Asking Up (The Wealth Gap Conundrum)

Update on JP's new book:

‍I’m excited to share the very first draft of my new fable, Gifted: A Fable About Fundraising (aka Awkward Invitations).

This is a special early peek reserved just for subscribers of The Breakthru Guide - and the friends you’d love to pass it along to.

If you’ve read Patrick Lencioni’s fables (The Five Dysfunctions of a Team, Getting Naked), you’ll recognize the style - short, story-driven, and practical. Gifted is about a 45-minute read (7,700 words). You’ll find both a PDF and audio files in this Google Doc link, so you can read or listen.

When you’re done, I’d love your honest feedback. You can:

• Email me directly (no need to hold back), or
• Fill out this quick 7-minute survey (anonymous feedback)

This book will be a free resource for charity leaders and major gift fundraisers. Your insights will help make it as compelling and useful as possible! I can’t wait for you to read it.

My friend Dan told me about a classmate he grew up with - same baseball team, same after-school jobs, same thrift store hoodies.

Then, in 2017, his friend struck it big in crypto.  Not just lucky - lucky-lucky.
Eight figures. A house with a recording studio. A BMW iX3 he drives “sometimes”. First class flights. Casual startup investments.

He’s sharp, with good instincts. He was living large, but giving wasn’t really on his radar.

Meanwhile, Dan had become a development director for a small education nonprofit.  The two of them still texted, still laughed, still remembered mowing lawns and eating $1 gas-station burritos.

But when a new campaign launched, my friend froze. “I should ask him,” he admitted. “But now it feels like I don’t belong in his world anymore.”

His boss, to put it gently, didn’t get it.

‍The Shift Beneath the Surface

‍One of the hardest dynamics in major gift work isn’t that wealthy people are intimidating - it’s that their wealth stirs hidden fears in us:

• Do I seem small or desperate?
• Will they still respect me?
• What if they think I’m just using them?
• Do I even believe I have something worth offering

These fears don’t come from the person who has wealth - they come from the story we tell ourselves when we feel small.

When someone’s net worth - especially a longtime friend - soars beyond what we can imagine, we start telling ourselves stories.  Stories that they now live in another universe. Stories that our invitation won’t land. Stories that maybe even our relationship can’t hold.

So the question becomes: when we approach someone whose financial capacity vastly exceeds our own, how do we ask with clarity and confidence - without shrinking, overcompensating, or getting a little weird?

‍Reframing Wealth - Without Shame or Hero Worship

‍Here’s what I have come to believe:

• You are not lesser because you earn less.
• They are not godlike because they have more.
• Your cause is not less urgent just because they live in luxury.

Wealthy people are still just people - people with fears, longings, egos, and hopes of their own. And when we see them clearly - not as walking wallets or untouchable titans - we find our footing again.

‍When the Relationship Precedes the Wealth

‍That’s what made my friend’s story so tricky. He wasn’t approaching a stranger. He was reaching out to someone who had known him - and whom he had known - long before the money.

And sometimes that makes it even harder. Because now you’re asking as an equal… who suddenly feels unequal.

Here’s what I told him:
‍You’re not asking from a lower place. You’re inviting from a deeper one - where trust and memory still matter. Wealth doesn’t erase that. If anything, it makes the foundation for giving even stronger.

So… How Do You Ask Someone Wealthier Than You?

‍Here are five reminders to ground you:

Money can distort things. It can inflate egos or stir insecurities. But when it’s held in love, purpose, and mutual respect, it can also build bridges.

Here’s my blessing when you’re asking someone wealthier than you:
‍May you walk in as a peer - not a petitioner.
May your voice stay steady, because your cause is clear.
May you remember your value doesn’t shrink when theirs grows.
And may your invitation stir something sacred… not just financial.

* * * * * * * * * *

‍If you haven't taken advantage of some of the resources I've created to help major gift fundraisers, take a look now!  Initial calls with me are free and "no strings attached".  Sometimes folks feel like they need to wait and not 'bother' me until they have a pressing issue.  No need for that...just make the call. 🕺

‍Here's where you can access a lot of content for free:

* Major Gift Fundraising MRI Scan - A story-based self-assessment that helps you name your instincts, clarify your posture, and grow with intention. Takes less than 20 minutes and gives you a custom coaching summary based on your responses.

* JappaFry Writer - A freely available AI tool that draws from over 175 pages of original teaching, storytelling, frameworks, and strategy from my 30 year career in major gift fundraising.

‍* Follow me on LinkedIn - You'll get short pro-tips and reflections on major gift fundraising every day between 5-7am pacific.

* Breakthru Newsletter - As you've seen here, these are longer weekly posts (audio and written) sent directly to your email.

* Breakthru Blog - the newsletter from the previous week gets posted here each week for everyone (so email subscribers get it a week early).

* Breakthru Podcast - Interviews with high net worth givers about how we as fundraisers can get better at inviting them to the party.  And audio readings of Breakthru Blog posts.

‍Before getting to the PAID stuff: My opinion is that no small ministry with a tight budget should be spending more than $3-5k (total) for major gift coaching/consulting.  Most of you will be good-to-go spending far less than that.  This was a major issue for me when I was a frontline fundraiser - major gift consultants were an expensive 'black-box-of-confusion' for me.  That stops now.

‍Here's the PAID stuff:

‍* Online Catalyst Course - This is a full brain dump of my 28+ years of experience - good, bad, ugly.  It's built around the fundamentals, the sacredness, and the fun, of major gift fundraising.  It's infused with Henri Nouwen reflections.  Many people can take this course and they will be 'cooking-with-gas' and not need any additional coaching from me on the core systems.  I'm grateful that this course has gotten *great* reviews.

* Live coaching with me - I refer to this as "brain rental".  The ROI on live coaching, as you might imagine, is extraordinary.

Finally, be sure to connect with my colleague Ivana Salloum.  She's super awesome and can help with scheduling and access to resources, etc.

I look forward to hearing about your good work!

Blessings,