🎵You've Got to Know When To Hold'em🎵

Whether it's with my good buddies at our annual retreat or a rowdy family game night with my kids, nephews, and nieces - I just love playing poker. Why? Because winning requires a combination of skill and luck. When the best poker player in the world is dealt a bad hand of cards, their chances of winning are slim to none. And while they have no control over the cards they’re dealt, how they play them will make or break their ability to stay in the game, and make it to the final winning hand.

I love major gift fundraising for similar reasons.  There are important disciplines to maintain, even though circumstances may occur outside of your control.  When that happens, you may just need to fold.  Good poker players will fold more than half the time and, depending on the game, up to 70+ percent of the time!  Novice players might see that as a sign of weakness.  “C’mon!”, they complain, “play poker!”.  Good fundraisers need to have the same discipline. If you’re feeling pressured by the peanut gallery, my advice is to “smile and wave”... remember that you’re still in the game, and while it’s super thrilling to win a big pot on the river*, it’s not a sustainable way to play, or win.

Kenny Rogers was aware of this. 🎵Know when to walk away…know when to run🎵… Having the discernment to understand when to wait, when to act, and when to gracefully let go of an opportunity until it’s ready is where skill and wisdom come into play.

Probably my most vulnerable moments in a poker game are when I’ve experienced a few lucky wins. “I’m on a roll now!”, I think. Then, two hands later, when I’ve lost all the chips I just happily gained, I remember that luck isn’t contagious. Not only does my neighbor's luck not rub off on me, neither does my own. In fundraising as well, external factors are not always reliable - the wealthy neighbor, the “perfect” economy, or that one great campaign someone else ran. Sometimes your best play is just to consistently show up, ready to work with what’s in front of you.

So, how do you play the hand you’re dealt?  Think about the last time you ‘swung for the fences’ in fundraising. Perhaps you made a bold ask, fully confident that the timing was perfect. Then, you realized it wasn’t. A failed ask can sting, and it can also remind us of an essential truth: success often lies in our preparation, rather than assumptions about how lucky we might be. It’s far more important to stay in the game.  Don’t gamble away your winnings only to be relegated to the sidelines.

Case in point:
Several years back I spent many hours preparing a large grant proposal for a foundation who really wanted me to be successful…but it just wasn’t coming together. Fortunately there was great strength in our relationship and, while they decided not to make the grant, they gave me the extraordinary opportunity to come back again with the same ask, adding some important tweaks to the approach (something only a handful of grantees were afforded in the 30 year history of the foundation). The tough news? It would be more than a year's wait before I could resubmit.  It was time to “hold’em” - so I did and, thankfully, we received funding on the next go ‘round.

Here are a few ways to refine your game:

1. Pay attention to the Strength of Relationship (SToR): Before you make an ask, evaluate your connection with the giver. Do you know their passions, milestones, and motivations? These insights are far more predictive of a successful ask than a hunch about their financial capacity.
2. Listen and learn: Some of the most impactful moments in my career have come from simply asking good questions and listening. What moves this person? What do they want to achieve? Givers often reveal their priorities if we slow down enough to hear them.
3. Be adaptable and humble: Sometimes you need to pivot and recalibrate. A “no” may not mean forever. But for now, you need to walk away.

While luck is not contagious, generosity is.

Luck does not spread like generosity. When one person sees the transformational impact of their gift, others notice. It’s not magic - it’s momentum. Generosity sparks when people feel part of something bigger - a shared mission that resonates deeply. Thus, your job is to help build momentum. Invite people into a story of transformation. Your skill lies in connecting their values with the vision you’re pursuing and the stories you have to share.

Being a disciplined poker player (aka, major gift fundraiser) means focusing on what you can control: your decisions, your reactions, and your readiness. It is a sacred challenge. We must stay focused on how we steward relationships and present opportunities.

Here’s to staying in the game and celebrating the amazing work of our causes!  Praying you all have a great week.

* It’s like when you almost lose, but a super lucky surprise at the last second makes you the winner.

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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:

‍* 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,