48. 5 Hilarious Fundraising Fails You Won’t Believe

48. 5 Hilarious Fundraising Fails You Won’t Believe

In this episode of the Fundraising Masterminds Podcast, we're taking a little break from heady development theories and practical fundraising guides to laugh you through 5 of Jim's most hilarious fundraising fails. You won't believe some of the things he's seen!

Join us as we look at Jim's worst fundraising experiences, from dinner horror stories to hilarious development disasters. Witness Jim's epic mishap at his very first major donor event as a 26 year-old newbie. Discover the worst thing you can do at any kind of event (hint: it involves flying glassware). Find out what happens when you send certified mail...in the middle of a blizzard. And learn how God can work all things according to the good of those who love him, even hilarious fundraising fails like these!

Whether you're a seasoned professional or are still scheduling banquets across the hall from rowdy male auctions, you should get a few good laughs from this episode! And remember to pay attention to the lessons you can learn from these nonprofit fundraising fails. These are some lessons you will never forget!

Don't forget to subscribe to our channel for more nonprofit tips and tricks!



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STOP FUNDRAISING. Get back to basics with....DEVELOPMENT BASICS

The Biblical Basis for Development for Nonprofit Leaders

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NEED HELP WITH YOUR NONPROFIT?

Most nonprofits are under-funded. Even if you think your nonprofit is doing well, we've found you could be doing much better. However, most nonprofits don't have a clear development strategy that keeps them grounded. As a result, they "get creative" and "try new things" based on what is popular or trending, or they get comfortable with where they are at and don't realize the dangers they will be facing in just a few short years.

The Perfect Vision Dinner Course is a 20-week "live video" course that addresses this problem head on. The course was developed by Jim Dempsey after 38+ years as a Senior Development Director at Cru. After Jim had personally done over 2,500 vision dinners in his lifetime and raised over $1 billion worldwide, Jim and Jason have partnered together to bring you Fundraising Masterminds. Our first course, The Perfect Vision Dinner is a time-tested proven formula that will introduce our development system and grow your nonprofit to its maximum potential.

The course includes 20-hours of personalized development coaching from Jim Dempsey and Jason Galicinski and also includes a real-time community group where you have access to everyone attending the course and also our Masterminds throughout the course.

The goal for this course is to fully equip you with a Biblical basis for Development so that you can Win, Keep and Lift new partners to higher levels of involvement with your nonprofit.

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Episode Keywords:

nonprofit leaders, fundraising, fully funded, podcast, horror stories, experiences, major donor event, development, mistakes, direct mail letter, response, complaints, Memphis, Tennessee, Anatole Hotel, male auction, make a wish foundation, challenges, flood, resilience, perseverance, sense of humor, perfect vision dinner strategy, fundraising fails, funny fundraising, nonprofit fundraising fails, fundraising fails you wont believe, fundraising fails you won't believe, 5 hilarious fundraising fails you won't believe, 5 hilarious fundraising fails you wont believe, nonprofit development, nonprofit development theories, practical fundraising guides, worst fundraising experiences, nonprofit horror stories, nonprofit development disasters, major donor, major donor event, nonprofit tips and tricks, Jim Dempsey.

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Episoder(131)

131. Friendraising Over Fundraising: How ISOW Bible College Went From $60K to $1.5M in 3 Years

131. Friendraising Over Fundraising: How ISOW Bible College Went From $60K to $1.5M in 3 Years

In this episode of the Fundraising Masterminds Podcast, we're talking about how ISOW Bible College went from $60K to $1.5M in 3 years.Join us as we break down the principles and paradigm shifts of fri...

16 Sep 36min

130. How to Transition Nonprofit Leadership — Without Losing Donors

130. How to Transition Nonprofit Leadership — Without Losing Donors

In this episode of the Fundraising Masterminds Podcast, we're talking about how to transition nonprofit leadership — without losing donors, damaging trust, or sacrificing relationships that took years...

2 Sep 31min

129. Exposing the Fundraising Industry: The Rules You Didn’t Write

129. Exposing the Fundraising Industry: The Rules You Didn’t Write

In this episode of the Fundraising Masterminds Podcast, we're exposing the "best practices" of the fundraising software industry — and why you're subconsciously following rules you didn't write.Join u...

19 Aug 29min

128. How to Overcome the Hidden Fear of Major Donor Rejection

128. How to Overcome the Hidden Fear of Major Donor Rejection

In this episode of the Fundraising Masterminds Podcast, we're talking about how to overcome the hidden fear of major donor rejection.Tune in to learn about the anxiety that no one names, but everyone ...

5 Aug 28min

127. Rethinking the Leadership Triangle: The Missing Link to Nonprofit Growth [Development 101]

127. Rethinking the Leadership Triangle: The Missing Link to Nonprofit Growth [Development 101]

In this episode of the Fundraising Masterminds Podcast, we're rethinking the Leadership Triangle: the missing link to nonprofit growth.Join us for another episode of our ongoing Development 101 series...

22 Jul 30min

126. Donor-Advised Funds: The Smartest Giving Strategy of 2026 (featuring Eric Fleshood)

126. Donor-Advised Funds: The Smartest Giving Strategy of 2026 (featuring Eric Fleshood)

In this episode of the Fundraising Masterminds Podcast, we're talking about donor-advised funds — the smartest giving strategy of 2026 — and why your nonprofit can no longer afford to ignore them.Join...

8 Jul 38min

125. How to Scale Major Donor Development Without Sacrificing Relationships [Development 101]

125. How to Scale Major Donor Development Without Sacrificing Relationships [Development 101]

In this episode of the Fundraising Masterminds Podcast, we're talking about how to scale major donor development without sacrificing relationships.Tune in to discover the #1 key to a successful develo...

24 Jun 30min

124. The 3 Most Dangerous Board Fundraising Myths

124. The 3 Most Dangerous Board Fundraising Myths

In this episode of the Fundraising Masterminds Podcast, we're uncovering the 3 most dangerous board fundraising myths and how believing them will destroy your nonprofit from the inside out.Join us as ...

10 Jun 36min

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