Fundraising is a Pie-Eating Contest

Pie eating.

It’s the best line I’ve ever heard about fundraising:

Fundraising is a pie-eating contest and the prize for the winner is… more pie!

Feels true, doesn’t it? You have a great fundraising year, and the result is that you’re asked to raise 7% more the next year.

It’s a great, crazy job we have.

My hope for you is that you ate a lot of pie this year, and you get a few days off to enjoy it.

Enjoy your holidays… more pie awaits!

Imagined Constraints Can Lead to Real Revenue

Boy in a box.

The following is a guest post from Mike Duerksen of Buildgood in Canada.

The exercise he proposes is a GREAT way for your organization to uncover (quickly, in my experience) actions you can take next year to help you raise more money and keep more of your donors.

Think of the exercise as making your fundraising healthier & more robust and increasing your organization’s immunity to difficulties.

The little boy isn’t limited by the shape of the cardboard box.

Yesterday it was a secret cave. Today it’s a plane flying through the skies. Tomorrow it might be a pirate ship.

His only constraint is his imagination, not the four walls that box him in.

And that’s the power of constraints: they force creativity.

Right now your nonprofit might be in a cardboard box. And you feel stuck. And you’re waiting for the day when the walls come down again.

But what if the pandemic is giving you a rare chance to think creatively about how you can free yourself of the ways you’ve always done things?

What if you can use the new limits imposed on you to re-imagine the ways you show up in the world?

And what if you can actually improve your fundraising and future-proof your revenue to protect yourself from the next crisis?

Chances are you can…by playing a game of constraints.

What Is A Game Of Constraints?

A game of constraints is a simple exercise where you imagine a scenario that might seem impossible or unlikely.

Then you brainstorm as many ways as possible to overcome the problem.

You’ll be surprised how quickly you can free your mind from thinking:

  • “We can’t do that!” to
  • “This is tough, but maybe not impossible” to
  • “Here’s one way we could respond that would solve the problem”

You can have a lot of fun playing these games and stretching your imagination. But you’ll also feel energized about the opportunities ahead.

You’ll be more confident in your ability to solve potential problems. And you’ll identify where you are weak today, so you can become more resilient for tomorrow.

Ready to play some games?

5 Games You Can Play Today

Here’s a few scenarios to get you started…


Imagine a world where the postal service is no longer operating. From one day to the next, you can no longer reach your donors by mail. How will you communicate with them?

This is a great game to start with because we have seen postal strikes before. And when COVID hit, some print houses weren’t sure at first if they would keep operating

Chances are the options you came up with were to email, call or use social media to reach your donors.

Now ask yourself: How many emails do we have on file? What’s our email open rate? How many phone numbers? How many cellphone numbers? What do we need to do today to make sure we increase emails and phone numbers on file?

What you’ll discover: You likely need a better strategy to harvest donor email addresses and phone numbers.


Imagine a world where you are no longer able to host any fundraising events in person. How do you engage current donors so they feel like they are still part of a community of givers? How do you attract new donors? What tools or approaches do you use instead?

This one hits close for many nonprofits right now. Some are finding success (and profitability!) moving to online formats.

Others are discovering that simply moving your event online is not a sound strategy — you have to re-invent the entire experience.

And some are letting go of events altogether, replacing them with something else.

What you’ll discover: There are many ways to draw donors closer to your mission outside of special events that may yield higher net revenue, save you time and give your donors a greater sense of connectedness.


Imagine a world where you can no longer get funding from public and private foundations, governments and other institutional funders. How will you raise your yearly budget? How much more will you need to raise from individual donors? How many more individual donors do you need to get there?

This is one of the most important games you can play if you rely on applying for large grants and government funding every year.

Priorities for funders change. Governments change. Key relationship players at foundations change.

Don’t wait until you are denied funding before creating a strategy to diversify your income.

What you’ll discover: You may need to invest in your individual giving program a lot more in the coming years to protect your mission from future volatility.


Imagine a world where the largest gift you can secure from anyone is $10,000. How many $10,000 donors would you need? How many $5,000 donors? Or $2,500? How would you identify who in your donor file can upgrade to give close to $10,000? How would that change the way you treat your donors?

Some organizations are getting the highest gifts in their history right now. Others are seeing major donors sit back a bit while they evaluate the situation.

Meanwhile, foundational donors — those in the “mass” file — are stepping up. Many just needed to be challenged with a clear and urgent problem to solve.

What you’ll discover: You likely have hidden value in your middle donor file — and you likely need a strategy to help each donor in your mass file give the best gift they can.


Imagine a world where you can no longer acquire new donors. All you have to work with is your existing records in your database. How will you ensure your active donors don’t lapse? How will you convert your loyal donors to monthly givers? How will you upgrade your active donors to middle donors? How will you upgrade your middle donors to major donors? How will you re-activate your lapsed donors?

The point of this game is to help you realize that you can grow the value of your current donor file. You just need to pay some attention to the donors you’re at risk of losing.

Because the donors you already have are a lot more valuable than the ones you hope to acquire.

After playing this game, you’ve probably identified a few ways you can become a smarter fundraiser using the resources at hand.

What you’ll discover: You have a lot of room to improve your donor retention, and win back donors who haven’t engaged in a while.

Your Next Steps: Play A Game With Your Team

Now it’s your turn.

  1. Pick one of the games above. Or create your own scenario. Then gather your team.
  2. Split into smaller groups and brainstorm. Make sure each person knows there are no bad suggestions, as long as they stay within the given constraints.
  3. Share your answers. Have each team read out their answers to each other.

What you’ll end up with is an invaluable source of raw ideas that will help you uncover better ways to serve your donors, make your fundraising more resilient and position your nonprofit for growth.

And you’ll notice your mindset will shift.

You’ll feel more prepared to meet this moment in time. You’ll be more optimistic about your ability to raise funds.

You’ll start to see the cardboard box you’re in not as a limitation, but as an opportunity to create something new.

And you’ll feel more confident that you can emerge stronger…thanks to the power of constraints.

Big thanks to Mike for letting us share his post with you. And if you’re interested in more from Mike, here’s a link to his podcast that’s focused on practical fundraising tips and strategies.

The Master of Monthly Giving


The following is a guest post from Erica Waasdorp of A Direct Solution.

Erica has more experience at every level of monthly giving than anyone I’m aware of. Big orgs, small orgs, programs just starting, you name it, Erica understands how it works and knows what to focus on next.

I’m sharing her post below because of the list in the middle. Regardless of whether you’re thinking about starting a monthly giving program or you have a thriving one, if you read the list you’ll find at least one actionable thing you can do to help your program work a little bit better.

During a recent webinar, someone asked me: “Does the timing of the launch of your monthly giving program make a difference? Are there certain times of the year that are better to start a monthly giving program?”

My answer is twofold:

If your organization is really gung-ho about monthly giving — as in, you almost care more about generating sustainers than one-time gifts — then by all means, go for it!

There is really no bad time to launch your monthly giving program. HOWEVER, it’s crucial that you have everything ready before you launch.

If you don’t have the people or the time to prepare, please do yourself a favor and hold off for a bit. Year-end is a busy time, so the last thing I’d want to do is add any more stress to your plate.

Knowing how you are probably as busy as a one-armed paper hanger, here’s what I recommend you do instead:

Just focus on getting as many one-time gifts in now during the year-end giving days — Giving Tuesday, holiday giving, etc. Then take one hour a week during the next two months, and chip away at getting everything ready for a launch in January.

Print out this list and just cross off each item as you go along:

  1. Decide who’s going to be responsible.
  2. Add monthly to your one-time donation page, if it’s not there already.
  3. Create a monthly giving page if you don’t have one already.
  4. Link the monthly giving page to other areas of your site and the pull-down menu.
  5. See how the monthly gift will flow into your database.
  6. If you can do pop-ups on your one-time giving page, create a pop-up to convert someone to give monthly.
  7. Create the thank-you landing page/auto-responder, emails, direct mail, etc.
  8. Create a letter to send out as a special invitation to those donors who gave at year-end.
  9. Create a few emails to send out in January, inviting your email names to give monthly.
  10. Create a special part in your homepage slider to link to your monthly giving page.
  11. Create a launch email to send to your board, staff and volunteers first thing January, so everybody is aware of it.
  12. Test everything before you go live!

If you just cross off the items on the list above, you’ll be ready to launch come January. What a great time to ask the donor to help 12 months a year.

Don’t worry too much about benefits or names if you think that’s going to take too much time; you can always add that later. The key is to ask your donors to give monthly first and make sure the recognition email and letter are in place. Send those right away. It’s always OK to “surprise” your monthly donors later with a special benefit. They’re getting the big advantage of feeling good by making a difference in a way they can afford.

Erica recently published a book on monthly giving and it’s brilliant. Here’s where to get it on Amazon – I can personally vouch that what she shares in the book will help you acquire more monthly donors, keep them for longer, and increase their lifetime values. It’s that good!

Optimistic or Pessimistic?

Think positive.

Organizations that are optimistic about their fundraising are more likely to raise more money than organizations that are pessimistic about their fundraising.

It’s a classic case of how beliefs shape actions, and then actions shape results.

Beliefs Shape Actions

If an organization is pessimistic, you think “we don’t want to overwhelm our donors” so you don’t send a second year-end appeal or follow-up emails. Because of this, all the people who didn’t see your first appeal, and all the people who might otherwise give you another gift, don’t get the chance.

If an organization is pessimistic, you think “everyone is doing Giving Tuesday and donors’ inboxes are overwhelmed” so you don’t participate in Giving Tuesday. Because of this, your donors who thought of you on the morning of Giving Tuesday and would have loved the chance to help… don’t.

If an organization is pessimistic, you think “if a major donor hasn’t given a gift by this point, they probably aren’t going to.” Because of this, instead of calling all the major donors who haven’t given a gift yet to give a friendly reminder and providing a very real service to many donors, organizations move their focus on to other things.

Actions Shape Results

If you’re optimistic at year-end and mail two printed appeals, you’ll raise more money and retain more donors than if you send just one appeal.

If you’re optimistic at year-end and participate in Giving Tuesday, you’ll raise money from donors (and non-donors!) who like to give Giving Tuesday gifts.

If you’re optimistic at year-end and call all of your major donors who haven’t given a gift yet, you’ll receive many gifts and have conversations with donors who tell you, “Thanks so much for calling! It’s been a crazy year and I hadn’t gotten to sending you a gift yet, so I appreciate it!”

All of which result in raising more money.

Beliefs Drive Tactics

My point is that an organization’s beliefs – the “stories we tell ourselves” about fundraising and donors – determine the shape and boundaries of the organization’s fundraising programs.

Of course, human resources, cash on hand, knowledge about how to set up a giving page, all of those very real variables also affect fundraising programs.

But in my experience, beliefs are the primary strategy-setters and boundary-creators.

So this year-end, are you optimistic or pessimistic? That will tell you a lot about how you can expect your next 6 weeks to go.

If, after reading this, you decide to be more optimistic, it’s not too late to:

  • Mail a second year-end appeal
  • Send out three emails on Giving Tuesday
  • Call major donors who haven’t yet given a gift this calendar year
  • Ask Board Members who haven’t give a gift yet this year to give so that you can enter next year saying that your organization has 100% Board participation
  • Send out three to five emails on the last three days of the year

You can use optimism as a tool to help your organization raise more money and do more good.

Long Emails vs Short Emails

Many emails.

Here’s a bit of fundraising wisdom found in an unexpected place.

It’s from a musician named Gabe Anderson who is writing about emails that musicians send to their fans. But what he’s saying absolutely applies to a nonprofit’s email strategy:

Shorter emails, sent consistently, sustain connection much better than one long one every few months.

Packing an email with links and offers and stories and updates and discount codes is too much… all under the idea ‘we’ll make up for our lack of consistent communication by sending out an email that includes everything because it’s really important that they know everything.’

The solution is to send more emails… to people who look forward to getting emails from you… and then don’t overwhelm them with long paragraphs and links.

You don’t usually enjoy getting long emails either.

The lesson, as always: never go dark. It’s a generous act to show up regularly in your donors’ lives!

h/t to Josh Alcorn for the idea for this post.

Crossing the Chasm

Messaging Approach

There’s a surprising parallel between fundraising and selling technology products.

I found it in Geoffrey Moore’s famous book from 1991, Crossing The Chasm.

The graphic above is a direct “translation” from a graphic featured in the book. Except in this case I’ve made it about fundraising, not about selling tech products.

One of the main theses of the book is that the messaging used to attract “early adopters” will not work well when trying to attract what’s called the “early majority.” And technology companies miss this all the time because the company itself is filled with experts and early-adopters.

Sound familiar?

Doesn’t that “rhyme” with how the messaging nonprofits use in the early years does not work well when trying to achieve their next level of growth? And how nonprofits miss this because the nonprofit itself is filled with experts?

I know the graphic above takes some thinking about, but I’ve never seen a clearer picture that illustrates how the donors at your organization’s next stage of growth are different than your current donors – and therefore will likely require different messaging and tactics to be acquired.

Of course, this isn’t true for all organizations. But in my experience it’s true for a) smaller organizations who aren’t growing as fast as they’d like, and b) organizations whose growth has plateaued for many years.

If you think your organization is having a hard time crossing the chasm, keep reading this blog and check out Work Less, Raise More. The copywriting practices and communications strategies we help you with are exactly the types of things that help organizations cross the chasm.

And if you’d like Better Fundraising’s help crossing your chasm, take two minutes to fill out this form! We’d love to chat.

Remember: your organization is perfectly designed to raise what you’ve raised this year. If you’re looking for breakthrough growth, you’re probably going to have to start doing something different. And recognizing that is the first step.

The stories you tell yourselves about fundraising are more important than the stories you tell your donors

Bend the arc.

The stories that matter most in your fundraising are not the stories you tell your donors.

The stories that matter most are the stories your organization tells itself about fundraising.

Every organization has a set of beliefs – a set of stories that it tells itself – about fundraising, and donors, and money.

Most of those stories are based on personal experience. On our own upbringings and relationships with money.

And – you know this – some beliefs about fundraising result in organizations that raise a ton of money and accomplish a ton. Some beliefs about fundraising results in organizations that raise less than they could and accomplish less than they could.

I’m thinking about this because I’m getting ready for the Storytelling conference next week.

People who attend or watch the videos are going to learn so many proven tips, tricks and tactics… and be excited about trying them at their organization… and then won’t be able to because the organization won’t like them. Because the proven tips and tactics are in conflict with the stories that the organization tells itself about how fundraising works.

See how the stories your organization believes about fundraising have a direct effect on the tactics and strategies your organization will use in fundraising?

It’s that very thought that caused me to draw the doodle at the top of this post. It’s the “stories the organization tells itself” about fundraising that make the difference between an organization that grows a little… and an organization that can grow a lot.

For example, here are a handful of the “stories” that I’ve seen result in greater-than-normal fundraising growth:

  • A majority of our donors would love to give multiple times per year
  • Helping donors see and feel the Need is part of why our organization exists
  • Our messaging needs to resonate with who we’re sending the message to, not with us
  • Different groups of donors require different messaging; a grant application is different than an e-appeal
  • Each piece of communication will be more successful if it only has one job
  • We’re open to messaging that doesn’t “sound like us”
  • Let’s get great at proven tactics before we try to innovate
  • If we aren’t getting enough “no’s” then we’re not asking enough
  • If we aren’t regularly having major donors give less than what we ask for, then we’re not asking for high enough amounts
  • It’s a generous act to show up regularly in donors’ lives

Think about your organization for a second. If your organization told those stories to itself, would it result in you doing fundraising differently?

Because from those stories would come different plans and tactics. For instance, if you believe most of your donors would love to give multiple gifts per year, you create an annual plan that gives donors the opportunity to give multiple gifts per year.

Bend the Arc

As I look back at the graphic at the top, it makes me think of the quote by Dr. Martin Luther King, Jr.:

“The arc of the moral universe is long, but it bends towards justice.”

Every organization’s fundraising has an “arc.” It’s bending up or down. A lot or a little.

And believe it or not, the “stories your organization tells itself” have a lot to do with the trajectory of your fundraising arc.

So I hope you’ll examine the stories your organization is telling itself.

  • If you want to try something new but your organization doesn’t want to, I hope you’ll ask, “What beliefs do we have that result in liking or not liking a tactic?”
  • Then ask whether that belief is helping or hurting the organization in this instance.
  • And ask whether there’s an alternate belief you could try.

If you’ve been on one fundraising trajectory – one “arc” – for a long time, to bend the arc your organization is going to need to change the story it tells itself.

In my experience, if you create your fundraising following the beliefs listed above, you will raise more money.

Improve your organization’s stories about fundraising, and you’ll improve your organization’s fundraising results.

How to Raise Money like an Organization that has Twice as Many Donors

Out perform.

So. You don’t have very many donors. But you want to raise as much money as those other organizations that have a lot more donors.

What can you do?

Well, if you can’t change how many donors you have, you can change how much of your donors’ attention you have.

An organization with 1,000 donors can raise just as much money as an organization with 2,000 donors IF it can earn and keep twice as much attention from its donors.

Small But Mighty

For most smaller organizations, in my experience, their “number of donors” is not the main factor that limits their fundraising.

The limiting factor is how much attention, engagement, and loyalty they earn from their donors through relevant donor communications.

So how can you increase attention, engagement, and loyalty? They are a function of your donor communications:

Donor generosity is astounding (which is one of the main lessons of the past 18 months). Trust in it. You can raise more money from your current donors than you currently are. But you must earn and keep their attention with relevant fundraising communications.

So. Want to raise money like an organization that has twice as many donors as your organization has? Click on the links above – they’ll show you how you can modify your donor communications to earn twice as much attention, engagement and loyalty.

But the first step is to believe that you can be raising more money from your current donors. An abundance mindset is what unlocks an organization’s ability to raise money like an organization twice its size!

The Recipe for Recall


My last post was a formula for how (and why) to get on your donor’s “automatic recall” list.

A formula is a concept – a helpful idea… but it’s not specific and actionable. And our goal here is to be specific and actionable.

So let’s get tactical. Here’s a “recipe” for smaller nonprofits for how to get on your donor’s automatic recall list.

The Classic Recipe

There’s a tried-and-true fundraising communications recipe used by nonprofits for 70 years that really works:

  • Regular relevant appeal letters
  • Regular relevant newsletters

The key here is the “regular” part. I’d say “regular” means at least six mailings over the course of the year, with more appeals than newsletters.

Today, organizations are layering in email fundraising in addition to their direct mail:

  • Regular relevant e-appeals
  • Regular relevant reporting stories

(Notice I’m not mentioning e-news. E-newsletters tend to be organization-focused and, while not negative, tend to be less helpful than Asks and Reports at helping donors reach automatic recall.)

The key, again, is the “regular” part. I’d say “regular” means about eight e-appeals and twelve reporting stories per year.

If you’re at a smaller nonprofit and those numbers seem overwhelming, please don’t worry. You can succeed with fewer communications. Plus, direct mail and email are only a part of your overall fundraising strategy.

That said, those numbers should give you a sense of what’s possible. Larger nonprofits communicate far more often than that, and they:

  • Raise a remarkable amount of money
  • Effectively identify new major donors
  • Experience the opposite of the mythical “donor fatigue” – they see high levels of donor loyalty

Every one of those bullet points is available to your organization. (Your donors aren’t any different from theirs.)

And if you’re sold on the idea of communicating more often, but doing so is a capacity / human resources issue, check out Work Less, Raise More. There are trainings that will help you create effective fundraising in 30 minutes.

Finally, know that the “recipe” mentioned above is a proven system in use today because it’s effective at helping organizations do two things:

  1. Raising money with each mailing (or email) so that you can do more of your mission
  2. Building “automatic recall” over time, which increases revenue over time by increasing your number of major donors and legacy gifts

You can communicate with your donors more than you think you can. It’s a habit you must build.

But it’s a habit you want to build, because donors in motion tend to stay in motion, and donors at rest tend to stay at rest.