, especially in areas of struggle or uncertainty, or when making a big decision.

One of the most important things charities can do to grow sustainable giving is to create an ongoing value proposition. 

This is something I write about in The Rise of Sustainable Giving and is one of the key differences between a one-time ask and an ask for ongoing recurring giving. 

One of the mistakes I see charity leaders make is they take their best performing single gift offer – whatever works best to get one-off gifts, and they use that for their recurring giving program.

Unfortunately, the best offer that compels donors to give one-time is not the same as an offer that compels a donor to give continuously. 
Why should the donor give to the cause on an ongoing basis?

It all started with a question – what are the surprising ideas at the intersection of causes and brands?

It’s hard to believe, but we’re coming up on four years since launching the Purpose & Profit Podcast. 

I remember when my co-host, Carly, and I decided to do the show. We had known each other for several years. She knew I liked to connect charity leaders with guests and topics from outside the world of nonprofits to see what we could learn. A couple of years prior, she started pressing me, “Dave, you should do a podcast.”