Rainmaker Fundraising

Andrew Olsen
  • 4.8 (45)
  • Non-Profit
  • Biweekly

The Rainmaker Fundraising podcast, hosted by Andrew Olsen, a 25+ year veteran fundraiser who has served more than 1,000 nonprofits, helping them raise over $1 Billion is your home for candid conversations about fundraising and nonprofit leadership. You'll get high-quality conversations with fundraising practitioners, industry experts, and outsiders who bring a unique perspective to the nonprofit sector. The show also includes occasional solo episodes where Andrew addresses specific topics in-depth. rainmakerfundraising.substack.com

  1. 3d ago

    Fired for Doubling Revenue

    John Lepp’s agency recently doubled a client’s direct mail revenue. Then the client fired them, because the marketing team didn’t like how the appeal looked. That story captures the gap between what looks good and what actually raises money, and John has spent nearly 30 years on the right side of it. In this episode, the co-founder of Agents of Good explains why there’s no room for being clever in fundraising, why your appeal shouldn’t read like a doctoral thesis, why he deliberately stamped over half a client’s logo, and why AI is basically a frying pan. You’ll also hear about a mother-in-law who sends $100 without reading the letter, and a blunt bit of career advice for anyone who finds empathy hard: go work at a bank. Meet John Lepp John is co-founder and partner at Agents of Good, the Canadian fundraising and communications agency he launched with Jen Love in 2009. He cut his teeth in advertising, including a stint at a pharmaceutical agency where he learned to turn complex ideas into simple pictures. He then worked as a freelance designer and with agencies across Canada and internationally. Today he works with organizations around the world on annual and individual giving. He’s the author of Creative Deviations and a regular on conference stages, where he is famous for one thing above all: giving fundraisers permission to be human. The conversation Your donors are not grading your vocabulary John’s old boss had a rule: there’s no room for being clever in fundraising. John has honored it ever since. Clever forces donors to do cognitive work, and as he puts it, our brains are inherently lazy. Nobody wants to decode your appeal. When clients send him letters to review, he runs a readability score first. Some come back at a grade-16 reading level. His verdict is gentle but devastating: that’s not cleverness, that’s not knowing how to talk plainly. And if your organization preaches inclusion, writing at a graduate-school level (or letting your designer reverse out tiny type) quietly undercuts everything you claim to stand for. The agency that never launched Andrew noticed that Agents of Good opened its doors in 2009, smack in the middle of a global financial meltdown. John’s answer: there was no launch. A few anonymous promo videos on Twitter were enough to send an Australian agency scrambling to find out who these new competitors were. Meanwhile, John and Jen simply talked to the people they already worked with, and clients followed. The lesson he took from it applies to every charity too. Nobody cares about your anniversary, your logo colors, or your brand positioning statement. They want to know what you need from them, and whether they want to do it. Stop living in checkbox world Too many charities run on autopilot: the calendar says spring appeal, so out goes a spring appeal, with silence in between. John’s alternative is a Donor Experience System. It means consistent emotion across every touch, values that echo the donor’s values, decision-science nudges that make giving easy, and above all, identity reinforcement. Drawing on Dr. Jen Shang’s work on self-identity, John argues that giving is an expression of who we are. So hold up a mirror: tell the donor you see them as the compassionate person they are. Most charities never do. His model is Disney, where every touchpoint from the parking lot to the washrooms is built around the story. “If it’s hard for you, go work at a bank” What if you’re a tiny shop with no Disney budget? John’s answer is refreshingly simple. Make the ask abundantly clear. Sound like a group of humans who care. Make the action easy. Then actually, genuinely care about the person you’re writing to. That’s it. And if being a thoughtful, empathetic human feels hard, this might not be your sector. Andrew agreed and pushed on a harder problem: fundraisers who want to experiment but fear that one failed test takes food out of someone’s mouth. John’s wish is that more bosses and board members would sit in on these conversations at industry conferences and inside nonprofit offices everywhere, instead of saying no to ideas they have no experience judging. Why messy wins Paper clips. Crooked stamps. A stamp that deliberately covers half the logo. John knows these sound trivial, and that’s exactly the point. When a client objected to the covered logo, he told them their reaction was the reason he did it: a donor will pause and wonder why, and that pause is the hook that gets them to pay attention. “A printing press doesn’t have thumbs” (John’s pithy line). Small imperfections signal that a human, misguided as they might be, put this together for another human. But nothing is accidental. John tells his designers that every box on the page needs a reason to be there. Fired for doubling the revenue Here’s the story that made Andrew’s jaw drop. John’s agency was recently let go by a client after doubling revenue on a mail appeal, because the marketing team and development director didn’t like how the organization looked. John wrote Creative Deviations largely for marketing and comms people, and he’s careful not to blame them. But his ask of clients is simple: flag factual errors, and bring test results to anything else. His job isn’t to please you or your boss. His brief is the donor. AI is a frying pan On AI, John reaches for the kitchen. A $25 nonstick pan or a fancy All-Clad, it doesn’t matter: if you don’t know how to make an omelet, the pan won’t do it for you. He apologized for the analogy. Andrew thought it was perfect. The tougher part: John knows of agencies training bots on top writers’ copy so they no longer need to hire them, and consultants telling his own clients to do the same. He connects it to his mother-in-law, who admits she can’t read appeal letters without crying, so she just sends $100. The last thing John will do is take advantage of that kindness. Use AI as a tool, he says. But not as a replacement for real human interaction. This is a loving, emotional craft, and it needs humans in it. Take it back to your desk tomorrow * Score your next appeal before it mails. Run a readability check. If it reads at a college level or above, rewrite it the way you’d say it across a kitchen table. * Hold up a mirror. Add one line that tells the donor who they are: compassionate, generous, the kind of person who shows up for kids. Then thread it through every piece. * Fill the silence between appeals. Map what a donor hears from you between asks. If the answer is nothing, you’re living in checkbox world. * Make one intentional imperfection. A paper clip, a stamp on an angle, a handwritten note. Know exactly why it’s there. * Change the approval conversation. Ask reviewers to flag factual errors, and to bring test results for everything else. “I don’t like it” is not a brief. * Think of AI like a pan, not a chef. It’s only as good as what you put in it. A great meal is not created by the pan it’s cooked in. It’s created by the chef. It’s assembled in the pan. AI functions the same way. Lines you don’t want to miss “There’s no room for being clever in fundraising.” “If you’re writing to a grade sixteen level, you are not being inclusive.” “Our donors don’t like direct mail? Well, you’re doing it as badly as you possibly can.” “A printing press doesn’t have thumbs.” “If it’s hard for you to be a thoughtful, caring, empathetic human, go work at a bank.” “My job isn’t to figure out what you or your boss likes. My job is to do something the donor can understand, feel connected to, and give to very easily.” “It doesn’t matter what kind of pan you have. If you don’t know how to make the omelet, the pan’s not gonna do it for you.” Rainmaking: The Fundraiser’s Guide to High-Impact Offers Get the book today that is helping nonprofit organizations around the world create better, more compelling fundraising offers and raise more money for their causes. The print version is just $9.99, and the Kindle version is only $4.99. Send me an email with proof of purchase and I’ll send you an expanded Tool… Get full access to The Rainmaker Fundraising Newsletter at rainmakerfundraising.substack.com/subscribe

  2. Nov 2

    Corporate Giving Decoded

    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.” Thanks for following The Rainmaker Fundraising Podcastt! This post is public so feel free to share it. 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: 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 rainmakerfundraising.substack.com/subscribe

  3. Oct 26

    Sprinting to Success

    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: 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 rainmakerfundraising.substack.com/subscribe

  4. Oct 19

    Hungry. Humble. Hustle.

    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 as… Get full access to The Rainmaker Fundraising Newsletter at rainmakerfundraising.substack.com/subscribe

  5. Oct 8

    Building a Culture of Generosity

    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, Andrew sits 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 rainmakerfundraising.substack.com/subscribe

  6. Jul 3

    97% of wealth in America is non-cash

    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 rainmakerfundraising.substack.com/subscribe

  7. Jul 3

    Securing $100K gifts (in the mail!)

    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 rainmakerfundraising.substack.com/subscribe

  8. 08/12/2025

    Practivated: Your Virtual Fundraising Coach

    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 rainmakerfundraising.substack.com/subscribe

See All (107)

4.8
out of 5
45 Ratings

About

The Rainmaker Fundraising podcast, hosted by Andrew Olsen, a 25+ year veteran fundraiser who has served more than 1,000 nonprofits, helping them raise over $1 Billion is your home for candid conversations about fundraising and nonprofit leadership. You'll get high-quality conversations with fundraising practitioners, industry experts, and outsiders who bring a unique perspective to the nonprofit sector. The show also includes occasional solo episodes where Andrew addresses specific topics in-depth. rainmakerfundraising.substack.com

Information

  • Creator
    Andrew Olsen
  • Years Active
    2018 - 2026
  • Episodes
    107
  • Rating
    Clean
  • Copyright
    © Andrew Olsen
  • Show Website
    Rainmaker Fundraising

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