Half a Million Reasons to Stop Speed-Dating Your Donors

I miss in-the-field fundraising on most days.

Though I’ve put in my time grinding through cold donor calls, crafting annual appeals, and planning events for nearly 2 decades, the idea of walking into an office or a private home, talking about an exciting project and giving a business, individual or couple an opportunity to invest in it, still excites me to no end.

Every once in a while, I’ll work with a client closely and make solicitations with them.

Last week was one of those moments.

And holy crap the “high” of walking in the door with an idea of what we could possibly get, and then receiving that exact amount, confirmed nearly immediately?

GUH. Inject that feeling right into my veins.

So, grab the strongest coffee you can find fundraising friends, because I just walked into a boardroom, pitched a project, and walked out with a cool half-million commitment in about the time it takes to order an overpriced venti cold brew.

Except — and this is the part the click-bait headline never tells you — those “35 minutes” were stacked on years of coffee meetings, awkward small talk at ribbon cuttings, last-minute seat-filling at events, and countless “just checking in” emails.

The fast yes was only possible because the relationship had been simmering in the crock-pot since the Obama Administration.

Today, I want to remind you that an “overnight success” in nonprofit fundraising is just a sexy synonym for “strategic patience.”

If you’re hustling in any perpetually under-resourced corner of the sector, and wondering if big checks still exist, lean in.

They do.

You just have to play the long game like it’s the last 2 minutes in NBA playoff matchup.

Here's the Set-Up (Spoiler-Free Version)

Because client confidentiality is more important than humble-bragging rights, let’s rename the players:

• The Sparkly Project: A nonprofit gem ready for a glow-up.

• The Pocketbook Partner: A group of humans who know exactly what we do and share the same wants and values for the community.

  
  

Our project promised more impact, bigger and better facilities, and fresher Instagrammable moments—aka everything on their strategic wish list.

When alignment is that tight, the money moves.

But only if they trust you not to squander it.

So how did we pull this off in an economy that is getting more timid by the day? Read up!

Five Tactics That Turned Our Prospect into Half a Million

1. Courtship Over Speed-Dating

   
   

Everyone wants “major gifts in 90 days.”

I want a unicorn that poops Skittles.

Neither exists.

A lot of fundraising experts will serenade you with the idea of “dating your donors” and developing your supporter relationships like picking a spouse.

I’m no different, really.

Though my donor solicitation descriptions are a little more “Fifty Shades of Grey” than “Chicken Noodle Soup for the Donor’s Soul.”

But projects that intrigue businesses and individuals are audacious and sexy, rather than nice-guy-vanilla.

This project logged serious mileage building credibility: impact updates after their smaller gifts, invitations to behind-the-scenes tours, and the occasional “thought you’d like this article” texts.

Consistency beats charisma-only every time.

And if we’ve learned anything from E. L. James, it is that taking it a bit slower might feel like torture to you but for the donor? Pure pleasure.

2. Mission Matchmaking

   
   

Here’s the deal. No one has to give to your organization. You don’t have enough insider secrets to play hardball with their checkbooks.

Event more-so, your goal is not to just catch any human with money laying around and only get the cash they have on them at the moment. Your goal is to find that perfect fit for your mission, vision and values.

We didn’t drag our potential donor into our sandbox and shout, “Fund us!” We studied their strategic plan like it was a Marvel-movie post-credits scene, then showed how our project solved their goals.

It was as if we had psychic powers…except our psychic powers just involved doing a bit more reading, researching, and asking better questions.

Knowing we were going to be partners, not just a place to move funds from one checking account to another, made all the difference.

Pro tip: Highlight where the Venn diagrams overlap. It shows the partnership potential, plus, you get to use a Venn diagram.

And how many times in your life do you get to go home after a long day’s work and brag to your kids about how you used mathematics?

3. Pre-Game the Pitch

   
   

I love magic tricks.

My guilty pleasure, after I doom scroll OnlyFans for Middle Managers - aka LinkedIn - is finding street magician videos and watching random people run away like they just saw a ghost after their card is revealed inside some random object or pocket.

It would be incredible to elicit a reaction to your solicitation from those you were asking for money if they were so excited they bolted from their seats and sprinted away from you, but “Mystery presentations” are for Vegas performers, not fundraisers.

Before the formal ask, we soft-pitched to the organization’s leadership, built up local champions to throw their support for us, answered all the finance nerd questions, and tweaked numbers so the decision-makers knew exactly what was coming.

By meeting day, we weren’t introducing an idea; we were finalizing a partnership.

4. Paint the Future in 4

   
   

Stats are nice, but stories with sensory details light up the donor brain.

Donors may like a project, or enjoy the idea of a nonprofit, but in order to lock them in, they need to feel as if they are an actual part of your mission and impact.

We helped them see that a crystal-clear path of what their gift made possible.

Take the time to create the story. Sell a vision, not a room or sponsorship level.

Every fundraiser I know wants to reduce the amount of time they deal with paperwork, spreadsheets and logistics and get to meeting with other super cool humans to tell stories with.

So don’t waste an opportunity of getting in front of a donor prospect and forget the most important part: getting them to be excited about the part they are about to play.

Makes all the difference

5. Ask Like a Grown-Up

We requested $750K with our shoulders back, voice steady, and slides that screamed “ROI” louder than a kid all jacked-up on Halloween candy.

They countered with $500K.

Did I cry about the missing $250K?

Nope—I fist-bumped everyone in sight, because a stretch-level “yes” beats a fantasy-land “maybe” all day.

Yes, I love the idea of Fundraising Like a 5th Grader – but when it comes to making a big ask, put your big kid pants on, match the language and vibe of the other adults in the room, and get right to it.

There’s a confidence about asking for what you want, and a partnership in allowing those you are soliciting to express their desires for what they need.

Your middle ground makes for a concrete base from which you get to launch gratitude, excitement, and lay the foundation for future gifts.

Ready to replicate the magic? Here’s your training plan:

• Audit Your Friend Zone: List partners whose mission statements rhyme with yours. Rank by alignment and existing rapport. Spoiler: cold calls don’t cut it for six-figure gifts.

  
  

• Schedule Unsexy Touchpoints: Monthly check-ins, birthday notes, forwarding articles relevant to their goals. Boring? Yep. Effective? Also yep.

  
  

• Map Their Strategic Plan: Grab a highlighter like you’re back in college. Wherever their priorities overlap with your needs, you’ve found talking-point gold.

  
  

• Craft a Cinematic Case: Slide decks are fine, but bring visuals, testimonials, and a dash of sparkle. Make them feel the FOMO of not funding you.

  
  

• Practice the Ask Aloud: In the shower, to your dog, or to that barista who already knows your order. Muscle memory prevents mumbling when the stakes are high.

If you’re staring at a balance sheet that looks like it’s been on a crash diet, remember:

• Big money isn’t allergic to art, culture, or quirky community causes. It’s allergic to sloppy alignment and vague impact.

  
  

• Slow burn over flash fire. Relationships mature at the pace of a nice Pinot, not a microwaved burrito.

  
  

• “No” today can be “Hell yes!” later. Rejections are data points, not personal indictments. File the feedback, nurture the bond, circle back when the stars realign.

  
  

• You are not an inconvenience. Your mission is a gift to donors who crave purpose as much as profit.

  
  

Someone out there is waiting to partner on your audacious dream—whether it’s a building, a program or direct support individuals.

But let patience do its sneaky magic.

Now go schedule that coffee and make the next “35-minute miracle” years in the making.

Your future half-million-dollar partner is already Googling “impactful local projects” somewhere—give them something binge-worthy to find.

Ready to test-drive these tactics? Hit reply with one partner you’re courting, and I’ll send back one idea you can use this week.

You got this!

-Patrick