[Humor] 10 Strategic Fundraising Principles

[Humor] 10 Strategic Fundraising Principles

Fundraising—it’s part charm offensive, part emotional trapeze act, part caffeine-fueled chaos. Some days you feel like a philanthropic superhero, and other days you’re crying into your donor database while searching for the ‘undo’ button. But you don’t have to go it alone.

Enter the Rainmakers: the mythical, magical, magnificently strategic fundraisers who know how to play the long game—with flair. What’s their secret? These 10 fundraising principles. We’re talking about donor stickiness, connection asks, custom everything, and enough ‘You’ language to make even Shakespeare blush. Strap in, folks. You’re about to take a rollercoaster ride through fundraising best practices—Robin Williams style.

1: Build sticky relationships

Relationships aren’t just for dating apps and sitcoms. In fundraising, they are everything. Picture this: you donate $5,000 to a nonprofit. You’re feeling warm, fuzzy, and generous. Then… silence. For a year. Until they hit you up for another $5,000 like a long-lost cousin who found your name on a yacht registry.

Rainmakers never let relationships go stale. They know donors need TLC—not just ATM codes. Learn about your donors. Ask about their kids, pets, and vacation plans. Send them holiday cards with glitter. Okay, maybe skip the glitter—but never skip the connection.The stronger the bond, the stronger the giving. People give to people they trust, like, and occasionally share an awkward gala dance floor with.

2: Make a “connection ask” first

Asking for money before you’ve built a connection is like proposing on a first date—bold, confusing, and often followed by rejection. So start slow. Invite potential donors to your open house. Give them a tour. Ask them to volunteer at an event. Let them see your mission in action before you pass the hat.

This is the 'connection ask'—a no-pressure way to build a bridge from curiosity to commitment. Once someone has seen the sparkle in a child’s eye or helped sort boxes of donated glitter unicorn backpacks, they’re far more likely to open their wallet next time around.

Pro Tip: Never underestimate the power of a cookie table and a passionate program tour.

3: Increase the number of face-to-face asks

Sending emails is efficient. Mailing letters is fine. But if you want results that would make your board gasp with joy, ask in person. Always. (Okay, 90% of the time.) Rainmakers spend up to 50% of their time doing face-to-face asks. Why? Because human connection is persuasive. Because you can read the donor’s body language. Because you can spill your coffee in a charming, memorable way that no email can replicate.

In the next year, triple your number of in-person meetings. Go on coffee dates, host lunch meetups, throw porch parties. Not only will your results soar, you’ll burn off all those gala hors d’oeuvres.

4: Find and keep more donors

Repeat after me: 'Retention is cheaper than acquisition.' Say it like a mantra. Tattoo it on your fundraising arm.It’s tempting to chase new donors like you’re swiping on Tinder. But what about the ones already in your corner? What about Mildred, who gave you $200 last year and baked cupcakes for your 5K?

Keep your current donors happy. That means thank-you notes that don’t sound like receipts. That means updates that tell them their gift helped rescue penguins or fund art therapy. Of course, always keep searching for new donors—just don’t ghost the ones you already have. Even the small ones might one day drop a major gift in your lap like a fundraising fairy tale.

5: Get donors involved

Want donors to care more? Give them something to do. People don’t fall in love with nonprofits by reading mission statements—they fall in love by rolling up their sleeves and getting dirt on their pants and under their nails. Involvement = investment.

Invite donors to volunteer, join a committee, host a dinner, emcee your gala, or just taste-test your event desserts (crucial role).The more connected they are to your work, the more likely they are to donate, and the more likely they are to bring their friends along like a nonprofit pyramid scheme—but in a good way.

6: Personalize and customize everything

Nothing says 'I barely know you' like a generic thank-you letter printed in Comic Sans. Donors want to feel like VIPs, not names on a spreadsheet. Rainmakers go the extra mile: handwritten notes, customized videos, personalized greetings. Mention their dog. Compliment their hat. Send them a birthday card with a llama on it.

Whatever you do, make it genuine and delightful.The bigger the donor, the more you customize. But even small donors deserve sparkle. Think quality over quantity—and never ever mass email on a Monday morning with the subject line: 'Dear [First Name].'

7: Just Ask!

Cue dramatic music: this is the big one.Rainmakers don’t sit around waiting for the 'right moment' or the alignment of Venus and Mars. They ask. Clearly, confidently, and often while maintaining eye contact and breathing like a normal person.

The stats don’t lie: 70% of people say 'Yes' when asked in person. 90% if they’ve already volunteered. So quit rehearsing. Quit editing that email for the 19th time. Just ask. Then pause. You’ll be amazed at what happens during that pause. (Hint: good things.)

8: Focus on the needs you fill

Here’s the deal: Donors don’t care about your broken copier or your outdated filing system. They care about kids learning to read, homeless veterans getting meals, and bees finding homes.

So don’t say, 'We need money to buy laptops.' Say, 'Your gift will help 25 students improve their math scores by 40% and gain access to college-level coursework.' Talk about impact, not infrastructure. Talk about transformation, not toner cartridges.

9: Change your pronouns… use more “You”

Go grab your last appeal letter. Count the number of times you said 'we,' 'us,' or 'our.' Now count the 'you’s.' See the problem? Fundraising isn’t about your YOU. It’s about the donor. They’re the hero of the story. You’re just the helpful narrator. Use phrases like: 'You made this possible.' 'Because of you, families now have housing.' 'You are a rockstar with a checkbook.' Okay, maybe skip that last one. But you get the idea.

10: Create more goose bumps

The best fundraisers don’t just ask—they inspire. They make people cry in the best way. They create stories, moments, and visuals that give you goosebumps the size of golf balls.Don’t settle for a newsletter that looks like a tax form. Use stunning images, gripping video, and stories that stir souls. Make people feel something deep in their gut—then show them how they can help.

Can’t afford a full marketing team? Outsource it. Tap into local talent. Partner with a college media program. But whatever you do, don’t DIY your way into obscurity. Make it pop. Make it shine. Make it unforgettable.

"Great fundraising isn’t about guilt trips, sweaty palms, or soul-crushing PowerPoints. It’s about joy, connection, and making people feel like caped crusaders—preferably with a cookie in one hand and a glass of Chardonnay in the other."

Strategic Fundraising Principles! Read. Learn. Do.

About the Author

Tom Iselin has built nine sector-leading nonprofits (yes, he sleeps… occasionally). He’s written six books, sits on several boards, and is considered one of the nation’s top experts on building high-performance nonprofits. Oh, and he’s been rated one of America’s 10 best retreat facilitators—though his mom insists he’s #1. Tom is the president of First Things First, a business specializing in board retreats, strategic planning, fundraising, and executive coaching.

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