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What Princess Bride Fundraising Personality Are You?

“Fundraising is hard. Anyone who says differently is selling something.”

That’s one of my favorite paraphrased movie quotes from The Princess Bride. I’ve chuckled about it for years, and besides being an excellent way to kick off a book, it’s also the best way to set up a conversation about one of my favorite films.

First, it’s probably the PERFECT movie and if you don’t reference at least one thing from it a day, are you really living your best life?

Second, it beautifully encapsulates two philanthropy facts:

1. Raising money for nonprofits is not all sunshine and rainbow and unicorns and ice cream

2. The hottest trends and tech won’t help unless you have the basics down currently

If you haven’t seen the movie, that’s ok. Just stop what you are doing currently, tell your boss or board chair you’ll be unavailable for the next 98 minutes, and watch this classic from start to finish. Because the characters in it, will resonate with any do-gooder, and you’ll probably come to the conclusion that the entire movie can be used to map out your fundraising strategy.

If you have ever been at any HR event or training anywhere, you’re probably taken some sort of personality test to see if you are compatible with your coworkers so that you won’t eat Randy’s lunch from the fridge, or be reminded to use positive language towards Cindy to ensure she’s lifted up, even though she totally ruined that spreadsheet she was responsible for, and now you have to clean it up.

Ugh. Thinking about doing those makes be consider being thrown into the Pit of Despair rather than determine what numbered color I am.

However, we all have our quirks. And how do you recognize your fundraising strengths without a relatable and fanciful way of doubling down on what makes you a great nonprofit fundraising leader?

Well, let’s use a cast of characters from the single best movie of all time to achieve that and make your own fairy tale ending for your nonprofit.

So if your fundraising is “mostly dead” let’s take a dive into the types of development personalities you may have in your office (or you, yourself!) and use it to help you connect with donors, and supporters to fund your incredible missions!

The Princess Buttercup Fundraiser

The comely main protagonist of the story, Princess Buttercup deals with the stacked trauma of having her boyfriend kidnapped, a forced marriage to the king, her boyfriend coming back and then pretending not to be her boyfriend, and ultimately dealing with disappointment throughout the movie until the very end. Her therapist is gonna have one helluva field day with it.

And yet she keeps the faith about the good that is to come. Always.

This type of fundraising personality is a dreamer and can vision cast to others who are looking for inspiration during times of trouble. She is also quiet until pressed into standing her ground, and is an observer of the environment to make the proper point that “good is always a thing.” Donors will be attracted to this type of personality to overcome adversity and will be relatable as a co-hero in the supporter’s journey, as she helps them navigate a rocky path to give as generously as they can.

This type is as obsessed about fundraising as Buttercup was obsessed that her boyfriend would even defy death to rescue here. Sure, there are some moments of irrational positivity, but with cards stacked against an organization, this personality will be someone you can follow to cheerlead with stoic leadership in staying the course.

However, if there are Rodents of Unusual Size involved in a Fire Swamp, don’t think for a moment this personality will be useful.

The Dread Pirate Roberts Fundraiser

The multi-personality hero of the movie is a nearly ridiculously handsome young man who negotiated his way out of being executed by a pirate at sea. This type of personality is your story telling, swashbuckling, adventurous (and borderline too act-then-ask-forgiveness type of) human that is your enthusiastic cheerleader to get stuff done.

This individual is more aggressive in the verbal tactics to engage your donor base, but is very keenly aware of others likes and dislikes to adapt to any situation. A great planner, but needs assistance in helping to execute those big hairy audacious goals…even though he thinks he can burden the entire fundraising adventure on his own.

However, this personality is not just a one trick pony. Up his sleeves are surprises such as being able to relate to nearly anyone he meets with a quip, or a note, or even being ambidextrous when it comes to sword fighting.

Need an expert on drug abuse? This personality will know enough to be dangerous without having or needing a degree. Need someone to stand up to a donor who is a bully, even though his strength has been drained after an exhaustive special event the day before? This leader has your back.

Ultimately though, this type of personality is a giver. A giver of time. A giver of laughter. Or a giver of a smile to make you feel better…just as you wish.

The Inigo Montoya Fundraiser

If there was someone you’d want leading the charge at your organization, look no further than the secondary storyline hero, who is, if nothing else, the most focused goal oriented human you’ll ever meet. Sure, revenge isn’t really a great look or type of topic you should using to fundraise, but if you can find inspiration to avoid mission creep, Inigo Montoya is your guy to pay attention to.

This type of personality has a higher calling to do good (or bad, if you think that inflicting pain and death upon the man who struck down your father over an unpaid invoice) for your organization. They are inspired by more than just words on paper, but actions to showcase the impact of what you do.

Some might call it obsessive. Others will call it enthusiasm. Either way, this individual is gonna get the job done, even with a throwing knife lodged in his gut.

As a task manager, you won’t find a better personality. Lists of priorities, quick recaps of to-dos rather than wasting too much time giving summaries of what has already occurred are this person’s superpowers.

Also, they surprise and delight with one liners that no one expects – and that makes them enduring – and less frightening about his “whatever it takes to get it done” attitude.

The Fezzic Fundraiser

Need a bit of a calming, yet strong qualities for your leadership team? Look for the giant personality in the room, that has a that intimidating look or feel.

Every organization needs a Fezzic. A larger than life leader who can address big groups and get them to pay attention to “Moooooove” aside when there are roadblocks to getting things done. There is not a lot of depth to this personality type on the surface, which may make getting to know them and their other strengths to help you mission a little more challenging. Unless your mission is being able to throw boulders or fight a number of individuals for sport.

Your donors will look up to this individual, and perhaps even be inspired that someone can project the strength of an organization without the perception of trying too hard. They are authentic, stoic and filled with gratitude.

Also, they can protect you from Screaming Eels. Which, you never know you need, unless you find yourself in Eel infested waters on a pleasure cruise at night.

The Prince Humperdink Fundraiser

Ok, we all work – or have worked – with a Humperdink.

I apologize for even mentioning Humperdink, though we have no pre-stated agreement on using that term here on the blog. We DO however, need to walkthrough how to deal with these types of individuals.

This person is notorious, and probably even flaunts, the selfish relationships he has for personal gain. Besides plotting behind people’s back, this personality only has a few influential friends, but is probably attached at the hip to board members who he uses to prevent criticism and ultimately save himself from being removed from his position.

It’s never ok to have a team member who has ulterior motives than the mission. But whether they want more media time, don’t stick to the talking points, or go rogue and use their time to create things that are outside the scope of your fundraising plan (I mean, do you really want to feature a secret torture chamber in your annual report? No. No you don’t.) they need to be rooted and called out for not being on the same team.

This can involve some serious conversations, which you may need to bring your Dread Pirate Roberts personality type to be involved.

The moral of this story is that building your fundraising team is important. And though you might be a 7 Red/Yellow Connector, really you just need to be aligned with your mission, impact and path to get to your goals.

And though it might feel as if your nonprofit is slowly climbing up the Cliffs of Insanity, know that steady movement forward towards your fundraising goal is as simple well as consistent storytelling, continuous field activity, and being more clear than clever.

Put it all together and you’ll have a Hollywood Story ending that even a fever-ridden Fred Savage would applaud.




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