My fun uncle passed away last week. Uncle Dan.
And I need to tell you a story about him.
Uncle Dan was a veterinarian in Tennessee. He came from a long line of medical professionals. His granddad was a country doctor who made house calls and delivered babies. His dad was a dentist who served in World War II. And Uncle Dan took up the medical mantle by working on animals.
He mostly served families in midsized towns. But he was always a country doctor at heart.
So this one time, he decided to buy a horse.
And he invited me along to help.
I was about 15 at the time.
Now normally, when a person buys a horse, they show up with a covered trailer to drive the thing home.
But not my Uncle Dan.
He showed up with a pickup truck.
And I don’t mean a big one.
This was a Ford Ranger – back when those things were just a hair bigger than a station wagon.
And he had some mild sedative, a rope, and his nephew.
So we drove out into the country to this farm where my uncle was going to buy this horse.
And we got to the farm. Bought the horse. Gave it the sedative. Laid it down in the trailer of his pickup – mildly sedated but not out cold.
And Uncle Dan looked at me and said “Bee-uhl [my name has two syllables in the south] – get on in there and hold this horse down.”
And then I literally rode in the back of this Ford Ranger, with an actual horse that was only mildly sedated, and held it in place while we drove about 45 minutes on the back roads of Tennessee to my Uncle’s clinic.
And bless its heart. The horse made it. No injuries. No damage other than some mild trauma, I’m sure.
But we both arrived in one piece – bonded by our shared ride – none the worse for wear.
And I had a fun story to tell, thanks to good ol’ Uncle Dan.
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At Major Gift Solutions we’re building a culture of fearless fundraising. And I don’t mean being heavy handed or tasteless.
And I certainly don’t mean driving horses around without proper transportation!
But I do mean cultivating a culture where our team members and our clients understand that, in order for donors to give, they ultimately need to be asked.
This can happen in a variety of ways – direct mail, a soft ask, a focused campaign, or sitting across a table from someone and asking unapologetically, “Would you support us with a gift of $XXXX?”
That’s the type of fearlessness I hope to cultivate in myself and my clients. Because that’s the type of fundraising I’ve seen move the needle for organizations.
Again, all the typical caveats included – don’t ask too quickly. Always be stewarding. Work on the relationships.
But so many times I’ve connected with organizations that had tens of thousands of dollars just waiting to be raised from donors right in their databases. Those individuals had just never been appropriately asked.
I’ve broken down a few ways you can go about that here, here, and here. And I hope you’ll check them out.
For now, suffice it to say that every now and then, we’ve got to be willing to jump into the back of that proverbial pickup truck and do the scary thing.
– Pick up the phone
– Have a cup of coffee
– Invite to a tour
– Visit them at home
We’ve got to do the risky work of not only asking “How can I keep this person happy.”
But also – “What’s the next best way I can direct this philanthropic relationship toward a gift that’s right for them and for us.”
Until you do that, your donors will likely think in small terms.
And that robs them of the opportunity to see their support do some truly amazing things.
And it robs you of the opportunity to see your mission advance to the next level of awesome.
So take a minute to challenge yourself – instead of spending all your time on the “safe” stuff – writing another newsletter, finishing another report, perfecting another spreadsheet – find those fun uncle challenges in your database.
You just might find that on the other side of your risk is the transformational donor your organization has been looking for.
In memory of Daniel Carter Woodard (1951-2025).
Photo by Olga Lioncat: https://www.pexels.com/photo/stallion-grazing-in-pasture-on-farmland-in-summer-7245251/
