Rainmaker Fundraising

Every nonprofit has a list of local corporations that should be giving. Jeff Serrano has spent 34 years in the corporate lane of fundraising, and he’d like you to delete that word from your vocabulary.

Jeff is the founder and president of 360 Corporate Engagement Consulting. Before that, he led corporate engagement for the American Cancer Society, the American Heart Association, the Dallas Museum of Art, UT Arlington, and UNT Dallas. Before that, he worked at AT&T and was a reporter for the Houston Post. He’s sat on both sides of the table, and he knows exactly how your pitch sounds from the other side.

In this episode, Andrew and Jeff take apart the myths that keep nonprofits from landing meaningful corporate partnerships. They cover the “deep pockets” fallacy, why your gala committee might be sabotaging your annual corporate giving success, and the matching-gift money most organizations never claim. Jeff also tells the story of how 30+ employee resource groups at AT&T turned a regional cancer-screening push into a national corporate movement.

The Conversation

Act One: The Myth of the Bottomless Checkbook

Jeff opens with the misconception that has wrecked many corporate pitches (03:02): big company, big headcount, so surely big money for your cause. In reality, most corporate giving offices run on tight budgets and skeleton crews, often one or two people, rarely more than three (27:10).

And the person you’re talking to is almost never the one who decides. Decisions usually come from committees that can include anyone from an admin assistant to the CFO (05:14). Jeff saw how that cuts both ways during his 12 years at the Dallas Museum of Art. A company that didn’t prioritize the arts would still come through because one committee member loved them.

Act Two: The Back Door Is Usually Open

If one relationship is a single point of failure, Jeff’s answer is to build a dozen (07:50). Marketing, Community Relations, PR, and especially Government Relations (”they don’t give money, but they have contacts”) that all become ways in.

His best proof comes from his time at AT&T (09:16). Tasked by the American Cancer Society with rallying corporate support for a national colorectal screening campaign, Jeff skipped the front office and went to the employees. He spent eight months working with more than 30 employee resource groups. Along the way he found a champion: an employee whose own screening caught her cancer. The result was a nationwide internal broadcast. Once AT&T was on board, other companies followed.

Act Three: How Nonprofits Sabotage Themselves

Nobody wants just a logo on a banner, Jeff says (12:33). In 30+ years, he never met a company that did. Companies want impact, alignment with their business, and sometimes a way to repair a bruised local reputation.

Then Andrew confesses a sin from his children’s hospital days (15:21). Grants, major gifts, events, and Children’s Miracle Network staff would sometimes approach the same company, separately, for different things. Jeff’s fix was elegantly simple: every gala ask letter included one sentence protecting the company’s annual corporate gift.

Then there’s the word Jeff has banned outright (23:17). Bosses used to grumble that companies “should” be giving. Jeff, who came from the corporate world, knew that word would kill the meeting before it started.

Act Four: Where the Money Is Hiding

Jeff doesn’t expect corporate cash to surge in this economy (18:47). But he sees plenty of opportunity around it. One is in-kind gifts that cover real budget line items. “I’m not talking about pencils and paper clips.” Another is pro bono help from corporate marketing, HR, and accounting teams. The third is matching gifts, which may be the easiest money most nonprofits never collect (21:38).

He closes with lessons from a 34-year career that started, by his telling, at age ten (01:00). (Andrew claims twelve. Neither should be trusted with math.) Deliver what you promise, and give corporate partnerships a dedicated owner (25:07). And do one thing in the next 30 days while budgets are being set: say thank you (26:28). “There’s never too many thank-yous.”

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The Big Ideas

Lead with their problem, not your need. Research a company’s business objectives and pain points before you ask, and show how your mission helps them get there.

Think in networks, not contacts. ERGs, marketing, PR, and government relations are all entry points. A single relationship is a single point of failure.

Coordinate internally before you go external. One company, one point person, and one integrated strategy. Corporate partners notice when you’ve done your homework, and they notice when you haven’t.

Check your matching-gift pipeline. It may be the easiest revenue your organization isn’t collecting.

Connect with Jeff

Website: https://www.360corporateengagement.com

Email: ejserrano@360corporateengagement.com

Check out 360 Corporate Engagement Consulting’s key service offerings.

Rainmaking: The Fundraiser’s Guide to High-Impact Offers

Your fundraising offer, or the reason you give donors to support you, must answer seven key questions to effectively motivate a gift. Most nonprofits get this wrong. In fact, many simply fall back on the most generic offer possible, “you can help provide hope.”

But generic hope doesn’t get the job done.

And if your mission is critical, you need offers that motivate donors to act and to make the most generous contributions possible.

That’s why I wrote Rainmaking: The Fundraiser’s Guide to High-Impact Offers.

This book distills the offer development training that I’ve guided hundreds of nonprofits through over the last 25 years and helps you successfully answer the Seven Questions for your organization.

The book is priced specifically for you, the nonprofit fundraiser or leader who needs to get things done effectively, without breaking the bank. Print copies are available for $9.99, and the Kindle version is only $4.99.

If you buy the book, shoot me an email and I’ll send you a FREE Toolkit to help you act on everything in the book. It’s a $24.99 value that you get completely free!

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Most organizations treat a capital campaign like a marathon. Holly Kessler’s team treated theirs like a sprint, and they’re about to cross the finish line on a $1.1 million goal with a staff you could fit in a minivan.

Holly is the Director of Community Engagement at Forsyth Jail and Prison Ministries in Winston-Salem, North Carolina. The ministry has served the county jail and a state work-release prison camp since 1977, through chaplaincy, a pre-release Transition to Work program, and post-release support. Holly is an ordained pastor who spent more than a decade in child welfare fundraising before joining the ministry in early 2024. She didn’t go looking for prison ministry. It found her.

In this episode, Andrew and Holly unpack how a five-person full-time team bought a building, renovated it, and opened a reentry center in under a year. They also kept the annual fund on track the whole time. Holly shares the low-budget marketing that worked, the open house they threw for a building they didn’t own yet, and the one-word lesson that changed how they ask for major gifts: specific.

The Conversation

Act One: “I Can Raise Money for That”

When Holly interviewed for the job, she asked her future executive director a dangerous question (04:39): after nearly 47 years of steady work, what’s next? His answer was a dream to build a reentry center with transitional housing, meeting space, and a stronger post-release program. Holly’s reaction was immediate. “I can raise money for that.” Her logic was hard to argue with. These men are coming home one way or the other. The only question is whether they come home with support.

The board said yes in 2025, and things moved fast (06:37). The silent phase started that summer. The campaign went public at the ministry’s October breakfast, and the building was purchased the same month. They raised more than $600,000 by year-end. Renovations ran from December to April, and the First Lady of North Carolina, Anna Stein, spoke at the May ribbon cutting. A week later, the first two residents moved in. As of recording, they’re $28,000 from the goal.

Act Two: Two Asks, One Breakfast

Holly’s biggest surprise was the speed (07:57). The campaign budget was about one and a half times the ministry’s annual budget, and the team still hit its annual fund goal in both years. The less pleasant surprise: a few donors who were expected to step up didn’t. Andrew can relate (08:57). In one of his own campaigns, a board member proudly pulled out a credit card and gave $50. Sometimes that’s just how it goes.

So how do you ask for capital and annual dollars without one eating the other (09:43)? Their consultant was blunt. Everyone already knew about the project, so not mentioning it at the breakfast would be weird. Some people would shift their annual gift, and the team would have to live with that. The fix was clarity. They used separate pledge cards, presented the campaign first and the annual fund second, and the executive director closed by saying, in effect, “We need your annual gifts too.” Lots of people gave to both.

Act Three: The Good-Enough Playbook

Holly’s first keeper is a little heretical (11:35). They wrote a strong case statement and professionally printed one page. Everything else, including the videos, was made in-house. A slick video gets watched once, she says, so “good enough” really is good enough.

The second keeper came from their realtor (12:40). He convinced the seller to let the ministry host an open house before closing. Big artist renderings showed visitors what the empty rooms would become, and the footage later helped breakfast guests who missed it see the same vision. The third: they applied for every capital grant they could find (13:25). They won more than half, several from brand-new funders. That matters in a city like Winston-Salem, where everyone knows who has deep pockets and everyone is already knocking on their doors (14:07).

And what would they never do again (15:02)? Holly thought hard and came up with exactly one thing: the open house caterer. Way too much food, way too much money. They switched caterers for the ribbon cutting. Lesson learned.

Act Four: Name the Number

The board went first and gave more than 10% of the goal together, with every member participating (17:39). That gave the team a strong number to announce on launch day. From there, they used donor history and CRM screening to find prospects for five- and six-figure gifts, then met each one for a tour and a conversation (18:35).

Here’s the lesson Holly wants every fundraiser to hear (18:59). When they made a specific ask, donors almost always met it. When they asked vaguely, they heard “We’ll think about it, we’ll pray about it.” Then they never heard anything again. People with that kind of capacity are used to being asked for specific amounts. Don’t be shy.

She closes with the story that sums it all up (20:14). A board member brought her neighbors to the open house. Their son had been incarcerated on drug-related charges and later died from his addiction. “If our son had had this type of resource when he got out of prison, he might still be here today,” they told Holly. A space in the center now carries his name. At the ribbon cutting, his mother stood in front of the sign with tears streaming down her face.

The Big Ideas

Don’t let fear of cannibalization stop you. Ask for both capital and annual gifts, and make the difference crystal clear with separate pledge cards and an explicit “we need both.” A few donors will shift their gift. Most won’t.

Good enough is good enough. One strong case statement and one polished piece go a long way. Your donors care about the vision more than the production value.

Let people walk through the dream. An open house with renderings, even before you own the building, turns an abstract plan into something donors can see and feel.

Look past the usual deep pockets. Apply for every capital grant you can find. Institutional funders you’ve never approached may be the ones who say yes.

Name the number. Specific asks get met. Vague asks get prayed about and forgotten.

Quotable

“These men are coming back into our community one way or the other. So they can come back with our support or not.”

“A real slick professional video is really pretty to look at. They’re gonna look at it once and they’re gonna move on.”

“People who have that kind of means are used to very specific asks.”

“If our son had had this type of resource when he got out of prison, he might still be here today.”

Connect with Holly

Website: https://fjpm.org

Holly’s contact information is on the ministry’s leadership page, along with details on its chaplaincy, Transition to Work, and post-release programs.

Rainmaking: The Fundraiser’s Guide to High-Impact Offers

Your fundraising offer, or the reason you give donors to support you, must answer seven key questions to effectively motivate a gift. Most nonprofits get this wrong. In fact, many simply fall back on the most generic offer possible, “you can help provide hope.”

But generic hope doesn’t get the job done.

And if your mission is critical, you need offers that motivate donors to act and to make the most generous contributions possible.

That’s why I wrote Rainmaking: The Fundraiser’s Guide to High-Impact Offers.

This book distills the offer development training that I’ve guided hundreds of nonprofits through over the last 25 years and helps you successfully answer the Seven Questions for your organization.

The book is priced specifically for you, the nonprofit fundraiser or leader who needs to get things done effectively, without breaking the bank. Print copies are available for $9.99, and the Kindle version is only $4.99.

If you buy the book, shoot me an email and I’ll send you a FREE Toolkit to help you act on everything in the book. It’s a $24.99 value that you get completely free!

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Every fundraiser I know obsess over the ask. My buddy Ted Draper obsesses over everything that comes before the ask, and that’s how his team helped take Biblica’s major gifts revenue from about $12 million to more than $30 million.

Ted is the Vice President of Strategic Engagements at Biblica, the ministry that stewards the New International Version (NIV) of the Bible and works with roughly 150 partners in 120 countries to put Scripture in people’s first language. He’s been fundraising for almost 15 years, after a start in corporate sales and marketing (including a stint in ad sales). Like most of us, he fell into the work. He resisted it at first. Now he can’t imagine doing anything else.

In this episode, Andrew and Ted dig into how Biblica turned donors into champions who bring their friends to the table. Ted explains why he thinks of every ask as something you earn, and why a fishing boat makes a great venue for donor cultivation. He also shares the African vision trip that led to $3 million in new giving, and the three-word hiring formula he swears by: humble, hungry, and a hustler.

The Conversation

Act One: From Donors to Champions

Andrew opens with the big number (01:17): how does a major gifts program go from $12 million to over $30 million? Ted says there was no single magic moment (02:05). Biblica had a leader with a real heart for major donors. It partnered with a firm that brought in new donors. And it treated the whole thing less like hunting and more like farming. Plant, tend, wait.

The real accelerant was a simple question to existing investors (02:32): if you wanted to invite your friends into this journey, what would that look like? Donors started lending Biblica their relational credibility, not just their money. That’s when growth went exponential. Andrew asks how you build enough trust for that (03:32). Ted’s answer is radical transparency about where the money goes, plus a high level of engagement. He’s also noticed a shift over the last three to five years. Donors want to give in community, alongside people they actually enjoy (04:04).

So what does that look like in practice (05:03)? A thirtysomething entrepreneur asked Ted how his small group could get involved. Ted gave the great fundraiser answer: “What would that look like for you?” The group designed it themselves. A fundraiser visits, presents a couple of projects, the group prays and decides, then comes back with an answer (05:32). Biblica also hosts coffees and desserts. And Ted once took a group of guys fishing, where cell phones don’t work and nobody can leave for hours (06:27).

Act Two: Earning the Right to Ask

Andrew’s rule is blunt: if you don’t have the follow-up plan built, don’t do the event (07:35). Ted agrees. After every gathering there’s a thank-you email, a phone call, and, when possible, a sit-down to hear how the person is responding (08:02). Then the plan adapts. “Some of them need more information. Some of them need inspiration and some of them need an invitation.”

That’s the heart of Ted’s approach (09:11). The ask is important, but it’s a small part. First you prove credibility, accountability, and that the work actually works. “Essentially we’re earning the right even for the first ask, much less the second one.” How does he know he’s earned it (09:56)? He asks permission: would you be open to a strategic funding request? Don’t expect A plus B to equal C, he warns. He has four kids raised in the same house, and they all hear and respond differently. Donors are the same.

Andrew pushes on the obvious tension (10:51). What about the CFO asking when the money’s coming in? Ted says you guide the donor’s journey while respecting their timing (11:19). If you’re asking good questions and staying involved, the two usually line up within 30 to 60 days. And yes, he tracks it all in an old-school Excel spreadsheet.

Act Three: Shoulder to Shoulder

What’s changing in Christian ministry fundraising (12:09)? Ted sees three shifts. First, donors want outcomes and solutions, not just activity (12:30). He draws a sharp line here. An impact report shows what the organization did. A stewardship report shows what the donor did. Second, high-capacity donors are focused on multigenerational giving and passing generosity to their kids and grandkids (13:26). Third, the gap between a first gift and a second large gift is getting longer (13:57). There are a lot of options out there, and like restaurants, everyone can point to a bad experience.

Which brings us to vision trips. Ted takes investors overseas about once a quarter (14:46), from South America to the Middle East, Africa, and Asia. Standing shoulder to shoulder with church planters and Bible distributors moves investors into champions, and it answers every “Is this really working?” question at once (15:25).

Then the story (16:53). Ted took one donor to Africa to meet a church planter working in a Muslim-majority nation. After the trip, the donor hosted a simple dinner for his friends. Over the following two years, that one trip produced about $3 million in giving, because he opened his Rolodex. Ted is candid that every vision trip has something go wrong (18:12). Unstable governments and deep poverty are why they’re there. And they’re not there to dig ditches or paint walls. They’re there to see the work, pray for the people doing it, and receive more than they give.

Act Four: Hustle Isn’t Hurry

Asked about building strong fundraising teams, Ted opens with a confession (19:13): “I’m a horrible hiring manager.” He sees potential in everyone. His formula riffs on Patrick Lencioni’s “humble, hungry, and smart” (21:13). Ted’s version is humble, hungry, and a hustler. Humble, because you’ll never know as much as the head of translation or the regional leader (19:43). Hungry, because you have to learn the investor and the organization. And hustle, because there’s only so much you can learn from donor profiles. Andrew can relate (21:40). He fumbled his first face-to-face solicitation by paying more attention to the wealth screening than the conversation.

Andrew wants to make sure “hustle” isn’t mistaken for rushing to the ask (22:30). It’s not, says Ted (22:55). It’s patiently pursuing the relationship to find where the alignment is. His cadence is an email, a call, a postcard, another call, another email (25:01). Then sometimes he’ll “bless and release.” The file stays open, the Christmas card still goes out, and he’ll grab coffee when he’s in town. One donor ignored him for a year, came to dinner, went quiet again, and gave three years later (25:30). When a staffer complained that a donor never emailed back, Ted’s reply was simple: “So it’s his responsibility?” (28:22).

Andrew adds his favorite persistence story (28:50). A man finally picked up and said, “I’ve got 13 calls from you in my call log. Nobody ever calls 13 times. OK, I’ll give you 10 minutes.” Ted’s advice: when you get the 10 minutes, make them count (29:49).

The lightning round wraps it up. The belief Ted had to unlearn (30:23) was that it was all on him. “I’m not smart enough, I’m not strong enough, and I’m not clever enough to make anybody do anything they don’t want to do.” Ad sales taught him to present three options. Fundraising taught him to ask permission instead (31:23). His advice for new fundraisers is to stay put (32:10). Longevity deepens relationships, and “nobody ever gets fired because they raised too much money.” And for the C-suite (34:29): give the next generation room to redefine the job. Fundraisers are a long-term investment, and “everything runs at the speed of relationships.”

The Big Ideas

Turn donors into champions. Ask your investors what it would look like to bring their friends along, then let them design it. Their relational credibility is worth as much as their gift.

Don’t plan the event until you’ve planned the follow-up. Thank-you, phone call, sit-down. Then adapt to what each person needs: information, inspiration, or an invitation.

Earn the right to ask. Prove credibility and impact first, then ask permission to make a request. The ask is the smallest part of the process.

Show, don’t tell. A few days standing next to the people doing the work builds more trust than a year of reports, and champions who’ve seen it will open their Rolodex.

Hustle isn’t hurry. Pursue the relationship patiently and persistently. If a donor doesn’t call back, that’s not their responsibility. It’s yours.

Stay put. Longevity deepens relationships, and nobody gets fired for raising too much money.

Quotable

“Some of them need more information. Some of them need inspiration and some of them need an invitation.”

“Essentially we’re earning the right even for the first ask, much less the second one.”

“I’m not smart enough. I’m not strong enough. And I’m not clever enough to make anybody do anything they don’t want to do.”

“It’s your responsibility to patiently and politely pursue the relationship.”

“Everything runs at the speed of relationships.”

Connect with Ted

LinkedIn: Here

Website: https://www.biblica.com

Learn more about Biblica’s Bible translation, publishing, and engagement work with partners around the world.

Rainmaking: The Fundraiser’s Guide to High-Impact Offers

Your fundraising offer, or the reason you give donors to support you, must answer seven key questions to effectively motivate a gift. Most nonprofits get this wrong. In fact, many simply fall back on the most generic offer possible, “you can help provide hope.”

But generic hope doesn’t get the job done.

And if your mission is critical, you need offers that motivate donors to act and to make the most generous contributions possible.

That’s why I wrote Rainmaking: The Fundraiser’s Guide to High-Impact Offers.

This book distills the offer development training that I’ve guided hundreds of nonprofits through over the last 25 years and helps you successfully answer the Seven Questions for your organization.

The book is priced specifically for you, the nonprofit fundraiser or leader who needs to get things done effectively, without breaking the bank. Print copies are available for $9.99, and the Kindle version is only $4.99.

If you buy the book, shoot me an email and I’ll send you a FREE Toolkit to help you act on everything in the book. It’s a $24.99 value that you get completely free!

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Dr. Clark Dickerson has led more than 250 capital campaigns over 40 years. Every one of them has rested on the same three principles:

* God is the owner of all

* We’re stewards and not owners

* We’re blessed to bless others

In this episode, Andrewsits down with Clark Dickerson, the co-founder of DickersonBakker to talk about his new book, Growing into Generosity: God’s Call to Greater Financial Faithfulness. Clark starts at the beginning. His first campaign was a $2 million effort for a Tennessee Christian school in 1985. Then comes a 100th-anniversary campaign at Johnson Bible College. Afterward, the college president pulled him aside and said the only thing wrong with this kind of fundraising was that they hadn’t started 20 years earlier. Clark also shares how he won his first college campaign. When a president asked how many successful college campaigns he’d led, Clark answered, “When we finish yours, it will be one.”

From there, the conversation goes after the hard stuff:

* Why pastors, executive directors and board members avoid talking about money, and what that silence costs their organizations.

* Why up to 40% of Christians give nothing at all.

* Why a couple earning $600,000 a year could say “there just wasn’t anything left” at the end of the month.

* Clark’s argument that the hardest stewardship principle is prayer. He believes many people don’t pray about their giving because they’re afraid of what the answer might be.

Clark also explains why these ideas apply well beyond ministry. His long-time line is that “donors do the good deeds,” and the organization is simply the conduit. His advice to fundraisers is to raise money for the need, not the building.

The episode closes with one of the best donor stories you’ll hear. A board chairman angrily refused a $50,000 ask: “Who in the world do you think you are?” Then he showed up at Clark’s airport hotel at 11 p.m., soaked from a thunderstorm, to say yes. The two talked until 3 a.m., and that conversation changed how the family gave from then on.

In this episode:

* (00:47) Clark’s first capital campaign, in 1985

* (03:34) The campaign that convinced Clark this was his calling

* (07:26) Who Growing into Generosity was written for, and the three principles behind every campaign

* (13:28) What happens to an organization when its leader won’t talk about money

* (18:18) Do these principles work in secular fundraising? Why “donors do the good deeds”

* (20:18) The hardest principle for people to accept: praying about giving

* (23:19) Giving first versus giving last

* (25:38) The midnight knock: stories of generosity that changed lives

* (29:50) When people don’t know, and when they know but aren’t willing

Get the book: Growing into Generosity: God’s Call to Greater Financial Faithfulness by Dr. Clark Dickerson.

This episode of the Rainmaker Fundraising Podcast is sponsored by my newest book, Rainmaking: The Fundraiser’s Guide to High-Impact Offers. This 49-page book (yeah, it really is that short — on purpose) is packed with the specific guidance and insights you need to improve your nonprofit’s fundraising offers and raise more money. It includes the exact framework I have used to guide hundreds of organizations through the offer development process over the last 25 years. And you can read it faster than you can read a Trader Joe’s newsletter.

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

This might be the most important information you hear today for your nonprofit’s growth.

The majority of wealth in the U.S. is held outside of cash, in other assets like stock, 401k’s, IRA’s, real estate, and closely held business interests.

But nearly every nonprofit I’ve encountered (and at this point, that’s thousands) are focused on asking donors to write them a check or give by credit card. Essentially going after that remaining 3%.

Why?

Nonprofits that are actively seeking asset-based gifts are generating huge returns compared to those that aren’t.

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Justin Wheeler, Founder/CEO of Funraise and I talking about the realities of activating major giving behavior through high-touch direct mail outreach.

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Every fundraiser on the planet has, at some point, wished they could have a prep conversation with a donor before they actually sit in front of them to make an ask of any kind. But that’s silly. That’s not possible. Instead, most of us settled for half-baked role playing with a colleague from time-to-time. And that was helpful. Sort of. But it was never exactly what we needed. It was never dialed in as much as many of us wanted. The result? Many of us still walked into donor visits and meetings nervous, unsure of ourselves, and unprepared to navigate […]

Chapters

• (00:00:00) - Rainmaker Fundraising: Guest Interview
• (00:01:17) - Practical Learning for Fundraisers
• (00:03:31) - Facebook's First Paying Customers
• (00:03:50) - Why I Launched a Tech Company
• (00:08:10) - How the Fear-Based Fundraising System is Changing the Way
• (00:11:10) - Baker Fundraising: From Friendly to Fundraising
• (00:15:46) - The New Way to Coaching
• (00:18:28) - How To Raise Money With a Board of Directors
• (00:19:38) - Beyond the Money Flow
• (00:24:21) - Fundraising Goals and Motivation
• (00:26:15) - The New Goal-oriented Meeting
• (00:28:28) - "A Touch of Mercy"
• (00:29:17) - Give Like a Corporate Coach
• (00:31:08) - Coaching of the Leader
• (00:33:54) - Practivated: How to Navigate the Challenging Personality of
• (00:38:38) - A Few More Favors For You

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

“How are you?” Simple question, right? If you lead a nonprofit organization, a ministry, or work inside one, this probably feels like a loaded question. A trap, if you will. What we all know, but what so few are willing to admit, is that burnout is at an all-time high in our sector. As Nathan LaGrange, Executive Director at Oasis Rest International says, leaders don’t set out in their careers to flame out. No one wants to burn out, to harm their most precious relationships, or end up on the brink personal and professional failure. But it happens. https://youtube.com/shorts/ksKb5a8B_GI?feature=share In […]

Chapters

• (00:00:00) - Rainmaker Fundraising Podcast: Rest and Recover
• (00:01:19) - Andrew McMillan on Planting His Soul
• (00:07:38) - Oasis Rest: A Place for Leaders to Talk
• (00:09:06) - Burnout in the Church
• (00:13:47) - The importance of caring for the leader
• (00:19:34) - A Sacred Controversy About Service Profit Chain
• (00:25:26) - How to Reset the Relationship Between CEO and Donor Development
• (00:29:13) - How Do You Retreat Away From Responsibilities?
• (00:32:57) - How to Encourage Your Pastor
• (00:35:54) - The Retreat Safety
• (00:38:04) - Life, Love, Liberty and Legacy
• (00:41:47) - Oasis of Rest
• (00:45:50) - How to Slow Down in Leadership
• (00:50:34) - Oasis REST: Slow Down
• (00:51:23) - How to Reach Out to Nonprofit Leaders
• (00:52:32) - The Rainmaker Fundraising Podcast

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

With access to clean water remaining a pressing issue in our world, charity: water stands out as a beacon of innovation and change. Brady Josephson, VP of Marketing and Growth (and a semi-regular guest on The Rainmaker show), shares insights into how the organization is transforming the way it engages with the world, driven by a relentless mission to provide clean water to every person on the planet. In our conversation, Brady the power of curiosity, a trait that fuels his (and the entire team’s) approach to innovation at charity: water. Working alongside the organization’s founder Scott Harrison, who embodies […]

Chapters

• (00:00:00) - Rainmaker Fundraising Podcast
• (00:01:01) - Meet Charity Water's Chief Marketing Officer
• (00:02:50) - Dave Raley on His 'Superpower'
• (00:03:43) - Charity Water Executive Director on Innovation
• (00:07:37) - What's the Balance Between Innovation and Change at Charity Water?
• (00:12:18) - The Nonprofit Organization's Attention Challenge
• (00:15:18) - Creating a Charity Experience Lab in Franklin
• (00:18:11) - The World Without Water Experience
• (00:24:08) - Small Nonprofits: The Next Step in Innovation
• (00:29:57) - How to get in touch with Charity Water
• (00:30:36) - The Biggest Mistakes Nonprofits Make
• (00:31:04) - A Request for the Rainmaker Podcast

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Should you invest in branding, OR, should you invest in fundraising? What creates greater impact for your cause? The answer often depends on who you ask. There are plenty of fundraising consultants who will tell you that investing in brand is a useless exercise, and all you need to do to be successful is invest in fundraising. Buy more direct mail. Spend more on paid ad programs. Hire more consultants. Do more events. If you’re not careful, you’ll invest in a grab bag of tactics that may not move the needle for you on revenue. Sadly, too many nonprofits do […]

Chapters

• (00:00:00) - Kevin Brown on Fundable & Findable
• (00:00:45) - How to Build a Brand for Nonprofits
• (00:02:00) - Writing Down the Book
• (00:02:33) - Getting Out There: The LinkedIn Content
• (00:03:44) - Mission Clarity and How to Raise Money
• (00:06:30) - What is Vision for Nonprofit Leaders?
• (00:08:38) - The Secret to Success in Raising Money
• (00:11:03) - Brand Investment in Community
• (00:11:43) - Brand Investment: An Investment
• (00:13:17) - What Role Do Boards Have in the
• (00:15:01) - Strategic Plan: Everything Is Possible, But Everything Isn't
• (00:17:15) - The Investment Strategy of Building a Brand
• (00:18:17) - Nonprofit Communications and Brand Teams Understaffed
• (00:20:05) - How to Build a Nonprofit Brand with Just One Word
• (00:23:37) - A Few Favors for the Rainmaker

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Do you know the 7 key donor performance metrics that drive organizational fundraising success in your nonprofit? My friends Gabe Cooper and Carly Berna from Virtuous help us dig into those KPI trends in this conversation about the Virtuous 2025 Nonprofit Benchmarking Report. Some of the insights we cover in this conversation include: The importance of donor retention, and the key difference between overall retention and net donor retention Challenges facing the nonprofit sector, and how doubling down on relationship, personalization, and automation can help offset some of those challenges Why you have to start leveraging data and automation (including […]

Chapters

• (00:00:00) - The Rainmaker Fundraising Podcast
• (00:01:21) - Virtuous's 2025 Nonprofit Benchmarking Report
• (00:02:17) - The 7 KPIs that Matter The Most to Driving Revenue Growth
• (00:03:49) - Donor Experience: Days Between First and Second Gifts
• (00:06:46) - Donor Welcome Series
• (00:08:31) - The decline of the everyday donor
• (00:12:12) - The Future of Fundraising: Data Literacy
• (00:16:13) - Will AI Change the Way Nonprofits Raise Money?
• (00:19:23) - Mid- and Major Donors
• (00:25:48) - Mid-level Donors: The Middle Child
• (00:27:11) - Donor Outreach
• (00:30:23) - Nonprofit Giving: Average Gift Increases
• (00:33:22) - Are You More Likely to Give Online?
• (00:34:41) - Nonprofit Giving: New Donor Acquisition
• (00:37:43) - Donors' Long Term Value
• (00:39:30) - Ask Again: How to Ask the Donor
• (00:42:07) - Virtuous Nonprofit Data 2017: Most Encouraged
• (00:45:09) - Top Nonprofit Executives Discuss the Benchmark Report
• (00:45:54) - A Few More Favors For You

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Do you know what sets the most generous fundraisers apart from the rest?
In this episode of the Rainmaker Fundraising Podcast, Andrew Olson sits down with David Duxbury, Major Gift Officer at Hammer Residences, to explore the transformative power of generosity. David shares his personal journey from growing up in poverty to becoming a passionate advocate for donor impact. Together, they discuss the importance of humility in fundraising, the role of donor-centric communication, and how nonprofits can better empower the next generation of fundraisers. Packed with honest stories and practical wisdom, this conversation will inspire anyone working to build meaningful relationships in the nonprofit sector.

Chapters

• (00:00:00) - The Rainmaker Fundraising Podcast
• (00:00:33) - Meet the Hammer Residences Major Gift Officer David Green
• (00:02:20) - In the Elevator With Charitable Givers
• (00:05:26) - Empowering the Next Generation of Fundraising
• (00:13:55) - The Importance of Humility
• (00:16:25) - How to Get Your Salesforce CRM to Do the Things You
• (00:16:57) - Donors Are Terrible People
• (00:17:37) - Philanthropist on How He Views Wealth
• (00:26:25) - Donor Centricity in Fundraising
• (00:31:11) - Donor Experience: How to Win at Fundraising
• (00:35:44) - What is Donor Stewardship?
• (00:39:42) - Top 10 Most Meaningful Donor Conversations
• (00:43:24) - The Rainmaker: Donating to Nonprofits

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

What does it really take to become a great fundraising organization?
In this powerful episode of the Rainmaker Fundraising Podcast, Andrew Olson is joined by Alan Clayton, author of Great Fundraising Organizations and founder of Revolutionise. Together, they explore what separates thriving nonprofits from those that struggle, why fundraising success starts with leadership, and how to run two distinct operations—service delivery and fundraising—under one mission. Alan shares insights from global research, practical leadership strategies, and a call to embrace emotional storytelling, strategic investment, and a purpose-driven culture

Chapters

• (00:00:00) - Alan Clayton on the Rainmaker
• (00:00:52) - Revolutionizing What It Is to Raise Money for Nonprofits
• (00:01:29) - Great fundraising organizations: The journey from good to great
• (00:03:08) - Getting organizations to commit to a five year plan
• (00:04:44) - What Makes Nonprofit Organizations Successful?
• (00:06:50) - The need for emotionally relevant engagement
• (00:09:29) - The role of the leader in fundraising
• (00:13:24) - How to Get Your Salesforce CRM to Work
• (00:13:59) - Philanthropy: The Leadership Problem
• (00:16:58) - The Conflict and Tension of the Fundraising
• (00:21:12) - The 3 Step Process of Brand Management
• (00:24:31) - In the Elevator With Andrew Carnegie
• (00:25:17) - What Makes a Charitable Leader So Driven?
• (00:28:58) - Laughably Leadership: A challenge to the
• (00:30:53) - Andrew Olson on the Biggest Mistakes Nonprofits Make
• (00:31:24) - A Few Favors for the Rainmaker

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Is your nonprofit leaving long-term donor value on the table?
In this episode of the Rainmaker Fundraising Podcast, Andrew Olson talks with Dave Raley, founder of Imago Consulting and author of The Rise of Sustainable Giving. Dave explains how the subscription economy is reshaping recurring giving and why many organizations fail to treat sustainers as the long-term partners they are. They explore the history of recurring giving, the elements of a strong sustainer program, and bust common myths about donor loyalty and communication. This episode is a must if your organization wants to grow predictable revenue and deepen donor commitment.

Chapters

• (00:00:03) - Dave Raley on Why He Started Imago Consulting
• (00:04:12) - Bookmark: The Rise of Recurring Giving
• (00:09:08) - Subscriptions and Recurring Giving
• (00:15:24) - Your 90 Day Leaders Journey Email Course
• (00:19:03) - Sustainer vs. Long Term Value
• (00:20:37) - What Makes an Organization Ready for Sustainer?
• (00:25:49) - Should I Let a Major Donor Be a Monthly Donor?
• (00:26:21) - Are Your Recurring Donors More Valuable Than Your Major Don
• (00:29:50) - When Should a Major Donor Start Giving?
• (00:33:18) - Subscriptions in the Nonprofit Industry
• (00:37:56) - Cancel Your Subscriptions?
• (00:39:54) - Sustainer Program Launch: Benchmark, Evaluate and Design
• (00:44:08) - Sustainable Giving Growth Plan
• (00:45:52) - A Few Favors For You

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Are you telling stories that truly inspire donor action?
In this episode of the Rainmaker Fundraising Podcast, Andrew Olson talks with Tayloe Clements, Director of Digital Marketing at Barna Group and host of the Mission Money podcast. Tayloe shares her journey from filmmaker to nonprofit strategist and breaks down five key elements of compelling storytelling. She explains why conflict and transformation are essential, and offers practical advice for creating impactful video content—even with limited resources. Whether you’re a seasoned marketer or just getting started, this episode will help you level up your digital storytelling.

Chapters

• (00:00:03) - Rainmaker: The Fundraising Podcast
• (00:00:46) - Taylor on His Leader Journey
• (00:02:02) - Barna the Swing dancer on How To Fit It All In
• (00:03:02) - Nonprofit Missionary
• (00:06:25) - What Excites You About Storytelling?
• (00:07:35) - The Story of Donor Engagement
• (00:11:19) - 4 Key Elements of a Mission
• (00:14:04) - Your Leadership Journey Email Course
• (00:15:48) - The Donor: The Hero of Nonprofit Marketing
• (00:19:10) - How to Coach Nonprofit Leaders on Camera
• (00:22:18) - How to Tell a Story in Video
• (00:26:15) - Andrew Olson: The Nonprofit Future
• (00:30:32) - Social Media: How to Tell the Story
• (00:33:44) - How to Start a Business in the Digital World
• (00:35:23) - A Few Favors For You

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Could treating fundraising like a skilled trade transform your results?
In this episode of the Rainmaker Fundraising Podcast, Andrew Olson sits down with Jason Zwang, founder of The Giving Group and longtime major gifts leader. Jason shares why major gift fundraising should be approached not just as a career, but as a craft that requires apprenticeship, trust-building, and continual learning. They explore the evolution of major gifts, the tension between science and art, and how organizations can prepare for the next generation of fundraising leadership. This is a masterclass in practical wisdom for anyone serious about long-term fundraising success.

Chapters

• (00:00:00) - Raising Money Through Major Gifts
• (00:01:11) - Jason Levitt on Major Gifts
• (00:04:15) - Major Gifts as a Trade
• (00:05:13) - Philanthropy as a Trade versus a Career
• (00:09:15) - How to Balance the Pressure of Delivering This Year's
• (00:13:21) - Philanthropy and the Future
• (00:18:23) - The 90 Day Leader's Journey Email Course
• (00:19:47) - David Lively: The Need for Tradecraft
• (00:24:53) - The Art of Raising Money
• (00:28:22) - 3 Rules for Success in Raising Money
• (00:31:46) - What are you most excited for in philanthropy in the coming decade
• (00:33:38) - How Do Nonprofit Pro and Pro Speak?
• (00:34:11) - A Few Favors for the Rainmaker

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

How can failure become a catalyst for growth in nonprofit leadership?
In this honest and empowering episode of the Rainmaker Fundraising Podcast, Andrew Olson is joined by Beth Fisher, CEO of Fisher Strategic. They explore how failure—especially public failure—can be one of the most powerful teachers for nonprofit leaders. Beth shares how to recover from setbacks, how to create psychologically safe cultures, and why investing in people is non-negotiable for organizations that want to grow. This episode offers practical insights for leading with authenticity, resilience, and empathy.

Chapters

• (00:00:00) - Rainmaker: Failure and What We Can Do About It
• (00:00:56) - In the Elevator With Templeton Religion Trust's Director
• (00:01:55) - What is the Risk of Failure?
• (00:07:16) - Tom Clancy on Recovering From a Big Failure
• (00:10:17) - On Coaching and the Need for Support
• (00:14:00) - Steve Jobs on How Do You Manage Your Life?
• (00:15:34) - The 90 Day Leaders' Journey Email Course
• (00:16:47) - On the Toxic Environment
• (00:18:36) - The Need for a Safe Workplace
• (00:19:54) - Performance Review and the Gray Area
• (00:21:08) - Does the Enneagram Affect How You're Seen?
• (00:22:10) - The 3 Biggest Mistakes Nonprofits Make
• (00:25:48) - WSJDLive: Leading Transformational Change
• (00:27:20) - What Have You Learned From Your Biggest Fails?
• (00:30:50) - Rainmaker: A Request for Help

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Are your fundraising and PR efforts working in harmony—or getting in each other’s way?
In this episode of the Rainmaker Fundraising Podcast, Andrew Olson sits down with Jessi Marsh, Senior Director of Creative Strategy at DickersonBakker, to explore how public relations and fundraising can support each other for greater impact. Jessi shares practical strategies for building media relationships, positioning your nonprofit as a thought leader, and coordinating PR efforts to elevate donor engagement. From crisis response to calendar planning to election-season storytelling, you’ll learn how to use the media to raise both your visibility and your revenue—without stepping on your fundraising team’s toes.

Chapters

• (00:00:00) - The Intersection of Public Relations and Raising Money
• (00:01:22) - How to Manage Public Relations?
• (00:02:56) - What is a Press Release?
• (00:04:34) - How to Plan Your Public Relations Plan
• (00:09:34) - Are You Needing a News Media Presence?
• (00:10:39) - How to Promote Yourself as a Thought Leader
• (00:12:51) - The 90 Day Leaders' Journey Email Course
• (00:14:10) - How to Leverage Public Relations to Support Fundraising
• (00:20:48) - How Do Non-profits Compete During an Election Season?
• (00:22:32) - Inflation and domestic violence
• (00:23:57) - What Do You Say to Nonprofit Leaders Who Are Afraid to
• (00:27:09) - Responsive PR for Israel's Crisis
• (00:33:11) - Jennifer Marsh and Jesse Baker on Public Relations
• (00:35:39) - A Few Favors for the Rainmaker

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Is your organization suffering from quiet decline—and would you even know it if it was?
In this episode of the Rainmaker Fundraising Podcast, Andrew Olson talks with Jim Langley, founder of Langley Innovations and former advancement leader at Georgetown, Georgia Tech, and UC San Diego. Together they explore the concept of institutional rot in the nonprofit sector, unpack why courage and curiosity are essential leadership traits, and challenge the rinse-and-repeat fundraising mindset that keeps organizations stuck. Jim shares hard truths about complacency, the decline in donor participation, and what it really takes to build lasting community and partnership. If you’re serious about the future of your organization, this conversation will wake you up and point you forward.

Chapters

• (00:00:00) - Jim Langley on Raising Money
• (00:01:57) - Philanthropy: The Vital Signs of Organizations
• (00:04:53) - The Importance of Courage
• (00:08:47) - Coronation 6: Courageous Leaders
• (00:16:50) - The 90 Day Leader's Journey Email Course
• (00:18:07) - Donor Satisfaction and the
• (00:27:03) - Philanthropy's Future
• (00:34:32) - Jim Vance on How to Reach People
• (00:35:30) - A Few Favors for the Rainmaker

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe

Get full access to The Rainmaker Fundraising Newsletter at https://rainmakerfundraising.substack.com/subscribe