What 8 Years of Dungeons & Dragons Taught Me About Fundraising

Last night, after nearly EIGHT YEARS, our Dungeons & Dragons campaign officially wrapped.

We celebrated in the nerdiest way possible – Trivia Night.

90’s Theme.

And we were promptly defeated by a team of humans that were literally born in the 90’s.

Highly suspicious.

But, back to D&D!

This campaign has lasted longer than most sitcoms, survived a pandemic, and out-aged my youngest child.

What started as a few grown adults sitting around a table, rolling dice and talking in weird accents while stress-eating chips and gas station snacks… became an epic saga full of plot twists, heroic deeds, and yes—some incredibly dumb decisions we barely survived.

Note: I take full credit for ALL the dumb decisions.

As I packed up my dice bag and character sheet, it hit me: this whole experience had major fundraising energy.

So, fellow do-gooders, here are five lessons from the fantasy realm that absolutely apply to your capital campaigns, annual appeals, and donor thank-you strategy.

1. Patience – It’s a Long Game, Baby

You don’t just waltz into a Fire Cult’s cave on day one. You scout. You plan. You slowly gather XP, gear, and people who actually know how to cast Mass Healing Word and can properly navigate in the dark.

Same with fundraising. You don’t build deep donor relationships overnight. And that giant campaign goal? You’re not rolling a natural 20 on your first try.

Whether you are new to fundraising or have become an impatient grizzled vet of the fundraising world – remind yourself (and your board members for that matter) often that this takes awhile.

And though you probably daydream about an immediate win or unleashing one spell to win a fight in a single turn, take a breath and a beat. You’ve got a long way to go.

Fundraising Tip: Set progress benchmarks, not just end goals. Celebrate the small wins—first $1,000 gift, new monthly donor, event registrations—like you just defeated a mini-boss.

Because you did.

Bonus Action: Create a “campaign map” to track progress. Visually showing your team (and donors!) where you are in the quest makes the journey feel real—and winnable.

2. Creativity – The Boring Choice is the Real Monster

In D&D, you can either charge in and fight the troll... or convince him you’re his long-lost cousin Barry.

Guess which one people remember?

Fundraising’s the same. You can do another chicken-dinner gala. But maybe, just maybe, you could throw a costume ball in a barn. Or a "Dollars & Dragons" trivia night. Or auction off naming rights to the office coffee machine.

Do you need to have elite persuasion skills?

It doesn’t hurt.

But more importantly, thinking outside of the Tiny House makes for a more enjoyable experience for both you, and those who show up every single day for your organization.

Fundraising Tip: Ask your team, “What’s the weirdest idea we could pull off?” Then scale it back one notch and try it.

Safe is forgettable. Creative is shareable.

Bonus Action: Create donor personas like D&D characters. “Barb the Benefactor,” “Todd the Tech Donor,” “Wendy the Wish-List Warrior.” What would they respond to? What kind of events or asks would they say yes to?

3. Determination – Stop, Regroup, Try Again (and Again)

Listen, we made terrible choices. (Ok, again…I made terrible choices.) Did my Barbarian character decide to charge straight into an interdimensional portal to attempt to destroy the bad guy?

Yes.

Did I get obliterated by what was on the other side?

Also yes.

But we always came back. New plan. New route. New strategy.

Same with fundraising. Your silent auction flopped? That mailer got zero response? You didn’t get the grant?

Cool. Now regroup. You're not cursed. You're just mid-quest.

Fundraising Tip: Debrief every event or campaign—even the ugly ones. What worked? What didn’t? What would you never do again unless cursed by a necromancer?

Bonus Action: Create a “fail folder” of past flops. Not to wallow, but to learn. Also fun to pull out when a board member suggests “just doing that again.”

4. Bravery – Is Both Rewarded and Punished

Bold moves are legendary because they’re risky. That time our rogue tried to solo the boss?

Disaster.

That time we used a potion we found in a haunted bathroom?

Unexpectedly awesome.

Fundraising isn’t safe either. That big ask you’re nervous to make? That campaign you think is too ambitious?

DO IT. Maybe you raise $500K. Maybe you raise $5K. But if you never ask, you’ll never know.

And spoiler: bravery builds trust.

Fundraising Tip: Don’t pre-reject on behalf of your donors. Let them say no. You might be surprised how many say yes if you just...ask.

Bonus Action: Use the “stretch gift” ask: “Would you consider a leadership gift of $25,000?” It’s bold. It sets the tone. And even if they counter lower, you’ve just defined what leadership looks like.

 5. Relationship Building – Your Party Is Everything

We could have had the strongest character sheet in the realm, but without teamwork, we were toast.

Fundraising is no different.

Your team—board, volunteers, donors, partners—is your party.

No one solos a campaign.

I mean, you could try – but man, is that going to be messy.

You have so much talent in your network – so many impassionate humans that want to help and use their talents to help you mission.

Also: donors are not ATMs. They’re allies. Treat ‘em like it.

Fundraising Tip: Assign a “party role” to your supporters. Who are the Champions (loud supporters)? The Clerics (quiet sustainers)? The Bards (story sharers)? Show them how their role matters.

Bonus Action: Send a “Thank You for Being in Our Party” email with a fun D&D-style title: “You’ve Been Upgraded to Legendary Supporter.” It’s unexpected and memorable—like a critical hit to the heart.

Fundraising is a campaign.

It takes guts, grit, and a dash of wizardry.

Whether you're battling donor fatigue or slaying budget dragons, remember: you don’t need a magic sword—you just need the right team, the right story, and a reason to keep rolling.

Also… never split the party.

Seriously. Don’t.

Have fun nerding out about Fundraising this week!!

-Patrick