Want Your Fundraising to Get Luckier?

Lucky clover.

Jason Roberts is an entrepreneur and writer who has a simple idea he calls “luck surface area.”  It’s a useful tool for how to think about your organization’s fundraising, and here’s the gist:

The amount of good luck that comes your way is roughly equal to how much you do, multiplied by how many people know about it.

Doing × Telling = Amount of Luck  

I love this idea because it names something we all already intuitively know: the more you do, and the more you’re out there, the more things tend to happen.  (And it’s good to mention that some of those things that happen are good, and some are bad.)

This aligns perfectly with something we see in fundraising all the time: when organizations increase the amount of fundraising they send to individual donors, they receive more “unplanned” (lucky) gifts.

But there’s one thing to watch out for: you can’t just “tell” people what your organization is doing.  That results in the kind of awareness that’s not particularly valuable.  Make sure you are asking people to get involved. 

The asking is where the lucky breaks come from:

  • The donor who upgrades her gift because your e-appeal happens to land on a good day for her
  • The board member who forwards your appeal letter to a friend who’s been looking for a cause
  • The lapsed donor who comes back because you invited her to get involved
  • The major donor who finally takes the meeting because she missed the first three messages

None of those things happen if your organization stays quiet.  They only happen if your organization shows up – often, and on purpose.

(And yes, I know what some of you are thinking: “We don’t want to bother our donors.”  I’d gently suggest that your donors are less bothered than you fear, more forgetful than you’d like, and far more tolerant of additional asks than you think.  But that’s a different blog post.)

So if you want 2026 to be a luckier year for your nonprofit, that means one more email in October.  It means an ask at the end of your spring newsletter, along with a reply card, instead of a hint and a URL.  It means sending a new mailing in February.  It means picking up the phone and calling a donor you haven’t heard from in a while.

Each one of those actions is a small expansion of your surface area.  Each one is another chance for something good to happen.

Hit Songs

Hit songs.

You know the songs that were hits years ago, but you still love listening to?

Those old hit songs are what allow a band or artist to make a living making music.  Because to have a career in popular music you need at least a couple hit songs that people still love years later.

The same thing is true in direct response fundraising for nonprofits – you need a couple hits, a couple fundraising offers or campaigns that people love. 

The nonprofit equivalent of “hit songs that stand the test of time” are things like:

  • You can sponsor a child for $X
  • You can provide surgery to repair a cleft palate for $X
  • You can give a goat for a family for $X

Does your organization have a hit song you can rely on?

Are you doing the work of trying different things, paying close attention to your audience’s reaction, and looking for potential hits that people will listen to again and again?

Because your goal is not to do something “fresh and new” every time.  Your goal is to experiment, find out what works well, and then get the most out of that “hit” that you can.

And later on, you might get tired of your fundraising “hit song,” but the people giving won’t.

How to Improve

Keep trying. Keep growing.

The path to improving your fundraising in the mail & email is the same as it is to improve at anything:

  • Make lots of attempts
  • Have a tight feedback loop with good data

In tennis, want to get better at your backhand?  Hit lots of balls and pay attention to where they land.  In writing, want to get better at dialogue?  Write lots of dialog-heavy scenes, have other people read them and give you feedback.  

In fundraising, want to get better at the mail & email?  Send lots of appeals and reports, then review your response rates, your net revenue, and your retention rates.

Remember, your fundraising is just as important as your programs.  Your nonprofit has two jobs, and both must be done or you don’t have a nonprofit any longer:

  1. Deliver programs that solve a societal problem
  2. Inspire and retain supporters to fund the programs

If you want to scale past a few hundred donors, it’s highly likely you need to get good at using the mail & email.  Which means your best bet is to make lots of attempts with a tight feedback loop.

‘By November, your year-end cake is already baked’

Bake a cake.

At last year’s Storytelling Conference, Chris Davenport shared storytelling advice from successful movie directors.  Here’s one of my favorite things he highlighted:

“What an audience feels at the end of the movie is entirely dependent on what they felt earlier in the movie.”

Here’s the parallel to that in fundraising:

How much you raise at the end of the year is dependent on the fundraising you sent your donors earlier in the year.

Here are some examples:

  • If a nonprofit has shown up often in donors’ lives throughout the year, with relevant content, its year-end campaign will raise more.  The organization has earned its place to be one of the organizations a donor thinks of at year-end.
  • If a nonprofit has not done any fundraising for several months, its year-end campaign will raise less.  Because it disappeared for months, the organization is less top-of-mind for donors and won’t receive as many gifts.
  • If a nonprofit has made it clear through the year that its work is needed, its year-end campaign will raise more.  The organization has made it clear that it’s working on something important, and donors tend to support causes and organizations that they feel are important.
  • If a nonprofit has spent the year only talking about how well things are going, it will raise less at year-end.  The organization has shared only success stories, so it sounds like things are going great and help isn’t really needed, thank you very much.

A friend of mine put this memorably.  He used to run the annual fund for a national nonprofit you’ve heard of.  Over beers one night he said,

Look, by November, your year-end cake is already baked.  All that’s left to do is see how it turns out.”

What he meant was the fundraising you do throughout the year has a large effect on how well your year-end campaign performs.  (You can, of course, have a strong year-end campaign without communicating much during the year.  But a strong year-end campaign after a strong annual campaign will raise even more.)

I share this here in January so that, as you’re creating your fundraising this year, you set yourself up during the year for the best year-end campaign you’ve ever had.

Pie and Sisyphus

Downhill walk.

To repeat one of the best lines I’ve ever heard about fundraising:

Fundraising is like a pie-eating contest where the prize for eating the most pie is that you’re asked to eat more pie.

“You raised 4% above projections this year,” the Board says, “let’s aim for 6% over projections in 2026!”

It’s kind of like Sisyphus, doomed to push a boulder up to the top of a hill but always having it slip from his grasp before reaching the top.

But there’s an unsaid part of the Sisyphus myth that was pointed out to me a few years ago: each time the rock rolls back to the bottom of the hill, Sisyphus has a restful, unencumbered downhill walk before he starts again.

So today – when the appeals have been sent, the calls have been made, the emails for today and tomorrow already programmed and ready to go – I hope you are enjoying your “restful, unencumbered downhill walk” as all the money comes in.

Enjoy your walk, and happy new year!

How Things Work

Owner manual.

I’ve always liked to understand how things work.

Engines, supply & demand, how plywood is made, you name it.

Early in my fundraising career, when looking at detailed fundraising results, I noticed the following three things that go a long way to explaining how mass donor fundraising works:

  1. Appeals raise more than stewardship pieces.  OK, great.  An appeal is the best thing an organization can do increase revenue.  And if an organization wants to raise more money, its annual plan should prioritize sending appeals.  Appeals are also great at getting donors to give again, which is the definition of “retaining” a donor.
  2. Stewardship pieces increase donor retention.  Great.  We need to make sure that every annual plan has some stewardship pieces – but need to remember that they raise less than appeals.

The immediate next question is, “What’s the right mix of appeals to stewardship pieces?”  Back to the fundraising results I went.  I looked at the nonprofits who were out-raising similar organizations while also retaining a high percentage of their donors.  And that’s when I noticed:

  1. The organizations that had the healthiest mix of Revenue and Donor Retention sent roughly 2 appeals for every 1 stewardship piece.  The 2:1 ratio maximized their revenue & impact today, while also retaining donors so that next year went great.

I’ve used that rough ratio successfully for hundreds, probably over a thousand nonprofits since then.  It keeps on working.

(It is, of course, a little different in a major donor context where you are in relationship with the donor.  The 2:1 ratio does not apply.)

Here’s one of the things all this makes you realize: you can over-steward your mass donors, and there are real negative consequences to doing so.  If a nonprofit over-stewards its mass donors, it raises less money in the short term and retains fewer donors in the long-term. 

Think of stewardship as “planting seeds” and appeals as “picking the fruit.”  If you plant a lot of seeds, but don’t pick the fruit very often, you have less of a harvest than you earned.  Fruit doesn’t pick itself.

Interestingly, the biggest hurdle to smaller nonprofits sending out more appeals is emotional resistance.  People cannot believe the 2:1 ratio is correct.  They don’t enjoy sending appeals.  They can’t believe that donors enjoy giving in response to appeals.

That’s why much of Better Fundraising’s work is sitting with nonprofit leadership, talking to stakeholders, sharing examples & stories, and helping them be comfortable trying one or two steps of a different approach.

If you’d like to have that conversation, let’s chat.  It’s what we do.  You do the dreaming about the impact you could have if you raised a great deal more in 2026, and we’ll help you have the conversation and start raising more money and retaining more donors!

It Can Be Hard to Change Your Ideas about Fundraising

Self-reflection.

I wrote a couple days ago about how smaller nonprofits must often create fundraising messages that they don’t prefer for their fundraising to be more successful.

Today, I want to take a moment to acknowledge that changing your ideas about fundraising can be emotionally difficult. 

For a Founder, or for someone who is passionate about their fundraising, it can be a very real struggle to try a fundraising message or strategy that doesn’t personally resonate. 

Let me share my own experience with this, in hopes that it’s helpful. 

Here’s the thing to know about me: I strongly prefer not to make mistakes.  In fact, I hate mistakes.  I fear being wrong.  I fear being judged.

My fear around avoidable mistakes has positive consequences – for instance, it made me a fantastic student.

But it also has negative consequences.  For instance, I’m occasionally a pain in the neck to work with.

So it was challenging for me when I learned that the easiest way for smaller nonprofits to raise more money is to send out more fundraising.

Wait, I thought, wouldn’t the best way be to make each piece of fundraising more perfect?  We’ll eliminate all the mistakes, get everything up to best-practices… wouldn’t that bring all the money in?

Nope.  I saw again and again that the nonprofits that grew their individual donor fundraising the fastest were seeing that “showing up regularly in donors’ lives” is more important than “showing up perfectly in donors’ lives.”

It didn’t seem possible that “sending more fundraising” could work.  It didn’t seem possible that the occasional typo or “wrong thing showing through the envelope window” could work.

But if I’m honest, the real conflict was with my personal preferences and fears.  I was thinking, If we have to move faster we’re going to make mistakes.  I don’t want to focus on the total number of pieces, I want each piece to be an un-critique-able jewel box of fundraising brilliance.  <<pounds podium>>  I’m a copywriter and a storyteller, dammit, not some cheap content machine! 

I’m poking fun at myself here, but my feelings of discomfort were real.

And you’ll smile at why my thinking on this issue eventually changed; I saw the strategy of “showing up regularly is more important than showing up perfectly” succeed so many times for so many organizations that eventually I realized I would be making a mistake if I didn’t change my thinking.  And you know I don’t like to make mistakes.  Sheesh.

Anyway.  I still don’t prefer the “showing up regularly is more important than showing up perfectly” approach to mass donor fundraising.  But I embrace it because it so obviously helps small nonprofits raise more money and increase donor retention rates.  And because making the world a better place is more important than my own personal preferences and fears.

So… acknowledging that we all have preferences and fears… and acknowledging that doing things in a non-preferred way can be difficult… is there anything about your organization’s fundraising that should be changed in order to raise more money and fund more work, even if you don’t prefer the change?

The Habit

Habits

There’s a habit your organization can develop that will result in raising more money and keeping more of your donors each year.

It’s the habit of regularly using the mail and email to stay in relationship with your donors.

Here’s why the habit of regularly sending mail and email to your donors is so powerful…

The habit of regularly Asking your donors to do meaningful, powerful things with a gift through your organization results in more gifts. Donors in motion tend to stay in motion. Donors at rest tend to stay at rest.

The habit of regularly Reporting to your donors shows and tells them that their gifts make a difference. Donors who know their previous gift made a meaningful difference are more likely to give to you again than donors who don’t.

The habit of regularly contacting your donors always works better than “going dark” for weeks or months at a time.

The habit of regularly contacting your donors via letters and emails is more effective than Social.

The habit of regularly contacting your donors always works better than sending nothing.

Getting in the habit of regularly sending out mail and email, paying attention to the results, always works better than any other approach.

It’s a habit you must develop

First, you must get past the idea that mailing your donors more than a couple times a year will somehow result in the mythical “donor fatigue.” If you need help with that, look here. Or here.

Then you have to realize that each piece you send out is not precious. Each piece you send out is an overwhelmingly positive incident that raises money, keeps you in touch with your donors, and is a learning opportunity.

Then you just have to practice. You need repetition. Sending out mail and email is like any other skill; you get better with practice.

Show me an organization that has developed a habit of regularly mailing and emailing its donors and I’ll show you an organization that has deeper relationships with its donors and keeps more of its donors every year.

This post was originally published on January 7, 2021.

Take More Steps

Steps progress.

This post is the first in a series of special posts for January.  Last year we kept track of the ideas that had outsized impact on the small and medium-sized nonprofits we serve.  Each of the posts this month is about one of those big ideas.

I hope they are helpful as you think about your fundraising this year.

***

Every piece of fundraising you make & send is a step on your journey to raising more money.

Here’s the simple truth: the more steps you take each year, the closer you are to raising more money, because you get better when you practice.

You know those organizations that send out 10 appeal letters, 6 printed newsletters, and 50 fundraising emails?  They can do that because they’ve practiced so much that their fundraising works great.

They don’t have different donors than you.  They don’t have a better cause than you.  They’ve just practiced more.

At some point in the past, someone at those organizations said, “Let’s figure out a way to make and send more fundraising.”

If your organization needs someone to say that, you can be that someone.

Don’t be afraid of making & sending more fundraising.  The more steps you take, the better you get at taking steps.