Where’s The Love? When Asking Feels Like Begging

The beard had been grown. The cause passionately communicated. The sponsors recruited.

It was time for the beard to come off so the funds could come in.

Taking a final tally, I found that some of the people who had agreed to be my sponsors had not yet made their donations. As I sat down to write a pledge reminder email, I realized that for me, this was the hard part. Suddenly, the passionate flow of my story hit a wall.

At the outset of this series I noted that the format of Dave’s fundraiser was perfect for him as a self-described introvert. Our Beards of Hope brought in beard growers to do the difficult job of “asking” for money, allowing Dave to focus on motivating his team, which found wild success. While this fundraiser’s structure helped him to get around that itchy curve a little more smoothly, there is no way to entirely escape this uncomfortable point of fundraising. No matter how smart the method, we will all at some point have to have that conversation. The “Ask.”

Except for a few social dynamos out there, getting down to the nitty gritty of collecting pledges is a common struggle. The asking process pinches like my childhood Easter Sunday clothes. I’ve never been described as a social dynamo, so I don’t know why I was so surprised when the “asking” conversation was such a difficult one to approach.

I want to explore how I dealt with this struggle, to offer you an approach to the asking process so that it feels less like begging and more like an extension of that first inspiring conversation.

The painful process of pledge reminders

The initial experience of sharing Dave’s story and my passion for the cause was an easy one because it was just that: sharing. When asked about my growing beard, I found sharing the grander story of adoption, what the Obwalds were doing, and how my growth would help bring their little girl home was as easy as going down a slide. But when the time came to “call in my chips,” the dynamic shifted. Suddenly I was sitting at the bottom of the slide wishing gravity would reverse so I could gleefully ride my way up. The glee did not come.

As I started an e-mail reminding a friend of their commitment to donate, all kinds of bizarre thoughts entered my head:

What if their original interest was just a ruse to get me to stop talking?

What if they’ve just hit hard financial times or been in a jet ski accident and can’t afford the donation they promised?

I didn’t even know they had jet skis, how could I not know that?

What if I forgot their birthday?

Did I forget their birthday?

Is that why they didn’t donate yet?

I am a horrible friend.

I felt like a Roman tax collector.

The e-mail felt like this:


What’s the matter with me?

Effective pledge fulfillment

I realized in that moment that I had recently heard someone warn against this exact scenario and I felt dumb when I realized that someone was me.

We’ve talked about how to share your nonprofit story for your fundraiser in a way that inspires rather than manipulates participation. In composing this follow-up email, I felt the only tactic I had left in my arsenal was to manipulate. So I knew I was missing… something.

I decided to go back over some of my previous posts in this series and see if another perspective would help.

Part 2: Inspire a movement: Why you should stop sharing what you do.” It may as well have been titled, “Hey Brandon, knock it off,” as I remembered Dave’s example of starting with the story; sharing why you care, rather than what you’re going to do.

Mentally, I had left the love – the story – out of the equation when preparing to “ask.” This left me feeling like an enforcer for the mob collecting a debt.

I had stepped out of the cause and into the mindset that I was asking for money for myself. As If I were asking for the cash, so I could buy an iPhone 6 or get my own jet ski. I had left behind the most important thing: that we were working to change a little girl’s life forever.

So as I tried to edit my e-mail, I began with the story, and kept repeating: You are not asking for you, you are asking for Aunna.

The key is to lift your story, the cause, up as high as possible at all times so you don’t lose sight of it when the task of the moment tempts you to look elsewhere.

Of every possible method, beginning the “ask” with your story accomplishes two things for you without ever having to manipulate a payment. It centers you and your donor around your cause, your passion and your ability to do something about it; and it guides your donor back into the role where they initially saw themselves able to contribute.

After all, their initial reaction to the story was to offer monetary support; they didn’t offer to grow a beard or adopt their own child — they offered to donate. That was their knee jerk reaction to the story and the role they saw for themselves in the solution. I didn’t need to convince them of anything. I didn’t need to view it as a sales pitch, or reducing a friendship to a transaction, but rather to begin with the story. Growing a beard is useless without a meaningful reason, and her name is Aunna.

The right image for the right feeling

Moving on to the theme of telling your story visually, I thought, “Aha, I have succeeded here. I already added a picture.” I was immediately pummeled by the realization that I had again failed my own test. I looked miserable. I hadn’t taken advantage of the fact that using a visual, like a photo of my beard, gave me an opportunity to be known. Or better yet, to let the fundraiser be known.

This donor hadn’t been growing a beard. I don’t think they kept up with the Our Beards of Hope blog or had any idea what the experience felt like. This image was a chance to share a feeling, but the only feeling my selected photo shared was that of being scolded by a Wookiee.

I added a new picture of my bearded self – yes, looking like Chewbacca – but taking pride in my homeless beard because it was able to do something profound.

Building a relationship with each donor

It had been a sad recipe: “Dear sir and/or madam, all I did was grow a beard. And now YOU have to give money. And all I did was get lazy about shaving for a while.” The guilt sets in… right?

I giggled like a little schoolgirl as I saw how these two shifts in my approach, focusing on the story and using visuals to share a feeling, had taken the focus entirely off me. Next was the idea I had shared in “ Part 4: How to grow a following.” I read through the ideas of how to treat a distant benefactor like a friend, focusing on the donor relationship. I saw that I needed to change my message from “me, me, me” into something worth saying, making sure that I didn’t treat my real life friend like they were a distant benefactor.

In that moment when I used the phrase “distant benefactor,” I realized what my greatest disconnect had been. What made it so hard to ask for money was that I had viewed the fundraising process as disconnected parts, rather than as a whole.

When I began spreading the word about Our Beards of Hope, I saw those first conversations with potential donors as an appeal to their heart by enrolling them in a cause as a sponsor. However, this e-mail felt only like an appeal to their wallet to fulfill their pledge. In my insecurity over dealing with money in general I left out our shared purpose. This not only made it harder for me to ask, but also completely negated their passion and value for the cause. A passion they had decided to express through monetary support.

The essential roles for a successful fundraiser

When I checked in with “ Post 5: How to grow your leaders,” I put it together. I remembered how Dave communicated with his fundraising leaders in way that gave them (us) a shared stake in the cause. He focused on the value of something as simple, or gross, as my gnarly beard. To be clear, there is no real value in looking like the guy who was kicked out of ZZ Top, unless that sad beard serves to point others to a greater cause. I didn’t need to look at it as asking for a cash payout. Success for me came from looking at their monetary support the way my leaders emphasized my support, to point to the cause in which we shared ownership.

The importance is not focusing on what we can do, but rather that we can do something. The size or worth of the role we play has nothing to do with the simple fact that we are a part of a whole.

A cause dies without its leaders. A leader without followers is just a dude wandering around. Donors without a love to guide and inspire them are just losing money.

The key feature in every role is a clear view of the North Star.

I took another stab at my e-mail.


Asking can be hard. It may tempt us to soften the blow by asking less or making less of our cause, but that method is its own sour reward. People are weary of being asked to do the least possible. People are hungry to see the full weight of their own potential on behalf of the causes that they love. But they have to be asked.

Fundraising for a purpose

It’s been five months of awkward growth. I have seen friends turn into werewolves and made new friends that look delightfully like aspiring Santas. But when I look back I don’t remember the hot summer days, the itchy nights or the fact that several friends waited for the beard to come off before they would trust me with secrets. Oddly what I remember most is looking forward; with a leader that focused us around a clear and impassioned cause we had no choice but to do the same.

The result: In a fundraising format that was initially designed to bring in $2,500 the Obwalds have raised every cent of the remaining $15,000 they needed to complete the entire adoption process.

The Obwald family (their three children included) has just returned home from China with Aunna in their arms.

The beards have come off so that a little girl could come home.

Sometimes to reach something beautiful you have to go through some gnarly growth.

Joshua is bit of a Swiss army knife around Aplos. More like one of those generic, off-brand multitools that really only has two or three tools that are actually of use, but darn if they're not the best at what they do. So when he's not writing code for the company website or giving a copyedit to the eblasts, he's home working on his novel, spending time with his wife and daughters, or out cycling up by the Millerton Lake. (What's that? My bio isn't long enough? Ok, I got this...) He also likes cheese, prefers Pixel to iPhone, hates click-bate article titles, is a strong believer in the Oxford Comma, thinks Rouge One was better than The Force Awakens, and The Last Jedi was better than both. (Boom, nailed it.)

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